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Daidzein

analytical standard

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:
85151701
PubChem Substance ID:
329751271
NACRES:
NA.24

grade

analytical standard

Quality Level

100

Assay

≥97.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

food and beverages

format

neat

storage temp.

2-8°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

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General description

Daidzein is an endocrine-active estrogenic isoflavone. This phytoestrogen is capable to bind to estrogen to exert estrogenic effects in vivo. It can naturally be found in soybean seed and flour.

Application

Daidzein was used as standard in determination of daidzein and genistein, in soybean food using in-tube solid-phase microextraction coupled to high-performance liquid chromatography (in-tube SPME–HPLC). It was also used as reference standard in determination of isoflavones in red clover using high-performance liquid chromatography–UV–electrospray ionization-mass spectrometric detector (HPLC–UV–ESI-MSD).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
WXBF1553V
WXBD5206V
WXBD1344V
WXBC8222V
WXBC6768V

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Sigma-Aldrich

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Daidzein Inactive analog of Genistein.

Sigma-Aldrich

251600

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Sigma-Aldrich

G6649

Genistein

Determination of daidzein and genistein in soybean foods by automated on-line in-tube solid-phase microextraction coupled to high-performance liquid chromatography.
Mitani K, Narimatsu S, Kataoka H.
Journal of Chromatography A, 986(2), 169-177 (2003)
Determination of isoflavones in red clover and related species by high-performance liquid chromatography combined with ultraviolet and mass spectrometric detection.
Wu Q, Wang M, Simon JE.
Journal of Chromatography A, 1016(2), 195-209 (2003)
Developmental effects of dietary phytoestrogens in Sprague-Dawley rats and interactions of genistein and daidzein with rat estrogen receptors alpha and beta in vitro.
Casanova, Mercedes, et al.
Toxicological Sciences, 51.2, 236-244 (1999)
Ivonne M C M Rietjens et al.
Molecular nutrition & food research, 57(1), 100-113 (2012-11-24)
Isoflavones are phytoestrogens that have been linked to both beneficial as well as adverse effects in relation to cell proliferation and cancer risks. The present article presents an overview of these seemingly contradicting health effects and of mechanisms that could
Katherine A Jackman et al.
Current medicinal chemistry, 14(26), 2824-2830 (2007-11-30)
Isoflavones are an important class of phytoestrogens that are found at extrememly high levels in soy. Up until recently, daidzein and genistein were considered to be the most important and hence most studied isoflavones, however more recently attention has shifted
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