1592:(BFR), 1 kg of (cassia) cinnamon powder contains about 2.1 to 4.4 g of coumarin. Powdered cassia cinnamon weighs 0.56 g/cm, so a kilogram of cassia cinnamon powder equals 362.29 teaspoons. One teaspoon of cassia cinnamon powder therefore contains 5.8 to 12.1 mg of coumarin, which may be above the tolerable daily intake value for smaller individuals. However, the BFR only cautions against high daily intake of foods containing coumarin. Its report specifically states that Ceylon cinnamon (
409:
268:
705:
700:
828:
63:
45:
831:
949:
833:
54:
832:
1569:, a compound of lower toxicity, and no adverse affect has been directly measured in humans. The German Federal Institute for Risk Assessment has established a tolerable daily intake (TDI) of 0.1 mg coumarin per kg body weight, but also advises that higher intake for a short time is not dangerous. The
1668:
between anticoagulant exposure and minor neurological dysfunction. Overall, a 1.9 (90%) increase in minor neurological dysfunction was observed for children exposed to these anticoagulants, which are collectively referred to as "coumarins." In conclusion, researchers stated, "The results suggest that
1714:
are limited to a maximum of 10 mg/L coumarin by law. Cinnamon flavor is generally cassia bark steam-distilled to concentrate the cinnamaldehyde, for example, to about 93%. Clear cinnamon-flavored alcoholic beverages generally test negative for coumarin, but if whole cassia bark is used to make
1609:
An investigation from the Danish
Veterinary and Food Administration in 2013 shows that bakery goods characterized as fine bakery ware exceeds the European limit (15 mg/kg) in almost 50% of the cases. The paper also mentions tea as an additional important contributor to the overall coumarin
1516:. These chemicals are sometimes also incorrectly referred to as "coumadins" rather than 4-hydroxycoumarins. Some of the 4-hydroxycoumarin anticoagulant class of chemicals are designed to have high potency and long residence times in the body, and these are used specifically as
910:
1601:
The
European Regulation (EC) No 1334/2008 describes the following maximum limits for coumarin: 50 mg/kg in traditional and/or seasonal bakery ware containing a reference to cinnamon in the labeling, 20 mg/kg in breakfast cereals including
1258:
Coumarin is found naturally in many plants. Freshly ground plant parts contain higher amount of desired and undesired phytochemicals than powder. In addition, whole plant parts are harder to counterfeit; for example, one study showed that authentic
2227:
Leal, L. K. A. M.; Ferreira, A. A. G.; Bezerra, G. A.; Matos, F. J. A.; Viana, G. S. B. (May 2000). "Antinociceptive, anti-inflammatory and bronchodilator activities of
Brazilian medicinal plants containing coumarin: a comparative study".
1532:
substitutes, despite having been banned as a food additive in numerous countries since the mid-20th century. It is still used as a legal flavorant in soaps, rubber products, and the tobacco industry, particularly for sweet
1163:
Also in 1820, Nicholas Jean
Baptiste Gaston Guibourt (1790–1867) of France independently isolated coumarin, but he realized that it was not benzoic acid. In a subsequent essay he presented to the pharmacy section of the
713:
680:
3186:
Wang, YH; Avula, B.; Zhao, J.; Smillie, TJ; Nanayakkara, NPD; Khan, IA (2010). "Characterization and
Distribution of Coumarin, Cinnamaldehyde and Related Compounds in Cinnamomum spp. by UPLC-UV/MS Combined with PCA".
1443:
Coumarin has appetite-suppressing properties, which may discourage animals from eating plants that contain it. Though the compound has a pleasant sweet odor, it has a bitter taste, and animals tend to avoid it.
1706:
had banned its addition to human food in 1954. Under his later testimony, he would repeatedly classify coumarin as a "lung-specific carcinogen." In
Germany, coumarin is banned as an additive in tobacco.
1653:
Coumarin is subject to restrictions on its use in perfumery, as some people may become sensitized to it, however the evidence that coumarin can cause an allergic reaction in humans is disputed.
2716:
1606:, 15 mg/kg in fine bakery ware, with the exception of traditional and/or seasonal bakery ware containing a reference to cinnamon in the labeling, and 5 mg/kg in desserts.
1263:
bark contained 0.012 to 0.143 mg/g coumarin, but samples purchased at markets contained up to 3.462 mg/g, possibly because those were mixed with other cinnamon varieties.
1561:) of 293 mg/kg in the rat, a low toxicity compared to related compounds. Coumarin is hepatotoxic in rats, but less so in mice. Rodents metabolize it mostly to 3,4-coumarin
962:
1175:
In 1835, the French pharmacist A. Guillemette proved that Vogel and
Guibourt had isolated the same substance. Coumarin was first synthesized in 1868 by the English chemist
2769:
2325:
Ieri, Francesca; Pinelli, Patrizia; Romani, Annalisa (2012). "Simultaneous determination of anthocyanins, coumarins and phenolic acids in fruits, kernels and liqueur of
834:
2855:
1613:
Coumarin was banned as a food additive in the United States in 1954, largely because of the hepatotoxicity results in rodents. Coumarin is currently listed by the
842:
1664:
during pregnancy. A group of 306 children were tested at ages 7–15 years to determine subtle neurological effects from anticoagulant exposure. Results showed a
1570:
1698:" was being used as an additive. He held that from a chemist’s point of view, coumarin is an "immediate precursor" to the rodenticide (and prescription drug)
458:
1565:, a toxic, unstable compound that on further differential metabolism may cause liver cancer in rats and lung tumors in mice. Humans metabolize it mainly to
1919:... plus récemment, dans un essai de nomenclature chimique, lu à la section de Pharmacie de l'Académie royale de Médecine, il l'a désignée sous le nom de
1500:
Coumarin is used in the pharmaceutical industry as a precursor reagent in the synthesis of a number of synthetic anticoagulant pharmaceuticals similar to
2191:
2384:"Phenolic constituents of licorice. IV. Correlation of phenolic constituents and licorice specimens from various sources, and inhibitory effects of..."
3231:
1927:... read to the pharmacy section of the Royal Academy of Medicine, he designated it by the name "coumarine," derived from the name of the vegetable
856:
3049:"Cropwatch Claims Victory Regarding "26 Allergens" Legislation : Modified from article originally written for Aromaconnection, Feb 2008"
2073:
Jacobowitz, Joseph R.; Weng, Jing-Ke (2020-04-29). "Exploring
Uncharted Territories of Plant Specialized Metabolism in the Postgenomic Era".
1589:
2993:
2933:
2526:"A novel complex locus UGT1 encodes human bilirubin, phenol, and other UDP-glucuronosyltransferase isozymes with identical carboxyl termini"
2727:
1669:
coumarins have an influence on the development of the brain which can lead to mild neurologic dysfunctions in children of school age."
3367:
2589:
2292:
2204:
849:
3023:
3726:
423:
2825:
1165:
2871:
Ballin, Nicolai Z.; Sørensen, Ann T. (April 2014). "Coumarin content in cinnamon containing food products on the Danish market".
2272:
1083:
779:
1665:
1617:(FDA) of the United States among "Substances Generally Prohibited From Direct Addition or Use as Human Food," according to 21
2075:
2132:"Quantification of coumarin and related phenolics in cinnamon samples from south India using UHPLC-ESI-QqQLIT-MS/MS method"
19:
This article is about the natural compound. For the anticoagulants and rodenticides called "coumarins" or "coumadins", see
3224:
775:
969:
2852:
1703:
1614:
749:
366:
799:
704:
3476:
3048:
2963:
2428:
1629:
1618:
771:
387:
3136:
2826:"High daily intakes of cinnamon: Health risk cannot be ruled out. BfR Health Assessment No. 044/2006, 18 August 2006"
699:
2437:
2084:
1360:
3716:
3706:
741:
275:
3217:
1520:("rat poison"). Death occurs after a period of several days to two weeks, usually from internal hemorrhaging.
2681:
Lake, B.G (1999). "Coumarin
Metabolism, Toxicity and Carcinogenicity: Relevance for Human Risk Assessment".
640:
2171:
Cassia
Cinnamon as a Source of Coumarin in Cinnamon-Flavored Food and Food Supplements in the United States
263:
3360:
3076:
Wessling, J. (2001). "Neurological outcome in school-age children after in utero exposure to coumarins".
3721:
1886:
1827:[Preparation of benzoic acid from tonka beans and from the flowers of melilot or sweet clover].
1269:
1211:
727:
692:
616:
153:
75:
1677:
205:
3660:
3258:
2646:
Born, S. L.; et al. (2003). "Comparative metabolism and kinetics of coumarin in mice and rats".
1836:
1509:
1495:
1339:
1247:
1219:
1176:
1109:
89:
24:
2898:
Marles, R. J.; et al. (1986). "Coumarin in vanilla extracts: Its detection and significance".
1944:
1369:
767:
404:
119:
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3001:
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1647:
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759:
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20:
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2457:
2449:
2404:
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2245:
2200:
2104:
2096:
1968:
1906:
1825:"Darstellung von Benzoesäure aus der Tonka-Bohne und aus den Meliloten- oder Steinklee-Blumen"
1566:
1330:
1095:
1025:
904:
664:
225:
1991:
3196:
3085:
2907:
2880:
2690:
2655:
2618:
2607:"Metabolic detoxification determines species differences in coumarin-induced hepatotoxicity"
2537:
2496:
2441:
2394:
2346:
2338:
2304:
2288:
2237:
2143:
2088:
2055:
2003:
1866:[On the existence of benzoic acid in the tonka bean and in the flowers of melilot].
1844:
1594:
1321:
1303:
1207:
987:
571:
481:
2586:
2130:
Ananthakrishnan, R.; Chandra, Preeti; Kumar, Brijesh; Rameshkumar, K. B. (1 January 2018).
2021:
791:
375:
3250:
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3027:
2859:
2593:
2092:
1863:
1625:
1346:
1278:
1260:
1203:
1199:
783:
294:
1864:"De l'existence de l'acide benzoïque dans la fève de tonka et dans les fleurs de mélilot"
1840:
803:
408:
267:
185:
129:
3549:
3493:
3273:
3267:
2445:
1755:. PubChem, National Library of Medicine, US National Institutes of Health. 4 April 2019
1711:
1681:
1641:
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629:
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2542:
2525:
2241:
1479:
3695:
3675:
3650:
3645:
3403:
3298:
2469:
2193:
Leung's Encyclopedia of Common Natural Ingredients Used in Food, Drugs, and Cosmetics
2157:
2116:
1661:
1657:
1469:
1457:
1417:
1235:
1195:
1135:
1098:
592:
588:
560:
550:
256:
2919:
2368:
2300:
807:
3334:
2884:
2342:
1702:. Dr. Wigand later stated that coumarin itself is dangerous, pointing out that the
1656:
Minor neurological dysfunction was found in children exposed to the anticoagulants
1534:
1453:
1413:
1316:; a 2013 study showed different varieties containing different levels of coumarin:
1157:
931:
763:
737:
2484:
2399:
2383:
2148:
2131:
62:
2422:
Berenbaum, May R.; Calla, Bernarda (2021-01-07). "Honey as a Functional Food for
3670:
3605:
3600:
3554:
3528:
2770:"Cassia cinnamon with high coumarin contents to be consumed in moderation - BfR"
1752:
1716:
1581:
1517:
1465:
1400:
1186:
genre of perfume since it was first used in Houbigant's Fougère Royale in 1882.
1153:
1068:
1060:
892:
868:
339:
3629:
3559:
3434:
3393:
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3161:
1695:
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1501:
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1183:
1131:
1105:
596:
582:
509:
216:
3111:
2453:
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2100:
1848:
3655:
3595:
3544:
3508:
3448:
3424:
3293:
3209:
2623:
2606:
1799:
1673:
1622:
1513:
1378:
1296:
1223:
1087:
3200:
3097:
2971:
2702:
2667:
2632:
2510:
2501:
2461:
2360:
2257:
2108:
44:
2565:
2551:
2408:
1992:"On the artificial production of coumarin and formation of its homologues"
3680:
3518:
3513:
3471:
3456:
3419:
3385:
3288:
3263:
2293:
10.1002/(SICI)1099-1573(199705)11:3<211::AID-PTR72>3.0.CO;2-W
2007:
1699:
1585:
1432:
1425:
1405:
1313:
1101:
1048:
927:
855:
848:
841:
814:
604:
236:
31:
2059:
1082:
and a bitter taste. It is found in many plants, where it may serve as a
245:
3579:
3523:
3466:
3398:
3318:
2911:
2717:"Frequently Asked Questions about coumarin in cinnamon and other foods"
2351:
1634:
1580:
European health agencies have warned against consuming high amounts of
1562:
1421:
1079:
1052:
1044:
609:
540:
326:
276:
2271:
Lino, C. S.; Taveira, M. L.; Viana, G. S. B.; Matos, F. J. A. (1997).
3461:
3429:
3345:
3313:
3308:
1951:... la matière cristalline de la fève tonka (matière que j'ai nommée
1621:
189.130, but some natural additives containing coumarin, such as the
1603:
1474:
1391:
1215:
1214:
provides another route to coumarin and its derivatives starting from
1064:
196:
1824:
939:
Except where otherwise noted, data are given for materials in their
733:
53:
1398:
Related compounds are found in some but not all specimens of genus
314:
1895:] (in French). Vol. 2. Paris: L. Colas. pp. 160–161.
1800:"Warfarin, Molecule of the Month for February 2011, by John Maher"
350:
176:
152:
142:
3024:"Standards Restricted - IFRA International Fragrance Association"
2046:
Sethna, S. M.; Shah, N. M. (1945). "The Chemistry of Coumarins".
1431:
Coumarins were found to be uncommon but occasional components of
1075:
530:
305:
3349:
3213:
1412:
Coumarin is found naturally also in many edible plants such as
1685:
1002:
600:
1971:[Research into the crystalline material of melilot].
1949:(6th ed.). Paris: J. B. Baillière et fils. p. 377.
996:
2277:
Jacq. and its main constituents: coumarin and umbelliferone"
2199:. Hoboken, NJ USA: John Wiley & Sons. pp. 240–242.
1588:, because of its coumarin content. According to the German
1573:(OSHA) of the United States does not classify coumarin as a
1156:
in 1820 by A. Vogel of Munich, who initially mistook it for
795:
392:
1632:
172.510. In Europe, popular examples of such beverages are
1911:
Journal de Chimie Médicale, de Pharmacie et de Toxicologie
1005:
826:
1074:
Coumarin is a colorless crystalline solid with a sweet
957:
1139:
1008:
993:
3112:"Jeffrey Wigand : Jeffrey Wigand on 60 Minutes"
1610:
intake, especially for children with a sweet habit.
1482:
activity with many substrates, including coumarins.
3638:
3622:
3588:
3572:
3537:
3501:
3492:
3485:
3447:
3412:
3384:
3327:
3248:
1628:are allowed "in alcoholic beverages only" under 21
999:
990:
1969:"Recherches sur la matière cristalline du mélilot"
432:InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
442:InChI=1/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
2724:The German Federal Institute for Risk Assessment
1719:, then coumarin shows up at significant levels.
338:
1512:. They block the regeneration and recycling of
830:
565:301.71 °C (575.08 °F; 574.86 K)
128:
2273:"Analgesic and antiinflammatory activities of
3361:
3225:
2795:"German Christmas Cookies Pose Health Danger"
2190:Khan, Ikhlas A.; Ehab, Abourashed A. (2010).
1571:Occupational Safety and Health Administration
8:
2485:"The discovery of dicumarol and its sequels"
1472:. In humans, the enzyme encoded by the gene
1435:by Santos-Buelga and Gonzalez-Paramas 2017.
1125:
1071:chemical class and considered as a lactone.
2820:
2818:
2816:
1747:
1745:
1743:
1741:
1739:
1737:
1735:
1733:
1731:
34:, often known by the trade name "Coumadin".
3534:
3498:
3489:
3409:
3368:
3354:
3346:
3232:
3218:
3210:
2853:Engineering Resources – Bulk Density Chart
2745:"Chemical Sampling Information – Coumarin"
2587:Coumarin Material Safety Data Sheet (MSDS)
1182:Coumarin has been an integral part of the
407:
266:
224:
36:
2622:
2541:
2500:
2398:
2350:
2147:
1772:
1770:
1067:with the benzene ring. It belongs to the
374:
2136:International Journal of Food Properties
1194:Coumarin can be prepared by a number of
1039:
1035:
1031:
2524:Ritter, J. K.; et al. (Mar 1992).
1727:
463:
428:
403:
244:
30:Not to be confused with the medication
1946:Histoire Naturelle des Drogues Simples
1337:Indonesian cinnamon or Padang cassia (
1043:. Its molecule can be described as a
873:150 °C (302 °F; 423 K)
257:
2605:Vassallo, J. D.; et al. (2004).
2093:10.1146/annurev-arplant-081519-035634
2022:"Olfactory Groups - Aromatic Fougere"
1590:Federal Institute for Risk Assessment
555:71 °C (160 °F; 344 K)
545:0.935 g/cm (20 °C (68 °F))
435:Key: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
204:
184:
7:
1888:Histoire Abrégée des Drogues Simples
1328:Chinese cinnamon or Chinese cassia (
1222:, which can also be used to produce
634:1.3 hPa (106 °C (223 °F))
1168:, Guibourt named the new substance
445:Key: ZYGHJZDHTFUPRJ-UHFFFAOYAC
329:
313:
2446:10.1146/annurev-ento-040320-074933
1694:in 1995, charging that a "form of
1598:) contains "hardly any" coumarin.
1584:, one of the four main species of
1404:, from which the root and flavour
1319:Ceylon cinnamon or true cinnamon (
1104:, is used to inhibit formation of
1084:chemical defense against predators
14:
2726:. 30 October 2006. Archived from
1152:Coumarin was first isolated from
1086:. Coumarin inhibits synthesis of
1051:atoms replaced by an unsaturated
3589:Meroterpene furanocoumarin ether
3477:Umbelliferone 7-apiosylglucoside
2382:Hatano, T.; et al. (1991).
1893:Abridged History of Simple Drugs
1710:Alcoholic beverages sold in the
1059:, forming a second six-membered
986:
947:
703:
698:
493:
61:
52:
43:
1996:Journal of the Chemical Society
1907:"Societe du Pharmacie de Paris"
943:(at 25 °C , 100 kPa).
2885:10.1016/j.foodcont.2013.10.014
2483:Link, K. P. (1 January 1959).
2343:10.1016/j.foodchem.2012.07.083
2076:Annual Review of Plant Biology
1943:Guibourt, N. J. B. G. (1869).
1885:Guibourt, N. J. B. G. (1820).
1639:white wine with woodruff, and
1537:and certain alcoholic drinks.
499:
487:
1:
3090:10.1016/S0378-3782(01)00140-2
2695:10.1016/S0278-6915(99)00010-1
2660:10.1016/s0278-6915(02)00227-2
2543:10.1016/S0021-9258(19)50724-4
2400:10.1248/yakushi1947.111.6_311
2242:10.1016/S0378-8741(99)00165-8
2149:10.1080/10942912.2018.1437629
1456:of coumarin in plants is via
1389:tree varieties (of the genus
1210:being a popular example. The
535:pleasant, like vanilla beans
3162:"Industry Documents Library"
2683:Food and Chemical Toxicology
2648:Food and Chemical Toxicology
2230:Journal of Ethnopharmacology
1615:Food and Drug Administration
525:colorless to white crystals
2964:"FDA/CFSAN/OPA: EAFUS List"
2429:Annual Review of Entomology
1778:"Coumarins and indandiones"
1528:Coumarin is often found in
1334:): 0.085 to 0.310 mg/g
1325:): 0.005 to 0.090 mg/g
1166:Académie Royale de Médecine
1047:molecule with two adjacent
881:or concentration (LD, LC):
3743:
1666:dose–response relationship
1489:
1361:Carphephorus odoratissimus
1130:, the French word for the
1094:. A related compound, the
577:0.17 g / 100 mL
29:
18:
16:Aromatic chemical compound
3573:Furanocoumarin glycosides
2568:. Drugs.com. 7 March 2019
1353:): 1.06 to 6.97 mg/g
1343:): 2.14 to 9.30 mg/g
1124:Coumarin is derived from
937:
916:
877:
679:
674:
657:
474:
454:
419:
112:
104:
88:
74:
69:
60:
51:
42:
3727:Sweet-smelling chemicals
1967:Guillemette, A. (1835).
1849:10.1002/andp.18200640205
1078:resembling the scent of
750:Precautionary statements
3166:Legacy.library.ucsf.edu
3078:Early Human Development
1923:tiré du nom du végétal
1672:Coumarin's addition to
1545:Coumarin is moderately
1140:
1024:is an aromatic organic
641:Magnetic susceptibility
3201:10.1055/s-0030-1251793
2611:Toxicological Sciences
2502:10.1161/01.CIR.19.1.97
1990:Perkin, W. H. (1868).
1678:Brown & Williamson
1349:or Vietnamese cassia (
1126:
899:293 mg/kg (rat, oral)
837:
23:. For other uses, see
3259:Hydroxycinnamic acids
2624:10.1093/toxsci/kfh162
2281:Phytotherapy Research
1680:caused executive Dr.
1646:vodka flavoured with
1270:Anthoxanthum odoratum
1212:Pechmann condensation
1090:, a key component in
836:
3661:Ethyl biscoumacetate
3141:Tobacco-on-trial.com
2174:J. Agric. Food Chem.
2008:10.1039/js8682100053
1973:Journal de Pharmacie
1868:Journal de Pharmacie
1510:vitamin K antagonist
1496:Coumarin derivatives
1294:Sweet-clover (genus
1248:hydroxycinnamic acid
1220:Kostanecki acylation
1177:William Henry Perkin
1110:deep vein thrombosis
819:(fire diamond)
90:Preferred IUPAC name
25:Coumarin derivatives
2974:on 3 September 2000
2275:Justicia pectoralis
2060:10.1021/cr60113a001
1841:1820AnP....64..161V
1553:of rodents, with a
1439:Biological function
1370:Justicia pectoralis
1138:word for its tree,
1057:−(CH)=(CH)−(C=O)−O−
572:Solubility in water
517: g·mol
166:Beilstein Reference
98:-1-Benzopyran-2-one
39:
3666:4-Hydroxycoumarins
3137:"Tobacco On Trial"
3004:on 5 February 2012
2944:on 5 February 2012
2912:10.1007/BF02859345
2858:2002-10-27 at the
2801:. 25 December 2006
2592:2004-10-21 at the
1929:Coumarouna odorata
1925:coumarouna odorata
1862:Vogel, A. (1820).
1829:Annalen der Physik
1823:Vogel, A. (1820).
1804:www.chm.bris.ac.uk
1555:median lethal dose
1547:toxic to the liver
1530:artificial vanilla
1506:4-hydroxycoumarins
1492:4-Hydroxycoumarins
1288:Hierochloe odorata
1254:Natural occurrence
1114:pulmonary embolism
970:Infobox references
917:Related compounds
838:
107:1-Benzopyran-2-one
37:
21:4-Hydroxycoumarins
3689:
3688:
3618:
3617:
3614:
3613:
3568:
3567:
3443:
3442:
3343:
3342:
3116:Jeffreywigand.com
2968:www.cfsan.fda.gov
2879:(2014): 198–203.
2733:on 19 April 2009.
1780:. Drugs.com. 2016
1567:7-hydroxycoumarin
1096:prescription drug
1026:chemical compound
978:Chemical compound
976:
975:
923:Related compounds
905:Safety data sheet
728:Hazard statements
665:Crystal structure
466:O=C1C=Cc2ccccc2O1
388:CompTox Dashboard
154:Interactive image
3734:
3717:Laser gain media
3707:Fluorescent dyes
3535:
3499:
3490:
3410:
3370:
3363:
3356:
3347:
3251:phenylpropanoids
3242:phenylpropanoids
3234:
3227:
3220:
3211:
3205:
3204:
3183:
3177:
3176:
3174:
3172:
3158:
3152:
3151:
3149:
3147:
3133:
3127:
3126:
3124:
3122:
3108:
3102:
3101:
3073:
3067:
3066:
3064:
3062:
3053:
3045:
3039:
3038:
3036:
3035:
3026:. Archived from
3020:
3014:
3013:
3011:
3009:
3000:. Archived from
2994:"Food and Drugs"
2990:
2984:
2983:
2981:
2979:
2970:. Archived from
2960:
2954:
2953:
2951:
2949:
2940:. Archived from
2934:"Food and Drugs"
2930:
2924:
2923:
2895:
2889:
2888:
2868:
2862:
2850:
2844:
2843:
2841:
2839:
2830:
2822:
2811:
2810:
2808:
2806:
2791:
2785:
2784:
2782:
2780:
2766:
2760:
2759:
2757:
2755:
2741:
2735:
2734:
2732:
2721:
2713:
2707:
2706:
2678:
2672:
2671:
2643:
2637:
2636:
2626:
2602:
2596:
2584:
2578:
2577:
2575:
2573:
2562:
2556:
2555:
2545:
2536:(5): 3257–3261.
2521:
2515:
2514:
2504:
2480:
2474:
2473:
2419:
2413:
2412:
2402:
2379:
2373:
2372:
2354:
2337:(4): 2157–2162.
2322:
2316:
2315:
2313:
2312:
2303:. Archived from
2268:
2262:
2261:
2224:
2218:
2217:
2215:
2213:
2198:
2187:
2181:
2168:
2162:
2161:
2151:
2127:
2121:
2120:
2070:
2064:
2063:
2048:Chemical Reviews
2043:
2037:
2036:
2034:
2032:
2018:
2012:
2011:
1987:
1981:
1980:
1964:
1958:
1957:
1940:
1934:
1933:
1903:
1897:
1896:
1882:
1876:
1875:
1859:
1853:
1852:
1820:
1814:
1813:
1811:
1810:
1796:
1790:
1789:
1787:
1785:
1774:
1765:
1764:
1762:
1760:
1749:
1595:Cinnamomum verum
1322:Cinnamomum verum
1308:Dipteryx odorata
1276:Sweet woodruff (
1208:acetic anhydride
1143:
1129:
1063:that shares two
1058:
1042:
1015:
1014:
1011:
1010:
1007:
1004:
1001:
998:
995:
992:
960:
954:
951:
950:
858:
851:
844:
829:
809:
805:
801:
797:
793:
789:
785:
781:
777:
773:
769:
765:
761:
757:
743:
739:
735:
707:
702:
653:
651:
587:very soluble in
516:
501:
495:
489:
482:Chemical formula
412:
411:
396:
394:
378:
342:
331:
317:
295:Gmelin Reference
278:
270:
259:
248:
228:
208:
188:
156:
132:
65:
56:
47:
40:
3742:
3741:
3737:
3736:
3735:
3733:
3732:
3731:
3692:
3691:
3690:
3685:
3634:
3610:
3584:
3564:
3533:
3494:Furanocoumarins
3481:
3439:
3408:
3380:
3374:
3344:
3339:
3323:
3274:Cinnamaldehydes
3268:Furanochromones
3244:
3238:
3208:
3185:
3184:
3180:
3170:
3168:
3160:
3159:
3155:
3145:
3143:
3135:
3134:
3130:
3120:
3118:
3110:
3109:
3105:
3075:
3074:
3070:
3060:
3058:
3056:Leffingwell.com
3051:
3047:
3046:
3042:
3033:
3031:
3022:
3021:
3017:
3007:
3005:
2992:
2991:
2987:
2977:
2975:
2962:
2961:
2957:
2947:
2945:
2932:
2931:
2927:
2900:Economic Botany
2897:
2896:
2892:
2870:
2869:
2865:
2860:Wayback Machine
2851:
2847:
2837:
2835:
2828:
2824:
2823:
2814:
2804:
2802:
2793:
2792:
2788:
2778:
2776:
2768:
2767:
2763:
2753:
2751:
2743:
2742:
2738:
2730:
2719:
2715:
2714:
2710:
2680:
2679:
2675:
2645:
2644:
2640:
2604:
2603:
2599:
2594:Wayback Machine
2585:
2581:
2571:
2569:
2564:
2563:
2559:
2523:
2522:
2518:
2482:
2481:
2477:
2421:
2420:
2416:
2387:Yakugaku Zasshi
2381:
2380:
2376:
2324:
2323:
2319:
2310:
2308:
2270:
2269:
2265:
2226:
2225:
2221:
2211:
2209:
2207:
2196:
2189:
2188:
2184:
2169:
2165:
2129:
2128:
2124:
2072:
2071:
2067:
2045:
2044:
2040:
2030:
2028:
2026:fragrantica.com
2020:
2019:
2015:
1989:
1988:
1984:
1966:
1965:
1961:
1942:
1941:
1937:
1905:
1904:
1900:
1884:
1883:
1879:
1861:
1860:
1856:
1822:
1821:
1817:
1808:
1806:
1798:
1797:
1793:
1783:
1781:
1776:
1775:
1768:
1758:
1756:
1751:
1750:
1729:
1725:
1560:
1543:
1526:
1498:
1490:Main articles:
1488:
1450:
1441:
1376:Mullein (genus
1347:Saigon cinnamon
1279:Galium odoratum
1267:Vanilla grass (
1261:Ceylon cinnamon
1256:
1232:
1204:salicylaldehyde
1200:Perkin reaction
1192:
1150:
1122:
1056:
1041:
1037:
1033:
1029:
989:
985:
979:
972:
967:
966:
965: ?)
956:
952:
948:
944:
924:
896:
890:
863:
862:
861:
860:
853:
846:
839:
835:
827:
752:
730:
716:
695:
667:
649:
647:
644:
607:
574:
514:
504:
498:
492:
484:
470:
467:
462:
461:
450:
447:
446:
443:
437:
436:
433:
427:
426:
415:
397:
390:
381:
361:
345:
332:
320:
297:
288:
251:
231:
211:
191:
168:
159:
146:
135:
122:
108:
100:
99:
84:
35:
28:
17:
12:
11:
5:
3740:
3738:
3730:
3729:
3724:
3719:
3714:
3709:
3704:
3694:
3693:
3687:
3686:
3684:
3683:
3678:
3673:
3668:
3663:
3658:
3653:
3648:
3642:
3640:
3636:
3635:
3633:
3632:
3626:
3624:
3620:
3619:
3616:
3615:
3612:
3611:
3609:
3608:
3603:
3598:
3592:
3590:
3586:
3585:
3583:
3582:
3576:
3574:
3570:
3569:
3566:
3565:
3563:
3562:
3557:
3552:
3550:Isopimpinellin
3547:
3541:
3539:
3532:
3531:
3526:
3521:
3516:
3511:
3505:
3503:
3496:
3487:
3483:
3482:
3480:
3479:
3474:
3469:
3464:
3459:
3453:
3451:
3445:
3444:
3441:
3440:
3438:
3437:
3432:
3427:
3422:
3416:
3414:
3407:
3406:
3401:
3396:
3390:
3388:
3382:
3381:
3375:
3373:
3372:
3365:
3358:
3350:
3341:
3340:
3338:
3337:
3331:
3329:
3325:
3324:
3322:
3321:
3316:
3311:
3306:
3301:
3296:
3291:
3286:
3281:
3276:
3271:
3261:
3255:
3253:
3246:
3245:
3239:
3237:
3236:
3229:
3222:
3214:
3207:
3206:
3178:
3153:
3128:
3103:
3068:
3040:
3015:
2998:Access.gpo.gov
2985:
2955:
2938:Access.gpo.gov
2925:
2890:
2863:
2845:
2812:
2786:
2761:
2736:
2708:
2689:(4): 423–453.
2673:
2638:
2597:
2579:
2557:
2516:
2475:
2438:Annual Reviews
2424:Apis mellifera
2414:
2374:
2331:Food Chemistry
2327:Prunus mahaleb
2317:
2287:(3): 211–215.
2263:
2236:(2): 151–159.
2219:
2206:978-9881607416
2205:
2182:
2163:
2122:
2085:Annual Reviews
2065:
2038:
2013:
1982:
1959:
1935:
1898:
1877:
1854:
1835:(2): 161–166.
1815:
1791:
1766:
1726:
1724:
1721:
1712:European Union
1682:Jeffrey Wigand
1626:sweet woodruff
1558:
1542:
1539:
1525:
1522:
1508:are a type of
1487:
1484:
1449:
1446:
1440:
1437:
1418:black currants
1410:
1409:
1396:
1387:cherry blossom
1383:
1374:
1365:
1356:
1355:
1354:
1344:
1335:
1326:
1311:
1301:
1292:
1283:
1274:
1255:
1252:
1242:-hydroxylated
1231:
1228:
1218:, as does the
1196:name reactions
1191:
1188:
1149:
1146:
1121:
1118:
1092:blood clotting
1022:-chromen-2-one
977:
974:
973:
968:
946:
945:
941:standard state
938:
935:
934:
925:
922:
919:
918:
914:
913:
908:
901:
900:
897:
888:
886:
883:
882:
875:
874:
871:
865:
864:
854:
847:
840:
825:
824:
823:
822:
820:
811:
810:
753:
748:
745:
744:
731:
726:
723:
722:
717:
712:
709:
708:
696:
691:
688:
687:
677:
676:
672:
671:
668:
663:
660:
659:
655:
654:
652:10 cm/mol
645:
639:
636:
635:
632:
630:Vapor pressure
626:
625:
622:
613:
612:
585:
579:
578:
575:
570:
567:
566:
563:
557:
556:
553:
547:
546:
543:
537:
536:
533:
527:
526:
523:
519:
518:
512:
506:
505:
502:
496:
490:
485:
480:
477:
476:
472:
471:
469:
468:
465:
457:
456:
455:
452:
451:
449:
448:
444:
441:
440:
438:
434:
431:
430:
422:
421:
420:
417:
416:
414:
413:
400:
398:
386:
383:
382:
380:
379:
371:
369:
363:
362:
360:
359:
355:
353:
347:
346:
344:
343:
335:
333:
325:
322:
321:
319:
318:
310:
308:
302:
301:
298:
293:
290:
289:
287:
286:
282:
280:
272:
271:
261:
253:
252:
250:
249:
241:
239:
233:
232:
230:
229:
221:
219:
213:
212:
210:
209:
201:
199:
193:
192:
190:
189:
181:
179:
173:
172:
169:
164:
161:
160:
158:
157:
149:
147:
140:
137:
136:
134:
133:
125:
123:
118:
115:
114:
110:
109:
106:
102:
101:
93:
92:
86:
85:
83:-Chromen-2-one
78:
72:
71:
67:
66:
58:
57:
49:
48:
15:
13:
10:
9:
6:
4:
3:
2:
3739:
3728:
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3708:
3705:
3703:
3700:
3699:
3697:
3682:
3679:
3677:
3676:Phenprocoumon
3674:
3672:
3669:
3667:
3664:
3662:
3659:
3657:
3654:
3652:
3651:Coumatetralyl
3649:
3647:
3646:Acenocoumarol
3644:
3643:
3641:
3637:
3631:
3628:
3627:
3625:
3621:
3607:
3604:
3602:
3599:
3597:
3594:
3593:
3591:
3587:
3581:
3578:
3577:
3575:
3571:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3543:
3542:
3540:
3536:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3506:
3504:
3500:
3497:
3495:
3491:
3488:
3484:
3478:
3475:
3473:
3470:
3468:
3465:
3463:
3460:
3458:
3455:
3454:
3452:
3450:
3446:
3436:
3433:
3431:
3428:
3426:
3423:
3421:
3418:
3417:
3415:
3411:
3405:
3404:Umbelliferone
3402:
3400:
3397:
3395:
3392:
3391:
3389:
3387:
3383:
3379:
3371:
3366:
3364:
3359:
3357:
3352:
3351:
3348:
3336:
3333:
3332:
3330:
3326:
3320:
3317:
3315:
3312:
3310:
3307:
3305:
3302:
3300:
3299:Allylbenzenes
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3277:
3275:
3272:
3269:
3265:
3262:
3260:
3257:
3256:
3254:
3252:
3247:
3243:
3235:
3230:
3228:
3223:
3221:
3216:
3215:
3212:
3202:
3198:
3194:
3190:
3189:Planta Medica
3182:
3179:
3167:
3163:
3157:
3154:
3142:
3138:
3132:
3129:
3117:
3113:
3107:
3104:
3099:
3095:
3091:
3087:
3083:
3079:
3072:
3069:
3057:
3050:
3044:
3041:
3030:on 2012-01-06
3029:
3025:
3019:
3016:
3003:
2999:
2995:
2989:
2986:
2973:
2969:
2965:
2959:
2956:
2943:
2939:
2935:
2929:
2926:
2921:
2917:
2913:
2909:
2905:
2901:
2894:
2891:
2886:
2882:
2878:
2874:
2867:
2864:
2861:
2857:
2854:
2849:
2846:
2834:
2827:
2821:
2819:
2817:
2813:
2800:
2796:
2790:
2787:
2775:
2771:
2765:
2762:
2750:
2746:
2740:
2737:
2729:
2725:
2718:
2712:
2709:
2704:
2700:
2696:
2692:
2688:
2684:
2677:
2674:
2669:
2665:
2661:
2657:
2654:(2): 247–58.
2653:
2649:
2642:
2639:
2634:
2630:
2625:
2620:
2617:(2): 249–57.
2616:
2612:
2608:
2601:
2598:
2595:
2591:
2588:
2583:
2580:
2567:
2561:
2558:
2553:
2549:
2544:
2539:
2535:
2531:
2530:J. Biol. Chem
2527:
2520:
2517:
2512:
2508:
2503:
2498:
2495:(1): 97–107.
2494:
2490:
2486:
2479:
2476:
2471:
2467:
2463:
2459:
2455:
2451:
2447:
2443:
2439:
2435:
2431:
2430:
2425:
2418:
2415:
2410:
2406:
2401:
2396:
2393:(6): 311–21.
2392:
2388:
2385:
2378:
2375:
2370:
2366:
2362:
2358:
2353:
2348:
2344:
2340:
2336:
2332:
2328:
2321:
2318:
2307:on 2013-01-05
2306:
2302:
2298:
2294:
2290:
2286:
2282:
2278:
2276:
2267:
2264:
2259:
2255:
2251:
2247:
2243:
2239:
2235:
2231:
2223:
2220:
2208:
2202:
2195:
2194:
2186:
2183:
2179:
2175:
2172:
2167:
2164:
2159:
2155:
2150:
2145:
2141:
2137:
2133:
2126:
2123:
2118:
2114:
2110:
2106:
2102:
2098:
2094:
2090:
2086:
2082:
2078:
2077:
2069:
2066:
2061:
2057:
2053:
2049:
2042:
2039:
2027:
2023:
2017:
2014:
2009:
2005:
2001:
1997:
1993:
1986:
1983:
1978:
1974:
1970:
1963:
1960:
1956:
1954:
1948:
1947:
1939:
1936:
1932:
1930:
1926:
1922:
1917:: 303. 1825.
1916:
1912:
1908:
1902:
1899:
1894:
1890:
1889:
1881:
1878:
1873:
1870:(in French).
1869:
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1659:
1658:acenocoumarol
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1470:cinnamic acid
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1458:hydroxylation
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3722:Plant toxins
3538:O-Methylated
3413:O-Methylated
3377:
3335:Rhododendrin
3283:
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3188:
3181:
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2873:Food Control
2872:
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2848:
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1577:for humans.
1544:
1535:pipe tobacco
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1518:rodenticides
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1454:biosynthesis
1451:
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1430:
1414:strawberries
1411:
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1358:Deertongue (
1351:C. loureiroi
1350:
1340:C. burmannii
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1158:benzoic acid
1151:
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1017:
981:
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932:2-Cumaranone
878:
815:
719:
681:
618:
351:RTECS number
113:Identifiers
105:Other names
95:
80:
3671:Hymecromone
3606:Imperatorin
3601:Bergamottin
3555:Methoxsalen
3529:Xanthotoxol
3486:Derivatives
3304:Stilbenoids
3279:Monolignols
3249:Classes of
3146:30 December
3121:30 December
3008:30 December
2948:30 December
2805:30 December
2779:30 December
2774:Bfr.bund.de
2754:30 December
2489:Circulation
2440:: 185–208.
2352:2158/775163
2180:, 4470–4476
2087:: 631–658.
2031:13 November
1784:24 December
1717:mulled wine
1684:to contact
1676:tobacco by
1648:bison grass
1582:cassia bark
1486:Derivatives
1466:cyclization
1401:Glycyrrhiza
1198:, with the
1154:tonka beans
1134:, from the
1106:blood clots
1069:benzopyrone
1061:heterocycle
893:median dose
879:Lethal dose
869:Flash point
714:Signal word
608:soluble in
522:Appearance
475:Properties
264:100.001.897
186:CHEBI:28794
3696:Categories
3630:Dicoumarol
3560:Trioxsalen
3449:Glycosides
3435:Scopoletin
3394:Aesculetin
3294:Flavonoids
3171:2 December
3061:2 December
3034:2012-07-19
2978:17 January
2566:"Warfarin"
2311:2010-06-26
1979:: 172–178.
1921:coumarine,
1874:: 305–309.
1809:2023-12-20
1753:"Coumarin"
1723:References
1696:rat poison
1691:60 Minutes
1575:carcinogen
1502:dicoumarol
1462:glycolysis
1448:Metabolism
1304:Tonka bean
1132:tonka bean
693:Pictograms
658:Structure
597:chloroform
583:Solubility
510:Molar mass
376:A4VZ22K1WT
217:ChemSpider
206:ChEMBL6466
141:3D model (
120:CAS Number
76:IUPAC name
3712:Fuel dyes
3702:Coumarins
3656:Ensaculin
3639:Synthetic
3623:Oligomers
3596:Auraptene
3545:Bergapten
3509:Angelicin
3502:Aglycones
3425:Herniarin
3386:Aglycones
3378:coumarins
3376:Types of
3289:Chalcones
3284:Coumarins
3264:Chromones
3240:Types of
2470:221165130
2454:0066-4170
2250:0378-8741
2158:104289832
2142:: 50–57.
2117:212740956
2101:1543-5008
2002:: 53–63.
1953:coumarine
1674:cigarette
1623:flavorant
1514:vitamin K
1379:Verbascum
1331:C. cassia
1297:Melilotus
1224:chromones
1190:Synthesis
1170:coumarine
1120:Etymology
1088:vitamin K
800:P333+P313
784:P302+P352
780:P301+P312
684:labelling
358:GN4200000
285:202-086-7
277:EC Number
38:Coumarin
3681:Warfarin
3519:Psoralen
3514:Marmesin
3472:Scopolin
3457:Aesculin
3420:Fraxetin
3328:Examples
3319:Suberins
3098:11408097
2920:23232507
2856:Archived
2838:28 March
2749:Osha.gov
2703:10418958
2668:12480300
2633:15141102
2590:Archived
2572:13 April
2511:13619027
2462:32806934
2369:14467019
2361:22980784
2301:84525194
2258:10771205
2109:32176525
2054:: 1–62.
1759:13 April
1700:coumadin
1642:Żubrówka
1586:cinnamon
1541:Toxicity
1433:propolis
1426:cherries
1422:apricots
1408:derives.
1406:licorice
1314:Cinnamon
1202:between
1136:Old Tupi
1127:coumarou
1102:warfarin
1049:hydrogen
982:Coumarin
928:Chromone
816:NFPA 704
675:Hazards
643:(χ)
605:pyridine
237:DrugBank
226:13848793
32:warfarin
3580:Apterin
3524:Vaginol
3467:Skimmin
3399:Ferujol
3314:Lignins
3309:Lignans
2833:bund.de
2799:NPR.org
2552:1339448
2409:1941536
2178:61 (18)
1837:Bibcode
1635:Maiwein
1563:epoxide
1551:kidneys
1184:fougère
1148:History
1080:vanilla
1065:carbons
1053:lactone
1045:benzene
963:what is
961: (
720:Warning
610:ethanol
541:Density
515:146.145
327:PubChem
300:165222
246:DB04665
171:383644
130:91-64-5
3462:Fraxin
3430:Osthol
3096:
2918:
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1604:muesli
1475:UGT1A8
1464:, and
1424:, and
1392:Prunus
1367:Tilo (
1216:phenol
1141:kumarú
1112:, and
958:verify
955:
907:(SDS)
459:SMILES
315:D07751
197:ChEMBL
70:Names
3195:(5).
3052:(PDF)
2916:S2CID
2829:(PDF)
2731:(PDF)
2720:(PDF)
2466:S2CID
2436:(1).
2365:S2CID
2297:S2CID
2197:(PDF)
2154:S2CID
2113:S2CID
2083:(1).
1891:[
1385:Many
1240:ortho
1234:From
1055:ring
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648:−82.5
624:1.39
589:ether
424:InChI
177:ChEBI
143:JSmol
3173:2018
3148:2015
3123:2015
3094:PMID
3063:2018
3010:2015
2980:2022
2950:2015
2840:2018
2807:2015
2781:2015
2756:2015
2699:PMID
2664:PMID
2629:PMID
2574:2019
2548:PMID
2507:PMID
2458:PMID
2450:ISSN
2405:PMID
2357:PMID
2329:L".
2254:PMID
2246:ISSN
2214:2020
2201:ISBN
2105:PMID
2097:ISSN
2033:2020
1931:...]
1786:2016
1761:2019
1549:and
1524:Uses
1494:and
1478:has
1452:The
1206:and
1076:odor
808:P501
804:P363
796:P330
792:P321
788:P314
776:P280
772:P272
768:P270
764:P264
760:P261
756:P260
742:H373
738:H317
734:H302
617:log
531:Odor
367:UNII
306:KEGG
3197:doi
3086:doi
2908:doi
2881:doi
2691:doi
2656:doi
2619:doi
2538:doi
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2347:hdl
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2238:doi
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2004:doi
1845:doi
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1686:CBS
1660:or
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