401:
266:
571:
566:
24:
33:
722:
3743:
42:
3730:
1065:
802:
727:
726:
1518:
Santos, Sónia A. O.; Freire, Carmen S. R.; Domingues, M. Rosário M.; Silvestre, Armando J. D.; Pascoal Neto, Carlos (2011). "Characterization of
Phenolic Components in Polar Extracts of Eucalyptus globulus Labill. Bark by High-Performance Liquid Chromatography–Mass Spectrometry".
725:
1346:
antagonist (antithiamine factor), there have been no known ill effects of caffeic acid in humans. Also, caffeic acid treatment attenuated lipopolysaccharide (LPS)-induced sickness behaviour in experimental animals by decreasing both peripheral and central
5686:
2305:"Carcinogenicity of antioxidants BHA, caffeic acid, sesamol, 4-methoxyphenol and catechol at low doses, either alone or in combination, and modulation of their effects in a rat medium-term multi-organ carcinogenesis model"
4722:
4712:
2242:
Rajendra Prasad, N.; Karthikeyan, A.; Karthikeyan, S.; Reddy, B. V. (Mar 2011). "Inhibitory effect of caffeic acid on cancer cell proliferation by oxidative mechanism in human HT-1080 fibrosarcoma cell line".
579:
5274:
5246:
5117:
7091:
6640:
6210:
6620:
6770:
4398:
1142:
546:
6780:
6740:
6585:
6580:
6595:
5691:
2129:
Fulcrand, Hélène; Cheminat, Annie; Brouillard, Raymond; Cheynier, Véronique (1994). "Characterization of compounds obtained by chemical oxidation of caffeic acid in acidic conditions".
6895:
1202:
leads to the formation of dimers with a furan structure (isomers of 2,5-(3′,4′-dihydroxyphenyl)tetrahydrofuran 3,4-dicarboxylic acid). Caffeic acid can also be polymerized using the
5667:
6377:
5848:
3910:
6988:
6200:
1587:
Choudhary, M. Iqbal; Naheed, Nadra; Abbaskhan, Ahmed; Musharraf, Syed Ghulam; Siddiqui, Hina; Atta-Ur-Rahman (2008). "Phenolic and other constituents of fresh water fern
4051:
4046:
1326:
in those same rats. No significant effect was noted otherwise. Caffeic acid is listed under some Hazard Data sheets as a potential carcinogen, as has been listed by the
665:
6850:
6625:
6382:
4486:
4358:
4322:
728:
1634:
Lee, Y.-S.; Kang, Y.-H.; Jung, J.-Y.; Lee, Sanghyun; Ohuchi, Kazuo; Shin, Kuk Hyun; Kang, Il-Jun; Park, Jung Han Yoon; Shin, Hyun-Kyung; Soon, Sung (October 2008).
6760:
6605:
6175:
4378:
4354:
4096:
4020:
5437:
5793:
5373:
4109:
1679:
Pirjo, Mittila; Kumpulainen, Jorma (19 June 2002). "Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection".
942:
at 63.1-96.0 mg per 100 ml and red wine at 2 mg per 100 ml. It is found at relatively high levels in herbs of the mint family, especially
7421:
6665:
1768:
Zheng, Wei; Wang, Shiow Y (15 January 2003). "Oxygen radical absorbing capacity of phenolics in blueberries, cranberries, chokeberries, and lingonberries".
5582:
5236:
5160:
6250:
6230:
4418:
4374:
4233:
4229:
4225:
4221:
3493:
2362:
1554:
Khoo, Cheang S.; Sullivan, Shaun; Kazzem, Magdy; Lamin, Franklin; Singh, Swastika; Nang, Marnilar; Low, Mitchell; Suresh, Harsha; Lee, Samiuela (2014).
6170:
815:
6915:
6494:
4727:
4590:
4564:
4318:
4299:
5635:
4304:
6815:
6335:
6220:
5188:
4279:
4275:
4271:
4267:
4263:
4259:
4255:
4251:
4246:
4242:
4238:
2502:
Basu, Mallik S; et al. (3 Sep 2016). "Caffeic acid attenuates lipopolysaccharide-induced sickness behaviour and neuroinflammation in mice".
750:
2582:
Beavis, R. C.; Chait, B. T. (Dec 1989). "Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins".
6810:
6805:
6630:
6447:
6392:
5913:
5798:
5681:
5676:
5331:
5178:
4479:
4443:
4309:
4294:
4284:
3781:
6489:
6320:
6315:
5823:
5818:
5813:
5808:
5740:
5735:
5311:
1260:
studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human
7225:
6800:
6590:
6499:
6108:
5760:
5715:
5165:
4934:
4914:
4909:
4899:
4879:
4864:
4854:
4663:
4633:
4608:
4289:
1177:
450:
1957:
6720:
6680:
6600:
6472:
6372:
6260:
5341:
5284:
4939:
4874:
4869:
4859:
4758:
4753:
4748:
4673:
4653:
4628:
4618:
4613:
4603:
4598:
4580:
3693:
2373:
1383:
1327:
7013:
7008:
6998:
6910:
6880:
6875:
6870:
6865:
6860:
6855:
6730:
6725:
6710:
6705:
6700:
6695:
6690:
6685:
6537:
6412:
6387:
6305:
6300:
6295:
6290:
6285:
6255:
6118:
6063:
6008:
6003:
5993:
5988:
5923:
5898:
5775:
5770:
5765:
5198:
5122:
5012:
5007:
4924:
4894:
4849:
4844:
4839:
4658:
4648:
4643:
4638:
1897:
Quinde-Axtell, Zory; Baik, Byung-Kee (2006). "Phenolic
Compounds of Barley Grain and Their Implication in Food Product Discoloration".
6790:
743:
7018:
6830:
6058:
6053:
5336:
5107:
4949:
4919:
4668:
4472:
2019:
1291:
production by more than 95 percent. The studies are the first to show that oxidative stress that would otherwise trigger or enhance
6890:
6885:
6785:
6715:
6437:
6432:
6427:
6422:
6417:
6280:
6240:
6048:
6043:
5575:
5548:
5321:
5269:
5231:
5203:
5102:
5092:
4884:
661:
6825:
6755:
6504:
6467:
6397:
6215:
3463:
151:
6509:
2747:
2571:. Imaging and Photographic Technology Department, School of Photographic Arts and Sciences, Rochester Institute of Technology.
7116:
7038:
6975:
1319:. In the same study, high doses of combined antioxidants, including caffeic acid, showed a significant decrease in growth of
302:
7526:
7516:
1078:
526:
5568:
1312:, and other experiments show carcinogenic effects. Oral administration of high doses of caffeic acid in rats has caused
810:
7506:
5938:
5918:
3774:
3642:
1184:
acid have a protective effect on browning and disappearance of caffeic acid. This browning is due to the conversion of
1097:. However, the EC number for this purported enzyme was deleted in 2007, as no evidence has emerged for its existence.
1556:"The Liquid Chromatographic Determination of Chlorogenic and Caffeic Acids in Xu Duan (Dipsacus asperoides) Raw Herb"
1331:
415:
5516:
5022:
4959:
4786:
4707:
2661:
822:
4702:
4559:
1041:, all of which are significant building blocks in lignin. The transformation to ferulic acid is catalyzed by the
736:
32:
5356:
7511:
4772:
4717:
41:
2102:
Cilliers, Johannes J. L.; Singleton, Vernon L. (1990). "Caffeic acid autoxidation and the effects of thiols".
6745:
3905:
3767:
3093:
2802:
2377:
7486:
5541:
5256:
5218:
4191:
1105:
1056:
1045:
623:
358:
261:
6750:
6650:
5079:
379:
2628:
2207:-Caffeoylshikimic acid (dactylifric acid) and its isomers, a new class of enzymic browning substrates".
649:
570:
6958:
6795:
6195:
3889:
3884:
3879:
3647:
3427:
3073:
2165:
1412:
1407:
633:
565:
5501:
203:
23:
4683:
4540:
4101:
3361:
1225:
987:
273:
3256:
1068:
In plants, caffeic acid (middle) is formed from 4-hydroxycinnamic acid (left) and is transformed to
396:
5447:
5415:
5294:
3422:
3391:
2782:
2699:
1138:
693:
2463:"Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats"
1932:
7391:
7341:
6190:
5780:
5710:
5602:
5383:
5193:
4526:
4509:
2545:
1021:(esterified through a side chain alcohol). This hydroxylation produces the caffeic acid ester of
3417:
2337:
7401:
7366:
7351:
7199:
6820:
6635:
6235:
6205:
6153:
5908:
5725:
4366:
4157:
3859:
3703:
3141:
2995:
2927:
1961:
1364:
1203:
7446:
7416:
7396:
7376:
7346:
6645:
6615:
6225:
6185:
5705:
5608:
4515:
3934:
3508:
3103:
3039:
1496:
1297:
aflatoxin production can be stymied by caffeic acid. This opens the door to use as a natural
593:
558:
54:
3371:
3151:
2286:
685:
223:
7456:
7426:
7371:
7241:
6765:
6670:
6547:
6525:
6265:
5853:
5843:
5496:
5142:
3791:
3668:
3271:
2807:
2767:
2704:
2654:
2591:
2415:
2138:
1600:
862:
681:
367:
87:
2344:
2168:(2005). "Peroxidase-Catalyzed in Situ Polymerization of Surface Orientated Caffeic Acid".
2027:
1858:
Berté, Kleber A. S. (2011). "Chemical
Composition and Antioxidant Activity of Yerba-Mate (
1480:
673:
8:
7451:
6940:
6735:
6542:
5745:
4030:
3708:
3566:
3088:
2855:
2684:
1242:
899:
669:
126:
119:
109:
3458:
3261:
2595:
2419:
2142:
1604:
400:
265:
183:
7521:
6964:
6148:
5650:
5594:
4501:
4176:
3713:
2970:
2942:
2827:
2740:
2735:
2527:
2268:
2079:
2050:
1835:
1804:
1745:
1293:
1124:
979:
947:
163:
3526:
3181:
3116:
2438:
2403:
2150:
7293:
6519:
5150:
4370:
3652:
3621:
3597:
3518:
3276:
3078:
2832:
2757:
2725:
2709:
2694:
2689:
2607:
2519:
2484:
2443:
2326:
2260:
2224:
2220:
2185:
2084:
2001:
1914:
1879:
1840:
1785:
1750:
1696:
1661:
1616:
1536:
1500:
1458:
1397:
Isomers with the same molecular formula and in the hydroxycinammic acids family are:
1386:
1284:
1207:
1173:
1034:
926:
3171:
3156:
2272:
1714:
1612:
7160:
7149:
6362:
6355:
6325:
5888:
5838:
5511:
5068:
4464:
4071:
4014:
3683:
3556:
3346:
3341:
3029:
2990:
2599:
2531:
2511:
2474:
2461:
Gonthier, M.-P.; Verny, M.-A.; Besson, C.; Rémésy, C.; Scalbert, A. (1 June 2003).
2433:
2423:
2316:
2252:
2216:
2177:
2146:
2111:
2074:
2066:
1991:
1906:
1871:
1830:
1820:
1777:
1740:
1715:"Showing all foods in which the polyphenol Caffeic acid is found - Phenol-Explorer"
1688:
1651:
1608:
1567:
1528:
1492:
1448:
1431:
Gould, Kevin S.; Markham, Kenneth R.; Smith, Richard H.; Goris, Jessica J. (2000).
1237:
1233:
1199:
1026:
1018:
955:
920:
838:
772:
473:
347:
3453:
3241:
2055:-Quinones formed in plant extracts. Their reactions with amino acids and peptides"
861:. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a
7106:
6514:
6482:
6457:
6028:
5968:
5730:
5591:
4394:
4350:
4197:
4186:
3939:
3846:
3838:
3830:
3759:
3747:
3614:
3311:
2876:
2862:
2817:
2752:
2647:
2515:
1453:
1432:
1320:
1305:
1038:
615:
3161:
3146:
2564:
1803:
Bojić, Mirza; Haas, Vicente Simon; Šarić, Darija; Maleš, Željan (4 April 2018).
1728:
962:(at about 22 mg per 100 g). Caffeic acid occurs at moderate levels in
7193:
7096:
7056:
6018:
5973:
5521:
5041:
4994:
4986:
4978:
4821:
4813:
4805:
4735:
4572:
4498:
4181:
3944:
3678:
3478:
3473:
3448:
3396:
3381:
3321:
3306:
3221:
3216:
3201:
3083:
3051:
2883:
2837:
2812:
2797:
2791:
2762:
2730:
2303:
Hirose, M.; Takesada, Y.; Tanaka, H.; Tamano, S.; Kato, T.; Shirai, T. (1998).
1368:
1309:
982:(141 mg per 100 g). It is also quite high in the South American herb
963:
959:
793:
637:
3186:
3176:
2321:
2304:
2256:
7500:
7183:
6340:
6098:
6033:
5863:
5560:
5491:
4453:
4448:
4152:
4147:
4141:
4136:
4127:
4063:
3873:
3812:
3734:
3698:
3546:
3483:
3136:
3126:
3121:
2965:
2955:
2868:
2847:
1401:
1308:
of caffeic acid have mixed results. Some studies have shown that it inhibits
1022:
1014:
1010:
780:
776:
645:
516:
254:
3166:
2479:
2462:
2279:
978:(at about 1 mg per 100 g). It occurs at remarkably high levels in
653:
424:
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
7466:
7406:
7303:
7288:
7283:
7262:
7210:
7101:
7071:
7028:
6569:
6103:
6013:
5958:
5948:
5326:
4314:
4216:
3929:
3561:
3541:
3386:
3376:
3291:
3281:
3056:
3046:
2603:
2523:
2488:
2428:
2404:"Caffeic acid metabolism by gnotobiotic rats and their intestinal bacteria"
2264:
2189:
2005:
1918:
1883:
1844:
1789:
1700:
1665:
1620:
1540:
1504:
1462:
1264:
1157:
1113:
1069:
1030:
990:
938:
Free caffeic acid can be found in a variety of beverages, including brewed
874:
870:
434:
InChI=1/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
2611:
2447:
2330:
2241:
2228:
2088:
1996:
1979:
1950:
1825:
1754:
1572:
1555:
749:
7278:
7235:
7178:
7173:
7129:
7086:
7051:
6935:
6840:
6442:
6133:
6113:
6093:
6078:
6073:
6023:
5893:
5873:
5803:
5788:
5619:
5506:
5155:
4944:
4889:
4495:
4006:
3688:
3488:
3301:
3266:
3246:
3206:
3034:
3002:
2985:
2922:
2842:
2822:
1805:"Determination of Flavonoids, Phenolic Acids, and Xanthines in Mate Tea (
1271:
1161:
967:
784:
677:
2115:
1656:
1635:
735:
657:
243:
7298:
7257:
7230:
7215:
7205:
7061:
7023:
6930:
6660:
6452:
6367:
6245:
6138:
6123:
5983:
5943:
5928:
5858:
5828:
5755:
5463:
5400:
5137:
4929:
4904:
4434:
3965:
3960:
3673:
3592:
3531:
3356:
3336:
3326:
3296:
3236:
3226:
3191:
2980:
2889:
1376:
1339:
1185:
983:
873:
functional groups. It is found in all plants as an intermediate in the
742:
496:
292:
274:
214:
5179:
2181:
2070:
1910:
1875:
1781:
1692:
1532:
7386:
7336:
7252:
7220:
7076:
7003:
6993:
6905:
6845:
6835:
6655:
6610:
6407:
6180:
6088:
6083:
6068:
5953:
5903:
5878:
5750:
5700:
5655:
5316:
5241:
5132:
5097:
3609:
3536:
3503:
3498:
3468:
3401:
3366:
3196:
3022:
2950:
1316:
1298:
1288:
1287:
activity. Caffeic acid outperformed the other antioxidants, reducing
1192:
1112:
is an enzyme responsible for the transformation of caffeic acid into
951:
629:
792:
Except where otherwise noted, data are given for materials in their
7361:
7356:
7247:
6920:
6477:
5998:
5978:
5883:
5720:
5468:
5432:
5346:
5279:
5170:
5127:
4834:
4623:
4040:
3231:
3111:
3068:
3063:
3007:
2917:
2907:
1372:
1360:
1348:
1343:
1335:
1256:
1254:
Caffeic acid has a variety of potential pharmacological effects in
1181:
1169:
913:
886:
708:
536:
327 nm and a shoulder at c. 295 nm in acidified methanol
322:
234:
3251:
2128:
1862:
A. St.-Hil., Aquifoliaceae) Extract as
Obtained by Spray Drying".
701:
150:
7470:
7441:
7411:
7381:
7331:
7081:
7066:
6925:
6675:
6554:
6532:
6330:
5868:
5640:
5623:
3551:
3443:
3211:
3131:
2932:
1733:
Iarc
Monographs on the Evaluation of Carcinogenic Risks to Humans
1586:
1313:
1279:
971:
882:
641:
506:
334:
1334:("possibly carcinogenic to humans"). More recent data show that
1198:. Chemical oxidation of caffeic acid in acidic conditions using
7436:
7431:
7143:
6350:
6345:
6310:
6038:
5405:
5208:
5062:
3729:
3571:
3351:
3012:
2960:
2777:
2670:
2565:"A Use for that Last Cup of Coffee: Film and Paper Development"
2164:
Xu, Peng; Uyama, Hiroshi; Whitten, James E.; Kobayashi, Shiro;
1261:
1082:
1042:
994:
939:
904:
878:
866:
194:
1517:
1064:
607:
7117:
7039:
6976:
6900:
6462:
6402:
3604:
3576:
3331:
3316:
3286:
3017:
2975:
1323:
1165:
975:
954:(at about 20 mg per 100 g), and in spices, such as
943:
689:
174:
140:
1978:
Olthof, M. R.; Hollman, P. C.; Katan, M. B. (January 2001).
384:
6559:
6270:
5963:
5933:
3626:
603:
521:
223 to 225 °C (433 to 437 °F; 496 to 498 K)
313:
2302:
1980:"Chlorogenic acid and caffeic acid are absorbed in humans"
1141:
is an enzyme that uses caffeic acid and oxygen to produce
2639:
2460:
998:
611:
5023:
4960:
4787:
1636:"Protein glycation inhibitors from the fruiting body of
2163:
1958:"Dr. Duke's Phytochemical and Ethnobotanical Databases"
1553:
5184:
4773:
2203:
Maier, V. P.; Metzler, D. M.; Huber, A. F. (1964). "3-
1430:
1351:
levels along with oxidative stress inflicted by LPS.
5357:
5257:
5219:
4494:
599:
5080:
2209:
1802:
1479:Boerjan, Wout; Ralph, John; Baucher, Marie (2003).
1478:
301:
5687:4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil
3789:
1977:
1433:"Functional role of anthocyanins in the leaves of
4684:
4541:
2401:
2202:
2101:
1896:
1371:. The developing chemistry is similar to that of
1342:of caffeic acid. Other than caffeic acid being a
7498:
5448:
5416:
5295:
1678:
993:and HPLC ). It is also found at lower levels in
346:
5384:
4527:
2408:Proceedings of the National Academy of Sciences
1973:
1971:
1283:. Caffeic acid also shows immunomodulatory and
724:
125:
118:
6154:
5590:
1633:
918:. It can also be found in the freshwater fern
697:
397:DTXSID901316055 DTXSID5020231, DTXSID901316055
7122:Tooltip Plasma membrane monoamine transporter
7044:Tooltip Equilibrative nucleoside transporters
6981:Tooltip Concentrative nucleoside transporters
5576:
4480:
3775:
2655:
1359:Caffeic acid may be the active ingredient in
1338:in the rats' guts may alter the formation of
1059:(CAPE) are produced in many kinds of plants.
2287:"Nuts' New Aflatoxin Fighter: Caffeic Acid?"
1968:
4200:(ester with 3,4-dihydroxyphenyllactic acid)
4160:(caftaric acid conjugated with glutathione)
2633:Caffeic Acid as Carbocyclic Carboxylic Acid
2581:
2575:
2569:Technical Photographic Chemistry 1995 Class
2374:International Agency for Research on Cancer
1627:
1328:International Agency for Research on Cancer
5583:
5569:
5517:5-HPETE (arachidonic acid 5-hydroperoxide)
4487:
4473:
3782:
3768:
2662:
2648:
2363:"Agents Classified by the IARC Monographs"
1864:Journal of Agricultural and Food Chemistry
1813:Journal of Analytical Methods in Chemistry
1521:Journal of Agricultural and Food Chemistry
1301:by supplementing trees with antioxidants.
399:
264:
222:
96:)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid
77:)-3-(3,4-dihydroxyphenyl)-2-propenoic acid
2478:
2437:
2427:
2320:
2298:
2296:
2078:
2048:
1995:
1834:
1824:
1767:
1744:
1655:
1571:
1474:
1472:
1452:
1267:cell line has recently been established.
897:Caffeic acid can be found in the bark of
366:
7161:
5031:Tooltip Cysteinyl leukotriene receptor E
4968:Tooltip Cysteinyl leukotriene receptor 2
4795:Tooltip Cysteinyl leukotriene receptor 1
3694:Gustav III of Sweden's coffee experiment
1644:Biological & Pharmaceutical Bulletin
1497:10.1146/annurev.arplant.54.031902.134938
1063:
81:3-(3,4-Dihydroxyphenyl)-2-propenoic acid
58:3-(3,4-Dihydroxyphenyl)-2-propenoic acid
3464:Coffee ceremony of Ethiopia and Eritrea
2402:Peppercorn, M. A.; Goldman, P. (1972).
1933:"Red Clover Benefits & Information"
1093:-DOPA) to produce trans-caffeate and NH
395:
242:
7499:
4778:Tooltip Cysteinyl leukotriene receptor
2748:List of countries by coffee production
2293:
1469:
933:
892:
255:
5564:
4468:
3763:
2643:
1857:
986:(150 mg per 100 g based on
885:and its residues. It is unrelated to
881:, one of the principal components of
427:Key: QAIPRVGONGVQAS-DUXPYHPUSA-N
202:
182:
5366:Tooltip Leukotriene B4 ω-hydroxylase
5262:Tooltip Arachidonate 15-lipoxygenase
5224:Tooltip Arachidonate 12-lipoxygenase
2562:
2501:
1100:
1079:Dihydroxyphenylalanine ammonia-lyase
5085:Tooltip Arachidonate 5-lipoxygenase
1363:, a do-it-yourself black-and-white
1123:-diphenols are rapidly oxidized by
437:Key: QAIPRVGONGVQAS-DUXPYHPUBE
337:
321:
13:
6543:Tetramethylpyrazine (ligustrazine)
3643:United States Barista Championship
1009:Caffeic acid is biosynthesized by
720:
14:
7538:
5497:γ-Linolenic acid (gamolenic acid)
5151:Meclofenamic acid (meclofenamate)
4692:Tooltip Leukotriene B4 receptor 2
4549:Tooltip Leukotriene B4 receptor 1
2621:
1133:
865:. The molecule consists of both
5456:Tooltip Leukotriene D4 hydrolase
5425:Tooltip Leukotriene C4 hydrolase
5304:Tooltip Leukotriene A4 hydrolase
3742:
3741:
3728:
1055:Caffeic acid and its derivative
800:
569:
564:
40:
31:
22:
5549:Prostanoid signaling modulators
5393:Tooltip Leukotriene C4 synthase
4532:Tooltip Leukotriene B4 receptor
2556:
2538:
2495:
2454:
2395:
2355:
2235:
2196:
2157:
2122:
2095:
2042:
2012:
1925:
1890:
1851:
1796:
1761:
1613:10.1016/j.phytochem.2007.10.028
1382:It is also used as a matrix in
1249:
1156:Caffeic acid is susceptible to
1004:
796:(at 25 °C , 100 kPa).
79:3,4-Dihydroxybenzeneacrylicacid
6159:Tooltip Adenosine triphosphate
1721:
1707:
1672:
1580:
1547:
1511:
1485:Annual Review of Plant Biology
1441:Journal of Experimental Botany
1424:
1:
7487:Receptor/signaling modulators
5849:8-Phenyl-1,3-dipropylxanthine
5542:Receptor/signaling modulators
3911:3,4,5-Trihydroxycinnamic acid
3906:2,4,5-Trihydroxycinnamic acid
3094:Single-serve coffee container
2349:IARC Summary & Evaluation
2151:10.1016/S0031-9422(00)94790-3
1418:
1354:
1220:
4192:Caffeic acid phenethyl ester
3876:(2,4-dihydroxycinnamic acid)
3870:(3,4-dihydroxycinnamic acid)
2516:10.1016/j.neulet.2016.08.044
2221:10.1016/0006-291x(64)90241-4
1404:(2,4-dihydroxycinnamic acid)
1057:caffeic acid phenethyl ester
966:(8 mg per 100 g),
7:
7527:Vinylogous carboxylic acids
7517:Xanthine oxidase inhibitors
4043:(1,5-dicaffeoylquinic acid)
2584:Rapid Commun. Mass Spectrom
1240:substrates found in dates (
10:
7543:
6989:6-Hydroxy-7-methoxyflavone
5696:-ethylcarboxamidoadenosine
3890:3,5-Dihydroxycinnamic acid
3885:2,5-Dihydroxycinnamic acid
3880:2,3-Dihydroxycinnamic acid
3648:World Barista Championship
3074:Neapolitan flip coffee pot
2669:
1454:10.1093/jexbot/51.347.1107
1413:2,5-Dihydroxycinnamic acid
1408:2,3-Dihydroxycinnamic acid
1392:
501:180.16 g/mol
60:3,4-Dihydroxycinnamic acid
7507:IARC Group 2B carcinogens
7480:
7321:
7271:
7159:
7142:
7115:
7037:
6974:
6957:
6568:
6147:
6132:
5649:
5618:
5601:
5533:
5481:
5446:
5414:
5382:
5355:
5293:
5255:
5217:
5078:
5061:
5021:
4958:
4785:
4771:
4682:
4539:
4525:
4508:
4431:
4411:
4387:
4343:
4336:
4207:
4167:
4144:(dicaffeoyltartaric acid)
4126:
4089:
4060:
4052:3,5-dicaffeoylquinic acid
4047:3,4-dicaffeoylquinic acid
4003:
3992:
3985:
3978:
3953:
3919:
3898:
3858:
3822:Monohydroxycinnamic acids
3821:
3805:
3798:
3722:
3661:
3635:
3585:
3517:
3436:
3410:
3102:
2941:
2900:
2776:
2718:
2677:
2257:10.1007/s11010-010-0655-7
2049:Pierpoint, W. S. (1969).
1560:ISRN Analytical Chemistry
1119:Caffeic acid and related
1029:. It is the precursor to
988:thin-layer chromatography
790:
761:
545:
540:
466:
458:O=C(O)\C=C\c1cc(O)c(O)cc1
446:
411:
102:
86:
53:
48:
39:
30:
21:
7166:Tooltip Xanthine oxidase
4105:-Coumaric acid glucoside
3899:Trihydroxycinnamic acids
2700:International Coffee Day
1139:Caffeate 3,4-dioxygenase
624:Precautionary statements
6756:UDP-N-acetylglucosamine
5502:Dihomo-γ-linolenic acid
4208:Caffeoyl phenylethanoid
4078:-caffeoylshikimic acid)
4017:(3-caffeoylquinic acid)
3860:Dihydroxycinnamic acids
3494:Historical coffeehouses
2322:10.1093/carcin/19.1.207
1236:) and its isomers, are
7200:Cinnamomum osmophloeum
5909:Choline theophyllinate
4158:Grape reaction product
4097:Ferulic acid glucoside
4021:Cryptochlorogenic acid
3704:Coffee vending machine
2928:Furan-2-ylmethanethiol
2604:10.1002/rcm.1290031207
2546:"Caffenol-C-M, recipe"
2429:10.1073/pnas.69.6.1413
1365:photographic developer
1230:-caffeoylshikimic acid
1204:horseradish peroxidase
1073:
731:
7512:Hydroxycinnamic acids
6443:Opiranserin (VVZ-149)
5784:-Cyclopentyladenosine
5438:Serine-borate complex
4604:CGS-23131 (LY-223982)
4323:2′-Acetylverbascoside
4037:-Caffeoylquinic acid)
4027:-caffeoylquinic acid)
3935:5-Hydroxyferulic acid
3792:hydroxycinnamic acids
3509:Viennese coffee house
3040:Karlsbad coffee maker
2480:10.1093/jn/133.6.1853
1481:"Lignin biosynthesis"
1143:3-(2-carboxyethenyl)-
1067:
730:
7242:Pistacia integerrima
6548:Ligusticum wallichii
6526:Ligusticum wallichii
5854:8-Phenyltheophylline
5844:8-Chlorotheophylline
5794:Neladenoson dalanate
5374:17-Octadecynoic acid
5144:Hypericum perforatum
3669:Coffee and doughnuts
3272:Indian filter coffee
2705:Single-origin coffee
2504:Neuroscience Letters
2467:Journal of Nutrition
1130:in tissue extracts.
1081:was presumed to use
1025:, which converts to
924:and in the mushroom
863:hydroxycinnamic acid
713:(fire diamond)
130: (non-specific)
88:Preferred IUPAC name
5469:Ubenimex (bestatin)
5347:Ubenimex (bestatin)
4403:-4″-Triferulic acid
4379:8,8′-Diferulic acid
4367:8,5′-Diferulic acid
4355:5,5′-Diferulic acid
4031:Neochlorogenic acid
3709:Used coffee grounds
2596:1989RCMS....3..432B
2420:1972PNAS...69.1413P
2176:(33): 11745–11753.
2143:1994PChem..35..499F
2116:10.1021/jf00099a002
2104:J. Agric. Food Chem
2024:www.chem.qmul.ac.uk
1997:10.1093/jn/131.1.66
1899:J. Agric. Food Chem
1860:Ilex paraguariensis
1826:10.1155/2013/658596
1807:Ilex paraguariensis
1657:10.1248/bpb.31.1968
1605:2008PChem..69.1018C
1573:10.1155/2014/968314
1332:Group 2B carcinogen
1270:Caffeic acid is an
1243:Phoenix dactylifera
934:Occurrences in food
900:Eucalyptus globulus
893:Natural occurrences
164:Beilstein Reference
18:
5237:3-Methoxytropolone
5161:N-Stearoyldopamine
4419:Tetraferulic acids
4363:-4′-Diferulic acid
4177:Caffeoylmalic acid
3714:Sustainable coffee
3411:Organization lists
3372:Rüdesheimer Kaffee
3152:Café com cheirinho
2741:Sustainable coffee
2736:Shade-grown coffee
2383:on 25 October 2011
1937:indigo-herbs.co.uk
1447:(347): 1107–1115.
1294:Aspergillus flavus
1217:oxidizing system.
1128:-diphenol oxidases
1110:-methyltransferase
1074:
1050:-methyltransferase
823:Infobox references
762:Related compounds
732:
16:
7494:
7493:
7317:
7316:
7294:Mycophenolic acid
7153:
7138:
7137:
6968:
6953:
6952:
6949:
6948:
6520:Angelica sinensis
5612:
5558:
5557:
5477:
5476:
5146:(St. John's Wort)
5072:
5057:
5056:
5053:
5052:
4767:
4766:
4519:
4462:
4461:
4427:
4426:
4332:
4331:
4222:Calceolarioside A
4170:with caffeic acid
4122:
4121:
4113:
4085:
4084:
3974:
3973:
3923:-methylated forms
3757:
3756:
3735:Coffee portal
3653:World Brewers Cup
3277:Ipoh white coffee
2758:Coffee wastewater
2726:Coffee production
2710:Third-wave coffee
2563:Williams, Scott.
2182:10.1021/ja051637r
2071:10.1042/bj1120609
1911:10.1021/jf060974w
1905:(26): 9978–9984.
1876:10.1021/jf2008343
1870:(10): 5523–5527.
1782:10.1021/jf020728u
1770:J Agric Food Chem
1739:: 115–134. 1993.
1693:10.1021/jf020028p
1681:J Agric Food Chem
1650:(10): 1968–1972.
1638:Phellinus linteus
1533:10.1021/jf201801q
1527:(17): 9386–9393.
1435:Quintinia serrata
1387:mass spectrometry
1285:anti-inflammatory
1174:thioglycolic acid
1101:Biotransformation
1092:
1086:
1035:coniferyl alcohol
927:Phellinus linteus
841:with the formula
831:Chemical compound
829:
828:
768:Related compounds
594:Hazard statements
380:CompTox Dashboard
152:Interactive image
7534:
7167:
7163:
7157:
7156:
7147:
7123:
7119:
7045:
7041:
6982:
6978:
6972:
6971:
6962:
6356:Rheum officinale
6160:
6156:
6145:
6144:
5889:Caffeine citrate
5839:7-Methylxanthine
5672:-methyladenosine
5616:
5615:
5606:
5585:
5578:
5571:
5562:
5561:
5512:Arachidonic acid
5457:
5453:
5426:
5422:
5394:
5390:
5367:
5363:
5305:
5301:
5263:
5259:
5225:
5221:
5185:
5181:
5086:
5082:
5076:
5075:
5066:
5032:
5028:
4969:
4965:
4796:
4792:
4783:
4782:
4779:
4775:
4693:
4689:
4550:
4546:
4537:
4536:
4533:
4529:
4523:
4522:
4513:
4489:
4482:
4475:
4466:
4465:
4395:Triferulic acids
4341:
4340:
4337:Oligomeric forms
4111:
4072:Dactylifric acid
4015:Chlorogenic acid
4001:
4000:
3990:
3989:
3983:
3982:
3824:(Coumaric acids)
3803:
3802:
3784:
3777:
3770:
3761:
3760:
3748:Category: Coffee
3745:
3744:
3733:
3732:
3684:Coffee leaf rust
3557:Dandelion coffee
3423:Coffee companies
3262:Gassosa al caffè
3030:Espresso machine
2664:
2657:
2650:
2641:
2640:
2636:
2616:
2615:
2579:
2573:
2572:
2560:
2554:
2553:
2542:
2536:
2535:
2499:
2493:
2492:
2482:
2473:(6): 1853–1859.
2458:
2452:
2451:
2441:
2431:
2414:(6): 1413–1415.
2399:
2393:
2392:
2390:
2388:
2382:
2376:. Archived from
2367:
2359:
2353:
2352:
2341:
2335:
2334:
2324:
2300:
2291:
2290:
2283:
2277:
2276:
2245:Mol Cell Biochem
2239:
2233:
2232:
2200:
2194:
2193:
2170:J. Am. Chem. Soc
2166:Kaplan, David L.
2161:
2155:
2154:
2126:
2120:
2119:
2110:(9): 1789–1796.
2099:
2093:
2092:
2082:
2046:
2040:
2039:
2037:
2035:
2026:. Archived from
2016:
2010:
2009:
1999:
1975:
1966:
1965:
1960:. Archived from
1954:
1948:
1947:
1945:
1943:
1929:
1923:
1922:
1894:
1888:
1887:
1855:
1849:
1848:
1838:
1828:
1800:
1794:
1793:
1765:
1759:
1758:
1748:
1725:
1719:
1718:
1711:
1705:
1704:
1676:
1670:
1669:
1659:
1631:
1625:
1624:
1599:(4): 1018–1023.
1589:Salvinia molesta
1584:
1578:
1577:
1575:
1551:
1545:
1544:
1515:
1509:
1508:
1476:
1467:
1466:
1456:
1428:
1238:enzymic browning
1234:dactylifric acid
1200:sodium periodate
1090:
1084:
1027:chlorogenic acid
980:black chokeberry
921:Salvinia molesta
860:
839:organic compound
813:
807:
804:
803:
773:Chlorogenic acid
752:
745:
738:
723:
703:
699:
695:
691:
687:
683:
679:
675:
671:
667:
663:
659:
655:
651:
647:
643:
639:
635:
631:
617:
613:
609:
605:
601:
573:
568:
474:Chemical formula
404:
403:
388:
386:
370:
350:
339:
325:
305:
276:
268:
257:
246:
226:
206:
186:
154:
129:
122:
44:
35:
26:
19:
15:
7542:
7541:
7537:
7536:
7535:
7533:
7532:
7531:
7497:
7496:
7495:
7490:
7476:
7313:
7267:
7165:
7146:
7134:
7121:
7111:
7107:Propentofylline
7057:Benzodiazepines
7043:
7033:
6980:
6961:
6945:
6564:
6515:Sodium ferulate
6483:Radix puerariae
6458:Phenolphthalein
6158:
6151:
6136:
6128:
6029:Propentofylline
5969:Isovaleric acid
5653:
5645:
5605:
5597:
5592:Purine receptor
5589:
5559:
5554:
5529:
5525:
5473:
5455:
5452:
5442:
5424:
5420:
5410:
5392:
5388:
5378:
5365:
5361:
5351:
5303:
5299:
5289:
5261:
5251:
5223:
5213:
5183:
5084:
5065:
5049:
5045:
5030:
5027:
5017:
4998:
4990:
4982:
4967:
4964:
4954:
4825:
4817:
4809:
4794:
4791:
4777:
4763:
4739:
4731:
4691:
4688:
4678:
4594:
4576:
4568:
4548:
4545:
4531:
4512:
4504:
4493:
4463:
4458:
4433:
4432:Conjugates with
4423:
4407:
4383:
4351:Diferulic acids
4328:
4319:Isoverbascoside
4300:Plantainoside A
4210:glycoside (CPG)
4209:
4203:
4198:Rosmarinic acid
4187:Methyl caffeate
4169:
4163:
4118:
4081:
4062:
4056:
4005:
3996:
3994:
3986:glycoside-likes
3970:
3949:
3940:Isoferulic acid
3915:
3894:
3854:
3823:
3817:
3794:
3788:
3758:
3753:
3727:
3718:
3657:
3631:
3586:Serving vessels
3581:
3513:
3432:
3406:
3312:Latte macchiato
3182:Caffè macchiato
3098:
2937:
2896:
2781:
2772:
2753:Coffee roasting
2714:
2673:
2668:
2629:"Chemical Land"
2627:
2624:
2619:
2590:(12): 432–435.
2580:
2576:
2561:
2557:
2552:. 2 March 2010.
2544:
2543:
2539:
2500:
2496:
2459:
2455:
2400:
2396:
2386:
2384:
2380:
2365:
2361:
2360:
2356:
2343:
2342:
2338:
2301:
2294:
2285:
2284:
2280:
2240:
2236:
2201:
2197:
2162:
2158:
2127:
2123:
2100:
2096:
2047:
2043:
2033:
2031:
2030:on 3 March 2016
2018:
2017:
2013:
1976:
1969:
1956:
1955:
1951:
1941:
1939:
1931:
1930:
1926:
1895:
1891:
1856:
1852:
1801:
1797:
1766:
1762:
1727:
1726:
1722:
1713:
1712:
1708:
1677:
1673:
1632:
1628:
1585:
1581:
1552:
1548:
1516:
1512:
1477:
1470:
1429:
1425:
1421:
1395:
1357:
1306:carcinogenicity
1304:Studies of the
1252:
1223:
1215:
1211:
1136:
1103:
1096:
1039:sinapyl alcohol
1007:
964:sunflower seeds
956:Ceylon cinnamon
936:
909:Hordeum vulgare
895:
858:
854:
850:
846:
842:
832:
825:
820:
819:
818: ?)
809:
805:
801:
797:
783:
779:
775:
769:
757:
756:
755:
754:
747:
740:
733:
729:
721:
626:
596:
582:
561:
532:
490:
486:
482:
476:
462:
459:
454:
453:
442:
439:
438:
435:
429:
428:
425:
419:
418:
407:
389:
382:
373:
353:
340:
328:
308:
295:
286:
249:
229:
209:
189:
166:
157:
144:
133:
112:
98:
97:
82:
80:
78:
72:
66:
61:
59:
12:
11:
5:
7540:
7530:
7529:
7524:
7519:
7514:
7509:
7492:
7491:
7481:
7478:
7477:
7475:
7474:
7460:
7459:
7454:
7449:
7444:
7439:
7434:
7429:
7424:
7419:
7414:
7409:
7404:
7399:
7394:
7389:
7384:
7379:
7374:
7369:
7364:
7359:
7354:
7349:
7344:
7339:
7334:
7325:
7323:
7319:
7318:
7315:
7314:
7312:
7311:
7306:
7301:
7296:
7291:
7286:
7281:
7275:
7273:
7269:
7268:
7266:
7265:
7260:
7255:
7250:
7245:
7238:
7233:
7228:
7223:
7218:
7213:
7208:
7203:
7196:
7194:Cinnamaldehyde
7191:
7186:
7181:
7176:
7170:
7168:
7154:
7140:
7139:
7136:
7135:
7133:
7132:
7126:
7124:
7113:
7112:
7110:
7109:
7104:
7099:
7097:Pentoxifylline
7094:
7089:
7084:
7079:
7074:
7069:
7064:
7059:
7054:
7048:
7046:
7035:
7034:
7032:
7031:
7026:
7021:
7016:
7011:
7006:
7001:
6996:
6991:
6985:
6983:
6969:
6955:
6954:
6951:
6950:
6947:
6946:
6944:
6943:
6938:
6933:
6928:
6923:
6918:
6913:
6908:
6903:
6898:
6893:
6888:
6883:
6878:
6873:
6868:
6863:
6858:
6853:
6848:
6843:
6838:
6833:
6828:
6823:
6818:
6813:
6808:
6803:
6798:
6793:
6788:
6783:
6774:
6773:
6768:
6763:
6758:
6753:
6748:
6743:
6738:
6733:
6728:
6723:
6718:
6713:
6708:
6703:
6698:
6693:
6688:
6683:
6678:
6673:
6668:
6663:
6658:
6653:
6648:
6643:
6638:
6633:
6628:
6623:
6618:
6613:
6608:
6603:
6598:
6593:
6588:
6583:
6574:
6572:
6566:
6565:
6563:
6562:
6557:
6552:
6540:
6535:
6530:
6512:
6507:
6502:
6497:
6492:
6487:
6475:
6470:
6465:
6460:
6455:
6450:
6445:
6440:
6435:
6430:
6425:
6420:
6415:
6410:
6405:
6400:
6395:
6390:
6385:
6380:
6375:
6370:
6365:
6360:
6348:
6343:
6338:
6333:
6328:
6323:
6318:
6313:
6308:
6303:
6298:
6293:
6288:
6283:
6274:
6273:
6268:
6263:
6258:
6253:
6248:
6243:
6238:
6233:
6228:
6223:
6218:
6213:
6208:
6203:
6198:
6193:
6188:
6183:
6178:
6173:
6164:
6162:
6142:
6130:
6129:
6127:
6126:
6121:
6116:
6111:
6106:
6101:
6096:
6091:
6086:
6081:
6076:
6071:
6066:
6061:
6056:
6051:
6046:
6041:
6036:
6031:
6026:
6021:
6019:Pentoxifylline
6016:
6011:
6006:
6001:
5996:
5991:
5986:
5981:
5976:
5974:Istradefylline
5971:
5966:
5961:
5956:
5951:
5946:
5941:
5936:
5931:
5926:
5921:
5916:
5911:
5906:
5901:
5896:
5891:
5886:
5881:
5876:
5871:
5866:
5861:
5856:
5851:
5846:
5841:
5832:
5831:
5826:
5821:
5816:
5811:
5806:
5801:
5796:
5791:
5786:
5778:
5773:
5768:
5763:
5758:
5753:
5748:
5743:
5738:
5733:
5728:
5723:
5718:
5713:
5708:
5703:
5698:
5689:
5684:
5679:
5674:
5668:2-(1-Hexynyl)-
5661:
5659:
5647:
5646:
5644:
5643:
5638:
5636:8-Aminoadenine
5629:
5627:
5613:
5599:
5598:
5588:
5587:
5580:
5573:
5565:
5556:
5555:
5553:
5552:
5545:
5538:
5534:
5531:
5530:
5528:
5527:
5523:
5519:
5514:
5509:
5507:Diacylglycerol
5504:
5499:
5494:
5485:
5483:
5479:
5478:
5475:
5474:
5472:
5471:
5466:
5460:
5458:
5450:
5444:
5443:
5441:
5440:
5435:
5429:
5427:
5418:
5412:
5411:
5409:
5408:
5403:
5397:
5395:
5386:
5380:
5379:
5377:
5376:
5370:
5368:
5359:
5353:
5352:
5350:
5349:
5344:
5339:
5334:
5329:
5324:
5319:
5314:
5308:
5306:
5297:
5291:
5290:
5288:
5287:
5282:
5277:
5272:
5266:
5264:
5253:
5252:
5250:
5249:
5244:
5239:
5234:
5228:
5226:
5215:
5214:
5212:
5211:
5206:
5201:
5196:
5191:
5174:
5173:
5168:
5163:
5158:
5153:
5148:
5140:
5135:
5130:
5125:
5120:
5115:
5110:
5105:
5100:
5095:
5089:
5087:
5073:
5059:
5058:
5055:
5054:
5051:
5050:
5048:
5047:
5043:
5035:
5033:
5025:
5019:
5018:
5016:
5015:
5010:
5001:
5000:
4996:
4992:
4988:
4984:
4980:
4972:
4970:
4962:
4956:
4955:
4953:
4952:
4947:
4942:
4937:
4932:
4927:
4922:
4917:
4912:
4907:
4902:
4897:
4892:
4887:
4882:
4877:
4872:
4867:
4862:
4857:
4852:
4847:
4842:
4837:
4828:
4827:
4823:
4819:
4815:
4811:
4807:
4799:
4797:
4789:
4780:
4769:
4768:
4765:
4764:
4762:
4761:
4756:
4751:
4742:
4741:
4737:
4733:
4729:
4728:20-Hydroxy-LTB
4725:
4720:
4715:
4710:
4705:
4696:
4694:
4686:
4680:
4679:
4677:
4676:
4671:
4666:
4661:
4656:
4651:
4646:
4641:
4636:
4631:
4626:
4621:
4616:
4611:
4606:
4601:
4596:
4592:
4591:20-Carboxy-LTB
4584:
4583:
4578:
4574:
4570:
4566:
4565:20-Hydroxy-LTB
4562:
4553:
4551:
4543:
4534:
4520:
4506:
4505:
4492:
4491:
4484:
4477:
4469:
4460:
4459:
4457:
4456:
4451:
4446:
4440:
4438:
4429:
4428:
4425:
4424:
4422:
4421:
4415:
4413:
4409:
4408:
4406:
4405:
4391:
4389:
4385:
4384:
4382:
4381:
4375:8,5′-DiFA (BF)
4371:8,5′-DiFA (DC)
4353:(DiFA) :
4347:
4345:
4338:
4334:
4333:
4330:
4329:
4327:
4326:
4312:
4307:
4305:Plantamajoside
4302:
4297:
4292:
4287:
4282:
4249:
4236:
4219:
4213:
4211:
4205:
4204:
4202:
4201:
4195:
4189:
4184:
4182:Ethyl caffeate
4179:
4173:
4171:
4165:
4164:
4162:
4161:
4155:
4150:
4145:
4139:
4133:
4131:
4124:
4123:
4120:
4119:
4117:
4116:
4107:
4099:
4093:
4091:
4087:
4086:
4083:
4082:
4080:
4079:
4068:
4066:
4058:
4057:
4055:
4054:
4049:
4044:
4038:
4028:
4018:
4011:
4009:
3998:
3997:with cyclitols
3987:
3980:
3976:
3975:
3972:
3971:
3969:
3968:
3963:
3957:
3955:
3951:
3950:
3948:
3947:
3945:Sinapinic acid
3942:
3937:
3932:
3926:
3924:
3917:
3916:
3914:
3913:
3908:
3902:
3900:
3896:
3895:
3893:
3892:
3887:
3882:
3877:
3871:
3864:
3862:
3856:
3855:
3853:
3852:
3850:-Coumaric acid
3844:
3842:-Coumaric acid
3836:
3834:-Coumaric acid
3827:
3825:
3819:
3818:
3816:
3815:
3809:
3807:
3800:
3796:
3795:
3787:
3786:
3779:
3772:
3764:
3755:
3754:
3752:
3751:
3738:
3723:
3720:
3719:
3717:
3716:
3711:
3706:
3701:
3696:
3691:
3686:
3681:
3679:Coffee service
3676:
3671:
3665:
3663:
3659:
3658:
3656:
3655:
3650:
3645:
3639:
3637:
3633:
3632:
3630:
3629:
3624:
3619:
3618:
3617:
3607:
3602:
3601:
3600:
3589:
3587:
3583:
3582:
3580:
3579:
3574:
3569:
3564:
3559:
3554:
3549:
3544:
3539:
3534:
3529:
3523:
3521:
3515:
3514:
3512:
3511:
3506:
3501:
3496:
3491:
3486:
3481:
3479:Coffee cupping
3476:
3474:Coffee culture
3471:
3466:
3461:
3456:
3451:
3449:Bikini barista
3446:
3440:
3438:
3434:
3433:
3431:
3430:
3425:
3420:
3414:
3412:
3408:
3407:
3405:
3404:
3399:
3397:Wiener Melange
3394:
3389:
3384:
3382:Turkish coffee
3379:
3374:
3369:
3364:
3359:
3354:
3349:
3344:
3339:
3334:
3329:
3324:
3322:Liqueur coffee
3319:
3314:
3309:
3307:Kurdish coffee
3304:
3299:
3294:
3289:
3284:
3279:
3274:
3269:
3264:
3259:
3254:
3249:
3244:
3239:
3234:
3229:
3224:
3222:Dalgona coffee
3219:
3214:
3209:
3204:
3202:Coffee cabinet
3199:
3194:
3189:
3184:
3179:
3174:
3172:Caffè corretto
3169:
3164:
3159:
3157:Café con leche
3154:
3149:
3144:
3139:
3134:
3129:
3124:
3119:
3114:
3108:
3106:
3100:
3099:
3097:
3096:
3091:
3086:
3084:Turkish coffee
3081:
3076:
3071:
3066:
3061:
3060:
3059:
3052:Instant coffee
3049:
3044:
3043:
3042:
3032:
3027:
3026:
3025:
3020:
3015:
3005:
3000:
2999:
2998:
2988:
2983:
2978:
2973:
2968:
2963:
2958:
2953:
2947:
2945:
2939:
2938:
2936:
2935:
2930:
2925:
2920:
2915:
2910:
2904:
2902:
2898:
2897:
2895:
2894:
2893:
2892:
2880:
2873:
2872:
2871:
2859:
2852:
2851:
2850:
2845:
2840:
2835:
2830:
2825:
2820:
2815:
2810:
2805:
2800:
2787:
2785:
2774:
2773:
2771:
2770:
2765:
2763:Decaffeination
2760:
2755:
2750:
2745:
2744:
2743:
2738:
2733:
2731:Organic coffee
2722:
2720:
2716:
2715:
2713:
2712:
2707:
2702:
2697:
2692:
2687:
2681:
2679:
2675:
2674:
2667:
2666:
2659:
2652:
2644:
2638:
2637:
2623:
2622:External links
2620:
2618:
2617:
2574:
2555:
2537:
2494:
2453:
2394:
2354:
2345:"Caffeic Acid"
2336:
2315:(1): 207–212.
2309:Carcinogenesis
2292:
2278:
2251:(1–2): 11–19.
2234:
2215:(2): 124–128.
2195:
2156:
2137:(2): 499–505.
2131:Phytochemistry
2121:
2094:
2065:(5): 609–616.
2041:
2011:
1967:
1964:on 2000-12-05.
1949:
1924:
1889:
1850:
1795:
1760:
1729:"Caffeic acid"
1720:
1706:
1687:(13): 3660–7.
1671:
1626:
1593:Phytochemistry
1579:
1546:
1510:
1468:
1422:
1420:
1417:
1416:
1415:
1410:
1405:
1394:
1391:
1369:instant coffee
1356:
1353:
1310:carcinogenesis
1251:
1248:
1222:
1219:
1213:
1209:
1191:into reactive
1135:
1134:Biodegradation
1132:
1102:
1099:
1094:
1087:-phenylalanine
1083:3,4-dihydroxy-
1076:
1075:
1006:
1003:
935:
932:
894:
891:
856:
852:
848:
844:
830:
827:
826:
821:
799:
798:
794:standard state
791:
788:
787:
770:
767:
764:
763:
759:
758:
748:
741:
734:
719:
718:
717:
716:
714:
705:
704:
666:P305+P351+P338
627:
622:
619:
618:
597:
592:
589:
588:
583:
578:
575:
574:
562:
557:
554:
553:
543:
542:
538:
537:
534:
530:
523:
522:
519:
513:
512:
509:
503:
502:
499:
493:
492:
488:
484:
480:
477:
472:
469:
468:
464:
463:
461:
460:
457:
449:
448:
447:
444:
443:
441:
440:
436:
433:
432:
430:
426:
423:
422:
414:
413:
412:
409:
408:
406:
405:
392:
390:
378:
375:
374:
372:
371:
363:
361:
355:
354:
352:
351:
343:
341:
333:
330:
329:
327:
326:
318:
316:
310:
309:
307:
306:
298:
296:
291:
288:
287:
285:
284:
280:
278:
270:
269:
259:
251:
250:
248:
247:
239:
237:
231:
230:
228:
227:
219:
217:
211:
210:
208:
207:
199:
197:
191:
190:
188:
187:
179:
177:
171:
170:
167:
162:
159:
158:
156:
155:
147:
145:
138:
135:
134:
132:
131:
123:
115:
113:
108:
105:
104:
100:
99:
91:
90:
84:
83:
67:3,4-Dihydroxy-
57:
51:
50:
46:
45:
37:
36:
28:
27:
9:
6:
4:
3:
2:
7539:
7528:
7525:
7523:
7520:
7518:
7515:
7513:
7510:
7508:
7505:
7504:
7502:
7489:
7488:
7485:
7479:
7472:
7468:
7465:
7462:
7461:
7458:
7455:
7453:
7450:
7448:
7445:
7443:
7440:
7438:
7435:
7433:
7430:
7428:
7425:
7423:
7420:
7418:
7415:
7413:
7410:
7408:
7405:
7403:
7400:
7398:
7395:
7393:
7390:
7388:
7385:
7383:
7380:
7378:
7375:
7373:
7370:
7368:
7365:
7363:
7360:
7358:
7355:
7353:
7350:
7348:
7345:
7343:
7340:
7338:
7335:
7333:
7330:
7327:
7326:
7324:
7320:
7310:
7307:
7305:
7302:
7300:
7297:
7295:
7292:
7290:
7287:
7285:
7282:
7280:
7277:
7276:
7274:
7270:
7264:
7261:
7259:
7256:
7254:
7251:
7249:
7246:
7244:
7243:
7239:
7237:
7234:
7232:
7229:
7227:
7224:
7222:
7219:
7217:
7214:
7212:
7209:
7207:
7204:
7202:
7201:
7197:
7195:
7192:
7190:
7187:
7185:
7184:Benzbromarone
7182:
7180:
7177:
7175:
7172:
7171:
7169:
7164:
7158:
7155:
7151:
7145:
7141:
7131:
7128:
7127:
7125:
7120:
7114:
7108:
7105:
7103:
7100:
7098:
7095:
7093:
7090:
7088:
7085:
7083:
7080:
7078:
7075:
7073:
7070:
7068:
7065:
7063:
7060:
7058:
7055:
7053:
7050:
7049:
7047:
7042:
7036:
7030:
7027:
7025:
7022:
7020:
7017:
7015:
7012:
7010:
7007:
7005:
7002:
7000:
6997:
6995:
6992:
6990:
6987:
6986:
6984:
6979:
6973:
6970:
6966:
6960:
6956:
6942:
6939:
6937:
6934:
6932:
6929:
6927:
6924:
6922:
6919:
6917:
6914:
6912:
6909:
6907:
6904:
6902:
6899:
6897:
6894:
6892:
6889:
6887:
6884:
6882:
6879:
6877:
6874:
6872:
6869:
6867:
6864:
6862:
6859:
6857:
6854:
6852:
6849:
6847:
6844:
6842:
6839:
6837:
6834:
6832:
6829:
6827:
6824:
6822:
6819:
6817:
6816:AR-C 118925XX
6814:
6812:
6809:
6807:
6804:
6802:
6799:
6797:
6794:
6792:
6789:
6787:
6784:
6782:
6779:
6776:
6775:
6772:
6769:
6767:
6764:
6762:
6759:
6757:
6754:
6752:
6749:
6747:
6746:UDP-galactose
6744:
6742:
6739:
6737:
6734:
6732:
6729:
6727:
6724:
6722:
6719:
6717:
6714:
6712:
6709:
6707:
6704:
6702:
6699:
6697:
6694:
6692:
6689:
6687:
6684:
6682:
6679:
6677:
6674:
6672:
6669:
6667:
6664:
6662:
6659:
6657:
6654:
6652:
6649:
6647:
6644:
6642:
6639:
6637:
6634:
6632:
6629:
6627:
6624:
6622:
6619:
6617:
6614:
6612:
6609:
6607:
6604:
6602:
6599:
6597:
6594:
6592:
6589:
6587:
6584:
6582:
6579:
6576:
6575:
6573:
6571:
6567:
6561:
6558:
6556:
6553:
6550:
6549:
6544:
6541:
6539:
6536:
6534:
6531:
6528:
6527:
6522:
6521:
6516:
6513:
6511:
6508:
6506:
6503:
6501:
6498:
6496:
6493:
6491:
6488:
6485:
6484:
6479:
6476:
6474:
6471:
6469:
6466:
6464:
6461:
6459:
6456:
6454:
6451:
6449:
6446:
6444:
6441:
6439:
6436:
6434:
6431:
6429:
6426:
6424:
6421:
6419:
6416:
6414:
6411:
6409:
6406:
6404:
6401:
6399:
6396:
6394:
6391:
6389:
6386:
6384:
6381:
6379:
6376:
6374:
6371:
6369:
6366:
6364:
6361:
6358:
6357:
6352:
6349:
6347:
6344:
6342:
6341:Chelerythrine
6339:
6337:
6336:Calmidazolium
6334:
6332:
6329:
6327:
6324:
6322:
6319:
6317:
6314:
6312:
6309:
6307:
6304:
6302:
6299:
6297:
6294:
6292:
6289:
6287:
6284:
6282:
6279:
6276:
6275:
6272:
6269:
6267:
6264:
6262:
6259:
6257:
6254:
6252:
6249:
6247:
6244:
6242:
6239:
6237:
6234:
6232:
6229:
6227:
6224:
6222:
6221:Cibacron blue
6219:
6217:
6214:
6212:
6209:
6207:
6204:
6202:
6199:
6197:
6194:
6192:
6189:
6187:
6184:
6182:
6179:
6177:
6174:
6172:
6169:
6166:
6165:
6163:
6157:
6150:
6146:
6143:
6140:
6135:
6131:
6125:
6122:
6120:
6117:
6115:
6112:
6110:
6107:
6105:
6102:
6100:
6099:Theodrenaline
6097:
6095:
6092:
6090:
6087:
6085:
6082:
6080:
6077:
6075:
6072:
6070:
6067:
6065:
6062:
6060:
6057:
6055:
6052:
6050:
6047:
6045:
6042:
6040:
6037:
6035:
6034:Proxyphylline
6032:
6030:
6027:
6025:
6022:
6020:
6017:
6015:
6012:
6010:
6007:
6005:
6002:
6000:
5997:
5995:
5992:
5990:
5987:
5985:
5982:
5980:
5977:
5975:
5972:
5970:
5967:
5965:
5962:
5960:
5957:
5955:
5952:
5950:
5947:
5945:
5942:
5940:
5937:
5935:
5932:
5930:
5927:
5925:
5922:
5920:
5917:
5915:
5912:
5910:
5907:
5905:
5902:
5900:
5897:
5895:
5892:
5890:
5887:
5885:
5882:
5880:
5877:
5875:
5872:
5870:
5867:
5865:
5864:Aminophylline
5862:
5860:
5857:
5855:
5852:
5850:
5847:
5845:
5842:
5840:
5837:
5834:
5833:
5830:
5827:
5825:
5822:
5820:
5817:
5815:
5812:
5810:
5807:
5805:
5802:
5800:
5797:
5795:
5792:
5790:
5787:
5785:
5783:
5779:
5777:
5774:
5772:
5769:
5767:
5764:
5762:
5759:
5757:
5754:
5752:
5749:
5747:
5744:
5742:
5739:
5737:
5734:
5732:
5729:
5727:
5724:
5722:
5719:
5717:
5714:
5712:
5709:
5707:
5704:
5702:
5699:
5697:
5695:
5690:
5688:
5685:
5683:
5680:
5678:
5675:
5673:
5671:
5666:
5663:
5662:
5660:
5657:
5652:
5648:
5642:
5639:
5637:
5634:
5631:
5630:
5628:
5625:
5621:
5617:
5614:
5610:
5604:
5600:
5596:
5593:
5586:
5581:
5579:
5574:
5572:
5567:
5566:
5563:
5551:
5550:
5546:
5544:
5543:
5539:
5536:
5535:
5532:
5526:
5522:Leukotriene A
5520:
5518:
5515:
5513:
5510:
5508:
5505:
5503:
5500:
5498:
5495:
5493:
5492:Linoleic acid
5490:
5487:
5486:
5484:
5480:
5470:
5467:
5465:
5462:
5461:
5459:
5454:
5445:
5439:
5436:
5434:
5431:
5430:
5428:
5423:
5413:
5407:
5404:
5402:
5399:
5398:
5396:
5391:
5381:
5375:
5372:
5371:
5369:
5364:
5354:
5348:
5345:
5343:
5340:
5338:
5335:
5333:
5330:
5328:
5325:
5323:
5320:
5318:
5315:
5313:
5310:
5309:
5307:
5302:
5292:
5286:
5283:
5281:
5278:
5276:
5273:
5271:
5268:
5267:
5265:
5260:
5254:
5248:
5245:
5243:
5240:
5238:
5235:
5233:
5230:
5229:
5227:
5222:
5216:
5210:
5207:
5205:
5202:
5200:
5197:
5195:
5192:
5190:
5187:
5182:
5176:
5175:
5172:
5169:
5167:
5164:
5162:
5159:
5157:
5154:
5152:
5149:
5147:
5145:
5141:
5139:
5136:
5134:
5131:
5129:
5126:
5124:
5121:
5119:
5116:
5114:
5111:
5109:
5106:
5104:
5101:
5099:
5096:
5094:
5091:
5090:
5088:
5083:
5077:
5074:
5070:
5064:
5060:
5046:
5042:Leukotriene E
5040:
5037:
5036:
5034:
5029:
5020:
5014:
5011:
5009:
5006:
5003:
5002:
4999:
4995:Leukotriene E
4993:
4991:
4987:Leukotriene D
4985:
4983:
4979:Leukotriene C
4977:
4974:
4973:
4971:
4966:
4957:
4951:
4948:
4946:
4943:
4941:
4938:
4936:
4933:
4931:
4928:
4926:
4923:
4921:
4918:
4916:
4913:
4911:
4908:
4906:
4903:
4901:
4898:
4896:
4893:
4891:
4888:
4886:
4883:
4881:
4878:
4876:
4873:
4871:
4868:
4866:
4863:
4861:
4858:
4856:
4853:
4851:
4848:
4846:
4843:
4841:
4838:
4836:
4833:
4830:
4829:
4826:
4822:Leukotriene E
4820:
4818:
4814:Leukotriene D
4812:
4810:
4806:Leukotriene C
4804:
4801:
4800:
4798:
4793:
4784:
4781:
4776:
4770:
4760:
4757:
4755:
4752:
4750:
4747:
4744:
4743:
4740:
4736:Leukotriene B
4734:
4732:
4726:
4724:
4721:
4719:
4716:
4714:
4711:
4709:
4706:
4704:
4701:
4698:
4697:
4695:
4690:
4681:
4675:
4672:
4670:
4667:
4665:
4662:
4660:
4657:
4655:
4652:
4650:
4647:
4645:
4642:
4640:
4637:
4635:
4632:
4630:
4627:
4625:
4622:
4620:
4617:
4615:
4612:
4610:
4607:
4605:
4602:
4600:
4597:
4595:
4589:
4586:
4585:
4582:
4579:
4577:
4573:Leukotriene B
4571:
4569:
4563:
4561:
4558:
4555:
4554:
4552:
4547:
4538:
4535:
4530:
4524:
4521:
4517:
4511:
4507:
4503:
4500:
4497:
4490:
4485:
4483:
4478:
4476:
4471:
4470:
4467:
4455:
4454:Coumaroyl-CoA
4452:
4450:
4449:Cinnamoyl-CoA
4447:
4445:
4442:
4441:
4439:
4436:
4430:
4420:
4417:
4416:
4414:
4410:
4404:
4402:
4396:
4393:
4392:
4390:
4386:
4380:
4376:
4372:
4368:
4364:
4362:
4356:
4352:
4349:
4348:
4346:
4342:
4339:
4335:
4324:
4320:
4316:
4313:
4311:
4308:
4306:
4303:
4301:
4298:
4296:
4293:
4291:
4288:
4286:
4283:
4281:
4277:
4273:
4269:
4265:
4261:
4257:
4253:
4252:Cistanoside A
4250:
4248:
4244:
4240:
4239:Chiritoside A
4237:
4235:
4231:
4227:
4223:
4220:
4218:
4215:
4214:
4212:
4206:
4199:
4196:
4193:
4190:
4188:
4185:
4183:
4180:
4178:
4175:
4174:
4172:
4166:
4159:
4156:
4154:
4153:Fertaric acid
4151:
4149:
4148:Coutaric acid
4146:
4143:
4142:Chicoric acid
4140:
4138:
4137:Caftaric acid
4135:
4134:
4132:
4129:
4128:Tartaric acid
4125:
4115:
4108:
4106:
4104:
4100:
4098:
4095:
4094:
4092:
4088:
4077:
4073:
4070:
4069:
4067:
4065:
4064:shikimic acid
4059:
4053:
4050:
4048:
4045:
4042:
4039:
4036:
4032:
4029:
4026:
4022:
4019:
4016:
4013:
4012:
4010:
4008:
4002:
3999:
3991:
3988:
3984:
3981:
3977:
3967:
3964:
3962:
3959:
3958:
3956:
3952:
3946:
3943:
3941:
3938:
3936:
3933:
3931:
3928:
3927:
3925:
3922:
3918:
3912:
3909:
3907:
3904:
3903:
3901:
3897:
3891:
3888:
3886:
3883:
3881:
3878:
3875:
3874:Umbellic acid
3872:
3869:
3866:
3865:
3863:
3861:
3857:
3851:
3849:
3845:
3843:
3841:
3837:
3835:
3833:
3829:
3828:
3826:
3820:
3814:
3813:Cinnamic acid
3811:
3810:
3808:
3804:
3801:
3797:
3793:
3785:
3780:
3778:
3773:
3771:
3766:
3765:
3762:
3750:
3749:
3739:
3737:
3736:
3731:
3725:
3724:
3721:
3715:
3712:
3710:
3707:
3705:
3702:
3700:
3699:Canned coffee
3697:
3695:
3692:
3690:
3687:
3685:
3682:
3680:
3677:
3675:
3672:
3670:
3667:
3666:
3664:
3660:
3654:
3651:
3649:
3646:
3644:
3641:
3640:
3638:
3634:
3628:
3625:
3623:
3620:
3616:
3613:
3612:
3611:
3608:
3606:
3603:
3599:
3596:
3595:
3594:
3591:
3590:
3588:
3584:
3578:
3575:
3573:
3570:
3568:
3565:
3563:
3560:
3558:
3555:
3553:
3550:
3548:
3547:Cereal coffee
3545:
3543:
3540:
3538:
3535:
3533:
3530:
3528:
3527:Barley coffee
3525:
3524:
3522:
3520:
3516:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3484:Coffee palace
3482:
3480:
3477:
3475:
3472:
3470:
3467:
3465:
3462:
3460:
3457:
3455:
3454:Caffè sospeso
3452:
3450:
3447:
3445:
3442:
3441:
3439:
3435:
3429:
3426:
3424:
3421:
3419:
3416:
3415:
3413:
3409:
3403:
3400:
3398:
3395:
3393:
3392:White Russian
3390:
3388:
3385:
3383:
3380:
3378:
3375:
3373:
3370:
3368:
3365:
3363:
3360:
3358:
3355:
3353:
3350:
3348:
3345:
3343:
3340:
3338:
3335:
3333:
3330:
3328:
3325:
3323:
3320:
3318:
3315:
3313:
3310:
3308:
3305:
3303:
3300:
3298:
3295:
3293:
3290:
3288:
3285:
3283:
3280:
3278:
3275:
3273:
3270:
3268:
3265:
3263:
3260:
3258:
3255:
3253:
3250:
3248:
3245:
3243:
3242:Frappé coffee
3240:
3238:
3235:
3233:
3230:
3228:
3225:
3223:
3220:
3218:
3215:
3213:
3210:
3208:
3205:
3203:
3200:
3198:
3195:
3193:
3190:
3188:
3185:
3183:
3180:
3178:
3175:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3145:
3143:
3142:Cà phê sữa đá
3140:
3138:
3137:Black Russian
3135:
3133:
3130:
3128:
3125:
3123:
3122:Beaten coffee
3120:
3118:
3115:
3113:
3110:
3109:
3107:
3105:
3104:Coffee drinks
3101:
3095:
3092:
3090:
3087:
3085:
3082:
3080:
3077:
3075:
3072:
3070:
3067:
3065:
3062:
3058:
3055:
3054:
3053:
3050:
3048:
3045:
3041:
3038:
3037:
3036:
3033:
3031:
3028:
3024:
3021:
3019:
3016:
3014:
3011:
3010:
3009:
3006:
3004:
3001:
2997:
2994:
2993:
2992:
2989:
2987:
2984:
2982:
2979:
2977:
2974:
2972:
2969:
2967:
2966:Brewed coffee
2964:
2962:
2959:
2957:
2956:Arabic coffee
2954:
2952:
2949:
2948:
2946:
2944:
2940:
2934:
2931:
2929:
2926:
2924:
2921:
2919:
2916:
2914:
2911:
2909:
2906:
2905:
2903:
2899:
2891:
2888:
2887:
2886:
2885:
2881:
2879:
2878:
2874:
2870:
2867:
2866:
2865:
2864:
2860:
2858:
2857:
2853:
2849:
2846:
2844:
2841:
2839:
2836:
2834:
2831:
2829:
2826:
2824:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2804:
2803:Blue Mountain
2801:
2799:
2796:
2795:
2794:
2793:
2789:
2788:
2786:
2784:
2779:
2775:
2769:
2768:Home roasting
2766:
2764:
2761:
2759:
2756:
2754:
2751:
2749:
2746:
2742:
2739:
2737:
2734:
2732:
2729:
2728:
2727:
2724:
2723:
2721:
2717:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2688:
2686:
2683:
2682:
2680:
2676:
2672:
2665:
2660:
2658:
2653:
2651:
2646:
2645:
2642:
2634:
2630:
2626:
2625:
2613:
2609:
2605:
2601:
2597:
2593:
2589:
2585:
2578:
2570:
2566:
2559:
2551:
2550:Caffenol blog
2547:
2541:
2533:
2529:
2525:
2521:
2517:
2513:
2509:
2505:
2498:
2490:
2486:
2481:
2476:
2472:
2468:
2464:
2457:
2449:
2445:
2440:
2435:
2430:
2425:
2421:
2417:
2413:
2409:
2405:
2398:
2379:
2375:
2371:
2364:
2358:
2350:
2346:
2340:
2332:
2328:
2323:
2318:
2314:
2310:
2306:
2299:
2297:
2288:
2282:
2274:
2270:
2266:
2262:
2258:
2254:
2250:
2246:
2238:
2230:
2226:
2222:
2218:
2214:
2210:
2206:
2199:
2191:
2187:
2183:
2179:
2175:
2171:
2167:
2160:
2152:
2148:
2144:
2140:
2136:
2132:
2125:
2117:
2113:
2109:
2105:
2098:
2090:
2086:
2081:
2076:
2072:
2068:
2064:
2060:
2056:
2054:
2045:
2029:
2025:
2021:
2020:"EC 4.3.1.11"
2015:
2007:
2003:
1998:
1993:
1989:
1985:
1981:
1974:
1972:
1963:
1959:
1953:
1938:
1934:
1928:
1920:
1916:
1912:
1908:
1904:
1900:
1893:
1885:
1881:
1877:
1873:
1869:
1865:
1861:
1854:
1846:
1842:
1837:
1832:
1827:
1822:
1818:
1814:
1810:
1808:
1799:
1791:
1787:
1783:
1779:
1775:
1771:
1764:
1756:
1752:
1747:
1742:
1738:
1734:
1730:
1724:
1716:
1710:
1702:
1698:
1694:
1690:
1686:
1682:
1675:
1667:
1663:
1658:
1653:
1649:
1645:
1641:
1639:
1630:
1622:
1618:
1614:
1610:
1606:
1602:
1598:
1594:
1590:
1583:
1574:
1569:
1565:
1561:
1557:
1550:
1542:
1538:
1534:
1530:
1526:
1522:
1514:
1506:
1502:
1498:
1494:
1490:
1486:
1482:
1475:
1473:
1464:
1460:
1455:
1450:
1446:
1442:
1438:
1436:
1427:
1423:
1414:
1411:
1409:
1406:
1403:
1402:Umbellic acid
1400:
1399:
1398:
1390:
1388:
1385:
1380:
1378:
1374:
1370:
1366:
1362:
1352:
1350:
1345:
1341:
1337:
1333:
1329:
1325:
1322:
1318:
1315:
1311:
1307:
1302:
1300:
1296:
1295:
1290:
1286:
1282:
1281:
1276:
1273:
1268:
1266:
1263:
1259:
1258:
1247:
1245:
1244:
1239:
1235:
1231:
1229:
1218:
1216:
1205:
1201:
1197:
1195:
1190:
1188:
1183:
1179:
1175:
1171:
1167:
1163:
1159:
1154:
1152:
1150:
1146:
1140:
1131:
1129:
1127:
1122:
1117:
1115:
1111:
1109:
1098:
1088:
1080:
1071:
1066:
1062:
1061:
1060:
1058:
1053:
1051:
1049:
1044:
1040:
1036:
1032:
1028:
1024:
1023:shikimic acid
1020:
1016:
1012:
1011:hydroxylation
1002:
1000:
996:
992:
989:
985:
981:
977:
973:
969:
965:
961:
957:
953:
949:
945:
941:
931:
929:
928:
923:
922:
917:
915:
911:and the herb
910:
906:
902:
901:
890:
888:
884:
880:
876:
872:
868:
864:
840:
836:
824:
817:
812:
795:
789:
786:
782:
781:Coumaric acid
778:
777:Cichoric acid
774:
771:
766:
765:
760:
753:
746:
739:
715:
712:
711:
707:
706:
628:
625:
621:
620:
598:
595:
591:
590:
587:
584:
581:
577:
576:
572:
567:
563:
560:
556:
555:
551:
549:
544:
539:
535:
528:
525:
524:
520:
518:
517:Melting point
515:
514:
510:
508:
505:
504:
500:
498:
495:
494:
478:
475:
471:
470:
465:
456:
455:
452:
445:
431:
421:
420:
417:
410:
402:
398:
394:
393:
391:
381:
377:
376:
369:
365:
364:
362:
360:
357:
356:
349:
345:
344:
342:
336:
332:
331:
324:
320:
319:
317:
315:
312:
311:
304:
300:
299:
297:
294:
290:
289:
282:
281:
279:
277:
272:
271:
267:
263:
260:
258:
256:ECHA InfoCard
253:
252:
245:
241:
240:
238:
236:
233:
232:
225:
221:
220:
218:
216:
213:
212:
205:
201:
200:
198:
196:
193:
192:
185:
181:
180:
178:
176:
173:
172:
168:
165:
161:
160:
153:
149:
148:
146:
142:
137:
136:
128:
124:
121:
117:
116:
114:
111:
107:
106:
101:
95:
89:
85:
76:
70:
64:
56:
52:
47:
43:
38:
34:
29:
25:
20:
17:Caffeic acid
7483:
7482:
7467:Chrysophanol
7463:
7407:Hypoxanthine
7328:
7308:
7304:Pralatrexate
7289:Methotrexate
7284:Azathioprine
7263:Topiroxostat
7240:
7211:Myo-inositol
7198:
7189:Caffeic acid
7188:
7102:Progesterone
7072:Dipyridamole
7052:Barbiturates
7029:Progesterone
6811:AR-C 69931MX
6806:AR-C 67085MX
6778:Antagonists:
6777:
6631:AR-C 67085MX
6577:
6546:
6524:
6518:
6481:
6448:Oxidized-ATP
6393:JNJ-47965567
6354:
6278:Antagonists:
6277:
6251:L-β,γ-Me-ATP
6231:D-β,γ-Me-ATP
6167:
6104:Theophylline
6014:Paraxanthine
5959:Fenethylline
5949:Enprofylline
5914:Ciforadenant
5836:Antagonists:
5835:
5799:Piclidenoson
5781:
5693:
5677:2-Cl-IB-MECA
5669:
5664:
5632:
5547:
5540:
5488:
5332:JNJ-26993135
5327:Fosinoprilat
5177:
5143:
5113:Caffeic acid
5112:
5038:
5005:Antagonists:
5004:
4975:
4832:Antagonists:
4831:
4802:
4746:Antagonists:
4745:
4699:
4588:Antagonists:
4587:
4556:
4444:Caffeoyl-CoA
4400:
4360:
4315:Verbascoside
4310:Tubuloside B
4295:Pauoifloside
4285:Conandroside
4217:Echinacoside
4168:Other esters
4102:
4075:
4034:
4024:
3995:caffeic acid
3930:Ferulic acid
3920:
3868:Caffeic acid
3867:
3847:
3839:
3831:
3740:
3726:
3636:Competitions
3622:Tasse à café
3459:Coffee break
3428:Coffeehouses
3418:Bakery cafés
3387:White coffee
3377:Tenom coffee
3282:Irish coffee
3162:Café de olla
3147:Café au lait
3089:Vacuum maker
3057:Coffee syrup
3047:French press
2913:Caffeic acid
2912:
2882:
2875:
2861:
2856:Charrieriana
2854:
2790:
2632:
2587:
2583:
2577:
2568:
2558:
2549:
2540:
2507:
2503:
2497:
2470:
2466:
2456:
2411:
2407:
2397:
2385:. Retrieved
2378:the original
2369:
2357:
2348:
2339:
2312:
2308:
2281:
2248:
2244:
2237:
2212:
2208:
2204:
2198:
2173:
2169:
2159:
2134:
2130:
2124:
2107:
2103:
2097:
2062:
2058:
2052:
2044:
2032:. Retrieved
2028:the original
2023:
2014:
1990:(1): 66–71.
1987:
1983:
1962:the original
1952:
1940:. Retrieved
1936:
1927:
1902:
1898:
1892:
1867:
1863:
1859:
1853:
1816:
1812:
1806:
1798:
1776:(2): 502–9.
1773:
1769:
1763:
1736:
1732:
1723:
1709:
1684:
1680:
1674:
1647:
1643:
1637:
1629:
1596:
1592:
1588:
1582:
1563:
1559:
1549:
1524:
1520:
1513:
1488:
1484:
1444:
1440:
1434:
1426:
1396:
1381:
1358:
1303:
1292:
1278:
1274:
1269:
1265:fibrosarcoma
1255:
1253:
1250:Pharmacology
1241:
1227:
1224:
1193:
1186:
1158:autoxidation
1155:
1148:
1144:
1137:
1125:
1120:
1118:
1114:ferulic acid
1107:
1104:
1077:
1070:ferulic acid
1054:
1047:
1031:ferulic acid
1008:
1005:Biosynthesis
991:densitometry
937:
925:
919:
912:
908:
898:
896:
875:biosynthesis
835:Caffeic acid
834:
833:
709:
585:
547:
103:Identifiers
93:
74:
68:
62:
7329:Precursors:
7309:Many others
7279:Aminopterin
7236:Phytic acid
7179:Amflutizole
7174:Allopurinol
7130:Decynium-22
7087:Hexobendine
6959:Transporter
6936:Ticlopidine
6841:Clopidogrel
6751:UDP-glucose
6490:Purotoxin 1
6321:AZ-11645373
6316:AZ-10606120
6114:Tracazolate
6094:Theobromine
6079:SCH-442,416
6074:Rolofylline
6024:Preladenant
5894:Cartazolate
5874:Bamifylline
5824:Tecadenoson
5819:Sonedenoson
5814:Selodenoson
5809:SDZ WAG 994
5804:Regadenoson
5789:Namodenoson
5741:Capadenoson
5736:Binodenoson
5731:BAY 60–6583
5489:Precursors:
5312:Acebilustat
5186:inhibitors:
5156:Minocycline
4945:Zafirlukast
4890:Montelukast
4496:Leukotriene
4110:1-Sinapoyl-
4007:quinic acid
3689:Coffee wars
3519:Substitutes
3489:Coffeehouse
3302:Kopi tubruk
3267:Iced coffee
3247:Frappuccino
3217:Café Cubano
3207:Coffee milk
3187:Caffè mocha
3177:Caffè crema
3035:French drip
3003:Drip coffee
2986:Coffeemaker
2943:Preparation
2923:Coffee bean
2828:Maracaturra
2510:: 218–223.
1491:: 519–546.
1340:metabolites
1272:antioxidant
1168:compounds (
1162:Glutathione
1019:quinic acid
968:apple sauce
785:Quinic acid
580:Signal word
511:1.478 g/cm
467:Properties
262:100.005.784
184:CHEBI:16433
55:IUPAC names
7501:Categories
7299:Pemetrexed
7258:Tisopurine
7231:Oxipurinol
7226:Niraxostat
7216:Kaempferol
7206:Febuxostat
7150:inhibitors
7062:Cilostazol
7024:Phloridzin
6931:Ticagrelor
6801:AR-C 66096
6661:Diquafosol
6606:α,β-Me-ATP
6591:2-Thio-UTP
6500:Ro 0437626
6453:Phenol Red
6368:Gefapixant
6363:Evans blue
6246:Ivermectin
6176:α,β-Me-ATP
6139:nucleotide
6124:ZM-241,385
6109:Tozadenant
5984:MRE3008F20
5944:Dyphylline
5929:Dimethazan
5859:Acefylline
5829:UK-432,097
5761:Evodenoson
5756:CP-532,903
5716:Apadenoson
5595:modulators
5464:Cilastatin
5401:Azelastine
5166:Timegadine
5138:Hyperforin
5069:inhibitors
4935:Tomelukast
4930:Tipelukast
4915:SKF-104353
4910:Ritolukast
4905:Pranlukast
4900:Pobilukast
4880:Masilukast
4865:ICI-198615
4855:Cinalukast
4664:Ticolubant
4634:Moxilubant
4609:CGS-25019C
4502:modulators
4435:coenzyme A
4290:Myconoside
4090:Glycosides
3966:Plicatin B
3961:Plicatin A
3674:Coffee bag
3593:Coffee cup
3532:Barley tea
3357:Raf coffee
3337:Marocchino
3327:Long black
3297:Kopi luwak
3237:Flat white
3227:Egg coffee
3192:Cappuccino
3167:Café Touba
3079:Percolator
2981:Chorreador
2901:Components
2833:Maragogipe
2719:Production
2690:Fair trade
2059:Biochem. J
1819:: 658596.
1809:St.-Hil.)"
1419:References
1389:analyses.
1377:pyrogallol
1367:made from
1355:Other uses
1317:papillomas
1221:Glycosides
1189:-diphenols
1178:thiocresol
984:yerba mate
960:star anise
916:asperoides
559:Pictograms
497:Molar mass
368:U2S3A33KVM
293:IUPHAR/BPS
215:ChemSpider
139:3D model (
110:CAS Number
71:-cinnamate
7522:Catechols
7484:See also:
7387:Guanosine
7337:Adenosine
7253:Quercetin
7221:Myricetin
7077:Estradiol
7004:Estradiol
6994:Adenosine
6906:Prasugrel
6846:Elinogrel
6836:Cangrelor
6781:2-Me-SAMP
6721:PAPET-ATP
6681:INS-37217
6656:Denufosol
6611:Adenosine
6601:5-OMe-UDP
6586:2-Me-SATP
6581:2-Me-SADP
6578:Agonists:
6473:PSB-12062
6408:Magnesium
6373:GW-791343
6261:PAPET-ATP
6181:Adenosine
6171:2-Me-SATP
6168:Agonists:
6089:Theacrine
6084:SCH-58261
6069:Reversine
5954:Etazolate
5904:CGS-15943
5879:Cafedrine
5751:CGS-21680
5701:Adenosine
5682:2'-MeCCPA
5665:Agonists:
5656:adenosine
5633:Agonists:
5342:SC-57461A
5317:Captopril
5285:PD-146176
5242:Baicalein
5133:Fenleuton
5098:Baicalein
5039:Agonists:
4976:Agonists:
4940:Verlukast
4875:LY-170680
4870:Iralukast
4860:FPL-55712
4803:Agonists:
4759:ZK-158252
4754:LY-255283
4749:CP-195543
4700:Agonists:
4674:ZK-158252
4654:SB-209247
4629:LY-293111
4619:CP-195543
4614:CP-105696
4599:Amelubant
4581:LY-255283
4557:Agonists:
4499:signaling
4412:Tetramers
4061:esters of
4004:esters of
3993:Esters of
3806:Precursor
3799:Aglycones
3790:Types of
3610:Demitasse
3537:Barleycup
3504:Latte art
3499:Kopi tiam
3469:CoffeeCon
3437:Lifestyle
3402:Yuenyeung
3367:Ristretto
3197:Carajillo
3117:Americano
3023:ristretto
2991:Cold brew
2951:AeroPress
2808:Bonifieur
2783:varieties
2685:Economics
1299:fungicide
1289:aflatoxin
1277:and also
1246:fruits).
1196:-quinones
1151:-muconate
1106:Caffeate
1046:caffeate
1017:ester of
1015:coumaroyl
952:spearmint
694:P403+P233
686:P337+P313
682:P332+P313
670:P308+P313
662:P304+P340
658:P302+P352
550:labelling
283:206-361-2
275:EC Number
204:ChEMBL145
65:-Caffeate
7362:Cytidine
7357:Cytosine
7248:Propolis
7014:KGO-2173
7009:KGO-2142
6999:dMeThPmR
6965:blockers
6921:Regrelor
6911:PSB-0739
6881:MRS-2578
6876:MRS-2500
6871:MRS-2395
6866:MRS-2279
6861:MRS-2211
6856:MRS-2179
6731:PSB-1114
6726:PSB-0474
6711:MRS-4062
6706:MRS-2957
6701:MRS-2768
6696:MRS-2693
6691:MRS-2690
6686:MRS-2365
6596:5-Br-UDP
6538:TC-P 262
6478:Puerarin
6413:MRS-2159
6388:isoPPADS
6306:A-839977
6301:A-804598
6296:A-740003
6291:A-438079
6286:A-317491
6256:MRS-2219
6119:VUF-5574
6064:PSB-1115
6009:MRS-3777
6004:MRS-1754
5999:MRS-1706
5994:MRS-1334
5989:MRS-1220
5979:KF-26777
5924:CVT-6883
5899:CGH-2466
5884:Caffeine
5776:LUF-5845
5771:LUF-5835
5766:GR 79236
5721:ATL-146e
5603:Receptor
5537:See also
5433:Acivicin
5280:Luteolin
5199:BAYx1005
5171:Zileuton
5128:Curcumin
5123:CJ-13610
5013:BAYu9916
5008:BAYu9773
4925:Sulukast
4895:ONO-1078
4850:BAYx7195
4845:BAYu9916
4840:BAYu9773
4835:Ablukast
4723:15-HpETE
4713:12-HpETE
4659:SC-53228
4649:RP-69698
4644:RG-14893
4639:ONO-4057
4624:Etalocib
4510:Receptor
4399:5-5′,8′-
4397: :
4114:-glucose
4041:Cynarine
3567:Maya nut
3342:Mazagran
3232:Espresso
3112:Affogato
3069:Moka pot
3064:Knockbox
3008:Espresso
2918:Caffeine
2908:Cafestol
2877:Racemosa
2863:Liberica
2524:27597761
2489:12771329
2273:28014579
2265:21116690
2190:16104752
2006:11208940
1919:17177530
1884:21510640
1845:23841023
1790:12517117
1701:12059140
1666:18827365
1621:18177906
1541:21761864
1505:14503002
1463:10948238
1437:A. Cunn"
1373:catechol
1361:caffenol
1349:cytokine
1344:thiamine
1336:bacteria
1275:in vitro
1257:in vitro
1182:ascorbic
1170:cysteine
972:apricots
914:Dipsacus
887:caffeine
867:phenolic
710:NFPA 704
541:Hazards
235:DrugBank
169:1954563
127:331-39-5
120:501-16-6
7471:rhubarb
7464:Others:
7442:Uridine
7412:Inosine
7382:Guanine
7332:Adenine
7082:Ethanol
7067:Dilazep
7019:MeThPmR
6926:Suramin
6831:C1330-7
6676:INS-365
6555:TNP-ATP
6533:Suramin
6331:Calcium
6059:PSB-788
6054:PSB-603
5869:ATL-444
5641:Adenine
5624:adenine
5609:ligands
5337:SA-6541
5108:BW-B70C
4950:ZD-3523
4920:SR-2640
4718:15-HETE
4703:12-HETE
4669:U-75302
4560:12-HETE
4516:ligands
4388:Trimers
3552:Chicory
3444:Barista
3362:Red eye
3347:Moretta
3212:Cortado
3132:Bicerin
2933:Kahweol
2884:Robusta
2838:Molokai
2813:Bourbon
2798:Benguet
2792:Arabica
2778:Species
2695:History
2612:2520223
2592:Bibcode
2532:5361129
2448:4504351
2416:Bibcode
2387:4 April
2370:iarc.fr
2351:. 1993.
2331:9472713
2229:5836492
2139:Bibcode
2089:4980678
2080:1187763
2034:4 April
1984:J. Nutr
1942:4 April
1836:3690244
1755:8411618
1746:7681336
1601:Bibcode
1566:: 1–6.
1393:Isomers
1314:stomach
1280:in vivo
1262:HT-1080
883:biomass
871:acrylic
855:CH=CHCO
816:what is
814: (
586:Warning
507:Density
491:
335:PubChem
244:DB01880
7437:Uracil
7432:Ribose
7322:Others
7272:Others
7144:Enzyme
6891:NF-340
6886:NF-157
6786:A3P5PS
6716:NF-546
6438:NF-449
6433:NF-279
6428:NF-157
6423:NF-110
6418:NF-023
6351:Emodin
6346:Copper
6311:AF-353
6281:5-BDBD
6241:HT-AMP
6049:PSB-36
6044:PSB-11
6039:PSB-10
5482:Others
5406:MK-886
5322:DG-051
5270:2-TEDC
5258:15-LOX
5232:2-TEDC
5220:12-LOX
5209:MK-886
5204:MK-591
5194:AM-679
5189:AM-103
5103:BW-A4C
5093:2-TEDC
5063:Enzyme
4885:MK-571
4708:12-HHT
4344:Dimers
4194:(CAPE)
4130:esters
3979:Esters
3954:others
3746:
3598:sleeve
3572:Postum
3352:Oliang
3257:Garoto
3013:doppio
2971:Chemex
2961:Jebena
2869:Barako
2848:Sagada
2818:Geisha
2678:Topics
2671:Coffee
2610:
2530:
2522:
2487:
2446:
2439:426714
2436:
2329:
2271:
2263:
2227:
2188:
2087:
2077:
2004:
1917:
1882:
1843:
1833:
1788:
1753:
1743:
1699:
1664:
1619:
1539:
1503:
1461:
1324:tumors
1043:enzyme
1037:, and
995:barley
976:prunes
940:coffee
907:grain
905:barley
879:lignin
837:is an
811:verify
808:
527:UV-vis
451:SMILES
348:689043
323:C01481
224:600426
195:ChEMBL
49:Names
7092:NBMPR
6901:PPADS
6826:BzATP
6791:AMPαS
6771:UTPγS
6741:UDPβS
6641:ATPγS
6621:ADPβS
6505:Ro 51
6468:PPNDS
6463:PPADS
6403:KN-62
6398:KN-04
6216:BzATP
6211:ATPγS
5939:DPCPX
5081:5-LOX
5024:CysLT
4961:CysLT
4788:CysLT
4774:CysLT
4437:(CoA)
3662:Misc.
3615:spoon
3605:Cezve
3577:Qishr
3332:Lungo
3317:Latte
3287:Karsk
3252:Galão
3018:lungo
2996:nitro
2976:Cezve
2528:S2CID
2381:(PDF)
2366:(PDF)
2269:S2CID
1384:MALDI
1330:as a
1321:colon
1180:) or
1166:thiol
944:thyme
416:InChI
175:ChEBI
141:JSmol
69:trans
63:trans
7118:PMAT
7040:ENTs
6977:CNTs
6916:RB-2
6851:Ip5I
6796:Ap4A
6761:Up3U
6651:dATP
6626:Ap3A
6560:Zinc
6510:RO-3
6495:RB-2
6383:Ip5I
6271:Zinc
6201:Ap5A
6196:Ap4A
5964:IBMX
5934:DMPX
5746:CCPA
5180:FLAP
3627:Zarf
3562:Inka
3542:Caro
3292:Kopi
3127:Bica
2890:Sulu
2843:S795
2823:Kona
2780:and
2608:PMID
2520:PMID
2485:PMID
2444:PMID
2389:2018
2327:PMID
2261:PMID
2225:PMID
2186:PMID
2085:PMID
2036:2018
2002:PMID
1944:2018
1915:PMID
1880:PMID
1841:PMID
1817:2013
1786:PMID
1751:PMID
1697:PMID
1662:PMID
1617:PMID
1564:2014
1537:PMID
1501:PMID
1459:PMID
1164:and
997:and
974:and
958:and
950:and
948:sage
903:the
869:and
843:(HO)
702:P501
698:P405
690:P362
678:P321
674:P312
654:P281
650:P280
646:P271
642:P264
638:P261
634:P202
630:P201
616:H361
612:H351
608:H335
604:H319
600:H315
359:UNII
314:KEGG
303:5155
7457:UTP
7452:UDP
7447:UMP
7427:ITP
7422:IDP
7417:IMP
7402:GTP
7397:GDP
7392:GMP
7377:CTP
7372:CDP
7367:CMP
7352:ATP
7347:ADP
7342:AMP
6941:UDP
6896:PIT
6821:ATP
6766:UTP
6736:UDP
6671:ITP
6666:IDP
6646:CTP
6636:ATP
6616:ADP
6570:P2Y
6378:HMA
6326:BBG
6266:UTP
6236:GTP
6226:CTP
6206:ATP
6191:AMP
6186:ADP
6155:ATP
6149:P2X
5919:CPX
5726:ATP
5711:AMP
5706:ADP
5692:5'-
5449:LTD
5417:LTC
5385:LTC
5358:LTB
5296:LTA
5275:CDC
5247:CDC
5118:CDC
4685:BLT
4542:BLT
4528:BLT
4369:,
4074:(3-
4033:(5-
4023:(4-
2600:doi
2512:doi
2508:632
2475:doi
2471:133
2434:PMC
2424:doi
2317:doi
2253:doi
2249:349
2217:doi
2178:doi
2174:127
2147:doi
2112:doi
2075:PMC
2067:doi
2063:112
1992:doi
1988:131
1907:doi
1872:doi
1831:PMC
1821:doi
1778:doi
1741:PMC
1689:doi
1652:doi
1609:doi
1591:".
1568:doi
1529:doi
1493:doi
1449:doi
1375:or
1176:or
1160:.
1149:cis
1145:cis
1013:of
999:rye
877:of
548:GHS
531:max
385:EPA
338:CID
7503::
7162:XO
6523:,
6134:P2
5651:P1
5620:P0
4377:,
4373:,
4365:,
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