137:
926:
737:
375:
300:
800:
863:
128:
952:
1180:
24:
522:
984:
1020:
values of 3.9, 3.95 and 4.15 respectively, and it fluoresces blue in both ultraviolet and visible light. The powerful absorption at three different wavelengths, coupled with the fact that the energy is dissipated safely as visible light, make umbelliferone a useful sunscreen agent. The absorption
921:
858:
795:
1393:
Leal LK, A. A. G. Ferreira, G. A. Bezerra, F. J. A.Matos, G. S. B. Viana (May 2000). "Antinociceptive, anti-inflammatory and bronchodilator activities of
Brazilian medicinal plants containing coumarin: a comparative study".
535:
947:
1660:
424:
869:
806:
743:
983:
1644:
1621:
1602:
1500:
1084:
1687:
1458:
1233:"Anti-mutagenic effects of coumarin and umbelliferone on mutagenesis induced by 4-nitroquinoline 1-oxide or UV irradiation in e. Coli"
1551:
P. Satyanarayana, P. Subrahmanyam, R. Kasai, O. Tanaka (1985). "An apiose-containing coumarin glycoside from gmelina arborea root".
389:
107:
925:
727:
group. Finally an intramolecular attack from the hydroxyl group of C2' to the carboxylic acid group closes the ring and forms the
1438:
45:
41:
736:
88:
60:
542:
2036:
799:
332:
719:. The 4-coumaric acid is again hydroxylated by cinnamate/coumarate 2-hydroxylase to yield 2,4-dihydroxy-cinnamic acid (
127:
1796:
1189:
700:
353:
1087:, the primary enzyme responsible for the conversion of 4-androstene-3,17-dione to testosterone, with IC50 of 1.4 μM.
67:
1034:
217:
34:
2031:
2026:
74:
862:
712:
598:
It is a yellowish-white crystalline solid that has a slight solubility in hot water, but high solubility in
499:
295:
1680:
56:
964:
653:
257:
932:
1980:
1560:
149:
1319:
1136:
675:
647:
370:
183:
2021:
1985:
1462:
1272:"Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore"
1105:
1053:
1017:
951:
1673:
1640:
1617:
1598:
1533:
1496:
1419:
1411:
1375:
1301:
1252:
994:
696:
277:
1568:
1525:
1470:
1454:
1403:
1365:
1357:
1291:
1283:
1244:
1147:
447:
1179:
341:
81:
1194:
724:
716:
692:
688:
666:
642:
1564:
1346:"Anti-inflammatory and antioxidant effects of umbelliferone in chronic alcohol-fed rats"
587:
light strongly at several wavelengths. There are some indications that this chemical is
374:
299:
237:
193:
1869:
1813:
1591:
1370:
1345:
1296:
1271:
1155:
513:
1572:
1407:
2015:
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1965:
1248:
1159:
1030:
720:
708:
704:
619:
588:
488:
288:
1466:
321:
1069:
916:{\displaystyle {\begin{matrix}{}\\{\xrightarrow {\mathrm {C2H} }}\\{}\end{matrix}}}
853:{\displaystyle {\begin{matrix}{}\\{\xrightarrow {\mathrm {C4H} }}\\{}\end{matrix}}}
790:{\displaystyle {\begin{matrix}{}\\{\xrightarrow {\mathrm {PAL} }}\\{}\end{matrix}}}
611:
136:
1287:
1990:
1925:
1920:
1874:
1848:
1132:
1061:
584:
23:
1103:-methylumbelliferone or 7-methoxycoumarin) occurs in the leaves of water hemp (
1949:
1879:
1754:
1713:
1207:
1151:
972:
968:
661:
470:
268:
1529:
1516:
Poirier D (Mar 2003). "Inhibitors of 17 beta-hydroxysteroid dehydrogenases".
1415:
1361:
1095:
Umbelliferone is the parent compound for a large number of natural products.
1975:
1915:
1864:
1828:
1768:
1744:
1212:
1167:
1111:
1096:
1065:
1049:
1013:
998:
645:, as well as in plants from other families, such as the mouse-ear hawkweed (
638:
592:
1537:
1423:
1379:
1305:
1232:
1256:
2000:
1838:
1833:
1791:
1776:
1739:
1705:
1697:
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1459:
10.1002/(SICI)1099-1573(199705)11:3<211::AID-PTR72>3.0.CO;2-W
1171:
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1143:
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577:
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1843:
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1718:
1120:
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728:
599:
308:
723:) followed by a bond rotation of the unsaturated bond adjacent to the
1781:
1749:
1665:
1139:
1073:
1022:
634:
248:
888:
825:
762:
512:
Except where otherwise noted, data are given for materials in their
1131:-glucopyranosylumbelliferone) occur naturally and are used for the
614:
family of plants, and the plant family in turn was named for their
1178:
623:
595:. Umbelliferone has been reported to have antioxidant properties.
228:
216:
206:
1669:
1437:
Lino CS, M. L. Taveira, G. S. B. Viana, F. J. A. Matos (1997).
1048:
The ultraviolet activity of umbelliferone led to its use as a
17:
982:
358:
1443:
Jacq and its main constituents: coumarin and umbelliferone"
1231:
Ohta T, Watanabe K, Moriya M, Shirasu Y, Kada T (1983).
398:
InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
1344:
Sim MO, Lee HI, Ham JR, Seo KI, Kim MJ, Lee MK (2015).
530:
408:
InChI=1/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
874:
811:
748:
629:
Umbelliferone occurs in many familiar plants from the
987:
The
Pechmann condensation as applied to umbelliferone
963:
Umbelliferone is traditionally synthesized using the
935:
872:
809:
746:
1958:
1942:
1908:
1892:
1857:
1821:
1812:
1805:
1767:
1732:
1704:
1012:Umbelliferone absorbs strongly at 300, 305 and 325
493:230 °C (446 °F; 503 K) (decomposes)
48:. Unsourced material may be challenged and removed.
1590:
1080:. It acts as a pH indicator in the range 6.5-8.9.
941:
915:
852:
789:
1631:Barton D, Nakanishi K, Meth-Cohn O, eds. (1999).
320:
1183:Herniarin and marmin, umbelliferone derivatives
192:
1439:"Analgesic and antiinflammatory activities of
1083:Umbelliferone is a potent inhibitor of type 3
1681:
657:, Hydrangeaceae, under the name hydrangine).
8:
483:yellowish-white crystalline odorless powder
1616:(4th ed.). Oxford: Blackwell Science.
167:7-hydroxycoumarin, hydrangine, skimmetine,
1854:
1818:
1809:
1729:
1688:
1674:
1666:
373:
298:
276:
119:
1593:Naturally Occurring Oxygen Ring Compounds
1369:
1295:
1146:derivatives are also widespread, such as
934:
907:
889:
883:
877:
873:
871:
844:
826:
820:
814:
810:
808:
781:
763:
757:
751:
747:
745:
664:, the dried latex from the giant fennel (
340:
108:Learn how and when to remove this message
1633:Comprehensive Natural Products Chemistry
651:, Asteraceae) or the bigleaf hydrangea (
1223:
429:
394:
369:
971:and formylacetic acid (generated from
289:
401:Key: ORHBXUUXSCNDEV-UHFFFAOYSA-N
256:
236:
7:
1495:. I. K. International. p. 211.
695:, which in turn is produced via the
46:adding citations to reliable sources
1493:Intermediates for Organic Synthesis
411:Key: ORHBXUUXSCNDEV-UHFFFAOYAL
311:
1119:-Glycosylated derivatives such as
896:
890:
833:
827:
770:
767:
764:
14:
1192:can be isolated from the root of
1072:indicator for metal ions such as
1068:. Umbelliferone can be used as a
610:Umbelliferone's name is from the
1909:Meroterpene furanocoumarin ether
1797:Umbelliferone 7-apiosylglucoside
1190:Umbelliferone 7-apiosylglucoside
1085:17β-hydroxysteroid dehydrogenase
950:
942:{\displaystyle \longrightarrow }
924:
861:
798:
735:
691:and as such is synthesized from
520:
135:
126:
22:
660:It is one of the components of
516:(at 25 °C , 100 kPa).
33:needs additional citations for
936:
633:(Umbelliferae) family such as
576:, is a natural product of the
1:
1573:10.1016/S0031-9422(00)82575-3
1408:10.1016/S0378-8741(99)00165-8
1060:. It has also been used as a
1025:solution, since the phenolic
1396:Journal of Ethnopharmacology
1288:10.1016/j.tetlet.2008.03.063
1249:10.1016/0165-1218(83)90160-x
1154:skin and in the bark of the
606:Natural occurrences and name
1491:Ahluwalia VK (2010-09-30).
2053:
475:162.14 g/mol
1893:Furanocoumarin glycosides
1612:Joule J, Mills K (2000).
510:
440:
420:
385:
176:
164:
148:
143:
134:
125:
1597:. London: Butterworths.
1530:10.2174/0929867033368222
1362:10.4162/nrp.2015.9.4.364
1008:Ultraviolet fluorescence
1635:. Vol. 2. Oxford:
993:A newer synthesis uses
713:cinnamate 4-hydroxylase
500:Magnetic susceptibility
1614:Heterocyclic Chemistry
1324:www.chemicalland21.com
1184:
988:
943:
917:
854:
791:
1661:USDA ARS info on uses
1447:Phytotherapy Research
1182:
986:
965:Pechmann condensation
944:
918:
855:
792:
654:Hydrangea macrophylla
432:c1cc(cc2c1ccc(=O)o2)O
1981:Ethyl biscoumacetate
933:
870:
807:
744:
673:It is also found in
150:Preferred IUPAC name
42:improve this article
2037:Sunscreening agents
1565:1985PChem..24.1862S
1441:Justicia pectoralis
1276:Tetrahedron Letters
1137:glycoside hydrolase
1109:) and rupturewort (
900:
837:
774:
699:. Phenylalanine is
687:Umbelliferone is a
676:Justicia pectoralis
648:Hieracium pilosella
158:-1-benzopyran-2-one
122:
1986:4-Hydroxycoumarins
1185:
1106:Eupatorium ayapana
1054:optical brightener
989:
959:Chemical synthesis
939:
913:
911:
850:
848:
787:
785:
543:Infobox references
120:
2009:
2008:
1938:
1937:
1934:
1933:
1888:
1887:
1763:
1762:
1646:978-0-08-043154-3
1623:978-0-632-05453-4
1604:978-0-408-26750-2
1502:978-81-88237-33-3
1282:(19): 3045–3048.
1237:Mutation Research
1135:determination of
1130:
995:methyl propionate
901:
838:
775:
697:shikimate pathway
622:, each called an
559:7-hydroxycoumarin
551:Chemical compound
549:
548:
506:-88.22·10 cm/mol
354:CompTox Dashboard
218:Interactive image
118:
117:
110:
92:
2044:
2032:Laser gain media
2027:Fluorescent dyes
1855:
1819:
1810:
1730:
1690:
1683:
1676:
1667:
1650:
1627:
1608:
1596:
1577:
1576:
1559:(8): 1862–1863.
1548:
1542:
1541:
1513:
1507:
1506:
1488:
1482:
1481:
1479:
1478:
1469:. Archived from
1434:
1428:
1427:
1390:
1384:
1383:
1373:
1341:
1335:
1334:
1332:
1330:
1316:
1310:
1309:
1299:
1267:
1261:
1260:
1243:(1–2): 135–138.
1228:
1128:
954:
948:
946:
945:
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928:
922:
920:
919:
914:
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782:
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773:
758:
752:
739:
591:, it is used in
557:, also known as
533:
527:
524:
523:
448:Chemical formula
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139:
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99:
93:
91:
50:
26:
18:
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2051:
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2046:
2045:
2043:
2042:
2041:
2012:
2011:
2010:
2005:
1954:
1930:
1904:
1884:
1853:
1814:Furanocoumarins
1801:
1759:
1728:
1700:
1694:
1657:
1647:
1639:. p. 677.
1630:
1624:
1611:
1605:
1589:Dean F (1963).
1588:
1585:
1583:Further reading
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1328:
1326:
1320:"UMBELLIFERONE"
1318:
1317:
1313:
1269:
1268:
1264:
1230:
1229:
1225:
1221:
1204:
1195:Gmelina arborea
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1038:
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816:
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804:
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753:
742:
741:
731:umbelliferone.
725:carboxylic acid
717:4-coumaric acid
693:L-phenylalanine
689:phenylpropanoid
685:
679:(Acanthaceae).
667:Ferula communis
643:garden angelica
608:
552:
545:
540:
539:
538: ?)
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57:"Umbelliferone"
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5:
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1870:Isopimpinellin
1867:
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1655:External links
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1553:Phytochemistry
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1524:(6): 453–477.
1508:
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1483:
1453:(3): 211–215.
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1402:(2): 151–159.
1385:
1356:(4): 364–369.
1350:Nutr Res Pract
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733:
707:, followed by
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681:
620:inflorescences
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604:
574:-umbelliferone
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514:standard state
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121:Umbelliferone
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1996:Phenprocoumon
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1971:Coumatetralyl
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1966:Acenocoumarol
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1724:Umbelliferone
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1518:Curr Med Chem
1512:
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1473:on 2013-01-05
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1277:
1273:
1270:Du L (2008).
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1160:furocoumarins
1157:
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1149:
1145:
1144:Isoprenylated
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1108:
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927:
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885:
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759:
738:
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730:
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721:umbellic acid
718:
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709:hydroxylation
706:
705:cinnamic acid
702:
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589:antimutagenic
586:
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555:Umbelliferone
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489:Melting point
487:
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371:DTXSID5052626
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290:ECHA InfoCard
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59: –
58:
54:
53:Find sources:
47:
43:
37:
36:
31:This article
29:
25:
20:
19:
16:
1858:O-Methylated
1733:O-Methylated
1723:
1632:
1613:
1592:
1556:
1552:
1546:
1521:
1517:
1511:
1492:
1486:
1475:. Retrieved
1471:the original
1450:
1446:
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1432:
1399:
1395:
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1349:
1339:
1327:. Retrieved
1323:
1314:
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1240:
1236:
1226:
1193:
1188:
1133:fluorimetric
1124:
1116:
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1100:
1094:
1082:
1070:fluorescence
1047:
1031:deprotonated
1011:
992:
975:
962:
734:
686:
683:Biosynthesis
674:
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665:
659:
652:
646:
628:
612:umbelliferae
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571:
570:
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554:
553:
177:Identifiers
168:
165:Other names
155:
104:
95:
85:
78:
71:
64:
52:
40:Please help
35:verification
32:
15:
1991:Hymecromone
1926:Imperatorin
1921:Bergamottin
1875:Methoxsalen
1849:Xanthotoxol
1806:Derivatives
1329:21 November
1091:Derivatives
1062:gain medium
1021:changes in
1016:, with log
585:ultraviolet
583:It absorbs
480:Appearance
441:Properties
296:100.002.038
258:ChEMBL51628
238:CHEBI:27510
154:7-Hydroxy-2
2016:Categories
1950:Dicoumarol
1880:Trioxsalen
1769:Glycosides
1755:Scopoletin
1714:Aesculetin
1477:2010-06-26
1219:References
1213:Laser dyes
1208:Aesculetin
1158:tree) and
1152:grapefruit
1150:(found in
1066:dye lasers
973:malic acid
969:resorcinol
662:asafoetida
593:sunscreens
567:skimmetine
563:hydrangine
471:Molar mass
342:60Z60NTL4G
269:ChemSpider
205:3D model (
184:CAS Number
98:March 2020
68:newspapers
2022:Coumarins
1976:Ensaculin
1959:Synthetic
1943:Oligomers
1916:Auraptene
1865:Bergapten
1829:Angelicin
1822:Aglycones
1745:Herniarin
1706:Aglycones
1698:coumarins
1696:Types of
1416:0378-8741
1168:angelicin
1112:Herniaria
1097:Herniarin
1050:sunscreen
1029:group is
999:palladium
937:⟶
715:to yield
639:coriander
2001:Warfarin
1839:Psoralen
1834:Marmesin
1792:Scopolin
1777:Aesculin
1740:Fraxetin
1637:Elsevier
1538:12570693
1467:84525194
1424:10771205
1380:26244074
1306:19081820
1202:See also
1172:psoralen
1164:marmesin
1162:such as
1058:textiles
1040:= 7.7).
1027:hydroxyl
1023:alkaline
1002:catalyst
886:→
823:→
760:→
631:Apiaceae
618:-shaped
616:umbrella
580:family.
578:coumarin
502:(χ)
1900:Apterin
1844:Vaginol
1787:Skimmin
1719:Ferujol
1561:Bibcode
1371:4523479
1297:2490821
1257:6403855
1140:enzymes
1121:skimmin
1078:calcium
976:in situ
967:, from
729:lactone
600:ethanol
536:what is
534: (
465:
322:5281426
309:PubChem
278:4444774
194:93-35-6
82:scholar
1782:Fraxin
1750:Osthol
1643:
1620:
1601:
1536:
1499:
1465:
1422:
1414:
1378:
1368:
1304:
1294:
1255:
1170:, and
1148:marmin
1074:copper
997:and a
949:
929:
923:
866:
860:
803:
797:
740:
701:lyased
635:carrot
569:, and
531:verify
528:
425:SMILES
249:ChEMBL
144:Names
84:
77:
70:
63:
55:
1463:S2CID
703:into
624:umbel
390:InChI
229:ChEBI
207:JSmol
89:JSTOR
75:books
1641:ISBN
1618:ISBN
1599:ISBN
1534:PMID
1497:ISBN
1420:PMID
1412:ISSN
1376:PMID
1331:2011
1302:PMID
1253:PMID
1156:Bael
1076:and
1064:for
1056:for
1044:Uses
641:and
572:beta
333:UNII
169:beta
61:news
1569:doi
1526:doi
1455:doi
1404:doi
1366:PMC
1358:doi
1292:PMC
1284:doi
1245:doi
1241:117
1127:-β-
1123:(7-
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711:by
670:).
359:EPA
312:CID
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