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

• ChemBase ID: 72943
• Molecular Formular: C16H12O4
• Molecular Mass: 268.26408
• Monoisotopic Mass: 268.07355886
• SMILES: c12c(cc(cc1)O)occ(c2=O)c1ccc(cc1)OC
• Canonical SMILES: COc1ccc(cc1)c1coc2c(c1=O)ccc(c2)O
• InChI: InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
• InChIKey: HKQYGTCOTHHOMP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: formononetin; 7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• Synonyms: 7-HYDROXY-4'-METHOXYISOFLAVONE; 7-Hydroxy-3-(4-methoxyphenyl)chromone; 7-Hydroxy-4′-methoxyisoflavone; Formononetin; Biochanin B; Formononetol; Formononetin; 7-Hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one; 7-Hydroxy-4'-methoxy- isoflavone; 7-Hydroxy-3-(4-methoxyphenyl)chromen-4-one; Daidzein 4'-methyl ether; Flavosil; Formonentin; Formonetin; Myconate; NSC 93360; Formoononetin; Neochanin; Pratol; 7-Hydroxy-4'-methoxyisoflavone; 4'-O-methyldaidzein; 7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one; U - 2,2-Dichloropropane; 异亚丙基二氯; 2,2-二氯丙烷

Database IDs

• CAS Number: 40150-98-9; 485-72-3; 594-20-7
• EC Number: 207-623-9
• MDL Number: MFCD00016948
• Beilstein Number: 237979
• PubChem SID: 24871382; 162037863
• PubChem CID: 5280378
• CHEBI ID: 18088
• CHEMBL: 242341
• Chemspider ID: 4444070
• KEGG ID: C00858
• Wikipedia Title: Formononetin

CALCULATED PROPERTIES

• Acid pKa: 6.478253
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.8332336
• LogD (pH = 7.4): 1.929969
• Log P: 2.8763318
• Molar Refractivity: 74.1843 cm^3
• Polarizability: 28.38807 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Powder; White Solid
• Melting Point: 255-257°C; 257-261 °C

Safety Information

• Storage Condition: -20°C; Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; R
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Mechanism of Action: Estrogen

Product Information

• Purity: ≥99.0% (TLC); 96%; 98%
• Salt Data: Free Base
• Biological Source: Constit. of red and subterranean clovers ( Trifolium pratense and Trifolium subterraneum ) and of Chana ( Cicer arietinum ). Constit. of the heartwood of Pterocarpus indicus. Found also in Baptisia australis . Widely distributed in the Leguminosae (Papilionoideae). Also in Virola caducifolia and Virola multinervia (Myricaceae)
• Application(s): Shows estrogenic props.
• Empirical Formula (Hill Notation): C16H12O4

DETAILS

Selleck Chemicals - S2299

Research Area: Cardiovascular Disease
Biological Activity:
Formononetin(Formononetol) is a phytoestrogen from the root of Astragalus membranaceus and an O-methylated isoflavone. [1] It is found in a number of plants and herbs like the red clover. It is used as a blood enhancer and to improve blood microcirculation in complementary and alternative medicine. It promotes endothelial repair and wound healing in a process involving the over-expression of Egr-1 transcription factor through the regulation of the ERK1/2 and p38 MAPK pathways. [2]

Sigma Aldrich - 47752

Biochem/physiol Actions
Isoflavone found in red clover. Effective against Giardia lamblia infection, at least partially by inducing detachment of trophozoites from intestinal mucosa.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 47752.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 47752

Biochem/physiol Actions
Isoflavone found in red clover. Effective against Giardia lamblia infection, at least partially by inducing detachment of trophozoites from intestinal mucosa.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 47752.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - F693200

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.

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