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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-03-20 21:10:29 UTC
Update Date2019-07-31 22:49:29 UTC
HMDB IDHMDB0059924
Secondary Accession Numbers
  • HMDB59924
Metabolite Identification
Common Namep-Xylene
Descriptionp-Xylene, also known as p-methyltoluene or para-xylene, belongs to the class of organic compounds known as p-xylenes. These are aromatic compounds that contain a p-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 4-positions. p-Xylene is possibly neutral. Outside of the human body, p-Xylene is found, on average, in the highest concentration within black walnuts. p-Xylene has also been detected, but not quantified in, several different foods, such as parsley, green bell peppers, pepper (c. frutescens), cauliflowers, and yellow bell peppers. This could make p-xylene a potential biomarker for the consumption of these foods. The p stands for para, identifying the location of the methyl groups as across from one another. p-Xylene is a potentially toxic compound. For skin contact, the skin should be washed with soap and water. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur.
Structure
Data?1563865991
Synonyms
ValueSource
1,4-DimethylbenzeneChEBI
1,4-DimethylbenzolChEBI
4-MethyltolueneChEBI
4-XyleneChEBI
p-DimethylbenzeneChEBI
p-MethyltolueneChEBI
p-XylolChEBI
PARA-xyleneChEBI
1,4-XyleneHMDB
ParaxyleneHMDB
Chemical FormulaC8H10
Average Molecular Weight106.165
Monoisotopic Molecular Weight106.07825032
IUPAC Name1,4-xylene
Traditional Namepara-xylene
CAS Registry NumberNot Available
SMILES
CC1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3
InChI KeyURLKBWYHVLBVBO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-xylenes. These are aromatic compounds that contain a p-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 4-positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct Parentp-Xylenes
Alternative Parents
Substituents
  • P-xylene
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP3.15ALOGPS
logP3ChemAxon
logS-2.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.14 m³·mol⁻¹ChemAxon
Polarizability13.12 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]+121.93531661259
DarkChem[M-H]-119.21231661259
DeepCCS[M+H]+126.61630932474
DeepCCS[M-H]-123.17330932474
DeepCCS[M-2H]-160.09330932474
DeepCCS[M+Na]+135.24930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-XyleneCC1=CC=C(C)C=C11196.5Standard polar33892256
p-XyleneCC1=CC=C(C)C=C1862.8Standard non polar33892256
p-XyleneCC1=CC=C(C)C=C1853.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - p-Xylene EI-B (Non-derivatized)splash10-052f-9400000000-4b2097f841009fc7a1f92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Xylene EI-B (Non-derivatized)splash10-052f-9400000000-58e5d57804187b27c6c52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Xylene CI-B (Non-derivatized)splash10-0a4i-0900000000-3bf7450495bd2c1b9ae32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Xylene EI-B (Non-derivatized)splash10-052f-9400000000-4b2097f841009fc7a1f92018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Xylene EI-B (Non-derivatized)splash10-052f-9400000000-58e5d57804187b27c6c52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Xylene CI-B (Non-derivatized)splash10-0a4i-0900000000-3bf7450495bd2c1b9ae32018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Xylene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-1ec9768719ddef2a0c602017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Xylene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Xylene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9500000000-313b5b919e2804de352e2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 10V, Positive-QTOFsplash10-0a4i-0900000000-4772806c99a8f48026de2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 20V, Positive-QTOFsplash10-0a4i-0900000000-8925e888b29ad16f979b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 40V, Positive-QTOFsplash10-0pdi-9300000000-cad6676e80b49deb4ca32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 10V, Negative-QTOFsplash10-0a4i-0900000000-987fa9bb840efccd55d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 20V, Negative-QTOFsplash10-0a4i-0900000000-987fa9bb840efccd55d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 40V, Negative-QTOFsplash10-0a4i-4900000000-5f8059855d9428f651592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 10V, Positive-QTOFsplash10-0a4i-4900000000-4ad4cb819bede18f8cf02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 20V, Positive-QTOFsplash10-004i-9100000000-cd6c0b30c7e9933348f52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 40V, Positive-QTOFsplash10-0fvl-9000000000-a902105af7410297b68e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 10V, Negative-QTOFsplash10-0a4i-0900000000-861947f0491f909a25882021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 20V, Negative-QTOFsplash10-0a4i-0900000000-861947f0491f909a25882021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Xylene 40V, Negative-QTOFsplash10-0a4i-3900000000-e442490a7749a4a80a2a2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not SpecifiedAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
Associated Disorders and Diseases
Disease References
Asthma
  1. Dallinga JW, Robroeks CM, van Berkel JJ, Moonen EJ, Godschalk RW, Jobsis Q, Dompeling E, Wouters EF, van Schooten FJ: Volatile organic compounds in exhaled breath as a diagnostic tool for asthma in children. Clin Exp Allergy. 2010 Jan;40(1):68-76. doi: 10.1111/j.1365-2222.2009.03343.x. Epub 2009 Sep 28. [PubMed:19793086 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005820
KNApSAcK IDNot Available
Chemspider ID7521
KEGG Compound IDC06756
BioCyc IDCPD-1422
BiGG IDNot Available
Wikipedia LinkP-Xylene
METLIN IDNot Available
PubChem Compound7809
PDB IDNot Available
ChEBI ID27417
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Schneider CJ, Moubaraki B, Cashion JD, Turner DR, Leita BA, Batten SR, Murray KS: Spin crossover in di-, tri- and tetranuclear, mixed-ligand tris(pyrazolyl)methane iron(II) complexes. Dalton Trans. 2011 Jul 14;40(26):6939-51. doi: 10.1039/c0dt01725f. Epub 2011 Jun 6. [PubMed:21643603 ]
  2. Grunder S, Valente C, Whalley AC, Sampath S, Portmann J, Botros YY, Stoddart JF: Molecular gauge blocks for building on the nanoscale. Chemistry. 2012 Dec 3;18(49):15632-49. doi: 10.1002/chem.201201985. Epub 2012 Oct 22. [PubMed:23090871 ]
  3. Latrache H, El GA, Karroua M, Hakkou A, Ait MH, El BA, Bourlioux P: Relations between hydrophobicity tested by three methods and surface chemical composition of Escherichia coli. New Microbiol. 2002 Jan;25(1):75-82. [PubMed:11837394 ]
  4. Lyons TW, Guironnet D, Findlater M, Brookhart M: Synthesis of p-xylene from ethylene. J Am Chem Soc. 2012 Sep 26;134(38):15708-11. Epub 2012 Sep 13. [PubMed:22934909 ]
  5. Grunder S, Stoddart JF: Giving substance to the Losanitsch series. Chem Commun (Camb). 2012 Mar 28;48(26):3158-60. doi: 10.1039/c2cc17734j. Epub 2012 Feb 16. [PubMed:22343755 ]
  6. Svecova V, Topinka J, Solansky I, Sram RJ: Personal exposure to volatile organic compounds in the Czech Republic. J Expo Sci Environ Epidemiol. 2012 Sep;22(5):455-60. doi: 10.1038/jes.2012.30. Epub 2012 Jun 6. [PubMed:22669500 ]
  7. Kirimura K, Nakagawa H, Tsuji K, Matsuda K, Kurane R, Usami S: Selective and continuous degradation of carbazole contained in petroleum oil by resting cells of Sphingomonas sp. CDH-7. Biosci Biotechnol Biochem. 1999 Sep;63(9):1563-8. [PubMed:10540744 ]