Ombuin

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Ombuin
Chemical structure of ombuin Ombuin.svg
Chemical structure of ombuin
Names
IUPAC name
3,3′,5-Trihydroxy-4′,7-dimethoxyflavone
Systematic IUPAC name
3,5-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
Other names
4′,7-Dimethylquercetin
7,4′-Di-O-methylquercetin
4′,7-Dimethoxy-3,3′,5-trihydroxyflavone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • 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 X mark.svgN
    Key: BWORNNDZQGOKBY-UHFFFAOYSA-N X mark.svgN
  • 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
  • COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)O)O
Properties
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).
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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 synthesized. [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) :

References

  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 [ dead link ]
  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
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