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
572-32-7 YesY=
ChEBI CHEBI:27825 YesY
ChEMBL ChEMBL74898 YesY
ChemSpider 4444274 YesY
Jmol 3D model Interactive image
Interactive image
PubChem 5280682
  • 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,1-3H3 YesY
    Key: KPCRYSMUMBNTCK-UHFFFAOYSA-N YesY
  • InChI=1/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,1-3H3
    Key: KPCRYSMUMBNTCK-UHFFFAOYAE
  • 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
C18H16O7
Molar mass 344.31 g/mol
Density 1.454 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Ayanin is an 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.[1]

Biosynthesis

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

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  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