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Showing Compound (S)-[10]-Gingerol (FDB011704)

Record Information
Version1.0
Creation date2010-04-08 22:09:47 UTC
Update date2019-11-26 03:05:19 UTC
Primary IDFDB011704
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-[10]-Gingerol
Description(S)-[10]-Gingerol 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 (S)-[10]-Gingerol is a musk and woody tasting compound (S)-[10]-Gingerol has been detected, but not quantified in, gingers (Zingiber officinale) and herbs and spices. This could make (S)-[10]-gingerol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-[10]-Gingerol.
CAS Number23513-15-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(10)-GingerolHMDB
(S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanoneHMDB
[10]-GingerolHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP5.59ALOGPS
logP5.39ChemAxon
logS-4.5ALOGPS
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 Count14ChemAxon
Refractivity101.51 m³·mol⁻¹ChemAxon
Polarizability42.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H34O4
IUPAC name5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one
InChI IdentifierInChI=1S/C21H34O4/c1-3-4-5-6-7-8-9-10-18(22)16-19(23)13-11-17-12-14-20(24)21(15-17)25-2/h12,14-15,18,22,24H,3-11,13,16H2,1-2H3
InChI KeyAIULWNKTYPZYAN-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCCC(O)CC(=O)CCC1=CC(OC)=C(O)C=C1
Average Molecular Weight350.4923
Monoisotopic Molecular Weight350.245709576
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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.96%; H 9.78%; O 18.26%DFC
Melting PointMp 45-46°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +22.7 (c, 1.02 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-[10]-Gingerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-3911000000-844d81a34f8dfcd2dd2bSpectrum
Predicted GC-MS(S)-[10]-Gingerol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fi0-8091300000-527c8ffbf403b8e65b6aSpectrum
Predicted GC-MS(S)-[10]-Gingerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0209000000-88b2e4785cf94422a2ed2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fc9-1902000000-d86d9638941b51db00042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-6910000000-17ddae55b3c1387598c42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0309000000-52ab87c2fc758f77177e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002g-0903000000-0fa5a8390ce6dc5835ec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3910000000-015267b6d4db8e8994dd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0209000000-418c91995389483668622021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-3958000000-4a4b51b2a2ed27cb0dfa2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l1c-8900000000-68b2a292051cabc6583b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-0009000000-9668d93711e78669059e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06rb-4916000000-c040acf5267c3c5844e12021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abi-6911000000-5bf1e9fc38d4added0032021-09-25View Spectrum
NMRNot Available
ChemSpider ID4439827
ChEMBL IDNot Available
KEGG Compound IDC17496
Pubchem Compound ID5275726
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33616
CRC / DFC (Dictionary of Food Compounds) IDGYB82-C:GYH47-Z
EAFUS IDNot Available
Dr. Duke ID10-GINGEROL
BIGG IDNot Available
KNApSAcK IDC00031474
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1384661
SuperScent IDNot Available
Wikipedia IDNot Available
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
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
thermogenicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
musk
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  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— 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.