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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:17:33 UTC
Update Date2023-02-21 17:24:15 UTC
HMDB IDHMDB0034448
Secondary Accession Numbers
  • HMDB34448
Metabolite Identification
Common NameMethyl phenyl sulfide
DescriptionMethyl phenyl sulfide, also known as (1-thiaethyl)benzene or (methylthio)benzene, belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group. Methyl phenyl sulfide is a solvent, spicy, and toluene tasting compound. Methyl phenyl sulfide has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), breakfast cereal, cereals and cereal products, herbs and spices, and robusta coffees (Coffea canephora). This could make methyl phenyl sulfide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Methyl phenyl sulfide.
Structure
Data?1677000255
Synonyms
ValueSource
(1-Thiaethyl)benzeneChEBI
(Methylthio)benzeneChEBI
1-Phenyl-1-thiaethaneChEBI
Methyl phenyl thioetherChEBI
MethylphenylsulfideChEBI
MethylthiobenzeneChEBI
Phenyl methyl sulfideChEBI
PhenylthiomethaneChEBI
MethylphenylsulphideGenerator
Phenyl methyl sulphideGenerator
Methyl phenyl sulphideGenerator
Methylsulfanyl-benzeneChEMBL, HMDB
Methylsulphanyl-benzeneGenerator, HMDB
(Methylsulfanyl)benzeneHMDB
(methylthio)-BenzeneHMDB
(methylthio)Benzene, 9ciHMDB
FEMA 3873HMDB
Methyl phenylsulfideHMDB
MethylmercaptobenzeneHMDB
Sulfide, methyl phenylHMDB
Sulfide, methyl phenyl (6ci,8ci)HMDB
thio-AnisoleHMDB
ThioanisolHMDB, MeSH
ThioanisoleHMDB
Methyl phenyl sulfideMeSH
Chemical FormulaC7H8S
Average Molecular Weight124.203
Monoisotopic Molecular Weight124.034670946
IUPAC Name(methylsulfanyl)benzene
Traditional Namethioanisole
CAS Registry Number100-68-5
SMILES
CSC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
InChI KeyHNKJADCVZUBCPG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThioethers
Sub ClassAryl thioethers
Direct ParentAryl thioethers
Alternative Parents
Substituents
  • Aryl thioether
  • Thiophenol ether
  • Alkylarylthioether
  • Benzenoid
  • Monocyclic benzene moiety
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-15 °CNot Available
Boiling Point188.00 to 193.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.51 mg/mL at 25 °CNot Available
LogP2.74Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP2.86ALOGPS
logP2.6ChemAxon
logS-2.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.82 m³·mol⁻¹ChemAxon
Polarizability13.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.84131661259
DarkChem[M-H]-121.60431661259
DeepCCS[M+H]+123.51230932474
DeepCCS[M-H]-120.69230932474
DeepCCS[M-2H]-157.2230932474
DeepCCS[M+Na]+131.88630932474
AllCCS[M+H]+121.932859911
AllCCS[M+H-H2O]+117.032859911
AllCCS[M+NH4]+126.432859911
AllCCS[M+Na]+127.732859911
AllCCS[M-H]-123.132859911
AllCCS[M+Na-2H]-125.532859911
AllCCS[M+HCOO]-128.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl phenyl sulfideCSC1=CC=CC=C11559.9Standard polar33892256
Methyl phenyl sulfideCSC1=CC=CC=C11045.5Standard non polar33892256
Methyl phenyl sulfideCSC1=CC=CC=C11114.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl phenyl sulfide EI-B (Non-derivatized)splash10-0fk9-9500000000-e5cde2928e0b7e33c1cc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl phenyl sulfide EI-B (Non-derivatized)splash10-0fk9-9500000000-e5cde2928e0b7e33c1cc2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl phenyl sulfide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9700000000-11fda9666ffc9c48ef852017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl phenyl sulfide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl phenyl sulfide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 10V, Positive-QTOFsplash10-004i-0900000000-7a2b7d600eac8b4321972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 20V, Positive-QTOFsplash10-004i-1900000000-2e4e71ca972a8dbea03b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 40V, Positive-QTOFsplash10-014i-9100000000-914f8ae63ade7b0e82252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 10V, Negative-QTOFsplash10-00b9-9700000000-90cfe5bbf335721813fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 20V, Negative-QTOFsplash10-00b9-9500000000-64a9a8207ef6b8e75a122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 40V, Negative-QTOFsplash10-0006-9000000000-98ccfcce7dba596c651a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 10V, Positive-QTOFsplash10-004i-0900000000-657e1439635c6222c9b52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 20V, Positive-QTOFsplash10-004i-4900000000-c3ab1655b883c8f684362021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 40V, Positive-QTOFsplash10-0fb9-9000000000-d65947711d78df83feb22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 10V, Negative-QTOFsplash10-00di-0900000000-56c97b9074caec5428fb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 20V, Negative-QTOFsplash10-00di-0900000000-cc45e695f23bb26199e92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenyl sulfide 40V, Negative-QTOFsplash10-006t-9200000000-67be3f05fa6b536406342021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012855
KNApSAcK IDNot Available
Chemspider ID7239
KEGG Compound IDNot Available
BioCyc IDCPD-14757
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7520
PDB IDNot Available
ChEBI ID134281
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1108231
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shen HM, Ji HB: Amino alcohol-modified beta-cyclodextrin inducing biomimetic asymmetric oxidation of thioanisole in water. Carbohydr Res. 2012 Jun 1;354:49-58. doi: 10.1016/j.carres.2012.03.034. Epub 2012 Apr 2. [PubMed:22541298 ]
  2. Park YS, Widawsky JR, Kamenetska M, Steigerwald ML, Hybertsen MS, Nuckolls C, Venkataraman L: Frustrated rotations in single-molecule junctions. J Am Chem Soc. 2009 Aug 12;131(31):10820-1. doi: 10.1021/ja903731m. [PubMed:19722660 ]
  3. Wang W, Xu Y, Wang DI, Li Z: Recyclable nanobiocatalyst for enantioselective sulfoxidation: facile fabrication and high performance of chloroperoxidase-coated magnetic nanoparticles with iron oxide core and polymer shell. J Am Chem Soc. 2009 Sep 16;131(36):12892-3. doi: 10.1021/ja905477j. [PubMed:19702305 ]
  4. Wan S, Li G, An T, Guo B: Co-treatment of single, binary and ternary mixture gas of ethanethiol, dimethyl disulfide and thioanisole in a biotrickling filter seeded with Lysinibacillus sphaericus RG-1. J Hazard Mater. 2011 Feb 28;186(2-3):1050-7. doi: 10.1016/j.jhazmat.2010.11.099. Epub 2010 Nov 30. [PubMed:21168267 ]
  5. Kobayashi K, Koyama E, Kono C, Namatame K, Nakamura K, Furukawa N: Evidence for intermolecular interaction between sulfonium and sulfide sulfur atoms and its application to synthesis of cyclic bis(disulfide) dimer. J Org Chem. 2001 Mar 23;66(6):2085-90. [PubMed:11300905 ]
  6. Ren G, Wang Z, Yu Z, Wang Y, Ma S, Wu M, Sheng G, Fu J: Primary investigation on contamination pattern of legacy and emerging halogenated organic pollutions in freshwater fish from Liaohe River, Northeast China. Environ Pollut. 2013 Jan;172:94-9. doi: 10.1016/j.envpol.2012.08.012. Epub 2012 Sep 21. [PubMed:23000968 ]
  7. de Hoog HM, Nallani M, Cornelissen JJ, Rowan AE, Nolte RJ, Arends IW: Biocatalytic oxidation by chloroperoxidase from Caldariomyces fumago in polymersome nanoreactors. Org Biomol Chem. 2009 Nov 21;7(22):4604-10. doi: 10.1039/b911370c. Epub 2009 Sep 3. [PubMed:19865695 ]
  8. Izod K, Watson JM, Clegg W, Harrington RW: Synthesis, structures and stabilities of thioanisole-functionalised phosphido-borane complexes of the alkali metals. Dalton Trans. 2011 Nov 28;40(44):11712-8. doi: 10.1039/c1dt11368b. Epub 2011 Oct 11. [PubMed:21989630 ]
  9. Lee Y, Lee DH, Park GY, Lucas HR, Narducci Sarjeant AA, Kieber-Emmons MT, Vance MA, Milligan AE, Solomon EI, Karlin KD: Sulfur donor atom effects on copper(I)/O(2) chemistry with thioanisole containing tetradentate N(3)S ligand leading to mu-1,2-peroxo-dicopper(II) species. Inorg Chem. 2010 Oct 4;49(19):8873-85. doi: 10.1021/ic101041m. [PubMed:20822156 ]
  10. Ohkawa K, Nishibayashi M, Devarayan K, Hachisu M, Araki J: Synthesis of peptide-cellulose conjugate mediated by a soluble cellulose derivative having beta-Ala esters. Int J Biol Macromol. 2013 Feb;53:150-9. doi: 10.1016/j.ijbiomac.2012.11.004. Epub 2012 Nov 21. [PubMed:23178343 ]
  11. El'kin AA, Grishko VV, Ivshina IB: [Oxidative biotransformation of thioanisole by Rhodococcus rhodochrous IEGM 66 cells]. Prikl Biokhim Mikrobiol. 2010 Nov-Dec;46(6):637-43. [PubMed:21261073 ]
  12. Prasad ChD, Balkrishna SJ, Kumar A, Bhakuni BS, Shrimali K, Biswas S, Kumar S: Transition-metal-free synthesis of unsymmetrical diaryl chalcogenides from arenes and diaryl dichalcogenides. J Org Chem. 2013 Feb 15;78(4):1434-43. doi: 10.1021/jo302480j. Epub 2013 Jan 31. [PubMed:23327334 ]
  13. Zhang JL, Garner DK, Liang L, Chen Q, Lu Y: Protein scaffold of a designed metalloenzyme enhances the chemoselectivity in sulfoxidation of thioanisole. Chem Commun (Camb). 2008 Apr 14;(14):1665-7. doi: 10.1039/b718915j. Epub 2008 Feb 4. [PubMed:18368158 ]
  14. Ryu JS, Li GY, Marks TJ: Organolathanide-catalyzed regioselective intermolecular hydroamination of alkenes, alkynes, vinylarenes, di- and trivinylarenes, and methylenecyclopropanes. Scope and mechanistic comparison to intramolecular cyclohydroaminations. J Am Chem Soc. 2003 Oct 15;125(41):12584-605. [PubMed:14531704 ]
  15. Benz L, Park A, Corey JR, Mezher MP, Park VC: Interaction of petroleum-relevant organosulfur compounds with TiO2(110). Langmuir. 2012 Jul 10;28(27):10209-16. doi: 10.1021/la301811q. Epub 2012 Jun 26. [PubMed:22694143 ]
  16. Lim JS, Kim SK: Experimental probing of conical intersection dynamics in the photodissociation of thioanisole. Nat Chem. 2010 Aug;2(8):627-32. doi: 10.1038/nchem.702. Epub 2010 Jul 4. [PubMed:20651723 ]
  17. Yamakita Y, Okazaki T, Ohno K: Conformation-specific Raman bands and electronic conjugation in substituted thioanisoles. J Phys Chem A. 2008 Nov 27;112(47):12220-7. doi: 10.1021/jp807027q. [PubMed:18980363 ]
  18. Adao P, Kuznetsov ML, Barroso S, Martins AM, Avecilla F, Costa Pessoa J: Amino alcohol-derived reduced Schiff base V(IV)O and V(V) compounds as catalysts for asymmetric sulfoxidation of thioanisole with hydrogen peroxide. Inorg Chem. 2012 Nov 5;51(21):11430-49. doi: 10.1021/ic301153p. Epub 2012 Oct 23. [PubMed:23092396 ]
  19. Munoz M, Rodriguez A, Graciani Mdel M, Moya ML: Conductometric, surface tension, and kinetic studies in mixed SDS-Tween 20 and SDS-SB3-12 micellar solutions. Langmuir. 2004 Dec 7;20(25):10858-67. [PubMed:15568834 ]
  20. Poon LC, Methot SP, Morabi-Pazooki W, Pio F, Bennet AJ, Sen D: Guanine-rich RNAs and DNAs that bind heme robustly catalyze oxygen transfer reactions. J Am Chem Soc. 2011 Feb 16;133(6):1877-84. doi: 10.1021/ja108571a. Epub 2011 Jan 25. [PubMed:21265562 ]
  21. Schroll AL, Hondal RJ, Flemer S Jr: The use of 2,2'-dithiobis(5-nitropyridine) (DTNP) for deprotection and diselenide formation in protected selenocysteine-containing peptides. J Pept Sci. 2012 Mar;18(3):155-62. doi: 10.1002/psc.1430. Epub 2012 Jan 16. [PubMed:22249911 ]
  22. Ricoux R, Allard M, Dubuc R, Dupont C, Marechal JD, Mahy JP: Selective oxidation of aromatic sulfide catalyzed by an artificial metalloenzyme: new activity of hemozymes. Org Biomol Chem. 2009 Aug 21;7(16):3208-11. doi: 10.1039/b907534h. Epub 2009 Jun 23. [PubMed:19641774 ]
  23. Zhu C, Liang J, Wang B, Zhu J, Cao Z: Significant effect of spin flip on the oxygen atom transfer reaction from (oxo)manganese(V) corroles to thioanisole: insights from density functional calculations. Phys Chem Chem Phys. 2012 Oct 5;14(37):12800-6. doi: 10.1039/c2cp41647f. [PubMed:22874974 ]
  24. Clark IP, George MW, Greetham GM, Harvey EC, Long C, Manton JC, McArdle H, Pryce MT: Photochemistry of (eta6-anisole)Cr(CO)3 and (eta6-thioanisole)Cr(CO)3: evidence for a photoinduced haptotropic shift of the thioanisole ligand, a picosecond time-resolved infrared spectroscopy and density functional theory investigation. J Phys Chem A. 2012 Jan 26;116(3):962-9. doi: 10.1021/jp211726j. Epub 2012 Jan 12. [PubMed:22204670 ]
  25. Zhou XP, Xu Z, He J, Zeller M, Hunter AD, Clerac R, Mathoniere C, Chui SS, Che CM: Coordination networks from Cu cations and tetrakis(methylthio)benzenedicarboxylic acid: tunable bonding patterns and selective sensing for NH(3) gas. Inorg Chem. 2010 Nov 1;49(21):10191-8. doi: 10.1021/ic101501p. [PubMed:20886889 ]
  26. Jaccob M, Comba P, Maurer M, Vadivelu P, Venuvanalingam P: A combined experimental and computational study on the sulfoxidation by high-valent iron bispidine complexes. Dalton Trans. 2011 Nov 14;40(42):11276-81. doi: 10.1039/c1dt11533b. Epub 2011 Sep 29. [PubMed:21959496 ]
  27. Park J, Morimoto Y, Lee YM, Nam W, Fukuzumi S: Metal ion effect on the switch of mechanism from direct oxygen transfer to metal ion-coupled electron transfer in the sulfoxidation of thioanisoles by a non-heme iron(IV)-oxo complex. J Am Chem Soc. 2011 Apr 13;133(14):5236-9. doi: 10.1021/ja200901n. Epub 2011 Mar 16. [PubMed:21410258 ]
  28. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .