7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
Daidzein
CAS: 486-66-8
Molecular Formula: C15H10O4
7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one - Names and Identifiers
| Name | Daidzein |
| Synonyms | Daidsein DAIDZEIN Daidzein 4,7-Dihydroxyisoflavone 4',7-Dihydroxyisoflavone 4',7-dihydroxy-isoflavon 4,7-Dihydroxyisoflavone(Daidzein) DAIDZEIN, (AMERICAN HERBAL PHARMACOPOEIA) 5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one |
| CAS | 486-66-8 |
| EINECS | 207-635-4 |
| 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 |
7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one - Physico-chemical Properties
| Molecular Formula | C15H10O4 |
| Molar Mass | 254.24 |
| Density | 1.1629 (rough estimate) |
| Melting Point | 315-323°C (dec.) |
| Boling Point | 317.45°C (rough estimate) |
| Flash Point | 190°C |
| Water Solubility | insoluble |
| Solubility | Soluble in ethanol and ether. |
| Vapor Presure | 4.53E-10mmHg at 25°C |
| Appearance | Pale yellow crystals. |
| Color | White to off-white |
| Merck | 14,2801 |
| BRN | 231523 |
| pKa | 7.01±0.20(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.4300 (estimate) |
| MDL | MFCD00016954 |
| Physical and Chemical Properties | From the legume plant soybean. |
| Use | It can promote the growth of livestock, poultry, fish, shrimp and other animals, and has the effect of adjuvant therapy for coronary heart disease |
7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/38 - Irritating to eyes and skin. |
| Safety Description | 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 |
| HS Code | 29329990 |
| Hazard Class | IRRITANT |
7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one - Upstream Downstream Industry
| Raw Materials | Hydrochloric acid Ethyl Alcohol Ether |
7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one - Reference Information
| Plant source: | Soybean |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | isoflavone compound daidzein (daidzein,4 ',7 dihydroxyisoflavone, hereinafter referred to as d) as one of the main effective ingredients of kudzu root and soybean, it has obvious antiarrhythmic, anti-hypoxia-ischemia, anticonvulsant, estrogen, promoting the formation of bone cells and inhibiting the growth of cancer cells. Tablets or capsules made from d are mainly used to treat coronary heart disease, cerebral thrombosis, cerebral infarction and sequelae of cerebral bleeding. Also can be used for neck pain, headache, dizziness and early sudden deafness caused by hypertension. However, due to the limitation of the structure of the D molecule , the water solubility and fat solubility are very poor, resulting in some drawbacks in clinical application, such as: biological benefits low usage, large dosage, slow absorption of the prepared tablets or capsules in the body, 7-14 days can be effective. In order to improve the solubility of d and solve the problems existing in clinical application, there are more than 50 kinds of d derivatives reported at home and abroad. Using D as the lead compound, it is an important topic to transform its chemical structure and find organisms with strong biological activity and high utilization. It is an important topic [1]. |
| HPLC detection conditions | C18( 4.6 × 250mm × 5mm) mobile phase: methanol: 0.1% formic acid water (43:57) detection wavelength: 250nm |
| Interaction with human serum albumin | The binding reaction between daidzein and human serum albumin (HSA) was studied by fluorescence quenching spectrum, synchronous fluorescence spectrum and ultraviolet-visible absorption spectrum. Daidzein has a strong fluorescence quenching effect on human serum albumin. The quenching mechanism belongs to static quenching, and intramolecular non-radiation energy transfer occurs. Using the Stern-Volmer equation to process the experimental data, the binding constants KA between daidzein and HSA are 0. 34 × 104(23 ℃), 1. 10 × 104(30 ℃) and 4. 36 × 104 L mol- 1(40 ℃). According to F?rster non-radiative energy transfer theory, the binding distances between daidzein and HSA were found to be 1. 50 nm(23 ℃), 1. 46 nm(30 ℃) and 1. 42 nm(40 ℃). By calculating the corresponding thermodynamic parameters, it can be seen that the interaction between daidzein and human serum albumin is a spontaneous process of Gibbs free energy reduction, and the main force type between the two is hydrophobic force. At the same time, the effect of daidzein on HSA conformation was investigated by synchronous fluorescence spectroscopy. experiments show that the fluorescence quenching of HSA by daidzein belongs to static quenching mechanism, and non-radiative energy transfer occurs in the molecule. The two are mainly combined by hydrophobic force, and the binding site is close to Trp residues in HSA, and the polarity of the microenvironment in which Trp residues are slightly reduced after binding, causing conformational changes in HSA. |
| antiarrhythmic effect | daidzein (3.0,5.0 mg kg- 1) has obvious preventive effect on chloroform-induced ventricular fibrillation in mice, and daidzein (0.8,1.0 mg kg- 1) has obvious therapeutic effect on aconitine-induced arrhythmia in rats. Daidzein (0.2,0.3 mg kg-1) can also resist adrenaline-induced arrhythmia in rabbits. Daidzein (0.03%,0.05%) can significantly reduce the amplitude of action potential of isolated sciatic nerve of toad. Daidzein (0.8,1.0 mg kg-1) has preventive effect on ventricular fibrillation induced by calcium chloride in rats and can significantly reduce the mortality rate of rats. The above effects have obvious dose dependence. daidzein has obvious antiarrhythmic effect. Aconitine can promote the opening of fast sodium channels, accelerate Na + inflow and cause multi-source ectopic rhythm. Daidzein can effectively resist, which suggests that daidzein may have obvious inhibitory effect on Na + inflow of myocardial cell membrane. Daidzein also has procaine-like local anesthesia, and its ability to penetrate the sciatic nerve is similar to procaine. The amplitude of action potential in isolated sciatic nerve of toad is mainly caused by Na + inflow, which is reduced by daidzein, which further indicates that daidzein has inhibitory effect on Na + inflow. Therefore, the antiarrhythmic effect of daidzein may be related to the inhibition of Na + or Ca2 + influx and anti-β-adrenoceptor. |
| synthesis | after comparison, resorcinol and p-hydroxyphenylacetic acid are used as raw materials, and daidzein is generated under the action of anhydrous zinc chloride catalytic condensation and dimethylformamide dimethylacetal-carbon unit transfer agent. The yield of the product is as high as 43.0%, and the quality meets the pharmacopoeia standard. Reaction principle 1. Condensation reaction Figure 1 Condensation reaction in the synthesis of daidzein 2. Cyclic reaction Figure 2 Cyclic reaction in the synthesis of daidzein |
| reference | [1] Liu Qianguang, Zhang Zunting, Xue Dong. Synthesis, Crystal Structure and Activity of Daidzein Sulfonate [J]. Journal of Chemistry of Colleges and Universities, 2003,(05):820-825. [2] Wu Qiuhua, Wang Dongyue, Zhou Xin, Zhang Zhiheng, Liu Weihua, wang zhi. study on the interaction between daidzein and human serum albumin [J]. spectroscopy and spectral analysis, 2009,29(07):1911-1914. [3] daidzein. Lilac Tong. [Citation Date 2017.08.29] [4] Liu Min, Zhang Cuie, Li Purui, Ji Mingli. Synthesis of Daidzein [J]. Fine Chemical Intermediates, 2009,39(06):34-36. |
| use | can promote the growth of animals such as livestock, poultry, fish and shrimp, and has adjuvant therapeutic effect on coronary heart disease vasodilators. a phytoestrogen. |
Last Update：2024-04-09 20:52:54
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View History
7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
3-(1-ethoxyethoxy)-3,7-dimethylocta-1,6-diene
1-(2-Tetrahydropyranyl)-1H-pyrazole-4-boronic acid pinacol ester
3-(1-ethoxyethoxy)-3,7-dimethylocta-1,6-diene
1-(2-Tetrahydropyranyl)-1H-pyrazole-4-boronic acid pinacol ester
Raw Materials for 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one