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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:30:22 UTC

Update Date

2023-02-21 17:23:34 UTC

HMDB ID

HMDB0033746

Secondary Accession Numbers

HMDB33746

Metabolite Identification

Common Name

Benzenethiol

Description

Benzenethiol 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Mercaptobenzene	ChEBI
Phenyl mercaptan	ChEBI
Phenylthiol	ChEBI
FEMA 3616	HMDB
mercapto-Benzene	HMDB
Phenylmercaptan	HMDB
Sodium benzenethiolate	HMDB
thio-Phenol	HMDB
Thiofenol	HMDB
Thiophenate	HMDB, MeSH
Thiophenol	HMDB, MeSH
Thiophenol, potassium salt	MeSH, HMDB
Thiophenol, sodium salt	MeSH, HMDB
Thiophenol, copper (+1) salt	MeSH, HMDB
Benzenethiol	MeSH

Chemical Formula

C₆H₆S

Average Molecular Weight

110.177

Monoisotopic Molecular Weight

110.019020882

IUPAC Name

benzenethiol

Traditional Name

thiophenol

CAS Registry Number

108-98-5

SMILES

SC1=CC=CC=C1

InChI Identifier

InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H

InChI Key

RMVRSNDYEFQCLF-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Thiophenols

Sub Class

Not Available

Direct Parent

Thiophenols

Alternative Parents

Substituents

Thiophenol
Monocyclic benzene moiety
Arylthiol
Hydrocarbon derivative
Organosulfur compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aryl thiol (CHEBI:48498 )

Ontology

Cellular substructure

Membrane (HMDB: HMDB0033746)
Cell membrane (HMDB: HMDB0033746)

Source

Exogenous

Exogenous (HMDB: HMDB0033746)

Food

Food (HMDB: HMDB0033746)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033746)

Biological role

Nutrient (HMDB: HMDB0033746)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-14.8 °C	Not Available
Boiling Point	169.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.84 mg/mL at 25 °C	Not Available
LogP	2.52	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.17 g/L	ALOGPS
logP	2.26	ALOGPS
logP	2.07	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	6.64	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	34.07 m³·mol⁻¹	ChemAxon
Polarizability	11.93 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	119.239	31661259
DarkChem	[M-H]-	114.977	31661259
DeepCCS	[M+H]+	120.0	30932474
DeepCCS	[M-H]-	117.385	30932474
DeepCCS	[M-2H]-	153.676	30932474
DeepCCS	[M+Na]+	128.405	30932474
AllCCS	[M+H]+	120.1	32859911
AllCCS	[M+H-H2O]+	115.1	32859911
AllCCS	[M+NH4]+	124.8	32859911
AllCCS	[M+Na]+	126.2	32859911
AllCCS	[M-H]-	117.3	32859911
AllCCS	[M+Na-2H]-	120.4	32859911
AllCCS	[M+HCOO]-	123.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzenethiol	SC1=CC=CC=C1	1490.9	Standard polar	33892256
Benzenethiol	SC1=CC=CC=C1	972.0	Standard non polar	33892256
Benzenethiol	SC1=CC=CC=C1	966.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzenethiol,1TMS,isomer #1	C[Si](C)(C)SC1=CC=CC=C1	1229.2	Semi standard non polar	33892256
Benzenethiol,1TMS,isomer #1	C[Si](C)(C)SC1=CC=CC=C1	1151.2	Standard non polar	33892256
Benzenethiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC1=CC=CC=C1	1488.3	Semi standard non polar	33892256
Benzenethiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC1=CC=CC=C1	1382.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Benzenethiol EI-B (Non-derivatized)	splash10-03di-8900000000-f00b12d067160b203ec9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzenethiol EI-B (Non-derivatized)	splash10-03xr-9400000000-963c74e11e0fee28cded	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzenethiol EI-B (Non-derivatized)	splash10-03di-8900000000-f00b12d067160b203ec9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzenethiol EI-B (Non-derivatized)	splash10-03xr-9400000000-963c74e11e0fee28cded	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzenethiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9500000000-39461b1b5833a05c75b9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzenethiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzenethiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 10V, Positive-QTOF	splash10-03di-0900000000-902e432c58a5b48af6d9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 20V, Positive-QTOF	splash10-03di-1900000000-d103552d249a6486076c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 40V, Positive-QTOF	splash10-014i-9000000000-73bb0429feae5d758aaf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 10V, Negative-QTOF	splash10-0a4i-0900000000-08819ed59079e9d5777a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 20V, Negative-QTOF	splash10-0a4i-0900000000-cf3fe95c00ee01bcc740	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 40V, Negative-QTOF	splash10-0a4i-3900000000-0744499c38c462f82335	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 10V, Positive-QTOF	splash10-03di-0900000000-c97d421ad73111f833c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 20V, Positive-QTOF	splash10-02t9-9300000000-1e8a6992b5b9f0c1bf07	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 40V, Positive-QTOF	splash10-0v00-9200000000-bbfc0b211357cbad29c7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 10V, Negative-QTOF	splash10-0a4i-0900000000-9604afb1cae23bc5502c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 20V, Negative-QTOF	splash10-0a4i-0900000000-9604afb1cae23bc5502c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenethiol 40V, Negative-QTOF	splash10-0a4i-0900000000-51cfb1d93a171cc439c0	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011878

KNApSAcK ID

Not Available

Chemspider ID

7681

KEGG Compound ID

Not Available

BioCyc ID

CPD-8132

BiGG ID

Not Available

Wikipedia Link

Thiophenol

METLIN ID

Not Available

PubChem Compound

7969

PDB ID

BT6

ChEBI ID

48498

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1007501

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Benzenethiol (HMDB0033746)

MOL for HMDB0033746 (Benzenethiol)

3D MOL for HMDB0033746 (Benzenethiol)

3D SDF for HMDB0033746 (Benzenethiol)

3D-SDF for HMDB0033746 (Benzenethiol)

PDB for HMDB0033746 (Benzenethiol)

3D PDB for HMDB0033746 (Benzenethiol)

SMILES for HMDB0033746 (Benzenethiol)

INCHI for HMDB0033746 (Benzenethiol)

Structure for HMDB0033746 (Benzenethiol)

3D Structure for HMDB0033746 (Benzenethiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra