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Record Information
Version3.6
Creation Date2007-01-23 13:01:01 UTC
Update Date2016-02-11 01:07:17 UTC
HMDB IDHMDB05806
Secondary Accession NumbersNone
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-Methyl-4-(1-methylethyl)-1,4-cyclohexadieneChEBI
4-Isopropyl-1-methyl-1,4-cyclohexadieneChEBI
CrithmeneChEBI
MosleneChEBI
P-Mentha-1,4-dieneChEBI
1,4-P-MenthadieneHMDB
1-Isopropyl-4-methyl-1,4-cyclohexadieneHMDB
1-Isopropyl-4-methylcyclohexa-1,4-dieneHMDB
1-Methyl-4-(propan-2-yl)cyclohexa-1,4-dieneHMDB
alpha TerpineneHMDB
gamma TerpineneHMDB
gamma-TerpinenHMDB
TerpineneHMDB
Chemical FormulaC10H16
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
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 KeyInChIKey=YKFLAYDHMOASIY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclic olefins. These are olefins that contain at least one ring in their structure.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassOlefins
Sub ClassCyclic olefins
Direct ParentCyclic olefins
Alternative ParentsNot Available
Substituents
  • Cyclic olefin
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Food
  • Plant
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-10 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00868 mg/mL at 22 °CNot Available
LogP4.50LI,J & PERDUE,EM (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.54 mg/mLALOGPS
logP4.36ALOGPS
logP3.16ChemAxon
logS-2.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.55 m3·mol-1ChemAxon
Polarizability17.61 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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 Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Diarrhea-predominant IBS
details
UrineDetected but not QuantifiedNot ApplicableAdult (>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
NuGOwiki LinkHMDB05806
Metagene LinkHMDB05806
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