1752:
1994:
47:
425:
295:
1150:
38:
633:
1130:
1236:
1744:
1090:
963:
1169:
1110:
4259:
842:
1195:, but compared with other flavonoids, their antioxidant potential is low. The ability to quench singlet oxygen seems to be in relation with the chemical structure of catechin, with the presence of the catechol moiety on ring B and the presence of a hydroxyl group activating the double bond on ring C.
3399:
Matsuda M, Otsuka Y, Jin S, Wasaki J, Watanabe J, Watanabe T, Osaki M (February 2008). "Biotransformation of (+)-catechin into taxifolin by a two-step oxidation: primary stage of (+)-catechin metabolism by a novel (+)-catechin-degrading bacteria, Burkholderia sp. KTC-1, isolated from tropical peat".
1755:
Schematic representation of (−)-epicatechin metabolism in humans as a function of time post-oral intake. SREM: structurally related (−)-epicatechin metabolites. 5C-RFM: 5-carbon ring fission metabolites. 3/1C-RFM: 3- and 1-carbon-side chain ring fission metabolites. The structures of the most
1211:
groups and the oxidation is pH-dependent. The oxidation of the catechol 3′,4′-dihydroxyl electron-donating groups occurs first, at very low positive potentials, and is a reversible reaction. The hydroxyl groups of the resorcinol moiety oxidised afterwards were shown to undergo an irreversible
1184:, putting the B-ring either in a pseudoequatorial position (E conformer) or in a pseudoaxial position (A conformer). Studies confirmed that (+)-catechin adopts a mixture of A- and E-conformers in aqueous solution and their conformational equilibrium has been evaluated to be 33:67.
2447:
Aizpurua-Olaizola O, Ormazabal M, Vallejo A, Olivares M, Navarro P, Etxebarria N, Usobiaga A (January 2015). "Optimization of supercritical fluid consecutive extractions of fatty acids and polyphenols from Vitis vinifera grape wastes".
4483:
3927:
3363:
Ottaviani JI, Momma TY, Heiss C, Kwik-Uribe C, Schroeter H, Keen CL (January 2011). "The stereochemical configuration of flavanols influences the level and metabolism of flavanols in humans and their biological activity in vivo".
2901:
Punyasiri PA, Abeysinghe IS, Kumar V, Treutter D, Duy D, Gosch C, et al. (November 2004). "Flavonoid biosynthesis in the tea plant
Camellia sinensis: properties of enzymes of the prominent epicatechin and catechin pathways".
2214:
Kríz Z, Koca J, Imberty A, Charlot A, Auzély-Velty R (July 2003). "Investigation of the complexation of (+)-catechin by beta-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques".
1871:
3681:
Khalesi S, Sun J, Buys N, Jamshidi A, Nikbakht-Nasrabadi E, Khosravi-Boroujeni H (September 2014). "Green tea catechins and blood pressure: a systematic review and meta-analysis of randomised controlled trials".
641:
1530:
4389:
2997:
Maugé C, Granier T, d'Estaintot BL, Gargouri M, Manigand C, Schmitter JM, et al. (April 2010). "Crystal structure and catalytic mechanism of leucoanthocyanidin reductase from Vitis vinifera".
4443:
613:
4473:
1645:
2021:
Due to extensive metabolism during digestion, the fate and activity of catechin metabolites responsible for this effect on blood vessels, as well as the actual mode of action, are unknown.
4448:
2697:
Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST (June 2008). "Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Açaí (
4428:
4423:
2962:
Skadhauge B, Gruber MY, Thomsen KK, Von
Wettstein D (April 1997). "Leucocyanidin Reductase Activity and Accumulation of Proanthocyanidins in Developing Legume Tissues".
707:
3478:"Proanthocyanidin synthesis and expression of genes encoding leucoanthocyanidin reductase and anthocyanidin reductase in developing grape berries and grapevine leaves"
1827:
The stereochemical configuration of catechins has a strong impact on their uptake and metabolism as uptake is highest for (−)-epicatechin and lowest for (−)-catechin.
4122:
Bais HP, Vepachedu R, Gilroy S, Callaway RM, Vivanco JM (September 2003). "Allelopathy and exotic plant invasion: from molecules and genes to species interactions".
2175:
Rinaldo D, Batista JM, Rodrigues J, Benfatti AC, Rodrigues CM, dos Santos LC, et al. (August 2010). "Determination of catechin diastereomers from the leaves of
3199:"The metabolome of [2-C](−)-epicatechin in humans: implications for the assessment of efficacy, safety, and mechanisms of action of polyphenolic bioactives"
4418:
1751:
4208:
Chen Z, Liang J, Zhang C, Rodrigues CJ (October 2006). "Epicatechin and catechin may prevent coffee berry disease by inhibition of appressorial melanization of
2293:
Tournaire C, Croux S, Maurette MT, Beck I, Hocquaux M, Braun AM, Oliveros E (August 1993). "Antioxidant activity of flavonoids: efficiency of singlet oxygen (Δ
4464:
4461:
4457:
4453:
3033:
3437:"Biooxidation of (+)-catechin and (−)-epicatechin into 3,4-dihydroxyflavan derivatives by the endophytic fungus Diaporthe sp. isolated from a tea plant"
1065:
Making reference to no particular isomer, the molecule can just be called catechin. Mixtures of the different enantiomers can be called (±)-catechin or
855:
194:
2114:. Most plants in the European ecosystem have defenses against catechin, but few plants are protected against it in the North American ecosystem where
4385:
1855:
1562:
by cinnamate 4-hydroxylase. Chalcone synthase then catalyzes the condensation of 4-hydroxycinnamoyl CoA and three molecules of malonyl-CoA to form
4412:
4406:
4173:
Yamamoto M, Nakatsuka S, Otani H, Kohmoto K, Nishimura S (June 2000). "(+)-Catechin acts as an infection-inhibiting factor in strawberry leaf".
2510:
2068:
One limited meta-analysis showed that increasing consumption of green tea and its catechins to seven cups per day provided a small reduction in
4479:
3928:"Summary Safety Review - Green tea extract-containing natural health products - Assessing the potential risk of liver injury (hepatotoxicity)"
2123:
Catechin acts as an infection-inhibiting factor in strawberry leaves. Epicatechin and catechin may prevent coffee berry disease by inhibiting
3256:"Intestinal absorption, metabolism, and excretion of (−)-epicatechin in healthy humans assessed by using an intestinal perfusion technique"
3143:
Sambandam T, Mahadevan A (January 1993). "Degradation of catechin and purification and partial characterization of catechin oxygenase from
1959:
474:
2396:
Lin YP, Chen TY, Tseng HW, Lee MH, Chen ST (June 2009). "Neural cell protective compounds isolated from
Phoenix hanceana var. formosana".
4469:
2018:
regulation in humans. Green tea catechins may improve blood pressure, especially when systolic blood pressure is above 130 mmHg.
3601:"Effects of chocolate, cocoa, and flavan-3-ols on cardiovascular health: a systematic review and meta-analysis of randomized trials"
2804:
Quinde-Axtell Z, Baik BK (December 2006). "Phenolic compounds of barley grain and their implication in food product discoloration".
1472:, which, according to one database, has the highest content (108 mg/100 g) of catechins among foods analyzed, followed by
703:
3642:"Epicatechin ingested via cocoa products reduces blood pressure in humans: a nonlinear regression model with a Bayesian approach"
3297:"Structurally related (−)-epicatechin metabolites in humans: assessment using de novo chemically synthesized authentic standards"
2839:
Kielhorn, S.; Thorngate, J. H. III (1999). "Oral sensations associated with the flavan-3-ols (+)-catechin and (−)-epicatechin".
2738:"Browning Potential, Phenolic Composition, and Polyphenoloxidase Activity of Buffer Extracts of Peach and Nectarine Skin Tissue"
782:
3877:
3844:
2946:
2149:
556:
1772:, resulting in so-called structurally related epicatechin metabolites (SREM). The main metabolic pathways for SREMs are
4291:
2769:
Gálvez MC, Barroso CG, Pérez-Bustamante JA (1994). "Analysis of polyphenolic compounds of different vinegar samples".
2369:
Osman AM, Wong KK, Fernyhough A (April 2007). "The laccase/ABTS system oxidizes (+)-catechin to oligomeric products".
1203:
Electrochemical experiments show that (+)-catechin oxidation mechanism proceeds in sequential steps, related with the
439:
850:
862:
1703:
3048:
448:
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1
37:
4263:
2057:
1792:, with only small amounts detected in plasma. The majority of dietary catechins are however metabolised by the
1711:
1669:
594:
458:
InChI=1/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1
1789:
1707:
1511:
discoloration. The taste associated with monomeric (+)-catechin or (−)-epicatechin is described as slightly
3341:
2866:
Rani A, Singh K, Ahuja PS, Kumar S (March 2012). "Molecular regulation of catechins biosynthesis in tea ".
1893:
1579:
1059:
677:
365:
290:
3065:
Arunachalam M, Mohan N, Sugadev R, Chellappan P, Mahadevan A (June 2003). "Degradation of (+)-catechin by
1993:
1660:
1555:
403:
252:
17:
695:
2029:
Catechin and its metabolites can bind tightly to red blood cells and thereby induce the development of
1920:, NADPH, and H. Its gene expression has been studied in developing grape berries and grapevine leaves.
632:
2084:
Catechins released into the ground by some plants may hinder the growth of their neighbors, a form of
2514:
302:
4053:(2018). "Nano- and micro-particles for delivery of catechins: Physical and biological performance".
3776:
Schroeter H, Heiss C, Balzer J, Kleinbongard P, Keen CL, Hollenberg NK, et al. (January 2006).
1149:
4512:
3778:"(−)-Epicatechin mediates beneficial effects of flavanol-rich cocoa on vascular function in humans"
1756:
abundant (−)-epicatechin metabolites present in the systemic circulation and in urine are depicted.
1674:
1655:
Catechin oxygenase, a key enzyme in the degradation of catechin, is present in fungi and bacteria.
1604:(PA) specific pathway. Its activity has been measured in leaves, flowers, and seeds of the legumes
1452:
1181:
731:
420:
1129:
2107:
1585:
1448:
798:
2637:
2577:
Vogiatzoglou A, Mulligan AA, Lentjes MA, Luben RN, Spencer JP, Schroeter H, et al. (2015).
785:
212:
4438:
4433:
4284:
3254:
Actis-Goretta L, Lévèques A, Rein M, Teml A, Schäfer C, Hofmann U, et al. (October 2013).
2129:
1929:
1761:
1624:
1089:
4517:
1417:
1031:-catechin. The most common epicatechin isomer is (−)-epicatechin (also known under the names
991:
655:
625:
59:
3951:
Younes M, Aggett P, Aguilar F, Crebelli R, Dusemund B, Filipič M, et al. (April 2018).
723:
4131:
3789:
3210:
3197:
Ottaviani JI, Borges G, Momma TY, Spencer JP, Keen CL, Crozier A, Schroeter H (July 2016).
2590:
2405:
2041:. This resulted in the withdrawal of the catechin-containing drug Catergen, used to treat
1630:
1412:
916:
719:
390:
382:
374:
169:
161:
2152:. Food and Agriculture Organization of the United Nations. 5 November 2011. Archived from
711:
272:
145:
8:
4328:
1797:
1665:
1578:
by flavanone 3-hydroxylase. Taxifolin is then reduced by dihydroflavanol 4-reductase and
1529:
1246:
1224:
999:
153:
135:
4135:
3793:
3533:
Friedrich W, Galensa R (2002). "Identification of a new flavanol glucoside from barley (
3377:
3313:
3296:
3214:
2594:
2409:
1109:
424:
294:
232:
4564:
4559:
4554:
4237:
4155:
4078:
4026:
4001:
3977:
3952:
3883:
3812:
3777:
3753:
3726:
3707:
3554:
3510:
3497:
3477:
3231:
3198:
3172:
3125:
2979:
2786:
2613:
2578:
2429:
2275:
2116:
2090:
2034:
1731:
1267:
3837:
Methods of
Analysis, Preclinical and Clinical Pharmacokinetics, Safety, and Toxicology
3082:
2852:
2332:
Janeiro P, Oliveira Brett AM (2004). "Catechin electrochemical oxidation mechanisms".
1848:(+)-Catechin and (−)-epicatechin are transformed by the endophytic filamentous fungus
4277:
4229:
4190:
4147:
4070:
4050:
4031:
3982:
3873:
3840:
3817:
3758:
3711:
3699:
3663:
3622:
3581:
3515:
3458:
3417:
3381:
3318:
3277:
3236:
3164:
3086:
3014:
2942:
2919:
2883:
2821:
2718:
2652:
2618:
2559:
2465:
2421:
2314:
2310:
2267:
2232:
2196:
1805:
1360:
1010:
776:
572:
4269:
4241:
4159:
4082:
3558:
3129:
2790:
2433:
2417:
2382:
2279:
46:
4221:
4182:
4139:
4062:
4021:
4013:
3972:
3964:
3887:
3865:
3835:
Martinez SE, Davies NM, Reynolds JK (2013). "Toxicology and Safety of
Flavonoids".
3807:
3797:
3748:
3738:
3691:
3653:
3612:
3599:
Hooper L, Kay C, Abdelhamid A, Kroon PA, Cohn JS, Rimm EB, Cassidy A (March 2012).
3546:
3505:
3489:
3448:
3409:
3373:
3308:
3267:
3226:
3218:
3176:
3156:
3117:
3078:
3006:
2971:
2911:
2875:
2848:
2813:
2778:
2749:
2710:
2608:
2598:
2549:
2492:
2457:
2413:
2378:
2349:
2341:
2306:
2259:
2224:
2188:
2076:
methods are under preliminary research as potential delivery systems of catechins.
1980:
1618:
1601:
1297:
1077:
879:
811:
497:
4066:
4002:"Green tea and the risk of prostate cancer: A systematic review and meta-analysis"
3901:
2603:
2069:
2042:
1809:
1773:
1687:
1612:
1606:
1559:
1426:
995:
354:
4186:
4017:
3476:
Bogs J, Downey MO, Harvey JS, Ashton AR, Tanner GJ, Robinson SP (October 2005).
2153:
4348:
3782:
Proceedings of the
National Academy of Sciences of the United States of America
3413:
2879:
2053:
2006:
Only limited evidence from dietary studies indicates that catechins may affect
1723:
1683:
1679:
1636:
1435:
1408:
1319:
979:
950:
833:
683:
4225:
3869:
3695:
3550:
3121:
3010:
2915:
2345:
760:
4548:
4363:
4343:
4333:
3968:
2754:
2737:
2675:
2038:
1917:
1801:
1695:
1597:
1544:
1536:
1481:
1348:
691:
546:
283:
4143:
3802:
3743:
3658:
3641:
3617:
3600:
3272:
3255:
2554:
2537:
2461:
4498:
4233:
4194:
4151:
4101:"Secondary Metabolites and Allelopathy in Plant Invasions: A Case Study of
4074:
4035:
3986:
3821:
3762:
3703:
3667:
3626:
3519:
3462:
3421:
3385:
3322:
3281:
3240:
3168:
3090:
3018:
2923:
2887:
2825:
2722:
2656:
2622:
2563:
2469:
2425:
2271:
2236:
2200:
2124:
2073:
2030:
2011:
1841:
1644:
1235:
1188:
1024:
975:
971:
4100:
3585:
3493:
2538:"Estimated dietary flavonoid intake and major food sources of U.S. adults"
2483:
Freudenberg K, Cox RF, Braun E (1932). "The
Catechin of the Cacao Bean1".
2318:
2094:, the spotted knapweed often studied for this behavior, releases catechin
1743:
1457:
The main dietary sources of catechins in Europe and the United States are
4533:
4338:
4309:
3725:
Aprotosoaie AC, Miron A, Trifan A, Luca VS, Costache II (December 2016).
2446:
2085:
2007:
1817:
1781:
1571:
1540:
1473:
1404:
920:
912:
715:
4000:
Guo Y, Zhi F, Chen P, Zhao K, Xiang H, Mao Q, et al. (March 2017).
2496:
1543:
through a PKSIII pathway. 4-Hydroxycinnamoyl CoA is biosynthesized from
699:
608:
Mutagenic for mammalian somatic cells, mutagenic for bacteria and yeast
4379:
4317:
3501:
3453:
3436:
3160:
2983:
2782:
2192:
2099:
2015:
1691:
1567:
1563:
1512:
1477:
1469:
1304:
1253:
1208:
983:
932:
928:
525:
303:
263:
3295:
Ottaviani JI, Momma TY, Kuhnle GK, Keen CL, Schroeter H (April 2012).
3222:
2817:
2714:
2696:
2354:
2263:
1539:
starter unit which undergoes chain extension by the addition of three
4353:
4301:
3435:
Shibuya H, Agusta A, Ohashi K, Maehara S, Simanjuntak P (July 2005).
2228:
2111:
2103:
2049:
1850:
1836:
1813:
1793:
1777:
1575:
1496:
1260:
820:
2975:
2098:
into the ground through its roots, potentially having effects as an
962:
832:
Except where otherwise noted, data are given for materials in their
3344:. Linus Pauling Institute, Oregon State University, Corvallis. 2016
2996:
2961:
1785:
1282:
1204:
994:
centers on the molecule on carbons 2 and 3. Therefore, it has four
987:
329:
3031:
1886:, respectively, whereas (−)-catechin and (+)-epicatechin with a (2
739:
193:
3064:
3032:
Arunachalam, M.; Mohan Raj, M.; Mohan, N.; Mahadevan, A. (2003).
2095:
1765:
1500:
1422:
1216:
1168:
940:
687:
341:
3775:
2900:
2638:"Cocoa flavanols - measurement, bioavailability and bioactivity"
2576:
1747:
Human metabolites of epicatechin (excluding colonic metabolites)
1507:
grain where they are the main phenolic compound responsible for
4358:
4258:
2174:
1949:
1658:
Among bacteria, degradation of (+)-catechin can be achieved by
1582:
to yield catechin. The biosynthesis of catechin is shown below
1504:
243:
4099:
Broz AK, Vivanco JM, Schultz MJ, Perry LG, Paschke MW (2006).
669:
4172:
3727:"The Cardiovascular Effects of Cocoa Polyphenols-An Overview"
3362:
3253:
2768:
1821:
1769:
1508:
1492:
1223:
system oxidizes (+)-catechin to oligomeric products of which
924:
897:
727:
223:
183:
3860:
Bode JC (1987). Okolicsányi L, Csomós G, Crepaldi G (eds.).
3639:
408:
4121:
3950:
3196:
2110:
wave through the target plant's root to kill root cells by
1699:
1462:
1242:
1220:
1023:
The most common catechin isomer is (+)-catechin. The other
665:
551:
175 to 177 °C (347 to 351 °F; 448 to 450 K)
320:
3724:
3434:
3104:
Hopper W, Mahadevan A (1997). "Degradation of catechin by
2292:
3953:"Scientific opinion on the safety of green tea catechins"
3640:
Ellinger S, Reusch A, Stehle P, Helfrich HP (June 2012).
2742:
Journal of the
American Society for Horticultural Science
1458:
1430:
900:
894:
888:
3598:
3294:
2771:
1729:
Among fungi, degradation of catechin can be achieved by
1076:
Catechin and epicatechin are the building blocks of the
4207:
4098:
1997:
Interspecies differences in (−)-epicatechin metabolism.
1978:-glucopyranoside) can be isolated from the rhizomes of
1600:
to produce (+)-catechin and is the first enzyme in the
1180:
Moreover, the flexibility of the C-ring allows for two
3834:
3680:
3475:
3398:
3071:
Biochimica et
Biophysica Acta (BBA) - General Subjects
2579:"Flavonoid intake in European adults (18 to 64 years)"
2299:
Journal of Photochemistry and Photobiology. B, Biology
2213:
938:
The name of the catechin chemical family derives from
27:
Type of natural phenol as a plant secondary metabolite
4299:
2331:
2250:
Pietta PG (July 2000). "Flavonoids as antioxidants".
903:
885:
1574:
by flavonoid 3′-hydroxylase and further oxidized to
891:
661:
4484:
3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside
4107:. In Taiz L, Zeiger E, Møller IM, Murphy A (eds.).
3402:
Biochemical and Biophysical Research Communications
2939:
Medicinal Natural Products: A Biosynthetic Approach
2865:
2482:
2368:
2060:has recommended not to exceed 800 mg per day.
882:
3862:Assessment and Management of Hepatobiliary Disease
3142:
3041:Proceedings of the Indian National Science Academy
1854:sp. into the 3,4-cis-dihydroxyflavan derivatives,
1403:(+)-Catechin and (−)-epicatechin as well as their
3192:
3190:
3188:
3186:
3149:World Journal of Microbiology & Biotechnology
2838:
2803:
2635:
2570:
1313:d : doublet, dd : doublet of doublets,
944:, which is the tannic juice or boiled extract of
211:
4546:
3532:
3356:
1698:. Protocatechuic acid and hydroxyquinol undergo
1558:forming cinnamic acid which is then oxidized to
353:
3103:
2395:
1760:Catechins are metabolised upon uptake from the
767:(+)-catechin : 10,000 mg/kg in rat (RTECS)
168:
160:
152:
144:
4055:Critical Reviews in Food Science and Nutrition
3999:
3288:
3183:
735:
4285:
3925:
2735:
2535:
1058:The different epimers can be separated using
4115:
1678:. Phloroglucinol carboxylic acid is further
1535:The biosynthesis of catechin begins with ma
1484:, obtained from the fruit of the açaí palm (
1327:2.82 (1H, dd, J = 16.0, 1.6 Hz, H-4b),
1035:-epicatechin, epicatechol, (−)-epicatechol,
3574:Yao Xue Xue Bao (Acta Pharmaceutica Sinica)
2941:(3rd ed.). UK: John Wiley & Sons.
1839:by a two-step oxidation can be achieved by
1570:by chalcone isomerase which is oxidized to
1488:), contains (+)-catechins (67 mg/kg).
1337:6.70 (1H, dd, J = 8.1, 1.8 Hz, H-6'),
1325:2.49 (1H, dd, J = 16.0, 8.6 Hz, H-4a),
4292:
4278:
4048:
3646:The American Journal of Clinical Nutrition
3605:The American Journal of Clinical Nutrition
3260:The American Journal of Clinical Nutrition
2806:Journal of Agricultural and Food Chemistry
2703:Journal of Agricultural and Food Chemistry
2645:Asia Pacific Journal of Clinical Nutrition
1890:)-phenyl group resisted the biooxidation.
1407:conjugates are ubiquitous constituents of
423:
293:
271:
4025:
3976:
3811:
3801:
3752:
3742:
3657:
3616:
3509:
3452:
3312:
3271:
3230:
2753:
2612:
2602:
2553:
2529:
2353:
389:
381:
373:
3864:. Berlin: Springer-Verlag. p. 371.
2485:Journal of the American Chemical Society
1992:
1750:
1742:
1491:Catechins are diverse among foods, from
1468:Catechins and epicatechins are found in
1234:
1167:
986:moiety while the B ring is similar to a
982:on carbon 3. The A ring is similar to a
961:
4094:
4092:
2904:Archives of Biochemistry and Biophysics
2536:Chun OK, Chung SJ, Song WO (May 2007).
1835:Biotransformation of (+)-catechin into
1738:
419:
71:)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2
14:
4547:
3441:Chemical & Pharmaceutical Bulletin
3336:
3334:
3332:
2936:
2249:
1554:-Phenylalanine is first deaminated by
1398:
284:
4273:
3839:. John Wiley & Son. p. 257.
3571:
3539:European Food Research and Technology
2670:
2668:
2666:
2106:. One hypothesis is that it causes a
1339:6.75 (1H, d, J = 8.1 Hz, H-5'),
1315:m : multiplet, s : singlet
451:Key: PFTAWBLQPZVEMU-DZGCQCFKSA-N
251:
231:
4415:(Afzelechin-3-O-β-D-glucopyranoside)
4089:
3859:
3769:
2217:Organic & Biomolecular Chemistry
2079:
2001:
1830:
1335:5.92 (1H, d, J = 2.1 Hz, H-8),
1333:5.86 (1H, d, J = 2.1 Hz, H-6),
1187:As flavonoids, catechins can act as
4444:(+)-Catechin 7-O-β-D-xylopyranoside
4409:(Afzelechin-3-O-β-D-xylopyranoside)
4111:(6th ed.). Sinauer Associates.
3674:
3378:10.1016/j.freeradbiomed.2010.11.005
3366:Free Radical Biology & Medicine
3329:
3314:10.1016/j.freeradbiomed.2011.12.010
3301:Free Radical Biology & Medicine
2676:"Polyphenols in green tea infusion"
2207:
2179:species using chiral HPLC-PAD-CD".
2120:is an invasive, uncontrolled weed.
1341:6.83 (1H, d, J = 1.8 Hz, H-2')
1331:4.56 (1H, d, J = 7.8 Hz, H-2),
461:Key: PFTAWBLQPZVEMU-DZGCQCFKBX
344:
328:
24:
3902:"Ruhen der Zulassung für Catergen"
2663:
771:3,890 mg/kg in rat (other source)
25:
4576:
4251:
2636:Kwik-Uribe C, Bektash RM (2008).
2024:
2014:which could contribute to normal
1884:)-3,4,5,7,3′,4′-hexahydroxyflavan
1868:)-3,4,5,7,3′,4′-hexahydroxyflavan
1650:
1566:. Chalcone is then isomerized to
1556:phenylalanine ammonia lyase (PAL)
1069:-catechin and (±)-epicatechin or
974:(called the A and B rings) and a
4474:(+)-catechin 7-O-α-L-arabinoside
4390:4′-O-methyl-(−)-epigallocatechin
4257:
4109:Plant Physiology and Development
2150:"Cutch and catechu plant origin"
1694:. Resorcinol is hydroxylated to
1643:
1634:. The enzyme is also present in
1528:
1230:
1148:
1128:
1108:
1088:
978:heterocycle (the C ring) with a
927:. It belongs to the subgroup of
878:
840:
631:
509:
45:
36:
4201:
4166:
4042:
3993:
3944:
3919:
3894:
3853:
3828:
3718:
3633:
3592:
3565:
3526:
3469:
3428:
3392:
3247:
3136:
3097:
3058:
3025:
2990:
2955:
2930:
2894:
2859:
2832:
2797:
2762:
2729:
2690:
2629:
2511:"Michiyo Tsujimura (1888–1969)"
2503:
2476:
2418:10.1016/j.phytochem.2009.06.006
2383:10.1016/j.enzmictec.2006.09.018
2371:Enzyme and Microbial Technology
1704:protocatechuate 3,4-dioxygenase
1672:(PGCA). It is also degraded by
1550:through the Shikimate pathway.
1523:
1172:3D view of "pseudoequatorial" (
1043:-epicatechol, epicatechin, 2,3-
836:(at 25 °C , 100 kPa).
482:Oc1ccc(cc1O)3Oc2cc(O)cc(O)c2C3O
2736:Cheng GW, Crisosto CH (1995).
2678:. Phenol-Explorer, v 3.5. 2014
2440:
2389:
2362:
2325:
2286:
2243:
2168:
2142:
2058:European Food Safety Authority
1670:phloroglucinol carboxylic acid
1176:) conformation of (+)-catechin
1080:, a type of condensed tannin.
595:Occupational safety and health
515:
503:
13:
1:
4067:10.1080/10408398.2017.1422110
3684:European Journal of Nutrition
3083:10.1016/S0304-4165(03)00077-1
2853:10.1016/S0950-3293(98)00049-4
2136:
1923:
1790:catechol-O-methyl transferase
1708:hydroxyquinol 1,2-dioxygenase
1664:. Catechin is metabolized to
1518:
1480:pod (16 mg/100 g).
1476:(25 mg/100 ml) and
1411:, and frequent components of
3926:Health Canada (2017-11-15).
3047:(4): 353–370. Archived from
3034:"Biodegradation of Catechin"
2999:Journal of Molecular Biology
2604:10.1371/journal.pone.0128132
2311:10.1016/1011-1344(93)87086-3
1894:Leucoanthocyanidin reductase
1580:leucoanthocyanidin reductase
1433:constituents, as well as in
1292:1600 cm(benzene rings)
1198:
1060:chiral column chromatography
998:. Two of the isomers are in
957:
7:
4187:10.1094/PHYTO.2000.90.6.595
4018:10.1097/MD.0000000000006426
3067:Acinetobacter calcoaceticus
2841:Food Quality and Preference
2252:Journal of Natural Products
1988:
1661:Acinetobacter calcoaceticus
1413:traditional herbal remedies
1191:when in high concentration
749:or concentration (LD, LC):
123:)-Flavan-3,3′,4′,5,7-pentol
10:
4581:
4449:Epicatechin-3′-O-glucoside
3572:Jin QD, Mu QZ (1991). "".
3414:10.1016/j.bbrc.2007.11.157
2964:American Journal of Botany
2880:10.1016/j.gene.2011.12.029
1446:
1442:
4526:
4505:
4493:
4399:
4372:
4308:
4226:10.1007/s10529-006-9135-2
3870:10.1007/978-3-642-72631-6
3696:10.1007/s00394-014-0720-1
3551:10.1007/s00217-002-0498-x
3011:10.1016/j.jmb.2010.02.002
2916:10.1016/j.abb.2004.08.003
2346:10.1016/j.aca.2004.05.038
1970:-rhamnopyranosyl-(1–4)-β-
1503:. Catechins are found in
1359:
1296:
1281:
1245:
1009:and the other two are in
830:
810:
791:
745:
612:
592:
587:
490:
470:
435:
128:
80:
58:
53:
44:
35:
4513:Epigallocatechin gallate
4373:O-methylated flavan-3ols
3969:10.2903/j.efsa.2018.5239
3106:Bradyrhizobium japonicum
2755:10.21273/JASHS.120.5.835
2542:The Journal of Nutrition
2063:
1974:-glucopyranosyl-(1–6)-β-
1675:Bradyrhizobium japonicum
1453:Phenolic content in wine
1309:(500 MHz, CD3OD):
1239:UV spectrum of catechin.
1084:Diastereoisomers gallery
678:Precautionary statements
4429:Catechin-4'-O-glucoside
4424:Catechin-3'-O-glucoside
4300:Flavan-3-ols and their
4144:10.1126/science.1083245
3803:10.1073/pnas.0510168103
3744:10.3390/diseases4040039
3659:10.3945/ajcn.111.029330
3618:10.3945/ajcn.111.023457
3273:10.3945/ajcn.113.065789
3122:10.1023/A:1008254812074
2462:10.1111/1750-3841.12715
2450:Journal of Food Science
2108:reactive oxygen species
2045:, from market in 1985.
1586:Leucocyanidin reductase
1449:Phenolic content in tea
1289:Major absorption bands
970:Catechin possesses two
4439:Catechin-7-O-glucoside
4434:Catechin-5-O-glucoside
4419:Catechin-3-O-glucoside
4210:Colletotrichum kahawae
2334:Analytica Chimica Acta
2130:Colletotrichum kahawae
1998:
1904:)-catechin, NADP and H
1804:which undergo further
1762:gastrointestinal tract
1757:
1748:
1625:Hedysarum sulfurescens
1560:4-hydroxycinnamic acid
1537:4-hydroxycinnamoyl CoA
1385:139 retro Diels–Alder
1268:Extinction coefficient
1240:
1177:
990:moiety. There are two
967:
4518:Gallocatechin gallate
4214:Biotechnology Letters
3494:10.1104/pp.105.064238
2651:(Suppl. 1): 280–283.
2555:10.1093/jn/137.5.1244
1996:
1948:can be isolated from
1754:
1746:
1425:are mostly found as
1418:Uncaria rhynchophylla
1238:
1171:
965:
769:10,000 mg/kg in mouse
75:-chromene-3,5,7-triol
4382:(3-O-methylcatechin)
4266:at Wikimedia Commons
3909:Deutsches Ärzteblatt
1870:(leucocyanidin) and
1798:gamma-valerolactones
1764:, in particular the
1739:Metabolism in humans
1631:Robinia pseudoacacia
1212:oxidation reaction.
1182:conformation isomers
1055:)-(−)-epicatechin).
917:secondary metabolite
4454:Glochiflavanoside A
4329:Epicatechin gallate
4136:2003Sci...301.1377B
4130:(5638): 1377–1380.
3794:2006PNAS..103.1024S
3215:2016NatSR...629034O
2595:2015PLoSO..1028132V
2517:on 21 November 2015
2497:10.1021/ja01344a026
2410:2009PChem..70.1173L
2156:on 10 February 2019
1666:protocatechuic acid
1399:Natural occurrences
1329:3.97 (1H, m, H-3),
1225:proanthocyanidin A2
1027:is (−)-catechin or
533: g·mol
32:
4103:Centaurea maculosa
3454:10.1248/cpb.53.866
3203:Scientific Reports
3161:10.1007/BF00656513
3145:Chaetomium cupreum
2937:Dewick PM (2009).
2783:10.1007/BF01192948
2193:10.1002/chir.20824
2117:Centaurea maculosa
2091:Centaurea maculosa
2035:haemolytic anaemia
1999:
1794:colonic microbiome
1758:
1749:
1732:Chaetomium cupreum
1515:, but not bitter.
1241:
1178:
1155:(+)-epicatechin (2
1135:(−)-epicatechin (2
1047:-epicatechin or (2
968:
863:Infobox references
173: (+), hydrate
30:
4542:
4541:
4262:Media related to
4220:(20): 1637–1640.
4061:(10): 1563–1579.
3879:978-3-642-72631-6
3846:978-0-470-57871-1
3223:10.1038/srep29034
2948:978-0-470-74167-2
2818:10.1021/jf060974w
2812:(26): 9978–9984.
2715:10.1021/jf800161u
2709:(12): 4631–4636.
2264:10.1021/np9904509
2223:(14): 2590–2595.
2080:Botanical effects
2002:Vascular function
1977:
1973:
1969:
1945:
1908:O to produce 2,3-
1831:Biotransformation
1806:biotransformation
1702:cleavage through
1553:
1547:
1396:
1395:
1078:proanthocyanidins
1072:
1068:
1042:
1038:
1034:
966:Catechin numbered
871:Chemical compound
869:
868:
777:Safety data sheet
656:Hazard statements
404:CompTox Dashboard
195:Interactive image
16:(Redirected from
4572:
4334:Epigallocatechin
4294:
4287:
4280:
4271:
4270:
4261:
4246:
4245:
4205:
4199:
4198:
4170:
4164:
4163:
4119:
4113:
4112:
4096:
4087:
4086:
4046:
4040:
4039:
4029:
3997:
3991:
3990:
3980:
3948:
3942:
3941:
3939:
3938:
3923:
3917:
3916:
3906:
3898:
3892:
3891:
3857:
3851:
3850:
3832:
3826:
3825:
3815:
3805:
3788:(4): 1024–1029.
3773:
3767:
3766:
3756:
3746:
3722:
3716:
3715:
3690:(6): 1299–1311.
3678:
3672:
3671:
3661:
3652:(6): 1365–1377.
3637:
3631:
3630:
3620:
3596:
3590:
3589:
3569:
3563:
3562:
3530:
3524:
3523:
3513:
3482:Plant Physiology
3473:
3467:
3466:
3456:
3432:
3426:
3425:
3396:
3390:
3389:
3360:
3354:
3353:
3351:
3349:
3338:
3327:
3326:
3316:
3307:(8): 1403–1412.
3292:
3286:
3285:
3275:
3251:
3245:
3244:
3234:
3194:
3181:
3180:
3140:
3134:
3133:
3101:
3095:
3094:
3062:
3056:
3055:
3053:
3038:
3029:
3023:
3022:
3005:(4): 1079–1091.
2994:
2988:
2987:
2959:
2953:
2952:
2934:
2928:
2927:
2898:
2892:
2891:
2863:
2857:
2856:
2836:
2830:
2829:
2801:
2795:
2794:
2766:
2760:
2759:
2757:
2733:
2727:
2726:
2699:Euterpe oleracea
2694:
2688:
2687:
2685:
2683:
2672:
2661:
2660:
2642:
2633:
2627:
2626:
2616:
2606:
2574:
2568:
2567:
2557:
2548:(5): 1244–1252.
2533:
2527:
2526:
2524:
2522:
2513:. Archived from
2507:
2501:
2500:
2491:(5): 1913–1917.
2480:
2474:
2473:
2456:(1): E101–E107.
2444:
2438:
2437:
2404:(9): 1173–1181.
2393:
2387:
2386:
2377:(5): 1272–1279.
2366:
2360:
2359:
2357:
2340:(1–2): 109–115.
2329:
2323:
2322:
2290:
2284:
2283:
2258:(7): 1035–1042.
2247:
2241:
2240:
2229:10.1039/B302935M
2211:
2205:
2204:
2172:
2166:
2165:
2163:
2161:
2146:
2127:melanization of
1981:Epigynum auritum
1975:
1971:
1967:
1946:-glucopyranoside
1943:
1647:
1619:Lotus uliginosus
1602:proanthocyanidin
1551:
1545:
1532:
1486:Euterpe oleracea
1243:
1152:
1132:
1112:
1092:
1070:
1066:
1040:
1036:
1032:
996:diastereoisomers
910:
909:
906:
905:
902:
899:
896:
893:
890:
887:
884:
853:
847:
844:
843:
812:Pharmacokinetics
741:
737:
733:
729:
725:
721:
717:
713:
709:
705:
701:
697:
693:
689:
685:
671:
667:
663:
635:
541:Colorless solid
532:
517:
511:
505:
498:Chemical formula
428:
427:
412:
410:
393:
385:
377:
357:
346:
332:
305:
297:
286:
275:
255:
235:
215:
197:
172:
164:
156:
148:
49:
40:
33:
29:
21:
4580:
4579:
4575:
4574:
4573:
4571:
4570:
4569:
4545:
4544:
4543:
4538:
4522:
4501:
4489:
4395:
4386:Ourateacatechin
4368:
4304:
4298:
4254:
4249:
4206:
4202:
4171:
4167:
4120:
4116:
4097:
4090:
4047:
4043:
3998:
3994:
3949:
3945:
3936:
3934:
3924:
3920:
3904:
3900:
3899:
3895:
3880:
3858:
3854:
3847:
3833:
3829:
3774:
3770:
3723:
3719:
3679:
3675:
3638:
3634:
3597:
3593:
3580:(11): 841–845.
3570:
3566:
3537:L.) and malt".
3535:Hordeum vulgare
3531:
3527:
3474:
3470:
3433:
3429:
3397:
3393:
3361:
3357:
3347:
3345:
3340:
3339:
3330:
3293:
3289:
3252:
3248:
3195:
3184:
3141:
3137:
3102:
3098:
3063:
3059:
3051:
3036:
3030:
3026:
2995:
2991:
2976:10.2307/2446026
2960:
2956:
2949:
2935:
2931:
2899:
2895:
2864:
2860:
2837:
2833:
2802:
2798:
2767:
2763:
2734:
2730:
2695:
2691:
2681:
2679:
2674:
2673:
2664:
2640:
2634:
2630:
2589:(5): e0128132.
2575:
2571:
2534:
2530:
2520:
2518:
2509:
2508:
2504:
2481:
2477:
2445:
2441:
2394:
2390:
2367:
2363:
2330:
2326:
2296:
2291:
2287:
2248:
2244:
2212:
2208:
2173:
2169:
2159:
2157:
2148:
2147:
2143:
2139:
2082:
2070:prostate cancer
2066:
2048:Catechins from
2043:viral hepatitis
2033:, resulting in
2027:
2004:
1991:
1954:Hordeum vulgare
1926:
1907:
1833:
1810:glucuronidation
1774:glucuronidation
1741:
1653:
1613:Lotus japonicus
1607:Medicago sativa
1588:(LCR) uses 2,3-
1526:
1521:
1455:
1447:Main articles:
1445:
1409:vascular plants
1401:
1390:
1388:
1386:
1384:
1383:273 water loss
1382:
1369:main fragments
1368:
1355:Other NMR data
1342:
1340:
1338:
1336:
1334:
1332:
1330:
1328:
1326:
1323:
1314:
1312:
1310:
1308:
1233:
1201:
1164:
1153:
1144:
1133:
1124:
1115:(−)-catechin (2
1113:
1104:
1095:(+)-catechin (2
1093:
1016:and are called
1005:and are called
960:
881:
877:
872:
865:
860:
859:
858: ?)
849:
845:
841:
837:
823:
803:
800:
770:
768:
764:
758:
680:
658:
644:
628:
605:
580:
578:
573:Chiral rotation
562:
530:
520:
514:
508:
500:
486:
483:
478:
477:
466:
463:
462:
459:
453:
452:
449:
443:
442:
431:
413:
406:
397:
360:
347:
335:
315:
278:
258:
238:
218:
200:
187:
176:
138:
124:
114:
108:
98:
96:
94:
92:
91:Catechinic acid
90:
88:
86:
84:
76:
28:
23:
22:
15:
12:
11:
5:
4578:
4568:
4567:
4562:
4557:
4540:
4539:
4537:
4536:
4530:
4528:
4524:
4523:
4521:
4520:
4515:
4509:
4507:
4506:Gallate esters
4503:
4502:
4497:
4495:
4491:
4490:
4488:
4487:
4477:
4467:
4451:
4446:
4441:
4436:
4431:
4426:
4421:
4416:
4410:
4403:
4401:
4397:
4396:
4394:
4393:
4383:
4376:
4374:
4370:
4369:
4367:
4366:
4361:
4356:
4351:
4349:Guibourtinidol
4346:
4341:
4336:
4331:
4326:
4320:
4314:
4312:
4306:
4305:
4297:
4296:
4289:
4282:
4274:
4268:
4267:
4253:
4252:External links
4250:
4248:
4247:
4200:
4181:(6): 595–600.
4175:Phytopathology
4165:
4114:
4088:
4041:
3992:
3943:
3918:
3893:
3878:
3852:
3845:
3827:
3768:
3717:
3673:
3632:
3611:(3): 740–751.
3591:
3576:(in Chinese).
3564:
3545:(5): 388–393.
3525:
3488:(2): 652–663.
3468:
3447:(7): 866–867.
3427:
3408:(2): 414–419.
3391:
3372:(2): 237–244.
3355:
3328:
3287:
3266:(4): 924–933.
3246:
3182:
3135:
3116:(3): 159–165.
3110:Biodegradation
3096:
3077:(3): 261–265.
3057:
3054:on 2012-03-16.
3024:
2989:
2970:(4): 494–503.
2954:
2947:
2929:
2893:
2874:(2): 205–210.
2858:
2847:(2): 109–116.
2831:
2796:
2761:
2748:(5): 835–838.
2728:
2689:
2662:
2628:
2569:
2528:
2502:
2475:
2439:
2398:Phytochemistry
2388:
2361:
2324:
2305:(3): 205–215.
2297:) quenching".
2294:
2285:
2242:
2206:
2187:(8): 726–733.
2167:
2140:
2138:
2135:
2081:
2078:
2065:
2062:
2031:autoantibodies
2026:
2025:Adverse events
2023:
2003:
2000:
1990:
1987:
1986:
1985:
1957:
1925:
1922:
1905:
1832:
1829:
1802:hippuric acids
1740:
1737:
1724:maleyl acetate
1720:-muconic acid
1688:dehydroxylated
1684:phloroglucinol
1680:decarboxylated
1652:
1651:Biodegradation
1649:
1637:Vitis vinifera
1548:-phenylalanine
1525:
1522:
1520:
1517:
1444:
1441:
1436:Vitis vinifera
1400:
1397:
1394:
1393:
1380: : 291.0
1370:
1364:
1363:
1357:
1356:
1352:
1351:
1345:
1344:
1317:
1301:
1300:
1294:
1293:
1290:
1286:
1285:
1279:
1278:
1275:
1264:
1263:
1257:
1250:
1249:
1232:
1229:
1200:
1197:
1166:
1165:
1154:
1147:
1145:
1134:
1127:
1125:
1114:
1107:
1105:
1094:
1087:
1085:
1073:-epicatechin.
1039:-acacatechin,
980:hydroxyl group
959:
956:
951:Acacia catechu
946:Mimosa catechu
870:
867:
866:
861:
839:
838:
834:standard state
831:
828:
827:
824:
819:
816:
815:
808:
807:
804:
801:administration
797:
794:
793:
789:
788:
780:
773:
772:
765:
756:
754:
751:
750:
743:
742:
708:P305+P351+P338
681:
676:
673:
672:
659:
654:
651:
650:
645:
640:
637:
636:
629:
624:
621:
620:
610:
609:
606:
603:
600:
599:
590:
589:
585:
584:
581:
576:
571:
568:
567:
564:
560:
553:
552:
549:
543:
542:
539:
535:
534:
528:
522:
521:
518:
512:
506:
501:
496:
493:
492:
488:
487:
485:
484:
481:
473:
472:
471:
468:
467:
465:
464:
460:
457:
456:
454:
450:
447:
446:
438:
437:
436:
433:
432:
430:
429:
416:
414:
402:
399:
398:
396:
395:
387:
379:
370:
368:
362:
361:
359:
358:
350:
348:
340:
337:
336:
334:
333:
325:
323:
317:
316:
314:
313:
309:
307:
299:
298:
288:
280:
279:
277:
276:
268:
266:
260:
259:
257:
256:
248:
246:
240:
239:
237:
236:
228:
226:
220:
219:
217:
216:
208:
206:
202:
201:
199:
198:
190:
188:
181:
178:
177:
175:
174:
166:
158:
150:
141:
139:
134:
131:
130:
126:
125:
93:Catechuic acid
82:
78:
77:
62:
56:
55:
51:
50:
42:
41:
26:
9:
6:
4:
3:
2:
4577:
4566:
4563:
4561:
4558:
4556:
4553:
4552:
4550:
4535:
4532:
4531:
4529:
4525:
4519:
4516:
4514:
4511:
4510:
4508:
4504:
4500:
4496:
4492:
4485:
4481:
4478:
4475:
4471:
4468:
4466:
4463:
4459:
4455:
4452:
4450:
4447:
4445:
4442:
4440:
4437:
4435:
4432:
4430:
4427:
4425:
4422:
4420:
4417:
4414:
4413:Arthromerin B
4411:
4408:
4407:Arthromerin A
4405:
4404:
4402:
4398:
4391:
4387:
4384:
4381:
4378:
4377:
4375:
4371:
4365:
4364:Robinetinidol
4362:
4360:
4357:
4355:
4352:
4350:
4347:
4345:
4344:Gallocatechin
4342:
4340:
4337:
4335:
4332:
4330:
4327:
4325:(Epicatechin)
4324:
4321:
4319:
4316:
4315:
4313:
4311:
4307:
4303:
4295:
4290:
4288:
4283:
4281:
4276:
4275:
4272:
4265:
4260:
4256:
4255:
4243:
4239:
4235:
4231:
4227:
4223:
4219:
4215:
4211:
4204:
4196:
4192:
4188:
4184:
4180:
4176:
4169:
4161:
4157:
4153:
4149:
4145:
4141:
4137:
4133:
4129:
4125:
4118:
4110:
4106:
4104:
4095:
4093:
4084:
4080:
4076:
4072:
4068:
4064:
4060:
4056:
4052:
4045:
4037:
4033:
4028:
4023:
4019:
4015:
4012:(13): e6426.
4011:
4007:
4003:
3996:
3988:
3984:
3979:
3974:
3970:
3966:
3963:(4): e05239.
3962:
3958:
3954:
3947:
3933:
3932:www.canada.ca
3929:
3922:
3914:
3910:
3903:
3897:
3889:
3885:
3881:
3875:
3871:
3867:
3863:
3856:
3848:
3842:
3838:
3831:
3823:
3819:
3814:
3809:
3804:
3799:
3795:
3791:
3787:
3783:
3779:
3772:
3764:
3760:
3755:
3750:
3745:
3740:
3736:
3732:
3728:
3721:
3713:
3709:
3705:
3701:
3697:
3693:
3689:
3685:
3677:
3669:
3665:
3660:
3655:
3651:
3647:
3643:
3636:
3628:
3624:
3619:
3614:
3610:
3606:
3602:
3595:
3587:
3583:
3579:
3575:
3568:
3560:
3556:
3552:
3548:
3544:
3540:
3536:
3529:
3521:
3517:
3512:
3507:
3503:
3499:
3495:
3491:
3487:
3483:
3479:
3472:
3464:
3460:
3455:
3450:
3446:
3442:
3438:
3431:
3423:
3419:
3415:
3411:
3407:
3403:
3395:
3387:
3383:
3379:
3375:
3371:
3367:
3359:
3343:
3337:
3335:
3333:
3324:
3320:
3315:
3310:
3306:
3302:
3298:
3291:
3283:
3279:
3274:
3269:
3265:
3261:
3257:
3250:
3242:
3238:
3233:
3228:
3224:
3220:
3216:
3212:
3208:
3204:
3200:
3193:
3191:
3189:
3187:
3178:
3174:
3170:
3166:
3162:
3158:
3154:
3150:
3146:
3139:
3131:
3127:
3123:
3119:
3115:
3111:
3107:
3100:
3092:
3088:
3084:
3080:
3076:
3072:
3068:
3061:
3050:
3046:
3042:
3035:
3028:
3020:
3016:
3012:
3008:
3004:
3000:
2993:
2985:
2981:
2977:
2973:
2969:
2965:
2958:
2950:
2944:
2940:
2933:
2925:
2921:
2917:
2913:
2909:
2905:
2897:
2889:
2885:
2881:
2877:
2873:
2869:
2862:
2854:
2850:
2846:
2842:
2835:
2827:
2823:
2819:
2815:
2811:
2807:
2800:
2792:
2788:
2784:
2780:
2776:
2772:
2765:
2756:
2751:
2747:
2743:
2739:
2732:
2724:
2720:
2716:
2712:
2708:
2704:
2700:
2693:
2677:
2671:
2669:
2667:
2658:
2654:
2650:
2646:
2639:
2632:
2624:
2620:
2615:
2610:
2605:
2600:
2596:
2592:
2588:
2584:
2580:
2573:
2565:
2561:
2556:
2551:
2547:
2543:
2539:
2532:
2516:
2512:
2506:
2498:
2494:
2490:
2486:
2479:
2471:
2467:
2463:
2459:
2455:
2451:
2443:
2435:
2431:
2427:
2423:
2419:
2415:
2411:
2407:
2403:
2399:
2392:
2384:
2380:
2376:
2372:
2365:
2356:
2351:
2347:
2343:
2339:
2335:
2328:
2320:
2316:
2312:
2308:
2304:
2300:
2289:
2281:
2277:
2273:
2269:
2265:
2261:
2257:
2253:
2246:
2238:
2234:
2230:
2226:
2222:
2218:
2210:
2202:
2198:
2194:
2190:
2186:
2182:
2178:
2171:
2155:
2151:
2145:
2141:
2134:
2132:
2131:
2126:
2121:
2119:
2118:
2113:
2109:
2105:
2101:
2097:
2093:
2092:
2087:
2077:
2075:
2071:
2061:
2059:
2055:
2051:
2046:
2044:
2040:
2039:renal failure
2036:
2032:
2022:
2019:
2017:
2013:
2009:
1995:
1983:
1982:
1965:
1961:
1958:
1956:L.) and malt.
1955:
1951:
1947:
1941:
1938:)-Catechin-7-
1937:
1933:
1928:
1927:
1921:
1919:
1918:leucocyanidin
1915:
1911:
1903:
1899:
1896:(LAR) uses (2
1895:
1891:
1889:
1885:
1883:
1879:
1875:
1869:
1867:
1863:
1859:
1853:
1852:
1846:
1844:
1843:
1838:
1828:
1825:
1823:
1819:
1815:
1811:
1807:
1803:
1799:
1795:
1791:
1787:
1783:
1779:
1775:
1771:
1768:, and in the
1767:
1763:
1753:
1745:
1736:
1734:
1733:
1727:
1725:
1721:
1719:
1715:
1709:
1705:
1701:
1697:
1696:hydroxyquinol
1693:
1689:
1685:
1681:
1677:
1676:
1671:
1667:
1663:
1662:
1656:
1648:
1646:
1641:
1639:
1638:
1633:
1632:
1627:
1626:
1621:
1620:
1615:
1614:
1609:
1608:
1603:
1599:
1598:leucocyanidin
1595:
1591:
1587:
1583:
1581:
1577:
1573:
1569:
1565:
1561:
1557:
1549:
1542:
1538:
1533:
1531:
1516:
1514:
1510:
1506:
1502:
1498:
1494:
1489:
1487:
1483:
1479:
1475:
1471:
1466:
1464:
1460:
1454:
1450:
1440:
1438:
1437:
1432:
1428:
1424:
1420:
1419:
1414:
1410:
1406:
1392:
1379:
1375:
1371:
1366:
1365:
1362:
1358:
1354:
1353:
1350:
1349:Carbon-13 NMR
1347:
1346:
1343:
1321:
1318:
1316:
1306:
1303:
1302:
1299:
1295:
1291:
1288:
1287:
1284:
1280:
1276:
1273:
1269:
1266:
1265:
1262:
1258:
1255:
1252:
1251:
1248:
1244:
1237:
1231:Spectral data
1228:
1226:
1222:
1218:
1213:
1210:
1206:
1196:
1194:
1190:
1185:
1183:
1175:
1170:
1162:
1158:
1151:
1146:
1142:
1138:
1131:
1126:
1122:
1118:
1111:
1106:
1102:
1098:
1091:
1086:
1083:
1082:
1081:
1079:
1074:
1063:
1061:
1056:
1054:
1050:
1046:
1030:
1026:
1021:
1019:
1015:
1014:configuration
1013:
1008:
1004:
1003:configuration
1002:
997:
993:
989:
985:
981:
977:
973:
972:benzene rings
964:
955:
953:
952:
947:
943:
942:
936:
934:
930:
926:
922:
918:
914:
908:
876:
864:
857:
852:
835:
829:
825:
822:
818:
817:
813:
809:
805:
802:
796:
795:
792:Pharmacology
790:
787:
784:
781:
778:
775:
774:
766:
762:
753:
752:
748:
744:
682:
679:
675:
674:
660:
657:
653:
652:
649:
646:
643:
639:
638:
634:
630:
627:
623:
622:
618:
616:
611:
607:
602:
601:
597:
596:
591:
586:
582:
574:
570:
569:
565:
558:
555:
554:
550:
548:
547:Melting point
545:
544:
540:
537:
536:
529:
527:
524:
523:
502:
499:
495:
494:
489:
480:
479:
476:
469:
455:
445:
444:
441:
434:
426:
422:
421:DTXSID3022322
418:
417:
415:
405:
401:
400:
392:
388:
384:
380:
376:
372:
371:
369:
367:
364:
363:
356:
352:
351:
349:
343:
339:
338:
331:
327:
326:
324:
322:
319:
318:
311:
310:
308:
306:
301:
300:
296:
292:
289:
287:
285:ECHA InfoCard
282:
281:
274:
270:
269:
267:
265:
262:
261:
254:
250:
249:
247:
245:
242:
241:
234:
230:
229:
227:
225:
222:
221:
214:
210:
209:
207:
204:
203:
196:
192:
191:
189:
185:
180:
179:
171:
167:
163:
159:
155:
151:
147:
143:
142:
140:
137:
133:
132:
127:
122:
118:
112:
106:
102:
97:Dexcyanidanol
79:
74:
70:
66:
61:
57:
52:
48:
43:
39:
34:
19:
4534:Thearubigins
4499:Phylloflavan
4480:Symplocoside
4322:
4310:Flavan-3-ols
4264:(+)-Catechin
4217:
4213:
4209:
4203:
4178:
4174:
4168:
4127:
4123:
4117:
4108:
4102:
4058:
4054:
4044:
4009:
4005:
3995:
3960:
3957:EFSA Journal
3956:
3946:
3935:. Retrieved
3931:
3921:
3912:
3908:
3896:
3861:
3855:
3836:
3830:
3785:
3781:
3771:
3734:
3730:
3720:
3687:
3683:
3676:
3649:
3645:
3635:
3608:
3604:
3594:
3577:
3573:
3567:
3542:
3538:
3534:
3528:
3485:
3481:
3471:
3444:
3440:
3430:
3405:
3401:
3394:
3369:
3365:
3358:
3346:. Retrieved
3342:"Flavonoids"
3304:
3300:
3290:
3263:
3259:
3249:
3206:
3202:
3155:(1): 37–44.
3152:
3148:
3144:
3138:
3113:
3109:
3105:
3099:
3074:
3070:
3066:
3060:
3049:the original
3044:
3040:
3027:
3002:
2998:
2992:
2967:
2963:
2957:
2938:
2932:
2910:(1): 22–30.
2907:
2903:
2896:
2871:
2867:
2861:
2844:
2840:
2834:
2809:
2805:
2799:
2777:(1): 29–31.
2774:
2770:
2764:
2745:
2741:
2731:
2706:
2702:
2698:
2692:
2680:. Retrieved
2648:
2644:
2631:
2586:
2582:
2572:
2545:
2541:
2531:
2519:. Retrieved
2515:the original
2505:
2488:
2484:
2478:
2453:
2449:
2442:
2401:
2397:
2391:
2374:
2370:
2364:
2337:
2333:
2327:
2302:
2298:
2288:
2255:
2251:
2245:
2220:
2216:
2209:
2184:
2180:
2176:
2170:
2158:. Retrieved
2154:the original
2144:
2128:
2125:appressorial
2122:
2115:
2089:
2083:
2074:Nanoparticle
2067:
2047:
2028:
2020:
2012:vasodilation
2005:
1979:
1963:
1962:(catechin-3-
1953:
1939:
1935:
1931:
1913:
1909:
1901:
1897:
1892:
1887:
1881:
1877:
1873:
1865:
1861:
1857:
1849:
1847:
1842:Burkholderia
1840:
1834:
1826:
1759:
1730:
1728:
1717:
1713:
1673:
1659:
1657:
1654:
1642:
1635:
1629:
1623:
1617:
1611:
1605:
1593:
1589:
1584:
1541:malonyl-CoAs
1534:
1527:
1524:Biosynthesis
1490:
1485:
1467:
1456:
1434:
1416:
1402:
1381:
1377:
1373:
1324:
1307:
1271:
1227:is a dimer.
1214:
1202:
1192:
1189:antioxidants
1186:
1179:
1173:
1160:
1156:
1140:
1136:
1120:
1116:
1100:
1096:
1075:
1064:
1057:
1052:
1048:
1044:
1028:
1025:stereoisomer
1022:
1017:
1011:
1006:
1000:
976:dihydropyran
969:
949:
945:
939:
937:
915:, a type of
874:
873:
746:
647:
614:
604:Main hazards
593:
253:ChEMBL206452
129:Identifiers
120:
116:
110:
104:
100:
87:(+)-catechin
81:Other names
72:
68:
64:
4339:Fisetinidol
4051:Augustin MA
3915:(38): 2706.
2521:10 November
2086:allelopathy
2054:hepatotoxic
2010:-dependent
2008:endothelium
1818:methylation
1782:methylation
1686:, which is
1572:eriodictyol
1474:prune juice
1405:gallic acid
1018:epicatechin
929:polyphenols
921:antioxidant
913:flavan-3-ol
761:median dose
747:Lethal dose
642:Signal word
598:(OHS/OSH):
538:Appearance
491:Properties
291:100.005.297
233:CHEBI:15600
18:Epicatechin
4549:Categories
4494:Acetylated
4400:Glycosides
4380:Meciadanol
4318:Afzelechin
4302:glycosides
3937:2022-05-06
3069:MTC 127".
2682:1 November
2355:10316/5128
2137:References
2100:antibiotic
2016:blood flow
1960:Epigeoside
1924:Glycosides
1712:β-carboxy-
1692:resorcinol
1668:(PCA) and
1568:naringenin
1519:Metabolism
1513:astringent
1478:broad bean
1421:. The two
1415:, such as
1367:Masses of
1311:Reference
1305:Proton NMR
1254:Lambda-max
1209:resorcinol
984:resorcinol
933:flavonoids
919:providing
783:sciencelab
626:Pictograms
526:Molar mass
391:FHB0GX3D44
383:8R1V1STN48
375:5J4Y243W61
264:ChemSpider
182:3D model (
170:88191-48-4
162:18829-70-4
136:CAS Number
107:)-Catechin
89:D-Catechin
85:Cyanidanol
83:Cianidanol
60:IUPAC name
4565:Nutrition
4560:Catechols
4555:Flavanols
4354:Mesquitol
3737:(4): 39.
3712:206969226
3209:: 29034.
2701:Mart.)".
2181:Chirality
2177:Byrsonima
2112:apoptosis
2104:herbicide
2050:green tea
1851:Diaporthe
1837:taxifolin
1814:sulfation
1788:group by
1778:sulfation
1700:intradiol
1640:(grape).
1576:taxifolin
1497:green tea
1199:Oxidation
958:Chemistry
923:roles in
821:Excretion
799:Routes of
786:AppliChem
732:P403+P233
724:P337+P313
720:P332+P313
704:P304+P340
700:P302+P352
617:labelling
394: (−)
386: (+)
378: (±)
312:205-825-1
304:EC Number
165: (−)
157: (+)
149: (±)
146:7295-85-4
113:-Catechin
31:Catechin
4470:Polydine
4323:Catechin
4242:30593181
4234:16955359
4195:18944538
4160:26483595
4152:12958360
4083:29522787
4075:29345975
4036:28353571
4006:Medicine
3987:32625874
3822:16418281
3763:28933419
3731:Diseases
3704:24861099
3668:22552030
3627:22301923
3559:84221785
3520:16169968
3463:15997157
3422:18068670
3386:21074608
3323:22240152
3282:23864538
3241:27363516
3169:24419836
3130:41221044
3091:12787923
3019:20138891
2924:15464723
2888:22226811
2826:17177530
2791:91784893
2723:18522407
2657:18296356
2623:26010916
2583:PLOS ONE
2564:17449588
2470:25471637
2434:28636157
2426:19628235
2280:23310671
2272:10924197
2237:12956082
2201:20143413
2056:and the
1989:Research
1786:catechol
1710:to form
1564:chalcone
1482:Açaí oil
1465:fruits.
1439:grapes.
1372:ESI-MS
1205:catechol
1193:in vitro
1007:catechin
988:catechol
875:Catechin
588:Hazards
154:154-23-4
95:Cianidol
4132:Bibcode
4124:Science
4049:Ye JH,
4027:5380255
3978:7009618
3888:3167832
3813:1327732
3790:Bibcode
3754:5456324
3586:1823978
3511:1255985
3502:4281902
3348:24 July
3232:4929566
3211:Bibcode
3177:1257624
2984:2446026
2614:4444122
2591:Bibcode
2406:Bibcode
2319:8229463
2160:26 July
2096:isomers
2052:can be
1820:in the
1784:of the
1766:jejunum
1501:vinegar
1493:peaches
1443:In food
1423:isomers
1322: :
1217:laccase
941:catechu
931:called
856:what is
854: (
826:Urines
648:Warning
583:+14.0°
566:276 nm
531:290.271
342:PubChem
4359:Oritin
4240:
4232:
4193:
4158:
4150:
4081:
4073:
4034:
4024:
3985:
3975:
3886:
3876:
3843:
3820:
3810:
3761:
3751:
3710:
3702:
3666:
3625:
3584:
3557:
3518:
3508:
3500:
3461:
3420:
3384:
3321:
3280:
3239:
3229:
3175:
3167:
3128:
3089:
3017:
2982:
2945:
2922:
2886:
2824:
2789:
2721:
2655:
2621:
2611:
2562:
2468:
2432:
2424:
2317:
2278:
2270:
2235:
2199:
1950:barley
1872:(−)-(2
1856:(+)-(2
1628:, and
1505:barley
1247:UV-Vis
992:chiral
954:L.f).
925:plants
851:verify
848:
779:(SDS)
557:UV-vis
475:SMILES
330:C06562
244:ChEMBL
213:B02102
205:3DMet
54:Names
4527:Misc.
4238:S2CID
4156:S2CID
4079:S2CID
3905:(PDF)
3884:S2CID
3708:S2CID
3555:S2CID
3498:JSTOR
3173:S2CID
3126:S2CID
3052:(PDF)
3037:(PDF)
2980:JSTOR
2787:S2CID
2641:(PDF)
2430:S2CID
2276:S2CID
2064:Other
1912:-3,4-
1910:trans
1822:liver
1770:liver
1592:-3,4-
1590:trans
1509:dough
1470:cocoa
1461:and
1427:cacao
1277:4.01
1270:(log
1001:trans
911:is a
806:Oral
440:InChI
224:ChEBI
184:JSmol
111:trans
4230:PMID
4191:PMID
4148:PMID
4071:PMID
4032:PMID
3983:PMID
3874:ISBN
3841:ISBN
3818:PMID
3759:PMID
3700:PMID
3664:PMID
3623:PMID
3582:PMID
3516:PMID
3459:PMID
3418:PMID
3382:PMID
3350:2016
3319:PMID
3278:PMID
3237:PMID
3165:PMID
3087:PMID
3075:1621
3015:PMID
2943:ISBN
2920:PMID
2884:PMID
2868:Gene
2822:PMID
2719:PMID
2684:2014
2653:PMID
2619:PMID
2560:PMID
2523:2015
2466:PMID
2422:PMID
2315:PMID
2268:PMID
2233:PMID
2197:PMID
2162:2016
2037:and
1845:sp.
1816:and
1800:and
1780:and
1722:and
1706:and
1499:and
1463:pome
1451:and
1429:and
1391:147
1389:165
1387:123
1259:276
1221:ABTS
1215:The
1207:and
740:P501
736:P405
728:P362
716:P321
712:P312
696:P280
692:P271
688:P264
684:P261
670:H335
666:H319
662:H315
366:UNII
355:9064
321:KEGG
273:8711
109:2,3-
4222:doi
4212:".
4183:doi
4140:doi
4128:301
4063:doi
4022:PMC
4014:doi
3973:PMC
3965:doi
3866:doi
3808:PMC
3798:doi
3786:103
3749:PMC
3739:doi
3692:doi
3654:doi
3613:doi
3547:doi
3543:214
3506:PMC
3490:doi
3486:139
3449:doi
3410:doi
3406:366
3374:doi
3309:doi
3268:doi
3227:PMC
3219:doi
3157:doi
3147:".
3118:doi
3108:".
3079:doi
3045:B69
3007:doi
3003:397
2972:doi
2912:doi
2908:431
2876:doi
2872:495
2849:doi
2814:doi
2779:doi
2775:199
2750:doi
2746:120
2711:doi
2609:PMC
2599:doi
2550:doi
2546:137
2493:doi
2458:doi
2414:doi
2379:doi
2350:hdl
2342:doi
2338:518
2307:doi
2260:doi
2225:doi
2189:doi
2102:or
2072:.
1966:-α-
1942:-β-
1914:cis
1796:to
1718:cis
1714:cis
1690:to
1682:to
1594:cis
1495:to
1459:tea
1431:tea
1298:NMR
1045:cis
1029:ent
1012:cis
615:GHS
561:max
409:EPA
345:CID
4551::
4460:,
4456:,
4236:.
4228:.
4218:28
4216:.
4189:.
4179:90
4177:.
4154:.
4146:.
4138:.
4126:.
4091:^
4077:.
4069:.
4059:59
4057:.
4030:.
4020:.
4010:96
4008:.
4004:.
3981:.
3971:.
3961:16
3959:.
3955:.
3930:.
3913:82
3911:.
3907:.
3882:.
3872:.
3816:.
3806:.
3796:.
3784:.
3780:.
3757:.
3747:.
3733:.
3729:.
3706:.
3698:.
3688:53
3686:.
3662:.
3650:95
3648:.
3644:.
3621:.
3609:95
3607:.
3603:.
3578:26
3553:.
3541:.
3514:.
3504:.
3496:.
3484:.
3480:.
3457:.
3445:53
3443:.
3439:.
3416:.
3404:.
3380:.
3370:50
3368:.
3331:^
3317:.
3305:52
3303:.
3299:.
3276:.
3264:98
3262:.
3258:.
3235:.
3225:.
3217:.
3205:.
3201:.
3185:^
3171:.
3163:.
3151:.
3124:.
3112:.
3085:.
3073:.
3043:.
3039:.
3013:.
3001:.
2978:.
2968:84
2966:.
2918:.
2906:.
2882:.
2870:.
2845:10
2843:.
2820:.
2810:54
2808:.
2785:.
2773:.
2744:.
2740:.
2717:.
2707:56
2705:.
2665:^
2649:17
2647:.
2643:.
2617:.
2607:.
2597:.
2587:10
2585:.
2581:.
2558:.
2544:.
2540:.
2489:54
2487:.
2464:.
2454:80
2452:.
2428:.
2420:.
2412:.
2402:70
2400:.
2375:40
2373:.
2348:.
2336:.
2313:.
2303:19
2301:.
2274:.
2266:.
2256:63
2254:.
2231:.
2219:.
2195:.
2185:22
2183:.
2133:.
2088:.
1934:,3
1930:(2
1900:,3
1880:,4
1876:,3
1864:,4
1860:,3
1824:.
1812:,
1808:,
1776:,
1735:.
1726:.
1622:,
1616:,
1610:,
1361:MS
1283:IR
1274:)
1261:nm
1256::
1159:,3
1139:,3
1119:,3
1099:,3
1071:DL
1067:DL
1062:.
1051:,3
1020:.
935:.
898:tʃ
814::
757:50
755:LD
738:,
734:,
730:,
726:,
722:,
718:,
714:,
710:,
706:,
702:,
698:,
694:,
690:,
686:,
668:,
664:,
619::
563:)
559:(λ
513:14
507:15
119:,3
115:(2
103:,3
99:(2
67:,3
63:(2
4486:)
4482:(
4476:)
4472:(
4465:D
4462:C
4458:B
4392:)
4388:(
4293:e
4286:t
4279:v
4244:.
4224::
4197:.
4185::
4162:.
4142::
4134::
4105:"
4085:.
4065::
4038:.
4016::
3989:.
3967::
3940:.
3890:.
3868::
3849:.
3824:.
3800::
3792::
3765:.
3741::
3735:4
3714:.
3694::
3670:.
3656::
3629:.
3615::
3588:.
3561:.
3549::
3522:.
3492::
3465:.
3451::
3424:.
3412::
3388:.
3376::
3352:.
3325:.
3311::
3284:.
3270::
3243:.
3221::
3213::
3207:6
3179:.
3159::
3153:9
3132:.
3120::
3114:8
3093:.
3081::
3021:.
3009::
2986:.
2974::
2951:.
2926:.
2914::
2890:.
2878::
2855:.
2851::
2828:.
2816::
2793:.
2781::
2758:.
2752::
2725:.
2713::
2686:.
2659:.
2625:.
2601::
2593::
2566:.
2552::
2525:.
2499:.
2495::
2472:.
2460::
2436:.
2416::
2408::
2385:.
2381::
2358:.
2352::
2344::
2321:.
2309::
2295:g
2282:.
2262::
2239:.
2227::
2221:1
2203:.
2191::
2164:.
1984:.
1976:D
1972:D
1968:L
1964:O
1952:(
1944:D
1940:O
1936:S
1932:R
1916:-
1906:2
1902:S
1898:R
1888:S
1882:R
1878:R
1874:R
1866:S
1862:S
1858:R
1716:,
1596:-
1552:L
1546:L
1378:z
1376:/
1374:m
1320:δ
1272:ε
1219:/
1174:E
1163:)
1161:S
1157:S
1143:)
1141:R
1137:R
1123:)
1121:R
1117:S
1103:)
1101:S
1097:R
1053:R
1049:R
1041:L
1037:L
1033:L
948:(
907:/
904:n
901:ɪ
895:ɪ
892:t
889:æ
886:k
883:ˈ
880:/
846:N
763:)
759:(
579:)
577:D
575:(
519:6
516:O
510:H
504:C
411:)
407:(
186:)
121:S
117:R
105:S
101:R
73:H
69:S
65:R
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
-catechin-from-xtal-3D-bs-17.png)
