Showing Compound Card for o-Xylene (CDB000559)

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Record Information
Version1.0
Created at2020-03-19 00:43:42 UTC
Updated at2020-12-07 19:07:31 UTC
CannabisDB IDCDB000559
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nameo-Xylene
DescriptionOrtho-xylene, o-xylene or 1,2-dimethylbenzen is a member of the class of organic compounds called xylenes. Xylenes are aromatic compounds that contain a benzene ring carrying two methyl groups at different positions around the ring. There are three types of xylene isomers, ortho, meta and para xylene. O-Xylene is a clear, colorless, highly flammable liquid that is not soluble in water. Most o-xylene is produced through the cracking of peteroleum. O-xylene is largely used in the production of phthalic anhydride, which is a precursor to many materials, drugs, and other chemicals (doi:10.1002/14356007.a28_433). O-Xylene has a geranium-like odor. In the plant kingdom o-xylene is found in black walnuts and papaya. It 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. Exposure to xylene can occur via inhalation, ingestion, eye or skin contact. It is primarily metabolized in the liver by oxidation of a methyl group and conjugation with glycine to yield methyl hippuric acid, which is then excreted in the urine. Smaller amounts are eliminated unchanged in the exhaled air (PMID: 21180450 ). If xylene is ingested one's mouth should be rinsed, and vomiting should not be induced. Exposure of pure xylene to eyes can cause redness and pain. Xylenes are not acutely toxic, for example the LD50 (rat, oral) is 4300 mg/kg. o-Xylene is one of the aromatic benzenoids identified in Cannabis sativa (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight106.17
Monoisotopic Molecular Weight106.0783
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

Indirect biological role:

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9300000000-9030a9b0de39df7365cc2014-09-20View Spectrum
GC-MSo-Xylene, non-derivatized, GC-MS Spectrumsplash10-0006-9200000000-91162619463de43f7b46Spectrum
GC-MSo-Xylene, non-derivatized, GC-MS Spectrumsplash10-052f-9300000000-7444c78cfa46f8a9a90eSpectrum
GC-MSo-Xylene, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-f15325822f4f50e0f099Spectrum
GC-MSo-Xylene, non-derivatized, GC-MS Spectrumsplash10-0006-9200000000-91162619463de43f7b46Spectrum
GC-MSo-Xylene, non-derivatized, GC-MS Spectrumsplash10-052f-9300000000-7444c78cfa46f8a9a90eSpectrum
GC-MSo-Xylene, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-f15325822f4f50e0f099Spectrum
Predicted GC-MSo-Xylene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-7900000000-392b6abb89b281539432Spectrum
Predicted GC-MSo-Xylene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSo-Xylene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-7dfff6875bd00f609d902016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-89860e0d53bc8dcf7d902016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbf-9100000000-c253aaa68babc13818102016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-f15589460cfaed6311482016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-f15589460cfaed6311482016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-a4303e6414e4609396f52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-baa6be6925cfc2a66ea32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6u-9300000000-60dd43e9895d0306f01a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-83e0928bd11f13cdad5d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-861947f0491f909a25882021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-861947f0491f909a25882021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-4705a212df4e296fd1c32021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0059851
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
References
General References
  1. Kandyala R, Raghavendra SP, Rajasekharan ST: Xylene: An overview of its health hazards and preventive measures. J Oral Maxillofac Pathol. 2010 Jan;14(1):1-5. doi: 10.4103/0973-029X.64299. [PubMed:21180450 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]