Ombuin

Ombuin
Names
	IUPAC name 3,5-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxychromen-4-one
	Other names 4',7-Dimethylquercetin; 7,4'-Di-O-methylquercetin; 4',7-Dimethoxy-3,3',5-trihydroxyflavone
Identifiers
CAS Number	529-40-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:67493 ;
ChemSpider	4478412 ;
PubChem CID	5320287;
UNII	Z3K3F0YR3W ;
CompTox Dashboard (EPA)	DTXSID00200942 ;
	InChI InChI=1S/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-12(23-2)10(18)5-8/h3-7,18-19,21H,1-2H3 Key: BWORNNDZQGOKBY-UHFFFAOYSA-N ; InChI=1/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-12(23-2)10(18)5-8/h3-7,18-19,21H,1-2H3 Key: BWORNNDZQGOKBY-UHFFFAOYAW;
	SMILES COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)O)O;
Properties
Chemical formula	C17H14O7
Molar mass	330.29 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Ombuin is an O-methylated flavonol, a type of flavonoid. It is the 4',7-O-methyl derivative of quercetin.

Ombuin can be found in species of the genus Erythroxylum. It can also be synthetized.[1] Ombuin 3-sulfate can be isolated from Flaveria chlorifolia.[2]

Glycosides

Ombuin-3-rutinoside can be isolated from Phytolacca dioica, the ombu tree.[3] Ombuin-3-O-rhamnosylglucoside can be found in Erythroxylum rufum.[4]
Other glycosides (ombuosides) :

Ombuin 3-galactoside (C₂₃H₂₄O₁₂, CAS number 69168-13-4)
Ombuin 3-glucoside (C₂₃H₂₄O₁₂, CAS number 158642-42-3)

References

Partial methylation of quercetin: Direct synthesis of tamarixetin, ombuin and ayanin. Koppaka V. Rao, Jacob A. Owoyale, Journal of Heterocyclic Chemistry, Volume 13 Issue 6, Pages 1293 - 1295
Ombuin 3-sulphate from Flaveria chloraefolia. Denis Barron and Ragai K. Ibrahim, Phytochemistry, Volume 27, Issue 7, 1988, pages 2362-2363, doi:10.1016/0031-9422(88)80166-3
Über die Synthese von Quercetin-3-glykosiden, II. Synthese des Ombuosids und eine rationelle Synthese von Rutin. Ludwig Hörhammer, Hildebert Wagner, Hans-Günther Arndt, Gustav Hitzler, Lorand Farkas, Chemische Berichte, Volume 101 Issue 4, Pp 1183-1185, 1968 (German)
Flavonoids of Erythroxylum rufum and Erythroxylum ulei. Bruce A. Bohm, David W. Phillips and Fred R. Gander, J. Nat. Prod., 1981, volume 44, issue 6, pages 676–679, doi:10.1021/np50018a009

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Partial methylation of quercetin: Direct synthesis of tamarixetin, ombuin and ayanin. Koppaka V. Rao, Jacob A. Owoyale, Journal of Heterocyclic Chemistry, Volume 13 Issue 6, Pages 1293 - 1295

[2] Ombuin 3-sulphate from Flaveria chloraefolia. Denis Barron and Ragai K. Ibrahim, Phytochemistry, Volume 27, Issue 7, 1988, pages 2362-2363, doi:10.1016/0031-9422(88)80166-3

[3] Über die Synthese von Quercetin-3-glykosiden, II. Synthese des Ombuosids und eine rationelle Synthese von Rutin. Ludwig Hörhammer, Hildebert Wagner, Hans-Günther Arndt, Gustav Hitzler, Lorand Farkas, Chemische Berichte, Volume 101 Issue 4, Pp 1183-1185, 1968 (German)

[4] Flavonoids of Erythroxylum rufum and Erythroxylum ulei. Bruce A. Bohm, David W. Phillips and Fred R. Gander, J. Nat. Prod., 1981, volume 44, issue 6, pages 676–679, doi:10.1021/np50018a009