Scopolin: Difference between revisions

Scopolin
Names
	IUPAC name 7-(β-D-Glucopyranosyloxy)-6-methoxy-2H-1-benzopyran-2-one
	Preferred 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

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Revision as of 14:54, 6 January 2023

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

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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-'''Scopolin''' is a [[glucoside]] of [[scopoletin]] formed by the action of the [[enzyme]] [[scopoletin glucosyltransferase]].<ref>{{cite journal | author = Hino F, Okazaki M and Miura Y | year = 1982 | title = Effect of 2,4-dichlorophenoxyacetic acid on glucosylation of scopoletin to scopolin in tobacco tissue-culture | journal = [[Plant Physiol.]]  | volume = 69 | pages = 810&ndash;813 | doi = 10.1104/pp.69.4.810 | pmid=16662301 | issue = 4 | pmc = 426310}}</ref>
+'''Scopolin''' is a [[glucoside]] of [[scopoletin]] formed by the action of the [[enzyme]] [[scopoletin glucosyltransferase]].<ref>{{cite journal | author = Hino F, Okazaki M and Miura Y | year = 1982 | title = Effect of 2,4-dichlorophenoxyacetic acid on glucosylation of scopoletin to scopolin in tobacco tissue-culture | journal = [[Plant Physiol.]]  | volume = 69 | pages = 810&ndash;813 | doi = 10.1104/pp.69.4.810 | pmid=16662301 | issue = 4 | pmc = 426310}}</ref> It occurs in [[Chamaemelum nobile]].<ref>{{Cite book |last=Hänsel |first=Rudolf |url=https://link.springer.com/book/10.1007/978-3-642-00963-1 |title=Pharmakognosie – Phytopharmazie |last2=Sticher |first2=Otto |publisher=Springer Medizin Verlag |year=2010 |isbn=978-3-642-00962-4 |edition=9th |pages=1076 |language=de}}</ref>
 == References ==