Ayanin

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
CAS Number	572-32-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27825 ;
ChEMBL	ChEMBL74898 ;
ChemSpider	4444274 ;
PubChem CID	5280682;
UNII	YA465UF3LK ;
CompTox Dashboard (EPA)	DTXSID20205833 ;
	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,1-3H3 Key: KPCRYSMUMBNTCK-UHFFFAOYSA-N ;
	SMILES COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)O;
Properties
Chemical formula	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). Infobox references

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

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

Biosynthesis

The biosynthesis of ayanin in Chrysosplenium americanum is by the sequential methylation of the flavonol, quercetin. The first enzyme, quercetin 3-O-methyltransferase uses the cofactor, S-adenosyl methionine (SAM) to transfer a methyl group specifically at the 3-position:^[2]

3-O-methylquercetin

3-O-methylquercetin

7 methyl

3,7-dimethylquercetin

4' methyl

↑ 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.
1 2 De Luca V, Ibrahim RK (1985). "Enzymatic synthesis of polymethylated flavonols in Chrysosplenium americanum. I. Partial purification and some properties of S-adenosyl-L-methionine:flavonol 3-, 6-, 7-, and 4'-O-methyltransferases". Arch. Biochem. Biophys. 238 (2): 596–605. doi:10.1016/0003-9861(85)90205-X. PMID 3994393.