β-Hydroxy β-methylbutyric acid

5056:

functioning of cell membranes. Many biochemical studies have shown that HMB may be a precursor of cholesterol synthesis (Bachhawat et al., 1955; Bloch et al., 1954; Coon et al., 1955; Adamson and Greenberg, 1955; Gey et al., 1957). According to pertinent literature, HMB carbon is incorporated into cholesterol. Therefore, increased intramuscular HMB concentrations may provide readily available substrate for the cholesterol synthesis that is needed to form and stabilize the sarcolemma. ... It is known that HMB supplementation decreases post-exercise levels of enzymes, indicating muscle damage, such as creatinine phosphokinase (CK) and lactate dehydrogenase (LDH), which suggests an enhancement of the muscle cell membrane function. This was shown in numerous studies in humans undergoing both resistance and endurance training (Wilson et al., 2013) ... In theory, HMB use as a precursor to cholesterol could aid in stabilizing muscle cell membranes; however, this has not been confirmed by research studies. The effect of HMB on protein metabolism may in fact help stabilize muscle structure more than any effect HMB may have on cholesterol metabolism in the cell.

4556:

Leu and HMB, with the latter showing more pronounced and sustained phosphorylation. ... Nonetheless, as the overall MPS response was similar, this cellular signalling distinction did not translate into statistically distinguishable anabolic effects in our primary outcome measure of MPS. ... Interestingly, although orally supplied HMB produced no increase in plasma insulin, it caused a depression in MPB (−57%). Normally, postprandial decreases in MPB (of ~50%) are attributed to the nitrogen-sparing effects of insulin since clamping insulin at post-absorptive concentrations (5 μU ml) while continuously infusing AAs (18 g h) did not suppress MPB (Greenhaff et al. 2008), which is why we chose not to measure MPB in the Leu group, due to an anticipated hyperinsulinaemia (Fig. 3C). Thus, HMB reduces MPB in a fashion similar to, but independent of, insulin. These findings are in-line with reports of the anti-catabolic effects of HMB suppressing MPB in pre-clinical models, via attenuating proteasomal-mediated proteolysis in response to LPS (Eley et al. 2008).

5344:

well as an inhibitor of protein breakdown in the extreme case of cachexia. ... A growing body of evidence suggests HMB may help slow, or even reverse, the muscle loss experienced in sarcopenia and improve measures of muscle strength. ... However, dietary leucine does not provide a large amount of HMB: only a small portion, as little as 5%, of catabolized leucine is metabolized into HMB. ... Thus, although dietary leucine itself can lead to a modest stimulation of protein synthesis by producing a small amount of HMB, direct ingestion of HMB more potently affects such signaling, resulting in demonstrable muscle mass accretion. ... Indeed, a vast number of studies have found that supplementation of HMB to the diet may reverse some of the muscle loss seen in sarcopenia and in hypercatabolic disease. ... The overall treatment of muscle atrophy should include dietary supplementation with HMB, although the optimal dosage for each condition is still under investigation. ...

6010:

cellular respiration either directly or via effects on the ratios of acyl CoA:free CoA if further metabolism and detoxification of 3-hydroxyisovaleryl CoA does not occur (22). The transfer to carnitine by 4 carnitine acyl-CoA transferases distributed in subcellular compartments likely serves as an important reservoir for acyl moieties (39–41). 3-Hydroxyisovaleryl CoA is likely detoxified by carnitine acetyltransferase producing 3HIA-carnitine, which is transported across the inner mitochondrial membrane (and hence effectively out of the mitochondria) via carnitine-acylcarnitine translocase (39). 3HIA-carnitine is thought to be either directly deacylated by a hydrolase to 3HIA or to undergo a second CoA exchange to again form 3-hydroxyisovaleryl CoA followed by release of 3HIA and free CoA by a thioesterase.

6064:

pathways. In the first, HMB is produced from by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).

3954:

1013: 1662: 4635:

muscle deconditioning (protein turnover, apoptosis, and the regenerative process), whereas it is hypothesized to strongly affect the fourth (mitochondrial dynamics and functions). Moreover, HMB is inexpensive (~30– 50 US dollars per month at 3 g per day) and may prevent osteopenia (Bruckbauer and Zemel, 2013; Tatara, 2009; Tatara et al., 2007, 2008, 2012) and decrease cardiovascular risks (Nissen et al., 2000). For all these reasons, HMB should be routinely used in muscle-wasting conditions especially in aged people. ... 3 g of CaHMB taken three times a day (1 g each time) is the optimal posology, which allows for continual bioavailability of HMB in the body (Wilson et al., 2013)

5780:(BCAA: leucine, isoleucine and valine), in particular leucine being central to these effects (Wilkinson et al. 2013). Although the mechanisms underlying the unique anabolic properties of leucine are incompletely defined, recent work in yeast and cultured mammalians cells has demonstrated that leucyl tRNA synthetase is upstream of activating the hitherto 'cellular AA sensor', the mechanistic target of rapamycin complex 1 (mTORC1) in response to leucine (Bonfils et al. 2012, Han et al. 2012). This was reaffirmed by experiments showing that of all the EAAs, leucine is the most effective EAA in increasing the activity (i.e. phosphorylation) of mTORC1 (Atherton et al. 2010b) and its substrates. 2370: 49: 58: 4779:

rats were administered an HMBFA intervention of 0%, 0.8%, 1.6%, or 4% of the diet by body weight. The highest dose is the equivalent of ~400 mg ⋅ kg ⋅ d for humans. No adverse advents were observed for any treatment group. Similarly, blood and urine analyses were within the normal range in all groups, with no group differences. The authors concluded that HMBFA was safe for consumption in a rat model. ... No serious side effects have been reported with leucine, EAA, or HMB supplementation; and the health risks associated with these supplements are few and predictable.

2667: 4352:

protein synthesis. Its benefits in aerobic performance are probably more associated with improved mitochondrial biogenesis and fat oxidation. Favourable effects on the recovery from exercise-induced damage may be related to the role of HMB as a precursor of cholesterol, which modulates membrane fluidity and affects ion channels, and membrane excitability. ... Studies have demonstrated that HMB can prevent the development of sarcopenia in elderly subjects and that the optimal action of HMB on muscle growth and strength occurs when it is combined with exercise.

5496:

this combination in a variety of diagnoses/conditions such as HIV/AIDS patients and healthy adults. Another study, on a far larger sample base of around 470 cancer patients, found no significant difference with regard to LBM after 8 weeks however a strong trend in the direction of an increase in LBM as measured by both bio-impedance and skin-fold measurements. In summary, the effect of the combination of HMB, arginine, and glutamine on weight gain should be investigated in further studies on cancer patients investigating time periods of several months.

2349: 1171: 457: 434: 1538: 2770: 4472:

signaling cascade involved in coordination of translation initiation of muscle protein synthesis . Additionally, HMB may have antagonistic effects on the ubiquitin–proteasome pathway, a system that degrades intracellular proteins . Evidence also suggests that HMB promotes myogenic proliferation, differentiation, and cell fusion . ... Exogenous HMB-FA administration has shown to increase intramuscular anabolic signaling, stimulate muscle protein synthesis, and attenuate muscle protein breakdown in humans .

5401:

isovaleryl-CoA, while only approximately 5% of leucine is metabolized to HMB. This implies that, in order to reach pharmacological levels of HMB, this compound needs to be administered directly, rather than via increasing leucine dosage. ... HMB exerts its effects through protective, anticatabolic mechanisms and directly influences protein synthesis. HMB has also been shown to stabilize the muscle cell membrane, to modulate protein degradation and to up-regulate protein synthesis .

2067: 9863: 5544:

cellular mechanism for HMB is principally through stabilization of the cholesterol membrane in muscle cells. HMB is metabolized to β-hydroxy-β-methylglutaryl-coenzyme A (HMG-CoA) in the cytosol of muscle cells, which in turn is converted to cholesterol. ... Muscle produces its own cholesterol to maintain the integrity of the cell membrane, typically from HMG-CoA, because it cannot supply its cholesterol needs via absorption from the circulation.

6609: 9875: 6349: 4839:

tended to decrease soreness. Knitter et al. showed a decrease in LDH and creatine phosphokinase (CPK), a byproduct of muscle breakdown, by HMB after a prolonged run. ... The utility of HMB does seem to be affected by timing of intake prior to workouts and dosage . Further, chronic consumption of HMB appears safe . ... No serious adverse effects from HMB consumption have been reported.

9851: 4288:

prevention of loss of muscle strength and physical function. ... Mechanisms underlying the role of HMB in muscle regeneration have also been explored: results indicated that HMB enhances protein synthesis via upregulation of anabolic signaling pathways and attenuate proteolysis via downregulation of catabolic signaling pathways (Wilkinson et al., 2013).

5596:

Abumrad, 1997). Cholesterol is needed for the growth, repair, and stabilization of cellular membranes during exercise (Chen, 1984). ... The meta analysis studies and the individual studies conducted support the use of HMB as an effective aid to increase body strength, body composition, and to prevent muscle damage during resistance training.

1045:. These effects of HMB are more pronounced in untrained individuals and athletes who perform high intensity resistance or aerobic exercise. In resistance-trained populations, the effects of HMB on muscle strength and lean body mass are limited. HMB affects muscle size, strength, mass, power, and recovery in part by stimulating 6867:, Dalma G, Engel BG, Scott WE (1941). "Zur Kenntnis der Erythrophleum-Alkaloide. (5. Mitteilung). Identifizierung der niedermolekularen Spaltsäure des Coumingins" [Concerning erythrophleum alkaloids. (5th Communication). Identification of the low molecular weight cleavage acids from coumingin]. 5495:

Looking at studies with proteins and other dietary supplements the combination of HMB, arginine, and glutamine showed interesting results ... In one study, 32 patients gained an average of about 2 kg of body weight. This study was one of three studies confirming the positive effects of

5400:

HMB is an active leucine metabolite which activates the mTOR signaling pathway in muscle. Following its absorption, dietary leucine is converted into α-ketoisocaproate (KIC), which is further metabolized into either isovaleryl-CoA or HMB. Under normal conditions, the majority of KIC is converted into

4778:

One study tested the safety of HMB for long-term use in rats. Fuller et al. (50) conducted a 91-d study with the use of Sprague-Dawley rats that tested the safety of β-hydroxy-β-methylbutyric free acid (HMBFA). This new form of HMB results in higher HMB serum concentrations than CaHMB. In this study,

4287:

Overall, this meta-analysis indicates that HMB can prevent lean body mass loss in older adults. But the effects of HMB on muscle strength and physical function appears to vary in different populations. Additional well-designed clinical studies are necessary to confirm the effectiveness of HMB in the

6063:

HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, may follow one of two

5439:

There are a number of nutrition products on the market that are touted to improve sports performance. HMB appears to be the most promising and to have clinical applications to improve muscle mass and function. Continued research using this nutraceutical to prevent and/or improve malnutrition in the

5343:

Studies suggest dietary protein and leucine or its metabolite β-hydroxy β-methylbutyrate (HMB) can improve muscle function, in turn improving functional performance. ... These have identified the leucine metabolite β-hydroxy β-methylbutyrate (HMB) as a potent stimulator of protein synthesis as

4712:

Normally, an individual metabolizes 60 g of L-LEU to obtain 3 g of HMB but a 70 kg person produces 0.2–0.4 g of HMB per day, depending on the dose of LEU in the diet (Van Koevering and Nissen 1992). ... The usual dose of 3 g/day may be routinely recommended to maintain

3953:

3352:

that the company has used to license the right to manufacture and incorporate HMB into dietary supplements. When it first became available commercially in the late 1990s, HMB was marketed solely as an exercise supplement to help athletes and bodybuilders build muscle. MTI subsequently developed two

6135:

Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids,

4555:

The stimulation of MPS through mTORc1-signalling following HMB exposure is in agreement with pre-clinical studies (Eley et al. 2008). ... Furthermore, there was clear divergence in the amplitude of phosphorylation for 4EBP1 (at Thr37/46 and Ser65/Thr70) and p70S6K (Thr389) in response to both

3804:

The has concluded the following. 1. HMB can be used to enhance recovery by attenuating exercise induced skeletal muscle damage in trained and untrained populations. ... 4. Thirty-eight mg·kg·BM daily of HMB has been demonstrated to enhance skeletal muscle hypertrophy, strength, and power in

1132:

in young adults or older adults have been reported when HMB is taken in doses of 3 grams per day for up to a year. Studies on young adults taking 6 grams of HMB per day for up to 2 months have also reported no adverse effects. Studies with supplemental HMB on young, growing rats and

4838:

Currently, HMB is available as an over-the-counter supplement. The drug is not tested for nor banned by any sporting organization. ... Wilson et al. demonstrated that when non-resistance trained males received HMB pre-exercise, the rise of lactate dehydrogenase (LDH) levels reduced, and HMB

1036:

With an appropriate exercise program, dietary supplementation with 3 grams of HMB per day has been shown to increase exercise-induced gains in muscle size, muscle strength and power, and lean body mass, reduce exercise-induced skeletal muscle damage, and expedite recovery from high-intensity

6009:

Reduced activity of MCC impairs catalysis of an essential step in the mitochondrial catabolism of the BCAA leucine. Metabolic impairment diverts methylcrotonyl CoA to 3-hydroxyisovaleryl CoA in a reaction catalyzed by enoyl-CoA hydratase (22, 23). 3-Hydroxyisovaleryl CoA accumulation can inhibit

5875:

In an experimental animal model of cancer-induced cachexia, HMB treatment not only down-regulated the expression of key regulatory components of 19S and 20S proteasome–proteolytic pathway but also stimulated protein synthesis which further regulates the loss of muscle mass . ... HMB is also

5779:

The mechanisms underlying the anabolic effects of food intake involve both the stimulation of MPS (Rennie et al. 1982) and suppression of MPB (Wilkes et al. 2009). The potent increase in MPS is driven almost entirely by essential amino acids (EAAs) (Smith et al. 1992), with the branched chain AA

5595:

HMB, a derivative of leucine, prevents muscle damage and increases muscle strength by reducing exercise-induced proteolysis in muscles and also helps in increasing lean body mass. ... HMB is converted to HMB-CoA which is then used for the synthesis of cholesterol in muscle cells (Nissen and

5055:

Cholesterol is a major component of the cell membrane, and sarcolemma is the one that relies mainly on de novo synthesis of cholesterol. This is important under stressful conditions when muscle cells may lack the capacity to produce adequate amounts of the cholesterol that is essential to proper

4634:

In conclusion, HMB treatment clearly appears to be a safe potent strategy against sarcopenia, and more generally against muscle wasting, because HMB improves muscle mass, muscle strength, and physical performance. It seems that HMB is able to act on three of the four major mechanisms involved in

4471:

HMB's mechanisms of action are generally considered to relate to its effect on both muscle protein synthesis and muscle protein breakdown (Figure 1) . HMB appears to stimulate muscle protein synthesis through an up-regulation of the mammalian/mechanistic target of rapamycin complex 1 (mTORC1), a

4351:

The reports summarized here indicate that HMB provides a number of benefits to subjects involved in strength-power and endurance sports. The effects on muscle mass and strength, particularly during resistance training, are likely related to the suppression of proteolysis and a positive effect on

950:

Clinical trials that used HMB for the treatment of muscle wasting have involved the administration of 3 grams of HMB per day under different dosing regimens. According to one review, an optimal dosing regimen is to administer it in one 1 gram dose, three times a day, since this ensures

6293:

Dorna; Varshavi, Dorsa; Allen, Dana; Arndt, David; Khetarpal, Nitya; Sivakumaran, Aadhavya; Harford, Karxena; Sanford, Selena; Yee, Kristen; Cao, Xuan; Budinsky, Zachary; Liigand, Jaanus; Zhang, Lun; Zheng, Jiamin; Mandal, Rupasri; Karu, Naama; Dambrova, Maija; Schiöth, Helgi B.; Gautam, Vasuk.

6292:

Wishart, David S.; Guo, An Chi; Oler, Eponine; Wang, Fel; Anjum, Afia; Peters, Harrison; Dizon, Raynard; Sayeeda, Zinat; Tian, Siyang; Lee, Brian L.; Berjanskii, Mark; Mah, Robert; Yamamoto, Mai; Jovel Castillo, Juan; Torres Calzada, Claudia; Hiebert Giesbrecht, Mickel; Lui, Vicki W.; Varshavi,

5543:

More than 20 publications in humans have demonstrated benefit with HMB supplementation associated with increased lean body mass without fat gain, improved markers of muscle strength, and decreased onset of muscle soreness with training and reduced markers of muscle damage. ... One proposed

4892:

Recently, the free acid form of HMB (HMB-FA) has become commercially available in capsule form (gelcap). The current study was conducted to compare the bioavailability of HMB using the two commercially available capsule forms of HMB-FA and Ca-HMB. ... In conclusion, HMB-FA in capsule form

4135:

Dr. Nissen and his collaborator Dr. Naji N. Abumrad, Professor and Chair, Department of Surgery, Vanderbilt University, discovered beta-hydroxy-beta-methylbutyrate (HMB) and its beneficial effects on human health and performance. HMB is currently marketed nationally by Abbott Laboratories as

1152:

Two animal studies have examined the effects of HMB supplementation in pregnant pigs on the offspring and reported no adverse effects on the fetus. No clinical testing with supplemental HMB has been conducted on pregnant women, and pregnant and lactating women are advised not to take HMB by

4191:

The questions about what defines a medical food will likely grow as the market does—and that market now extends far beyond PKU and other inherited metabolic disorders. ... Abbott Nutrition's Juven provides nutrients to people with HIV or AIDS experiencing excessive weight loss due to

3805:

untrained and trained populations when the appropriate exercise prescription is utilized. ... 8. HMB's mechanisms of action include an inhibition and increase of proteolysis and protein synthesis, respectively. 9. Chronic consumption of HMB is safe in both young and old populations.

3357:

obtained the market rights in 2003 and 2008 respectively. Since then, Abbott has marketed Juven as a medical food and the Revigor brand of HMB as an active ingredient in food products (e.g., certain formulations of Ensure) and other medical foods (e.g., certain formulations of Juven).

1072:

The efficacy of HMB supplementation for reducing skeletal muscle damage from prolonged or high-intensity exercise is affected by the time that it is used relative to exercise. The greatest reduction in skeletal muscle damage from a single bout of exercise has been shown to occur when

5660:

Sanchez-Martinez J, Santos-Lozano A, Garcia-Hermoso A, Sadarangani KP, Cristi-Montero C (July 2018). "Effects of beta-hydroxy-beta-methylbutyrate supplementation on strength and body composition in trained and competitive athletes: A meta-analysis of randomized controlled trials".

4402:

Clinical trials performed in older adults confirm that HMB can attenuate the progression of sarcopenia in elderly subjects. HMB supplementation results in an increase in skeletal muscle mass and strength in the elderly and its effect is even greater when combined with physical

1387:(IGF-1) via an unknown mechanism, in turn promoting protein synthesis through increased mTOR phosphorylation. Based upon limited clinical evidence in humans, supplemental HMB appears to increase the secretion of growth hormone and IGF-1 in response to resistance exercise. 5289:

HMB is widely used as an ergogenic supplement by young athletes. ... This study shows that in healthy older adult, HMB supplementation may preserve muscle mass during 10 days of bed rest. These results are encouraging, but need to be confirmed by other

6828:

Ehling S, Reddy TM (February 2014). "Investigation of the presence of β-hydroxy-β-methylbutyric acid and α-hydroxyisocaproic acid in bovine whole milk and fermented dairy products by a validated liquid chromatography-mass spectrometry method". primary source.

6789:

Ehling S, Reddy TM (September 2015). "Direct Analysis of Leucine and Its Metabolites β-Hydroxy-β-methylbutyric Acid, α-Ketoisocaproic Acid, and α-Hydroxyisocaproic Acid in Human Breast Milk by Liquid Chromatography-Mass Spectrometry". primary source.

5876:

involved in the regulation of satellite cell proliferation probably through reduction of nuclear apoptosis . Overall, HMB treatments regulate skeletal muscle wasting by stimulating protein anabolic and inhibiting protein catabolic pathways (Fig. 3).

4207: 943:; consequently, the authors of two 2016 reviews of the clinical evidence recommended that the prevention and treatment of sarcopenia and muscle wasting in general include supplementation with HMB, regular resistance exercise, and consumption of a 5893:

Kornasio R, Riederer I, Butler-Browne G, Mouly V, Uni Z, Halevy O (May 2009). "Beta-hydroxy-beta-methylbutyrate (HMB) stimulates myogenic cell proliferation, differentiation and survival via the MAPK/ERK and PI3K/Akt pathways". primary source.

4367:

Rossi AP, D'Introno A, Rubele S, Caliari C, Gattazzo S, Zoico E, Mazzali G, Fantin F, Zamboni M (October 2017). "The Potential of β-Hydroxy-β-Methylbutyrate as a New Strategy for the Management of Sarcopenia and Sarcopenic Obesity".

5613:

Rahimi MH, Mohammadi H, Eshaghi H, Askari G, Miraghajani M (2018). "The Effects of Beta-Hydroxy-Beta-Methylbutyrate Supplementation on Recovery Following Exercise-Induced Muscle Damage: A Systematic Review and Meta-Analysis".

2506: 4713:

or improve muscle mass and function in health and disease. The safety profile of HMB is unequivocal. ... These results show that HMB/ARG/GLN can be safely used to treat AIDS- and cancer-related muscle wasting

4260:

Wu H, Xia Y, Jiang J, Du H, Guo X, Liu X, Li C, Huang G, Niu K (September 2015). "Effect of beta-hydroxy-beta-methylbutyrate supplementation on muscle loss in older adults: a systematic review and meta-analysis".

6607:, Noti C, Schmid L, Rittiner B, Hanselmann P, Bierstedt A, "Process for the preparation of 3-hydroxy-3-methylbutyric acid or its calcium salts", published 10 January 2013, assigned to Lonza Ltd 5140: 4215: 4515:

Wilkinson DJ, Hossain T, Hill DS, Phillips BE, Crossland H, Williams J, Loughna P, Churchward-Venne TA, Breen L, Phillips SM, Etheridge T, Rathmacher JA, Smith K, Szewczyk NJ, Atherton PJ (June 2013).

5648:

The current evidence revealed a time-dependent effect of HMB in reducing LDH and CK serum levels among adults. HMB, therefore, may be seen as a priority muscle damage recovery agent in interventions.

3829: 5346:

It is currently recommended that patients at risk of or suffering from sarcopenia consume a diet high in protein, engage in resistance exercise, and take supplements of the leucine metabolite HMB.

1390:

As of 2016, the signaling cascade that mediates the HMB-induced reduction in muscle protein breakdown has not been identified in living humans, although it is well-established that it attenuates

3762:

Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J (February 2013).

1621:

and which occurs sooner relative to lower doses. Consumption of HMB-Ca with sugary substances slows the rate of HMB absorption, resulting in a lower peak plasma HMB level that occurs later.

5457:"A systematic review on the role of vitamins, minerals, proteins, and other supplements for the treatment of cachexia in cancer: a European Palliative Care Research Centre cachexia project" 1661: 1606:

is ingested, the magnitude and time at which the peak plasma concentration of HMB occurs depends on the dose and concurrent food intake. Higher HMB-Ca doses increase the rate of

836:

and muscle can only be achieved by supplementing HMB directly. A healthy adult produces approximately 0.3 grams per day, while supplemental HMB is usually taken in doses of

7855: 3587:

secretion and consequently was not measured in the same study. By comparison, the insulin-dependent reduction in muscle protein breakdown following an entire meal that contains

7086: 3026: μg/L. This concentration is far too low to be an adequate dietary source of HMB for obtaining pharmacologically active concentrations of the compound in blood plasma. 6347:, White TO, "Stable liquid filled hard capsule comprising beta-hydroxy-beta-methylbutyric acid", published 25 June 2015, assigned to Capsugel Belgium Nv 4136:

Revigor™, which is a component of Ensure® Muscle Health, and Juven®, which is a nutritional beverage that is clinically shown to promote healing after injury or surgery.

3612:

at 2 hours following ingestion, while ingestion of a 3 gram dose of HMB-Ca produced a peak plasma HMB level of 487 μM at 1 hour following ingestion.

8193: 8144: 7210: 4951:"Effects of beta-hydroxy-beta-methylbutyrate (HMB) on exercise performance and body composition across varying levels of age, sex, and training experience: A review" 919:

older adults. HMB does not appear to significantly affect fat mass in older adults. Preliminary clinical evidence suggests that HMB supplementation may also prevent

5971:"Urinary excretion of 3-hydroxyisovaleric acid and 3-hydroxyisovaleryl carnitine increases in response to a leucine challenge in marginally biotin-deficient humans" 4910: 3522:. No adverse effects were observed in any group that received HMB, so the highest daily dose of HMB that was administered in this study was identified as the NOAEL. 1641:

of the dose is retained in tissues or excreted as HMB metabolites. The fraction of a given dose of HMB that is excreted unchanged in urine increases with the dose.

8139: 6894:

Tanaka K, Orr JC, Isselbacher KJ (May 1968). "Identification of beta-hydroxyisovaleric acid in the urine of a patient with isovaleric acidemia". primary source.

1004:. Further research involving the treatment of cancer cachexia with Juven over a period of several months is required to adequately determine treatment efficacy. 951:

elevated plasma concentrations of HMB throughout the day; however, as of 2016 the best dosing regimen for muscle wasting conditions is still being investigated.

2627:

in 1880 and 1889, Schirokoff and Reformatsky (respectively) reported that the oxidative cleavage of the vicinal diol 4-methylpentane-1,2,4-triol with acidified

8069: 5233: 5711: 115: 3822: 2993:

has been measured at 7.0 μM. In the urine of healthy individuals of any age, the excreted urinary concentration of HMB has been measured in a range of

6444:[On the β-dipropyl- and β-diethylenyl-lactic acid, and on the oxidation of the allyl dimethylcarbinol and diallylcarbinol with excess potassium]. 3861: 7848: 6442:"Ueber die β-Dipropyl- und β-Diäthyläthylenmilchsäure und über die Oxydation des Allyldimethylcarbinols und Diallylcarbinols mit übermangansaurem Kalium" 6165: 8353: 5849:

Dutt V, Gupta S, Dabur R, Injeti E, Mittal A (September 2015). "Skeletal muscle atrophy: Potential therapeutic agents and their mechanisms of action".

5172: 4118: 7079: 3627:

In one study, ingestion of a 1 gram and 3 gram HMB dose resulted in the excretion of 14% and 28% of the dose as HMB in urine, respectively.

3410: 6122: 3973: 1446:

may help stabilize muscle cell structure. One review suggested that the observed HMB-induced reduction in the plasma concentration of muscle damage

612: 8283: 3442:

The meta-analysis found that the average increase in muscle mass due to HMB supplementation in older adults was 0.35 kilograms (0.77 lb). The

3037:

to 408 μM after 30 minutes. At 150 minutes post-ingestion, the average plasma HMB concentration among participants was 275 μM.

2461: 8079: 4430:"β-hydroxy-β-methylbutyrate free acid supplementation may improve recovery and muscle adaptations after resistance training: a systematic review" 974:

following surgery or injury, or when otherwise recommended by a medical professional. Juven, a nutrition product which contains 3 grams of

9251: 8074: 7841: 6626:

Kohn M (September 1903). "Zur Kenntnis des Diacetonalkohols und des Mesityloxyds" [Knowledge of diacetone alkohols and mesityl oxide].

4090:

Chemical Names: Beta-Hydroxyisovaleric acid; 3-Hydroxy-3-methylbutanoic acid; ... 3-Hydroxyisovaleric acid; 3-Hydroxy-3-methylbutyric acid

5969:

Mock DM, Stratton SL, Horvath TD, Bogusiewicz A, Matthews NI, Henrich CL, Dawson AM, Spencer HJ, Owen SN, Boysen G, Moran JH (November 2011).

8956: 8149: 6102: 8400: 8166: 7072: 6976: 2267: 927:. A growing body of evidence supports the efficacy of HMB in nutritional support for reducing, or even reversing, the loss of muscle mass, 847:

per month when taken in doses of 3 grams per day. HMB is also contained in several nutritional products and medical foods marketed by

567: 6322: 6149: 2966: 1260: 6709: 6374: 1037:

exercise. Based upon limited clinical research, HMB supplementation may also improve aerobic exercise performance and increase gains in

6550:

Grosset (1893). "Ueber die Einwirkung von Mineralsauren auk Dimethylallen" [On the action of mineral acids on dimethylallyls].

2253: 1684: 4862:"Comparison of availability and plasma clearance rates of β-hydroxy-β-methylbutyrate delivery in the free acid and calcium salt forms" 1752: 6025:

Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011).

4041: 3915:

Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011).

3448:

The seven randomized controlled trials that were included in the meta-analysis contained a total of 147 older adults in the HMB

2647:

further oxidises to carbonyl-containing compounds, and the diol intermediate is not obtained when hot acidic conditions are used for

1347: 1058: 716:

per month when taking 3 grams per day. HMB is also contained in several nutritional products, including certain formulations of

5724:

Pregnant or lactating women are advised against taking HMB because safety studies have not yet been conducted for these populations.

5561:

Luckose F, Pandey MC, Radhakrishna K (2015). "Effects of amino acid derivatives on physical, mental, and physiological activities".

3048:. The following table lists some of these disorders along with the associated HMB concentrations detected in urine or blood plasma. 690:

indicate that HMB supplementation also helps to preserve or increase lean body mass and muscle strength in individuals experiencing

2970: 2326:(KIC dioxygenase), which converts α-KIC to HMB. In healthy individuals, this minor pathway – which involves the conversion of 1526: 1101: 760: 9895: 8064: 2962: 6203: 5942: 5263:

Cruz-Jentoft AJ (2018). "Beta-hydroxy-beta-methyl butyrate (HMB): From experimental data to clinical evidence in sarcopenia".

9805: 7281: 6946: 6703: 6674: 6522: 6116: 5134: 5090: 4077: 4004:

Coffman DD, Cramer R, Mochel WE (June 1958). "Syntheses by Free-radical Reactions. V. A New Synthesis of Carboxylic Acids".

1482:, which potentially increases the regenerative capacity of skeletal muscle, by increasing the protein expression of certain 1017: 8993: 8712: 7907: 7594: 7185: 6506: 3608:

In one study, ingestion of a 1 gram dose of HMB-Ca by healthy volunteers produced a peak plasma HMB level of 120

4208:"JUVEN Added to Abbott Laboratories' Nutritional Product Line for People With Cancer, HIV/AIDS and Wounds/Pressure Ulcers" 1578:

higher than for HMB-Ca. The fraction of an ingested dose that is excreted in urine does not differ between the two forms.

1458:) in humans following intense exercise may be due to a cholesterol-mediated improvement in muscle cell membrane function. 7912: 7190: 4921: 2323: 1815: 1766: 3040:

Abnormal HMB concentrations in urine and blood plasma have been noted in several disease states where it may serve as a

1137:

or observable characteristics; for humans younger than 18, there is limited data on the safety of supplemental HMB. The

2110: 5513:"Elderly persons with ICU-acquired weakness: the potential role for β-hydroxy-β-methylbutyrate (HMB) supplementation?" 9910: 8949: 5226: 587: 4076:. United States National Library of Medicine – National Center for Biotechnology Information. 3 February 2018. 9950: 9822: 8393: 8059: 5707: 4804:

Momaya A, Fawal M, Estes R (April 2015). "Performance-enhancing substances in sports: a review of the literature".

1507: 1142: 1042: 5124: 4666:"Beta-hydroxy-beta-methylbutyrate supplementation in health and disease: a systematic review of randomized trials" 3618:

resulted in a lower peak plasma HMB level of 352 μM which occurred later at 2 hours following ingestion.

9900: 7416: 5077:

Diet Cults: The Surprising Fallacy at the Core of Nutrition Fads and a Guide to Healthy Eating for the Rest of Us

3216: 1988: 1517:. HMB-induced human myosatellite differentiation and accelerated fusion of myosatellite cells into muscle tissue 1420: 1343: 1225: 271: 136: 8241: 3446:

for the estimated increase in muscle mass due to HMB supplementation is 0.11–0.59 kilograms (0.24–1.30 lb).

3022: mg/L. In comparison, HMB has been detected and measured in the milk of healthy cows at a concentration of 520: 9940: 8847: 8054: 6406: 4429: 4313:"Beta-hydroxy-beta-methylbutyrate supplementation and skeletal muscle in healthy and muscle-wasting conditions" 3854: 3312: 2609: 2163: 2147: 1961: 1952: 1270: 6173: 4517:"Effects of leucine and its metabolite β-hydroxy-β-methylbutyrate on human skeletal muscle protein metabolism" 1411:-independent manner in humans. HMB is believed to reduce muscle protein breakdown in humans by inhibiting the 7445: 5120: 1607: 5358:

Landi F, Calvani R, Tosato M, Martone AM, Ortolani E, Savera G, D'Angelo E, Sisto A, Marzetti E (May 2016).

4594: 767:, or any other prominent national or international athletic organization. In 2006, only about 2% of college 9915: 8942: 8707: 8005: 7575: 5165: 4122: 3453: 3449: 3345: 2279: 1943: 1384: 1240: 1157:, the company that grants licenses to include HMB in dietary supplements, due to a lack of safety studies. 1154: 1012: 958:

that are intended to be used to provide nutritional support under the care of a doctor in individuals with

452: 353: 8852: 6225: 9955: 9930: 8386: 8089: 7984: 7956: 7753: 7286: 6604: 6344: 3969: 3552:, in the skeletal muscle of living humans. At 150 minutes post-ingestion, these doses of HMB-FA and 3168: 1997: 1483: 912: 413: 6577:

Gresham TL, Jansen JE, Shaver FW, Beears WL (January 1954). "β-Propiolactone. XIV. β-Isovalerolactone".

5413:

Mullin GE (February 2014). "Nutrition supplements for athletes: potential application to malnutrition".

3472:

The effect of HMB on skeletal muscle damage has been assessed in studies on humans using four different

9925: 9841: 9741: 9682: 9533: 9310: 7054: 3264: 2662:

in 1892, Kondakow reported the preparation of HMB by permanganate oxidation of 3-methylbutane-1,3-diol.

1618: 1319:

that mediates the HMB-induced increase in human skeletal muscle protein synthesis have been identified

1025: 5739:

Brook MS, Wilkinson DJ, Phillips BE, Perez-Schindler J, Philp A, Smith K, Atherton PJ (January 2016).

1096:

in the United States used HMB as a dietary supplement. As of 2017, HMB has found widespread use as an

771:

in the United States used HMB as a dietary supplement. As of 2017, HMB has found widespread use as an

9350: 9053: 9048: 8318: 8251: 8084: 7979: 7974: 7642: 7550: 7276: 7200: 2705:

provides another pathway to HMB involving the exhaustive halogenation of the methyl-ketone region of

2215: 2135: 1744: 1732: 7225: 4428:

Silva VR, Belozo FL, Micheletti TO, Conrado M, Stout JR, Pimentel GD, Gonzalez AM (September 2017).

3544:(3.42 grams) do not produce statistically distinguishable anabolic effects, as measured by the 3497:. When exercise intensity and volume are sufficient to cause skeletal muscle damage, such as during 429: 9713: 8822: 7945: 7763: 7570: 7426: 7205: 7058: 6540:

Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (Journal of the Russian Physico-Chemical Society)

3443: 3240: 3192: 2722: 2020: 1595: 1466: 1189: 1105: 764: 670:. In healthy adults, supplementation with HMB has been shown to increase exercise-induced gains in 7833: 7629: 5741:"Skeletal muscle homeostasis and plasticity in youth and ageing: impact of nutrition and exercise" 4362: 4360: 3764:"International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)" 2557: 33: 9920: 9810: 9018: 8423: 8023: 7609: 7565: 7393: 7166: 7001: 6027:"HMB supplementation: clinical and athletic performance-related effects and mechanisms of action" 3917:"HMB supplementation: clinical and athletic performance-related effects and mechanisms of action" 1230: 682:

damage from exercise, improve aerobic exercise performance, and expedite recovery from exercise.

97: 17: 7064: 6969: 6696:

Organometallic Mechanisms and Catalysis: The Role of Reactive Intermediates in Organic Processes

5511:

Rahman A, Wilund K, Fitschen PJ, Jeejeebhoy K, Agarwala R, Drover JW, Mourtzakis M (July 2014).

5360:"Protein Intake and Muscle Health in Old Age: From Biological Plausibility to Clinical Evidence" 5082: 3574:

decreased skeletal muscle protein breakdown in living humans by 57% in one study. The effect of

3505:, HMB supplementation has been demonstrated to attenuate the rise in these biomarkers by 20–60%. 2564: 2127: 9718: 9325: 9277: 9194: 9038: 8827: 8232: 8112: 8042: 7871: 7818: 7697: 7674: 7512: 7421: 7348: 7253: 7141: 7101: 4357: 3367: 3317: 3087: 2656: 2628: 1840: 1574:(3 hours) relative to HMB-Ca (2.5 hours). Tissue uptake and utilization of HMB-FA is 1375:). Supplementation with HMB in several non-human animal species has been shown to increase the 1235: 8293: 7664: 6970:"The University of Iowa Economic Development Grow Iowa Values Fund Proposal: Fiscal Year 2011" 6662: 6366: 6314: 6140: 5455:

Mochamat, Cuhls H, Marinova M, Kaasa S, Stieber C, Conrad R, Radbruch L, Mücke M (July 2016).

5312: 3456:. The seven trials had durations of 2–11 months and the average duration of the studies, 1549:) over time following ingestion of a 1 gram dose of the calcium or free acid form of HMB. 1170: 402: 9935: 9905: 9505: 9470: 9380: 9227: 9176: 8453: 8000: 7969: 7634: 7310: 6691: 5799:"Nutritional supplements in support of resistance exercise to counter age-related sarcopenia" 3498: 3484: 3337: 3033:

while fasting, the average plasma HMB concentration increased from a basal level of 5.1

2553: 1571: 1455: 1356: 1326: 1138: 752: 557: 5313:"Skeletal Muscle Regulates Metabolism via Interorgan Crosstalk: Roles in Health and Disease" 2099:

is mostly metabolized into isovaleryl-CoA, while only about 5% is metabolized into HMB.

954:

Some branded products that contain HMB (i.e., certain formulations of Ensure and Juven) are

9370: 9232: 9204: 9141: 8842: 8438: 8303: 8198: 8176: 7109: 7098: 6864: 6740: 3545: 3502: 3473: 3322: 3041: 2762: 2151: 1495: 1447: 1265: 1097: 1001: 842: 772: 711: 362: 342: 229: 5104:

HMB was discovered in the mid-1990s by Steve Nissen, a researcher at Iowa State University

4035: 2659:

of 2-methylpent-4-en-2-ol and β-hydroxy β-methylbutyric acid is a derivative of both; and,

2433:

acid occurs as a transparent, colorless to light yellow liquid which is soluble in water.

2258: 204: 8: 9945: 9282: 9257: 9237: 9222: 9131: 9126: 9111: 9106: 9101: 8722: 7810: 7599: 7291: 7271: 6024: 3914: 3336:

The effects of HMB on human skeletal muscle were first discovered by Steven L. Nissen at

3330: 2978: 2974: 2847: 2741: 2714: 2601: 2594: 2369: 2295: 2123: 1936: 1910: 1889: 1611: 1368: 1275: 904: 848: 751:

The effects of HMB on human skeletal muscle were first discovered by Steven L. Nissen at

297: 288: 104: 48: 6744: 6020: 6018: 2635:) yields HMB – this result is closest related to the first synthesis as cold dilute KMnO 895:

as a treatment for preserving lean body mass in muscle wasting conditions, particularly

456: 433: 9696: 9518: 9390: 9242: 9161: 9116: 9033: 8985: 8965: 8893: 8807: 8782: 8752: 8747: 8609: 8493: 8473: 8448: 8409: 7879: 7220: 6643: 6054: 5995: 5970: 5823: 5798: 5765: 5740: 5686: 5639: 5586: 5481: 5456: 5386: 5359: 5075: 4977: 4950: 4829: 4764: 4739: 4703: 4625: 4541: 4516: 4393: 4337: 4312: 4182: 3944: 3910: 3790: 3763: 3515: 3308: 3291: 3045: 2730: 2718: 2710: 2586: 2188: 1831: 1599: 1474: 1462: 1443: 1279: 1134: 1029: 915:, HMB supplementation can preserve or increase lean muscle mass and muscle strength in 792: 647: 6761: 6724: 5659: 5276: 5200: 3908: 3906: 3904: 3902: 3900: 3898: 3896: 3894: 3892: 3890: 1693: 832:, is metabolized into HMB, pharmacologically active concentrations of the compound in 9764: 9759: 9600: 9500: 9495: 9457: 9375: 9287: 9267: 9247: 9171: 9166: 9151: 9136: 9121: 9073: 9068: 9043: 9008: 9003: 8797: 8531: 8122: 7758: 7716: 6942: 6911: 6907: 6846: 6807: 6766: 6752: 6699: 6670: 6518: 6112: 6046: 6015: 6000: 5911: 5866: 5828: 5770: 5678: 5631: 5578: 5534: 5486: 5430: 5391: 5334: 5311:

Argilés JM, Campos N, Lopez-Pedrosa JM, Rueda R, Rodriguez-Mañas L (September 2016).

5280: 5130: 5086: 5046: 4982: 4893:

improves clearance rate and availability of HMB compared with Ca-HMB in capsule form.

4883: 4821: 4769: 4695: 4617: 4546: 4462: 4385: 4342: 4278: 4186: 4174: 3936: 3795: 3493: 2745: 2706: 2702: 2531: 2527: 2403: 2287: 2109:

The metabolism of HMB is catalyzed by an uncharacterized enzyme which converts it to

2072: 1970: 1434:

Based upon animal studies, HMB appears to be metabolized within skeletal muscle into

1316: 1220: 1181: 1146: 1054: 1050: 944: 699: 695: 683: 57: 6647: 6195: 6058: 6026: 5934: 5844: 5842: 5690: 5590: 4833: 4629: 4595:"Muscle wasting and aging: Experimental models, fatty infiltrations, and prevention" 3948: 3916: 2395: 9867: 9659: 9651: 9605: 9582: 9564: 9452: 9345: 9330: 9320: 9272: 9262: 9146: 9028: 9013: 8732: 8540: 7940: 7266: 7146: 6934: 6903: 6876: 6838: 6799: 6756: 6748: 6635: 6603: 6586: 6559: 6514: 6484: 6453: 6422: 6038: 5990: 5982: 5903: 5858: 5818: 5810: 5760: 5752: 5670: 5643: 5623: 5570: 5524: 5476: 5468: 5422: 5381: 5371: 5324: 5272: 5036: 4972: 4962: 4873: 4813: 4759: 4751: 4733: 4731: 4729: 4727: 4725: 4723: 4721: 4707: 4687: 4677: 4609: 4536: 4528: 4452: 4444: 4397: 4377: 4332: 4324: 4270: 4164: 4013: 3928: 3887: 3785: 3775: 3457: 3354: 2648: 2542: 2455: 2354: 1979: 1567: 1522: 1038: 808: 789: 469: 167: 6725:"Conversion of beta-methylbutyric acid to beta-hydroxy-beta-methylbutyric acid by 5627: 5258: 5256: 5254: 4274: 4255: 4253: 4071: 1442:, thereby enhancing membrane integrity and function. The effects of HMB on muscle 322: 9855: 9787: 9769: 9736: 9677: 9628: 9623: 9528: 9423: 9335: 9305: 9199: 9156: 9078: 9058: 9023: 8998: 8792: 8467: 8443: 7902: 7560: 7368: 6502: 6398:

The earliest citation for the synthesis of β-hydroxy β-methylbutyric acid in the

6153: 6106: 5907: 5839: 5574: 4532: 4448: 4251: 4249: 4247: 4245: 4243: 4241: 4239: 4237: 4235: 4233: 3514:

The NOAEL was established based upon a 3-month study involving several groups of

3480: 2737: 2523: 2399: 2392: 2027: 1728: 1451: 1339: 1215: 1121: 1093: 900: 768: 679: 643: 211: 108: 6938: 5674: 5556: 5554: 5552: 5329: 5023:

Szcześniak KA, Ostaszewski P, Fuller JC, Ciecierska A, Sadkowski T (June 2015).

4718: 2314:

into HMB respectively. A relatively small amount of α-KIC is metabolized in the

1338:, HMB has been shown to increase protein synthesis in human skeletal muscle via 9879: 9816: 9667: 9513: 9475: 9418: 9395: 9385: 9365: 9355: 9340: 9315: 9083: 9063: 8877: 8832: 8576: 8363: 8348: 8330: 7964: 7555: 7195: 7156: 5862: 5608: 5606: 5604: 5251: 3561:

increased muscle protein synthesis by ~70% and ~110% respectively in one study.

2957:

The concentration of naturally produced HMB has been measured in several human

2275: 2076: 1900: 1879: 1859: 1849: 1779: 1380: 1129: 1125: 997: 959: 936: 920: 892: 812: 703: 675: 659: 630: 87: 78: 7037: 7031: 7025: 7019: 7013: 6880: 6042: 5406: 4878: 4861: 4817: 4682: 4665: 4613: 4381: 4230: 3932: 9889: 9547: 9400: 9360: 8913: 8742: 8727: 8462: 8298: 7927: 7740: 7707: 7669: 7527: 7411: 6803: 6563: 6488: 6457: 6426: 5549: 5529: 5512: 5426: 5025:"Dietary supplementation of β-hydroxy-β-methylbutyrate in animals – a review" 4588: 4586: 4584: 3878: • Administer orally or as a modular via feeding tube ... 3488: 3348:(MTI) around the time of his discovery, which later acquired six HMB-related 2726: 2682: 2539: 2181: 1927: 1145:(NOAEL) that was identified in a rat model is approximately 0.4 g/kg of 971: 908: 687: 655: 551: 541: 445: 8934: 6929:

Tanaka K (1975). "Disorders of Organic Acid Metabolism". In Gaull GE (ed.).

5601: 4855: 4853: 4851: 4849: 4847: 4582: 4580: 4578: 4576: 4574: 4572: 4570: 4568: 4566: 4564: 4510: 4508: 4506: 4504: 4502: 4500: 3438: 3436: 2612:

reported the preparation of HMB by oxidation of 2-methylpent-4-en-2-ol with

724:. HMB is also present in insignificant quantities in certain foods, such as 9646: 8969: 8918: 8428: 8288: 8278: 7778: 7656: 7532: 7363: 7296: 7161: 7151: 7131: 6850: 6811: 6294: 6050: 6004: 5915: 5870: 5832: 5774: 5682: 5635: 5582: 5538: 5490: 5434: 5395: 5338: 5284: 5050: 4986: 4887: 4825: 4773: 4699: 4621: 4550: 4498: 4496: 4494: 4492: 4490: 4488: 4486: 4484: 4482: 4480: 4466: 4389: 4346: 4282: 4178: 3940: 3799: 3780: 3637: 2824: 2753: 2749: 2666: 2613: 2546: 2535: 2358: 2299: 2286:, which is used in the synthesis of acetyl-CoA and other compounds. During 2263: 2177: 2041: 1758: 1546: 1537: 1364: 1288: 1284: 1250: 1185: 1046: 955: 833: 823:(HMB-Ca, CaHMB). Since only a small fraction of HMB's metabolic precursor, 651: 200: 7215: 6915: 6770: 5986: 5814: 5734: 5732: 4967: 4755: 1108:, or any other prominent national or international athletic organization. 928: 9487: 9444: 8837: 8817: 8812: 8772: 8314: 8219: 8208: 8203: 8181: 8171: 8104: 7864: 7508: 5653: 4844: 4561: 4423: 4421: 4419: 4417: 4415: 4413: 4411: 3882: • Nutravigor® (CaHMB, calcium β-hydroxy-β-methylbutyrate) 3823:"Product Information: Ensure Enlive Advanced Therapeutic Nutrition Shake" 3477: 3433: 2986: 2873: 2549: 2348: 2055: 1603: 1542: 1470: 1435: 1391: 1376: 1293: 1117: 1066: 872: 804: 737: 192: 6590: 5306: 5304: 5302: 5300: 5298: 4691: 4477: 4457: 4017: 1570:. HMB-FA is more readily absorbed into the bloodstream and has a longer 932: 859:), and is present in insignificant quantities in certain foods, such as 9672: 9462: 9186: 8908: 8862: 8664: 8659: 8549: 8522: 8508: 8433: 8358: 8338: 8308: 8270: 8188: 8161: 8154: 8134: 8127: 8015: 7897: 7788: 7619: 7604: 7585: 7484: 7479: 7474: 7373: 7261: 7240: 7113: 7095: 6639: 6538:

Kondakow J (1892). "On the action of mineral acids on dimethylallyls".

6361: 6359: 5756: 5729: 5472: 4860:

Fuller JC, Sharp RL, Angus HF, Khoo PY, Rathmacher JA (November 2015).

4328: 4169: 4152: 3326: 3159: 3104: 3002: 2982: 2958: 2698: 2501:{\displaystyle {\mathit {n}}_{\text{25°C}}^{\mathrm {\lambda =589nm} }} 2335:

to α-KIC and then HMB – is the predominant route of HMB synthesis.

2200: 2172: 2048: 2034: 1439: 1193: 1062: 916: 896: 876: 741: 691: 496: 333: 196: 188: 175: 8378: 6842: 5450: 5448: 5376: 5041: 5024: 4408: 1587: 1563: 1553: 1074: 1021: 975: 706:

from long-term use as a dietary supplement in adults have been found.

242: 221: 9214: 9093: 8923: 8872: 8802: 8777: 8717: 8669: 8654: 8649: 8602: 8597: 8592: 8587: 8503: 8458: 8343: 7688: 7504: 7469: 7402: 7388: 5738: 5295: 5022: 4306: 4304: 4302: 4300: 4298: 4296: 4054:

Experimental Boiling Point: ... 128 °C / 7 mm ...

3549: 2998: 2441: 1801: 1707: 1700: 1637:

of an ingested dose being excreted unchanged in urine. The remaining

1428: 1424: 988: 864: 796: 729: 308: 250: 6472: 6441: 6410: 6356: 5888: 5886: 5884: 4905: 4903: 4901: 4664:

Molfino A, Gioia G, Rossi Fanelli F, Muscaritoli M (December 2013).

4663: 1245: 1000:

during clinical trials in individuals with AIDS and cancer, but not

9874: 9779: 9728: 9705: 9615: 9428: 8757: 8737: 8674: 8634: 8619: 8513: 8117: 8028: 7863: 7744: 7731: 7678: 7500: 7464: 7455: 7359: 7320: 7136: 5506: 5504: 5445: 2795: 2413: 2006: 1721: 1656:

Biosynthesis and metabolism of β-hydroxy β-methylbutyrate in humans

1491: 1478: 1360: 1255: 1177: 979: 963: 940: 924: 667: 382: 5892: 4659: 4657: 4655: 4653: 4651: 4649: 4647: 4645: 4643: 4293: 3570:

At 150 minutes post-ingestion, a 2.42 gram dose of pure

2769: 519: 9751: 9523: 9436: 8903: 8857: 8787: 8767: 8614: 8488: 8478: 8224: 7935: 7917: 7889: 7868: 7436: 7355: 7334: 7325: 7244: 7230: 7176: 7094: 6896:

Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism

6628:

Monatshefte für Chemie und Verwandte Teile Anderer Wissenschaften

6299: 5881: 5351: 4898: 3615: 3584: 3311:

of HMB was published in 1877 by the Russian chemists Michael and

2686: 2652: 2319: 2204: 2080: 1822: 1771: 1714: 1670: 1630: 1408: 1348: 1321: 1197: 880: 868: 860: 745: 733: 725: 531: 184: 180: 6507:"Oxidation of Alkenes: Epoxidation, Hydroxylation, and Cleavage" 6307: 5501: 5227:"NCAA Study of Substance Use Habits of College Student-Athletes" 2066: 9574: 9556: 9410: 9297: 8898: 8762: 8684: 8679: 8639: 8629: 8624: 8567: 8558: 7541: 7339: 7122: 6399: 6295:"Showing metabocard for 3-Hydroxyisovaleric acid (HMDB0000754)" 5310: 5114: 5112: 4740:"Efficacy and Safety of Leucine Supplementation in the Elderly" 4640: 4366: 3349: 3029:

In a study where participants consumed 2.42 grams of pure

2701:

under basic conditions to yield the conjugate base of HMB. The

2690: 2590: 2419: 2407: 1869: 1617:) that is disproportionately greater than expected of a linear 1246:

peroxisome proliferator-activated receptor gamma coactivator-1α

967: 852: 717: 671: 663: 5968: 5792: 5790: 5788: 5510: 5195: 5193: 5160: 5158: 5018: 5016: 1541:

This graph shows the plasma concentration of HMB (in units of

5896:

Biochimica et Biophysica Acta (BBA) - Molecular Cell Research

5014: 5012: 5010: 5008: 5006: 5004: 5002: 5000: 4998: 4996: 4799: 4797: 4795: 4793: 4791: 4789: 4787: 2315: 1922: 1740: 1372: 1363:

via phosphorylation of mTORC1's immediate targets (i.e., the

1256:

eukaryotic translation initiation factor 4E-binding protein 1

856: 721: 510: 393: 255: 6226:"Homo sapiens: 4-hydroxyphenylpyruvate dioxygenase reaction" 5612: 5109: 4514: 4427: 3761: 3614:

Consumption of 3 grams of HMB-Ca with 75 grams of

2218:. In healthy individuals, approximately 60% of dietary 418: 9638: 9592: 8867: 8689: 8644: 6475:[Synthesis of some glycerol by hypochlorous acid]. 5785: 5190: 5155: 3757: 3755: 3753: 3751: 3749: 3747: 3745: 3743: 3741: 3739: 3737: 3735: 3733: 3731: 3729: 3727: 3725: 3723: 3721: 3719: 3717: 3715: 3713: 3711: 3709: 2597: 1514: 1510: 1499: 1487: 1100:

among athletes. As of 2018, HMB has not been banned by the

373: 6473:"Synthese einiger Glycerine mittelst unterchloriger Säure" 5702: 5700: 5454: 4993: 4784: 3707: 3705: 3703: 3701: 3699: 3697: 3695: 3693: 3691: 3689: 6576: 6158: 5560: 5357: 3005:. In the breast milk of healthy lactating women, HMB and 2445: 1416: 1412: 6321:. European Bioinformatics Institute. 16 September 2014. 5203:. National Collegiate Athletic Association. 10 June 2015 3768:

Journal of the International Society of Sports Nutrition

3665: 3663: 3329:

was by Tanaka and coworkers in 1968 from a patient with

1057:

through various mechanisms, including the activation of

694:. HMB produces these effects in part by stimulating the 6669:. New York: Oxford University Press. pp. 102–124. 6337: 5697: 5232:. National Collegiate Athletic Association. p. 7. 5224: 4112: 4110: 4108: 4106: 4104: 4102: 4100: 4098: 3686: 3583:

on muscle protein breakdown is entirely dependent upon

3052:

Abnormal HMB concentrations measured in disease states

709:

HMB is sold as a dietary supplement at a cost of about

595:

InChI=1S/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7)

6863: 6373:. European Bioinformatics Institute. 23 October 2015. 6096: 6094: 6092: 4592: 3571: 3532: 3519: 3030: 1559: 1133:

livestock have reported no adverse effects based upon

1082: 237: 216: 9839: 6172:. Technische Universität Braunschweig. Archived from 6108:

Nutrient Metabolism: Structures, Functions, and Genes

6090: 6088: 6086: 6084: 6082: 6080: 6078: 6076: 6074: 6072: 5317:

Journal of the American Medical Directors Association

4593:

Brioche T, Pagano AF, Py G, Chopard A (August 2016).

3660: 3353:

HMB-containing products, Juven and Revigor, to which

2464: 2227:

is metabolized after several hours, with roughly 5% (

1502:). HMB-induced human myosatellite cell proliferation 1297: • HMB: β-hydroxy β-methylbutyric acid 6964: 6962: 6960: 6958: 6893: 6823: 6821: 5848: 4948: 4859: 4214:. Abbott Laboratories. 12 March 2004. Archived from 4095: 3970:"Safety data sheet: 3-Hydroxy-3-methyl butyric acid" 3325:. The earliest reported isolation of HMB as a human 1649: 840: grams per day. HMB is sold at a cost of about 6784: 6782: 6780: 6621: 6619: 4003: 3604: 3602: 2790:HMB concentrations measured in healthy individuals 1554:

Comparison of pharmacokinetics between dosage forms

1120:of HMB in adult humans is based upon evidence from 6394: 6392: 6111:(2nd ed.). Academic Press. pp. 385–388. 6069: 5710:. Metabolic Technologies, Inc. 11 September 2014. 5220: 5218: 5074: 4949:Wilson GJ, Wilson JM, Manninen AH (January 2008). 3848: • HMB + protein for muscle health. 3817: 3815: 3813: 2717:; Diacetone alcohol is readily available from the 2500: 1016:A commercially available formulation of HMB. Each 7002:"Patents Assigned to Metabolic Technologies, Inc" 6955: 6818: 5029:Journal of Animal Physiology and Animal Nutrition 2556:. By extension, other structural analogs include 2199:HMB is synthesized in the human body through the 2187:or used in the production of cholesterol via the 1353:Tooltip mechanistic target of rapamycin complex 1 9887: 7011:As of March 2018, granted patents include: 6777: 6722: 6616: 6404: 6188: 5929: 5927: 5925: 4803: 4146: 4144: 3880: • Use under medical supervision. 3846: • Use under medical supervision. 3599: 3518:that were administered different daily doses of 3155: 2927: 2278:. Isovaleryl-CoA is subsequently metabolized by 1407:, HMB attenuates muscle protein breakdown in an 899:, and has been studied in clinical trials as an 658:and provide nutritional support for people with 321: 6723:Lee IY, Nissen SL, Rosazza JP (November 1997). 6413:[Synthesis of allyldimethylcarbinols]. 6389: 6218: 5964: 5962: 5960: 5215: 3810: 1506:is mediated through the phosphorylation of the 296: 8593:Ergocalciferol and Cholecalciferol (Vitamin D) 7333: 6552:Berichte der Deutschen Chemischen Gesellschaft 6291: 5563:Critical Reviews in Food Science and Nutrition 4202: 4200: 3999: 3997: 3995: 3993: 3991: 2985:(μM). The average concentration of HMB in the 2752:). Alternatively, HMB can be prepared through 2361:with the alpha, beta, and gamma carbons marked 1192:in response to physical exercise and specific 8964: 8950: 8394: 7849: 7080: 6933:. Boston, MA: Springer US. pp. 145–214. 5922: 5068: 5066: 5064: 4141: 3468: 3466: 3290:A indicates that the medical condition is a 2585:acid have been developed. The first reported 2126:or another uncharacterized enzyme, producing 759:. As of 2018, HMB has not been banned by the 5957: 5616:Journal of the American College of Nutrition 5262: 4259: 4029: 4027: 2906: 2262:(α-KIC). α-KIC is mostly metabolized by the 996:per two servings, has been shown to improve 6887: 6827: 6788: 6716: 6470: 5517:Journal of Parenteral and Enteral Nutrition 4737: 4197: 3988: 2848: 2784: 2697:or 4,4-dimethyloxetan-2-one, both of which 1521:is mediated through the phosphorylation of 1261:eukaryotic translation initiation factor 4E 8957: 8943: 8401: 8387: 7856: 7842: 7087: 7073: 6831:Journal of Agricultural and Food Chemistry 6792:Journal of Agricultural and Food Chemistry 6660: 6439: 6402:chemical database as of September 2016 is: 5461:Journal of Cachexia, Sarcopenia and Muscle 5072: 5061: 4944: 4942: 4317:Journal of Cachexia, Sarcopenia and Muscle 4119:"Proteins in Human Health and Performance" 4063: 3964: 3962: 3463: 3386:Synonyms and alternate spellings include: 2681:Depending on the experimental conditions, 2254:branched-chain amino acid aminotransferase 1438:, which may then be incorporated into the 1301: • Τ represents inhibition 455: 432: 341: 56: 47: 7057:at the U.S. National Library of Medicine 6760: 6100: 5994: 5822: 5764: 5528: 5480: 5385: 5375: 5328: 5040: 4976: 4966: 4877: 4763: 4681: 4540: 4456: 4336: 4168: 4024: 3789: 3779: 3636:This reaction is catalyzed by an unknown 2252:metabolism is initially catalyzed by the 1299: • ↑ represents activation 1059:mechanistic target of rapamycin complex 1 361: 6692:"Homolytic Mechanism in Metal Catalysis" 6579:Journal of the American Chemical Society 6537: 6371:Chemical Entities of Biological Interest 6343: 6319:Chemical Entities of Biological Interest 6287: 6285: 6283: 6281: 6279: 6277: 6275: 6273: 6271: 6269: 6267: 5796: 5663:Journal of Science and Medicine in Sport 5225:The NCAA Research Staff (January 2006). 5129:(2nd ed.). CRC Press. p. 724. 4006:Journal of the American Chemical Society 2768: 2665: 1610:, resulting in a peak plasma HMB level ( 1536: 1527:serine/threonine-specific protein kinase 1102:National Collegiate Athletic Association 1011: 1007: 761:National Collegiate Athletic Association 8408: 6549: 6501: 6265: 6263: 6261: 6259: 6257: 6255: 6253: 6251: 6249: 6247: 6200:Kyoto Encyclopedia of Genes and Genomes 5939:Kyoto Encyclopedia of Genes and Genomes 5440:setting of muscle wasting is warranted. 4939: 4310: 4121:. Iowa State University. Archived from 3959: 3476:of muscle damage or protein breakdown: 2967:liquid chromatography–mass spectrometry 2963:nuclear magnetic resonance spectroscopy 1581: 907:. Based upon two medical reviews and a 428: 14: 9888: 6975:. University of Iowa. pp. 13–16. 6928: 6733:Applied and Environmental Microbiology 5412: 4263:Archives of Gerontology and Geriatrics 4150: 3976:from the original on 17 September 2016 2608:in 1877, Russian chemists Michael and 2158:), which is subsequently converted to 2039: 2032: 2025: 2018: 2011: 2004: 1986: 1977: 1959: 1950: 1941: 1934: 1919: 1908: 1898: 1887: 1877: 1867: 1857: 1847: 1838: 1829: 1820: 1813: 1777: 1750: 1624: 646:substance in humans that is used as a 446: 154: 8938: 8382: 7837: 7282:2-Amino-3-carboxymuconic semialdehyde 7068: 6982:from the original on 1 September 2016 6689: 6683: 6411:"Synthese des Allyldimethylcarbinols" 5265:Current Protein & Peptide Science 5118: 4920:. Abbott Laboratories. Archived from 3596:and carbohydrates is ~50% on average. 3287: 3068: 3065: 3062: 3059: 3056: 2981:of HMB has been measured at 4.0 2977:(CSF) of healthy adults, the average 2805: 2802: 2799: 2794: 2511: 2053: 2046: 1995: 1968: 1784: 1764: 1738: 1719: 1712: 1705: 1698: 1691: 1423:in skeletal muscle and by inhibiting 401: 145: 7595:2,3-Dihydroxy-3-methylpentanoic acid 6625: 6325:from the original on 1 December 2017 6244: 5178:from the original on 22 October 2017 4738:Borack MS, Volpi E (December 2016). 4116: 4080:from the original on 6 February 2018 4040:. Royal Society of Chemistry. 2015. 3867:from the original on 12 October 2016 3835:from the original on 12 October 2016 3315:. HMB was isolated from the bark of 3169:3-Methylglutaconic aciduria (Type I) 2971:gas chromatography–mass spectrometry 2122:). HMB-CoA is metabolized by either 1799: 1726: 1682: 1668: 1461:HMB has been shown to stimulate the 1346:(mTOR) and subsequent activation of 556:128 °C (262 °F) at 7 6712:from the original on 22 March 2018. 6232:. SRI International. 20 August 2012 5714:from the original on 26 August 2016 4044:from the original on 11 August 2016 3828:. Abbott Nutrition. 9 August 2016. 2324:4-hydroxyphenylpyruvate dioxygenase 1532: 1310: 381: 312: 62:Top: β-Hydroxy β-methylbutyric acid 24: 6698:. New York: Elsevier. p. 67. 6415:Justus Liebig's Annalen der Chemie 6377:from the original on 12 March 2016 6125:from the original on 22 March 2018 5143:from the original on 22 March 2018 5121:"Beta-Hydroxy beta-methylbutyrate" 3647: 3609: 3531:Approximately equal doses of pure 3460:, was approximately 6 months. 3344:. Nissen founded a company called 3105: 3034: 2838: 2492: 2489: 2468: 1092:In 2006, only about 2% of college 891:Supplemental HMB has been used in 783: 546:−80 °C (−112 °F) (glass) 64:Bottom: β-Hydroxy β-methylbutyrate 25: 9967: 7048: 6511:Fundamentals of Organic Chemistry 6471:Reformatzky B (30 October 1889). 5277:10.2174/1389203718666170529105026 3452:and 140 older adults in the 2973:methods. In the blood plasma and 2655:4-methylpentane-1,2,4-triol is a 2578:A variety of synthetic routes to 1562:) and monohydrated calcium salt ( 1508:mitogen-activated protein kinases 1385:insulin-like growth factor 1 1211:Abbreviations and representations 1089: minutes prior to exercise. 1081: hours prior to exercise or 9873: 9861: 9849: 6753:10.1128/AEM.63.11.4191-4195.1997 6300:Human Metabolome Database, HMDB 6206:from the original on 1 July 2016 6136:fatty acids, and other compounds 5945:from the original on 1 July 2016 5239:from the original on 10 May 2016 5201:"2018–19 NCAA Banned Drugs List" 5166:"Prohibited List (January 2018)" 4866:The British Journal of Nutrition 3860:. Abbott Nutrition. 7 May 2016. 3014:have been measured in ranges of 2368: 2347: 2146:is then converted by the enzyme 2065: 1660: 1196:or their derivatives (primarily 1169: 1143:no-observed-adverse-effect level 1043:high-intensity interval training 650:and as an ingredient in certain 480: 9195:adenosine triphosphate disodium 7417:Imidazol-4-one-5-propionic acid 6994: 6922: 6857: 6661:Doraiswamy LK (February 2001). 6654: 6597: 6570: 6531: 6495: 6464: 6433: 4070:"beta-Hydroxyisovaleric acid". 3669: 3654: 3630: 3621: 3564: 3525: 3508: 3321:(a Madagascan tree) in 1941 by 3217:Gastroesophageal reflux disease 2589:approached HMB by oxidation of 2194: 1344:mechanistic target of rapamycin 1226:mechanistic target of rapamycin 1160: 1111: 851:(e.g., certain formulations of 600:Key:AXFYFNCPONWUHW-UHFFFAOYSA-N 279:3-hydroxy-3-methylbutanoic acid 9896:Drugs not assigned an ATC code 7231:β-Hydroxy β-methylglutaryl-CoA 7186:β-Hydroxy β-methylbutyric acid 5415:Nutrition in Clinical Practice 3380: 3044:, particularly in the case of 2377:β-hydroxy β-methylbutyric acid 2290:, HMB can be synthesized from 2164:methylglutaconyl-CoA hydratase 2148:methylcrotonyl-CoA carboxylase 1823:β-Hydroxy β-methylglutaryl-CoA 1566:) forms of HMB have different 1450:(i.e., muscle enzymes such as 1271:eukaryotic elongation factor 2 939:disease states such as cancer 801:β-hydroxy β-methylbutyric acid 623:β-Hydroxy β-methylbutyric acid 486: 474: 42:β-Hydroxy β-methylbutyric acid 13: 1: 7446:1-Pyrroline-5-carboxylic acid 7191:β-Hydroxy β-methylbutyryl-CoA 6667:Organic Synthesis Engineering 6605:WO application 2012140276 6477:Journal für Praktische Chemie 6446:Journal für Praktische Chemie 6440:Schirokoff A (January 1881). 6345:WO application 2015094925 5628:10.1080/07315724.2018.1451789 4602:Molecular Aspects of Medicine 4275:10.1016/j.archger.2015.06.020 3972:. Alfa Aesar. 23 March 2005. 3679: 3458:weighted by their sample size 3265:MC-CoA carboxylase deficiency 3001:per millimole (μmol/mmol) of 2725:approach to HMB involves the 2090:. Of the two major pathways, 1644: 1431:via unidentified mechanisms. 1188:muscle protein synthesis and 1024:and an unspecified amount of 1018:size 000 gelatin capsule 654:that are intended to promote 9311:Glucose with sodium chloride 8006:Geranylgeranyl pyrophosphate 7576:2-Methyl-3-oxopropanoic acid 6931:Biology of Brain Dysfunction 6908:10.1016/0005-2760(68)90107-0 5908:10.1016/j.bbamcr.2008.12.017 5575:10.1080/10408398.2012.708368 5171:. World Anti-Doping Agency. 4533:10.1113/jphysiol.2013.253203 4449:10.1016/j.nutres.2017.07.008 3855:"Product Information: Juven" 3444:95% confidence interval 3346:Metabolic Technologies, Inc. 2639:oxidises alkenes to vicinal 2573: 2426:. At room temperature, pure 2338: 2280:isovaleryl-CoA dehydrogenase 1602:in the gut. When the HMB-Ca 1241:AMP-activated protein kinase 1155:Metabolic Technologies, Inc. 913:randomized controlled trials 536:~1.1 g/cm at 20 °C 7: 7985:Dimethylallyl pyrophosphate 7754:4-Hydroxyphenylpyruvic acid 7287:2-Aminomuconic semialdehyde 7055:Beta-Hydroxyisovaleric acid 6939:10.1007/978-1-4684-2673-1_3 6141:Figure 8.57: Metabolism of 5675:10.1016/j.jsams.2017.11.003 5330:10.1016/j.jamda.2016.04.019 4911:"Abbott Nutrition Overview" 3361: 2853:Tooltip cerebrospinal fluid 1484:myogenic regulatory factors 1421:ubiquitin–proteasome system 1061:(mTORC1) and inhibition of 674:size, muscle strength, and 10: 9972: 8994:β-hydroxy-β-methylbutyrate 8713:β-hydroxy β-methylbutyrate 8603:Naphthoquinone (Vitamin K) 7630:generation of homocysteine 6690:Kochi JK (December 2012). 6367:"3-hydroxyisovaleric acid" 5863:10.1016/j.phrs.2015.05.010 5708:"Who should not take HMB?" 4955:Nutrition & Metabolism 3405:3-hydroxy-3-methylbutanoic 3302: 2773:Later synthetic routes to 2670:First synthetic routes to 2643:-diols which hot acid KMnO 1629:HMB is eliminated via the 1619:dose-response relationship 1592:β-hydroxy β-methylbutyrate 1315:Several components of the 1244: • PGC‐1α: 1026:microcrystalline cellulose 886: 819:β-hydroxy β-methylbutyrate 629:), otherwise known as its 464:Chemical and physical data 31: 9800: 9778: 9750: 9727: 9704: 9695: 9637: 9614: 9591: 9573: 9555: 9546: 9409: 9296: 9213: 9185: 9092: 8984: 8977: 8886: 8698: 8588:Ascorbic acid (Vitamin C) 8487: 8416: 8328: 8268: 8261: 8217: 8102: 8050: 8041: 8014: 7993: 7980:Isopentenyl pyrophosphate 7975:5-Diphosphomevalonic acid 7954: 7926: 7887: 7878: 7809: 7802: 7776: 7739: 7729: 7706: 7687: 7618: 7584: 7540: 7525: 7493: 7454: 7435: 7401: 7386: 7318: 7309: 7277:3-Hydroxyanthranilic acid 7239: 7175: 7121: 7108: 6881:10.1002/hlca.194102401171 6517:. pp. 124–126, 142. 6202:. Kanehisa Laboratories. 6043:10.1007/s00726-010-0678-0 5941:. Kanehisa Laboratories. 5797:Phillips SM (July 2015). 5081:. Pegasus Books. p. 5073:Fitzgerald M (May 2014). 4879:10.1017/S0007114515003050 4818:10.1007/s40279-015-0308-9 4683:10.1007/s00726-013-1592-z 4614:10.1016/j.mam.2016.04.006 4521:The Journal of Physiology 4382:10.1007/s40266-017-0496-0 4311:Holeček M (August 2017). 3933:10.1007/s00726-010-0678-0 3281:μmol/mmol creatinine 3257:μmol/mmol creatinine 3233:μmol/mmol creatinine 3209:μmol/mmol creatinine 3185:μmol/mmol creatinine 3081: 3078: 3075: 2949:μmol/mmol creatinine 2818: 2815: 2812: 2216:branched-chain amino acid 2136:hydroxymethylglutaryl-CoA 1753:Branched-chain α-ketoacid 1259: • eIF4E: 1254: • 4EBP1: 608: 583: 563: 550: 540: 530: 508: 495: 468: 463: 444: 412: 392: 372: 352: 332: 307: 287: 267: 262: 249: 228: 210: 174: 166: 135: 130: 114: 96: 74: 69: 55: 46: 9911:Bodybuilding supplements 7764:4-Maleylacetoacetic acid 7571:3-Hydroxyisobutyric acid 7427:Glutamate-1-semialdehyde 7059:Medical Subject Headings 6804:10.1021/acs.jafc.5b02563 6564:10.1002/cber.18930260412 6489:10.1002/prac.18890400137 6458:10.1002/prac.18810230115 6427:10.1002/jlac.18771850204 6101:Kohlmeier M (May 2015). 5975:The Journal of Nutrition 5851:Pharmacological Research 5530:10.1177/0148607113502545 5427:10.1177/0884533613516130 4744:The Journal of Nutrition 4153:"Rethinking the formula" 4056:Experimental solubility: 4034:"3-OH-isovaleric acid". 3373: 3241:HMG-CoA lyase deficiency 3193:Eosinophilic esophagitis 2785:Detection in body fluids 2522:acid is a member of the 2240:being converted to HMB. 2231: range) of dietary 1269: • eEF2: 1264: • RPS6: 1249: • S6K1: 1239: • AMPK: 1224: • mTOR: 1190:mitochondrial biogenesis 1106:World Anti-Doping Agency 1020:contains 1 gram of 765:World Anti-Doping Agency 150: Dietary supplement 85:3-hydroxyisovaleric acid 83:β-hydroxyisovaleric acid 32:Not to be confused with 9951:Rehabilitation medicine 8424:Bodybuilding supplement 8194:Cholesta-7,24-dien-3-ol 8145:4alpha-Methylzymosterol 8024:Prephytoene diphosphate 7872:metabolic intermediates 7610:2-Methylacetoacetyl-CoA 7566:3-Hydroxyisobutyryl-CoA 7102:metabolic intermediates 6196:"KEGG Reaction: R04137" 5935:"KEGG Reaction: R10759" 5119:Rippe JM (March 2013). 2989:of healthy men of ages 2274:, which converts it to 1283: • Myo: 1234: • ATP: 1231:adenosine monophosphate 1229: • AMP: 1214: • PLD: 987:, and 14 grams of 778: 692:age-related muscle loss 9901:Amino acid derivatives 8598:Tocopherol (Vitamin E) 8113:Farnesyl pyrophosphate 8043:Non-mevalonate pathway 7819:Cysteine sulfinic acid 7665:conversion to cysteine 7422:Formiminoglutamic acid 7349:3-Phosphoglyceric acid 7226:β-Methylglutaconyl-CoA 6869:Helvetica Chimica Acta 6315:"3-hydroxyisovalerate" 4117:Linn J (13 May 2013). 3781:10.1186/1550-2783-10-6 3535:(2.42 grams) and 3368:3-Aminoisobutyric acid 3318:Erythrophleum couminga 3140:Biotinidase deficiency 3118:Biotinidase deficiency 3088:Biotinidase deficiency 2781: 2678: 2629:potassium permanganate 2502: 2302:enzyme, which convert 1841:β-Methylglutaconyl-CoA 1550: 1429:skeletal muscle nuclei 1292: • AA: 1274: • RE: 1236:adenosine triphosphate 1219: • PA: 1053:and inhibiting muscle 1033: 775:among young athletes. 696:production of proteins 9941:Proteasome inhibitors 9471:methylsulfonylmethane 8246:-Dihydroxycholesterol 8140:14-demethyllanosterol 8001:Geranyl pyrophosphate 7970:Phosphomevalonic acid 7946:β-Hydroxybutyric acid 7551:α-Ketoisovaleric acid 7206:β-Ketoisocaproic acid 7201:α-Ketoisocaproic acid 6152:22 March 2018 at the 5987:10.3945/jn.111.146126 5815:10.3945/an.115.008367 5803:Advances in Nutrition 4968:10.1186/1743-7075-5-1 4756:10.3945/jn.116.230771 4151:Khamsi R (May 2013). 3550:myofibrillar proteins 3499:long-distance running 3485:lactate dehydrogenase 3338:Iowa State University 2772: 2669: 2503: 2243:The vast majority of 2170:is then cleaved into 1687:acid aminotransferase 1572:elimination half-life 1540: 1496:transcription factors 1456:lactate dehydrogenase 1184:that are involved in 1139:human equivalent dose 1069:in skeletal muscles. 1015: 1008:Enhancing performance 753:Iowa State University 702:in muscle tissue. No 700:breakdown of proteins 92:hydroxymethylbutyrate 34:β-Hydroxybutyric acid 9509:-adenosyl methionine 9205:monosodium phosphate 8798:Japanese honeysuckle 8304:24-Methylenelophenol 8199:7-Dehydrodesmosterol 8177:7-Dehydrocholesterol 7638:-Adenosyl methionine 7221:β-Methylcrotonyl-CoA 7211:β-Ketoisocaproyl-CoA 7167:β-Hydroxybutyryl-CoA 6727:Galactomyces reessii 6166:"Leucine metabolism" 3546:fractional synthesis 3503:progressive overload 3042:diagnostic biomarker 2763:Galactomyces reessii 2462: 2152:methylglutaconyl-CoA 2128:β-methylcrotonyl-CoA 1832:β-Methylcrotonyl-CoA 1685:Branched-chain amino 1582:Absorption of HMB-Ca 1440:muscle cell membrane 1357:protein biosynthesis 1266:ribosomal protein S6 1098:ergogenic supplement 903:in conjunction with 773:ergogenic supplement 219:: 30–60 minutes 9916:Dietary supplements 9742:monofluorophosphate 9252:+hydrogen carbonate 8966:Mineral supplements 8723:Chondroitin sulfate 8541:Pantothenic acid (B 8504:Retinol (Vitamin A) 8474:Protein supplements 8410:Dietary supplements 8294:4α-methylfecosterol 8237:-Hydroxycholesterol 7811:Cysteine metabolism 7600:2-Methylbutyryl-CoA 7292:2-Aminomuconic acid 7272:3-Hydroxykynurenine 6745:1997ApEnM..63.4191L 6591:10.1021/ja01631a045 4927:on 3 September 2016 4750:(12): 2625S–2629S. 4218:on 20 December 2016 4018:10.1021/ja01544a072 3516:Sprague-Dawley rats 3416:3-hydroxyisovaleric 3331:isovaleric acidemia 3307:The first reported 3053: 3046:metabolic disorders 2987:intramuscular fluid 2979:molar concentration 2975:cerebrospinal fluid 2791: 2760:acid by the fungus 2754:microbial oxidation 2715:sodium hypochlorite 2651:. In other words, 2497: 2296:enoyl-CoA hydratase 2124:enoyl-CoA hydratase 2115:β-methylbutyryl-CoA 1937:Enoyl-CoA hydratase 1625:Excretion of HMB-Ca 1327:metabolic precursor 1325:. Similar to HMB's 1276:resistance exercise 1041:when combined with 1002:rheumatoid cachexia 978:, 14 grams of 905:resistance exercise 849:Abbott Laboratories 803:(HMB-FA), and as a 698:and inhibiting the 43: 9956:Muscular disorders 9931:Beta hydroxy acids 9827:Never to phase III 9519:Sodium thiosulfate 9351:hydrogen carbonate 8894:Codex Alimentarius 8783:Grape seed extract 8444:Herbal supplements 7880:Mevalonate pathway 7698:α-Ketobutyric acid 7675:α-Ketobutyric acid 7513:γ-Glutamylcysteine 7257:′-Formylkynurenine 7142:α-Aminoadipic acid 6731:. primary source. 6640:10.1007/BF01526057 5973:. primary source. 5757:10.1111/apha.12532 5473:10.1002/jcsm.12127 5126:Lifestyle Medicine 4864:. primary source. 4437:Nutrition Research 4329:10.1002/jcsm.12208 4170:10.1038/nm0513-525 3426:-hydroxyisovaleric 3309:chemical synthesis 3292:metabolic disorder 3110:Tooltip micromolar 3057:Medical condition 3051: 2789: 2782: 2719:aldol condensation 2711:sodium hypobromite 2695:β-isovalerolactone 2679: 2587:chemical syntheses 2512:Chemical structure 2498: 2465: 2256:enzyme, producing 2189:mevalonate pathway 1551: 1475:myosatellite cells 1444:protein metabolism 1371:repressor protein 1280:endurance exercise 1182:signaling cascades 1135:clinical chemistry 1034: 1030:magnesium stearate 793:dietary supplement 788:HMB is sold as an 648:dietary supplement 644:naturally produced 41: 9926:Human metabolites 9837: 9836: 9796: 9795: 9691: 9690: 9662: 9654: 9542: 9541: 9501:protamine sulfate 9496:potassium sulfate 9482: 9465: 9447: 9439: 9431: 9054:lactate gluconate 9049:glycerylphosphate 8932: 8931: 8577:Cyanocobalamin (B 8494:chemical elements 8376: 8375: 8372: 8371: 8123:2,3-Oxidosqualene 8098: 8097: 8037: 8036: 7831: 7830: 7827: 7826: 7798: 7797: 7772: 7771: 7759:Homogentisic acid 7725: 7724: 7717:Methylmalonyl-CoA 7521: 7520: 7382: 7381: 7305: 7304: 6948:978-1-4684-2675-5 6843:10.1021/jf500026s 6798:(34): 7567–7573. 6739:(11): 4191–4195. 6705:978-0-323-14410-0 6676:978-0-19-509689-7 6524:978-1-4390-4971-6 6176:on 17 August 2016 6118:978-0-12-387784-0 5981:(11): 1925–1930. 5745:Acta Physiologica 5569:(13): 1793–1807. 5377:10.3390/nu8050295 5136:978-1-4398-4544-8 5092:978-1-60598-595-4 5042:10.1111/jpn.12234 4527:(11): 2911–2923. 4370:Drugs & Aging 4125:on 27 August 2016 4012:(11): 2882–2887. 3494:3-methylhistidine 3313:Alexander Zaytsev 3300: 3299: 3296: 3071: 2955: 2954: 2808: 2746:hydrogen peroxide 2707:diacetone alcohol 2703:haloform reaction 2610:Alexander Zaytsev 2532:structural analog 2528:organic compounds 2476: 2404:molecular formula 2288:biotin deficiency 2282:and converted to 2259:α-ketoisocaproate 2106: 2105: 2073:metabolic pathway 2021:β-Hydroxybutyrate 1989:β-Hydroxybutyrate 1745:α-Ketoisocaproate 1733:α-Ketoisocaproate 1586:After ingestion, 1379:concentration of 1355:, which leads to 1317:signaling cascade 1221:phosphatidic acid 1055:protein breakdown 1051:protein synthesis 945:high-protein diet 620: 619: 521:Interactive image 414:CompTox Dashboard 258:(10–40% excreted) 205:β-hydroxybutyrate 159: Unscheduled 158: 149: 27:Chemical compound 16:(Redirected from 9963: 9878: 9877: 9866: 9865: 9864: 9854: 9853: 9852: 9845: 9714:(III) picolinate 9702: 9701: 9660: 9652: 9583:potassium iodide 9553: 9552: 9480: 9463: 9453:Iron(II) sulfate 9445: 9437: 9429: 9019:+cholecalciferol 8982: 8981: 8959: 8952: 8945: 8936: 8935: 8887:Related articles 8793:Iron supplements 8733:Copper gluconate 8403: 8396: 8389: 8380: 8379: 8354:Ergostatetraenol 8266: 8265: 8225:Steroid hormones 8048: 8047: 7941:Acetoacetic acid 7885: 7884: 7858: 7851: 7844: 7835: 7834: 7807: 7806: 7737: 7736: 7651: 7650: 7538: 7537: 7399: 7398: 7331: 7330: 7316: 7315: 7267:Anthranilic acid 7147:2-Oxoadipic acid 7119: 7118: 7089: 7082: 7075: 7066: 7065: 7042: 7040: 7034: 7028: 7022: 7016: 7009: 6998: 6992: 6991: 6989: 6987: 6981: 6974: 6966: 6953: 6952: 6926: 6920: 6919: 6891: 6885: 6884: 6875:(1): 1449–1458. 6861: 6855: 6854: 6837:(7): 1506–1511. 6825: 6816: 6815: 6786: 6775: 6774: 6764: 6720: 6714: 6713: 6687: 6681: 6680: 6658: 6652: 6651: 6623: 6614: 6613: 6612: 6608: 6601: 6595: 6594: 6574: 6568: 6567: 6547: 6535: 6529: 6528: 6515:Cengage Learning 6513:(7th ed.). 6499: 6493: 6492: 6468: 6462: 6461: 6437: 6431: 6430: 6421:(2–3): 151–169. 6396: 6387: 6386: 6384: 6382: 6363: 6354: 6353: 6352: 6348: 6341: 6335: 6334: 6332: 6330: 6311: 6305: 6304: 6289: 6242: 6241: 6239: 6237: 6222: 6216: 6215: 6213: 6211: 6192: 6186: 6185: 6183: 6181: 6162: 6156: 6146: 6145: 6138: 6132: 6130: 6098: 6067: 6066: 6037:(4): 1015–1025. 6022: 6013: 6012: 5998: 5966: 5955: 5954: 5952: 5950: 5931: 5920: 5919: 5890: 5879: 5878: 5846: 5837: 5836: 5826: 5794: 5783: 5782: 5768: 5736: 5727: 5726: 5721: 5719: 5704: 5695: 5694: 5657: 5651: 5650: 5610: 5599: 5598: 5558: 5547: 5546: 5532: 5508: 5499: 5498: 5484: 5452: 5443: 5442: 5410: 5404: 5403: 5389: 5379: 5355: 5349: 5348: 5332: 5308: 5293: 5292: 5260: 5249: 5248: 5246: 5244: 5238: 5231: 5222: 5213: 5212: 5210: 5208: 5197: 5188: 5187: 5185: 5183: 5177: 5170: 5162: 5153: 5152: 5150: 5148: 5116: 5107: 5106: 5101: 5099: 5080: 5070: 5059: 5058: 5044: 5020: 4991: 4990: 4980: 4970: 4946: 4937: 4936: 4934: 4932: 4926: 4915: 4907: 4896: 4895: 4881: 4872:(9): 1403–1409. 4857: 4842: 4841: 4801: 4782: 4781: 4767: 4735: 4716: 4715: 4685: 4676:(6): 1273–1292. 4661: 4638: 4637: 4599: 4590: 4559: 4558: 4544: 4512: 4475: 4474: 4460: 4434: 4425: 4406: 4405: 4364: 4355: 4354: 4340: 4308: 4291: 4290: 4257: 4228: 4227: 4225: 4223: 4204: 4195: 4194: 4172: 4148: 4139: 4138: 4132: 4130: 4114: 4093: 4092: 4087: 4085: 4073:PubChem Compound 4067: 4061: 4060: 4058:Soluble in water 4051: 4049: 4031: 4022: 4021: 4001: 3986: 3985: 3983: 3981: 3966: 3957: 3956: 3927:(4): 1015–1025. 3912: 3885: 3884: 3874: 3872: 3866: 3859: 3850: 3842: 3840: 3834: 3827: 3819: 3808: 3807: 3793: 3783: 3759: 3673: 3667: 3658: 3641: 3634: 3628: 3625: 3619: 3611: 3606: 3597: 3595: 3593: 3592: 3582: 3580: 3579: 3573: 3568: 3562: 3560: 3558: 3557: 3543: 3541: 3540: 3534: 3529: 3523: 3521: 3512: 3506: 3496: 3470: 3461: 3450:treatment groups 3440: 3431: 3427: 3417: 3406: 3399: 3393: 3384: 3355:Abbott Nutrition 3343: 3295: 3288: 3157: 3111: 3107: 3069: 3054: 3050: 3036: 3032: 3025: 3021: 3017: 3013: 3011: 3010: 2996: 2992: 2930: creatinine 2929: 2908: 2854: 2850: 2840: 2806: 2792: 2788: 2779: 2776: 2759: 2742:Fenton's reagent 2696: 2693:produces either 2676: 2673: 2649:alkene oxidation 2584: 2581: 2567: 2560: 2559:β-hydroxybutyric 2543:functional group 2521: 2518: 2507: 2505: 2504: 2499: 2496: 2495: 2477: 2474: 2472: 2471: 2456:refractive index 2439: 2436: 2432: 2429: 2425: 2390: 2387: 2378: 2372: 2355:Skeletal formula 2351: 2334: 2332: 2331: 2313: 2309: 2305: 2293: 2285: 2271: 2261: 2251: 2249: 2248: 2239: 2237: 2236: 2230: 2226: 2224: 2223: 2212: 2210: 2209: 2184: 2175: 2169: 2161: 2157: 2145: 2142:) respectively. 2141: 2133: 2121: 2116: 2113: 2098: 2096: 2095: 2088: 2086: 2085: 2069: 2068: 2058: 2051: 2044: 2037: 2030: 2023: 2016: 2009: 2002: 1993: 1984: 1975: 1966: 1957: 1948: 1939: 1932: 1917: 1906: 1896: 1885: 1875: 1865: 1855: 1845: 1836: 1827: 1818: 1808: 1797: 1789:β-methylbutyrate 1782: 1775: 1762: 1748: 1736: 1724: 1717: 1710: 1703: 1696: 1689: 1680: 1678: 1676: 1675: 1664: 1650: 1640: 1636: 1593: 1590:is converted to 1589: 1577: 1568:pharmacokinetics 1565: 1561: 1533:Pharmacokinetics 1419:subunits of the 1406: 1404: 1403: 1354: 1350: 1337: 1335: 1334: 1311:Pharmacodynamics 1205: 1203: 1202: 1173: 1128:. In humans, no 1094:student athletes 1088: 1084: 1080: 1076: 1023: 993: 992: 984: 983: 977: 846: 839: 831: 829: 828: 820: 790:over-the-counter 769:student athletes 758: 715: 640: 639:β-methylbutyrate 637: 616: 615: 523: 503: 488: 482: 476: 459: 448: 437: 436: 422: 420: 405: 385: 365: 345: 325: 315: 314: 300: 245:: 2.5 hours 244: 239: 233: 224:: 1–2 hours 223: 218: 156: 153: 147: 144: 60: 51: 44: 40: 21: 9971: 9970: 9966: 9965: 9964: 9962: 9961: 9960: 9886: 9885: 9884: 9872: 9862: 9860: 9850: 9848: 9840: 9838: 9833: 9832: 9817:Clinical trials 9792: 9774: 9746: 9723: 9687: 9633: 9610: 9587: 9569: 9538: 9424:Calcium sulfate 9405: 9326:calcium edetate 9306:Docusate sodium 9292: 9209: 9181: 9088: 8973: 8963: 8933: 8928: 8882: 8700: 8694: 8580: 8571: 8562: 8553: 8544: 8535: 8526: 8517: 8495: 8492: 8483: 8468:Bifidobacterium 8412: 8407: 8377: 8368: 8324: 8257: 8222: 8213: 8094: 8033: 8010: 7989: 7950: 7922: 7903:Acetoacetyl-CoA 7874: 7862: 7832: 7823: 7794: 7768: 7721: 7702: 7683: 7648: 7647: 7614: 7580: 7561:Methacrylyl-CoA 7531: 7517: 7489: 7450: 7431: 7394:α-ketoglutarate 7392: 7378: 7369:Phosphocreatine 7338: 7324: 7301: 7235: 7171: 7104: 7093: 7051: 7046: 7045: 7036: 7030: 7024: 7018: 7012: 7010: 7000: 6999: 6995: 6985: 6983: 6979: 6972: 6968: 6967: 6956: 6949: 6927: 6923: 6892: 6888: 6862: 6858: 6826: 6819: 6787: 6778: 6721: 6717: 6706: 6688: 6684: 6677: 6659: 6655: 6624: 6617: 6610: 6602: 6598: 6575: 6571: 6536: 6532: 6525: 6500: 6496: 6469: 6465: 6438: 6434: 6403: 6397: 6390: 6380: 6378: 6365: 6364: 6357: 6350: 6342: 6338: 6328: 6326: 6313: 6312: 6308: 6290: 6245: 6235: 6233: 6224: 6223: 6219: 6209: 6207: 6194: 6193: 6189: 6179: 6177: 6164: 6163: 6159: 6154:Wayback Machine 6143: 6142: 6139: 6128: 6126: 6119: 6099: 6070: 6023: 6016: 5967: 5958: 5948: 5946: 5933: 5932: 5923: 5891: 5882: 5847: 5840: 5795: 5786: 5737: 5730: 5717: 5715: 5706: 5705: 5698: 5658: 5654: 5611: 5602: 5559: 5550: 5509: 5502: 5453: 5446: 5411: 5407: 5356: 5352: 5345: 5309: 5296: 5261: 5252: 5242: 5240: 5236: 5229: 5223: 5216: 5206: 5204: 5199: 5198: 5191: 5181: 5179: 5175: 5168: 5164: 5163: 5156: 5146: 5144: 5137: 5117: 5110: 5097: 5095: 5093: 5071: 5062: 5021: 4994: 4947: 4940: 4930: 4928: 4924: 4913: 4909: 4908: 4899: 4858: 4845: 4806:Sports Medicine 4802: 4785: 4736: 4719: 4662: 4641: 4597: 4591: 4562: 4513: 4478: 4432: 4426: 4409: 4376:(11): 833–840. 4365: 4358: 4309: 4294: 4258: 4231: 4221: 4219: 4206: 4205: 4198: 4157:Nature Medicine 4149: 4142: 4128: 4126: 4115: 4096: 4083: 4081: 4069: 4068: 4064: 4057: 4055: 4047: 4045: 4033: 4032: 4025: 4002: 3989: 3979: 3977: 3968: 3967: 3960: 3913: 3888: 3881: 3879: 3877: 3870: 3868: 3864: 3857: 3853: 3852: 3851: 3847: 3845: 3838: 3836: 3832: 3825: 3821: 3820: 3811: 3760: 3687: 3682: 3677: 3676: 3670: 3661: 3655: 3650: 3648:Reference notes 3645: 3644: 3635: 3631: 3626: 3622: 3613: 3607: 3600: 3590: 3589: 3588: 3577: 3576: 3575: 3569: 3565: 3555: 3554: 3553: 3538: 3537: 3536: 3530: 3526: 3513: 3509: 3492: 3481:creatine kinase 3471: 3464: 3447: 3441: 3434: 3422: 3415: 3404: 3394: 3388: 3385: 3381: 3376: 3364: 3341: 3323:Leopold Ružička 3305: 3289: 3272:Children (1–13) 3248:Children (1–13) 3224:Children (1–13) 3200:Children (1–13) 3176:Children (1–13) 3146:Children (1–13) 3124:Children (1–13) 3109: 3023: 3019: 3018: μg/L and 3015: 3008: 3007: 3006: 2994: 2990: 2940:Children (1–18) 2852: 2787: 2778:β-methylbutyric 2777: 2774: 2758:β-methylbutyric 2757: 2738:carbon monoxide 2721:of acetone. An 2694: 2675:β-methylbutyric 2674: 2671: 2646: 2638: 2634: 2623: 2619: 2583:β-methylbutyric 2582: 2579: 2576: 2566:β-methylbutyric 2565: 2558: 2552:located on its 2524:carboxylic acid 2520:β-methylbutyric 2519: 2516: 2514: 2479: 2478: 2473: 2467: 2466: 2463: 2460: 2459: 2452: 2438:β-methylbutyric 2437: 2434: 2431:β-methylbutyric 2430: 2427: 2424: 2418: 2412: 2406: 2400:natural product 2389:β-methylbutyric 2388: 2385: 2383: 2382: 2381: 2380: 2379: 2376: 2373: 2364: 2363: 2362: 2352: 2341: 2329: 2328: 2327: 2311: 2307: 2303: 2298:and an unknown 2291: 2283: 2269: 2268:branched-chain 2257: 2246: 2245: 2244: 2234: 2233: 2232: 2228: 2221: 2220: 2219: 2207: 2206: 2205: 2197: 2182: 2171: 2167: 2159: 2155: 2143: 2139: 2131: 2119: 2114: 2111: 2107: 2102: 2101: 2100: 2093: 2092: 2091: 2083: 2082: 2081: 2070: 2062: 2061: 2060: 2059: 2054: 2052: 2047: 2045: 2040: 2038: 2033: 2031: 2028:Acetoacetyl-CoA 2026: 2024: 2019: 2017: 2014: 2012: 2010: 2005: 2003: 1999: 1996: 1994: 1990: 1987: 1985: 1981: 1978: 1976: 1972: 1969: 1967: 1963: 1960: 1958: 1954: 1951: 1949: 1945: 1942: 1940: 1935: 1933: 1929: 1926: 1920: 1918: 1914: 1909: 1907: 1904: 1899: 1897: 1893: 1888: 1886: 1883: 1878: 1876: 1873: 1868: 1866: 1863: 1858: 1856: 1853: 1848: 1846: 1843: 1839: 1837: 1834: 1830: 1828: 1825: 1821: 1819: 1814: 1811: 1809: 1806: 1804: 1800: 1798: 1791: 1788: 1785: 1783: 1778: 1776: 1769: 1767:KIC-dioxygenase 1765: 1763: 1754: 1751: 1749: 1739: 1737: 1727: 1725: 1720: 1718: 1713: 1711: 1706: 1704: 1699: 1697: 1694:α-Ketoglutarate 1692: 1690: 1686: 1683: 1681: 1673: 1672: 1671: 1669: 1665: 1657: 1647: 1638: 1634: 1633:, with roughly 1627: 1615: 1598:of the calcium 1591: 1584: 1575: 1558:The free acid ( 1556: 1535: 1467:differentiation 1452:creatine kinase 1401: 1400: 1399: 1352: 1340:phosphorylation 1332: 1331: 1330: 1313: 1308: 1307: 1306: 1305: 1304: 1303: 1302: 1300: 1298: 1296: 1291: 1282: 1273: 1268: 1263: 1258: 1253: 1248: 1243: 1238: 1233: 1228: 1223: 1218: 1216:phospholipase D 1212: 1208: 1200: 1199: 1198: 1176:Diagram of the 1174: 1163: 1141:of HMB for the 1130:adverse effects 1122:clinical trials 1114: 1086: 1078: 1039:aerobic fitness 1010: 990: 989: 981: 980: 935:that occurs in 933:muscle strength 929:muscle function 901:adjunct therapy 893:clinical trials 889: 841: 837: 826: 825: 824: 818: 786: 784:Available forms 781: 756: 710: 704:adverse effects 684:Medical reviews 680:skeletal muscle 638: 635: 611: 609: 604: 601: 596: 591: 590: 579: 576: 575:CC(C)(CC(=O)O)O 571: 570: 526: 501: 491: 485: 479: 440: 416: 408: 388: 368: 348: 328: 311: 303: 283: 280: 275: 274: 241: 231: 220: 212:Onset of action 168:Pharmacokinetic 162: 126: 99: 91: 86: 84: 82: 65: 63: 37: 28: 23: 22: 15: 12: 11: 5: 9969: 9959: 9958: 9953: 9948: 9943: 9938: 9933: 9928: 9923: 9921:Ergogenic aids 9918: 9913: 9908: 9903: 9898: 9883: 9882: 9870: 9858: 9835: 9834: 9831: 9830: 9829: 9828: 9825: 9814: 9808: 9802: 9801: 9798: 9797: 9794: 9793: 9791: 9790: 9784: 9782: 9776: 9775: 9773: 9772: 9767: 9762: 9756: 9754: 9748: 9747: 9745: 9744: 9739: 9733: 9731: 9725: 9724: 9722: 9721: 9719:(III) chloride 9716: 9710: 9708: 9699: 9693: 9692: 9689: 9688: 9686: 9685: 9680: 9675: 9670: 9665: 9657: 9649: 9643: 9641: 9635: 9634: 9632: 9631: 9626: 9620: 9618: 9612: 9611: 9609: 9608: 9603: 9597: 9595: 9589: 9588: 9586: 9585: 9579: 9577: 9571: 9570: 9568: 9567: 9561: 9559: 9550: 9544: 9543: 9540: 9539: 9537: 9536: 9531: 9526: 9521: 9516: 9514:Sodium sulfate 9511: 9503: 9498: 9493: 9491:-α-lipoic acid 9485: 9473: 9468: 9460: 9455: 9450: 9442: 9434: 9426: 9421: 9419:barium sulfate 9415: 9413: 9407: 9406: 9404: 9403: 9398: 9396:Suramin sodium 9393: 9388: 9383: 9381:stibogluconate 9378: 9373: 9368: 9363: 9358: 9353: 9348: 9343: 9338: 9333: 9328: 9323: 9318: 9316:Heparin sodium 9313: 9308: 9302: 9300: 9294: 9293: 9291: 9290: 9285: 9280: 9275: 9270: 9265: 9260: 9255: 9245: 9240: 9235: 9230: 9225: 9219: 9217: 9211: 9210: 9208: 9207: 9202: 9200:hydroxyapatite 9197: 9191: 9189: 9183: 9182: 9180: 9179: 9174: 9169: 9164: 9159: 9154: 9149: 9144: 9139: 9134: 9129: 9124: 9119: 9114: 9109: 9104: 9098: 9096: 9090: 9089: 9087: 9086: 9084:hydroxyapatite 9081: 9076: 9071: 9066: 9061: 9056: 9051: 9046: 9041: 9039:glucoheptonate 9036: 9031: 9026: 9021: 9016: 9011: 9006: 9001: 8996: 8990: 8988: 8979: 8975: 8974: 8962: 8961: 8954: 8947: 8939: 8930: 8929: 8927: 8926: 8921: 8916: 8911: 8906: 8901: 8896: 8890: 8888: 8884: 8883: 8881: 8880: 8878:Zinc gluconate 8875: 8870: 8865: 8860: 8855: 8853:St John's wort 8850: 8845: 8840: 8835: 8833:Red yeast rice 8830: 8825: 8820: 8815: 8810: 8805: 8800: 8795: 8790: 8785: 8780: 8775: 8770: 8765: 8760: 8755: 8750: 8745: 8740: 8735: 8730: 8725: 8720: 8715: 8710: 8704: 8702: 8696: 8695: 8693: 8692: 8687: 8682: 8677: 8672: 8667: 8662: 8657: 8652: 8647: 8642: 8637: 8632: 8627: 8622: 8617: 8612: 8606: 8605: 8600: 8595: 8590: 8585: 8584: 8583: 8578: 8574: 8569: 8565: 8560: 8556: 8551: 8547: 8542: 8538: 8533: 8529: 8524: 8520: 8515: 8506: 8500: 8498: 8485: 8484: 8482: 8481: 8476: 8471: 8465: 8456: 8451: 8446: 8441: 8436: 8431: 8426: 8420: 8418: 8414: 8413: 8406: 8405: 8398: 8391: 8383: 8374: 8373: 8370: 8369: 8367: 8366: 8364:Ergocalciferol 8361: 8356: 8351: 8349:Ergostatrienol 8346: 8341: 8335: 8333: 8331:Ergocalciferol 8326: 8325: 8323: 8322: 8311: 8306: 8301: 8296: 8291: 8286: 8284:Cycloeucalenol 8281: 8275: 8273: 8263: 8259: 8258: 8256: 8255: 8248: 8239: 8229: 8227: 8215: 8214: 8212: 8211: 8206: 8201: 8196: 8191: 8185: 8184: 8179: 8174: 8169: 8164: 8158: 8157: 8152: 8147: 8142: 8137: 8131: 8130: 8125: 8120: 8115: 8109: 8107: 8100: 8099: 8096: 8095: 8093: 8092: 8087: 8082: 8077: 8072: 8067: 8062: 8057: 8051: 8045: 8039: 8038: 8035: 8034: 8032: 8031: 8026: 8020: 8018: 8012: 8011: 8009: 8008: 8003: 7997: 7995: 7991: 7990: 7988: 7987: 7982: 7977: 7972: 7967: 7965:Mevalonic acid 7961: 7959: 7952: 7951: 7949: 7948: 7943: 7938: 7932: 7930: 7924: 7923: 7921: 7920: 7915: 7910: 7905: 7900: 7894: 7892: 7882: 7876: 7875: 7861: 7860: 7853: 7846: 7838: 7829: 7828: 7825: 7824: 7822: 7821: 7815: 7813: 7804: 7800: 7799: 7796: 7795: 7793: 7792: 7783: 7781: 7774: 7773: 7770: 7769: 7767: 7766: 7761: 7756: 7750: 7748: 7734: 7727: 7726: 7723: 7722: 7720: 7719: 7713: 7711: 7704: 7703: 7701: 7700: 7694: 7692: 7685: 7684: 7682: 7681: 7672: 7660: 7659: 7654: 7640: 7625: 7623: 7616: 7615: 7613: 7612: 7607: 7602: 7597: 7591: 7589: 7582: 7581: 7579: 7578: 7573: 7568: 7563: 7558: 7556:Isobutyryl-CoA 7553: 7547: 7545: 7535: 7523: 7522: 7519: 7518: 7516: 7515: 7497: 7495: 7491: 7490: 7488: 7487: 7482: 7477: 7472: 7467: 7461: 7459: 7452: 7451: 7449: 7448: 7442: 7440: 7433: 7432: 7430: 7429: 7424: 7419: 7414: 7408: 7406: 7396: 7384: 7383: 7380: 7379: 7377: 7376: 7371: 7366: 7352: 7351: 7345: 7343: 7328: 7313: 7307: 7306: 7303: 7302: 7300: 7299: 7294: 7289: 7284: 7279: 7274: 7269: 7264: 7259: 7250: 7248: 7237: 7236: 7234: 7233: 7228: 7223: 7218: 7213: 7208: 7203: 7198: 7196:Isovaleryl-CoA 7193: 7188: 7182: 7180: 7173: 7172: 7170: 7169: 7164: 7159: 7157:Glutaconyl-CoA 7154: 7149: 7144: 7139: 7134: 7128: 7126: 7116: 7106: 7105: 7092: 7091: 7084: 7077: 7069: 7063: 7062: 7050: 7049:External links 7047: 7044: 7043: 6993: 6954: 6947: 6921: 6886: 6856: 6817: 6776: 6715: 6704: 6682: 6675: 6653: 6634:(9): 765–772. 6615: 6596: 6585:(2): 486–488. 6569: 6548:abstracted by 6542:(in Russian). 6530: 6523: 6494: 6483:(1): 396–419. 6463: 6452:(1): 196–208. 6432: 6388: 6355: 6336: 6306: 6243: 6217: 6187: 6157: 6117: 6068: 6014: 5956: 5921: 5902:(5): 755–763. 5880: 5838: 5809:(4): 452–460. 5784: 5728: 5696: 5669:(7): 727–735. 5652: 5622:(7): 640–649. 5600: 5548: 5523:(5): 567–575. 5500: 5444: 5421:(1): 146–147. 5405: 5350: 5323:(9): 789–796. 5294: 5271:(7): 668–672. 5250: 5214: 5189: 5154: 5135: 5108: 5091: 5060: 5035:(3): 405–417. 4992: 4938: 4897: 4843: 4812:(4): 517–531. 4783: 4717: 4639: 4560: 4476: 4407: 4356: 4323:(4): 529–541. 4292: 4269:(2): 168–175. 4229: 4196: 4163:(5): 525–529. 4140: 4094: 4062: 4023: 3987: 3958: 3886: 3809: 3684: 3683: 3681: 3678: 3675: 3674: 3668: 3659: 3652: 3651: 3649: 3646: 3643: 3642: 3629: 3620: 3598: 3563: 3524: 3507: 3491:, and urinary 3462: 3454:control groups 3432: 3398:-methylbutyric 3378: 3377: 3375: 3372: 3371: 3370: 3363: 3360: 3304: 3301: 3298: 3297: 3285: 3284: 3282: 3279: 3278:1700.0–59000.0 3276: 3273: 3270: 3267: 3261: 3260: 3258: 3255: 3252: 3249: 3246: 3243: 3237: 3236: 3234: 3231: 3228: 3225: 3222: 3219: 3213: 3212: 3210: 3207: 3204: 3201: 3198: 3195: 3189: 3188: 3186: 3183: 3180: 3177: 3174: 3171: 3165: 3164: 3162: 3153: 3150: 3147: 3144: 3141: 3137: 3136: 3134: 3131: 3128: 3125: 3122: 3119: 3115: 3114: 3112: 3102: 3099: 3096: 3093: 3090: 3084: 3083: 3080: 3077: 3073: 3072: 3067: 3066:Concentration 3064: 3061: 3058: 2953: 2952: 2950: 2947: 2944: 2941: 2938: 2934: 2933: 2931: 2925: 2922: 2919: 2916: 2912: 2911: 2909: 2904: 2901: 2898: 2895: 2891: 2890: 2888: 2885: 2882: 2879: 2878:Adults (21–23) 2876: 2870: 2869: 2867: 2864: 2861: 2858: 2855: 2844: 2843: 2841: 2836: 2833: 2830: 2827: 2821: 2820: 2817: 2814: 2810: 2809: 2804: 2803:Concentration 2801: 2798: 2786: 2783: 2734:-butyl alcohol 2723:organometallic 2664: 2663: 2660: 2644: 2636: 2632: 2625: 2621: 2617: 2575: 2572: 2513: 2510: 2494: 2491: 2488: 2485: 2482: 2470: 2450: 2422: 2416: 2410: 2396:β-hydroxy acid 2393:monocarboxylic 2374: 2367: 2366: 2365: 2353: 2346: 2345: 2344: 2343: 2342: 2340: 2337: 2276:isovaleryl-CoA 2196: 2193: 2104: 2103: 2077:isovaleryl-CoA 2064: 2063: 1944:Isovaleryl-CoA 1912: 1902: 1891: 1881: 1871: 1861: 1851: 1780:Isovaleryl-CoA 1667: 1666: 1659: 1658: 1655: 1654: 1653: 1648: 1646: 1643: 1626: 1623: 1613: 1583: 1580: 1555: 1552: 1534: 1531: 1381:growth hormone 1312: 1309: 1213: 1210: 1209: 1175: 1168: 1167: 1166: 1165: 1164: 1162: 1159: 1126:animal studies 1124:in humans and 1118:safety profile 1113: 1110: 1009: 1006: 998:lean body mass 960:muscle wasting 937:hypercatabolic 921:muscle atrophy 888: 885: 813:conjugate base 785: 782: 780: 777: 676:lean body mass 660:muscle wasting 631:conjugate base 618: 617: 606: 605: 603: 602: 599: 597: 594: 586: 585: 584: 581: 580: 578: 577: 574: 566: 565: 564: 561: 560: 554: 548: 547: 544: 538: 537: 534: 528: 527: 525: 524: 516: 514: 506: 505: 499: 493: 492: 489: 483: 477: 472: 466: 465: 461: 460: 450: 442: 441: 439: 438: 430:DTXSID20211535 425: 423: 410: 409: 407: 406: 398: 396: 390: 389: 387: 386: 378: 376: 370: 369: 367: 366: 358: 356: 350: 349: 347: 346: 338: 336: 330: 329: 327: 326: 318: 316: 305: 304: 302: 301: 293: 291: 285: 284: 282: 281: 278: 270: 269: 268: 265: 264: 260: 259: 253: 247: 246: 240:: 3 hours 235: 226: 225: 214: 208: 207: 178: 172: 171: 164: 163: 161: 160: 151: 141: 139: 133: 132: 128: 127: 125: 124: 120: 118: 112: 111: 102: 100:administration 94: 93: 88:Conjugate base 79:Conjugate acid 76: 72: 71: 67: 66: 61: 53: 52: 26: 9: 6: 4: 3: 2: 9968: 9957: 9954: 9952: 9949: 9947: 9944: 9942: 9939: 9937: 9934: 9932: 9929: 9927: 9924: 9922: 9919: 9917: 9914: 9912: 9909: 9907: 9904: 9902: 9899: 9897: 9894: 9893: 9891: 9881: 9876: 9871: 9869: 9859: 9857: 9847: 9846: 9843: 9826: 9824: 9821: 9820: 9818: 9815: 9812: 9809: 9807: 9804: 9803: 9799: 9789: 9786: 9785: 9783: 9781: 9777: 9771: 9768: 9766: 9763: 9761: 9758: 9757: 9755: 9753: 9749: 9743: 9740: 9738: 9735: 9734: 9732: 9730: 9726: 9720: 9717: 9715: 9712: 9711: 9709: 9707: 9703: 9700: 9698: 9694: 9684: 9681: 9679: 9676: 9674: 9671: 9669: 9666: 9664: 9658: 9656: 9650: 9648: 9645: 9644: 9642: 9640: 9636: 9630: 9627: 9625: 9622: 9621: 9619: 9617: 9613: 9607: 9604: 9602: 9601:(II) fumarate 9599: 9598: 9596: 9594: 9590: 9584: 9581: 9580: 9578: 9576: 9572: 9566: 9563: 9562: 9560: 9558: 9554: 9551: 9549: 9545: 9535: 9532: 9530: 9527: 9525: 9522: 9520: 9517: 9515: 9512: 9510: 9508: 9504: 9502: 9499: 9497: 9494: 9492: 9490: 9486: 9484: 9478: 9474: 9472: 9469: 9467: 9461: 9459: 9456: 9454: 9451: 9449: 9443: 9441: 9435: 9433: 9427: 9425: 9422: 9420: 9417: 9416: 9414: 9412: 9408: 9402: 9401:Valproic acid 9399: 9397: 9394: 9392: 9389: 9387: 9384: 9382: 9379: 9377: 9374: 9372: 9371:nitroprusside 9369: 9367: 9364: 9362: 9359: 9357: 9354: 9352: 9349: 9347: 9344: 9342: 9339: 9337: 9334: 9332: 9329: 9327: 9324: 9322: 9319: 9317: 9314: 9312: 9309: 9307: 9304: 9303: 9301: 9299: 9295: 9289: 9286: 9284: 9281: 9279: 9276: 9274: 9271: 9269: 9266: 9264: 9261: 9259: 9256: 9253: 9249: 9246: 9244: 9241: 9239: 9236: 9234: 9231: 9229: 9226: 9224: 9221: 9220: 9218: 9216: 9212: 9206: 9203: 9201: 9198: 9196: 9193: 9192: 9190: 9188: 9184: 9178: 9175: 9173: 9170: 9168: 9165: 9163: 9160: 9158: 9155: 9153: 9150: 9148: 9145: 9143: 9140: 9138: 9135: 9133: 9130: 9128: 9125: 9123: 9120: 9118: 9115: 9113: 9110: 9108: 9105: 9103: 9100: 9099: 9097: 9095: 9091: 9085: 9082: 9080: 9077: 9075: 9072: 9070: 9067: 9065: 9062: 9060: 9057: 9055: 9052: 9050: 9047: 9045: 9042: 9040: 9037: 9035: 9032: 9030: 9027: 9025: 9022: 9020: 9017: 9015: 9012: 9010: 9007: 9005: 9002: 9000: 8997: 8995: 8992: 8991: 8989: 8987: 8983: 8980: 8976: 8971: 8967: 8960: 8955: 8953: 8948: 8946: 8941: 8940: 8937: 8925: 8922: 8920: 8917: 8915: 8914:Nutraceutical 8912: 8910: 8907: 8905: 8902: 8900: 8897: 8895: 8892: 8891: 8889: 8885: 8879: 8876: 8874: 8871: 8869: 8866: 8864: 8861: 8859: 8856: 8854: 8851: 8849: 8846: 8844: 8841: 8839: 8836: 8834: 8831: 8829: 8826: 8824: 8821: 8819: 8816: 8814: 8811: 8809: 8806: 8804: 8801: 8799: 8796: 8794: 8791: 8789: 8786: 8784: 8781: 8779: 8776: 8774: 8771: 8769: 8766: 8764: 8761: 8759: 8756: 8754: 8751: 8749: 8746: 8744: 8743:Dietary fiber 8741: 8739: 8736: 8734: 8731: 8729: 8728:Cod liver oil 8726: 8724: 8721: 8719: 8716: 8714: 8711: 8709: 8706: 8705: 8703: 8699:Other common 8697: 8691: 8688: 8686: 8683: 8681: 8678: 8676: 8673: 8671: 8668: 8666: 8663: 8661: 8658: 8656: 8653: 8651: 8648: 8646: 8643: 8641: 8638: 8636: 8633: 8631: 8628: 8626: 8623: 8621: 8618: 8616: 8613: 8611: 8608: 8607: 8604: 8601: 8599: 8596: 8594: 8591: 8589: 8586: 8582: 8575: 8573: 8568:Folic acid (B 8566: 8564: 8557: 8555: 8550:Pyridoxine (B 8548: 8546: 8539: 8537: 8530: 8528: 8523:Riboflavin (B 8521: 8519: 8512: 8511: 8510: 8507: 8505: 8502: 8501: 8499: 8497: 8490: 8486: 8480: 8477: 8475: 8472: 8469: 8466: 8464: 8463:Lactobacillus 8460: 8457: 8455: 8452: 8450: 8447: 8445: 8442: 8440: 8437: 8435: 8432: 8430: 8427: 8425: 8422: 8421: 8419: 8415: 8411: 8404: 8399: 8397: 8392: 8390: 8385: 8384: 8381: 8365: 8362: 8360: 8357: 8355: 8352: 8350: 8347: 8345: 8342: 8340: 8337: 8336: 8334: 8332: 8327: 8320: 8316: 8312: 8310: 8307: 8305: 8302: 8300: 8299:Isofucosterol 8297: 8295: 8292: 8290: 8287: 8285: 8282: 8280: 8277: 8276: 8274: 8272: 8267: 8264: 8260: 8253: 8249: 8247: 8245: 8240: 8238: 8236: 8231: 8230: 8228: 8226: 8221: 8216: 8210: 8207: 8205: 8202: 8200: 8197: 8195: 8192: 8190: 8187: 8186: 8183: 8180: 8178: 8175: 8173: 8170: 8168: 8165: 8163: 8160: 8159: 8156: 8153: 8151: 8148: 8146: 8143: 8141: 8138: 8136: 8133: 8132: 8129: 8126: 8124: 8121: 8119: 8116: 8114: 8111: 8110: 8108: 8106: 8101: 8091: 8088: 8086: 8083: 8081: 8078: 8076: 8073: 8071: 8068: 8066: 8063: 8061: 8058: 8056: 8053: 8052: 8049: 8046: 8044: 8040: 8030: 8027: 8025: 8022: 8021: 8019: 8017: 8013: 8007: 8004: 8002: 7999: 7998: 7996: 7992: 7986: 7983: 7981: 7978: 7976: 7973: 7971: 7968: 7966: 7963: 7962: 7960: 7958: 7953: 7947: 7944: 7942: 7939: 7937: 7934: 7933: 7931: 7929: 7928:Ketone bodies 7925: 7919: 7916: 7914: 7911: 7909: 7906: 7904: 7901: 7899: 7896: 7895: 7893: 7891: 7886: 7883: 7881: 7877: 7873: 7870: 7866: 7859: 7854: 7852: 7847: 7845: 7840: 7839: 7836: 7820: 7817: 7816: 7814: 7812: 7808: 7805: 7801: 7791: 7790: 7785: 7784: 7782: 7780: 7775: 7765: 7762: 7760: 7757: 7755: 7752: 7751: 7749: 7746: 7742: 7741:phenylalanine 7738: 7735: 7733: 7728: 7718: 7715: 7714: 7712: 7709: 7708:propionyl-CoA 7705: 7699: 7696: 7695: 7693: 7690: 7686: 7680: 7676: 7673: 7671: 7670:Cystathionine 7668: 7666: 7662: 7661: 7658: 7655: 7653: 7652:-homocysteine 7645: 7641: 7639: 7637: 7633: 7631: 7627: 7626: 7624: 7621: 7617: 7611: 7608: 7606: 7603: 7601: 7598: 7596: 7593: 7592: 7590: 7587: 7583: 7577: 7574: 7572: 7569: 7567: 7564: 7562: 7559: 7557: 7554: 7552: 7549: 7548: 7546: 7543: 7539: 7536: 7534: 7529: 7528:propionyl-CoA 7524: 7514: 7510: 7506: 7502: 7499: 7498: 7496: 7492: 7486: 7483: 7481: 7478: 7476: 7473: 7471: 7468: 7466: 7463: 7462: 7460: 7457: 7453: 7447: 7444: 7443: 7441: 7438: 7434: 7428: 7425: 7423: 7420: 7418: 7415: 7413: 7412:Urocanic acid 7410: 7409: 7407: 7404: 7400: 7397: 7395: 7390: 7385: 7375: 7372: 7370: 7367: 7365: 7361: 7357: 7354: 7353: 7350: 7347: 7346: 7344: 7341: 7336: 7332: 7329: 7327: 7322: 7317: 7314: 7312: 7308: 7298: 7295: 7293: 7290: 7288: 7285: 7283: 7280: 7278: 7275: 7273: 7270: 7268: 7265: 7263: 7260: 7258: 7256: 7252: 7251: 7249: 7246: 7242: 7238: 7232: 7229: 7227: 7224: 7222: 7219: 7217: 7214: 7212: 7209: 7207: 7204: 7202: 7199: 7197: 7194: 7192: 7189: 7187: 7184: 7183: 7181: 7178: 7174: 7168: 7165: 7163: 7160: 7158: 7155: 7153: 7150: 7148: 7145: 7143: 7140: 7138: 7135: 7133: 7130: 7129: 7127: 7124: 7120: 7117: 7115: 7111: 7107: 7103: 7100: 7097: 7090: 7085: 7083: 7078: 7076: 7071: 7070: 7067: 7060: 7056: 7053: 7052: 7039: 7033: 7027: 7021: 7015: 7007: 7006:Justia Patent 7003: 6997: 6978: 6971: 6965: 6963: 6961: 6959: 6950: 6944: 6940: 6936: 6932: 6925: 6917: 6913: 6909: 6905: 6902:(3): 638–41. 6901: 6897: 6890: 6882: 6878: 6874: 6871:(in German). 6870: 6866: 6860: 6852: 6848: 6844: 6840: 6836: 6832: 6824: 6822: 6813: 6809: 6805: 6801: 6797: 6793: 6785: 6783: 6781: 6772: 6768: 6763: 6758: 6754: 6750: 6746: 6742: 6738: 6734: 6730: 6728: 6719: 6711: 6707: 6701: 6697: 6693: 6686: 6678: 6672: 6668: 6664: 6663:"Example 5.2" 6657: 6649: 6645: 6641: 6637: 6633: 6629: 6622: 6620: 6606: 6600: 6592: 6588: 6584: 6580: 6573: 6565: 6561: 6557: 6554:(in German). 6553: 6545: 6541: 6534: 6526: 6520: 6516: 6512: 6508: 6504: 6498: 6490: 6486: 6482: 6479:(in German). 6478: 6474: 6467: 6459: 6455: 6451: 6448:(in German). 6447: 6443: 6436: 6428: 6424: 6420: 6417:(in German). 6416: 6412: 6408: 6401: 6395: 6393: 6376: 6372: 6368: 6362: 6360: 6346: 6340: 6324: 6320: 6316: 6310: 6302: 6301: 6296: 6288: 6286: 6284: 6282: 6280: 6278: 6276: 6274: 6272: 6270: 6268: 6266: 6264: 6262: 6260: 6258: 6256: 6254: 6252: 6250: 6248: 6231: 6227: 6221: 6205: 6201: 6197: 6191: 6175: 6171: 6167: 6161: 6155: 6151: 6148: 6137: 6124: 6120: 6114: 6110: 6109: 6104: 6097: 6095: 6093: 6091: 6089: 6087: 6085: 6083: 6081: 6079: 6077: 6075: 6073: 6065: 6060: 6056: 6052: 6048: 6044: 6040: 6036: 6032: 6028: 6021: 6019: 6011: 6006: 6002: 5997: 5992: 5988: 5984: 5980: 5976: 5972: 5965: 5963: 5961: 5944: 5940: 5936: 5930: 5928: 5926: 5917: 5913: 5909: 5905: 5901: 5897: 5889: 5887: 5885: 5877: 5872: 5868: 5864: 5860: 5856: 5852: 5845: 5843: 5834: 5830: 5825: 5820: 5816: 5812: 5808: 5804: 5800: 5793: 5791: 5789: 5781: 5776: 5772: 5767: 5762: 5758: 5754: 5750: 5746: 5742: 5735: 5733: 5725: 5713: 5709: 5703: 5701: 5692: 5688: 5684: 5680: 5676: 5672: 5668: 5664: 5656: 5649: 5645: 5641: 5637: 5633: 5629: 5625: 5621: 5617: 5609: 5607: 5605: 5597: 5592: 5588: 5584: 5580: 5576: 5572: 5568: 5564: 5557: 5555: 5553: 5545: 5540: 5536: 5531: 5526: 5522: 5518: 5514: 5507: 5505: 5497: 5492: 5488: 5483: 5478: 5474: 5470: 5466: 5462: 5458: 5451: 5449: 5441: 5436: 5432: 5428: 5424: 5420: 5416: 5409: 5402: 5397: 5393: 5388: 5383: 5378: 5373: 5369: 5365: 5361: 5354: 5347: 5340: 5336: 5331: 5326: 5322: 5318: 5314: 5307: 5305: 5303: 5301: 5299: 5291: 5286: 5282: 5278: 5274: 5270: 5266: 5259: 5257: 5255: 5235: 5228: 5221: 5219: 5202: 5196: 5194: 5174: 5167: 5161: 5159: 5142: 5138: 5132: 5128: 5127: 5122: 5115: 5113: 5105: 5094: 5088: 5084: 5079: 5078: 5069: 5067: 5065: 5057: 5052: 5048: 5043: 5038: 5034: 5030: 5026: 5019: 5017: 5015: 5013: 5011: 5009: 5007: 5005: 5003: 5001: 4999: 4997: 4988: 4984: 4979: 4974: 4969: 4964: 4960: 4956: 4952: 4945: 4943: 4923: 4919: 4912: 4906: 4904: 4902: 4894: 4889: 4885: 4880: 4875: 4871: 4867: 4863: 4856: 4854: 4852: 4850: 4848: 4840: 4835: 4831: 4827: 4823: 4819: 4815: 4811: 4807: 4800: 4798: 4796: 4794: 4792: 4790: 4788: 4780: 4775: 4771: 4766: 4761: 4757: 4753: 4749: 4745: 4741: 4734: 4732: 4730: 4728: 4726: 4724: 4722: 4714: 4709: 4705: 4701: 4697: 4693: 4689: 4684: 4679: 4675: 4671: 4667: 4660: 4658: 4656: 4654: 4652: 4650: 4648: 4646: 4644: 4636: 4631: 4627: 4623: 4619: 4615: 4611: 4607: 4603: 4596: 4589: 4587: 4585: 4583: 4581: 4579: 4577: 4575: 4573: 4571: 4569: 4567: 4565: 4557: 4552: 4548: 4543: 4538: 4534: 4530: 4526: 4522: 4518: 4511: 4509: 4507: 4505: 4503: 4501: 4499: 4497: 4495: 4493: 4491: 4489: 4487: 4485: 4483: 4481: 4473: 4468: 4464: 4459: 4454: 4450: 4446: 4442: 4438: 4431: 4424: 4422: 4420: 4418: 4416: 4414: 4412: 4404: 4399: 4395: 4391: 4387: 4383: 4379: 4375: 4371: 4363: 4361: 4353: 4348: 4344: 4339: 4334: 4330: 4326: 4322: 4318: 4314: 4307: 4305: 4303: 4301: 4299: 4297: 4289: 4284: 4280: 4276: 4272: 4268: 4264: 4256: 4254: 4252: 4250: 4248: 4246: 4244: 4242: 4240: 4238: 4236: 4234: 4217: 4213: 4209: 4203: 4201: 4193: 4188: 4184: 4180: 4176: 4171: 4166: 4162: 4158: 4154: 4147: 4145: 4137: 4124: 4120: 4113: 4111: 4109: 4107: 4105: 4103: 4101: 4099: 4091: 4079: 4075: 4074: 4066: 4059: 4043: 4039: 4038: 4030: 4028: 4019: 4015: 4011: 4007: 4000: 3998: 3996: 3994: 3992: 3975: 3971: 3965: 3963: 3955: 3950: 3946: 3942: 3938: 3934: 3930: 3926: 3922: 3918: 3911: 3909: 3907: 3905: 3903: 3901: 3899: 3897: 3895: 3893: 3891: 3883: 3863: 3856: 3849: 3831: 3824: 3818: 3816: 3814: 3806: 3801: 3797: 3792: 3787: 3782: 3777: 3773: 3769: 3765: 3758: 3756: 3754: 3752: 3750: 3748: 3746: 3744: 3742: 3740: 3738: 3736: 3734: 3732: 3730: 3728: 3726: 3724: 3722: 3720: 3718: 3716: 3714: 3712: 3710: 3708: 3706: 3704: 3702: 3700: 3698: 3696: 3694: 3692: 3690: 3685: 3672: 3666: 3664: 3657: 3653: 3639: 3633: 3624: 3617: 3605: 3603: 3586: 3567: 3551: 3547: 3528: 3517: 3511: 3504: 3500: 3495: 3490: 3489:urea nitrogen 3486: 3482: 3479: 3475: 3469: 3467: 3459: 3455: 3451: 3445: 3439: 3437: 3429: 3425: 3419: 3412: 3408: 3401: 3397: 3391: 3383: 3379: 3369: 3366: 3365: 3359: 3356: 3351: 3347: 3339: 3334: 3332: 3328: 3324: 3320: 3319: 3314: 3310: 3293: 3286: 3283: 3280: 3277: 3274: 3271: 3268: 3266: 3263: 3262: 3259: 3256: 3253: 3250: 3247: 3244: 3242: 3239: 3238: 3235: 3232: 3229: 3226: 3223: 3220: 3218: 3215: 3214: 3211: 3208: 3205: 3202: 3199: 3196: 3194: 3191: 3190: 3187: 3184: 3181: 3178: 3175: 3172: 3170: 3167: 3166: 3163: 3161: 3154: 3151: 3148: 3145: 3142: 3139: 3138: 3135: 3132: 3129: 3126: 3123: 3120: 3117: 3116: 3113: 3108: 3103: 3100: 3097: 3094: 3091: 3089: 3086: 3085: 3074: 3055: 3049: 3047: 3043: 3038: 3027: 3004: 3000: 2988: 2984: 2980: 2976: 2972: 2968: 2964: 2960: 2951: 2948: 2945: 2942: 2939: 2936: 2935: 2932: 2926: 2923: 2920: 2917: 2914: 2913: 2910: 2905: 2902: 2899: 2896: 2893: 2892: 2889: 2886: 2883: 2880: 2877: 2875: 2872: 2871: 2868: 2865: 2862: 2859: 2856: 2851: 2846: 2845: 2842: 2837: 2834: 2831: 2828: 2826: 2823: 2822: 2811: 2797: 2793: 2771: 2767: 2765: 2764: 2755: 2751: 2747: 2743: 2739: 2735: 2733: 2728: 2727:carboxylation 2724: 2720: 2716: 2712: 2708: 2704: 2700: 2692: 2688: 2684: 2683:cycloaddition 2668: 2661: 2658: 2654: 2650: 2642: 2630: 2626: 2615: 2611: 2607: 2606: 2605: 2603: 2599: 2596: 2592: 2588: 2571: 2569: 2562: 2555: 2551: 2548: 2544: 2541: 2537: 2533: 2529: 2525: 2509: 2486: 2483: 2480: 2457: 2453: 2449: 2443: 2421: 2415: 2409: 2405: 2401: 2397: 2394: 2371: 2360: 2356: 2350: 2336: 2325: 2321: 2317: 2301: 2297: 2289: 2281: 2277: 2273: 2272:dehydrogenase 2265: 2264:mitochondrial 2260: 2255: 2241: 2217: 2213: 2202: 2192: 2190: 2186: 2179: 2174: 2165: 2153: 2149: 2137: 2129: 2125: 2117: 2089: 2078: 2074: 2057: 2050: 2043: 2036: 2029: 2022: 2008: 2001: 1992: 1991:dehydrogenase 1983: 1980:HMG-CoA 1974: 1965: 1956: 1947: 1946:dehydrogenase 1938: 1931: 1924: 1916: 1905: 1895: 1884: 1874: 1864: 1854: 1842: 1833: 1824: 1817: 1812: 1803: 1795: 1790: 1781: 1773: 1768: 1760: 1756: 1755:dehydrogenase 1746: 1742: 1734: 1730: 1723: 1716: 1709: 1702: 1695: 1688: 1679: 1663: 1652: 1651: 1642: 1632: 1622: 1620: 1616: 1609: 1605: 1601: 1597: 1579: 1573: 1569: 1548: 1545:per liter of 1544: 1539: 1530: 1528: 1524: 1520: 1516: 1512: 1509: 1505: 1501: 1497: 1493: 1489: 1485: 1481: 1480: 1476: 1472: 1468: 1464: 1463:proliferation 1459: 1457: 1453: 1449: 1445: 1441: 1437: 1432: 1430: 1426: 1422: 1418: 1414: 1410: 1397: 1393: 1388: 1386: 1382: 1378: 1374: 1370: 1366: 1362: 1358: 1351: 1345: 1341: 1328: 1324: 1323: 1318: 1295: 1290: 1289:mitochondrial 1286: 1281: 1277: 1272: 1267: 1262: 1257: 1252: 1247: 1242: 1237: 1232: 1227: 1222: 1217: 1206: 1195: 1191: 1187: 1183: 1180:biomolecular 1179: 1172: 1158: 1156: 1150: 1148: 1144: 1140: 1136: 1131: 1127: 1123: 1119: 1109: 1107: 1103: 1099: 1095: 1090: 1070: 1068: 1064: 1060: 1056: 1052: 1048: 1044: 1040: 1031: 1027: 1019: 1014: 1005: 1003: 999: 995: 986: 973: 972:wound healing 970:, to promote 969: 965: 961: 957: 956:medical foods 952: 948: 946: 942: 938: 934: 930: 926: 922: 918: 914: 910: 909:meta-analysis 906: 902: 898: 894: 884: 882: 878: 874: 870: 866: 862: 858: 854: 850: 844: 835: 822: 814: 810: 806: 802: 798: 794: 791: 776: 774: 770: 766: 762: 754: 749: 747: 743: 739: 735: 731: 727: 723: 719: 713: 707: 705: 701: 697: 693: 689: 688:meta-analyses 685: 681: 677: 673: 669: 665: 661: 657: 656:wound healing 653: 652:medical foods 649: 645: 641: 632: 628: 624: 614: 607: 598: 593: 592: 589: 582: 573: 572: 569: 562: 559: 555: 553: 552:Boiling point 549: 545: 543: 542:Melting point 539: 535: 533: 529: 522: 518: 517: 515: 512: 507: 500: 498: 494: 473: 471: 467: 462: 458: 454: 451: 449: 447:ECHA InfoCard 443: 435: 431: 427: 426: 424: 415: 411: 404: 400: 399: 397: 395: 391: 384: 380: 379: 377: 375: 371: 364: 360: 359: 357: 355: 351: 344: 340: 339: 337: 335: 331: 324: 320: 319: 317: 310: 306: 299: 295: 294: 292: 290: 286: 277: 276: 273: 266: 261: 257: 254: 252: 248: 236: 234: 227: 215: 213: 209: 206: 202: 198: 194: 190: 186: 182: 179: 177: 173: 169: 165: 152: 143: 142: 140: 138: 134: 129: 122: 121: 119: 117: 113: 110: 106: 103: 101: 95: 89: 80: 77: 73: 70:Clinical data 68: 59: 54: 50: 45: 39: 35: 30: 19: 9936:Medical food 9906:Biomolecules 9788:(IV) sulfate 9683:zinc sulfate 9606:(II) sulfate 9534:zinc sulfate 9529:(IV) sulfate 9506: 9488: 9476: 9448:-glutathione 9278:permanganate 8919:Multivitamin 8843:Saw palmetto 8823:Milk thistle 8496:("minerals") 8429:Energy drink 8315:Phytosterols 8289:Obtusifoliol 8279:Cycloartenol 8243: 8234: 7786: 7779:oxaloacetate 7663: 7657:Homocysteine 7643: 7635: 7628: 7533:succinyl-CoA 7364:Glycocyamine 7297:Glutaryl-CoA 7254: 7162:Crotonyl-CoA 7152:Glutaryl-CoA 7132:Saccharopine 7005: 6996: 6984:. Retrieved 6930: 6924: 6899: 6895: 6889: 6872: 6868: 6859: 6834: 6830: 6795: 6791: 6736: 6732: 6726: 6718: 6695: 6685: 6666: 6656: 6631: 6627: 6599: 6582: 6578: 6572: 6555: 6551: 6543: 6539: 6533: 6510: 6497: 6480: 6476: 6466: 6449: 6445: 6435: 6418: 6414: 6405:Saytzeff M, 6379:. Retrieved 6370: 6339: 6327:. Retrieved 6318: 6309: 6298: 6234:. Retrieved 6229: 6220: 6208:. Retrieved 6199: 6190: 6178:. Retrieved 6174:the original 6169: 6160: 6134: 6127:. Retrieved 6107: 6062: 6034: 6030: 6008: 5978: 5974: 5947:. Retrieved 5938: 5899: 5895: 5874: 5854: 5850: 5806: 5802: 5778: 5751:(1): 15–41. 5748: 5744: 5723: 5716:. Retrieved 5666: 5662: 5655: 5647: 5619: 5615: 5594: 5566: 5562: 5542: 5520: 5516: 5494: 5467:(1): 25–39. 5464: 5460: 5438: 5418: 5414: 5408: 5399: 5367: 5363: 5353: 5342: 5320: 5316: 5288: 5268: 5264: 5241:. Retrieved 5205:. Retrieved 5180:. Retrieved 5145:. Retrieved 5125: 5103: 5096:. Retrieved 5076: 5054: 5032: 5028: 4958: 4954: 4929:. Retrieved 4922:the original 4917: 4891: 4869: 4865: 4837: 4809: 4805: 4777: 4747: 4743: 4711: 4692:11573/524784 4673: 4669: 4633: 4605: 4601: 4554: 4524: 4520: 4470: 4458:11449/170023 4440: 4436: 4401: 4373: 4369: 4350: 4320: 4316: 4286: 4266: 4262: 4220:. Retrieved 4216:the original 4211: 4190: 4160: 4156: 4134: 4127:. Retrieved 4123:the original 4089: 4082:. Retrieved 4072: 4065: 4053: 4046:. Retrieved 4036: 4009: 4005: 3978:. Retrieved 3952: 3924: 3920: 3876: 3869:. Retrieved 3844: 3837:. Retrieved 3803: 3771: 3767: 3671: 3656: 3638:thioesterase 3632: 3623: 3566: 3527: 3510: 3423: 3421: 3414: 3403: 3395: 3389: 3387: 3382: 3335: 3316: 3306: 3095:Adults (18+) 3039: 3028: 2956: 2918:Adults (18+) 2897:Adults (18+) 2857:Adults (18+) 2829:Adults (18+) 2825:Blood plasma 2761: 2750:ferrous iron 2731: 2680: 2640: 2614:chromic acid 2604:precursors: 2577: 2536:butyric acid 2515: 2454:of 4.4. Its 2447: 2384: 2359:butyric acid 2300:thioesterase 2242: 2198: 2195:Biosynthesis 2178:acetoacetate 2108: 2079:relative to 2075:for HMB and 2042:Acetoacetate 1810: 1793: 1786: 1759:mitochondria 1628: 1596:dissociation 1585: 1557: 1547:blood plasma 1518: 1503: 1477: 1460: 1433: 1395: 1389: 1365:p70S6 kinase 1359:in cellular 1320: 1314: 1285:myofibrillar 1251:p70S6 kinase 1186:myofibrillar 1161:Pharmacology 1151: 1115: 1112:Side effects 1091: 1085:is ingested 1077:is ingested 1071: 1047:myofibrillar 1035: 953: 949: 890: 834:blood plasma 816: 805:monohydrated 800: 787: 750: 708: 634: 626: 622: 621: 610: 230:Elimination 201:acetoacetate 137:Legal status 131:Legal status 38: 29: 9813:from market 9466:-methionine 9391:thiosulfate 9228:bicarbonate 9177:L-threonate 8838:Royal jelly 8818:Lipoic acid 8813:Linseed oil 8773:Glucosamine 8701:ingredients 8514:Thiamine (B 8439:Fatty acids 8220:Cholesterol 8209:Cholesterol 8204:Desmosterol 8182:Cholesterol 8172:Lathosterol 8150:Zymosterone 8105:Cholesterol 7865:Cholesterol 7509:glutathione 6986:1 September 6031:Amino Acids 5182:17 December 4931:3 September 4670:Amino Acids 4222:11 December 4212:PR Newswire 3921:Amino Acids 3254:60.0–4000.0 3182:150.0–250.0 2959:body fluids 2894:Breast milk 2874:Sarcoplasma 2554:beta carbon 2550:substituent 2508:) is 1.42. 2375:Formula of 2056:Cholesterol 1955:carboxylase 1604:dosage form 1494:) and gene 1436:cholesterol 1392:proteolysis 1369:translation 1294:amino acids 1194:amino acids 1147:body weight 1067:proteolysis 873:cauliflower 821:monohydrate 738:cauliflower 504: g·mol 453:100.128.078 403:CHEBI:37084 263:Identifiers 193:cholesterol 176:Metabolites 109:nasogastric 75:Other names 9946:Physiology 9890:Categories 9697:Ultratrace 9678:proteinate 9663:-carnosine 9655:-aspartate 9376:phosphates 9233:bitartrate 9187:Phosphorus 9142:levulinate 9034:glubionate 8909:Herbal tea 8863:Wheatgrass 8763:Folic acid 8665:Phosphorus 8660:Molybdenum 8509:B vitamins 8459:Probiotics 8454:Prebiotics 8434:Energy bar 8359:Ergosterol 8339:Fecosterol 8309:Sitosterol 8271:Sitosterol 8189:Zymosterol 8167:Zymostenol 8162:Zymosterol 8155:Zymosterol 8135:Lanosterol 8128:Lanosterol 8016:Carotenoid 7898:Acetyl-CoA 7789:urea cycle 7646:-Adenosyl- 7620:methionine 7605:Tiglyl-CoA 7586:isoleucine 7485:Putrescine 7480:Cadaverine 7475:Citrulline 7374:Creatinine 7262:Kynurenine 7241:tryptophan 7114:acetyl-CoA 7099:metabolism 7096:Amino acid 6546:: 508–513. 6503:McMurry JE 6407:Saytzeff A 5857:: 86–100. 5370:(5): 295. 4084:6 February 4037:ChemSpider 3980:9 November 3680:References 3487:, urinary 3474:biomarkers 3327:metabolite 3160:creatinine 3152:50.0–500.0 3130:10.0–166.0 3063:Age group 3003:creatinine 2999:micromoles 2983:micromolar 2800:Age group 2657:derivative 2530:. It is a 2526:family of 2440:acid is a 2391:acid is a 2270:α-ketoacid 2201:metabolism 2173:acetyl-CoA 2049:Mevalonate 2035:Acetyl-CoA 1998:Mevalonate 1645:Metabolism 1608:absorption 1594:following 1543:micromoles 1448:biomarkers 1394:in humans 1065:-mediated 1063:proteasome 994:-glutamine 917:sarcopenic 897:sarcopenia 877:grapefruit 742:grapefruit 509:3D model ( 497:Molar mass 363:3F752311CD 334:ChemSpider 289:CAS Number 272:IUPAC name 197:acetyl-CoA 189:mevalonate 9868:Chemistry 9823:Phase III 9811:Withdrawn 9765:carbonate 9760:aspartate 9668:gluconate 9565:gluconate 9483:-cysteine 9432:-cysteine 9346:gluconate 9331:carbonate 9321:ascorbate 9283:phosphate 9258:gluconate 9238:carbonate 9223:ascorbate 9215:Potassium 9132:glycinate 9127:gluconate 9112:carbonate 9107:aspartate 9102:ascorbate 9094:Magnesium 9074:phosphate 9069:pangamate 9044:gluconate 9009:carbonate 9004:ascorbate 8924:Nutrition 8873:Yohimbine 8868:Wolfberry 8848:Spirulina 8828:Melatonin 8803:Krill oil 8778:Glutamine 8748:Echinacea 8718:Carnitine 8670:Potassium 8655:Manganese 8650:Magnesium 8559:Biotin (B 8532:Niacin (B 8344:Episterol 7689:threonine 7505:glutamate 7470:Ornithine 7403:histidine 7389:glutamate 7216:β-Leucine 7038:US9770424 7032:US9707241 7026:US9539224 7020:US9259430 7014:US8815280 6865:Ružička L 6558:(4): 96. 6381:20 August 6329:20 August 6180:12 August 6103:"Leucine" 5718:23 August 5364:Nutrients 5207:22 August 5147:15 August 4608:: 56–87. 4403:exercise. 4187:205379191 4048:10 August 3871:22 August 3839:22 August 3342:mid-1990s 3230:5.5–234.0 3156:μmol/mmol 3060:Biofluid 3024:<20–29 2928:μmol/mmol 2775:β-hydroxy 2699:hydrolyze 2672:β-hydroxy 2580:β-hydroxy 2574:Synthesis 2517:β-Hydroxy 2481:λ 2475:25°C 2442:weak acid 2435:β-Hydroxy 2428:β-hydroxy 2402:with the 2386:β-Hydroxy 2339:Chemistry 2320:cytosolic 2112:β-hydroxy 1973:reductase 1964:hydratase 1826:(HMG-CoA) 1787:β-Hydroxy 1708:Glutamate 1701:Glutamate 1473:of human 1425:apoptosis 1398:. Unlike 1361:ribosomes 1207:and HMB). 1149:per day. 985:-arginine 911:of seven 865:asparagus 797:free acid 757:mid-1990s 730:asparagus 678:, reduce 636:β-hydroxy 251:Excretion 232:half-life 98:Routes of 9856:Medicine 9780:Vanadium 9737:fluoride 9729:Fluorine 9706:Chromium 9629:selenite 9624:selenate 9616:Selenium 9479:-acetyl- 9440:-cystine 9336:chloride 9243:chloride 9162:pidolate 9117:chloride 9029:folinate 9014:chloride 8758:Fish oil 8738:Creatine 8675:Selenium 8635:Fluorine 8620:Chromium 8489:Vitamins 8479:Vitamins 8449:Minerals 8321:instead. 8262:Nonhuman 8254:instead. 8118:Squalene 8029:Phytoene 7994:Geranyl- 7745:tyrosine 7732:fumarate 7679:Cysteine 7501:cysteine 7465:Agmatine 7456:arginine 7360:creatine 7321:pyruvate 7137:Allysine 6977:Archived 6851:24495238 6812:26271627 6710:Archived 6648:96317019 6505:(2010). 6409:(1877). 6375:Archived 6323:Archived 6204:Archived 6150:Archived 6147:-leucine 6123:Archived 6059:11120110 6051:20607321 6005:21918059 5943:Archived 5916:19211028 5871:26048279 5833:26178029 5775:26010896 5712:Archived 5691:25776302 5683:29249685 5636:29676656 5591:22657268 5583:24279396 5539:24072740 5491:27897391 5435:24336486 5396:27187465 5339:27324808 5285:28554316 5234:Archived 5173:Archived 5141:Archived 5051:25099672 4987:18173841 4888:26373270 4834:45124293 4826:25663250 4774:27934654 4700:24057808 4630:29717535 4622:27106402 4551:23551944 4467:29037326 4390:29086232 4347:28493406 4283:26169182 4179:23652097 4078:Archived 4042:Archived 3974:Archived 3949:11120110 3941:20607321 3862:Archived 3830:Archived 3800:23374455 3774:(1): 6. 3594:-leucine 3581:-leucine 3559:-leucine 3542:-leucine 3483:, serum 3392:-hydroxy 3362:See also 3020:2.1–88.5 3012:-leucine 2924:3.2–25.0 2884:4.0–10.0 2796:Biofluid 2540:hydroxyl 2333:-leucine 2250:-leucine 2238:-leucine 2225:-leucine 2211:-leucine 2097:-leucine 2087:-leucine 2007:Thiolase 1982:synthase 1844:(MG-CoA) 1835:(MC-CoA) 1807:(10–40%) 1805:in urine 1802:Excreted 1722:Pyruvate 1677:-Leucine 1519:in vitro 1504:in vitro 1492:myogenin 1479:in vitro 1405:-leucine 1367:and the 1336:-leucine 1287:; Mito: 1204:-leucine 1178:anabolic 964:HIV/AIDS 941:cachexia 925:bed rest 869:avocados 830:-leucine 817:calcium 807:calcium 734:avocados 668:HIV/AIDS 613:(verify) 298:625-08-1 116:ATC code 105:By mouth 9880:Biology 9842:Portals 9770:orotate 9752:Lithium 9647:acetate 9524:taurine 9458:sulfate 9386:sulfate 9366:nitrite 9356:lactate 9341:citrate 9288:sulfate 9268:lactate 9248:citrate 9172:taurate 9167:sulfate 9152:orotate 9137:lactate 9122:citrate 9079:sulfate 9059:lactate 9024:citrate 8999:acetate 8986:Calcium 8904:Hadacol 8858:Taurine 8808:Lingzhi 8788:Guarana 8768:Ginseng 8753:Ephedra 8615:Choline 8610:Calcium 8070:CDP-MEP 7936:Acetone 7918:HMG-CoA 7913:HMB-CoA 7890:HMG-CoA 7869:steroid 7437:proline 7356:glycine 7335:glycine 7326:citrate 7245:alanine 7177:leucine 7035:, and 6916:5656832 6771:9361403 6741:Bibcode 6230:MetaCyc 6210:24 June 5996:3192457 5949:24 June 5824:4496741 5766:4843955 5644:4991601 5482:5326814 5387:4882708 5290:groups. 5243:24 June 5098:31 July 4978:2245953 4765:5118760 4708:8688823 4542:3690694 4443:: 1–9. 4398:4284897 4338:5566641 4192:disease 4129:31 July 3791:3568064 3640:enzyme. 3616:glucose 3585:insulin 3413:name), 3350:patents 3340:in the 3303:History 3275:30350.0 3206:0–699.4 3070:Sources 2863:2.0–6.0 2807:Sources 2687:acetone 2653:racemic 2602:alcohol 2595:vicinal 2538:with a 2444:with a 2322:enzyme 2318:by the 2312:HMB-CoA 2308:HMB-CoA 2266:enzyme 2183:HMG-CoA 2168:HMG-CoA 2160:HMG-CoA 2140:HMG-CoA 2120:HMB-CoA 2013:Unknown 2000:pathway 1971:HMG-CoA 1928:HMG-CoA 1816:HMB-CoA 1772:cytosol 1747:(α-KIC) 1735:(α-KIC) 1715:Alanine 1631:kidneys 1498:(e.g., 1486:(e.g., 1409:insulin 1396:in vivo 1342:of the 1322:in vivo 1049:muscle 962:due to 923:during 887:Medical 881:catfish 861:alfalfa 811:of the 795:in the 755:in the 746:catfish 726:alfalfa 662:due to 642:, is a 532:Density 502:118.132 470:Formula 309:PubChem 185:HMG-CoA 181:HMB-CoA 18:Revigor 9806:WHO-EM 9575:Iodine 9557:Copper 9411:Sulfur 9361:malate 9298:Sodium 9273:malate 9263:iodide 9147:malate 9064:malate 8899:Enzyte 8685:Sulfur 8680:Sodium 8640:Iodine 8630:Copper 8625:Cobalt 8242:20α,22 8080:HMB-PP 8065:CDP-ME 7542:valine 7340:serine 7123:lysine 7061:(MeSH) 6945: 6914: 6849: 6810: 6769: 6762:168736 6759: 6702: 6673: 6646: 6611: 6521: 6400:Reaxys 6351: 6303:. 5.0. 6236:6 June 6170:BRENDA 6129:6 June 6115: 6057: 6049: 6003: 5993: 5914: 5869: 5831: 5821: 5773: 5763: 5689: 5681: 5642: 5634: 5589: 5581: 5537: 5489: 5479: 5433: 5394: 5384: 5337: 5283: 5133: 5089: 5049: 4985: 4975: 4918:Abbott 4886: 4832: 4824: 4772: 4762: 4706: 4698: 4628: 4620: 4549: 4539: 4465: 4396: 4388: 4345: 4335: 4281: 4185: 4177: 3947: 3939: 3798: 3788: 3572:HMB-FA 3533:HMB-FA 3520:HMB-FA 3420:, and 3251:2030.0 3158: 3101:0–19.0 3082:Units 3079:Range 3031:HMB-FA 3016:42–164 2997: 2969:, and 2961:using 2903:42–164 2835:0–10.0 2819:Units 2816:Range 2691:ketene 2600:, and 2591:alkene 2547:methyl 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