31:
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different marine animals show major differences. Wax esters of sperm whales contain C12 fatty acids and C14 fatty acid and alcohols. Monounsaturated C18 is the dominant fatty acid of most fish wax esters, with the exception of roe wax esters, which have sizeable amounts of polyunsaturated fatty acids such as
378:
has been observed to have beneficial effects on obesity-related abnormalities in rodent models of diet-induced obesity at EPA and DHA fatty acid concentrations considerably lower than the concentrations used in similar earlier studies using other sources of EPA and DHA. Taken together, based on the
227:
Beeswax is 70–80% wax esters. These esters are derived from C12-C20 fatty acids. The remaining content of beeswax are wax acids (>C20) and paraffins. In 1976, an estimated 10,000–17,000 tons were harvested. The primary use was in candles. The esters in carnauba wax consist of ca 20% cinnamic
198:
The chain lengths of fatty acids and fatty alcohols in naturally occurring wax esters vary. The fatty acids in wax esters derived from plants typically range from C12-C24, and the alcohols in plant waxes tend to be very long, typically C24-C34. The fatty acids and fatty alcohols of wax esters from
194:
centers. Saturated wax esters have higher melting points and are more likely to be solid at room temperature. Unsaturated wax esters have a lower melting point and are more likely to be liquid at room temperature. Both fatty acids and fatty alcohols may be made of different carbon chain length. In
399:
Marine wax esters have become a focus of attention due to documented positive effects on widespread medical conditions related to certain diets. Harvesting on a lower trophic level on short-lived organisms would be more sustainable and the products would be less prone to environmental toxins and
284:
are a normal part of the diet of humans as a lipid component of certain foods, including unrefined whole grain cereals, seeds, and nuts. Wax esters are also consumed in considerable amounts by certain populations that regularly eat fish roe or certain fish species. That said, wax esters are not
348:
is an attractive food fish with 5.5% fat, where 90% of the fat comes as wax esters. Consumption of this fish gives no unpleasant adverse effects, most likely due to the relatively low fat content that provides approximately 10 000 mg wax ester per 200 grams serving of fish.
642:
Cook, C. M.; Larsen, T. S.; Derrig, L. D.; Kelly, K. M.; Tande, K. S. (2016). "Wax Ester Rich Oil from the Marine
Crustacean, Calanus finmarchicus, is a Bioavailable Source of EPA and DHA for Human Consumption".
181:
369:
Studies on mice have shown that, despite consuming diets containing similar amounts of EPA and DHA, blood levels of both EPA and DHA were significantly higher in mice fed a diet supplemented with oil from
195:
the end, there are many different possible combinations of fatty acids and fatty alcohols and each combination will have a unique set of properties in terms of steric orientation and phase transition.
340:. Fillets from these fish species contain up to 20% fat, where 90% of the fat comes as wax esters, resulting in a typical intake of more than 30 000 mg wax esters from one single meal.
383:
data, animal data, and the findings of the Cook et al. study demonstrating that circulating concentrations of EPA and DHA remained elevated up to 72 h after a single serving of 4 g oil from
437:
Uwe
Wolfmeier; Hans Schmidt; Franz-Leo Heinrichs; Georg Michalczyk; Wolfgang Payer; Wolfram Dietsche; Klaus Boehlke; Gerd Hohner; Josef Wildgruber (2002). "Waxes".
688:"A wax ester and astaxanthin-rich extract from the marine copepod Calanus finmarchicus attenuates atherogenesis in female apolipoprotein E-deficient mice"
312:
provided as wax esters reaches a maximal concentration at approximately 20 h post-consumption, and may indicate delayed absorption of the fatty acids.
219:, and contain high amounts of C14 and C16, as well as 20:5n-3, 22:5n-3 and 22:6n-3 and monounsaturated C20 and C22 are the principal fatty alcohols.
320:
There has been a common understanding that wax esters are poorly absorbed by humans, partly due to outbreaks of the purgative effect named
776:"Wax esters from the marine copepod Calanus finmarchicus reduce diet-induced obesity and obesity-related metabolic disorders in mice"
476:
Hargrove, J.L. (2004). "Nutritional significance and metabolism of very long chain fatty alcohols and acids from dietary waxes".
83:
454:
352:
In 2015 a randomized, two-period crossover human study, showed that EPA and DHA from oil extracted from the small crustacean
732:"Oil from the marine zooplankton Calanus finmarchicus improves the cardiometabolic phenotype of diet-induced obese mice"
255:
contain about 52% oil, 97% of which are wax esters. These wax esters, which are monounsaturated, are very similar to
362:
could serve as a relevant source of the healthy omega-3 fatty acids EPA, DHA and SDA. 86% of the oil from
17:
191:
563:
558:
305:
273:, and fishes store low-density wax esters in their swim bladders or other tissues to provide
204:
200:
187:
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208:
8:
668:
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576:
549:
Phleger, C.F. (1998). "Buoyancy in marine fishes: direct and indirect role of lipids".
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typically consumed in appreciable quantities in diets containing many processed foods.
34:
Triacontanyl palmitate, a typical wax ester, is derived from triacontanyl alcohol and
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compared to those fed an EPA+DHA ethyl ester enriched diet. Furthermore, oil from
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have demonstrated enzymatic activity towards wax esters. Kinetic data show that
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the hydrolyzed products of wax ester digestion are most likely slowly absorbed
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67:
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62:. Wax esters are the main components of three commercially important waxes:
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Wax esters are formed by combining one fatty acid with one fatty alcohol:
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acid derivatives, which may be related to the hardness of this wax.
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have been commercialized and sold by the
Norwegian company Zooca.
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71:
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pollutants. Wax ester-based products from the small crustacean
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252:
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was highly bioavailable and the study concluded that oil from
51:
519:
Kolattukudy, P.E. (1976). "Introduction to natural waxes".
176:{\displaystyle {\ce {RCOOH + R'OH <=> RCOOR' + H2O}}}
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166:
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Bledsoe, G.E. (2003). "Caviars and fish roe products".
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439:Ullmann's Encyclopedia of Industrial Chemistry
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521:Chemistry and Biochemistry of Natural Waxes
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211:. The fatty acids of wax esters of certain
248:. In leaves, they prevent loss of water.
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27:Ester of a fatty acid and a fatty alcohol
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536:The physiology of the insect epidermis
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839:. New Zealand Institute of Chemistry
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215:largely reflects the fatty acids of
24:
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315:
222:
25:
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478:Experimental Biology and Medicine
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324:, associated with consumption of
236:Wax esters are commonly found in
834:"Studies on Wax Esters in Fish"
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136:
111:
13:
1:
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832:D. Buisson and S.F. Hannan.
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10:
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538:. CSIRO. pp. 240–251.
490:10.1177/153537020422900301
338:Lepdocybium flavobrunneum)
749:10.1017/S0007114513001839
657:10.1007/s11745-016-4189-y
608:10.1080/10408690390826545
686:Eilertsen, K.E. (2012).
534:de Renobales, M (1991).
447:10.1002/14356007.a28_103
346:Hoplostethus atlanticus)
441:. Weinheim: Wiley-VCH.
232:Other, minor wax esters
596:Crit Rev Food Sci Nutr
262:Marine organisms like
177:
39:
793:10.3945/jn.113.182501
705:10.3945/jn.111.145698
366:comes as wax esters.
240:and as a part of the
190:, and others contain
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33:
774:Hoper, A.C. (2014).
730:Hoper, A.C. (2013).
573:10.1093/icb/38.2.321
402:Calanus finmarchicus
355:Calanus finmarchicus
186:Some wax esters are
84:
742:(2013): 2186–2193.
330:Ruvettus pretiosus)
168:
122:
395:Role as a nutrient
173:
156:
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40:
786:(2014): 164–169.
698:(2012): 508–512.
651:(10): 1137–1144.
602:(2003): 317–356.
456:978-3-527-30673-2
298:carboxylesterases
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385:C. finmarchicus
376:C. finmarchicus
372:C. finmarchicus
364:C. finmarchicus
360:C. finmarchicus
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316:Bioavailability
300:that hydrolyze
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264:dinoflagellates
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223:Natural sources
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60:fatty alcohol
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841:. Retrieved
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64:carnauba wax
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280:Wax esters
213:zooplankton
192:unsaturated
843:2012-07-10
420:References
414:Keriorrhea
379:available
322:keriorrhea
289:Metabolism
251:Nuts from
246:arthropods
56:fatty acid
18:Wax esters
816:"Calanus"
736:Br J Nutr
559:CiteSeerX
257:sperm oil
238:shellfish
188:saturated
137:⇀
130:−
119:−
112:↽
44:wax ester
855:Category
802:24285691
758:23768435
714:22323762
665:27604086
624:35039858
616:12822675
506:38905297
498:14988513
408:See also
381:in vitro
275:buoyancy
150:′
99:′
50:) is an
673:3972582
581:4620147
551:Am Zool
389:in vivo
334:escolar
326:oilfish
294:Lipases
268:pelagic
242:cuticle
209:22:6n-3
205:22:5n-3
201:20:5n-3
72:beeswax
861:Esters
800:
780:J Nutr
756:
712:
692:J Nutr
671:
663:
645:Lipids
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282:per se
253:jojoba
70:, and
58:and a
837:(PDF)
669:S2CID
620:S2CID
577:JSTOR
502:S2CID
147:RCOOR
89:RCOOH
54:of a
52:ester
798:PMID
754:PMID
710:PMID
661:PMID
612:PMID
494:PMID
451:ISBN
332:and
308:and
296:and
207:and
788:doi
784:144
744:doi
740:110
700:doi
696:142
653:doi
604:doi
569:doi
486:doi
482:229
443:doi
310:DHA
306:EPA
244:of
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