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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:
501-36-0
Molecular Weight:
228.24
MDL number:
MFCD00133799
PubChem Substance ID:
24278055
NACRES:
NA.25

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)

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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.

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).

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

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

Certificates of Analysis (COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I dissolve Resveratrol, Product R5010?

    We test the solubility in ethanol at a concentration of 50 mg/mL.  It is also soluble at 16 mg/mL in DMSO (with sonication). It is practically insoluble in water.

  4. How do I store Resveratrol, Product R5010, once in solution?

    A 5 mM solution of R5010 in ethanol has been found to be stable for 12 weeks when stored at 2-8°C and protected from light.Given a molecular weight of 228.24, a 5 mM solution is approximately 1.1 mg/mL.Reference: D.M. Goldberg, et al., J. Chrom. A, 708, 89-98 (1995). 

  5. In what applications do researchers use Resveratrol, Product R5010?

    There are numerous applications for Resveratrol.  Several references indicate that it is used as a COX-1 inhibitor and a tumor repressor.

  6. Can Resveratrol, Product R5010, be used as a treatment for human patients?

    No. Unfortunately, none of our catalog items are suitable for pharmaceutical applications.  To inquire further on our ability to provide USP material please email our SAFC Pharma group at SAFCglobal@sial.com.

  7. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  8. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
Therapeutic potential of resveratrol: the in vivo evidence
Baur JA and Sinclair DA
Nature Reviews Drug Discovery, 5(6), 493-493 (2006)
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)
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)
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