Scopolin

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16065 ;
ChemSpider	388609;
PubChem CID	439514;
UNII	1Y49270PY8 ;
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 their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Scopolin is a glucoside of scopoletin formed by the action of the enzyme scopoletin glucosyltransferase.^[1] It occurs in Chamaemelum nobile.^[2]

Biosynthesis

Scopoletin glucosyltransferase transfers a glucose unit from UDP-glucose to form scopoletin from scopolin:

The enzyme has been characterised from tobacco and Duboisia myoporoides.^[1]^[3]^[4]

1 2 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.
↑ 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.
↑ Betry, P.; Fliniaux, M.A.; Mackova, M.; Gillet, F.; Macek, T.; Jacquin-Dubreuil, A. (1995). "Scopoletin-glucosyltransferase Activity from Duboisia myoporoides; Improvement of Cultivation Conditions and Crude Extract Preparation Procedure". Journal of Plant Physiology. 146 (4): 503–507. Bibcode:1995JPPhy.146..503B. doi:10.1016/S0176-1617(11)82015-8. ISSN 0176-1617.