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^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:67493
ChemSpider	4478412
PubChem	5320287
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).
Y verify (what is ^YN ?)
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

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates	Quercetin 3-O-sulfate Quercetin 3,3'-bissulfate Quercetin 3,4'-bissulfate

Glycosides	Avicularin (quercetin-3-O-α-L-arabinofuranoside) CTN-986 Guaijaverin (quercetin 3-O-arabinoside) Heliosin (quercetin 3-digalactoside) Hyperoside (quercetin 3-O-galactoside) Isoquercetin (quercetin 3-O-glucoside) Miquelianin (quercetin 3-O-glucuronide) Quercetin 3,4'-diglucoside Quercetin-3-sophorodide Quercitrin (quercetin 3-O-rhamnoside) Rutin (quercetin rutinoside) Reinutrin (quercetin-3-D-xyloside) Spiraeoside (quercetin 4'-O-glucoside) Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside

other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)

Derivative flavonols

Aglycones	Noricaritin Dihydronoricaritin

Glycosides	Amurensin Icariin Phelloside Dihydrophelloside Rutin S

Pyranoflavonols

Aglycones	Karanjachromene

Furanoflavonols

Aglycones	Karanjin

Glycosides	Pongamoside A, B and C

Semisynthetic

Glycosides	Hydroxyethylrutosides Monoxerutin Troxerutin

This article is issued from Wikipedia - version of the 11/2/2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.