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R5010

Sigma-Aldrich

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:
Molecular Weight:
228.24
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

plant root (bushy knotweed)

Quality Level

assay

≥99% (HPLC)

form

powder

solubility

acetone: 50 mg/mL, clear, faintly yellow

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

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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.

Packaging

100, 500 mg in poly bottle

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).

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificate of Analysis

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Certificate of Origin

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