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Ayanin

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Ayanin
Chemical structure of ayanin
Names
IUPAC name 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxychromen-4-one
Other names 3,7,4'-Tri-O-methylquercetin
3,7,4'-trimethylquercetin
5,3'-dihydroxy-3,7,4'-trimethoxyflavone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-13(23-2)11(19)6-9/h4-8,19-20H,1-3H3Key: KPCRYSMUMBNTCK-UHFFFAOYSA-N
  • Key: KPCRYSMUMBNTCK-UHFFFAOYAE
SMILES
  • COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)O
  • O=C1c3c(O/C(=C1/OC)c2ccc(OC)c(O)c2)cc(OC)cc3O
Properties
Chemical formula C18H16O7
Molar mass 344.31 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

Ayanin is a O-methylated flavonol, a type of flavonoid. It is the 3,7,4'-tri-O-methylation of quercetin.

It can be found in Croton schiedeanus. It can also be synthetized.

Biosynthetis

The enzyme 3,7-dimethylquercetin 4'-O-methyltransferase uses S-adenosyl methionine and 5,3',4'-trihydroxy-3,7-dimethoxyflavone (rhamnazin) to produce S-adenosylhomocysteine and 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (ayanin).

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
Flavonols and their conjugates
Backbone
Aglycones
Flavonols
Aglycones
Conjugates
Glycosides of herbacetin
Glycosides of kaempferol
Glycosides of myricetin
Conjugates of quercetin
Sulfates
Glycosides
O-Methylated flavonols
Aglycones
Glycosides
of isorhamnetin
other
Derivative flavonols
Aglycones
Glycosides
Pyranoflavonols
Aglycones
Furanoflavonols
Aglycones
Glycosides
Semisynthetic
Glycosides

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