Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 18:30:22 UTC |
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Update Date | 2023-02-21 17:23:34 UTC |
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HMDB ID | HMDB0033746 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Benzenethiol |
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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. |
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Structure | InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H |
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Synonyms | Value | Source |
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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 |
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Chemical Formula | C6H6S |
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Average Molecular Weight | 110.177 |
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Monoisotopic Molecular Weight | 110.019020882 |
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IUPAC Name | benzenethiol |
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Traditional Name | thiophenol |
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CAS Registry Number | 108-98-5 |
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SMILES | SC1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H |
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InChI Key | RMVRSNDYEFQCLF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Thiophenols |
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Sub Class | Not Available |
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Direct Parent | Thiophenols |
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Alternative Parents | |
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Substituents | - Thiophenol
- Monocyclic benzene moiety
- Arylthiol
- Hydrocarbon derivative
- Organosulfur compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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 |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB011878 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 7681 |
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KEGG Compound ID | Not Available |
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BioCyc ID | CPD-8132 |
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BiGG ID | Not Available |
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Wikipedia Link | Thiophenol |
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METLIN ID | Not Available |
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PubChem Compound | 7969 |
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PDB ID | BT6 |
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ChEBI ID | 48498 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1007501 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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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.. .
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