cis-Resveratrol

• CAT Number: R007773
• CAS Number: 61434-67-1
• Molecular Formula: C14H12O3
• Molecular Weight: 228.247
• Purity: ≥95%
• Storage: -80°C
• IUPAC Name: 5-[(Z)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
• InChI: 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-
• InChIKey: LUKBXSAWLPMMSZ-UPHRSURJSA-N
• SMILES: C1=CC(=CC=C1C=CC2=CC(=CC(=C2)O)O)O

Resveratrol is a potent phenolic antioxidant found in grapes, red wine, and various berries that also has antiproliferative and anti-<wbr></wbr>inflammatory activity. cis-<wbr></wbr>Resveratrol is the double bond isomer of trans-<wbr></wbr>resveratrol, the more often studied and naturally abundant of the two resveratrol isomers. cis-<wbr></wbr>Resveratrol exhibits antioxidant activity in the µM range similar to that observed with trans-<wbr></wbr>resveratrol. It blocks production of reactive oxygen species (ROS) by inhibition of NAD(P)H oxidase and also inhibits production of nitric oxide. At a concentration of 100 µM, cis-<wbr></wbr>resveratrol significantly inhibits the expression of genes related to the Rel/NF-<wbr></wbr>κB/IκB family, adhesion molecules, and acute-<wbr></wbr>phase proteins in LPS and INF-<wbr></wbr>γ-<wbr></wbr>stimulated murine peritoneal macrophages. cis-<wbr></wbr>Resveratrol inhibits uptake of noradrenaline and 5-<wbr></wbr>HT by synaptosomes from rat brain with IC50 values of 79 and 51 µM, respectively. It also inhibits human monoamine oxidase-<wbr></wbr>A (MOA-<wbr></wbr>A) and MOA-<wbr></wbr>B with IC50 values of 25 and 61 µM, respectively, which is similar to, but slightly less effective than, values obtained with trans-<wbr></wbr>resveratrol.