RESVERATROL

Resveratrol is a natural polyphenolic compound commonly found in the skin of grapes, berries, peanuts, and red wine. 
Resveratrol is a type of stilbene, chemically classified as a 3,5,4'-trihydroxystilbene, with antioxidant properties that protect plants from environmental stressors.
Resveratrol is a stilbenoid, a type of natural phenol or polyphenol and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi.

CAS Number: 947686-05-7
Molecular Formula: C36H36O4
Molecular Weight: 532.68
EINECS Number: 943-705-7

Synonyms:resveratrol, 501-36-0, trans-resveratrol, 3,4',5-Trihydroxystilbene, (E)-5-(4-Hydroxystyryl)benzene-1,3-diol, 3,5,4'-Trihydroxystilbene, (E)-resveratrol, Resvida, 3,4',5-Stilbenetriol, 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol, 3,4',5-Trihydroxy-trans-stilbene, Biofort, Cuspidatin, 5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol, SRT-501, (E)-5-(p-Hydroxystyryl)resorcinol, Resveratrol p 5, SRT501, SRT 501, Resveratrol(e)-form, 3,5,4'-Trihydroxy-trans-stilbene, Melinjo resveratrol 20, CHEBI:45713, Srt 501m, trans-3,4',5-trihydroxystilbene, 5-[(E)-2-(4-hydroxyphenyl)vinyl]benzene-1,3-diol, NSC 327430, NSC-327430, trans-1,2-(3,4',5-Trihydroxydiphenyl)ethylene, CCRIS 8952, 5-[2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol, DTXSID4031980, UNII-Q369O8926L, HSDB 7571, Resveratrol (Standard), 5-((1E)-2-(4-Hydroxyphenyl)ethenyl)-1,3-benzenediol, Ca 1201, C14H12O3, 1,3-Benzenediol, 5-(2-(4-hydroxyphenyl)ethenyl)-, (E)-, 1,3-Benzenediol, 5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-, BIA 6-512, BIA-6-512, NSC327430, CHEMBL165, Q369O8926L, (E)-5-[2-(4-hydroxyphenyl)ethenyl]-1,3-benzendiol, MLS000069735, 133294-37-8, DTXCID2011980, CHEBI:27881, trans-3,4',5 - trihydroxystilbene, MFCD00133799, SMR000058206, RESVERATROL (MART.), RESVERATROL [MART.], 1,3-Benzenediol, 5-((E)-2-(4-hydroxyphenyl)ethenyl)-, Resveratol, TRANS-RESVERATROL (USP-RS), TRANS-RESVERATROL [USP-RS], 5-((E)-2-(4-HYDROXYPHENYL)-ETHENYL) BENZENE-1,3 DIOL, trans Resveratrol, 3,4',5-trihydroxy-stilbene, Resveratrol, natural, 5-(2-(4-hydroxyphenyl)ethenyl)benzene-1,3-diol, SR-01000000163, 5-((E)-2-(4-hydroxyphenyl)vinyl)benzene-1,3-diol, 1,3-Benzenediol, 5-[(E)-2-(4-hydroxyphenyl)ethenyl]-, Jotrol, 3fts, 4jaz, 4qer, Resveratrol, E-, Resveratrol,(S), KUC104385N, Stilbene, 2f, TaxusChinensisiRehd, NCGC00015894-02, CAS-501-36-0, STL, Prestwick_619, Resveratrol, trans-, (E)-5-(2-(4-hydroxyphenyl)ethenyl)-1,3-benzenediol, KSC-10-164, Resveratrol, synthetic, RM-1812, Opera_ID_586, RESVERATROL [MI], Prestwick2_000508, Prestwick3_000508, Spectrum5_000552, RESVERATROL [HSDB], R 5010, RESVERATROL [VANDF], 1,3-Benzenediol, 5-[(1Z)-2-(4-hydroxyphenyl)ethenyl]-, Lopac0_001111, REGID_for_CID_6240, SCHEMBL19425, BSPBio_000435, BSPBio_001114, BSPBio_003461, RESVERATROL [WHO-DD], MLS001055357, MLS001076538, MLS001424228, MLS002207121, MLS002222231, SPECTRUM1502223, CU-01000001503-3, BPBio1_000479, cid_445154, GTPL8741, SGCUT00007, Resveratrol, analytical standard, REGID_for_CID_445154, BDBM23926, Resveratrol, >=99% (HPLC), AMY5760, 2l98, BCPP000091, HMS1362H15, HMS1569F17, HMS1792H15, HMS1921N04, HMS1990H15, HMS2052I09, HMS2096F17, HMS2232A18, HMS3263O04, HMS3403H15, HMS3412O14, HMS3649A20, HMS3676O14, BCP01416, to_000079, Tox21_110257, Tox21_201374, Tox21_303376, Tox21_501111, AC-727, BBL028252, CCG-38874, HB4055, HY-16561R, LMPK13090005, s1396, STL146386, AKOS005720936, Tox21_110257_1, CS-1050, DB02709, KS-5047, LP01111, NC00349, SDCCGMLS-0002998.P003, SDCCGSBI-0051080.P003, IDI1_002152, NCGC00017352-05, NCGC00017352-06, NCGC00017352-07, NCGC00017352-08, NCGC00017352-09, NCGC00017352-10, NCGC00017352-11, NCGC00017352-12, NCGC00017352-13, NCGC00017352-14, NCGC00017352-15, NCGC00017352-16, NCGC00017352-17, NCGC00017352-18, NCGC00017352-19, NCGC00017352-24, NCGC00017352-31, NCGC00017352-37, NCGC00017352-39, NCGC00024003-00, NCGC00024003-04, NCGC00024003-05, NCGC00024003-06, NCGC00024003-07, NCGC00024003-08, NCGC00024003-09, NCGC00024003-10, NCGC00024003-11, NCGC00024003-12, NCGC00024003-13, NCGC00024003-14, NCGC00257465-01, NCGC00258925-01, NCGC00261796-01, trans-Resveratrol, SRT 501, 1ST40018, AS-12413, HY-16561, CS-0694771, EU-0101111, R0071, Resveratrol, Vetec(TM) reagent grade, 98%, SW196786-4, trans [2,5,4'-trihydroxydiphenyl] ethylene, C03582, N88795, 5-[2-(4-hydroxyphenyl)vinyl]-1,3-benzenediol, AB00052942-29, AB00052942_31, trans-Resveratrol 100 microg/mL in Acetonitrile, A827984, Q407329, 5-[(E)-2-(4-Hydroxyphenyl)vinyl]-1,3-benzoldiol, SR-01000000163-3, SR-01000000163-4, SR-01000000163-9, 5-[(E)-2-(4-Hydroxyphenyl)ethenyl]benzol-1,3-diol, 5-[(E)-2-(4-Hydroxyphenyl)vinyl]-1,3-benzenediol, 5[(E)-2-(4-Hydroxyphenyl)-vinyl]benzene 1,3-diol, BRD-K25591257-001-01-2, BRD-K80738081-001-06-2, BRD-K80738081-001-07-0, BRD-K80738081-001-09- Reaction mass of 3',5-diallyl[biphenyl]-2,4'-diol and 5,5'-diallyl[biphenyl]-2,2'-diol;3',5-(5,5'-)Diallyl-[1,1'-biphenyl]-2,4'-(2,2'-)diol;3',5-(5,5'-)Diallyl-[1,1'-biphenyl]-2,4'-(2,2'-)diol

Resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts.
Although commonly used as a dietary supplement and studied in laboratory models of human diseases, there is no high-quality evidence that resveratrol improves lifespan or has a substantial effect on any human disease.
Resveratrol has been studied for its potential therapeutic use, with little evidence of anti-disease effects or health benefits in humans.

There is no evidence of benefit from Resveratrol in people who already have heart disease.
Resveratrol a 2018 meta-analysis found no effect on systolic or diastolic blood pressure; a sub-analysis revealed a 2 mmHg decrease in systolic pressure only from resveratrol doses of 300 mg per day, and only in diabetic people.
A 2014 Chinese meta-analysis found no effect on systolic or diastolic blood pressure; a sub-analysis found an 11.90 mmHg reduction in systolic blood pressure from resveratrol doses of 150 mg per day.

There is no conclusive evidence for an effect of resveratrol on human metabolic syndrome.
One 2015 review found little evidence for use of resveratrol to treat diabetes.
A 2015 meta-analysis found little evidence for an effect of resveratrol on diabetes biomarkers.

One review found limited evidence that resveratrol lowered fasting plasma glucose in people with diabetes.
Two reviews indicated that resveratrol supplementation may reduce body weight and body mass index, but not fat mass or total blood cholesterol.
Resveratrol a 2018 review found that resveratrol supplementation may reduce biomarkers of inflammation, TNF-α and C-reactive protein.

Resveratrol has been assessed for a possible effect on cognition, but with mixed evidence for an effect. 
One review concluded that resveratrol had no effect on neurological function, but reported that supplementation improved recognition and mood, although there were inconsistencies in study designs and results.
Resveratrol has been identified as a pan-assay interference compound, which produces positive results in many different laboratory assays.

Resveratrols ability for varied interactions may be due to direct effects on cell membranes.
As of 2015, many specific biological targets for resveratrol had been identified, including NQO2 (alone and in interaction with AKT1), GSTP1, estrogen receptor beta, CBR1, and integrin αVβ. 
Resveratrol was unclear at that time if any or all of these were responsible for the observed effects in cells and model organisms.

The viability of an oral delivery method is unlikely due to the low aqueous solubility of the molecule. 
The bioavailability of resveratrol is about 0.5% due to extensive hepatic glucuronidation and sulfation.
Resveratrol occurs in the intestine as well as in the liver, whereas sulfonation not only occurs in the liver but in the intestine and by microbial gut activity.

Due to rapid metabolism, the half-life of resveratrol is short (about 8–14 minutes), but the half-life of the sulphate and glucoronide metabolites is above 9 hours.
Resveratrol is extensively metabolized in the body, with the liver and intestines as the major sites of its metabolism.
Liver metabolites are products of phase II (conjugation) enzymes, which are themselves induced by resveratrol in vitro.

Resveratrol (3,5,4'-trihydroxystilbene) is a stilbenoid, a derivative of stilbene.
Resveratrol exists as two geometric isomers: cis- (Z) and trans- (E), with the trans-isomer shown in the top image. 
Resveratrol exists conjugated to glucose.

The trans- form can undergo photoisomerization to the cis- form when exposed to ultraviolet irradiation.
Resveratrol protects cells from damage caused by free radicals.
Anti-inflammatory – May reduce inflammation, which is linked to several chronic diseases.

Resveratrol associated with improving heart health by lowering blood pressure and preventing arterial damage.
Resveratrol may mimic the benefits of calorie restriction, linked to longevity.
Resveratrol suggested to inhibit the growth of certain cancer cells.

Potential to protect nerve cells from damage and improve cognitive function.
May help regulate blood sugar levels.
UV irradiation to cis-resveratrol induces further photochemical reaction, producing a fluorescent molecule named "Resveratrone".

Resveratrol in the powder form was found to be stable under "accelerated stability" conditions of 75% humidity and 40 °C in the presence of air.
The trans isomer is also stabilized by the presence of transport proteins.
Resveratrol content also was stable in the skins of grapes and pomace taken after fermentation and stored for a long period.

Resveratrol data for the four most common forms of resveratrols are reported in literature.
Resveratrol is produced in plants via the enzyme resveratrol synthase (stilbene synthase).
Its immediate precursor is a tetraketide derived from malonyl CoA and 4-coumaroyl CoA.

The latter is derived from phenylalanine.
The grapevine fungal pathogen Botrytis cinerea is able to oxidise resveratrol into metabolites showing attenuated antifungal activities. 
Those include the resveratrol dimers restrytisol A, B, and C, resveratrol trans-dehydrodimer, leachinol F, and pallidol.

The soil bacterium Bacillus cereus can be used to transform resveratrol into piceid (resveratrol 3-O-beta-D-glucoside).
Only a few human studies have been done to determine the adverse effects of resveratrol, all of them preliminary with small participant numbers. 
Adverse effects resulted mainly from long-term use (weeks or longer) and daily doses of 1000 mg or higher, causing nausea, stomach pain, flatulence, and diarrhea.

Resveratrol a review of 136 patients in seven studies who were given more than 500 mg for a month showed 25 cases of diarrhea, 8 cases of abdominal pain, 7 cases of nausea, and 5 cases of flatulence.
Resveratrol effects on blood pressure found that some people had increased frequency of bowel movements and loose stools.
Resveratrol neutralizes free radicals, which are unstable molecules that can cause oxidative stress, leading to cellular damage. 

This damage is implicated in aging and diseases like cancer, heart disease, and neurodegenerative disorders. 
Its potent antioxidant properties contribute to cell protection and tissue repair.
Resveratrol is widely known for its role in promoting heart health, which is one reason it's associated with the "French Paradox" (the observation that French people have a relatively low incidence of heart disease despite consuming a diet rich in saturated fats). 

Improving blood flow and reducing blood pressure by stimulating the production of nitric oxide, a molecule that relaxes blood vessels.
Preventing the oxidation of LDL Resveratrol, a key factor in the development of atherosclerosis (plaque buildup in the arteries).
Inhibiting platelet aggregation, reducing the risk of blood clots.

Boiling point: 400℃ at 1.013hPa
Density: 1.15 at 20℃
vapor pressure:0.001-0.002Pa at 30-45℃
form: Solid
LogP: 4.24 at 25℃ and pH7

Resveratrol is a chemical mostly found in red grapes and products made from these grapes (wine, juice). 
Resveratrol may be helpful for hay fever and weight loss.
Resveratrol might have many effects in the body, including expanding blood vessels and reducing blood clotting. 

Resveratrol may also decrease pain and swelling, reduce levels of sugar in the blood, and help the body fight against disease.
Resveratrol is most commonly used for high cholesterol, cancer, heart disease, and many other conditions. 
But there is no strong evidence to support resveratrol for any use.

Resveratrol is a phytoalexin, a class of compounds produced by many plants when they are infected by pathogens or physically harmed by cutting, crushing, or ultraviolet radiation.
Plants that synthesize resveratrol include knotweeds, pine trees including Scots pine and Eastern white pine, grape vines, raspberries, mulberries, peanut plants, cocoa bushes, and Vaccinium shrubs that produce berries, including blueberries, cranberries, and bilberries.

Resveratrol concentrations in red wines average 1.9±1.7 mg trans-resveratrol/L (8.2±7.5 μM), ranging from nondetectable levels to 14.3 mg/L (62.7 μM) trans-resveratrol. 
Levels of cis-resveratrol follow the same trend as trans-resveratrol.
In general, wines made from grapes of the Pinot noir and St. Laurent varieties showed the highest level of trans-resveratrol, though no wine or region can yet be said to produce wines with significantly higher concentrations than any other wine or region.

Champagne and vinegar also contain appreciable levels of resveratrol.
Red wine contains between 0.2 and 5.8 mg/L, depending on the grape variety. 
White wine has much less because red wine is fermented with the skins, allowing the wine to extract the resveratrol, whereas white wine is fermented after the skin has been removed.

The composition of wine is different from that of grapes since the extraction of resveratrol from grapes depends on the duration of the skin contact, and the resveratrol 3-glucosides are in part hydrolysed, yielding both trans- and cis-resveratrol.
Resveratrol is a class of plant micronutrients called polyphenols. 
Polyphenols are organic chemicals that plants make to survive drought or attack from disease. 

Resveratrols are found in plant foods and have a variety of health benefits.
Resveratrol is found in peanuts, berries, and grapes. 
It is also found in red wine in higher amounts. 

Resveratrol has antioxidant and anti-inflammatory properties to protect you against diseases like cancer, diabetes, and Alzheimer’s disease.
The anti-inflammatory effects of resveratrol make it a good remedy for arthritis, and skin inflammation. 
Also, resveratrol has antibacterial and antifungal properties that help treat infections of the urinary and digestive tracts.

Resveratrol is a compound that belongs to a group of polyphenols called stilbenoids.
Resveratrol consist of two phenol rings connected by an ethylene bridge.
Resveratrol is present in more than 70 plant species but primarily in the skin and seeds of red grapes. 

It is also a phytoalexin, a protective antibiotic that plants produce when under stress. 
Resveratrol helps plants recover from fungal attacks, ultraviolet radiation, and other threatening circumstances.
Resveratrol has shown promising results in laboratory studies for its ability to slow the growth of cancer cells and induce apoptosis (programmed cell death). 

Resveratrol affects various stages of cancer development, including initiation, promotion, and progression. 
While most studies are preclinical, involving cancer types like breast, prostate, and colon, more research is needed to confirm these effects in humans.
Research suggests resveratrol may help protect the brain and nervous system from damage, possibly preventing or slowing neurodegenerative diseases like Alzheimer's and Parkinson's. 

Resveratrol has been shown to reduce amyloid plaque buildup (a hallmark of Alzheimer's) and may improve cognitive function due to its anti-inflammatory and antioxidant effects.
Resveratrol may improve insulin sensitivity and help regulate glucose metabolism, making it a potential aid in diabetes management. 
It may also help reduce complications associated with diabetes, such as nerve and kidney damage, by reducing oxidative stress.

Chronic inflammation plays a key role in the development of many diseases, including heart disease, cancer, and arthritis. 
Resveratrol has been shown to inhibit inflammatory enzymes and pathways, potentially reducing inflammation at a molecular level.
Resveratrol is believed to activate sirtuins, a family of proteins linked to aging and longevity. 

In some studies, it mimics the effects of calorie restriction, which has been shown to extend lifespan in various organisms. 
Its anti-aging potential has made it a popular ingredient in skin care products to reduce wrinkles and improve skin elasticity.

Resveratrol exhibits estrogenic activity, meaning it can bind to estrogen receptors and may have effects on hormone-related conditions. 
This has led to research into its role in managing symptoms of menopause and protecting against estrogen-related cancers, such as breast cancer.

Uses:
Resveratrol supplements are popular for promoting cardiovascular health. 
Resveratrol may lower blood pressure, reduce cholesterol, and improve blood flow, supporting overall heart function.
Many people take resveratrol to slow the aging process due to its antioxidant and anti-inflammatory properties. 

Resveratrol's believed to support skin health and cellular repair.
Resveratrol has been suggested to help with weight loss or weight management by improving metabolism and fat oxidation.
Some studies indicate that resveratrol may improve endurance and physical performance by enhancing mitochondrial function, which produces energy in cells.

Resveratrol is commonly used in skincare for its ability to fight free radical damage, protect against UV radiation, and reduce signs of aging such as wrinkles and fine lines.
It helps in reducing inflammation and preventing oxidative stress, which can damage skin cells. 
Some products use it to repair sun damage and promote an even skin tone.

Resveratrol is studied for its potential role in cancer prevention and treatment. 
Resveratrol's believed to inhibit cancer cell growth and proliferation, particularly in cancers like breast, colon, and prostate.
While it’s not a treatment, Resveratrol is being explored in conjunction with other therapies for its ability to sensitize cancer cells to chemotherapy.

Due to its neuroprotective properties, resveratrol is studied for preventing or delaying neurodegenerative diseases, such as Alzheimer's and Parkinson's.
Some research suggests resveratrol can improve cognitive function and memory in older adults, potentially helping with conditions like mild cognitive impairment.
Resveratrol may help manage blood sugar levels and improve insulin sensitivity, making it useful for individuals with type 2 diabetes or metabolic syndrome.

Resveratrol is believed to reduce the risk of complications from diabetes by protecting blood vessels and nerves.
Due to its ability to inhibit inflammatory pathways, resveratrol may be used for conditions characterized by chronic inflammation, such as arthritis or other inflammatory disorders.
It may also help reduce pain, particularly in conditions like osteoarthritis, due to its anti-inflammatory action.

Resveratrol is sometimes used as part of weight loss programs or supplements because of its potential to activate sirtuins, enzymes linked to metabolism and fat regulation. 
Resveratrol may also help increase fat oxidation, leading to weight loss.
In scientific research, resveratrol is being studied for its ability to extend lifespan by mimicking the effects of caloric restriction, which has been linked to increased longevity in various organisms.

In the fitness industry, resveratrol is included in some supplements aimed at improving physical performance, endurance, and recovery due to its positive effects on cellular energy production and reducing oxidative stress from intense exercise.
Resveratrol has mild estrogenic effects, which may make it useful in hormone-related conditions such as menopause. 

It could help alleviate symptoms like hot flashes or mood swings.
The compound is one of the main reasons red wine is thought to have heart-protective effects, especially in moderate amounts. 
Resveratrol supplements may provide these benefits without alcohol consumption.

Safety Profile:
Resveratrol has a blood-thinning effect similar to aspirin. 
This can increase the risk of bleeding, especially for people who are on blood-thinning medications like warfarin, aspirin, or other anticoagulants.
People undergoing surgery should avoid resveratrol supplements due to the increased risk of bleeding.

Resveratrol may lower blood pressure, which can be dangerous for individuals taking antihypertensive drugs, as it could lead to excessively low blood pressure (hypotension).
Resveratrol may affect blood sugar levels, which could interfere with medications for diabetes, potentially leading to hypoglycemia (low blood sugar).
Because resveratrol has mild estrogenic activity, it might interfere with hormone therapies or worsen conditions like breast cancer, uterine fibroids, or endometriosis.

Some individuals may experience allergic reactions to resveratrol, such as skin rashes, itching, or respiratory issues. 
People with known allergies to grapes or red wine should be cautious.