ContaminantDB: p-Cymene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:20:42 UTC

Update Date

2026-04-17 19:50:21 UTC

Accession Number

CHEM003838

Identification

Common Name

p-Cymene

Class

Small Molecule

Description

Cymene, 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).

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Food Toxin
Household Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Isopropyl-4-methylbenzene	ChEBI
1-Methyl-4-(1-methylethyl)benzene	ChEBI
1-Methyl-4-(propan-2-yl)benzene	ChEBI
1-Methyl-4-isopropylbenzene	ChEBI
4-Cymene	ChEBI
4-Isopropyl-1-methylbenzene	ChEBI
4-Isopropyltoluene	ChEBI
4-Methyl-1-isopropylbenzene	ChEBI
Cymene	ChEBI
Isopropyltoluene	ChEBI
p-Cimene	ChEBI
p-Cymol	ChEBI
p-Isopropyltoluene	ChEBI
p-Methylcumene	ChEBI
p-Methylisopropylbenzene	ChEBI
Para-cymene	ChEBI
1-Isopropyl-4-methyl-benzene	HMDB
1-Methyl-4-(1-methylethyl)-benzene	HMDB
2-p-Tolylpropane	HMDB
4-Isopropylbenzyl radical	HMDB
4-Methyl-1-(propan-2-yl)benzene	HMDB
Camphogen	HMDB
Cymol	HMDB
Dolcymene	HMDB
P- Isopropylmethylbenzene	HMDB
P-Mentha-1,3,5-triene	HMDB
P-Methyl cumene	HMDB
P-Methyl-cumene	HMDB
Paracymene	HMDB
Paracymol	HMDB
4-Methylisopropylbenzene	PhytoBank

Chemical Formula

C₁₀H₁₄

Average Molecular Mass

134.222 g/mol

Monoisotopic Mass

134.110 g/mol

CAS Registry Number

99-87-6

IUPAC Name

1-methyl-4-(propan-2-yl)benzene

Traditional Name

cymene

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 Key

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

toluenes (CHEBI:28768 )
monoterpene (CHEBI:28768 )
Menthane monoterpenoids (C06575 )
Cyclic monoterpenes (C06575 )
Menthane monoterpenoids (LMPR0102090014 )
a monoterpenoid (CPD-1001 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Gas

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-68.9 °C
Boiling Point	177.1°C (350.8°F)
Solubility	0.0234 mg/mL at 25 °C

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	4.17	ALOGPS
logP	3.73	ChemAxon
logS	-3.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	45.29 m³·mol⁻¹	ChemAxon
Polarizability	17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-4900000000-f403355796ccc97b5011	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-3900000000-18fab12c9b06d75f28d4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-0900000000-146f5d56238ffde0a8d0	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-007x-4900000000-14f27e732fc9b57e0b12	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-4900000000-f403355796ccc97b5011	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-3900000000-18fab12c9b06d75f28d4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-0900000000-146f5d56238ffde0a8d0	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-007x-4900000000-14f27e732fc9b57e0b12	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-8900000000-176f8c1c70e1e67b3d82	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-94c1bdcd85003d97aefc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2900000000-5ed611e91a5f86fc7019	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbc-9700000000-f812cd4b0a2fcb99f91a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-3043af674a7adea6117a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-589b3edc66f090e075e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00lu-4900000000-9166f98044ef814ac56b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-f5fa2e4eafb73a2ce5ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-f5fa2e4eafb73a2ce5ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-0d66e02ef78a9a9bac9a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9800000000-f6dc3a9bc8c029e844ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-31308f391d491363333e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9000000000-0f55cd38142065afafc3	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-4900000000-c8d4189d8e9f124c75ad	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0005805

FooDB ID

FDB017358

Phenol Explorer ID

Not Available

KNApSAcK ID

C00003040

BiGG ID

Not Available

BioCyc ID

CPD-1001

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Fevre, 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

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11341314

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15508832

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17826989

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19040104

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24023812

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24421258

7. Fevre, 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

8. Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.

9. Fevre, 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

10. 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.

11. 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.

p-Cymene (CHEM003838)

Structure for CHEM003838: p-Cymene