Oxyresveratrol

Names

[ Name ]:
Oxyresveratrol

[Synonym ]:
4-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,3-diol
Puag-haad
2,4,3',5'-Tetrahydroxystilbene
3,4,3',5'-tetrahydroxy-trans-stilbene
OXYLRESVERATROL
trans-oxyresveratrol
2,3',4,5'-Tetrahydroxy-trans-stilbene
(E)-4-(3,5-Dihydroxystyryl)benzene-1,3-diol
Oxyresveratrol
1,3-Benzenediol, 4-(2-(3,5-dihydroxyphenyl)ethenyl)-, (E)-
EINECS 300-008-4
2,3',4,5'-Tetrahydroxystilbene
4-[(E)-2-(3,5-Dihydroxyphenyl)vinyl]-1,3-benzenediol
trans-2,3',4,5'-tetrahydroxystilbene
4-[(E)-2-(3,5-Dihydroxyphenyl)vinyl]benzene-1,3-diol
1,3-Benzenediol, 4-(2-(3,5-dihydroxyphenyl)ethenyl)-
1,3-Benzenediol, 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-

Biological Activity

[Description]:

Oxyresveratrol is neuroprotective and inhibits the apoptotic cell death in transient cerebral ischemia. It effectively scavenges H2O2, NO (IC50 = 45.3 μM), and the artificial free radical 2,2-diphenyl-l-picrylhydrazyl (IC50 = 28.9 μM) In vitro: 1)oxyresveratrol exhibited more than 50% inhibition at 100 μM on L-tyrosine oxidation by murine tyrosinase activity.2) oxyresveratrol showed an IC50 value of 52.7 μM on the enzyme activity. 3) oxyresveratrol works through reversible inhibition of tyrosinase activity rather than suppression of the expression and synthesis of the enzyme.[2] In vivo: 1) Oxyresveratrol (10 or 20 mg/kg) significantly reduced the brain infarct volume by approximately 54% and 63%, respectively, when compared to vehicle-treated MCAO rats.2) oxyresveratrol treatment diminished cytochrome c release and decreasedcaspase-3 activation in MCAO rats. [3]

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> Tyrosinase

Research Areas >> Others

Natural Products >> Phenols

[References]

[1]. Lorenz. et al. Oxyresveratrol 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).

[2]. Kim, Y.M., Yun, J., Lee, C., et al. Oxyresveratrol and hydroxystilbene compounds. Inhbitory effect on tyrosinase and mechanism of action. J Biol Chem277(18) 16340-16344 (2002).

[3]. Shaida A Andrabi et al. Oxyresveratrol (trans-2,3′,4,5′-tetrahydroxystilbene) is neuroprotective and inhibits the apoptotic cell death in transient cerebral ischemia. Brain Res, 2004 Aug 13, 1017(1-2):98-107.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
523.8±30.0 °C at 760 mmHg

[ Melting Point ]:
201ºC

[ Molecular Formula ]:
C₁₄H₁₂O₄

[ Molecular Weight ]:
244.243

[ Flash Point ]:
260.8±19.2 °C

[ Exact Mass ]:
244.073563

[ PSA ]:
80.92000

[ LogP ]:
3.17

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.801

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36

[ Safety Phrases ]:
26