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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-01-22 23:51:51 UTC
Update Date2022-03-07 02:49:29 UTC
HMDB IDHMDB0005805
Secondary Accession Numbers
  • HMDB05805
Metabolite Identification
Common Namep-Cymene
DescriptionCymene, or p-cymene also known as p-cymol or isopropyltoluene, 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 a common ligand for ruthenium.
Structure
Data?1582752365
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
4-MethylisopropylbenzenePhytoBank
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
Description 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

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-68.9 °CNot Available
Boiling Point176.00 to 178.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.023 mg/mL at 25 °CNot Available
LogP4.10HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.61631661259
DarkChem[M-H]-129.84431661259
DeepCCS[M+H]+137.78830932474
DeepCCS[M-H]-133.96130932474
DeepCCS[M-2H]-171.37530932474
DeepCCS[M+Na]+146.91430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-CymeneCC(C)C1=CC=C(C)C=C11283.2Standard polar33892256
p-CymeneCC(C)C1=CC=C(C)C=C11030.7Standard non polar33892256
p-CymeneCC(C)C1=CC=C(C)C=C11012.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - p-Cymene EI-B (Non-derivatized)splash10-014i-4900000000-f403355796ccc97b50112017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cymene EI-B (Non-derivatized)splash10-014i-3900000000-18fab12c9b06d75f28d42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cymene EI-B (Non-derivatized)splash10-001i-0900000000-146f5d56238ffde0a8d02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cymene CI-B (Non-derivatized)splash10-007x-4900000000-14f27e732fc9b57e0b122017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cymene EI-B (Non-derivatized)splash10-014i-4900000000-f403355796ccc97b50112018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cymene EI-B (Non-derivatized)splash10-014i-3900000000-18fab12c9b06d75f28d42018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cymene EI-B (Non-derivatized)splash10-001i-0900000000-146f5d56238ffde0a8d02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cymene CI-B (Non-derivatized)splash10-007x-4900000000-14f27e732fc9b57e0b122018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Cymene GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-8900000000-176f8c1c70e1e67b3d822016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Cymene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-4900000000-c8d4189d8e9f124c75ad2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 10V, Positive-QTOFsplash10-000i-0900000000-94c1bdcd85003d97aefc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 20V, Positive-QTOFsplash10-000i-2900000000-5ed611e91a5f86fc70192016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 40V, Positive-QTOFsplash10-0gbc-9700000000-f812cd4b0a2fcb99f91a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 10V, Negative-QTOFsplash10-001i-0900000000-3043af674a7adea6117a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 20V, Negative-QTOFsplash10-001i-0900000000-589b3edc66f090e075e52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 40V, Negative-QTOFsplash10-00lu-4900000000-9166f98044ef814ac56b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 10V, Negative-QTOFsplash10-001i-0900000000-f5fa2e4eafb73a2ce5ef2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 20V, Negative-QTOFsplash10-001i-0900000000-f5fa2e4eafb73a2ce5ef2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 40V, Negative-QTOFsplash10-00kf-9200000000-0d66e02ef78a9a9bac9a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 10V, Positive-QTOFsplash10-000f-9800000000-f6dc3a9bc8c029e844ff2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 20V, Positive-QTOFsplash10-0006-9100000000-31308f391d491363333e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cymene 40V, Positive-QTOFsplash10-002f-9000000000-0f55cd38142065afafc32021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB017358
KNApSAcK IDC00003040
Chemspider ID7183
KEGG Compound IDC06575
BioCyc IDCPD-1001
BiGG IDNot Available
Wikipedia LinkP-cymene
METLIN IDNot Available
PubChem Compound7463
PDB IDNot Available
ChEBI ID28768
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1032712
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 ]