Biochanin A

Alias:
Cat No.:V0909 Purity: ≥98%
Biochanin A (NSC-123538; Pratensol;NSC123538; olmelin; 4-Methylgenistein) is a novel,naturally occuring O-methylated isoflavone found inTrifolium pratense and Fabaceae plants such as clover, soy and alfalfa.
Biochanin A Chemical Structure CAS No.: 491-80-5
Product category: FAAH
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
1g
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Product Description

Biochanin A (NSC-123538; Pratensol; NSC123538; olmelin; 4-Methylgenistein) is a novel, naturally occuring O-methylated isoflavone found in Trifolium pratense and Fabaceae plants such as clover, soy and alfalfa. It exhibits antiproliferative and anti-inflammatory activities by inhibiting protein tyrosine kinase (PTK) such as EGFR/epidermal growth factor receptor with IC50 value of 91.5 μM. Biochanin A inhibits the hydrolysis of 0.5 μM anandamide by mouse, rat and human fatty acid amide hydrolase (FAAH) with IC50 values of 1.8, 1.4 and 2.4 μM respectively.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Biochanin A inhibits hydrolysis of 0.5 μM AEA by mouse, rat, and human FAAH with IC50 values of 1.8, 1.4, and 2.4 μM, respectively. Biochanin A inhibits FAAH at a pIC50 of 6.21±0.02 and an IC50 of 0.62 μM. Biochanin A inhibits URB597-sensitive tritium retention at high nanomolar to low micromolar concentrations. Experiments were conducted with human FAAH and 0.5 μM [3H]AEA, and the assay conditions improved utilization. Biochanin A, Genistein, Formononetin, and Daidzein inhibited activity in the low micromolar range with IC50 values of 6.0, 8.4, 12, and 30 μM, respectively [1].
ln Vivo
Test doses for biochanin A were 30, 100, and 300 μg. In a way that AM251 inhibited, the maximum dosage also decreased formalin-induced ERK phosphorylation. Therefore, upon topical application to the paw, Biochanin A exhibits behavior similar to URB597. Both URB597 (30 μg i.pl.) and Biochanin A (100 μg i.pl.) prevent the spinal cord phosphorylation of extracellular signal-regulated kinase, which is generated by injecting formalin into the plantar region of mice under anesthesia. AM251, a 30 μg i.pl. CB1 receptor antagonist/inverse agonist, considerably lessened the effects of both substances. While biochanin A (15 mg/k iv) does not raise brain AEA concentrations, it does slightly improve the tetrad test effects of 10 mg/kg iv AEA. While AEA (10 mg/kg iv) has little impact on its own, biochanin A (15 mg/kg iv) greatly increases its effect [1].
Animal Protocol
10 mg·kg-1 i.v. AEA.
Mice
References
[1]. Thors L, et al. Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase. Br J Pharmacol. 2010 Jun;160(3):549-60
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H12O5
Molecular Weight
284.26
CAS #
491-80-5
SMILES
O1C([H])=C(C2C([H])=C([H])C(=C([H])C=2[H])OC([H])([H])[H])C(C2=C(C([H])=C(C([H])=C12)O[H])O[H])=O
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
Chemical Name
5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Synonyms

Biochanin;NSC 123538;NSC-123538; Pratensol;NSC123538; olmelin; 4-methyl Genistein; 4-methylGenistein; 5,7-dihydroxy-4''-Methoxyisoflavone;

Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 57 mg/mL (200.5 mM)
Water:<1 mg/mL
Ethanol:9 mg/mL (31.7 mM)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.5179 mL 17.5895 mL 35.1791 mL
5 mM 0.7036 mL 3.5179 mL 7.0358 mL
10 mM 0.3518 mL 1.7590 mL 3.5179 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Biological Data
  • Biochanin A
    Inhibition by biochanin A of the hydrolysis of 16 nM [3H]oleoylethanolamide by membranes of COS7 cells transfected with either FAAH or FAAH-2. Br J Pharmacol. 2010 Jun;160(3):549-60.
  • Biochanin A

    The i.pl. administration of formalin to pentobarbital-anaesthetized mice produces phosphorylation of ERK ipsi-, but not contralaterally, and in a manner reduced by the FAAH inhibitor URB597 and by biochanin A. Br J Pharmacol. 2010 Jun;160(3):549-60.
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