5-[2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol

• ChemBase ID: 2432
• Molecular Formular: C14H12O3
• Molecular Mass: 228.24328
• Monoisotopic Mass: 228.07864424
• SMILES: Oc1ccc(cc1)/C=C/c1cc(O)cc(O)c1
• Canonical SMILES: Oc1ccc(cc1)/C=C/c1cc(O)cc(c1)O
• 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-OWOJBTEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol; 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
• IUPAC Traditional name: 3,5,4'-trihydroxystilbene; 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol; resveratrol
• Synonyms: Resveratrol; trans-3,5,4'-Trihydroxystilbene3,4',5-Stilbenetrioltrans-Resveratrol(E)-5-(p-Hydroxystyryl)resorcinol(E)-5-(4-hydroxystyryl)benzene-1,3-diol; trans-Resveratrol; 3,4',5-Trihydroxy-trans-stilbene; trans-Stilbene-3,4',5-triol; 5-[(E)-2-(4-Hydroxyphenyl)ethenyl]benzene-1,3-diol; 5-[(E)-2-(4-Hydroxyphenyl)vinyl]benzene-1,3-diol; trans-3,4',5-trihydroxystilbene; (E)-5-(2-(4-hydroxyphenyl)ethenyl)-1,3-benzenediol; (E)-5-(p-Hydroxystyryl)resorcinol; (E)-5-[2-(4-hydroxyphenyl)ethenyl]-1,3-benzendiol; (E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol; (E)-resveratrol; 3,4',5-Stilbenetriol; 3,4',5-trihydroxy-stilbene; 3,4',5-Trihydroxystilbene; resveratrol; Resveratrol; (E)-5-(4-Hydroxystyryl)benzene-1,3-diol; trans-3,4',5-Trihydroxystilbene; 3,4′,5-Trihydroxy-trans-stilbene; 5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol; 3,4′,5-三羟基-反式-二苯乙烯; 5-[(1E)-2-(4-羟苯基)乙烯基]-1,3-苯二醇; 白藜芦醇

Database IDs

• CAS Number: 501-36-0
• MDL Number: MFCD00133799
• PubChem SID: 160965883; 24860876; 24278055; 46504705
• PubChem CID: 445154
• CHEBI ID: 45713
• CHEMBL: 165
• Chemspider ID: 392875
• DrugBank ID: DB02709
• KEGG ID: C03582
• Unique Ingredient Identifier: Q369O8926L
• Wikipedia Title: Resveratrol

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.493489
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 3.4019527
• LogD (pH = 7.4): 3.3683183
• Log P: 3.402391
• Molar Refractivity: 67.4555 cm^3
• Polarizability: 25.321121 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.57
• LOG S: -3.52
• Solubility (Water): 6.88e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.03 g/L in water; 16 g/L in Dimethyl sulfoxide (DMSO); 50 g/L in ethanol; DMSO; Ethanol; Methanol
• Apperance: Off-White to Tan Solid; Powder; white powder with, slight yellow cast
• Melting Point: 243-253°C (dec.); 261 - 263°C / 501.8 - 505.4°F; 261-267°C
• Absorption Wavelength: 286nm (cis-resveratrol, in water); 304nm (trans-resveratrol, in water)

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: Harmful/Irritant/Corrosive/Keep Cold/Store under Argon; IRRITANT
• RTECS: CZ8987000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36; R36 (irritating to eyes)
• Safety Statements: 26; S26 (in case of contact with eyes, rinse immediately with plenty of water and seek medical advice)
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• LD50: 23.2 μM (5,29 g)
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... AR(367), CYP1A2(1544), ESR1(2099), SIRT1(23411)mouse ... Nos2(18126)rat ... Esr1(24890)
• Mechanism of Action: Tyrosinase inhibitor

Product Information

• Purity: ≥98%; ≥99% (GC); 95+%; 98%; 99.0
• Grade: analytical standard; certified reference material; TraceCERT®
• Salt Data: Free Base
• Biological Source: Phytoalexin from Veratrum grandiflorum (roots), Pinus sibirica (bark), Vitis vinifera and Arachis hypogaea. Also from Eucalyptus, Polygonum and Nothofagus spp. and Cudrania javanensis
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Bactericide; Fungicide; Neutriceutical with a positive influence on blood lipid profile; Resveratrol in red wines has been postulated to be associated with beneficial health effects
• Empirical Formula (Hill Notation): C14H12O3

DETAILS

MP Biomedicals - 02196052

Purity: >98% Present in wine and grapes and found to reduce serum lipids, inhibit platelet aggregation and act as a chemopreventative agent and antioxidant.

DrugBank - DB02709

• Drug Groups: experimental; investigational
• Description: Resveratrol (3,5,4'-trihydroxystilbene) is a polyphenolic phytoalexin. It is a stilbenoid, a derivate of stilbene, and is produced in plants with the help of the enzyme stilbene synthase. It exists as two structural isomers: cis-(Z) and trans-(E), with the trans-isomer shown in the top image. The trans- form can undergo isomerisation to the cis- form when heated or exposed to ultraviolet irradiation. In a 2004 issue of Science, Dr. Sinclair of Harvard University said resveratrol is not an easy molecule to protect from oxidation. It has been claimed that it is readily degraded by exposure to light, heat, and oxygen. However, studies find that Trans-resveratrol undergoes negligible oxidation in normal atmosphere at room temperature. [Wikipedia]
• Indication: Being investigated for the treatment of Herpes labialis infections (cold sores).
• Pharmacology: Resveratrol, a phytoalexin, has been found to inhibit herpes simplex virus types 1 and 2 (HSV-1 and HSV-2) replication in a dose-dependent, reversible manner, although this is only one of its many pharmaceutical properties. In some countries where there is higher consumption of red wine, there appears to be a lower incidence of heart disease. Other benefits of resveratrol include its anti-inflammatory and antioxidant effects. In preclinical studies, Resveratrol has been found to have potential anticancer properties.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Rapidly metabolized and excreted.
• Absorption: High absorption but very low bioavailability.
• Protein Binding: Strong affinity towards protein binding.
• References: Farina A, Ferranti C, Marra C: An improved synthesis of resveratrol. Nat Prod Res. 2006 Mar;20(3):247-52. [Pubmed] ; Renaud S, Ruf JC: The French paradox: vegetables or wine. Circulation. 1994 Dec;90(6):3118-9. [Pubmed] ; Wang Y, Catana F, Yang Y, Roderick R, van Breemen RB: An LC-MS method for analyzing total resveratrol in grape juice, cranberry juice, and in wine. J Agric Food Chem. 2002 Jan 30;50(3):431-5. [Pubmed] ; Lyons MM, Yu C, Toma RB, Cho SY, Reiboldt W, Lee J, van Breemen RB: Resveratrol in raw and baked blueberries and bilberries. J Agric Food Chem. 2003 Sep 24;51(20):5867-70. [Pubmed] ; Walle T, Hsieh F, DeLegge MH, Oatis JE Jr, Walle UK: High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab Dispos. 2004 Dec;32(12):1377-82. Epub 2004 Aug 27. [Pubmed] ; Csaki C, Keshishzadeh N, Fischer K, Shakibaei M: Regulation of inflammation signalling by resveratrol in human chondrocytes in vitro. Biochem Pharmacol. 2007 Sep 18;. [Pubmed] ; Docherty JJ, Fu MM, Stiffler BS, Limperos RJ, Pokabla CM, DeLucia AL: Resveratrol inhibition of herpes simplex virus replication. Antiviral Res. 1999 Oct;43(3):145-55. [Pubmed] ; N' soukpoe-Kossi CN, St-Louis C, Beauregard M, Subirade M, Carpentier R, Hotchandani S, Tajmir-Riahi HA: Resveratrol binding to human serum albumin. J Biomol Struct Dyn. 2006 Dec;24(3):277-83. [Pubmed]
• External Links: Wikipedia

Selleck Chemicals - S1396

Research Area: Inflammation
Biological Activity:
Resveratrol is a phytoalexin produced naturally by several plants when under attack by pathogens such as bacteria or fungi. The effects of resveratrol on the lifespan of many model organisms remain controversial, with uncertain effects in fruit flies, nematode worms, and short-lived fish. In mouse and rat experiments, anti-cancer, anti-inflammatory, blood-sugar-lowering and other beneficial cardiovascular effects of resveratrol have been reported. Most of these results have yet to be replicated in humans. [1]

InterBioScreen - BB_NC-2570

Polygonum cuspidatum Sieb. et Zucc.

Toronto Research Chemicals - R150000

Minor constituent of wine, correlated with serum lipid reduction and inhibition of platelet aggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been shown to inhibit events associa

Sigma Aldrich - R5010

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
COX-1 选择性抑制剂。
Biochem/physiol Actions
Resveratrol is a phenolic phytoalexin found in grape skin and other plants. It has intracellular antioxidant activity and activates SIRT1, a NAD+-dependent histone deacetylase involved in mitochondrial biogenesis and the enhancement of peroxisome proliferator-γ-activated receptor coactivator-1α (PGC-1α) and FOXO activity. The anti-diabetic, neuroprotective and anti-adipogenic actions of resveratrol may be mediated via SIRT1 activation.

Sigma Aldrich - 34092

Application
Selective inhibitor of COX-1.

Sigma Aldrich - 76511

Application
Selective inhibitor of COX-1.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Jang, M., et al., Science, 275(5297): 218-220, (1997).
• Renaud S, Ruf JC: The French paradox: vegetables or wine. Circulation. 1994 Dec;90(6):3118-9. Pubmed
• Farina A, Ferranti C, Marra C: An improved synthesis of resveratrol. Nat Prod Res. 2006 Mar;20(3):247-52. Pubmed
• Wang Y, Catana F, Yang Y, Roderick R, van Breemen RB: An LC-MS method for analyzing total resveratrol in grape juice, cranberry juice, and in wine. J Agric Food Chem. 2002 Jan 30;50(3):431-5. Pubmed
• Lyons MM, Yu C, Toma RB, Cho SY, Reiboldt W, Lee J, van Breemen RB: Resveratrol in raw and baked blueberries and bilberries. J Agric Food Chem. 2003 Sep 24;51(20):5867-70. Pubmed
• Walle T, Hsieh F, DeLegge MH, Oatis JE Jr, Walle UK: High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab Dispos. 2004 Dec;32(12):1377-82. Epub 2004 Aug 27. Pubmed
• Csaki C, Keshishzadeh N, Fischer K, Shakibaei M: Regulation of inflammation signalling by resveratrol in human chondrocytes in vitro. Biochem Pharmacol. 2007 Sep 18;. Pubmed
• Docherty JJ, Fu MM, Stiffler BS, Limperos RJ, Pokabla CM, DeLucia AL: Resveratrol inhibition of herpes simplex virus replication. Antiviral Res. 1999 Oct;43(3):145-55. Pubmed
• N' soukpoe-Kossi CN, St-Louis C, Beauregard M, Subirade M, Carpentier R, Hotchandani S, Tajmir-Riahi HA: Resveratrol binding to human serum albumin. J Biomol Struct Dyn. 2006 Dec;24(3):277-83. Pubmed
• http://en.wikipedia.org/wiki/Resveratrol
• Powell, R.G., et al.: Phytochemistry, 35, 335 (1994)
• Jeandet, P., et al.: J. Phytopathol., 143, 135 (1994)
• Mattivi, F., et al.: J. Agric. Food Chem., 43, 1820 (1994)
• Langcake, P. et al., Phytochemistry, 1977, 16, 1193