Formononetin

Base Information

• Chemical Name: Formononetin
• CAS No.: 485-72-3
• Molecular Formula: C16H12O4
• Molecular Weight: 268.269
• Hs Code.: 29329990
• European Community (EC) Number: 207-623-9
• NSC Number: 93360
• UNII: 295DQC67BJ
• DSSTox Substance ID: DTXSID4022311
• Nikkaji Number: J12.525C
• Wikipedia: Formononetin
• Wikidata: Q408859
• NCI Thesaurus Code: C68469
• Metabolomics Workbench ID: 22175
• ChEMBL ID: CHEMBL242341
• Mol file: 485-72-3.mol

Synonyms:Biochanin B;4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-methoxyphenyl)- (9CI);4H-1-Benzopyran-4-one, 7-hydroxy-3- (4-methoxyphenyl)-;7-hydroxy-3-(4-methoxyphenyl)chromen-4-one;7-Hydroxy-3-(4-methoxyphenyl)-4-benzopyrone;Formononetol;Isoflavone, 7-hydroxy-4-methoxy-;7-Hydroxy-4-methoxyisoflavone;4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-methoxyphenyl)-;Isoflavone, 7-hydroxy-4-methoxy- (8CI);4H-1-Benzopyran-4-one,7-hydroxy-3-(4- methoxyphenyl)-;Red Clover Extract;7-Hydroxy-4'-Methoxyisoflavone;7-Hydroxy-4-Methoxy Isoflavone;

Chemical Property of Formononetin

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 8.17E-10mmHg at 25°C
• Melting Point: 256-260 °C
• Refractive Index: 1.641
• Boiling Point: 479.4 °C at 760 mmHg
• PKA: 6.99±0.20(Predicted)
• Flash Point: 183.4 °C
• PSA: 59.67000
• Density: 1.329 g/cm³
• LogP: 3.17420
• Storage Temp.: Refrigerator
• Solubility.: Soluble in DMSO (up to 100 mg/ml).
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 268.07355886
• Heavy Atom Count: 20
• Complexity: 395

Purity/Quality:

99% ^*data from raw suppliers

Formononetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)O
• Description: Formononetin (485-72-3) is a naturally occurring isoflavone isolated from Astragalus and other plants. Increases adipocyte thermogenesis by modulating PPARγ activity.1?Activates AMP-activated protein kinase/β-catenin signaling to inhibit adipogenesis.2?Accelerates wound repair by increasing expression of Egr-1 transcription factor.3?Potential cancer chemopreventive and chemotherapeutic.4?Provides neuroprotection against traumatic brain injury by inhibition of neuroinflammation in a rat model.5
• Uses: An isoflavone found in a variety of plants. When metabolized in the rumen this compound transforms into a potent estrogen. Formononetin is an isoflavone found as one of the main plant estrogens in animal feed. When metabolized in the rumen this compound transforms into a potent estrogen. phytoestrogen Formononetin is an isoflavonoid phytoestrogenic compound found in soy-based foods and is the precursor of daidzein . It acts as an agonist of the aryl hydrocarbon receptor with an EC50 value of 0.13 μM. Formononetin has been reported to possess antitumor and antiviral activity.

Technology Process of Formononetin

There total 61 articles about Formononetin 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: 96.0%

1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone (487-49-0) → 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on (485-72-3)

Guidance literature:

With methanesulfonyl chloride; In N,N-dimethyl-formamide; at 60 - 70 ℃; for 1.5h;

Reference yield: 94.0%

7-benzyloxy-3-(4-methoxyphenyl)-1-benzopyran-4-one (1621-59-6) → 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on (485-72-3)

Guidance literature:

With palladium hydroxide - carbon; cyclohexene; In ethanol; for 1h; Reflux;

DOI:10.1016/j.tetlet.2009.02.159

Reference yield: 90.0%

1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone (487-49-0) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on (485-72-3) + 5-hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one (133086-79-0)

Guidance literature:

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

1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone; With boron trifluoride diethyl etherate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1080/00397910008087343

upstream raw materials:

7-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-chromene-2-carboxylic acid

1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone

orthoformic acid triethyl ester

ononin

Downstream raw materials:

7-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-1-benzopyran-8-carboxaldehyde

3-(4-methoxyphenyl)-4-oxo-4H-chromene-7-yl acetate

7-ethoxy-3-(4-methoxyphenyl)-4H-chromen-4-one

7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one

Refernces

• 1、 Akashi, Tomoyoshi,Sawada, Yuji,Aoki, Toshio,Ayabe, Shin-Ichi. "New scheme of the biosynthesis of formononetin involving 2,7,4′-trihydroxyisoflavanone but not daidzein as the methyl acceptor". . p. 2276 - 2279. Retrieved 2000.
• 2、 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.
• 3、 Qiu, Rongmao,Luo, Guoshun,Cai, Xuerong,Liu, Linyi,Chen, Mingqi,Chen, Deying,You, Qidong,Xiang, Hua. "Structure-guided design and synthesis of isoflavone analogs of GW4064 with potent lipid accumulation inhibitory activities". . p. 3726 - 3730. Retrieved 2018/10/20.