2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
Kaempferol
CAS: 520-18-3
Molecular Formula: C15H10O6
2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one - Names and Identifiers
| Name | Kaempferol |
| Synonyms | c.i.75640 kampherol campherol kempferol Kaempferol kaempherol C.I. 75640 indigoyellow 5,7,4'-trihydroxyflavonol 3,5,7,4-Tetrahydroxyflavone 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one 2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-on |
| CAS | 520-18-3 |
| EINECS | 208-287-6 |
| InChI | InChI=1/C15H10O6/c16-7-1-2-9(10(18)3-7)13-6-12(20)15-11(19)4-8(17)5-14(15)21-13/h1-6,16-19H |
| InChIKey | IYRMWMYZSQPJKC-UHFFFAOYSA-N |
2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one - Physico-chemical Properties
| Molecular Formula | C15H10O6 |
| Molar Mass | 286.24 |
| Density | 1.2981 (rough estimate) |
| Melting Point | 276°C |
| Boling Point | 348.61°C (rough estimate) |
| Flash Point | 240.7°C |
| Solubility | Slightly soluble in water, soluble in hot ethanol, ether and alkali. |
| Vapor Presure | 6.38E-16mmHg at 25°C |
| Appearance | Yellow powder |
| Color | yellow |
| Merck | 14,5274 |
| BRN | 304401 |
| pKa | 6.34±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Unstable in Solution |
| Refractive Index | 1.4413 (estimate) |
| MDL | MFCD00016938 |
| Physical and Chemical Properties | Yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Kaempferia rhizome, Locust, tea, broccoli, grapefruit. |
2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R68 - Possible risk of irreversible effects R25 - Toxic if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S36/37/38 - S22 - Do not breathe dust. |
| UN IDs | 2811 |
| WGK Germany | - |
| RTECS | LK9275200 |
| FLUKA BRAND F CODES | 8-10-23 |
| HS Code | 29329990 |
2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one - Introduction
Pharmacological effect: antibacterial, it has inhibitory effect on Staphylococcus aureus, Pseudomonas aeruginosa, Typhoid bacillus and Shigella. Cough, treat bronchitis. Enzyme inhibition, inhibition of eye aldose reductase, is beneficial to the treatment of diabetic cataract. It has mutagenic activity and can inhibit lymphocyte proliferation when the concentration is 1 × 10-4mol/L. Mainly used for anti-cancer, anti-fertility, anti-epilepsy, anti-inflammatory, antioxidant, antispasmodic, anti-ulcer, choleretic diuretic, cough.
Last Update：2022-10-16 17:25:49
2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one - Reference Information
| color index | 75640 |
| (IARC) carcinogen classification | 3 (Vol. 31, Sup 7) 1987 |
| overview | flavone is a natural polyphenol compound, which exists in a large number of fruits and vegetables eaten by human daily. it has many biological activities such as antioxidant, anticancer and anti-inflammatory, and has always been a hot research topic at home and abroad. kaempferol (kaempferol) is a kind of flavonoid compound, also known as kaempferol -3, kaempferol, kaempferol, thyphene III, widely exists in fruits, vegetables and Chinese herbal medicine and other natural plants. |
| effect | kaempferol has antioxidant, anti-inflammatory, anti-cancer, prevention and treatment of diabetes, atherosclerosis and osteoporosis, as well as protection of nerve, liver and myocardium, inhibition of protein kinase and other nutritional and health effects. As a health food and medicine, kaempferol has a very broad market. |
| preparation | 1) hydrolysis to prepare hydroxyacetophenone intermediate 1.1) put 30g of dihydromyricetin with a content of more than 98% into the reactor, then add 400g of sodium hydroxide solution with a mass fraction of 15%, stir and mix evenly, raise the temperature and reflux, and carry out hydrolysis reaction; High performance liquid chromatography monitoring, with the hydroxyacetophenone intermediate no longer increasing as the reaction control end point, after 2 hours, stop the reaction. Cooling to 30 ℃, slowly dropping 50% hydrochloric acid solution into the reaction solution, adjusting pH to about 6.2, stirring for 2 hours, standing for 1 hour, filtering to obtain light yellow viscous solid. 1.2) 150g of 95% ethanol is added to the light yellow viscous solid obtained in step 1.1), heated and refluxed for 1h, then filtered to obtain a solid while hot, then 90g of 95% ethanol is added to the solid, heated and refluxed for 1h again, beaten to room temperature, let stand for 2h, then filtered and dried to obtain a light yellow solid, I .e. hydroxyacetophenone intermediate (2-hydroxy -1-(2,4, 6-trihydroxyphenyl) acetyl) 17.8g. 2) Catalytic closed-loop preparation of crude dihydrokaempferol 2.1) Put 17.8g of hydroxyacetophenone intermediate obtained by the reaction in step 1.2) into the reaction bottle, add DMF92g, and stir to completely dissolve the hydroxyacetophenone intermediate. 2.2) Add 3.55g of proline to the solution in step 2.1), raise the temperature to 65 ℃ and keep the temperature unchanged, dissolve 13.9g of p-hydroxybenzaldehyde with 20gDMF and slowly drop it into the reaction bottle for about 2 hours. After dropping, the temperature was raised to 70 ℃ for heat preservation, and the catalytic closed-loop reaction was carried out. High performance liquid chromatography monitoring was carried out. The dihydrokaempferol intermediate was no longer increased as the reaction control end point, and the reaction ended after about 7 hours. 2.3) The solution obtained in step 2.2) is reduced to room temperature, 350g of 5% glacial acetic acid solution is added, stirred for 2 hours, and solid is slowly precipitated. Filter, wash the filter cake with water until neutral and dry to obtain 27.6g of crude dihydrokaempferol. 3) Oxidation Preparation of kaempferol 27.6g of crude dihydrokaempferol obtained in step 2.3) is put into a reaction bottle, 275ml of 65% ethanol is added, stirred evenly, 6g of anhydrous potassium carbonate is added, oxygen is introduced, then the temperature is raised and refluxed, the oxidation reaction is carried out, high performance liquid chromatography monitoring is carried out, the reaction control endpoint is no longer increased with kaempferol, and the reaction is over after about 8 hours. Drop to room temperature and leave overnight, filter to obtain yellow solid, add 200g of water, filter after reflux for 2h, wash and dry the filter cake to obtain 22.3g of kaempferol with 98% content (HPLC). |
| traits | kaempferol is brown to light yellow crystalline powder; The gas is slight and the taste is pungent. |
| pharmacological effects | kaempferol has anti-cancer, anti-fertility, anti-epilepsy, anti-inflammatory, antioxidant, antispasmodic, anti-ulcer, choleretic diuretic, antitussive and other effects. |
| use | an effective osteoclast bone resorption inhibitor. It has anti-cancer, anti-fertility, anti-epilepsy, anti-inflammatory, antioxidant, antispasmodic, anti-ulcer, choleretic and diuretic, and cough. a flavonol. It can restore the deformation of mouse fibroblasts treated with phorbol ester or v-H-ras-transformed NIH 3T3 cells. It can significantly induce nuclear DNA degradation, accompanied by lipid peroxidation. Inhibition of DNA reattachment catalyzed by topoisomerase I. |
| production method | after the plant material is crushed, the plant material is extracted with water or ethanol; then polyamide (polyamide) is used for adsorption, and after elution, it is separated from other flavonoids by chromatography or purified by high pressure liquid chromatography (HPLC). |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:09
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