Record Information
Version1.0
Creation date2010-04-08 22:05:23 UTC
Update date2020-04-21 18:04:11 UTC
Primary IDFDB002451
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(E)-Resveratrol
DescriptionResveratrol, also known as trans-resveratrol or SRT 501, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Thus, resveratrol is considered to be an aromatic polyketide lipid molecule. Resveratrol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Resveratrol exists in all living species, ranging from bacteria to humans. Resveratrol is found, on average, in the highest concentration within red wines. Resveratrol has also been detected, but not quantified in, several different foods, such as groundcherries, yellow pond-lilies, sesames, lemons, and sweet marjorams. This could make resveratrol a potential biomarker for the consumption of these foods.
CAS Number501-36-0
Structure
Thumb
Synonyms
SynonymSource
(e)-5-(2-(4-Hydroxyphenyl)ethenyl)-1,3-benzenediolChEBI
(E)-ResveratrolChEBI
3,4',5-StilbenetriolChEBI
3,4',5-Trihydroxy-trans-stilbeneChEBI
3,4',5-TrihydroxystilbeneChEBI
3,5,4'-TrihydroxystilbeneChEBI
5-[(e)-2-(4-Hydroxyphenyl)vinyl]benzene-1,3-diolChEBI
trans-3,4',5 - TrihydroxystilbeneHMDB
trans-ResveratrolHMDB, KEGG
SRT 501MeSH, HMDB
SRT-501MeSH, HMDB
trans ResveratrolMeSH, HMDB
(E)-2-(3,5-Dihydroxyphenyl)-1-(4-hydroxyphenyl)etheneHMDB
(E)-3,4',5-TrihydroxystilbeneHMDB
(E)-3,4’,5-TrihydroxystilbeneHMDB
(E)-5-(p-Hydroxystyryl)resorcinolHMDB
3,4’,5-StilbenetriolHMDB
3,4’,5-Trihydroxy-trans-stilbeneHMDB
3,4’,5-TrihydroxystilbeneHMDB
5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediolHMDB
ResveratrolHMDB
trans-3,5,4'-TrihydroxystilbeneHMDB
trans-3,5,4’-TrihydroxystilbeneHMDB
5-[(E)-2-(4-hydroxyphenyl)vinyl]benzene-1,3-diolmanual
E-Resveratrolmanual
RESVERATROLChEBI
trans-3,4,5-Trihydroxystilbenebiospider
trans-3,4',5-Trihydroxystilbenebiospider
trans-5-[2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diolbiospider
Predicted PropertiesNot Available
Chemical FormulaC14H12O3
IUPAC name
InChI IdentifierInChI=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+
InChI KeyLUKBXSAWLPMMSZ-OWOJBTEDSA-N
Isomeric SMILESOC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1
Average Molecular Weight228.247
Monoisotopic Molecular Weight228.078644246
Classification
Description belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Styrene
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Foods

Beverages:

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 73.67%; H 5.30%; O 21.03%DFC
Melting PointMp 265-267°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data320 (e 26900) (EtOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0006-1853900000-4919511a11ec24935434JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-1853900000-4919511a11ec24935434JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0790000000-615dafbde185688e8755JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00fr-8009800000-8b40ad68f231308861d4JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-f9ff90d98488d6d05587JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0090000000-f9ff90d98488d6d05587JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-004i-0090000000-f9ff90d98488d6d05587JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0590000000-4a9b53d6aad6ed8189d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0590000000-4a9b53d6aad6ed8189d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-f9ff90d98488d6d05587JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-014i-0900000000-79bf3bfcbb7bcdd0ffd2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-014i-0900000000-9340e3fe04d435cf8475JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0590000000-4a9b53d6aad6ed8189d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00kf-0900000000-b0f6bf3388d96335d77eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-1890000000-5a90c0c5508894cb16afJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-2910000000-e0183692948660939c19JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0090000000-d9def7cee71fb7a40786JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004r-0970000000-f8c7ca07f27bfc1b8bdaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-b1333b06db343c38f529JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014l-0900000000-c856c7fa9653868e5785JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004r-0950000000-8e44b9aa58ac75282058JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000f-0900000000-2b750fcfd933ce8809f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0900000000-79bf3bfcbb7bcdd0ffd2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-655581acb694e423a693JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0690000000-37f13318e23ebae81b00JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-3910000000-e87807281eb836a65eb0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-0d55e176d88ed31cd1cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-cfdf20e77b23e0cc49e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a73-3930000000-243d9e319d0fee123deeJSpectraViewer
ChemSpider ID392875
ChEMBL IDCHEMBL165
KEGG Compound IDC03582
Pubchem Compound ID445154
Pubchem Substance IDNot Available
ChEBI ID27881
Phenol-Explorer ID592
DrugBank IDDB02709
HMDB IDHMDB03747
CRC / DFC (Dictionary of Food Compounds) IDGZM37-C:CLW14-F
EAFUS IDNot Available
Dr. Duke ID3,5,4'-TRIHYDROXYSTILBENE|TRANS-RESVERATROL|RESVERATROL
BIGG IDNot Available
KNApSAcK IDC00002903
HET IDSTL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDResveratrol
Phenol-Explorer Metabolite ID580
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-hydroxyeicosatetraenoic-acid inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
5-hydroxytryptamine inhibitor48279 Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.DUKE
5-lipoxygenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
serine/threonine kinase inhibitor50925 An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of non-specific serine/threonine protein kinase (EC 2.7.11.1), a kinase enzyme involved in phosphorylation of hydroxy group of serine or threonine.DUKE
anti aggregantDUKE
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti edemicDUKE
anti eicosanoid35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti leukotriene35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti lipoperoxidantDUKE
anti mutagenicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti peroxidantDUKE
anti proliferantDUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti radicularDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti thrombic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
apoptoticDUKE
artemicideDUKE
beta-glucuronidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cardioprotective38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
casein-kinase-II inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cyclooxygenase-1 inhibitor50630 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
cytochrome-CYP1A1 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
differentiatorDUKE
elastase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
estrogenicDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
HIF-1alpha inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
hydroperoxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
hypocholesterolemicDUKE
hypotriglyceridemicDUKE
IKB-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
JNK inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
lipolyticDUKE
mitogen-activated-protein-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
NADH-ubiquinone-oxidoreductase inhibitor50390 An EC 1.6.5.* (oxidoreductase acting on NADH or NADPH with a quinone or similar as acceptor) inhibitor that interferes with the action of NAD(P)H dehydrogenase (quinone), EC 1.6.5.2.DUKE
NF-kappa-B inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
ornithine-decarboxylase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
protein kinase C inhibitor37700 An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13).DUKE
protein kinase D inhibitor37699 An EC 2.7.* (P-containing group transferase) inhibitor that interferes with the action of protein kinases.DUKE
protein-tyrosine-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
quinone-reductase inducerDUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
VEGF inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.