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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-01-23 13:01:01 UTC
Update Date2017-12-07 01:55:31 UTC
HMDB IDHMDB0005806
Secondary Accession Numbers
  • HMDB05806
Metabolite Identification
Common NameGamma-terpinene
DescriptionThe terpinenes are three isomeric hydrocarbons that are classified as terpenes. Gamma-terpinene is one these three isomeric hydrocarbons. It is natural and has been isolated from a variety of plant sources (Wikipedia). It is a major component of essential oils made from Citrus Fruits and has strong antioxidant activity. It has a lemon odor and widely used in food, flavours, soaps, cosmetics, pharmaceutical, tabacco, confectionery and perfume industries (http://www.gyanflavoursexport.com).
Structure
Thumb
Synonyms
ValueSource
1,4-P-MenthadieneChEBI
1-Isopropyl-4-methyl-1,4-cyclohexadieneChEBI
1-Isopropyl-4-methylcyclohexa-1,4-dieneChEBI
1-Methyl-4-(1-methylethyl)-1,4-cyclohexadieneChEBI
1-Methyl-4-propan-2-ylcyclohexa-1,4-dieneChEBI
4-Isopropyl-1-methyl-1,4-cyclohexadieneChEBI
CrithmeneChEBI
MosleneChEBI
P-Mentha-1,4-dieneChEBI
g-TerpineneGenerator
γ-terpineneGenerator
1-Methyl-4-(propan-2-yl)cyclohexa-1,4-dieneHMDB
alpha TerpineneHMDB
gamma TerpineneHMDB
gamma-TerpinenHMDB
TerpineneHMDB
beta-TerpineneMeSH
alpha-TerpineneMeSH
Chemical FormulaC10H16
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
IUPAC Name1-methyl-4-(propan-2-yl)cyclohexa-1,4-diene
Traditional Nameα terpinene
CAS Registry Number99-85-4
SMILES
CC(C)C1=CCC(C)=CC1
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3
InChI KeyYKFLAYDHMOASIY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.
KingdomChemical entities
Super ClassOrganic compounds
ClassHydrocarbons
Sub ClassUnsaturated hydrocarbons
Direct ParentBranched unsaturated hydrocarbons
Alternative Parents
Substituents
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Olefin
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Plant:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-10 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0087 mg/mL at 22 °CNot Available
LogP4.50LI,J & PERDUE,EM (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP4.36ALOGPS
logP3.16ChemAxon
logS-2.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.55 m³·mol⁻¹ChemAxon
Polarizability17.61 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-b05d52aa0731550051f6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9400000000-a5cb265912cd3b36ec3fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9500000000-2b0e829aa7638afa325eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-78ed493eae24d7cd7247View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0019-8900000000-4f8f18604be188d356c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-015c-9000000000-7cd3ebd6c5315af11ec5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002f-9000000000-796d72dfa199c02320d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9200000000-ddf6ab2c599f6a3a0e04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-9400000000-701e197e734bd825ea09View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-9500000000-156890c59245ff11b54dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-7132f17a85333e784956View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9700000000-f4bee8ac3721685bb606View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-dbeffc46ec6acbacb6efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-545d284bbb3189d5973dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-838b737755ef4340d8a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-6900000000-6351b5255caae6105b15View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9300000000-97923633c0b05f03274fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)Both
Diarrhea-predominant IBS
details
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB015968
KNApSAcK IDC00003061
Chemspider ID7181
KEGG Compound IDC09900
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTerpinene
METLIN IDNot Available
PubChem Compound7461
PDB IDNot Available
ChEBI ID10577
References
Synthesis ReferenceRichter, Friedrich; Wolff, Werner; Presting, W. g-Terpinene. II. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1930), 63B 1714-21. CODEN: BDCBAD ISSN:0365-9488. CAN 24:46537 AN 1930:46537
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available