Tmic
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Record Information
Version2.0
Creation Date2014-09-11 05:20:42 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4882
Identification
Common Namep-Cymene
ClassSmall Molecule
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).
Compound Type
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
1-Isopropyl-4-methyl-Benzene
1-Isopropyl-4-methylbenzene
1-Methyl-4-(1-methylethyl)-benzene
1-Methyl-4-(1-methylethyl)benzene
2-p-Tolylpropane
4-Cymene
4-Isopropyl-1-methylbenzene
4-Isopropylbenzyl radical
4-Isopropyltoluene
4-Methyl-1-(propan-2-yl)benzene
4-Methyl-1-isopropylbenzene
Camphogen
Cymene
Cymol
Dolcymene
Isopropyltoluene
P- Isopropylmethylbenzene
P-Cimene
P-Cymene
P-Cymol
P-Isopropyltoluene
p-Mentha-1,3,5-triene
P-Methyl cumene
p-Methyl-Cumene
P-Methylcumene
P-Methylisopropylbenzene
Para-cymene
Paracymene
Paracymol
Chemical FormulaC10H14
Average Molecular Mass134.218 g/mol
Monoisotopic Mass134.110 g/mol
CAS Registry Number99-87-6
IUPAC Name1-methyl-4-(propan-2-yl)benzene
Traditional Namecymene
SMILESCC(C)C1=CC=C(C)C=C1
InChI IdentifierInChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3
InChI KeyInChIKey=HFPZCAJZSCWRBC-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
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
StateGas
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-68.9 °C
Boiling Point177.1°C (350.8°F)
Solubility0.0234 mg/mL at 25 °C
LogP4.10
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
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB05805
PubChem Compound ID7463
ChEMBL IDCHEMBL442915
ChemSpider ID7183
KEGG IDC06575
UniProt IDNot Available
OMIM ID
ChEBI ID28768
BioCyc IDCPD-1001
CTD IDNot Available
Stitch IDNot Available
PDB IDMML
ACToR IDNot Available
Wikipedia LinkP-cymene
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
MSDSLink
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 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene. Decreases expression of NPC1L1 once activated by a ligand.
Gene Name:
PPARD
Uniprot ID:
Q03181
Molecular Weight:
49902.99 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.16 uMATG_PPARd_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]