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Record Information
Version4.0
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 in black walnuts. p-xylene has also been detected, but not quantified in, several different foods, such as pepper (c. annuum), green bell peppers, parsley, yellow bell peppers, and red bell peppers. This could make p-xylene a potential biomarker for the consumption of these foods. p-Xylene is a potentially toxic compound. In particular it is a component in the production of terephthalic acid for polyesters such as polyethylene terephthalate (generally known as PET). If p-xylene is ingested one's mouth should be rinsed and vomiting should not be induced. Exposure of p-xylene to eyes can cause redness and pain.
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

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Environmental role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9400000000-4b2097f841009fc7a1f9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9400000000-58e5d57804187b27c6c5Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-0900000000-3bf7450495bd2c1b9ae3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9400000000-4b2097f841009fc7a1f9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9400000000-58e5d57804187b27c6c5Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-0900000000-3bf7450495bd2c1b9ae3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-1ec9768719ddef2a0c60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-4772806c99a8f48026deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-8925e888b29ad16f979bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9300000000-cad6676e80b49deb4ca3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-987fa9bb840efccd55d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-987fa9bb840efccd55d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4900000000-5f8059855d9428f65159Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9500000000-313b5b919e2804de352eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not Quantified Children (1-13 years old)Not SpecifiedAsthma details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>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
FoodDB 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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  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 ]