trans-3,4,5-Trihydroxystilbene

trans-3,4,5-Trihydroxystilbene - Names and Identifiers

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

trans-3,4,5-Trihydroxystilbene - Physico-chemical Properties

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

trans-3,4,5-Trihydroxystilbene - Risk and Safety

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

trans-3,4,5-Trihydroxystilbene - Introduction

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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.

Last Update：2022-01-01 08:48:33

trans-3,4,5-Trihydroxystilbene - Introduction

Pharmacological effects: It is a natural antioxidant that can reduce blood viscosity, inhibit platelet coagulation and vasodilation, keep blood unblocked, can prevent the occurrence and development of cancer, and has anti-atherosclerosis and coronary heart disease, Ischemic heart disease, prevention and treatment of hyperlipidemia. Tumor suppression also has an estrogen-like effect, which can be used to treat diseases such as breast cancer.

Last Update：2022-10-16 17:25:36

trans-3,4,5-Trihydroxystilbene - Method for Determination of content

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Last Update：2022-01-01 08:48:34

trans-3,4,5-Trihydroxystilbene - Pharmacological action

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resveratrol is not only a chemopreventive agent for tumor diseases, but also a chemopreventive agent for reducing platelet aggregation, preventing and treating atherosclerosis and cardiovascular and cerebrovascular diseases. 90's of the 20th century, China's scientific and technological workers continue to deepen the study of resveratrol, and reveal its pharmacological effects: inhibition of abnormal platelet aggregation, prevention of myocardial congestion, cerebral embolism, has a protective effect on hypoxic heart, it can effectively recover the decrease of cardiac output caused by burn or hemorrhagic shock, dilate arterial blood vessels and improve microcirculation.
in 1998al Mindel, the United States, when he compiled the anti-aging classic, The resveratrol was listed as one of the "100 most effective anti-aging substances. Professor Mao Wenyue, a researcher at the Peanut Research Institute of the Chinese Academy of Agricultural Sciences and a famous national medical expert, said that peanuts (the content of protein and fat in Peanuts is higher than that of meat and eggs, and the ancient people called it "longevity fruit") the research and development of resveratrol will be one of the most important nutrition topics in the 21st century. So far, NASA has designated peanuts as space food, often eat peanut products, can alleviate cardiovascular disease, lower blood lipids, anti-aging. Peanut oil, peanut butter and other foods rich in resveratrol will become the 21st century nutrition and health of the new fashion. Resveratrol is not only a chemopreventive agent for tumor diseases, but also a chemopreventive agent for reducing platelet aggregation, preventing and treating atherosclerosis and cardiovascular and cerebrovascular diseases. Resveratrol had inhibitory effect on Staphylococcus aureus, catarrhal coccus, Escherichia coli, Pseudomonas aeruginosa, and had strong inhibitory effect on orphan Virus, Herpes Sinplex Virus Virus and intestinal Virus, Coxsackie a, B group.
in the 90 s of the 20th century, the research on resveratrol by Chinese scientific and technological workers has been deepened, and its pharmacological effects have been revealed: inhibiting abnormal platelet aggregation, preventing myocardial tamponade and cerebral embolism, and protecting the hypoxic heart, it can effectively recover the decrease of cardiac output caused by burn or hemorrhagic shock, dilate arterial blood vessels and improve microcirculation.

resveratrol is an anti-free radical, antioxidant, and its related functions are as follows

Anti-aging.
prevents the oxidation of low density lipoprotein, has a potential role in the prevention and treatment of cardiovascular diseases (atherosclerosis and coronary heart disease, ischemic heart disease, hyperlipidemia, etc.).
anti-thrombosis, anti-platelet aggregation.
Anti-inflammatory and anti-allergic effects.

Last Update：2022-01-01 08:48:35

trans-3,4,5-Trihydroxystilbene - Methods for artificial synthesis of resveratrol

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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.

Last Update：2022-01-01 08:48:36

trans-3,4,5-Trihydroxystilbene - Solubility

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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.

Last Update：2022-01-01 08:48:36

trans-3,4,5-Trihydroxystilbene - Toxic activity

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resveratrol's hormonal and genotoxic activity: experiments have shown that resveratrol-induced cytotoxicity, micronucleus and metaphase chromosome translocation can be observed in L5178Y mouse lymphoma. Micronucleus induction was also observed in Chinese hamster V79 cells. Centromere signaling of the micronuclei and cell cycle analysis suggest that resveratrol does not directly disrupt tubulin polymerization released by mitotic cells. Studies have shown that resveratrol has no direct effect on microtubule assembly.
mechanism of protecting mitochondrial function: some scholars have studied the isolation of mitochondria in rat brain tissue through the rat model of hypoxia-reoxygenation, it was found that resveratrol completely blocked the release of cytochrome C in a concentration-dependent manner, and significantly reduced the formation of oxide anions at the concentration of 1nmol. The mitochondrial protective membrane damage caused by hypoxia-reoxygenation is approximately 0.1 protected at a concentration of 70% micromolar of resveratrol. In the presence of NADH and cytochrome C, a low 50% effective concentration of 18.34PM of resveratrol can block the oxygen consumption of mitochondria.
three mechanisms of resveratrol protecting mitochondria: antioxidant properties, the role of complex III and cell membrane stabilization.
peripheral anti-pain effect: the results of the 1% formalin test showed that resveratrol opened large and small conductance Ca2 + activated potassium ion channels, instead of the ATP-sensitive K + channel, it produced an anti-pain effect in the experiment, proving that the anti-pain effect of resveratrol is related to the K + channel. Voltage-dependent K + channels may also be involved.

Last Update：2022-01-01 08:48:37

trans-3,4,5-Trihydroxystilbene - Chemical properties and uses

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chemical properties

tasteless, white powder, completely dissolved in ethanol.

purpose

it can prevent the oxidation of low density lipoprotein, and has the potential to prevent and treat cardiovascular disease, anti-cancer, anti-virus and immune regulation. Its main function is its antioxidant properties.
cardiovascular drugs, can reduce blood lipids, and can prevent heart disease, but also has the role of anti-AIDS
antioxidant, anti-inflammatory, anti-thrombosis, anti-cancer, anti-cancer, anti-hyperlipidemia, antibacterial and other activities
delay aging, regulate blood lipids, protect cardiovascular and cerebrovascular, anti-hepatitis

Last Update：2022-01-01 08:48:38

trans-3,4,5-Trihydroxystilbene - Safety Information

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dangerous goods Mark Xi
hazard code 37/38-41-36/38
safety instructions 26-39-37/39
WGK Germany 3
RTECS number CZ8987000
toxic substance Data 501-36-0(Hazardous Substances Data)

Last Update：2022-01-01 08:48:38

trans-3,4,5-Trihydroxystilbene - Preparation Method

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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.

Perkin reaction synthesis

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%.

heck reaction synthesis

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.

Wittig-Horner reaction synthesis

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%.

Last Update：2022-01-01 08:48:39

trans-3,4,5-Trihydroxystilbene - Main efficacy

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pharmacological action

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.

Anticancer effect

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.

Antioxidant effect

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.

Antibacterial effect

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.

Lipid-lowering effect

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.

Prevention of food allergy

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.

Anti-oxidative stress effect of resveratrol

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.

Last Update：2022-01-01 08:48:41

trans-3,4,5-Trihydroxystilbene - Related research

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in 1998al Mindel, the United States, when he compiled the anti-aging classic, The resveratrol was listed as one of the "100 most effective anti-aging substances.
Professor Mao Wenyue, a researcher at the Peanut Research Institute of the Chinese Academy of Agricultural Sciences and a famous national medical expert, believes that the protein and fat content of peanuts is higher than that of meat and eggs, the research and development of resveratrol in the ancient "long fruit" will be one of the most important nutrition topics in the 21st century.
NASA has designated peanuts as space food, often eat peanut products, can alleviate cardiovascular disease, reduce blood lipids, delay aging. Peanut oil, peanut butter and other foods rich in resveratrol will become the 21st century nutrition and health of the new fashion.
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 and cerebral embolism, and protecting the hypoxic heart, it can effectively recover the decrease of cardiac output caused by burn or hemorrhagic shock, dilate arterial blood vessels and improve microcirculation.
in September 2012, Japanese researchers found in animal experiments that resveratrol, which is rich in red wine, can prevent food allergy.
in November 2012, according to a study by the University of Toronto, Canada, smokers who drink a moderate amount of red wine can not only neutralize the toxins in cigarettes, but also eliminate a variety of toxic substances in the natural environment, reduced smoke hazard. Resveratrol in red wine can reduce the car exhaust and smoke produced by baking, red wine can remove toxins in the body of smokers.
in early, British pharmaceutical giant GlaxoSmithKline was testing new drugs that might extend life expectancy to 150 years. It has been reported that the components of these new drugs are synthetic resveratrol. Resveratrol, a polyphenolic compound found in red wine, has the effect of delaying aging by promoting the activity of SIRT1 histone deacetylase, known as the "longevity gene.
In 2015, according to foreign media reports, red wine to enjoy the name of "immortal medicine", and the discussion of some ingredients in red wine has not been stopped. resveratrol in red wine does make you live longer, but only at very small doses. If you consume too much, it will not slow down the rate of aging, on the contrary, it will accelerate aging.

Last Update：2022-01-01 08:48:41

trans-3,4,5-Trihydroxystilbene - Introduction

resveratrol is a compound naturally occurring in a variety of plants with the chemical name 3,5,4 '-trihydroxycinnamic acid. The following is a description of the nature, use, formulation and safety information of resveratrol:

1. Nature:
-Appearance: resveratrol is a colorless or yellowish acicular or crystalline powder.
-Solubility: The solubility in water is low, but it is soluble in some organic solvents, such as alcohols, esters and dimethylimide.
-Stability: resveratrol has certain stability to light, heat and acidic conditions.

2. Use:
-Antioxidant: resveratrol is an effective natural antioxidant that can neutralize free radicals and protect cells from oxidative stress.
-Anti-inflammatory and anti-cancer effects: resveratrol has anti-inflammatory and anti-cancer activities, which can inhibit inflammatory reactions and break through DNA damage caused by free radicals.
-Cardiovascular Protection: resveratrol lowers blood cholesterol and protects cardiovascular health.

3. Preparation method:
resveratrol can be extracted from a variety of plants, such as grape skin, pepper, Mulberry, etc. The extraction method is mainly to use a solvent (such as ethyl acetate, methanol) to heat and soak the plant material, and then obtain pure resveratrol through filtration, concentration and crystallization steps.

4. Safety Information:
resveratrol is generally considered safe, but it is still necessary to follow appropriate dosage and guidance when using it. Long-term high dose intake may have some negative effects on the kidneys, liver and digestive system. For pregnant women, lactating mothers and people with special or chronic diseases, it is recommended to consult a doctor before use. In addition, if allergic reactions or adverse symptoms occur with the use of resveratrol products, you should stop using them and seek medical help.

Last Update：2024-04-09 15:16:34