Ayanin

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

Ayanin
Chemical structure of ayanin
Names
IUPAC name
3′,5-Dihydroxy-3,4′,7-trimethoxyflavone
Systematic IUPAC name
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxy-4H-1-benzopyran-4-one
Other names
  • 3,7,4'-Tri-O-methylquercetin
  • 3,7,4'-Trimethylquercetin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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 checkY
    Key: KPCRYSMUMBNTCK-UHFFFAOYSA-N checkY
  • 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 344.319 g·mol−1
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).
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Infobox references

It can be found in Croton schiedeanus. It can also be synthesized.[1]

Biosynthesis

The enzyme 3,7-dimethylquercetin 4'-O-methyltransferase uses S-adenosyl methionine and rhamnazin to produce S-adenosylhomocysteine and ayanin.

References
  1. Rao, Koppaka V.; Owoyale, Jacob A. (1976). "Partial methylation of quercetin: Direct synthesis of tamarixetin, ombuin and ayanin". Journal of Heterocyclic Chemistry. 13 (6): 1293–1295. doi:10.1002/jhet.5570130629.


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