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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:21:49 UTC
Update Date2022-03-07 02:53:47 UTC
HMDB IDHMDB0033615
Secondary Accession Numbers
  • HMDB33615
Metabolite Identification
Common Name(S)-[8]-Gingerol
Description(S)-[8]-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)-[8]-Gingerol is found, on average, in the highest concentration within gingers (Zingiber officinale) (S)-[8]-Gingerol has also been detected, but not quantified in, herbs and spices. This could make (S)-[8]-gingerol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-[8]-Gingerol.
Structure
Data?1563862433
Synonyms
ValueSource
(8)-GingerolHMDB
(S)-(+)-[8]-GingerolHMDB
(S)-8-GingerolHMDB
Chemical FormulaC19H30O4
Average Molecular Weight322.4391
Monoisotopic Molecular Weight322.214409448
IUPAC Name5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one
Traditional Name5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one
CAS Registry Number23513-08-8
SMILES
CCCCCCCC(O)CC(=O)CCC1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C19H30O4/c1-3-4-5-6-7-8-16(20)14-17(21)11-9-15-10-12-18(22)19(13-15)23-2/h10,12-13,16,20,22H,3-9,11,14H2,1-2H3
InChI KeyBCIWKKMTBRYQJU-UHFFFAOYSA-N
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point29 - 30 °CNot Available
Boiling Point475.00 to 477.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility20.32 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.881 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP4.33ALOGPS
logP4.51ChemAxon
logS-3.9ALOGPS
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 Count12ChemAxon
Refractivity92.31 m³·mol⁻¹ChemAxon
Polarizability37.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.95131661259
DarkChem[M-H]-181.84331661259
DeepCCS[M+H]+188.10830932474
DeepCCS[M-H]-185.7530932474
DeepCCS[M-2H]-218.63630932474
DeepCCS[M+Na]+194.20130932474
AllCCS[M+H]+185.032859911
AllCCS[M+H-H2O]+182.032859911
AllCCS[M+NH4]+187.732859911
AllCCS[M+Na]+188.532859911
AllCCS[M-H]-185.032859911
AllCCS[M+Na-2H]-186.232859911
AllCCS[M+HCOO]-187.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-[8]-GingerolCCCCCCCC(O)CC(=O)CCC1=CC(OC)=C(O)C=C14234.5Standard polar33892256
(S)-[8]-GingerolCCCCCCCC(O)CC(=O)CCC1=CC(OC)=C(O)C=C12530.5Standard non polar33892256
(S)-[8]-GingerolCCCCCCCC(O)CC(=O)CCC1=CC(OC)=C(O)C=C12610.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-[8]-Gingerol,1TMS,isomer #1CCCCCCCC(CC(=O)CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2555.6Semi standard non polar33892256
(S)-[8]-Gingerol,1TMS,isomer #2CCCCCCCC(O)CC(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C12660.1Semi standard non polar33892256
(S)-[8]-Gingerol,1TMS,isomer #3CCCCCCCC(O)CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2754.4Semi standard non polar33892256
(S)-[8]-Gingerol,1TMS,isomer #4CCCCCCCC(O)C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2687.9Semi standard non polar33892256
(S)-[8]-Gingerol,2TMS,isomer #1CCCCCCCC(CC(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2580.7Semi standard non polar33892256
(S)-[8]-Gingerol,2TMS,isomer #2CCCCCCCC(CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2717.0Semi standard non polar33892256
(S)-[8]-Gingerol,2TMS,isomer #3CCCCCCCC(C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2661.7Semi standard non polar33892256
(S)-[8]-Gingerol,2TMS,isomer #4CCCCCCCC(O)CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2777.4Semi standard non polar33892256
(S)-[8]-Gingerol,2TMS,isomer #5CCCCCCCC(O)C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2690.2Semi standard non polar33892256
(S)-[8]-Gingerol,3TMS,isomer #1CCCCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2741.1Semi standard non polar33892256
(S)-[8]-Gingerol,3TMS,isomer #1CCCCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2650.9Standard non polar33892256
(S)-[8]-Gingerol,3TMS,isomer #2CCCCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2665.1Semi standard non polar33892256
(S)-[8]-Gingerol,3TMS,isomer #2CCCCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2592.1Standard non polar33892256
(S)-[8]-Gingerol,1TBDMS,isomer #1CCCCCCCC(CC(=O)CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2796.3Semi standard non polar33892256
(S)-[8]-Gingerol,1TBDMS,isomer #2CCCCCCCC(O)CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C12897.7Semi standard non polar33892256
(S)-[8]-Gingerol,1TBDMS,isomer #3CCCCCCCC(O)CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2993.2Semi standard non polar33892256
(S)-[8]-Gingerol,1TBDMS,isomer #4CCCCCCCC(O)C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2934.4Semi standard non polar33892256
(S)-[8]-Gingerol,2TBDMS,isomer #1CCCCCCCC(CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C3045.5Semi standard non polar33892256
(S)-[8]-Gingerol,2TBDMS,isomer #2CCCCCCCC(CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3179.9Semi standard non polar33892256
(S)-[8]-Gingerol,2TBDMS,isomer #3CCCCCCCC(C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3138.4Semi standard non polar33892256
(S)-[8]-Gingerol,2TBDMS,isomer #4CCCCCCCC(O)CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C3254.2Semi standard non polar33892256
(S)-[8]-Gingerol,2TBDMS,isomer #5CCCCCCCC(O)C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C3174.1Semi standard non polar33892256
(S)-[8]-Gingerol,3TBDMS,isomer #1CCCCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3426.0Semi standard non polar33892256
(S)-[8]-Gingerol,3TBDMS,isomer #1CCCCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3184.0Standard non polar33892256
(S)-[8]-Gingerol,3TBDMS,isomer #2CCCCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3370.3Semi standard non polar33892256
(S)-[8]-Gingerol,3TBDMS,isomer #2CCCCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3117.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-[8]-Gingerol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-6900000000-4f27e9897e4d1c2b5d762017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-[8]-Gingerol GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-9082400000-2144ce64c6b83bb339352017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-[8]-Gingerol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-[8]-Gingerol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 10V, Positive-QTOFsplash10-0ab9-0309000000-587122b082c72bab35312016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 20V, Positive-QTOFsplash10-06vr-2901000000-8414f641b78f94d194b72016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 40V, Positive-QTOFsplash10-052o-9710000000-af839b85cb673a5452392016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 10V, Negative-QTOFsplash10-00di-0309000000-46d6a39f29323fcb357b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 20V, Negative-QTOFsplash10-0096-0902000000-ce49f082d455f2acad952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 40V, Negative-QTOFsplash10-056r-3900000000-8907ef945fcc1b59801d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 10V, Negative-QTOFsplash10-0udi-0109000000-77e68dc4f0c25ccd33882021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 20V, Negative-QTOFsplash10-05g0-3904000000-fb3e4fb55be0a54209392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 40V, Negative-QTOFsplash10-0a70-6900000000-2f078562dae9f88f595a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 10V, Positive-QTOFsplash10-05g0-0539000000-24ea957f0bc366cb6c262021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 20V, Positive-QTOFsplash10-000i-1961000000-a92af492b4f7ef7d2cbd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[8]-Gingerol 40V, Positive-QTOFsplash10-0k9i-4900000000-92cc86691469f07313e62021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011703
KNApSAcK IDC00031475
Chemspider ID4439826
KEGG Compound IDC17495
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5275725
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1384641
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .