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D7802

Sigma-Aldrich

Daidzein

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

Synonyme(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

Formule empirique (notation de Hill):
C15H10O4
Numéro CAS:
486-66-8
Poids moléculaire :
254.24
Numéro Beilstein :
231523
Numéro CE :
207-635-4
Numéro MDL:
MFCD00016954
Code UNSPSC :
12352202
ID de substance PubChem :
24278030
Nomenclature NACRES :
NA.77

product name

Daidzein, ≥98%, synthetic

Source biologique

synthetic

Niveau de qualité

200

Pureté

≥98%

Forme

powder

Pf

>290 °C

Solubilité

DMSO: 10 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

ZQSIJRDFPHDXIC-UHFFFAOYSA-N

Informations sur le gène

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

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Description générale

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

Actions biochimiques/physiologiques

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.

Conditionnement

Packaged under Argon.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
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)
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)
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