Изовигтеон

Description

Isovigteone is a prenylated isoflavone, 3'-prenylgenistein. The molecule is built from the isoflavone core of genistein, to the B-ring of which a prenyl residue (3-methylbut-2-en-1-yl) is attached at the 3' position. In the product card, the Russian name is given with a machine translation error; the correct name of the substance is isovigteon, in English - Isowighteone (sometimes spelled Isowigtheone).

Identification

• CAS No: 68436-47-5
• Chemical formula: C20H18O5
• Molecular Weight: 338.35392
• Exact weight: 338.35
• Systematic name: 5,7-dihydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-4H-1-benzopyran-4-one
• Synonym by structure: 3'-dimethylallylgenistein
• Catalog section: flavonoids

Physico-chemical characteristics

• PSA (Polar Surface Area): 87
• XLogP3: 4.6
• Melting point: 171–172 °C

Natural source and biosynthesis

Prenylated isoflavones of this type are characteristic of legumes (Fabaceae) and mulberries (Moraceae). Isovigteon is described as one of the main prenylflavonoids of white lupine Lupinus albus. The route of its formation is established enzymatically: the isoflavonoid-specific lupine prenyltransferase transfers the prenyl residue on genistein strictly to the 3' position of the B-ring, giving isovigteon. Prenylation dramatically increases the lipophilicity of the molecule—calculated XLogP3 4.6 versus the significantly more polar genistein.

Scope of application

• analytical standard for HPLC and HPLC-MS for the analysis of legume isoflavonoids
• reference compound in works on plant prenyltransferases and the biosynthesis of prenylflavonoids
• research reagent in phytochemistry and biochemistry of secondary metabolism

Delivery form

The substance is supplied in small portions with a purity certificate. Due to lipophilicity, working solutions are prepared in DMSO or alcohol. Purpose is for research purposes, not for medical or food use.