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Record Information
Version1.0
Creation Date2014-09-11 05:21:03 UTC
Update Date2016-11-09 01:09:13 UTC
Accession NumberCHEM003846
Identification
Common NameGamma-terpinene
ClassSmall Molecule
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).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Cosmetic Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical 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
1-Methyl-4-isopropyl-1,4-cyclohexadienePhytoBank
gamma-TerpinenePhytoBank
γ-TerpinenPhytoBank
Chemical FormulaC10H16
Average Molecular Mass136.238 g/mol
Monoisotopic Mass136.125 g/mol
CAS Registry Number99-85-4
IUPAC Name1-methyl-4-(propan-2-yl)cyclohexa-1,4-diene
Traditional Nameα terpinene
SMILESCC(C)C1=CCC(C)=CC1
InChI IdentifierInChI=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
Description belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassBranched unsaturated 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-10 °C
Boiling PointNot Available
Solubility0.00868 mg/mL at 22 °C
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0006-9300000000-78ed493eae24d7cd7247View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9200000000-b05d52aa0731550051f6View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9400000000-a5cb265912cd3b36ec3fView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9500000000-2b0e829aa7638afa325eView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9200000000-b05d52aa0731550051f6View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9400000000-a5cb265912cd3b36ec3fView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9500000000-2b0e829aa7638afa325eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-Qsplash10-0006-9200000000-85beacebb887bcf22446View 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
LC-MS/MSLC-MS/MS Spectrum - LC-Q-TOF/MS 25V, negativesplash10-000i-0900000000-98cfc7dd6d4b6ccbba0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-Q-TOF/MS 30V, negativesplash10-0019-2900000000-898e1880d94396f2ba76View 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
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005806
FooDB IDFDB015968
Phenol Explorer IDNot Available
KNApSAcK IDC00003061
BiGG IDNot Available
BioCyc IDCPD-8736
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTerpinene
Chemspider ID7181
ChEBI ID10577
PubChem Compound ID7461
Kegg Compound IDC09900
YMDB IDYMDB16107
ECMDB IDNot Available
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
MSDSLink
General References
1. Richter, 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
2. Richter, 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
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12696969
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17314143
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22284503
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24066512
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24421258