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Biochanin A (CAS 491-80-5)

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Alternate Names:
5,7-Dihydroxy-4′-methoxyisoflavone; 4′-Methylgenistein
Application:
Biochanin A is a nitric oxide synthase inhibitor and apoptosis inducer
CAS Number:
491-80-5
Purity:
≥98%
Molecular Weight:
284.27
Molecular Formula:
C16H12O5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Biochanin A, an isoflavone, is a natural plant phytoestrogen which has been reported to be an antiproliferative and anti-inflammatory agent. Studies show that this compound inhibits iNOS expression and lipopolysacharide (LPS)-induced nitric oxide production in macrophages. Additionally, Biochanin A displays the ability to block phosphorylation of IkappaBalpha and p38 MAPK, which prevents NF-kappaB activation. Furthermore, Biochanin A has been observed to suppress IL-6, IL-1beta, and TNF-alpha production.


Biochanin A (CAS 491-80-5) References

  1. The mitochondrial monoamine oxidase-aldehyde dehydrogenase pathway: a potential site of action of daidzin.  |  Rooke, N., et al. 2000. J Med Chem. 43: 4169-79. PMID: 11063613
  2. Antigiardial activity of isoflavones from Dalbergia frutescens bark.  |  Khan, IA., et al. 2000. J Nat Prod. 63: 1414-6. PMID: 11076565
  3. Effects of synthetic and naturally occurring flavonoids on metabolic activation of benzo[a]pyrene in hamster embryo cell cultures.  |  Chae, YH., et al. 1992. Chem Biol Interact. 82: 181-93. PMID: 1568269
  4. Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities.  |  Salem, MM. and Werbovetz, KA. 2006. J Nat Prod. 69: 43-9. PMID: 16441066
  5. Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.  |  Tasdemir, D., et al. 2006. J Med Chem. 49: 3345-53. PMID: 16722653
  6. Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.  |  Schuster, D., et al. 2008. J Med Chem. 51: 4188-99. PMID: 18533708
  7. Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase.  |  Thors, L., et al. 2010. Br J Pharmacol. 160: 549-60. PMID: 20590565
  8. Biochanin-A, an isoflavon, showed anti-proliferative and anti-inflammatory activities through the inhibition of iNOS expression, p38-MAPK and ATF-2 phosphorylation and blocking NFκB nuclear translocation.  |  Kole, L., et al. 2011. Eur J Pharmacol. 653: 8-15. PMID: 21147093
  9. Biochanin A attenuates myocardial ischemia/reperfusion injury through the TLR4/NF-κB/NLRP3 signaling pathway.  |  Bai, Y., et al. 2019. Acta Cir Bras. 34: e201901104. PMID: 31859817
  10. Biochanin A: A novel bioactive multifunctional compound from nature.  |  Sarfraz, A., et al. 2020. Sci Total Environ. 722: 137907. PMID: 32208265
  11. Biochanin A Alleviates Cerebral Ischemia/Reperfusion Injury by Suppressing Endoplasmic Reticulum Stress-Induced Apoptosis and p38MAPK Signaling Pathway In Vivo and In Vitro.  |  Guo, MM., et al. 2021. Front Endocrinol (Lausanne). 12: 646720. PMID: 34322090
  12. Biochanin A alleviates cognitive impairment and hippocampal mitochondrial damage in ovariectomized APP/PS1 mice.  |  Hou, Y., et al. 2022. Phytomedicine. 100: 154056. PMID: 35338989
  13. Biochanin A as a modulator of the inflammatory response: An updated overview and therapeutic potential.  |  Felix, FB., et al. 2022. Pharmacol Res. 180: 106246. PMID: 35562014
  14. Structural requirements for differentiation-induction and growth-inhibition of mouse erythroleukemia cells by isoflavones.  |  Jing, Y. and Waxman, S. 1995. Anticancer Res. 15: 1147-52. PMID: 7653993

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Biochanin A, 100 mg

sc-205603
100 mg
$75.00

Biochanin A, 250 mg

sc-205603A
250 mg
$129.00

Can you provide the references for the IC50 data listed for Biochanin A?

Asked by: ChemSynth123
Thank you for your question. Here are some citations for Biochanin A, sc-205603, IC50 data: http://europepmc.org/abstract/MED/11076565 12/21/2016: IC50 values were pulled from https://www.ebi.ac.uk/chembl/bioactivity/results/1/cmpd_chemblid/asc/tab/display. J. Med. Chem. (2000) 43:4169-4179 - https://www.ebi.ac.uk/chembl/doc/inspect/CHEMBL1133504 J. Med. Chem. (2008) 51:4188-4199 - https://www.ebi.ac.uk/chembl/doc/inspect/CHEMBL1157467 J. Nat. Prod. (2006) 69:43-49 - https://www.ebi.ac.uk/chembl/doc/inspect/CHEMBL1157220 J. Nat. Prod. (2000) 63:1414-1416 - https://www.ebi.ac.uk/chembl/doc/inspect/CHEMBL1155607 J. Med. Chem. (2006) 49:3345-3353 - https://www.ebi.ac.uk/chembl/doc/inspect/CHEMBL1148505
Answered by: TechService7
Date published: 2023-10-29
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Rated 5 out of 5 by from WangWang, J. et al. (PubMed 26394281) reported that Biochanin A protects dopaminergic neurons against lipopolysaccharide-induced damage and oxidative stress in a rat model of Parkinson's disease. -SCBT Publication Review
Date published: 2015-03-26
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Biochanin A is rated 5.0 out of 5 by 1.
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