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

• ChemBase ID: 60045
• Molecular Formular: C15H10O4
• Molecular Mass: 254.2375
• Monoisotopic Mass: 254.0579088
• SMILES: c1(c(=O)c2c(oc1)cc(cc2)O)c1ccc(cc1)O
• Canonical SMILES: Oc1ccc(cc1)c1coc2c(c1=O)ccc(c2)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: daidzein; 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• Synonyms: 7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Daidzeol; Isoaurostatin; Daidzein; 7-Hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; 4',7-Dihydroxyisoflavone; 7-Hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; Daidzein; 4',7-Dihydroxyisoflavone; 4′,7-Dihydroxy-iso-flavone; 7-Hydroxy-3-(4-hydroxy-phenyl)-4H-1-benzo-pyran-4-one; 7-Hydroxy-3-(4-hydroxy-phenyl)-chromone; Daidzein; 4',7-Dihydroxyisoflavone; Dimethylbiochanin B; Daizeol; 4',7-二羟基-异磺酮

Database IDs

• CAS Number: 486-66-8
• EC Number: 207-635-4
• MDL Number: MFCD00016954
• Beilstein Number: 231523
• Merck Index: 142801
• PubChem SID: 162025786; 24278030
• PubChem CID: 5281708
• CHEBI ID: 28197
• CHEMBL: 8145
• Chemspider ID: 4445025
• KEGG ID: C10208
• Unique Ingredient Identifier: 6287WC5J2L
• Wikipedia Title: Daidzein

CALCULATED PROPERTIES

• Acid pKa: 6.47684
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.6871917
• LogD (pH = 7.4): 1.7724496
• Log P: 2.7304378
• Molar Refractivity: 69.702 cm^3
• Polarizability: 26.477903 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble10 mg/mL
• Apperance: Off-White Solid; Pale yellow prisms; Powder
• Melting Point: 315-323°C; 315-323°C (dec.); 315–323 °C (decomposes); 315-323°C (dec); 328-332°C dec.

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: IRRITANT; Irritant/Light Sensitive/Store at -20°C
• RTECS: DJ3100040
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 24-26; 26-37-60; R
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... ESR1(2099), ESR2(2100), UGT1A4(54657)mouse ... Aldh1a2(19378), Hexa(15211), Maoa(17161)rat ... Aldh1a2(116676)
• Mechanism of Action: Antioxydant; Counteract damaging effects of free radicals in tissues, regulates cell division and cell survival

Product Information

• Purity: >98%; ≥97.0% (HPLC); ≥98%; ≥98.0% (TLC); 97%; 98%; 99.0
• Grade: analytical standard; purum
• Salt Data: Free Base
• Biological Source: synthetic; Widespread isoflavone in the Leguminosae (Papilionoideae) eg. in Chamaecytisus spp., Cytisus spp., Phaseolus spp. Also from Streptomyces xanthophaeus
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antiaggregant; Antialcoholic; Antioxydant
• Empirical Formula (Hill Notation): C15H10O4

DETAILS

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

Sigma Aldrich - 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.

Sigma Aldrich - 30405

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

Sigma Aldrich - 16587

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

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 Genistein^1 (tyrosine kinase inhibitor, Cat. No. 152355).

Toronto Research Chemicals - 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

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