ChemicalBook--->CAS DataBase List--->486-66-8

486-66-8

486-66-8 Structure

486-66-8 Structure
IdentificationMore
[Name]

Daidzein
[CAS]

486-66-8
[Synonyms]

4',7-DIHYDROXYISOFLAVONE
4,7-DIHYDROXYISOFLAVONE
7,4'-DIHYDROXYISOFLAVONE
7-HYDROXY-3-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
7-HYDROXY-3-(4-HYDROXY-PHENYL)-CHROMEN-4-ONE
7-HYDROXY-3-(4-HYDROXYPHENYL)CHROMONE
AKOS NCG1-0027
DAIDZEIN
ISOFLAVONE
4’,7-dihydroxy-isoflavon
7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyrone
7-hydroxy-3-(4-hydroxyphenyl)-4h-1-benzopyran-4-on
daidzeol
k251b
Daidsein
4,7-Dihydroxyisoflavone(Daidzein)
DAIDZEIN, 98+% FROM SOYBEAN
DAIDZEIN, (AMERICAN HERBAL PHARMACOPOEIA)
DAIDZEIN, 98% SYNTHETIC
DAIDZEIN, STANDARD FROM SOYBEAN 99+%(HPLC)
[EINECS(EC#)]

207-635-4
[Molecular Formula]

C15H10O4
[MDL Number]

MFCD00016954
[Molecular Weight]

254.24
[MOL File]

486-66-8.mol
Chemical PropertiesBack Directory
[Appearance]

Off-White Crystalline Solid
[Melting point ]

315-323°C (dec.)
[Boiling point ]

317.45°C (rough estimate)
[density ]

1.1629 (rough estimate)
[refractive index ]

1.4300 (estimate)
[storage temp. ]

2-8°C
[solubility ]

DMSO: 10 mg/mL
[form ]

Powder
[pka]

7.01±0.20(Predicted)
[color ]

White to off-white
[Water Solubility ]

insoluble
[Usage]

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:25
[Detection Methods]

HPLC,NMR
[Merck ]

2801
[BRN ]

231523
[CAS DataBase Reference]

486-66-8(CAS DataBase Reference)
[EPA Substance Registry System]

486-66-8(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/38:Irritating to eyes and skin .
[Safety Statements ]

S24:Avoid contact with skin .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

3
[RTECS ]

DJ3100040
[HazardClass ]

IRRITANT
[HS Code ]

29329900
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Hydrochloric acid-->Diethyl ether
[Preparation Products]

6,7,4'-Trihydroxyisoflavone
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

4',7-Dihydroxyisoflavone(486-66-8).msds
Hazard InformationBack Directory
[Description]

Daidzein mainly comes from leguminous plants, the seeds of soybean (dadou), red clover grass, or all Pueraria roots. Its medicinal value was first recorded in Shen Nong Ben Cao Jing 2838 BC.?Daidzein, one of the main soy isoflavones, is also the main component of radix puerariae (Gegen) which is the dry root of kudzu leguminous plants. Radix puerariae can reduce fever, produce saliva, and relieve diarrhea. Its chemical composition is complicated, including puerarin, xyloside, soy flavonoids, soybean flavonoid glycosides, beta-sitosterol, daidzin, daidzein. The main effective components are puerarin and daidzein
[Chemical Properties]

Off-White Crystalline Solid
[Physical properties]

Appearance: pale-yellow prismatic crystal. Melting point: 315–323?°C. Solubility: soluble in ethanol and ether
[History]

Daidzein is a kind of isoflavone compound, which was first synthetized by researchers in China. It has been widely used in drugs, food supplements, and cosmetics. Because of two phenolic hydroxyl structures, Daidzein has poor water solubility, poor liposolubility, and strong first-pass effect, leading to the low bioavailability of oral absorption, which limits its widely clinical usage.
Ipriflavone is a kind of isoflavone modified from Daidzein, which has been used for the treatment of osteoporosis in Japan and some European countries. The effects of a series of amino alkoxy derivatives of ipriflavones on inhibiting the bone absorption were evaluated. The researchers found that 7-amino alkoxy derivative works best. When Daidzein was alkylated or acylated at 7-hydroxyl selectively, the stability was increased, and thus the proliferation of MCF-7 cell was inhibited.
[Uses]

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
[Uses]

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 e 4.44)
[Uses]

phytoestrogen
[Definition]

ChEBI: A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4'.
[Indications]

Daidzein is mainly used for the treatment of hypertension, coronary heart disease, cerebral thrombosis, and vertigo and aids in the treatment of sudden deafness. It can also treat women with menopause syndrome.
[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.
[Biological Activity]

Analog of the phytoestrogen genistein (5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one ). Blocks G 1 phase cell cycle progression and is an agonist at estrogen receptors.
[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.
[Pharmacology]

Daidzein has many kinds of pharmacological effects, such as anticancer, cardiovascular protection, estrogen- and antiestrogen-like effects, antiosteoporosis, antioxidation, improving immunity, and affecting the endocrine system. More attention has been paid by domestic and international pharmaceutical and food industries. Daidzein has obviously antibacterial effect on Staphylococcus aureus and Escherichia coli. It can also increase the weight of immune organs in mice and has anti-arrhythmic effect. The chemical structure of daidzein is very similar to the endogenous estrogen, so the estrogen-like effect is used to treat menopausal syndrome and increase the levels of osteocalcin (BGP) and also the bone mineral deposits. The clinical efficacy is similar to estrogen replacement therapy (ERT). Daidzein doesn’t induce the high expression of estrogen. It has effects on the osteoblast to reduce the bone absorption of osteoclast, thus maintains the dynamic balance of osteoblast and osteoclast, finally reduces the risk of fracture. So it is safe for usage. Daidzein can also increase the bone mineral density (BMD) and bone mineral content (BMC) of the lumbar spine, the number of trabecular bone, and bone volume fraction, improve the bone microstructure, and thus prevent the reduction of femur biomechanics in glucocorticoid-induced osteoporosis in the rat.
Daidzein has an anti-hypoxia effect. The study showed that Daidzein could significantly prolong the survival time of mice in hypoxia tolerance test under normal pressure and after subcutaneous injection of isoproterenol, suggesting that Daidzein has the significant anti-hypoxia effects. Daidzein plays a protective role in myocardial hypertrophy induced by isoproterenol in rat probably by the antioxidative effects. Similarly, Daidzein may protect the ischemia-reperfusion injury in rats by increasing the antioxidative capacity. Daidzein can significantly inhibit the proliferation of two human breast cancer cells (MCF-7 and MDA-MB-231) in?vitro with the significant dose-dependent and time-dependent effects. Daidzein can markedly decrease the colony-forming ability, suggesting that Daidzein may have the effect of preventing and treating breast cancer.
It was found that Daidzein has the obviously preventive effect on chloroforminduced ventricular fibrillation in mice, therapeutic effect on aconitine-induced arrhythmia in rats, as well as protective effect on the adrenaline-induced arrhythmia in rabbit. Daidzein can significantly reduce the action potential amplitude of sciatic nerve in toad in?vitro. All of the above effects were obviously dose-dependent, suggesting Daidzein has the significant anti-arrhythmic effects
[Clinical Use]

Daidzein can expand the coronary artery, femoral artery, and cerebral artery, increase cerebral blood flow and limb blood circulation, reduce blood viscosity and vascular resistance, decrease myocardial oxygen consumption, improve heartfunction, increase the microcirculation and blood flow to the tip, lower the blood pressure, and adjust the heart rhythm. Daidzein can be used for the treatment of hypertension, coronary heart disease, angina pectoris, myocardial infarction, cerebral thrombosis, dizziness, and sudden deafness. It can also be used for women’s menopause syndrome.
Spectrum DetailBack Directory
[Spectrum Detail]

Daidzein(486-66-8)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Daidzein, 98%(486-66-8)
[Alfa Aesar]

4',7-Dihydroxyisoflavone, 97%(486-66-8)
[Sigma Aldrich]

486-66-8(sigmaaldrich)
[TCI AMERICA]

Daidzein,>95.0%(LC)(T)(486-66-8)
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