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Grundinformationen
- Standard-SMILES
COc1ccc(-c2coc3cc(O)cc(O)c3c2=O)cc1- InChIKey
WUADCCWRTIWANL-UHFFFAOYSA-N- Summenformel
- C16H12O5
- Durchschnittliche Molmasse
- 284,267 g/mol
- Monoisotopische Masse
- 284,06847348
Namen und Bezeichner
- Bevorzugter Name
- Biochanin A
- IUPAC
- 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
- Lokaler Name
- 5,7-Dihydroxy-3-p-methoxyphenyl-4H-chromen-4-on
- Englischer Name
- 5,7-Dihydrox -4'-methoxyisoflavone
- Summenformel
- C16H12O5
- Molmasse
- 284.26
Namen und Synonyme
Datenbank-Bezeichner
- CAS
491-80-5- PubChem CID
- 5280373
- DTXSID
DTXSID1022394- ChEMBL
CHEMBL131921- ChEBI
CHEBI:17574- UNII
- U13J6U390T
- EC Number
- 207-744-7
- Nikkaji
- J11.761G
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 210 · 210-213 °C(lit.)
- Siedepunkt
- 340 · 340-355 °C(Press: 0.5 Torr)
- Dichte
- 1.42 · 1.420±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 10 mg/mL, · acetone: 10 mg/mL, clear, brown
- Aggregatzustand
- Powder
- pka
- 6.5 · 6.50±0.20(Predicted)
- Farbe
- Off-White to Beige
- Wasserlöslichkeit
- 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).
- BRN
- 278107 · 278107
- Major Application
- food and beverages
- Kosmetik-Inhaltsstoffe Funktionen
- HUMECTANTSKIN PROTECTINGSKIN CONDITIONING
- InChI
- 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
- InChIKey
- WUADCCWRTIWANL-UHFFFAOYSA-N
- SMILES
- C1OC2=CC(O)=CC(O)=C2C(=O)C=1C1=CC=C(OC)C=C1
- LogP
- 3.341 · 3.341 (est)
- CAS Datenbank
- 491 · 491-80-5(CAS DataBase Reference)
- EPA chemische Informationen
- 4 H-1-Benzopyran-4-one, · 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)- (491-80-5)
Sicherheit und Regulatorisches
Sicherheitsdaten
- F
- 10
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29329990
- RTECS-Nr.
- DJ3002500
- safety_code
- 22-24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
BeschreibungBiochanin 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).
VerwendenAn isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene
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