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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 18:57:44 UTC
Update Date2019-07-31 22:49:37 UTC
HMDB IDHMDB0034168
Secondary Accession Numbers
  • HMDB34168
Metabolite Identification
Common NameToluene
DescriptionToluene, also known as methylbenzene or phenylmethane, belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group. Toluene is a drug which is used for the removal of ascarids (toxocara canis and toxascaris leonina) and hookworms (ancylostoma caninum and uncinaria stenocephala) and as an aid in removing tapeworms (taenia pisiformis, dipylidium caninum, and echinococcus granulosus) from dogs and cats. Toluene is possibly neutral. Toluene exists in all living species, ranging from bacteria to humans. Toluene is a sweet and paint tasting compound. Outside of the human body, Toluene is found, on average, in the highest concentration within a few different foods, such as black walnuts, rosemaries, and corianders and in a lower concentration in milk (cow) and kohlrabis. Toluene has also been detected, but not quantified in, several different foods, such as prickly pears, citrus, yellow bell peppers, apples, and garden tomato (var.). This could make toluene a potential biomarker for the consumption of these foods. Toluene is a potentially toxic compound. Toluene, with regard to humans, has been found to be associated with several diseases such as pervasive developmental disorder not otherwise specified, perillyl alcohol administration for cancer treatment, autism, and asthma; toluene has also been linked to the inborn metabolic disorder celiac disease. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). In serious cases, atropine and/or pralidoxime should be administered. 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?1563862521
Synonyms
ValueSource
MethylbenzeneChEBI
PhenylmethaneChEBI
ToluenChEBI
ToluolChEBI
Methyl-benzeneHMDB
Methylbenzene, 9ciHMDB
MethylbenzolHMDB
Monomethyl benzeneHMDB
Phenyl-methaneHMDB
Chemical FormulaC7H8
Average Molecular Weight92.1384
Monoisotopic Molecular Weight92.062600256
IUPAC Nametoluene
Traditional Nametoluene
CAS Registry Number108-88-3
SMILES
CC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
InChI KeyYXFVVABEGXRONW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentToluenes
Alternative Parents
Substituents
  • Toluene
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Environmental role:

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-95 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.53 mg/mL at 25 °CNot Available
LogP2.73Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
logP2.56ALOGPS
logP2.49ChemAxon
logS-2.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.1 m³·mol⁻¹ChemAxon
Polarizability10.97 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)splash10-0006-9000000000-21366c9a473a72238c27Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-52239a45c9c9b566eb6bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-9484aa3a95c9d0168f91Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0006-9200000000-40a95d60297275bbf5b7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-21366c9a473a72238c27Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-52239a45c9c9b566eb6bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-9484aa3a95c9d0168f91Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0006-9200000000-40a95d60297275bbf5b7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-4e58dd253dfd47768489Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-1f40b8989b6d02b683a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-55a3cd8f1a8934fefca2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-32369d8d8789022995d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-ac6c69ea19d94fcc4befSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-ac6c69ea19d94fcc4befSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-65b85e7431f79c0337cfSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-93f195a62ea6129f7e07Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Breath
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00160 (0.00144-0.00177) uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
BloodDetected and Quantified0.00119 (0.00106-0.00132) uMChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
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
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not Quantified Children (1-13 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not Quantified Adult (>18 years old)BothAsthma 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
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 Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Children (1-13 years old)Bothautistic details
FecesDetected but not Quantified Children (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Treated celiac disease
details
SalivaDetected but not Quantified Children (1-13 years old)BothCeliac disease details
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Asthma
  1. Dragonieri S, Schot R, Mertens BJ, Le Cessie S, Gauw SA, Spanevello A, Resta O, Willard NP, Vink TJ, Rabe KF, Bel EH, Sterk PJ: An electronic nose in the discrimination of patients with asthma and controls. J Allergy Clin Immunol. 2007 Oct;120(4):856-62. doi: 10.1016/j.jaci.2007.05.043. Epub 2007 Jul 20. [PubMed:17658592 ]
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 ]
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
  2. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Perillyl alcohol administration for cancer treatment
  1. 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
DrugBank IDDB11558
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012454
KNApSAcK IDNot Available
Chemspider ID1108
KEGG Compound IDC01455
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkToluene
METLIN IDNot Available
PubChem Compound1140
PDB IDMBN
ChEBI ID17578
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Biegert T, Fuchs G, Heider J: Evidence that anaerobic oxidation of toluene in the denitrifying bacterium Thauera aromatica is initiated by formation of benzylsuccinate from toluene and fumarate. Eur J Biochem. 1996 Jun 15;238(3):661-8. [PubMed:8706665 ]
  2. Hougaard KS, Hansen AM, Hass U, Lund SP: Toluene depresses plasma corticosterone in pregnant rats. Pharmacol Toxicol. 2003 Mar;92(3):148-52. [PubMed:12753431 ]
  3. Tas U, Ogeturk M, Meydan S, Kus I, Kuloglu T, Ilhan N, Kose E, Sarsilmaz M: Hepatotoxic activity of toluene inhalation and protective role of melatonin. Toxicol Ind Health. 2011 Jun;27(5):465-73. doi: 10.1177/0748233710389853. Epub 2011 Feb 22. [PubMed:21343225 ]
  4. Aono J, Takimoto E, Komatsu T, Takeda A, Ueda W, Hirakawa M: [Anesthetic care of a patient intoxicated with thinner]. Masui. 1990 Mar;39(3):388-90. [PubMed:2345401 ]
  5. Win-Shwe TT, Mitsushima D, Nakajima D, Ahmed S, Yamamoto S, Tsukahara S, Kakeyama M, Goto S, Fujimaki H: Toluene induces rapid and reversible rise of hippocampal glutamate and taurine neurotransmitter levels in mice. Toxicol Lett. 2007 Jan 10;168(1):75-82. Epub 2006 Dec 4. [PubMed:17145141 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .