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Merck

D7802

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
NACRES:
NA.77
PubChem Substance ID:
24278030
UNSPSC Code:
12352202
EC Number:
207-635-4
MDL number:
MFCD00016954
Beilstein/REAXYS Number:
231523

Key Documents

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Product Name

Daidzein, ≥98%, synthetic

InChI key

ZQSIJRDFPHDXIC-UHFFFAOYSA-N

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

SMILES string

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

biological source

synthetic

assay

≥98%

form

powder

mp

>290 °C

solubility

DMSO: 10 mg/mL

storage temp.

−20°C

Quality Level

200

Gene Information

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

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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

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.
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.

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.

Packaging

Packaged under Argon.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
128M4149V
13180326
018M4151V
077M4015V
13171008

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N Sathyamoorthy et al.
Cancer research, 54(4), 957-961 (1994-02-15)
Epidemiological studies suggest a lowered risk of hormone-dependent cancers among vegetarians, but the basis for this association remains unclear. Vegetables and fruits contain certain compounds which can be converted to biologically active hormone-like substances, such as lignans and isoflavones, by
Comparison of the effects of mesquite pod and Leucaena extracts with phytoestrogens on the reproductive physiology and sexual behavior in the male rat
Retana-Marquez S, et al.
Physiology & Behavior, 164, 1-10 (2016)
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)
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
Mesquite (Prosopis juliflora) pod extract decreases fertility in female but not male rats
Retana-Marquez S, et al.
African Journal of Pharmacy and Pharmacology, 10(46), 984-994 (2016)
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