529-44-2
Myricetin
CAS: 529-44-2
Molecular Formula: C15H10O8
529-44-2 - Names and Identifiers
| Name | Myricetin |
| Synonyms | Myricetin MYRISETIN Cannabiscetin MYRICETIN(CANNABISCETIN)(P) MYRICETIN(CANNABISCETIN)(RG) 3,3,4,5,5,7-Hexahydroxyflavone CANNABISCETIN(SEE MYRICETIN)(P) 3,3',4',5,5',7-Hexahydroxyflavone Myricetin, froM Myrica rubra (Lour.) Zucc. 3,3,4,4,5,7-hexahydro-2-phenyl-4H-chromen-4-one 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one 4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl) |
| CAS | 529-44-2 |
| EINECS | 208-463-2 |
| InChI | InChI=1/C15H10O8/c16-5-3-8(18)10-9(4-5)23-15(14(22)13(10)21)6-1-2-7(17)12(20)11(6)19/h1-4,16-20,22H |
| InChIKey | IKMDFBPHZNJCSN-UHFFFAOYSA-N |
529-44-2 - Physico-chemical Properties
| Molecular Formula | C15H10O8 |
| Molar Mass | 318.24 |
| Density | 1.4222 (rough estimate) |
| Melting Point | >300°C(lit.) |
| Boling Point | 377.41°C (rough estimate) |
| Water Solubility | Soluble in dimethyl sulfoxide,dimethyl formamide and ethanol. Insoluble in water. |
| Solubility | Soluble in methanol, ethanol, acetone, ethyl acetate, slightly soluble in water, insoluble in chloroform, petroleum ether. |
| Appearance | Yellow needle crystal |
| Color | Yellowish Brown |
| Merck | 14,6332 |
| BRN | 332331 |
| pKa | 6.30±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.4395 (estimate) |
| MDL | MFCD00006827 |
| Physical and Chemical Properties | Properties: light brown powder |
| Use | 1. Antagonism of platelet activating factor (PAF) Hypoglycemic effect 3. Antioxidant effect Hepatoprotective effect 5. Solution to mild alcoholism 6. Myricetin, an active ingredient in the bark and leaves of Myrica rubra, not only has the above-mentioned pharmacological effects, but also has anti-inflammatory, anti-tumor, anti-mutation, prevention of dental caries, anti-oxidation, elimination of free radicals in the body and other pharmacological activities. |
529-44-2 - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | LK8646000 |
| FLUKA BRAND F CODES | 10 |
| HS Code | 29329990 |
529-44-2 - Introduction
Pharmacological effect: antagonism of platelet activating factor (PAF). It has many cardiovascular pharmacological effects such as anti-thrombosis, anti-myocardial ischemia, and improvement of microcirculation.
Last Update：2022-10-16 17:25:55
529-44-2 - Reference Information
| Plant source | Myricetin, also known as myricetin and myricetin, is a flavonoid alcohol compound extracted from the bark of Myricaceae (Myricaceae). Myrica rubra is one of the subtropical fruit trees native to China. Wild species have grown for more than 7000 years and cultivated for more than 2000 years. China's East China and Hunan, Guangdong, Guangxi, Guizhou and other regions are extremely rich in bayberry bark resources. Pruned and discarded bayberry branches can be used as a long-term source of a large number of plants. However, due to the extraction process and other reasons, the current research on myricetin mainly comes from rattan tea, and the source of myricetin is very few. However, dihydromyricetin is mainly obtained in rattan tea and its resources are limited, which has certain limitations on the long-term development and utilization of myricetin. |
| use | myricetin is a flavonoid compound extracted from myrica rubra fruit, it has the functions of scavenging free radicals, anti-oxidation, anti-tumor, reducing neurotoxicity, affecting lymphocyte activation and proliferation, anti-platelet activating factor, lowering blood sugar, relieving alcohol poisoning, preventing alcoholic liver, fatty liver, inhibiting liver cell deterioration, reducing liver cancer The incidence rate, liver protection, anti-inflammatory and other effects, it can also strongly inhibit yeast α-glucosidase, glucosidase I, in vitro glucosidase I and xanthine oxidase in milk. Myricetin's main functions: 1) Antioxidant effect: Myricetin is a strong antioxidant. Oxidative stress plays a key role in various neurological diseases including ischemia and senile dementia. Myricetin reduces the production and toxicity of β-amylase through conformational changes, and can be used to count the progress of senile dementia. 2) Anti-tumor effect: Myricetin is an effective chemical control agent for carcinogenesis. 3) Reduce neurotoxicity: Myricetin can inhibit the neurotoxicity caused by glutamate through different ways to protect neurons, thereby effectively preventing nerve damage. 4) Effect on lymphocyte activation and proliferation: Myricetin can inhibit the expression of CD69, an early activation index of T cells, and can inhibit lymphocyte proliferation. 5) Antagonism of platelet activating factor (PAF): Myricetin inhibited PAF-induced WRP aggregation and 52HT release in vitro in a concentration-dependent manner. At the same time, it can obviously inhibit the increase of free calcium in platelets caused by PAF. Therefore, myricetin has many cardiovascular pharmacological effects such as anti-thrombosis, anti-myocardial ischemia, and improvement of microcirculation. 6) hypoglycemic effect: myricetin has obvious hypoglycemic effect. 7) The effect of protecting the liver and protecting the liver: Dihydromyricetin can significantly inhibit the increase of alanine aminotransferase (ALT) and aspartate aminotransferase (AST) activities in the serum and reduce the total serum bilirubin, which has obvious The effect of reducing enzyme yellowing. strong inhibition of yeast α-glucosidase, glucosidase I, in vitro glucosidase I and xanthine oxidase in milk. |
| Antagonism of Platelet Activating Factor (PAF) | Chen Wenmei and Zang Baoxia showed that myricetin could significantly inhibit the increase of free calcium in platelets caused by PAF and inhibit the specific binding of PAF to rabbit platelet receptors by measuring the aggregation of washed platelets (WRP) in rabbits. It shows that myricetin has anti-PAF effect and is a new PAF receptor antagonist. Therefore, myricetin has many cardiovascular pharmacological effects such as anti-thrombosis, anti-myocardial ischemia, and improvement of microcirculation. It is expected to be developed into a drug for promoting blood circulation and removing blood stasis. |
| hypoglycemic effect | foreign researchers Yoshikawa M found that myricetin has hypoglycemic effect on hyperglycemic mice when studying the mechanism of anti-diabetic mechanism drugs. Some studies have used alloxan-induced diabetes models, adrenaline and glucose-induced hyperglycemia mouse models, and normal mice. After oral administration, the blood sugar levels of each model mouse were measured. Results Myricetin has obvious hypoglycemic effect on diabetic mice caused by alloxan and hyperglycemia mice caused by epinephrine and glucose, and the therapeutic effect is good, but it has no obvious effect on blood sugar of normal mice. Myricetin has a good hypoglycemic effect on a variety of animal models, and it is expected to develop hypoglycemic drugs. Zhong Zhixian and other factors caused diabetes in mice, as well as normal mice, the blood sugar level of each model mouse was measured. Results Myricetin has obvious hypoglycemic effect on diabetic mice caused by alloxan and hyperglycemia mice caused by epinephrine and glucose, and the therapeutic effect is good, but it has no obvious effect on blood sugar of normal mice. In addition, in their further research, they found that myricetin has a good hypoglycemic effect on a variety of animal models, and it is expected to develop hypoglycemic drugs or use them as food additives for diabetic patients. |
| antioxidant effect | some studies have used Rancimat method to determine its antioxidant performance. the results show that it is an excellent antioxidant for oils and fats, and its effect is obviously stronger than that of synthetic antioxidant BHT ( 3, 5-di-tert-butyl-4-hydroxymethylbenzene) can be used as a natural antioxidant for food preservation with higher oils and fats. Other studies have shown that myricetin is a strong antioxidant, and oxidative stress plays a key role in various neurological diseases including ischemia and senile dementia. |
| liver and liver protection | myrica bark has the function of protecting liver, reducing enzyme and yellowing, enhancing non-specific immune function of mice and humoral immune function of mice with low immune function, thus playing a role in protecting liver. Zhong Zhengxian et al. used carbon tetrachloride, D2 galactosamine and naphthalene isothiocyanate to induce acute liver injury in mice to observe the protective effect of bayberry bark on liver injury. And observe the immune enhancement effect of bayberry bark. The results confirmed that myricetin can significantly reduce the content of toxic substances in the serum of mice model of acute liver injury induced by carbon tetrachloride, D2 galactosamine and naphthalene isothiocyanate, reduce the degeneration and necrosis of liver tissue, and improve the phagocytic function and hemolysin content of mononuclear macrophages. It shows that Myrica rubra bark element can protect liver, reduce enzyme and yellow, enhance non-specific immune function of mice and humoral immune function of mice with low immune function, thus playing a role in protecting liver and providing reference for clinical application of myrricetin. |
| solution light ethanol poisoning | Zhejiang folk have always used the tradition of red bayberry wine. red bayberry wine is sweet and not easy to intoxicate. Hase-K et al. found that myricetin has the effect of relieving alcoholism in the experiment of relieving alcoholism. Later, when studying the mechanism, it was found that the principle that myricetin can reduce ethanol poisoning is mainly to protect the liver and reduce the damage of hexanol to the liver. |
| clinical application | FDA has widely used myricetin in medicine, food, health care products and cosmetics. Foreign health products FYI has used myricetin as an additive to treat and prevent arthritis and various inflammations, especially for pregnant and lactating women and infants. Microherb high-purity myricetin (Myricetin) has been widely used in food, medicine and daily chemicals. With the further study of the pharmacological effects of myricetin, the market demand for myricetin will increase sharply, and the research and development prospects of myricetin are broad. bayberry is a specialty resource in China. in view of regional differences, the international research on bayberry has just started. At present, there are only many researches on myricetin contained in Guangxi rattan tea in China, while Zhejiang, as a large province of myrica rubra producing area, has few researches on the active ingredients of local specialty cash crop myrica rubra. The research on myricetin is relatively backward. Ningbo has a related pharmaceutical factory has begun to carry out preliminary development and application of bayberry, and strive to industrialize it. For example, the crude extract is used for food additives, separation and purification of active ingredients in the crude extract, and related pharmacological activity research, etc., so as to further accelerate the modernization of Chinese medicine in my country. |
| preparation method | mix dihydromyricetin with alcohols, then add sodium hypochlorite solution and catalyst, and continue to add sodium hypochlorite solution after the reaction is complete to obtain myricetin. In this method, the alcohol is methanol or ethanol, and the catalyst is anhydrous aluminum trichloride or anhydrous ferric chloride. This method uses dihydromyricin as the starting material, and the product is prepared by semi-synthesis. Because dihydromyricin is extracted from plant vine tea, the content is more than 98%, the cost is low, the operation is simple, the product yield is high, the product does not need to be refined, the content is more than 98%, and it is suitable for industrial production. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:12
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