Name | 3,3',4',5,7-pentahydroxyflavone |
Synonyms | MELETIN QUERTINE Quercetin QUERCETINE C.I. 75670 CI NO 75670 XANTHAURINE FLAVIN MELETIN C.I. Natural Yellow 10 LABOTEST-BB LT00455149 3,3',4',5,7-pentahydroxyflavone 3,3,4,5,7-Pentahydroxyflavone (pract) 3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one 3,3',4',5,7-Pentahydroxyflavone2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one |
CAS | 117-39-5 |
EINECS | 204-187-1 |
InChI | InChI=1/C15H10O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-6,16-19H |
InChIKey | REFJWTPEDVJJIY-UHFFFAOYSA-N |
Molecular Formula | C15H10O7 |
Molar Mass | 302.24 |
Density | 1.3616 (rough estimate) |
Melting Point | 316.5 °C |
Boling Point | 363.28°C (rough estimate) |
Flash Point | 239.5°C |
Solubility | Very slightly soluble in ether, insoluble in cold water, hardly soluble in hot water, soluble in glacial acetic acid and alkaline aqueous solution, showing yellow color. |
Vapor Presure | 9.03E-16mmHg at 25°C |
Appearance | Yellow needle crystal |
Merck | 13,8122 |
BRN | 317313 |
pKa | 6.31±0.40(Predicted) |
Storage Condition | room temp |
Refractive Index | 1.4790 (estimate) |
MDL | MFCD00006828 |
Physical and Chemical Properties | Melting point 314-317°C water-soluble <0.1g/100 mL at 21°C |
Use | With good expectorant, cough, asthma, for the treatment of chronic bronchitis, coronary heart disease and hypertension patients also have adjuvant therapy |
Risk Codes | R25 - Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
UN IDs | 2811 |
WGK Germany | 3 |
RTECS | LK8750000 |
HS Code | 29329990 |
Hazard Class | 6.1(b) |
Packing Group | III |
Toxicity | LD50 oral in rat: 161mg/kg |
Plant source: | Sophora japonica |
(IARC) carcinogen classification | 3 (Vol. Sup 7, 73) 1999 |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
expectorant | quercetin is an expectorant commonly used in Chinese medicine clinic. This product has good expectorant and antitussive effects, as well as certain antiasthmatic effects, and has the pharmacological functions of lowering blood pressure, improving capillary resistance, reducing capillary fragility, lowering blood lipids, dilating coronary arteries, and increasing coronary blood flow. clinical quercetin is mainly used for bronchitis and phlegm inflammation. It also has an adjuvant therapeutic effect on patients with coronary heart disease and hypertension. With this product, there can be dry mouth, dizziness and burning sensation in the stomach, which can disappear after stopping the drug. Quercetin is widely found in angiosperms, such as red tube medicine, cat's eye, iron clad gold, manshanhong, lobular loquat, purple flower rhododendron, Zhaoshanbai, dwarf tea, apocynum venetum are all contained. This substance is a kind of aglycone, which is often combined with sugar and exists in the form of glycosides, such as quercitrin, rutin, hyperin, etc. |
plant source | quercetin is a flavonol compound with a variety of biological activities widely distributed in the plant kingdom. It is found in a variety of vegetables and fruits, such as acai berries, broccoli and apples, as well as in foods such as tea, red wine, olive oil and propolis. Among them, it is found in the stems and leaves of Sophora japonica, buckwheat, sea buckthorn, Hawthorn and onion. Quercetin mainly comes from acerola cherry, tea, red onion, raspberry, bilberry and other plants. Quercetin content in some vegetables and fruits in the American flavonoids database. |
pharmacological action | quercetin can significantly inhibit the action of cancer promoters, inhibit the growth of malignant cells in vitro, and inhibit the synthesis of DNA, RNA and protein in Ehrlich ascites cancer cells. Quercetin can inhibit platelet aggregation and release of 5-hydroxytryptamine (5-HT), and can significantly inhibit platelet aggregation induced by ADP, thrombin and platelet activating factor (PAF), among which, it has the strongest inhibitory effect on PAF and can also significantly inhibit the release of 3H-5-HT induced by thrombin in rabbit platelets. (1) intravenous drip of quercetin at a concentration of 0.5mmol/L 10 ml/kg can significantly shorten the duration of arrhythmia in myocardial ischemia-reperfusion in mice, reduce the incidence of ventricular fibrillation, reduce MDA content and xanthine oxidase activity in myocardial tissue of ischemic perfusion area, and have obvious protective effect on SOD, which may be related to inhibiting the formation of oxygen free radicals in myocardium and protecting SOD or directly scavenging oxygen free radicals in myocardial tissue. (2) in vitro test of quercetin and rutin can disperse platelet thrombus adhering to rabbit aortic endothelium, and its EC50 is 80 and 500nmol/L respectively. Quercetin 50~500 μmol/L in vitro test can increase the cAMP level of human platelets, increase the cAMP level of human platelets and inhibit the aggregation of human platelets induced by ADP. Quercetin 2~50 μmol/L has concentration-dependent enhancement effect. The concentration of 300 μmol/L quercetin in the test tube can almost completely inhibit the platelet aggregation induced by platelet activating factor (PAF) in rats, and also inhibit the platelet aggregation induced by thrombin and ADP, and inhibit the release of 3H-5HT induced by thrombin in rabbits. The concentration of 30 μmol/L can significantly reduce the membrane fluidity of rat platelet. (3) quercetin at a concentration of 4 × 10-5~1 × 10-1g/ml has inhibitory effect on histamine release and SRS-A from guinea pig lungs sensitized by ovalbumin. 1 × 10-5g/ml also has inhibitory effect on SRS-A-induced ileum contraction in guinea pigs. Quercetin concentration of 5~50 μmol/L has a concentration-dependent inhibitory effect on histamine release from human basophilic leukocytes caused by ragweed antigen. There was a concentration-dependent inhibition of ileal contraction in ovalbumin-sensitized guinea pigs with an IC50 of 10 μmol/L. 5 × 10-6~5 × 10-5mol/L can inhibit the proliferation of mouse cytotoxic T lymphocytes (CTL) and also inhibit the DNA synthesis induced by ConA. |
efficacy and action | quercetin, as the most common flavonoid compound, has a variety of biological activities, can resist oxidation, and plays an important role in the clinical treatment of cancer and cardiovascular diseases. Antioxidant function Quercetin not only participates in antioxidant in vitro, can inhibit DNA oxidative damage, but also can protect tissues from oxidative damage by reducing the concentration of peroxide in tissues in vivo. Anti-cancer effect On the one hand, quercetin can effectively inhibit the production of free radicals. Its flavonoids such as quercetin can significantly reduce the incidence of gastric cancer, directly inhibit the growth of cancer cells or may act on the cell transduction pathway of cancer cell proliferation. On the other hand, it can enhance the effect of anticancer drugs and significantly improve the efficacy. Protecting cardiovascular The third major effect of quercetin is to protect the cardiovascular system. It is mainly reflected in five aspects: dilating blood vessels and lowering blood pressure; preventing and treating coronary heart disease: through animal experiments, the functions of reducing the incidence of myocardial infarction, mortality and lowering blood sugar were also found; reducing myocardial hypertrophy; inhibiting proliferation and hypertrophy of vascular smooth muscle cells; anti-thrombosis. In addition, quercetin has neuroprotective, anti-inflammatory and antiviral effects. Anti-inflammatory effect: In the human immune system against bacterial invasion, lipopolysaccharide (LPS) can cause the body's immune response and inflammatory response. Some studies have shown that quercetin has an inhibitory effect on the inflammatory response induced by LPS. antibacterial effect: quercetin is also a broad-spectrum antibacterial substance, which can be used to prevent and treat various bacterial infectious diseases. antiviral effect: quercetin can resist a variety of viruses, such as HIV virus, antisarcoma virus, human herpes simplex virus, parainfluenza virus type 3 (Pf-3), respiratory syncytial virus (RSV). |
preparation | quercetin and its derivatives are widely found in various vegetables and fruits, and can be obtained from lily plant onion and other plant extracts such as rutin, rutin, isosin, anisin, rutin, rutin and lautein. It can also be prepared by hydrolysis of rutin. The synthesis reaction formula of quercetin is as follows: fig. 1 the experimental operation of the synthesis reaction formula of quercetin: the method 1. accurately weigh 4.00g (about 2.69mmol) of refined rutin and place it in a 500mL round bottom flask, add 400mL of 2% dilute sulfuric acid, react at 80-90 ℃ for 4h,TLC tracks until the reaction is over, lets stand for 4h, performs decompression filtration, the filter cake is washed with distilled water to be neutral, and dried to obtain THQ crude.. The crude product was recrystallized with 400mL absolute ethanol to obtain 2.41g of yellow powder quercetin. Methods The ultrasonic-mechanical oscillation assisted extraction method was 2. to accurately weigh about 0.4g of Guizhou Liping Touguxiang leaf sample, and in a 50ml plug centrifugal tube, the extraction solvent was methanol: 6.5mol/L hydrochloric acid solution as a 4:1 mixed solution, added and mixed according to the solid-liquid ratio of 1:70. After ultrasound for 40min at ultrasonic frequency of 59Hz, ultrasonic power of 100W and water bath temperature of 65 ℃, the extraction was oscillated at room temperature for 30min, take out, place to room temperature, weigh (make up the lost weight with methanol), shake well, centrifuge at 8000r /min for 10min, take the supernatant, pass through 0.2m filter membrane, and be tested. |
use | antioxidant. Mainly used in oils, beverages, cold drinks, meat processing products. It has good expectorant, antitussive and antiasthmatic effects, is used to treat chronic bronchitis, and also has adjuvant therapeutic effects on patients with coronary heart disease and hypertension Analytical standard A flavonoid with anti-cancer activity, which is an inhibitor of mitochondrial ATPase and phosphodiesterase, inhibits PI3 kinase activity and slightly inhibits PIP kinase activity, IC50:3.8 μM. It has an antiproliferative effect on cancer cell strains, reduces cancer cell growth through type II estrogen receptors, and blocks human leukemia T cells at the G1 stage of the cell cycle. Inhibition of fatty acid synthase activity. |
Production method | Grind the bark of Quercus (Quercus) plants of the beech family into powder, wash it with hot salt water, extract it with dilute ammonia water, and neutralize it with dilute sulfuric acid. The filtrate is boiled and crystallized. It can be extracted from lily plant onion (Alliumcepa) with 95% ethanol; it can also be extracted from rutin (rutin) extract and quercitrin, isoquercitrin, anisin, hyperin, quercitrin, quercitrin, wintere glycoside, etc. are hydrolyzed by rutin decomposing enzyme or acidic aqueous solution. |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |