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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-03-20 21:10:58 UTC
Update Date2019-07-23 07:13:12 UTC
HMDB IDHMDB0059933
Secondary Accession Numbers
  • HMDB59933
Metabolite Identification
Common Namep-Toluenesulfonic acid
Descriptionp-Toluenesulfonic acid, also known as tosylate or para-toluene sulfonate, is a member of the class of compounds known as p-methylbenzenesulfonates. p-Methylbenzenesulfonates are benzenesulfonic acids (or derivative thereof) carrying a methyl group at the para- position. p-Toluenesulfonic acid is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). p-Toluenesulfonic acid (PTSA or pTsOH) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H. It is a white solid that is soluble in water, alcohols, and other polar organic solvents. The CH3C6H4SO2– group is known as the tosyl group and is often abbreviated as Ts or Tos. Most often, TsOH refers to the monohydrate, TsOH•H2O. It is a white solid that is soluble in water, alcohols, and other polar organic solvents (Wikipedia).
Structure
Data?1563865992
Synonyms
ValueSource
4-Toluenesulfonic acidChEBI
p-Methylbenzenesulfonic acidChEBI
p-Methylphenylsulfonic acidChEBI
p-Toluenesulfonic acidChEBI
p-Toluenesulphonic acidChEBI
p-Tolylsulfonic acidChEBI
PARA-toluene sulfonATEChEBI
Toluen-4-sulfonsaeureChEBI
Toluene-4-sulfonateChEBI
Tosic acidChEBI
TosylateChEBI
Tosylic acidChEBI
4-ToluenesulfonateGenerator
4-ToluenesulphonateGenerator
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p-MethylphenylsulphonateGenerator
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p-ToluenesulfonateGenerator
p-ToluenesulphonateGenerator
p-TolylsulfonateGenerator
p-TolylsulphonateGenerator
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PARA-toluene sulfonic acidGenerator
PARA-toluene sulphonateGenerator
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Toluen-4-sulphonsaeureGenerator
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TosateGenerator
4-MethylbenzenesulfonateGenerator
4-MethylbenzenesulphonateGenerator
4-Methylbenzenesulphonic acidGenerator
4-Toluene sulfonateMeSH
4-Toluenesulfonic acid ammonium saltMeSH
4-Toluenesulfonic acid monohydrateMeSH
4-Toluenesulfonic acid, calcium saltMeSH
4-Toluenesulfonic acid, copper (2+) saltMeSH
4-Toluenesulfonic acid, ion (1+)MeSH
4-Toluenesulfonic acid, lithium saltMeSH
4-Toluenesulfonic acid, magnesium saltMeSH
4-Toluenesulfonic acid, potassium saltMeSH
4-Toluenesulfonic acid, rubidium saltMeSH
4-Toluenesulfonic acid, silver (+1) saltMeSH
4-Toluenesulfonic acid, sodium saltMeSH
4-Toluenesulfonic acid, zinc saltMeSH
p-Toluene sulfonateMeSH
p-Toluene sulphonic acidMeSH
p-Toluenesulfonate pyridiniumMeSH
Para-toluenesulfonic acidMeSH
4-Methylbenzenesulfonic acidHMDB
Chemical FormulaC7H8O3S
Average Molecular Weight172.202
Monoisotopic Molecular Weight172.019414812
IUPAC Name4-methylbenzene-1-sulfonic acid
Traditional Nametoluenesulfonic acid
CAS Registry Number104-15-4
SMILES
CC1=CC=C(C=C1)S(O)(=O)=O
InChI Identifier
InChI=1S/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10)
InChI KeyJOXIMZWYDAKGHI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as p-methylbenzenesulfonates. These are benzenesulfonic acids (or derivative thereof) carrying a methyl group at the para- position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonic acids and derivatives
Direct Parentp-Methylbenzenesulfonates
Alternative Parents
Substituents
  • P-methylbenzenesulfonate
  • Tosyl compound
  • Benzenesulfonyl group
  • 1-sulfo,2-unsubstituted aromatic compound
  • Arylsulfonic acid or derivatives
  • Toluene
  • Sulfonyl
  • Organosulfonic acid
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

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 Solubility2.3 g/LALOGPS
logP-0.88ALOGPS
logP1.67ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.72 m³·mol⁻¹ChemAxon
Polarizability16.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004m-7970000000-1d52a5deeb555385dd84Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004m-7970000000-1d52a5deeb555385dd84Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-938ee4a29fd12e145c3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-d0b1914485d9ea6a8ed1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-74933fb0a0cfaed5004fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-9100000000-e58b15b2e4247f942ffdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-297c45510f8bcc2c7332Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-10b19a616e398d436d3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-a5047b754e5ca626159bSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03120
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06677
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6101
PDB IDNot Available
ChEBI ID27849
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Green RA, Lovell NH, Poole-Warren LA: Cell attachment functionality of bioactive conducting polymers for neural interfaces. Biomaterials. 2009 Aug;30(22):3637-44. doi: 10.1016/j.biomaterials.2009.03.043. Epub 2009 Apr 16. [PubMed:19375160 ]
  2. Kim EG, Bredas JL: Electronic evolution of poly(3,4-ethylenedioxythiophene) (PEDOT): from the isolated chain to the pristine and heavily doped crystals. J Am Chem Soc. 2008 Dec 17;130(50):16880-9. doi: 10.1021/ja806389b. [PubMed:19053439 ]
  3. Green RA, Hassarati RT, Bouchinet L, Lee CS, Cheong GL, Yu JF, Dodds CW, Suaning GJ, Poole-Warren LA, Lovell NH: Substrate dependent stability of conducting polymer coatings on medical electrodes. Biomaterials. 2012 Sep;33(25):5875-86. doi: 10.1016/j.biomaterials.2012.05.017. Epub 2012 May 30. [PubMed:22656446 ]
  4. Marinescu SC, Winkler JR, Gray HB: Molecular mechanisms of cobalt-catalyzed hydrogen evolution. Proc Natl Acad Sci U S A. 2012 Sep 18;109(38):15127-31. Epub 2012 Sep 4. [PubMed:22949704 ]
  5. Jiang J, Pan X, Cao J, Jiang J, Hua D, Zhu X: Synthesis and property of chitosan graft copolymer by RAFT polymerization with tosylic acid-chitosan complex. Int J Biol Macromol. 2012 Apr 1;50(3):586-90. doi: 10.1016/j.ijbiomac.2012.01.033. Epub 2012 Feb 1. [PubMed:22322112 ]