CAS 491-80-5|biochanin|5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one|5,7-DIHYDROXY-4'-METHOXYISOFLAVONE|Biochanin A|4-Methylgenistein|Biochanin A|5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-...

General Information

Structure

Molecular Formula

C₁₆H₁₂O₅

Molecular Mass

284.26348

Exact Mass

284.06847348

Charge

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

Canonic Smiles

COc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O

Isomeric Smiles

c1(cc(c2c(c1)occ(c2=O)c1ccc(cc1)OC)O)O

Calculated Properties

JChem

Acid pKa

6.547949

H Acceptors

H Donor

LogD (pH = 5.5)

3.1857247

LogD (pH = 7.4)

2.2726228

Log P

3.2227664

Molar Refractivity

76.1652

Polarizability

29.012978

Polar Surface Area

75.99

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

biochanin 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

IUPAC name

5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

Synonyms

5,7-DIHYDROXY-4'-METHOXYISOFLAVONEBiochanin A4-MethylgenisteinBiochanin A5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one5,7-Dihydroxy-4’-methoxyisoflavonePratensolBiochanin AOlmelinGenistein 4'-methyl etherGenistein 4′-methyl ether5,7-Dihydroxy-4′-methoxyisoflavone5,7-Dihydroxy-4'-methoxyisoflavone5,7-二羟基-4'-甲氧基异黄酮

Names and Identifiers

Registration numbers

CAS Number

MDL Number

Beilstein Number

EC Number

PubChem CID

PubChem SID

Registration numbers

Properties

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Application(s)

Possesses sl. estrogenic activity

Biological Source

Constit. of clover (Trifolium repens), Dalbergia and Cotoneaster spp. Widely distributed in the Leguminosae (Papilionoideae), also in Cotoneaster pannosa and Cotoneaster serotina (Rosaceae), Virola caducifolia (Myricaceae) and others

Purity

98%

Safety Information

Storage Condition

-20°C

Room Temperature (15-30°C)

Refrigerator

MSDS Link

Download link

German water hazard class

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

是

Pharmacology Properties

Gene Information

human ... CYP19A1(1588)mouse ... Aldh1a2(19378), Maoa(17161)

Mechanism of Action

Estrogen

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S2377

Research Area: Cancer
Biological Activity:
Biochanin A(4-Methylgenistein) is an O-methylated isoflavone. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A is classified as a phytoestrogen and has putative benefits in dietary cancer prophylaxis. [1]

MP Biomedicals

02157745

(Biochanin A)

Sigma Aldrich

D2016

Biochem/physiol Actions
Biochanin A is an isoflavone phytoestrogen found in red clover (Trifolium pratense) that 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.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D2016.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

B387250

An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Biochanin_A

• Jing, Y. and Waxman, S.: Anticancer Res., 15(1992)

• Chae, Y.H., et al.: Chem. Biol. Interactions, 82, 181 (1992)

• 1147 (1995)

• Baker, W. et al., J.C.S., 1953, 1852, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 920A, (nmr)

• Murthy, M.S.R. et al., Magn. Reson. Chem., 1986, 24, 225, (cmr)

• Sekizaki, H. et al., Chem. Pharm. Bull., 1988, 36, 4876, (synth)

• Bass, R.J. et al., J.C.S. Perkin 1, 1978, 666, (cmr)

• Ashdown, D.H.J. et al., Synthesis, 1978, 843, (synth)

• Pelter, A. et al., Synthesis, 1976, 326, (synth)

• Aparecida dos Santos, S. et al., J. Braz. Chem. Soc., 1995, 6, 349, (pmr, cmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 95D, (ir)

• Ingham, J.L., Prog. Chem. Org. Nat. Prod., 1983, 43, 1, (rev, occur)

• Diedrich, D.F. et al., J. Chem. Eng. Data, 1977, 22, 448, (pmr)

• Elgamal, M.H.A. et al., J. Prakt. Chem., 1986, 328, 893, (ms)

• Balasubramanian, S. et al., Synth. Commun., 2000, 30, 469-484, (synth, pmr)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

biochanin 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

IUPAC name

5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

Synonyms

Registration numbers

CAS Number

MDL Number

Beilstein Number

EC Number

PubChem CID

PubChem SID

Molecule Details

S2377

(Biochanin A)

D2016

B387250

An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene.

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Biochanin_A

• Jing, Y. and Waxman, S.: Anticancer Res., 15(1992)

• Chae, Y.H., et al.: Chem. Biol. Interactions, 82, 181 (1992)

• 1147 (1995)

• Baker, W. et al., J.C.S., 1953, 1852, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 920A, (nmr)

• Murthy, M.S.R. et al., Magn. Reson. Chem., 1986, 24, 225, (cmr)

• Sekizaki, H. et al., Chem. Pharm. Bull., 1988, 36, 4876, (synth)

• Bass, R.J. et al., J.C.S. Perkin 1, 1978, 666, (cmr)

• Ashdown, D.H.J. et al., Synthesis, 1978, 843, (synth)

• Pelter, A. et al., Synthesis, 1976, 326, (synth)

• Aparecida dos Santos, S. et al., J. Braz. Chem. Soc., 1995, 6, 349, (pmr, cmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 95D, (ir)

• Ingham, J.L., Prog. Chem. Org. Nat. Prod., 1983, 43, 1, (rev, occur)

• Diedrich, D.F. et al., J. Chem. Eng. Data, 1977, 22, 448, (pmr)

• Elgamal, M.H.A. et al., J. Prakt. Chem., 1986, 328, 893, (ms)

• Balasubramanian, S. et al., Synth. Commun., 2000, 30, 469-484, (synth, pmr)

Bioactivity

PubChem BioAssay

Properties

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Application(s)

Possesses sl. estrogenic activity

Biological Source

Purity

98%

Safety Information

Storage Condition

-20°C

Room Temperature (15-30°C)

Refrigerator

MSDS Link

Download link

German water hazard class

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

是

Pharmacology Properties

Gene Information

human ... CYP19A1(1588)mouse ... Aldh1a2(19378), Maoa(17161)

Mechanism of Action

Estrogen

Molecule

ID:73001