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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2013-03-07 21:32:59 UTC
Update Date2019-07-23 07:13:03 UTC
HMDB IDHMDB0059851
Secondary Accession Numbers
  • HMDB59851
Metabolite Identification
Common Nameo-Xylene
Descriptiono-Xylene, also known as O-dimethylbenzene or O-methyltoluene, belongs to the class of organic compounds known as o-xylenes. These are aromatic compounds that contain a o-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 2-positions. o-Xylene is possibly neutral. o-Xylene is a geranium tasting compound. Outside of the human body, o-Xylene is found, on average, in the highest concentration within black walnuts. o-Xylene has also been detected, but not quantified in, several different foods, such as sweet cherries, cucumbers, evergreen blackberries, corns, and cauliflowers. This could make O-xylene a potential biomarker for the consumption of these foods. o-Xylene is a potentially toxic compound.
Structure
Data?1563865983
Synonyms
ValueSource
1,2-DimethylbenzeneChEBI
1,2-DimethylbenzolChEBI
2-XyleneChEBI
3,4-XyleneChEBI
O-DimethylbenzeneChEBI
O-MethyltolueneChEBI
O-XylolChEBI
ORTHO-xyleneChEBI
1,2-XyleneHMDB
Chemical FormulaC8H10
Average Molecular Weight106.165
Monoisotopic Molecular Weight106.07825032
IUPAC Name1,2-xylene
Traditional Nameortho-xylene
CAS Registry NumberNot Available
SMILES
CC1=CC=CC=C1C
InChI Identifier
InChI=1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3
InChI KeyCTQNGGLPUBDAKN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-xylenes. These are aromatic compounds that contain a o-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 2-positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct Parento-Xylenes
Alternative Parents
Substituents
  • O-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:

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
logP3.16ALOGPS
logP3ChemAxon
logS-2.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.14 m³·mol⁻¹ChemAxon
Polarizability12.96 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)splash10-0006-9200000000-91162619463de43f7b46Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9300000000-7444c78cfa46f8a9a90eSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-0900000000-f15325822f4f50e0f099Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-91162619463de43f7b46Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9300000000-7444c78cfa46f8a9a90eSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-0900000000-f15325822f4f50e0f099Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7900000000-392b6abb89b281539432Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-7dfff6875bd00f609d90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-89860e0d53bc8dcf7d90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbf-9100000000-c253aaa68babc1381810Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-f15589460cfaed631148Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-f15589460cfaed631148Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-a4303e6414e4609396f5Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9300000000-9030a9b0de39df7365ccSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000358 (0.000320-0.000414) uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
BloodDetected and Quantified0.000301 (0.000264-0.000377) uMChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
FecesDetected 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
FecesDetected 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)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)BothNormal 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
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Children (1-13 years old)BothAutism details
FecesDetected but not Quantified Children (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified 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
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
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 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005819
KNApSAcK IDNot Available
Chemspider ID6967
KEGG Compound IDC07212
BioCyc IDCPD-1421
BiGG IDNot Available
Wikipedia LinkO-Xylene
METLIN IDNot Available
PubChem Compound7237
PDB IDNot Available
ChEBI ID28063
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Han QJ, Wu HL, Cai CB, Tang LJ, Yu RQ: Using near-infrared spectroscopy and differential adsorption bed method to study adsorption kinetics of orthoxylene on silica gel. Talanta. 2008 Aug 15;76(4):752-7. doi: 10.1016/j.talanta.2008.04.021. Epub 2008 Apr 20. [PubMed:18656653 ]
  2. Silaev MM: [New kinetic model of the radical-chain oxidation, including competitive reactions: oxygen as an autoinhibitor]. Biofizika. 2001 Mar-Apr;46(2):203-9. [PubMed:11357330 ]
  3. van Beelen P, Fleuren-Kemila AK: Toxic effects of pentachlorophenol and other pollutants on the mineralization of acetate in several soils. Ecotoxicol Environ Saf. 1993 Aug;26(1):10-7. [PubMed:7691530 ]