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Record Information
StatusExpected but not Quantified
Creation Date2012-09-11 18:30:22 UTC
Update Date2019-07-23 06:14:13 UTC
Secondary Accession Numbers
  • HMDB33746
Metabolite Identification
Common NameBenzenethiol
DescriptionBenzenethiol is a flavouring agent Thiophenol is a chemical compound with the formula C6H5SH, and sometimes abbreviated as PhSH. The foul-smelling liquid is the principal aromatic thiol. The chemical structures of thiophenols are analogous to phenols except the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, thio- commonly means that the oxygen atom is replaced by a sulfur atom. Thiophenols also describes a class of compounds formally derived from thiophenol itself. All have a sulfhydryl group (-SH) covalently bonded to an aromatic ring. The organosulfur ligand in medicine merthiolate is a thiophenol.
Phenyl mercaptanChEBI
Sodium benzenethiolateHMDB
ThiophenateHMDB, MeSH
ThiophenolHMDB, MeSH
Thiophenol, potassium saltMeSH, HMDB
Thiophenol, sodium saltMeSH, HMDB
Thiophenol, copper (+1) saltMeSH, HMDB
Chemical FormulaC6H6S
Average Molecular Weight110.177
Monoisotopic Molecular Weight110.019020882
IUPAC Namebenzenethiol
Traditional Namethiophenol
CAS Registry Number108-98-5
InChI Identifier
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiophenols. Thiophenols are compounds containing a thiophenol ring, which a phenol derivative obtained by replacing the oxygen atom from the hydroxyl group (attached to the benzene) by a sulfur atom.
KingdomOrganic compounds
Super ClassBenzenoids
Sub ClassNot Available
Direct ParentThiophenols
Alternative Parents
  • Thiophenol
  • Monocyclic benzene moiety
  • Arylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Biological location:



Industrial application:

Biological role:

Physical Properties
Experimental Molecular Properties
Melting Point-14.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.84 mg/mL at 25 °CNot Available
LogP2.52Not Available
Predicted Molecular Properties
Water Solubility1.17 g/LALOGPS
pKa (Strongest Acidic)6.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.07 m³·mol⁻¹ChemAxon
Polarizability11.93 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available119.23931661259
DarkChem[M-H]-PredictedNot Available114.97731661259

Retention Indices


Not Available


Not Available


Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-f00b12d067160b203ec92017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-9400000000-963c74e11e0fee28cded2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-f00b12d067160b203ec92018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-9400000000-963c74e11e0fee28cded2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9500000000-39461b1b5833a05c75b92017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-9500000000-39461b1b5833a05c75b92021-09-05View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312ab2021-09-18View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb62021-09-18View Spectrum


Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-902e432c58a5b48af6d92016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-d103552d249a6486076c2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-73bb0429feae5d758aaf2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-08819ed59079e9d5777a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-cf3fe95c00ee01bcc7402016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3900000000-0744499c38c462f823352016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-c97d421ad73111f833c12021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-9300000000-1e8a6992b5b9f0c1bf072021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9200000000-bbfc0b211357cbad29c72021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9604afb1cae23bc5502c2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-51cfb1d93a171cc439c02021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011878
KNApSAcK IDNot Available
Chemspider ID7681
KEGG Compound IDNot Available
BioCyc IDCPD-8132
BiGG IDNot Available
Wikipedia LinkThiophenol
METLIN IDNot Available
PubChem Compound7969
ChEBI ID48498
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Patil G, Rudolph R, Lange C: In vitro-refolding of a single-chain Fv fragment in the presence of heteroaromatic thiols. J Biotechnol. 2008 Apr 30;134(3-4):218-21. doi: 10.1016/j.jbiotec.2008.01.009. Epub 2008 Jan 18. [PubMed:18321603 ]
  2. Park G, Lee KG, Lee SJ, Park TJ, Wi R, Wang KW, Kim DH: Ultrasound-aided formation of gold nanoparticles on multi-walled carbon nanotubes functionalized with mercaptobenzene moieties. J Nanosci Nanotechnol. 2011 Jul;11(7):6222-6. [PubMed:22121689 ]
  3. Montanari L, Pavanetto F, Modena T, Mazza M: [Antifungal activity of diesters of 2-mercaptobenzene methanethiol]. Farmaco Sci. 1982 Nov;37(11):759-63. [PubMed:7152011 ]
  4. Barrese AA 3rd, Genis C, Fisher SZ, Orwenyo JN, Kumara MT, Dutta SK, Phillips E, Kiddle JJ, Tu C, Silverman DN, Govindasamy L, Agbandje-McKenna M, McKenna R, Tripp BC: Inhibition of carbonic anhydrase II by thioxolone: a mechanistic and structural study. Biochemistry. 2008 Mar 11;47(10):3174-84. doi: 10.1021/bi702385k. Epub 2008 Feb 12. [PubMed:18266323 ]
  5. SCHNITZER RJ, KELLY DR, SOO-HOO G, GRUNBERG E, UNGER C: Chemotherapeutic studies on a new stibonic acid, 2-carboxymethyl-mercaptobenzene stibonic acid, Ro 2-1160. Arch Int Pharmacodyn Ther. 1951 Jan;85(1-2):100-11. [PubMed:14820391 ]
  6. Harnisch JA, Pris AD, Porter MD: Attachment of gold nanoparticles to glassy carbon electrodes via a mercaptobenzene film. J Am Chem Soc. 2001 Jun 20;123(24):5829-30. [PubMed:11403628 ]
  7. WAGNER G, LENK C: [On the preparation and properties of amino-mercaptobenzene-N,S-bis-glycosides]. Arch Pharm. 1962 Jun;295/67:415-27. [PubMed:14004344 ]
  8. Hochalter JB, Wattenberg LW, Coccia JB, Galbraith AR: Inhibition of beta-propiolactone-induced neoplasia of the forestomach and large bowel by 4-mercaptobenzene sulfonate in mice and rats. Cancer Res. 1988 May 15;48(10):2740-3. [PubMed:3359434 ]
  9. Mirek J, Chojnacka-Wojcik E, Tatarzynska E, Wiczynska B: Synthesis of 3-phenyl-3-phenylthiopropionic acids, amides, amines and studies on their pharmacological properties. Farmaco Sci. 1985 Sep;40(9):701-8. [PubMed:4076432 ]
  10. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .