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R5010

Sigma-Aldrich

Resveratrol

≥99% (HPLC)

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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

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

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This Item
76511Y0001194PHL89539
vibrant-m

R5010

Resveratrol

vibrant-m

76511

Resveratrol

vibrant-m

Y0001194

Resveratrol

vibrant-m

PHL89539

trans-Resveratrol

Quality Level

200

Quality Level

300

Quality Level

-

Quality Level

-

form

powder

form

-

form

-

form

-

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

food and beverages

application(s)

pharmaceutical (small molecule)

application(s)

food and beverages

biological source

plant root (bushy knotweed)

biological source

-

biological source

-

biological source

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

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).

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

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SRT1720 SRT1720, CAS 925434-55-5, is a cell-permeable inhibitor of the mitochondrial SIRT3. Inhibition is AceCS2-competitive (Ki = 0.56 µM; Km = 2.44 µM), but NAD+-uncompetitive (Ki = 0.34 µM; Km = 280 µM).

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Sigma-Aldrich

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Sirtinol

Fast and local assessment of stilbene content in grapevine leaf by in vivo fluorometry
Poutaraud A, et al.
Journal of Agricultural and Food Chemistry, 55(13), 4913-4920 (2007)
Resveratrol improves health and survival of mice on a high-calorie diet
Baur JA, et al.
Nature, 444(7117), 337-337 (2006)
Halloysite clay nanotubes for resveratrol delivery to cancer cells
Vergaro V, et al.
Macromolecular Bioscience, 12(9), 1265-1271 (2012)
Resveratrol inhibits neuronal apoptosis and elevated Ca2+/calmodulin-dependent protein kinase II activity in diabetic mouse retina
Kim YH, et al.
Diabetes, 59(7), 1825-1835 (2010)
Therapeutic potential of resveratrol: the in vivo evidence
Baur JA and Sinclair DA
Nature Reviews Drug Discovery, 5(6), 493-493 (2006)

Articles

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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