Scopoletin

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Scopoletin
Chemical structure of scopoletin
Names
Preferred IUPAC name
7-Hydroxy-6-methoxy-2H-1-benzopyran-2-one
Other names
7-Hydroxy-6-methoxy-2H-chromen-2-one
7-Hydroxy-6-methoxychromen-2-one
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
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.001.975
Properties
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[1] 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,[2] in Mallotus resinosus,[3] or and in Kleinhovia hospita. It can also be found in fenugreek,[1] vinegar,[4] some whiskies or in dandelion coffee. A similar coumarin is scoparone.

Glycosides[edit]

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

References[edit]

  1. ^ a b Ouzir, M; El Bairi, K; Amzazi, S (October 2016). "Toxicological properties of fenugreek (Trigonella foenum graecum).". Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 96: 145–54. doi:10.1016/j.fct.2016.08.003. PMID 27498339. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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