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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2007-01-22 23:51:51 UTC

Update Date

2022-03-07 02:49:29 UTC

HMDB ID

HMDB0005805

Secondary Accession Numbers

HMDB05805

Metabolite Identification

Common Name

p-Cymene

Description

Cymene, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

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 Weight

134.222

Monoisotopic Molecular Weight

134.109550451

IUPAC Name

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

Traditional Name

cymene

CAS Registry Number

99-87-6

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 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 )

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 22284503)

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005805)

Source

Endogenous

Endogenous (HMDB: HMDB0005805)

Plant

Plant (HMDB: HMDB0005805)
Cucurbitaceae (HMDB: HMDB0005805)

Exogenous

Food

Food (HMDB: HMDB0005805)

Fruit

Drupe

Apricot (FooDB: FOOD00144)

Berry

Other fruit

Fig (FooDB: FOOD00081)

Citrus

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Pummelo (FooDB: FOOD00055)
Citrus (FooDB: FOOD00859)

Vegetable

Root vegetable

Fruit vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Safflower (FooDB: FOOD00042)
Sunflower (FooDB: FOOD00086)

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Gourd

Bitter gourd (FooDB: FOOD00115)

Exogenous (HMDB: HMDB0005805)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0005805)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0005805)

Lipid metabolism pathway (HMDB: HMDB0005805)

Cellular process

Cell signaling (HMDB: HMDB0005805)

Biochemical process

Lipid transport (HMDB: HMDB0005805)

Role

Industrial applicationBiological role

Modulator

Inhibitor

EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0005805)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-68.9 °C	Not Available
Boiling Point	176.00 to 178.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.023 mg/mL at 25 °C	Not Available
LogP	4.10	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.616	31661259
DarkChem	[M-H]-	129.844	31661259
DeepCCS	[M+H]+	137.788	30932474
DeepCCS	[M-H]-	133.961	30932474
DeepCCS	[M-2H]-	171.375	30932474
DeepCCS	[M+Na]+	146.914	30932474
AllCCS	[M+H]+	123.8	32859911
AllCCS	[M+H-H2O]+	119.0	32859911
AllCCS	[M+NH4]+	128.3	32859911
AllCCS	[M+Na]+	129.5	32859911
AllCCS	[M-H]-	129.2	32859911
AllCCS	[M+Na-2H]-	130.9	32859911
AllCCS	[M+HCOO]-	132.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.86 minutes	32390414
Predicted by Siyang on May 30, 2022	18.1053 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.66 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2203.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	685.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	264.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	461.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	803.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	757.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	231.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1561.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	625.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1624.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	537.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	484.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	552.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	462.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	26.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Cymene	CC(C)C1=CC=C(C)C=C1	1283.2	Standard polar	33892256
p-Cymene	CC(C)C1=CC=C(C)C=C1	1030.7	Standard non polar	33892256
p-Cymene	CC(C)C1=CC=C(C)C=C1	1012.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - p-Cymene EI-B (Non-derivatized)	splash10-014i-4900000000-f403355796ccc97b5011	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Cymene EI-B (Non-derivatized)	splash10-014i-3900000000-18fab12c9b06d75f28d4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Cymene EI-B (Non-derivatized)	splash10-001i-0900000000-146f5d56238ffde0a8d0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Cymene CI-B (Non-derivatized)	splash10-007x-4900000000-14f27e732fc9b57e0b12	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Cymene EI-B (Non-derivatized)	splash10-014i-4900000000-f403355796ccc97b5011	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Cymene EI-B (Non-derivatized)	splash10-014i-3900000000-18fab12c9b06d75f28d4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Cymene EI-B (Non-derivatized)	splash10-001i-0900000000-146f5d56238ffde0a8d0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Cymene CI-B (Non-derivatized)	splash10-007x-4900000000-14f27e732fc9b57e0b12	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Cymene GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-8900000000-176f8c1c70e1e67b3d82	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Cymene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-4900000000-c8d4189d8e9f124c75ad	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 10V, Positive-QTOF	splash10-000i-0900000000-94c1bdcd85003d97aefc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 20V, Positive-QTOF	splash10-000i-2900000000-5ed611e91a5f86fc7019	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 40V, Positive-QTOF	splash10-0gbc-9700000000-f812cd4b0a2fcb99f91a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 10V, Negative-QTOF	splash10-001i-0900000000-3043af674a7adea6117a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 20V, Negative-QTOF	splash10-001i-0900000000-589b3edc66f090e075e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 40V, Negative-QTOF	splash10-00lu-4900000000-9166f98044ef814ac56b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 10V, Negative-QTOF	splash10-001i-0900000000-f5fa2e4eafb73a2ce5ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 20V, Negative-QTOF	splash10-001i-0900000000-f5fa2e4eafb73a2ce5ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 40V, Negative-QTOF	splash10-00kf-9200000000-0d66e02ef78a9a9bac9a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 10V, Positive-QTOF	splash10-000f-9800000000-f6dc3a9bc8c029e844ff	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 20V, Positive-QTOF	splash10-0006-9100000000-31308f391d491363333e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cymene 40V, Positive-QTOF	splash10-002f-9000000000-0f55cd38142065afafc3	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Breast cancer	22284503	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
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 IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

P-cymene

METLIN ID

Not Available

PubChem Compound

7463

PDB ID

Not Available

ChEBI ID

28768

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1032712

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

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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 ]

Showing metabocard for p-Cymene (HMDB0005805)

MOL for HMDB0005805 (p-Cymene)

3D MOL for HMDB0005805 (p-Cymene)

3D SDF for HMDB0005805 (p-Cymene)

3D-SDF for HMDB0005805 (p-Cymene)

PDB for HMDB0005805 (p-Cymene)

3D PDB for HMDB0005805 (p-Cymene)

SMILES for HMDB0005805 (p-Cymene)

INCHI for HMDB0005805 (p-Cymene)

Structure for HMDB0005805 (p-Cymene)

3D Structure for HMDB0005805 (p-Cymene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra