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Scopolin

From Wikipedia, the free encyclopedia

Scopolin
Names

IUPAC name 7-(β-D-Glucopyranosyloxy)-6-methoxy-2H-1-benzopyran-2-one
Systematic IUPAC name 6-Methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-1-benzopyran-2-one
Identifiers
CAS Number	531-44-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16065^Y
ChemSpider	388609
PubChem CID	439514
UNII	1Y49270PY8^Y
CompTox Dashboard(EPA)	DTXSID20967621
InChI InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1 Key: SGTCGCCQZOUMJJ-YMILTQATSA-N InChI=1/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1 Key: SGTCGCCQZOUMJJ-YMILTQATBT
SMILES COC1=C(C=C2C(=C1)C=CC(=O)O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
Properties
Chemical formula	C₁₆H₁₈O₉
Molar mass	354.311 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Scopolin is aglucoside ofscopoletin formed by the action of theenzyme scopoletin glucosyltransferase.^[1] It occurs inChamaemelum nobile.^[2]

References

^Hino F, Okazaki M and Miura Y (1982)."Effect of 2,4-dichlorophenoxyacetic acid on glucosylation of scopoletin to scopolin in tobacco tissue-culture".Plant Physiol.69 (4):810–813.doi:10.1104/pp.69.4.810.PMC 426310.PMID 16662301.
^Hänsel, Rudolf; Sticher, Otto (2010).Pharmakognosie – Phytopharmazie (in German) (9th ed.). Springer Medizin Verlag. p. 1076.doi:10.1007/978-3-642-00963-1.ISBN 978-3-642-00962-4.

Bibliography

Steck, Warren (1967). "Biosynthesis of Scopolin in Tobacco".Canadian Journal of Biochemistry.45 (6):889–896.doi:10.1139/o67-099.ISSN 1208-6002.PMID 6034703.
Steck, Warren (1967). "The Biosynthetic Pathway from Caffeic Acid to Scopolin in Tobacco Leaves".Canadian Journal of Biochemistry.45 (12):1995–2003.doi:10.1139/o67-233.ISSN 1208-6002.PMID 6082583.

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Types ofcoumarins

O-Methylated	Fraxetin Herniarin Osthol Scopoletin

Derivatives

Furanocoumarins

Aglycones

O-Methylated	Bergapten Isopimpinellin Methoxsalen Trioxsalen

Furanocoumarin glycosides

Apterin

Meroterpene furanocoumarin ether

Oligomers

Dicoumarol

Synthetic

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