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Cat. Number
080341960298029
Chemical Name
trans
References
Synonyms
  • (E)-Resveratrol
Formal Name 5-​[(1E)-​2-​(4-​hydroxyphenyl)ethenyl]-​1,​3-​benzenediol
CAS Number 501-36-0
Molecular Formula C14H12O3
Formula Weight 228.2
Formulation A crystalline solid
Purity >98%
λmax 218, 307, 321 nm
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES Oc1ccc(cc1)​\C=C/c1cc(O)​cc(O)​c1

Background Reading

Jang, M., Cai, L., Udeani, G.O., et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275 218-220 (1997).

Frémont, L., Belguendouz, L., and Delpal, S. Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids. Life Sci 64 2511-2521 (1999).

Johnson, J.L., and Maddipati, K.R. Paradoxical effects of resveratrol on the two prostaglandin H synthases. Prostaglandins Other Lipid Mediat 56 131-143 (1998).

Rotondo, S., Rajtar, G., Manarini, S., et al. Effect of trans-resveratrol, a natural polyphenolic compound, on human polymorphonuclear leukocyte function. Br J Pharmacol 123 1691-1699 (1998).

Miller, N.J., and Rice-Evans, C. Antioxidant activity of resveratrol in red wine. Clin Chem 41 1789 (1995).

Borra, M.T., Smith, B.C., and Denu, J.M. Mechanism of human SIRT1 activation by resveratrol. J Biol Chem 280(17) 17187-17195 (2005).

Howitz, K.T., Bitterman, K.J., Cohen, H.Y., et al. Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan. Nature 425 191-196 (2003).

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Description

Phenolic compounds, particularly flavonoids, from plant sources have long been observed to have antioxidant activity with potential benefits for human health.1,2,3 trans-Resveratrol is a potent phenolic antioxidant found in grapes and red wine that also has antiproliferative and anti-inflammatory activity.4 trans-Resveratrol is also a selective inhibitor of cyclooxygenase-1 (COX-1).5 It inhibits COX and peroxidase activities of COX-1 with ED50 values of 15 and 3.7 µM, respectively; with essentially no inhibition of the COX activity of COX-2. Resveratrol also activates sirtuins6 and, in C. elegans, extends lifespan.7

1 Frémont, L., Belguendouz, L., and Delpal, S. Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids. Life Sci 64 2511-2521 (1999).

2 Johnson, J.L., and Maddipati, K.R. Paradoxical effects of resveratrol on the two prostaglandin H synthases. Prostaglandins Other Lipid Mediat 56 131-143 (1998).

3 Rotondo, S., Rajtar, G., Manarini, S., et al. Effect of trans-resveratrol, a natural polyphenolic compound, on human polymorphonuclear leukocyte function. Br J Pharmacol 123 1691-1699 (1998).

4 Miller, N.J., and Rice-Evans, C. Antioxidant activity of resveratrol in red wine. Clin Chem 41 1789 (1995).

5 Jang, M., Cai, L., Udeani, G.O., et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275 218-220 (1997).

6 Borra, M.T., Smith, B.C., and Denu, J.M. Mechanism of human SIRT1 activation by resveratrol. J Biol Chem 280(17) 17187-17195 (2005).

7 Howitz, K.T., Bitterman, K.J., Cohen, H.Y., et al. Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan. Nature 425 191-196 (2003).

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