CAS 486-66-8|daidzein|7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one|7-Hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one|Isoaurostatin|4',7-Dihydroxyisoflavone|Daidzeol|Daidzein|Daidzein|4',7-Dihydroxyis...

General Information

Structure

Molecular Formula

C₁₅H₁₀O₄

Molecular Mass

254.2375

Exact Mass

254.0579088

Charge

InChI

InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H

InChIKey

ZQSIJRDFPHDXIC-UHFFFAOYSA-N

Canonic Smiles

Oc1ccc(cc1)c1coc2c(c1=O)ccc(c2)O

Isomeric Smiles

c1(c(=O)c2c(oc1)cc(cc2)O)c1ccc(cc1)O

Calculated Properties

JChem

Acid pKa

6.47684

H Acceptors

H Donor

LogD (pH = 5.5)

2.6871917

LogD (pH = 7.4)

1.7724496

Log P

2.7304378

Molar Refractivity

69.702

Polarizability

26.477903

Polar Surface Area

66.76

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

daidzein 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

IUPAC name

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

Synonyms

7-Hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-oneIsoaurostatin4',7-DihydroxyisoflavoneDaidzeolDaidzeinDaidzein4',7-Dihydroxyisoflavone7-Hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one4',7-二羟基-异磺酮4',7-DihydroxyisoflavoneDaizeolDaidzeinDimethylbiochanin B7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one4′,7-Dihydroxy-iso-flavone7-Hydroxy-3-(4-hydroxy-phenyl)-chromone7-Hydroxy-3-(4-hydroxy-phenyl)-4H-1-benzo-pyran-4-one

Names and Identifiers

Registration numbers

Beilstein Number

CAS Number

MDL Number

EC Number

PubChem SID

Merck Index

CHEBI ID

KEGG ID

PubChem CID

Chemspider ID

CHEMBL

Wikipedia Title

Unique Ingredient Identifier

6287WC5J2L

Registration numbers

Properties

Pharmacology Properties

human ... ESR1(2099), ESR2(2100), UGT1A4(54657)mouse ... Aldh1a2(19378), Hexa(15211), Maoa(17161)rat ... Aldh1a2(116676)

Antioxydant

Counteract damaging effects of free radicals in tissues, regulates cell division and cell survival

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S1849

Research Area: Cardiovascular Disease
Biological Activity:
Daidzein belongs to the group of isoflavones. Daidzein and other isoflavone compounds, such as genistein, are present in a number of plants and herbs. Soy isoflavones are a group of compounds found in and isolated from the soybean. Besides functioning as antioxidants, many isoflavones have been shown to interact with animal and human estrogen receptors, and therefore are known as phytoestrogens. Soy isoflavones also produce non-hormonal effects. [1]

MP Biomedicals

02158812

Purity: >98% A negative control for MP Genistein¹ (tyrosine kinase inhibitor, Cat. No. 152355).

Wikipedia

Daidzein

Sigma Aldrich

D176

Biochem/physiol Actions
Soy isoflavone daidzein protects against oxidative damage in liver cells induced by 7,12-dimethylbenz[a]anthracene (DMBA). Catalase and superoxide dismutase activity, down-regulated by DMBA, was restored by daidzein.1

D7802

Biochem/physiol Actions
Daidzein is a phytoestrogen that is suggested to play a role in preventing hormone-induced cancers.2 Arrests cell cycle at G1 in Swiss 3T3 cells.3
Soy isoflavone daidzein protects against oxidative damage in liver cells induced by 7,12-dimethylbenz[a]anthracene (DMBA). Catalase and superoxide dismutase activity, down-regulated by DMBA, was restored by daidzein.1
Packaging
Packaged under Argon.

16587

30405

TRC

D103500

Inactive analog of Genistein (Cat. #G350000). Blocks the G1 phase of the cell cycle in Swiss 3T3 cells by inhibiting casein kinase II activity1.Daidzein has also been shown to inhibit the action of GABA on recombinant GABAA receptors2.uv max:250 nm (log

Molecule Details

References

PubChem Literature

From Data Sources

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

• Akiyama, T., et al., J. Biol. Chem. , 262 : 5592 (1987).

• Am. J. Respir. Cell Mol. Biol., 7, 637 (1992)

• Biochim. Biophys. Acta 1221, 29 (1992)

• Huang, R.Q.; Fang, M.J.; Dillon, G.H., Mol. Brain Res. 67: 177-183 (1999)

• Deshpande, V.H. et al., Indian J. Chem., Sect. B, 1977, 15, 201, (isol)

• Jha, H.C. et al., Can. J. Chem., 1980, 58, 1211, (cmr)

• Inone, T. et al., Chem. Pharm. Bull., 1974, 22, 1422, (biosynth)

• Breytenbach, J.C., J. Nat. Prod., 1986, 49, 1003, (isol, deriv)

• Ayabe, S. et al., J.C.S. Perkin 1, 1982, 2725, (biosynth, ms)

• Jain, A.C. et al., J.C.S. Perkin 1, 1986, 215, (synth)

• Matsuda, Y. et al., Agric. Biol. Chem., 1988, 52, 3211, (isol, props)

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

• Farkas, L. et al., Chem. Ber., 1959, 92, 819, (synth)

• Kobayashi, M. et al., Phytochemistry, 1983, 22, 1257, (isol)

• Hirakura, K. et al., Phytochemistry, 1997, 46,

• Carman, R.M. et al., Aust. J. Chem., 1985, 38, 485, (isol)

• Gupta, S.R. et al., Phytochemistry, 1971, 10, 877, (synth)

• Hendrich, S. et al., Handbook of Nutraceuticals and Functional Foods, (ed. Wildman, R.E.C.), CRC Press,, 2001, 55-75, (occur, metab)

• Markham, K.R. et al., Phytochemistry, 1968, 7, 791, (isol)

• Dement, W.A., Phytochemistry, 1972, 11, 1089, (isol)

• Aoyagi, T. et al., J. Antibiot., 1975, 28, 1006; 1979, 32, 217, (rhamnosides)

• Ann. Chim. Farm.

• Nakayama, M. et al., Bull. Chem. Soc. Jpn., 1978, 51, 2398, (synth)

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

• Nishiyama, K. et al., Biosci., Biotechnol., Biochem., 1993, 57, 107, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

daidzein 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

IUPAC name

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

Synonyms

Registration numbers

Beilstein Number

CAS Number

MDL Number

EC Number

PubChem SID

Merck Index

CHEBI ID

KEGG ID

PubChem CID

Chemspider ID

CHEMBL

Wikipedia Title

Unique Ingredient Identifier

Molecule Details

S1849

Purity: >98% A negative control for MP Genistein¹ (tyrosine kinase inhibitor, Cat. No. 152355).

Wikipedia

Daidzein

Sigma Aldrich

D176

D7802

16587

30405

TRC

D103500

References

PubChem Literature

From Data Sources

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

• Akiyama, T., et al., J. Biol. Chem. , 262 : 5592 (1987).

• Am. J. Respir. Cell Mol. Biol., 7, 637 (1992)

• Biochim. Biophys. Acta 1221, 29 (1992)

• Huang, R.Q.; Fang, M.J.; Dillon, G.H., Mol. Brain Res. 67: 177-183 (1999)

• Deshpande, V.H. et al., Indian J. Chem., Sect. B, 1977, 15, 201, (isol)

• Jha, H.C. et al., Can. J. Chem., 1980, 58, 1211, (cmr)

• Inone, T. et al., Chem. Pharm. Bull., 1974, 22, 1422, (biosynth)

• Breytenbach, J.C., J. Nat. Prod., 1986, 49, 1003, (isol, deriv)

• Ayabe, S. et al., J.C.S. Perkin 1, 1982, 2725, (biosynth, ms)

• Jain, A.C. et al., J.C.S. Perkin 1, 1986, 215, (synth)

• Matsuda, Y. et al., Agric. Biol. Chem., 1988, 52, 3211, (isol, props)

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

• Farkas, L. et al., Chem. Ber., 1959, 92, 819, (synth)

• Kobayashi, M. et al., Phytochemistry, 1983, 22, 1257, (isol)

• Hirakura, K. et al., Phytochemistry, 1997, 46,

• Carman, R.M. et al., Aust. J. Chem., 1985, 38, 485, (isol)

• Gupta, S.R. et al., Phytochemistry, 1971, 10, 877, (synth)

• Hendrich, S. et al., Handbook of Nutraceuticals and Functional Foods, (ed. Wildman, R.E.C.), CRC Press,, 2001, 55-75, (occur, metab)

• Markham, K.R. et al., Phytochemistry, 1968, 7, 791, (isol)

• Dement, W.A., Phytochemistry, 1972, 11, 1089, (isol)

• Aoyagi, T. et al., J. Antibiot., 1975, 28, 1006; 1979, 32, 217, (rhamnosides)

• Ann. Chim. Farm.

• Nakayama, M. et al., Bull. Chem. Soc. Jpn., 1978, 51, 2398, (synth)

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

• Nishiyama, K. et al., Biosci., Biotechnol., Biochem., 1993, 57, 107, (synth)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

human ... ESR1(2099), ESR2(2100), UGT1A4(54657)mouse ... Aldh1a2(19378), Hexa(15211), Maoa(17161)rat ... Aldh1a2(116676)

Antioxydant

Counteract damaging effects of free radicals in tissues, regulates cell division and cell survival

Molecule

ID:60045