Isovitexin

Isovitexin (or homovitexin, saponaretin) is a flavone. the apigenin-6-C-glucoside. In this case, the prefix 'iso' does not imply an isoflavonoid (the position of the B-ring on the C-ring), but the position of the glucoside on the flavone.

Isovitexin

Names
IUPAC name 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Other names homovitexin, saponaretin
Identifiers
CAS Number	38953-85-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18330
ChemSpider	142556
ECHA InfoCard	100.126.529
PubChem CID	162350
UNII	KTQ9R9MS0Q
CompTox Dashboard (EPA)	DTXSID60952152
InChI InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21+/m1/s1 Key: MYXNWGACZJSMBT-VJXVFPJBSA-N
SMILES C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O)C4C(C(C(C(O4)CO)O)O)O)O)O
Properties
Chemical formula	C21H20O10
Molar mass	432.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Natural occurrence

It can be found in the passion flower, Cannabis, and the açaí palm.[1]

Metabolism

• Isovitexin beta-glucosyltransferase

Glycosides

Saponarin is the isovitexin-7-O-glucoside.

See also

• Vitexin, the 8-C-glucoside of apigenin
• Isoorientin, the 3'-OH derivative

References

1. "Pharmacological studies of Passiflora sp. and their bioactive compounds"