Name | resveratrol |
Synonyms | RESVERATROL Resveratrol resveratrol RESVERATROLE TRANS-RESVERATROL Veratrum album L alcohol TRANS-3,5,4'-STILBENETRIOL TRANS-3,4,5-TRIHYDROXYSTILBENE trans-3,4,5-Trihydroxystilbene 3,4',5-Trihydroxy-trans-stilbene 3,4',5-TRIHYDROXY-TRANS-STILBENE 3,4',5'-TRIHYDROXY-TRANS-STILBENE TRANS-1,2-(3,4',5-TRIHYDROXYDIPHENYL)ETHYLENE 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol 5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol |
CAS | 501-36-0 |
EINECS | 610-504-8 |
InChI | InChI=1/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+ |
InChIKey | LUKBXSAWLPMMSZ-OWOJBTEDSA-N |
Molecular Formula | C14H12O3 |
Molar Mass | 228.24 |
Density | 1.359±0.06 g/cm3(Predicted) |
Melting Point | 253-255°C |
Boling Point | 449.1±14.0 °C(Predicted) |
Flash Point | 222.3°C |
Water Solubility | Soluble in water (3 mg/100mL), ethanol (50 mg/mL), DMSO (16 mg/mL), DMF (~65 mg/mL), PBS (pH 7.2) (~100µg/mL), methanol, and acetone (50 mg/mL). |
Solubility | Insoluble in water, soluble in ethanol, acetone and other organic solvents. |
Vapor Presure | 1.11E-08mmHg at 25°C |
Appearance | Colorless needle crystal |
Color | Off-white |
Merck | 14,8158 |
pKa | 9.22±0.10(Predicted) |
Storage Condition | -20°C |
Stability | Stable for 2 years as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. |
Refractive Index | 1.762 |
MDL | MFCD00133799 |
Physical and Chemical Properties | Odorless, white powder, completely dissolved in ethanol. |
Use | Cardiovascular drugs, can reduce blood lipids, and can prevent heart disease, but also has the role of anti-AIDS |
Hazard Symbols | Xi - Irritant |
Risk Codes | R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R36/38 - Irritating to eyes and skin. R36 - Irritating to the eyes R43 - May cause sensitization by skin contact R22 - Harmful if swallowed |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S37/39 - Wear suitable gloves and eye/face protection S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
WGK Germany | 3 |
RTECS | CZ8987000 |
HS Code | 29072990 |
resveratrol is a natural antioxidant, can reduce blood viscosity, inhibit platelet aggregation and vasodilation, maintain blood flow, can prevent the occurrence and development of cancer, has anti-atherosclerosis and coronary heart disease, ischemic heart disease, prevention and treatment of hyperlipidemia. Inhibition of tumor also has estrogen-like effect, can be used for the treatment of breast cancer and other diseases. Can delay aging, prevent cancer, in the red grape skin, red wine and grape juice in high content. Studies have shown that the integrity of the chromosome will be destroyed with the aging of human beings, and resveratrol can activate a protein sirtuin to repair the health of the chromosome, thus playing a role in delaying aging.
resveratrol is a natural antioxidant, can reduce blood viscosity, inhibit platelet aggregation and vasodilation, maintain blood flow, can prevent the occurrence and development of cancer, has anti-atherosclerosis and coronary heart disease, ischemic heart disease, prevention and treatment of hyperlipidemia. Inhibition of tumor also has estrogen-like effect, can be used for the treatment of breast cancer and other diseases. Can delay aging, prevent cancer, in the red grape skin, red wine and grape juice in high content. Studies have shown that the integrity of the chromosome will be destroyed with the aging of human beings, and resveratrol can activate a protein sirtuin to repair the health of the chromosome, thus playing a role in delaying aging.
resveratrol is an inhibitor of the oxidative metabolism enzymes of many aromatic carcinogens and is rated as a natural chemopreventive agent for cardiovascular and cerebrovascular diseases and cancer. A large number of studies have shown that resveratrol also has anti-mutation activity, protection of oxidative lipoprotein induced cell toxicity, inhibition of tumor cell proliferation and other functions.
Resveratrol was isolated from the root of Veratrum grandiflorum for the first time in human beings in 1940. It has been found in at least 72 species of 21 families and 31 genera, such as the grape genus of the grape family, ampelopsis, leguminous groundnut, Cassia, Sophora, Polygonaceae, etc. Because the content of resveratrol in plants is very low and the extraction cost is high, the use of chemical, biological, genetic engineering and other methods to prepare resveratrol has become an indispensable means in the development process.
resveratrol is a naturally occurring grape and red wine, Mulberry, peanuts and Polygonum cuspidatum antioxidants, belonging to the polyphenols, soluble in organic solvents, insoluble in water, the order of dissolution in the organic solvent species is: acetone> ethanol> methanol> ethyl acetate> ether> chloroform.
tasteless, white powder, completely dissolved in ethanol.
resveratrol is in great demand in the market. Due to its low content in plants and high extraction cost, chemical synthesis of resveratrol has become the main means of its development.
using 3, 5-diisopropoxybenzaldehyde and p-isopropoxyphenylacetic acid as raw materials, a single cis intermediate was synthesized by Perkin reaction, and then converted into a single trans-resveratrol, the yield was 55.2%.
single trans-resveratrol was synthesized by Heck reaction, and the yield reached more than 70%, but the key intermediate 3,5-diacetoxy styrene needed to be protected, Wittig reaction, protection of the three-step reaction can be obtained.
zhuoguanglan, etc. to 3,5 dihydroxybenzoic acid as raw material, by methylation, hydrazine, oxidation reaction to obtain intermediate 3,5 dimethoxybenzaldehyde, A single trans 3,4 ',5 trimethoxystilbene was obtained by Wittig-Homer condensation reaction with P-methoxybenzyl phosphate, and finally the methyl protecting group was removed by BBr3/CH2C: to synthesize resveratrol with a yield of 35.7%.
resveratrol is a chemopreventive agent for tumor diseases, and also a chemopreventive agent for reducing platelet aggregation, preventing and treating atherosclerosis and cardiovascular and cerebrovascular diseases. In the 90's of the 20th century, Chinese scientific and technological workers continued to deepen their research on resveratrol, and revealed its pharmacological effects: inhibiting abnormal platelet aggregation, preventing myocardial tamponade, cerebral embolism, and protecting the heart from hypoxia, it can effectively recover the decrease of cardiac output caused by burn or hemorrhagic shock, dilate arterial blood vessels and improve microcirculation.
both trans-resveratrol and cis-resveratrol have anti-cancer activity because they inhibit the activity of protein-tyrosine kinases. Resveratrol has high anti-cancer activity in the three stages of cancer initiation, promotion and development, and has inhibitory and even reversing effects on the three stages of cancer occurrence: first, inhibition of the initial effect. Reduce the formation of free radicals, induce the increase of the second phase of the drug, and antagonize the effect of dioxin; Second, inhibit the promotion. Inhibition of cyclooxygenase (COX ), inhibition of catalase; Three inhibitory effects on development. Inhibit cancer cell proliferation, induce cancer cell differentiation, induce cancer cell apoptosis. Resveratrol is expected to be an inhibitor of PTK. Many medical studies have found that resveratrol has obvious inhibitory effect on breast cancer, gastric cancer, colon cancer, prostate cancer, leukemia, ovarian cancer, skin cancer and other malignant tumor cells.
resveratrol is a natural antioxidant existing in plants. It plays an antioxidant role mainly by scavenging or inhibiting free radical generation, inhibiting lipid peroxidation, regulating antioxidant related enzyme activity and other mechanisms. When the concentration of resveratrol was 1.3 μg /mL, it could obviously inhibit the auto-oxidative hemolysis of rat red blood cells and the oxidative hemolysis caused by H2O2, the production of lipid peroxides in the kidney was significantly inhibited in vitro and in vivo. The pharmacological functions of resveratrol such as antioxidation, inducing free radicals and affecting the metabolism of arachidonic acid have aroused widespread interest, because these physiological metabolism are involved in many physiological diseases closely related to human health, such as atherosclerosis, Alzheimer's disease, viral hepatitis, gastric ulcer, inflammation and allergic reactions.
resveratrol has inhibitory effect on Staphylococcus aureus, catarrhal bacteria, Escherichia coli, Pseudomonas aeruginosa, and on orphans Virus, Herpes Sinplex Virus Virus and intestinal Virus and Coxsackie A, B group had a strong inhibitory effect. Resveratrol by reducing platelet adhesion, in the anti-inflammatory process to change the activity of platelets to achieve anti-inflammatory.
because resveratrol has anti-cancer, antioxidant, anti-inflammatory, anti-bacterial effects and love people's love, plant sources said because the French people often drink high fat containing resveratrol, so the French people of coronary heart disease by the end Incidence Rate in other Western countries, from this information can be learned because of resveratrol effectively suppress the prevention and treatment of high fat.
in some people, the body's immune system causes an allergic reaction to foods such as eggs, wheat and milk, which in severe cases can lead to Shock deaths. Japanese researchers have found in animal experiments that resveratrol, which is rich in red wine, can prevent this food allergy.
oxidative stress plays an important role in the development of diabetic nephropathy, and a variety of antioxidants can delay the development of DN. Resveratrol can protect against oxidative stress, thereby improving the symptoms of early DN. Resveratrol has obvious anti-oxidative stress effect, can avoid high glucose, high fat induced oxidative stress injury, which plays an important role in the prevention and treatment of diabetes and its chronic complications, especially in the early stage of diabetes delay the development of DN, protect the kidney tissue. However, although resveratrol is a natural drug with great potential, the related research is limited to animal experiments and cellular and molecular levels, and its clinical application is relatively small.