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
Synonyms
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
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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.