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Record Information
Version3.6
Creation Date2007-01-22 23:51:51 UTC
Update Date2016-02-11 01:07:17 UTC
HMDB IDHMDB05805
Secondary Accession NumbersNone
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-isopropylbenzeneChEBI
4-CymeneChEBI
P-CimeneChEBI
P-CymolChEBI
P-IsopropyltolueneChEBI
P-MethylcumeneChEBI
P-MethylisopropylbenzeneChEBI
1-Isopropyl-4-methyl-benzeneHMDB
1-Methyl-4-(1-methylethyl)-benzeneHMDB
2-P-TolylpropaneHMDB
4-Isopropyl-1-methylbenzeneHMDB
4-Isopropylbenzyl radicalHMDB
4-IsopropyltolueneHMDB
4-Methyl-1-(propan-2-yl)benzeneHMDB
4-Methyl-1-isopropylbenzeneHMDB
CamphogenHMDB
CymeneHMDB
CymolHMDB
DolcymeneHMDB
IsopropyltolueneHMDB
P- IsopropylmethylbenzeneHMDB
P-Mentha-1,3,5-trieneHMDB
P-Methyl cumeneHMDB
P-Methyl-cumeneHMDB
Para-cymeneHMDB
ParacymeneHMDB
ParacymolHMDB
Chemical FormulaC10H14
Average Molecular Weight134.2182
Monoisotopic Molecular Weight134.109550448
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 KeyInChIKey=HFPZCAJZSCWRBC-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
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • 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
StateGas
Experimental Properties
PropertyValueReference
Melting Point-68.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0234 mg/mL at 25 °CNot Available
LogP4.10HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.017 mg/mLALOGPS
logP4.17ALOGPS
logP3.73ChemAxon
logS-3.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.29 m3·mol-1ChemAxon
Polarizability17 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-014i-4900000000-c8d4189d8e9f124c75adView in MoNA
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 IDFDB017358
KNApSAcK IDC00003040
Chemspider ID7183
KEGG Compound IDC06575
BioCyc IDCPD-1001
BiGG IDNot Available
Wikipedia LinkP-cymene
NuGOwiki LinkHMDB05805
Metagene LinkHMDB05805
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. [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. [11341314 ]