Biochanin A

Base Information

• Chemical Name: Biochanin A
• CAS No.: 491-80-5
• Molecular Formula: C16H12O5
• Molecular Weight: 284.268
• Hs Code.: 29329990
• European Community (EC) Number: 207-744-7
• NSC Number: 123538
• UNII: U13J6U390T
• DSSTox Substance ID: DTXSID1022394
• Nikkaji Number: J11.761G
• Wikipedia: Biochanin_A
• Wikidata: Q864222
• NCI Thesaurus Code: C28201
• Pharos Ligand ID: 2UV2SA96B8Q1
• Metabolomics Workbench ID: 22366
• ChEMBL ID: CHEMBL131921
• Mol file: 491-80-5.mol

Synonyms:biochanin A;biochanin A, 14C-labeled;genistein 4-methyl ether

Chemical Property of Biochanin A

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 2.25E-11mmHg at 25°C
• Melting Point: 210-213 °C(lit.)
• Refractive Index: 1.668
• Boiling Point: 518.6 °C at 760 mmHg
• PKA: 6.50±0.20(Predicted)
• Flash Point: 198.2 °C
• PSA: 79.90000
• Density: 1.42 g/cm³
• LogP: 2.87980
• Storage Temp.: 0-6°C
• Solubility.: acetone: 10 mg/mL, clear, brown
• Water Solubility.: Soluble in water (<1 mg/ml at 25°C), chloroform, methanol, DMSO (57 mg/ml at 25°C), and ethanol (9 mg/ml at 25°C).
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 284.06847348
• Heavy Atom Count: 21
• Complexity: 424

Purity/Quality:

20%, ^*data from raw suppliers

Biochanin A ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O
• 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 , 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).
• Uses: It has putative benefits in dietary cancer prophylaxis. It has also been found to inhibit fatty acid amide hydrolase and to act as agonist of PPARgamma, nuclear receptor that is current pharmacological target for the treatment of diabetes type 2. It acts as an antineoplastic agent. It is a selective agonist at ER-β estrogen receptors, and may have chemopreventive efficacy against breast cancer. In line with its low activity at ER-α estrogen receptors, it is essentially devoid of uterotrophic activity. Biochanin A is also a ligand for the aryl hydrocarbon receptor (AhR). It reduces arterial resistance and enhances microcirculation perhaps via effects on potassium and/or calcium ion channels. Induction of sulfotransferases for xenobiotic detoxification has been proposed as a mechanism of its cancer preventive effects. It is a nitric oxide synthase inhibitor and apoptosis inducer An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene

Technology Process of Biochanin A

There total 32 articles about Biochanin A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2,4,6-trihydroxy-4'-methoxydeoxybenzoin (15485-66-2) + methanesulfonyl chloride (124-63-0) → 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on (491-80-5)

Guidance literature:

In N,N-dimethyl-formamide; at 50 - 70 ℃; for 6h;

Reference yield: 92.0%

2,4,6-trihydroxy-4'-methoxydeoxybenzoin (15485-66-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on (491-80-5)

Guidance literature:

N,N-dimethyl-formamide; With phosphorus pentachloride; at 55 ℃; for 0.333333h;

2,4,6-trihydroxy-4'-methoxydeoxybenzoin; With boron trifluoride diethyl etherate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1080/00397910008087343

Reference yield: 90.0%

2,4,6-trihydroxy-4'-methoxydeoxybenzoin (15485-66-2) + orthoformic acid triethyl ester (122-51-0) → 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on (491-80-5)

Guidance literature:

With dmap; at 100 ℃; for 4h;

DOI:10.3184/030823408X382135

upstream raw materials:

2-carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone

acetic acid 7-acetoxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl ester

2,4,6-trihydroxy-4'-methoxydeoxybenzoin

formic acid ethyl ester

Downstream raw materials:

4',7-dimethoxy-5-hydroxyisoflavone

acetic acid 7-acetoxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl ester

5-hydroxy-3-(4-methoxy-phenyl)-7-(toluene-4-sulfonyloxy)-chromen-4-one

4',5,7-trimethoxyisoflavone

Refernces

• 1、 Do, Ji Min,Gee, Min Sung,Inn, Kyung-Soo,Kim, Jong-Ho,Kim, Nam Kwon,Kim, Nam-Jung,Lee, Hyun Woo,Lee, Jong Kil,Seo, Min-Duk,Seong, Ji Hye,Son, Seung Hwan,Yoo, Hyung-Seok,Yoo, Ji-Na. "Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation". . . Retrieved 2021/07/01.
• 2、 Tang, Qingyun,Vianney, Yoanes M.,Weisz, Klaus,Grathwol, Christoph W.,Link, Andreas,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.. "Influence of Substrate Binding Residues on the Substrate Scope and Regioselectivity of a Plant O-Methyltransferase against Flavonoids". . p. 3721 - 3727. Retrieved 2020/06/02.