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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-01-22 23:51:51 UTC
Update Date2018-05-19 23:38:22 UTC
HMDB IDHMDB0005805
Secondary Accession Numbers
  • HMDB05805
Metabolite Identification
Common Namep-Cymene
DescriptionCymene, or p-cymene, is a naturally occurring aromatic organic compound. It is classified as a hydrocarbon related to a monoterpene. Its structure consists of a benzene ring para-substituted with a methyl group and an isopropyl group. It is insoluble in water, but miscible with ethanol and ether. Cymene is a constituent of a number of essential oils, most commonly the oil of cumin and thyme. There are two less common geometric isomers. o-Cymene, in which the alkyl groups are ortho-substituted, and m-cymene, in which they are meta-substituted. p-Cymene is the only natural isomer. Cymene is common ligand for ruthenium. The parent compound is [(η6-cymene)MCl2]2. This [sandwich compound|half-sandwich compound is prepared by the reaction of ruthenium trichloride with the terpene α-phellandrene. The osmium complex is also known (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
1-Isopropyl-4-methylbenzeneChEBI
1-Methyl-4-(1-methylethyl)benzeneChEBI
1-Methyl-4-(propan-2-yl)benzeneChEBI
1-Methyl-4-isopropylbenzeneChEBI
4-CymeneChEBI
4-Isopropyl-1-methylbenzeneChEBI
4-IsopropyltolueneChEBI
4-Methyl-1-isopropylbenzeneChEBI
CymeneChEBI
IsopropyltolueneChEBI
P-CimeneChEBI
P-CymolChEBI
P-IsopropyltolueneChEBI
P-MethylcumeneChEBI
P-MethylisopropylbenzeneChEBI
Para-cymeneChEBI
1-Isopropyl-4-methyl-benzeneHMDB
1-Methyl-4-(1-methylethyl)-benzeneHMDB
2-P-TolylpropaneHMDB
4-Isopropylbenzyl radicalHMDB
4-Methyl-1-(propan-2-yl)benzeneHMDB
CamphogenHMDB
CymolHMDB
DolcymeneHMDB
P- IsopropylmethylbenzeneHMDB
P-Mentha-1,3,5-trieneHMDB
P-Methyl cumeneHMDB
P-Methyl-cumeneHMDB
ParacymeneHMDB
ParacymolHMDB
Chemical FormulaC10H14
Average Molecular Weight134.222
Monoisotopic Molecular Weight134.109550451
IUPAC Name1-methyl-4-(propan-2-yl)benzene
Traditional Namecymene
CAS Registry Number99-87-6
SMILES
CC(C)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3
InChI KeyHFPZCAJZSCWRBC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • P-cymene
  • Phenylpropane
  • Cumene
  • Toluene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-68.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.023 mg/mL at 25 °CNot Available
LogP4.10HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP4.17ALOGPS
logP3.73ChemAxon
logS-3.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.29 m³·mol⁻¹ChemAxon
Polarizability17 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)splash10-014i-4900000000-f403355796ccc97b5011View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-3900000000-18fab12c9b06d75f28d4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-0900000000-146f5d56238ffde0a8d0View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-007x-4900000000-14f27e732fc9b57e0b12View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-4900000000-f403355796ccc97b5011View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-3900000000-18fab12c9b06d75f28d4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-0900000000-146f5d56238ffde0a8d0View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-007x-4900000000-14f27e732fc9b57e0b12View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-8900000000-176f8c1c70e1e67b3d82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-94c1bdcd85003d97aefcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-5ed611e91a5f86fc7019View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9700000000-f812cd4b0a2fcb99f91aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-3043af674a7adea6117aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-589b3edc66f090e075e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lu-4900000000-9166f98044ef814ac56bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-014i-4900000000-c8d4189d8e9f124c75adView in MoNA
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
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017358
KNApSAcK IDC00003040
Chemspider ID7183
KEGG Compound IDC06575
BioCyc IDCPD-1001
BiGG IDNot Available
Wikipedia LinkP-cymene
METLIN IDNot Available
PubChem Compound7463
PDB IDMML
ChEBI ID28768
References
Synthesis ReferenceFevre, Catherine G. Le; Fevre, Raymond J. W. Le; Robertson, Kathleen W. Dipole moments of p-cymene, 2- and 3-halogeno-pcymenes, carvacrol and thymol, p-ethyltoluene, p-tert-butyltoluene, 1,3-dimethyl-5-tert-butylbenzene, tert-butyl-benzene and its p-nitro
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Thompson JD, Chalchat JC, Michet A, Linhart YB, Ehlers B: Qualitative and quantitative variation in monoterpene co-occurrence and composition in the essential oil of Thymus vulgaris chemotypes. J Chem Ecol. 2003 Apr;29(4):859-80. [PubMed:12775148 ]
  2. Nishio T, Patel A, Wang Y, Lau PC: Biotransformations catalyzed by cloned p-cymene monooxygenase from Pseudomonas putida F1. Appl Microbiol Biotechnol. 2001 Apr;55(3):321-5. [PubMed:11341314 ]