A resveratrol analog
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Oxyresveratrol

Item No. 12028

Technical Information
Formal Name
4-[(1E)-2-(3,5-dihydroxyphenyl)ethenyl]-1,3-benzenediol
CAS Number
29700-22-9
Synonyms
  • trans-2',3,4',5-Tetramethoxystilbene
Molecular Formula
C14H12O4
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): < 0.1 mg/ml
λmax
220, 302, 329 nm
SMILES
OC1=CC(O)=CC(/C=C/C2=C(O)C=C(O)C=C2)=C1
InChi Code
InChI=1S/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+
InChi Key
PDHAOJSHSJQANO-OWOJBTEDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Resveratrol is a potent phenolic antioxidant found in the skin of grapes and red wine that has anti-proliferative, anti-inflammatory, and cardioprotective properties.1 Oxyresveratrol is a naturally occurring analog of resveratrol found in mulberry wood. It effectively scavenges H2O2, NO (IC50 = 45.3 μM), and the artificial free radical 2,2-diphenyl-l-picrylhydrazyl (IC50 = 28.9 μM).2 At 10 mg/kg, oxyresveratrol acts as a neuroprotectant, reducing brain infarct volume and reducing cytochrome c release and caspase-3 activation in an in vivo model of stroke.3 Oxyresveratrol also has depigmenting effects by effectively inhibiting tyrosinase activity, which catalyzes the rate-limiting step in synthesizing melanin pigments (IC50s = 1.2 and 52.7 μM in mushroom and mouse melanoma B-16 cells, respectively).4 It is 32-fold more potent than kojic acid, a depigmenting agent used in cosmetic materials with skin-whitening effects and medical agents used to treat hyperpigmentation disorders.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rotondo, S., Rajtar, G., Manarini, S., et alEffect of trans-resveratrol, a natural polyphenolic compound, on human polymorphonuclear leukocyte function. Br. J. Pharmacol. 123(8), 1691-1699 (1998).

    2. Lorenz, P., Roychowdhury, S., Engelmann, M., et alOxyresveratrol and resveratrol are potent antioxidants and free radical scavengers: Effect on nitrosative and oxidative stress derived from microglial cells. Nitric Oxide 9(2), 64-76 (2003).

    3. Andrabi, S.A., Spina, M.G., Lorenz, P., et alOxyresveratrol (trans-2,3',4,5'-tetrahydroxystilbene) is neuroprotective and inhibits the apoptotic cell death in transient cerebral ischemia. Brain Res. 1017, 98-107 (2004).

    4. Kim, Y.M., Yun, J., Lee, C.K., et alOxyresveratrol and hydroxystilbene compounds. Inhbitory effect on tyrosinase and mechanism of action. The Journal of Biological Chemisty 277(18), 16340-16344 (2002).