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Showing Compound (S)-[6]-Gingerol (FDB001108)

Record Information
Version1.0
Creation date2010-04-08 22:04:50 UTC
Update date2019-11-26 02:55:55 UTC
Primary IDFDB001108
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-[6]-Gingerol
DescriptionGingerol belongs to the class of organic compounds known as gingerols. Gingerols are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one. Gingerol is a pungent tasting compound. Gingerol is found, on average, in the highest concentration within gingers (Zingiber officinale). Gingerol has also been detected, but not quantified in, several different foods, such as cloves (Syzygium aromaticum), star anises (Illicium verum), ceylon cinnamons (Cinnamomum verum), pepper (spice), and nutmegs (Myristica fragrans). This could make gingerol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Gingerol.
CAS Number58253-27-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
6g [6]-GingerolChEMBL, HMDB
5-Hydroxy-1-(4-hydroxy-3-methoxtphenyl)-3-decanoneHMDB
5-Hydroxy-1-(4-hydroxy-3-methoxycyclohexyl)decan-3-oneHMDB
6-GingerolHMDB
[6]-GingerolHMDB
(6)-GingerolMeSH, HMDB
10-GingerolMeSH, HMDB
(+)-[6]-Gingerolbiospider
(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-onebiospider
(S)-(+)-[6]-Gingerolbiospider
(S)-(+)-[6]Gingerolbiospider
(S)-6-Gingerolbiospider
3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-biospider
5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanonebiospider
Gingerolbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP3.45ALOGPS
logP3.62ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity83.11 m³·mol⁻¹ChemAxon
Polarizability33.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H26O4
IUPAC name5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
InChI IdentifierInChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3
InChI KeyNLDDIKRKFXEWBK-UHFFFAOYSA-N
Isomeric SMILESCCCCCC(O)CC(=O)CCC1=CC=C(O)C(OC)=C1
Average Molecular Weight294.3859
Monoisotopic Molecular Weight294.18310932
Classification
Description Belongs to the class of organic compounds known as gingerols. Gingerols are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentGingerols
Alternative Parents
Substituents
  • Gingerol
  • Fatty alcohol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Beta-hydroxy ketone
  • Fatty acyl
  • Ketone
  • Secondary alcohol
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 69.36%; H 8.90%; O 21.74%DFC
Melting Point31 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +26.5 (c, 1 in CHCl3)DFC
Spectroscopic UV Data282 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(S)-[6]-Gingerol, non-derivatized, GC-MS Spectrumsplash10-000i-3910000000-3c07be71d662410144abSpectrum
GC-MS(S)-[6]-Gingerol, non-derivatized, GC-MS Spectrumsplash10-000i-3910000000-3c07be71d662410144abSpectrum
Predicted GC-MS(S)-[6]-Gingerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-6900000000-9e3ae5652d5b17b9016dSpectrum
Predicted GC-MS(S)-[6]-Gingerol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7119300000-fbff188e294cacd919c6Spectrum
Predicted GC-MS(S)-[6]-Gingerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0920000000-010ef6242d9f56fa2a722017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-36e283e52cb0ba857d0e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-35209ecc08a0fcbe33382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-1900000000-aefaf0623f9721907b4d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00du-6900000000-50259fc38798f28309322017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0900000000-35209ecc08a0fcbe33382021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-aefaf0623f9721907b4d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-36e283e52cb0ba857d0e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0920000000-010ef6242d9f56fa2a722021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00du-6900000000-50259fc38798f28309322021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0290000000-da571dea1713ff08f13b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-4930000000-922f5386fa26a96a1bbc2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9400000000-e27c462b7ff389743a4c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-d356007500cff17f32ac2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-3930000000-be6a576d74a0f97fb8fc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5900000000-31f35b868a26cada9bf52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0551-0590000000-d52178d2e2ff78317f7b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-2940000000-060d47dec6b201c1d70d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3900000000-2ea673e61b75d0b2bbe92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-4590000000-b65edb04dc7fdd19e6e32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6890000000-9e209efe1855c3c2ace72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9700000000-cd27d9c02d1d0d56a9542021-09-23View Spectrum
NMRNot Available
ChemSpider ID3354
ChEMBL IDCHEMBL1950582
KEGG Compound IDC10462
Pubchem Compound ID3473
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID648
DrugBank IDNot Available
HMDB IDHMDB05783
CRC / DFC (Dictionary of Food Compounds) IDHCV46-D:BTF04-O
EAFUS IDNot Available
Dr. Duke ID6-GINGEROL|GINGEROL|(+)-6-GINGEROL
BIGG IDNot Available
KNApSAcK IDC00002748
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1384651
SuperScent IDNot Available
Wikipedia IDGingerol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
amphitensiveDUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti 5-hydroxytryptamine48279 Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.DUKE
anti aggregantDUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti emetic50919 A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
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 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 pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti schistosomiac33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti seratogenicDUKE
anti thromboxane35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti tussive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardiodepressant38070 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
cardiotonic38070 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
cholagogueDUKE
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
depressorDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
gastrostimulant55324 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypertensiveDUKE
hypotensiveDUKE
inotropicDUKE
larvicideDUKE
molluscicide33904 A substance used to destroy pests of the phylum Mollusca.DUKE
mutagenicDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).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
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
thermogenicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
pungent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— 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.