Biochanin A

Datasheet MSDS
Catalog Number
ANC01985
Product Name
Biochanin A
Structure
Biochanin A
CAS Number
491-80-5
IUPAC Name
5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
Synonyms
Biochanin; Pratensol; olmelin; 4'-methylGenistein; 4-methylGenistein; 5,7-dihydroxy-4'-Methoxyisoflavone; NSC123538; NSC-123538; NSC123538
Molecular Formula
C16H12O5
Molecular Weight
284.26
Appearance
Powder
Purity
>98%
Description
Biochanin A is a natural isoflavone with diverse biological actions, most notably as a phytoestrogen. It can affect hormone levels by inhibiting 5α-reductase and 17β-hydroxysteroid dehydrogenase or altering aromatase (CYP19A1) activity. Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein (Item No. 10005167), another phytoestrogen with diverse effects. Biochanin A also intersects with signaling through peroxisome proliferator-activated receptors (PPARs), as it activates PPARγ (EC50 = 19 μM) and has also been shown to activate a PPARα promoter. Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis. Biochanin A also inhibits fatty acid amide hydrolase (IC50 = 2.4 μM) and acts as an agonist of the aryl hydrocarbon receptor (EC50 = 0.25 μM).
SMILES
COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O
InChI
InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3
InChI Key
WUADCCWRTIWANL-UHFFFAOYSA-N
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