resveratrol

resveratrol
Compound Structure:
Synonyms: resveratrol ;501-36-0 ;trans-resveratrol; 3,4',5-Trihydroxystilbene ;(E)-5-(4-Hydroxystyryl)benzene-1,3-diol
Compound ID: NMPC-1449
PubChem ID:

445154

Molecular Formula: C14H12O3
Canonical SMILES: C1=CC(=CC=C1C=CC2=CC(=CC(=C2)O)O)O
InChIKey: LUKBXSAWLPMMSZ-OWOJBTEDSA-N
About the compound:

Resveratrol is a stilbenol, specifically a 3,5,4'-trihydroxystilbene, known for being a naturally occurring polyphenolicphytoalexin. It is a derivative of stilbene, produced by plants via the enzyme stilbene synthase, especially in response to injury or attack by pathogens like bacteria or fungi. Resveratrol exists in two isomeric forms: cis-(Z) and trans-(E), with the trans-form being capable of isomerizing to the cis-form under heat or ultraviolet irradiation. This compound has a role as a phytoalexin, an antioxidant, a glioma-associated oncogene inhibitor, and a geroprotector. Found in high concentrations in red grapes, resveratrol is also present in blueberries, raspberries, mulberries, and peanuts. Despite its wide occurrence in nature and use as a dietary supplement, there is no high-quality evidence that resveratrol significantly impacts lifespan or effectively treats any human diseases. In terms of potential health benefits and therapeutic uses, research on resveratrol has explored various areas:

1. Cardiovascular Disease: There is no definitive evidence of benefit from resveratrol for individuals with heart disease. Some studies indicate a minor reduction in systolic blood pressure, particularly in diabetic individuals, at certain dosage levels.

2. Cancer: As of recent studies, there is no evidence that resveratrol impacts cancer in humans.

3. Metabolic Syndrome and Diabetes: The evidence for resveratrol's effect on metabolic syndrome is not conclusive. While some studies suggest a reduction in fasting plasma glucose in diabetic patients and potential weight reduction, the overall evidence is limited.

4. Cognition: Mixed evidence exists regarding resveratrol's impact on cognition. Some studies suggest improvements in recognition and mood, yet inconsistencies in study designs make definitive conclusions difficult.

5. Lifespan: Currently, there is insufficient evidence to suggest that resveratrol consumption affects human lifespan.

6. Other Areas: There is no significant evidence supporting the effect of resveratrol on various conditions, including vascular endothelial function, neuroinflammation, Alzheimer's disease, skin infections, aging skin, and certain bone biomarkers.

Despite its popularity and the promising results from animal studies, the benefits of resveratrol in human health remain uncertain due to the lack of substantial evidence from human studies. Consequently, while it continues to be a topic of interest for research, its use for specific health benefits should be approached with caution.

https://en.wikipedia.org/wiki/Resveratrol

GHS Hazard Statements

H315 (13.16%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (90.13%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (13.82%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

228.24 g/mol

XLogP3-AA

3.1

Hydrogen Bond Donor Count

3

Hydrogen Bond Acceptor Count

3

Rotatable Bond Count

2

Exact Mass

228.078644241 g/mol

Monoisotopic Mass

228.078644241 g/mol

Topological Polar Surface Area

60.7Ų

Heavy Atom Count

17

Formal Charge

0

Complexity

246

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

1

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid

Melting Point

254°C

Source: PubChem

Source Species: Ficus thonningii
Talinum triangulare
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