A phytoestrogen
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Isomer(s)
35229Genkwanin 29432Prunetin
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Biochanin A

Item No. 16476

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,7-dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
CAS Number
491-80-5
Synonyms
  • 4’-methyl Genistein
  • 5,7-dihydroxy-4'-Methoxyisoflavone
  • NSC 123538
Molecular Formula
C16H12O5
Formula Weight
284.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2)(1:9): 0.1 mg/mlEthanol: 1 mg/ml
λmax
262 nm
SMILES
O=C1C2=C(O)C=C(O)C=C2OC=C1C3=CC=C(OC)C=C3
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product 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.1,2 Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein (Item No. 10005167), another phytoestrogen with diverse effects.3 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.4 Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis.5 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).6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Evans, B.A., Griffiths, K., and Morton, M.S. Inhibition of 5α-reductase in genital skin fibroblasts and prostate tissue by dietary lignans and isoflavonoids. J. Endocrinol. 147(2), 295-302 (1995).

    2. Khan, S.I., Zhao, J., Khan, I.A., et al. Potential utility of natural products as regulators of breast cancer-associated aromatase promoters. Reprod. Biol. Endocrinol. 9:91, (2011).

    3. Patisaul, H.B., and Jefferson, W. The pros and cons of phytoestrogens. Front. Neuroendocrinol. 31(4), 400-419 (2010).

    4. Wang, L., Waltenberger, B., Pferschy-Wenzig, E.M., et al. Natural product agonists of peroxisome proliferator-activated receptor gamma (PPARγ): A review. Biochem. Pharmacol. 92(1), 73-89 (2014).

    5. Rasbach, K.A., and Schnellmann, R.G. Isoflavones promote mitochondrial biogenesis. J. Pharmacol. Exp. Ther. 325(2), 536-543 (2008).

    6. Thors, L., Burston, J.J., Alter, B.J., et al. Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase. Br. J. Pharmacol. 160(3), 549-560 (2010).

    7. Medjakovic, S., and Jungbauer, A. Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor. J. Steroid Biochem. Mol. Biol. 108(1-2), 171-177 (2008).