486-66-8 Usage
Description
Daidzein is an endocrine-active estrogenic isoflavone, a phytoestrogen that can bind to estrogen receptors and exert estrogenic effects in vivo. It is a pale-yellow prismatic crystal with a melting point of 315–323°C and is soluble in ethanol and ether. Daidzein is mainly derived from leguminous plants, such as soybeans, red clover grass, and Pueraria roots. It has been recognized for its medicinal value since 2838 BC and is a primary component of radix puerariae (Gegen), which has various health benefits, including reducing fever, promoting saliva production, and relieving diarrhea.
Uses
1. Used in Pharmaceutical Applications:
Daidzein is used as an inactive analog of Genistein, blocking the G1 phase of the cell cycle in Swiss 3T3 cells by inhibiting casein kinase II activity. It also inhibits the action of GABA on recombinant GABAA receptors.
2. Used in Cancer Treatment:
Daidzein is used as an inhibitor of carbonic anhydrase (CA), selectively targeting CAVII and CAXII, which helps in reducing tumor growth in a PC3 prostate cancer mouse orthotopic model when administered at a dose of 50 mg/kg per day. It also potentiates the effects of radiation therapy.
3. Used in Soy Isoflavone Research:
Daidzein, along with other isoflavone compounds such as genistein, is present in a number of plants and herbs, particularly in soybeans. It is a part of the soy isoflavone group, which is found in and isolated from soybeans and has various health benefits.
4. Used in Traditional Medicine:
Daidzein is a key component of radix puerariae (Gegen), which is used in traditional medicine for its various therapeutic properties, such as reducing fever, promoting saliva production, and relieving diarrhea.
5. Used in Research on Estrogen Receptor Binding:
Daidzein is used as a research compound to study its binding to estrogen receptor β (ERβ) and its estrogenic effects in vitro, as it increases gene transcription mediated by the estrogen response element (ERE) in an ERβ-dependent manner.
6. Used in Chemical Research:
Daidzein is an off-white crystalline solid that is a member of the class of 7-hydroxyisoflavones, which can be used in chemical research to study its properties and potential applications in various fields.
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.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 486-66-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 6 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 486-66:
(5*4)+(4*8)+(3*6)+(2*6)+(1*6)=88
88 % 10 = 8
So 486-66-8 is a valid CAS Registry Number.
InChI:InChI=1/C15H10O4/c16-10-6-4-9(5-7-10)11-8-19-13-3-1-2-12(17)14(13)15(11)18/h1-8,16-17H
486-66-8Relevant articles and documents
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Kazakov et al.
, (1975)
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P-450-DEPENDENT OXIDATIVE REARRANGEMENT IN ISOFLAVONE BIOSYNTHESIS: RECONSTITUTION OF P-450 AND NADPH:P-450 REDUCTASE
Hakamatsuka, Takashi,Hashim, Muhammed Faisal,Ebizuka, Yutaka,Sankawa, Ushio
, p. 5969 - 5978 (1991)
The reaction mechanism of oxidative rearrangement in the conversion of liquiritigenin, a flavanone, into 2,7,4'-trihydroxyisoflavanone was studied in elicitor-challenged Pueraria lobata cell cultures.The involvement of cytochrome P-450 in the reaction, hydroxylation associated with 1,2-aryl migration, was proved previously by the inhibition experiments with carbon monoxide and P-450 inhibitors.In order to obtain rigorous evidence proving that the enzyme is a P-450, a reconstitution experiment was performed with solubilized cytochrome P-450 and NADPH:cytochrome P-450 reductase fractions.During these studies we noticed that various biosynthetic reactions can be interpreted as P-450-mediated reactions associated with migration or bond cleavage.Ring contraction of 7-hydroxy-kaurenoic acid in gibberellin biosynthesis, the formation of a furan ring in furanocoumarin biosynthesis and several rearrangement reactions in steroid metabolism are discussed as examples of P-450 reactions associated with migration or bond cleavage.
Structure–activity relationship of phytoestrogen analogs as ERα/β agonists with neuroprotective activities
Cho, Hye Won,Gim, Hyo Jin,Li, Hua,Subedi, Lalita,Kim, Sun Yeou,Ryu, Jae-Ha,Jeon, Raok
, p. 99 - 105 (2021/01/06)
A set of isoflavononid and flavonoid analogs was prepared and evaluated for estrogen receptor α (ERα) and ERβ transactivation and anti-neuroinflammatory activities. Structure–activity relationship (SAR) study of naturally occurring phytoestrogens, their metabolites, and related isoflavone analogs revealed the importance of the C-ring of isoflavonoids for ER activity and selectivity. Docking study suggested putative binding modes of daidzein 2 and dehydroequol 8 in the active site of ERα and ERβ, and provided an understanding of the promising activity and selectivity of dehydroequol 8. Among the tested compounds, equol 7 and dehydroequol 8 were the most potent ERα/β agonists with ERβ selectivity and neuroprotective activity. This study provides knowledge on the SAR of isoflavonoids for further development of potent and selective ER agonists with neuroprotective potential.
Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water
Chang, Ya-Ting,Liu, Ling-Jun,Peng, Wen-Sheng,Lin, Lin-Ting,Chan, Yi-Tsu,Tsai, Fu-Yu
, p. 469 - 475 (2021/02/03)
Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)2/2,2′-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80°C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO3 and a higher reaction temperature (120°C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.
Synthesis of daidzein glycosides, α-tocopherol glycosides, hesperetin glycosides by bioconversion and their potential for anti-allergic functional-foods and cosmetics
Fujitaka, Yuya,Hamada, Hiroki,Uesugi, Daisuke,Kuboki, Atsuhito,Shimoda, Kei,Iwaki, Takafumi,Kiriake, Yuya,Saikawa, Tomohiro
, (2019/08/21)
Daidzein is a common isoflavone, having multiple biological effects such as anti-inflammation, anti-allergy, and anti-aging. α-Tocopherol is the tocopherol isoform with the highest vitamin E activity including anti-allergic activity and anti-cancer activity. Hesperetin is a flavone, which shows potent anti-inflammatory effects. These compounds have shortcomings, i.e., water-insolubility and poor absorption after oral administration. The glycosylation of bioactive compounds can enhance their water-solubility, physicochemical stability, intestinal absorption, and biological half-life, and improve their bio- and pharmacological properties. They were transformed by cultured Nicotiana tabacum cells to 7-β-glucoside and 7-β-gentiobioside of daidzein, and 30- and 7-β-glucosides, 30,7-β-diglucoside, and 7-β-gentiobioside of hesperetin. Daidzein and α-tocopherol were glycosylated by galactosylation with β-glucosidase to give 40- and 7-β-galactosides of daidzein, which were new compounds, and α-tocopherol 6-β-galactoside. These nine glycosides showed higher anti-allergic activity, i.e., inhibitory activity toward histamine release from rat peritoneal mast cells, than their respective aglycones. In addition, these glycosides showed higher tyrosinase inhibitory activity than the corresponding aglycones. Glycosylation of daidzein, α-tocopherol, and hesperetin greatly improved their biological activities.
