Scopoletin

Scopoletin

Names
IUPAC name 7-hydroxy-6-methoxychromen-2-one
Other names Gelseminic acid Chrysatropic acid Scopoletine 6-Methylesculetin Murrayetin Scopoletol Escopoletin Methylesculetin 6-O-Methylesculetin Esculetin-6-methyl ether 7-Hydroxy-5-methoxycoumarin 6-Methoxyumbelliferone
Identifiers
CAS Number	92-61-5
ChemSpider	4444113
Jmol interactive 3D	Image
PubChem	5280460
InChI InChI=1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3 Key: RODXRVNMMDRFIK-UHFFFAOYSA-N InChI=1/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3 Key: RODXRVNMMDRFIK-UHFFFAOYAG
SMILES COC1=C(C=C2C(=C1)C=CC(=O)O2)O
Properties
Chemical formula	C10H8O4
Molar mass	192.16 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Scopoletin is a coumarin found in the root of plants in the genus Scopolia such as Scopolia carniolica and Scopolia japonica, in chicory, in Artemisia scoparia, in the roots and leaves of Stinging Nettle (Urtica dioica ), in the passion flower, in Brunfelsia, in Viburnum prunifolium, in Solanum nigrum,^[1] in Mallotus resinosus,^[2] or and in Kleinhovia hospita. It can also be found in vinegar,^[3] some whiskies or in dandelion coffee. A similar coumarin is scoparone.

Glycosides

Scopolin is a glucoside of scopoletin formed by the action of the enzyme, scopoletin glucosyltransferase.

References

1. Zhao Y, Liu F, Lou HX (2010). "[Studies on the chemical constituents of Solanum nigrum]". Zhong Yao Cai (in Chinese) 33 (4): 555–556. PMID 20845784.
2. Ma J, Jones SH, Hecht SM (2004). "A coumarin from Mallotus resinosus that mediates DNA cleavage". J Nat Prod 67 (9): 1614–1616. doi:10.1021/np040129c. PMID 15387675.
3. Analysis of polyphenolic compounds of different vinegar samples. Miguel Carrero Gálvez, Carmelo García Barroso and Juan Antonio Pérez-Bustamante, Zeitschrift für Lebensmitteluntersuhung und -Forschung A, Volume 199, Number 1, pages 29-31, doi:10.1007/BF01192948