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D7802

Sigma-Aldrich

Daidzein

≥98% (TLC), powder, carbonic anhydrase (CA) inhibitor

Synonym(s):

4′,7-Dihydroxy­iso­flavone, 7-Hydroxy-3-(4-hydroxy­phenyl)-4H-1-benzo­pyran-4-one, 7-Hydroxy-3-(4-hydroxy­phenyl)­chromone, Isoaurostatin

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About This Item

Empirical Formula (Hill Notation):
C15H10O4
CAS Number:
486-66-8
Molecular Weight:
254.24
Beilstein:
231523
EC Number:
207-635-4
MDL number:
MFCD00016954
UNSPSC Code:
12352202
PubChem Substance ID:
24278030
NACRES:
NA.77

product name

Daidzein, ≥98%, synthetic

biological source

synthetic

Quality Level

200

Assay

≥98%

form

powder

mp

>290 °C

solubility

DMSO: 10 mg/mL

storage temp.

−20°C

SMILES string

Oc1ccc(cc1)C2=COc3cc(O)ccc3C2=O

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

InChI key

ZQSIJRDFPHDXIC-UHFFFAOYSA-N

Gene Information

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

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General description

Daidzein is an isoflavone present in soy. It regulates oxidative stress, angiogenesis, cell growth and apoptosis. Daidzein has antioxidant, antiestrogenic and antiatherogenic properties. It provides protection against osteoporosis.

Application

Daidzein has been used:
  • as a control to evaluate fertility in rats
  • to study its effects on ovarian cancer
  • to simulate in vitro antioxidant activity

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.
Daidzein is a phytoestrogen that is suggested to play a role in preventing hormone-induced cancers. Arrests cell cycle at G1 in Swiss 3T3 cells.

Packaging

Packaged under Argon.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Conversion of daidzein and genistein by an anaerobic bacterium newly isolated from the mouse intestine
Matthies A, et al.
Applied and Environmental Microbiology, 74(15), 4847-4852 (2008)
Pharmacology E-Book: A Handbook for Complementary Healthcare Professionals (2008)
Epigenetic Cancer Therapy (2015)
K Higashi et al.
Biochimica et biophysica acta, 1221(1), 29-35 (1994-03-10)
An isoflavone compound, daidzein, inhibits the cell proliferation of Swiss 3T3 cells. Analysis of entry in S phase of Swiss 3T3 cells reveals that daidzein blocked cell cycle G1 phase progression 4.6 h after stimulation by bombesin plus insulin. After
Estrogen receptor modulators genistein, daidzein and ERB-041 inhibit cell migration, invasion, proliferation and sphere formation via modulation of FAK and PI3K/AKT signaling in ovarian cancer
Chan KKL, et al.
Cancer Cell International, 18(1), 65-65 (2018)
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