Biochanin A | CAS#491-80-5 | PPARα and PPARγ agonist

MedKoo Cat#: 540046 | Name: Biochanin A

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Biochanin A, also known as 4-methylGenistein, is a potential PPARα and PPARγ agonist found in Fabaceae plants such as clover, soy and alfalfa. It prevents replication of influenza virus, improves cognitive deficits, induces osteoblast differentiation, inhibits migration, invasion and proliferation of pancreatic cancer cells, and suppresses production of pro-inflammatory cytokines.

Chemical Structure

Biochanin A

CAS#491-80-5

Theoretical Analysis

MedKoo Cat#: 540046

Name: Biochanin A

CAS#: 491-80-5

Chemical Formula: C16H12O5

Exact Mass: 284.0685

Molecular Weight: 284.27

Elemental Analysis: C, 67.60; H, 4.26; O, 28.14

Price and Availability

Size	Price	Availability	Quantity
200mg	USD 250.00	2 Weeks
500mg	USD 550.00	2 Weeks

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Synonym

Biochanin; Pratensol; olmelin; 4’-methyl Genistein; 4-methylGenistein; 5,7-dihydroxy-4'-Methoxyisoflavone; NSC 123538

IUPAC/Chemical Name

5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

InChi Key

WUADCCWRTIWANL-UHFFFAOYSA-N

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

SMILES Code

O=C1C(C2=CC=C(OC)C=C2)=COC3=CC(O)=CC(O)=C13

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC50s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively.

In vitro activity:

Cell viability decreased in a concentration-dependent manner after treatment with BCA (biochanin A) by CCK8 assay (Figure 1A). In addition, the Edu assay was performed to determine the effect of BCA on glioma cell proliferation. BCA treatment significantly increased the percentage of Edu-positive cells compared with the control (Figure 1B). Taken together, these data indicated that BCA inhibited the growth of U251 in a concentration-dependent manner. Reference: Front Oncol. 2021; 11: 652008. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8298062/

In vivo activity:

The vital signs of rats in each group were stable. The treatment with BCA (biochanin A) effectively reduced Lee index and liver index (F = 104.781, P < 0.05); however, the weight was not effected in each group. Additionally, BCA effectively reduced the related lipid metabolism indexes of NAFLD, such as total cholesterol (TC), triglyceride (TG), low-density lipoprotein (LDL), blood glucose, insulin, IR (F =12.463 (TC), 6.909 [TG], and 15.3 effected 75 [LDL], P < 0.05), and increased HDL (F = 11.580, P < 0.05). This study observed that BCA could significantly improve steatosis and inflammatory cell infiltration in liver slices. Furthermore, BCA significantly increased the CYP7A1, LDLR, and PPAR-α protein expression in the liver and downregulated the HMGCR, SREBP-1c, and PPAR-γ protein expression. Reference: Diabetes Metab Syndr Obes. 2021; 14: 3161–3172. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8277457/

	Solvent	mg/mL	mM
Solubility
	DMSO	45.3	159.46
	DMSO:PBS (pH 7.2) (1:9)	0.1	0.35
	DMF	30.0	105.53
	Ethanol	8.5	29.90

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 284.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Dong Q, Li Q, Duan L, Yin H, Wang X, Liu Y, Wang B, Li K, Yao X, Yuan G, Pan Y. Biochanin A Inhibits Glioblastoma Growth via Restricting Glycolysis and Mitochondrial Oxidative Phosphorylation. Front Oncol. 2021 Jul 8;11:652008. doi: 10.3389/fonc.2021.652008. PMID: 34307130; PMCID: PMC8298062. 2. Wu Q, Shang Y, Shen T, Liu F, Zhang W. Biochanin A protects SH-SY5Y cells against isoflurane-induced neurotoxicity by suppressing oxidative stress and apoptosis. Neurotoxicology. 2021 Jun 30;86:10-18. doi: 10.1016/j.neuro.2021.06.007. Epub ahead of print. PMID: 34216683. 3. Guo MM, Qu SB, Lu HL, Wang WB, He ML, Su JL, Chen J, Wang Y. Biochanin A Alleviates Cerebral Ischemia/Reperfusion Injury by Suppressing Endoplasmic Reticulum Stress-Induced Apoptosis and p38MAPK Signaling Pathway In Vivo and In Vitro. Front Endocrinol (Lausanne). 2021 Jul 12;12:646720. doi: 10.3389/fendo.2021.646720. PMID: 34322090; PMCID: PMC8312488. 4. Fan Y, Yan LT, Yao Z, Xiong GY. Biochanin A Regulates Cholesterol Metabolism Further Delays the Progression of Nonalcoholic Fatty Liver Disease. Diabetes Metab Syndr Obes. 2021 Jul 9;14:3161-3172. doi: 10.2147/DMSO.S315471. PMID: 34276221; PMCID: PMC8277457.

In vitro protocol:

In vivo protocol:

1. Guo MM, Qu SB, Lu HL, Wang WB, He ML, Su JL, Chen J, Wang Y. Biochanin A Alleviates Cerebral Ischemia/Reperfusion Injury by Suppressing Endoplasmic Reticulum Stress-Induced Apoptosis and p38MAPK Signaling Pathway In Vivo and In Vitro. Front Endocrinol (Lausanne). 2021 Jul 12;12:646720. doi: 10.3389/fendo.2021.646720. PMID: 34322090; PMCID: PMC8312488. 2. Fan Y, Yan LT, Yao Z, Xiong GY. Biochanin A Regulates Cholesterol Metabolism Further Delays the Progression of Nonalcoholic Fatty Liver Disease. Diabetes Metab Syndr Obes. 2021 Jul 9;14:3161-3172. doi: 10.2147/DMSO.S315471. PMID: 34276221; PMCID: PMC8277457.

1: Jain A, Lai JC, Bhushan A. Biochanin A inhibits endothelial cell functions and proangiogenic pathways: implications in glioma therapy. Anticancer Drugs. 2015 Mar;26(3):323-30. doi: 10.1097/CAD.0000000000000189. PubMed PMID: 25501542. 2: Kaczmarczyk-Sedlak I, Zych M, Wojnar W, Ozimina-Kamińska E, Dudek S, Chadała N, Kachel A. BIOCHANIN A SHOWS NO EFFECT ON SKELETAL SYSTEM IN OVARIECTOMIZED RATS, WHEN ADMINISTERED IN MODERATE DOSE. Acta Pol Pharm. 2015 May-Jun;72(3):587-96. PubMed PMID: 26642667. 3: Wu WY, Wu YY, Huang H, He C, Li WZ, Wang HL, Chen HQ, Yin YY. Biochanin A attenuates LPS-induced pro-inflammatory responses and inhibits the activation of the MAPK pathway in BV2 microglial cells. Int J Mol Med. 2015 Feb;35(2):391-8. doi: 10.3892/ijmm.2014.2020. Epub 2014 Dec 2. PubMed PMID: 25483920. 4: Bhardwaj V, Tadinada SM, Jain A, Sehdev V, Daniels CK, Lai JC, Bhushan A. Biochanin A reduces pancreatic cancer survival and progression. Anticancer Drugs. 2014 Mar;25(3):296-302. doi: 10.1097/CAD.0000000000000044. PubMed PMID: 24201306. 5: Zhang Y, Chen WA. Biochanin A inhibits lipopolysaccharide-induced inflammatory cytokines and mediators production in BV2 microglia. Neurochem Res. 2015 Jan;40(1):165-71. doi: 10.1007/s11064-014-1480-2. Epub 2014 Nov 29. PubMed PMID: 25432463. 6: Hajrezaie M, Salehen N, Karimian H, Zahedifard M, Shams K, Al Batran R, Majid NA, Khalifa SA, Ali HM, El-Seedi H, Abdulla MA. Biochanin a gastroprotective effects in ethanol-induced gastric mucosal ulceration in rats. PLoS One. 2015 Mar 26;10(3):e0121529. doi: 10.1371/journal.pone.0121529. eCollection 2015. PubMed PMID: 25811625; PubMed Central PMCID: PMC4374864. 7: Wang W, Tang L, Li Y, Wang Y. Biochanin A protects against focal cerebral ischemia/reperfusion in rats via inhibition of p38-mediated inflammatory responses. J Neurol Sci. 2015 Jan 15;348(1-2):121-5. doi: 10.1016/j.jns.2014.11.018. Epub 2014 Nov 18. PubMed PMID: 25466482. 8: Hanski L, Genina N, Uvell H, Malinovskaja K, Gylfe Å, Laaksonen T, Kolakovic R, Mäkilä E, Salonen J, Hirvonen J, Elofsson M, Sandler N, Vuorela PM. Inhibitory activity of the isoflavone biochanin A on intracellular bacteria of genus Chlamydia and initial development of a buccal formulation. PLoS One. 2014 Dec 16;9(12):e115115. doi: 10.1371/journal.pone.0115115. eCollection 2014. PubMed PMID: 25514140; PubMed Central PMCID: PMC4267780. 9: Chen J, Ge B, Wang Y, Ye Y, Zeng S, Huang Z. Biochanin A promotes proliferation that involves a feedback loop of microRNA-375 and estrogen receptor alpha in breast cancer cells. Cell Physiol Biochem. 2015;35(2):639-46. doi: 10.1159/000369725. Epub 2015 Jan 28. PubMed PMID: 25613180. 10: Ming X, Ding M, Zhai B, Xiao L, Piao T, Liu M. Biochanin A inhibits lipopolysaccharide-induced inflammation in human umbilical vein endothelial cells. Life Sci. 2015 Sep 1;136:36-41. doi: 10.1016/j.lfs.2015.06.015. Epub 2015 Jul 2. PubMed PMID: 26141992. 11: Wu DQ, Zhong HM, Ding QH, Ba L. Protective effects of biochanin A on articular cartilage: in vitro and in vivo studies. BMC Complement Altern Med. 2014 Nov 15;14:444. doi: 10.1186/1472-6882-14-444. PubMed PMID: 25398247; PubMed Central PMCID: PMC4251671. 12: Chundi V, Challa SR, Garikapati DR, Juvva G, Jampani A, Pinnamaneni SH, Venigalla S. Biochanin-A attenuates neuropathic pain in diabetic rats. J Ayurveda Integr Med. 2016 Oct - Dec;7(4):231-237. doi: 10.1016/j.jaim.2016.08.001. Epub 2016 Nov 25. PubMed PMID: 27890700; PubMed Central PMCID: PMC5192256. 13: Liu X, Wang T, Liu X, Cai L, Qi J, Zhang P, Li Y. Biochanin A protects lipopolysaccharide/D-galactosamine-induced acute liver injury in mice by activating the Nrf2 pathway and inhibiting NLRP3 inflammasome activation. Int Immunopharmacol. 2016 Sep;38:324-31. doi: 10.1016/j.intimp.2016.06.009. Epub 2016 Jun 23. PubMed PMID: 27344638. 14: Tan JW, Kim MK. Neuroprotective Effects of Biochanin A against β-Amyloid-Induced Neurotoxicity in PC12 Cells via a Mitochondrial-Dependent Apoptosis Pathway. Molecules. 2016 Apr 25;21(5). pii: E548. doi: 10.3390/molecules21050548. PubMed PMID: 27120593. 15: Azizi R, Goodarzi MT, Salemi Z. Effect of biochanin a on serum visfatin level of streptozocin-induced diabetic rats. Iran Red Crescent Med J. 2014 Sep 5;16(9):e15424. doi: 10.5812/ircmj.15424. eCollection 2014 Sep. PubMed PMID: 25593725; PubMed Central PMCID: PMC4270635. 16: Wang J, He C, Wu WY, Chen F, Wu YY, Li WZ, Chen HQ, Yin YY. Biochanin A protects dopaminergic neurons against lipopolysaccharide-induced damage and oxidative stress in a rat model of Parkinson's disease. Pharmacol Biochem Behav. 2015 Nov;138:96-103. doi: 10.1016/j.pbb.2015.09.013. Epub 2015 Sep 21. PubMed PMID: 26394281. 17: Su SJ, Yeh YT, Su SH, Chang KL, Shyu HW, Chen KM, Yeh H. Biochanin a promotes osteogenic but inhibits adipogenic differentiation: evidence with primary adipose-derived stem cells. Evid Based Complement Alternat Med. 2013;2013:846039. doi: 10.1155/2013/846039. Epub 2013 Jun 16. PubMed PMID: 23843885; PubMed Central PMCID: PMC3697292. 18: Choi S, Jung WS, Cho NS, Ryu KH, Jun JY, Shin BC, Chung JH, Yeum CH. Mechanisms of phytoestrogen biochanin A-induced vasorelaxation in renovascular hypertensive rats. Kidney Res Clin Pract. 2014 Dec;33(4):181-6. doi: 10.1016/j.krcp.2014.08.003. Epub 2014 Nov 12. PubMed PMID: 26885474; PubMed Central PMCID: PMC4714256. 19: Lim TG, Kim JE, Jung SK, Li Y, Bode AM, Park JS, Yeom MH, Dong Z, Lee KW. MLK3 is a direct target of biochanin A, which plays a role in solar UV-induced COX-2 expression in human keratinocytes. Biochem Pharmacol. 2013 Oct 1;86(7):896-903. doi: 10.1016/j.bcp.2013.08.002. Epub 2013 Aug 12. PubMed PMID: 23948065; PubMed Central PMCID: PMC4241970. 20: Chrzanowska AM, Poliwoda A, Wieczorek PP. Characterization of particle morphology of biochanin A molecularly imprinted polymers and their properties as a potential sorbent for solid-phase extraction. Mater Sci Eng C Mater Biol Appl. 2015 Apr;49:793-8. doi: 10.1016/j.msec.2015.01.069. Epub 2015 Jan 23. PubMed PMID: 25687010.