R5010

Resveratrol

≥99% (HPLC)

• Synonym(s): 3,4′,5-Trihydroxy-trans-stilbene, 5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol
• Empirical Formula (Hill Notation): C₁₄H₁₂O₃
• CAS Number: 501-36-0
• Molecular Weight: 228.24
• MDL number: MFCD00133799
• UNSPSC Code: 12352205
• PubChem Substance ID: 24278055
• NACRES: NA.25

Properties

• biological source: plant root (bushy knotweed)
• Assay: ≥99% (HPLC)
• form: powder
• solubility: acetone: 50 mg/mL, clear, faintly yellow
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: −20°C
• SMILES string: Oc1ccc(cc1)\C=C\c2cc(O)cc(O)c2
• InChI: 1S/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+
• InChI key: LUKBXSAWLPMMSZ-OWOJBTEDSA-N
• Gene Information: human ... AR(367) , CYP1A2(1544) , ESR1(2099) , SIRT1(23411) ; mouse ... Nos2(18126) ; rat ... Esr1(24890)

Description

Application

Resveratrol has been used:

• in entrapment experiment
• to study its neuroprotective effect on retinal neuronal cell death mediated by diabetes-induced activation of Ca²⁺/calmodulin-dependent protein kinase II
• as a standard in the assessment of stilbene content in grapevine leaf by in vivo fluorometry

Selective inhibitor of COX−1.

Biochem/physiol Actions

Resveratrol is a phenolic phytoalexin found in grape skin and other plants. It has intracellular antioxidant activity and activates sirtuin 1 (SIRT1), a nicotinamide adenine dinucleotide (NAD⁺)-dependent histone deacetylase involved in mitochondrial biogenesis and the enhancement of peroxisome proliferator-g-activated receptor coactivator-1a (PGC-1a) and FOXO (forkhead box) activity. The anti-diabetic, neuroprotective and anti-adipogenic actions of resveratrol may be mediated via SIRT1 activation. Resveratrol has antiviral action against Herpes simplex virus-1 (HSV1) and HSV2. It also exhibits antitumor and phytoestrogenic biological activities. Resveratrol is known to prolong life in many species by mediating several physiological events.

Preparation Note

Soluble in ethanol, DMSO, and acetone. Only very slightly soluble in water (3 mg/100 mL).

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H319
• Precautionary Statements: P264 - P280 - P305 + P351 + P338 - P337 + P313
• Hazard Classifications: Eye Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): >392.0 °F - closed cup - (External MSDS)
• Flash Point(C): > 200.0 °C - closed cup - (External MSDS)
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves