p-Toluenesulfonic acid (CED0004425)

Record Information
Version1.0
Creation Date2016-05-19 02:58:07 UTC
Update Date2026-05-14 17:48:09 UTC
Accession NumberCHEM009098
Identification
Common Namep-Toluenesulfonic acid
ClassSmall Molecule
Description
p-Toluenesulfonic acid (C7H8O3S) is a chemical compound with an average molecular weight of 172.20 g/mol. p-Toluenesulfonic acid belongs to the benzenesulfonic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. In industrial applications, it is used as a surfactant (surface active agent), a solubility enhancer, a catalyst (PMC10490356), an acid (PMC10490356), and an activator (PMC10507666). This compound is found in or released from 26 recorded sources. These include drinking water and water supply (drinking water), building and construction materials (ceilings, ladders), and food, food processing and cookware (food preservation, processing meats, food contact materials, and fermentation processes for beer). It is also present in household cleaning and consumer products, such as soap detergents, bleaching agents, perfumes within detergents and soaps, tobacco smoke filters, and cigar cigarettes. Additionally, it is associated with electrical and electronic equipment, including antennas, amplifiers, communication cables or conductors, electric switches, and conductors or conductive bodies characterised by the conductive materials, among 9 others. Recorded exposure routes for the compound include oral, inhalation, and touch. Regarding its biological activity, there are 2 recorded protein targets: pro-cathepsin H (CTSH) and lysozyme C (LYZ).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
4-Cresol sulfateChEBI
Sulfuric acid mono-p-tolyl esterChEBI
4-Cresol sulfuric acidGenerator
4-Cresol sulphateGenerator
4-Cresol sulphuric acidGenerator
Sulfate mono-p-tolyl esterGenerator
Sulphate mono-p-tolyl esterGenerator
Sulphuric acid mono-p-tolyl esterGenerator
p-Cresol sulfuric acidGenerator
p-Cresol sulphateGenerator
p-Cresol sulphuric acidGenerator
mono(4-Methylphenyl) sulfateHMDB
p-Cresyl sulfateHMDB
p-Cresyl sulphateHMDB
p-Cresyl-sulfateHMDB
p-Cresyl-sulphateHMDB
p-CresylsulfateHMDB
p-CresylsulphateHMDB
p-Tolyl sulfate (6ci,7ci)HMDB
p-Tolyl sulphate (6ci,7ci)HMDB
Para-cresol sulfateHMDB
Para-cresol sulphateHMDB
Sulfuric acid mono(p-tolyl) ester (8ci)HMDB
Sulfuric acid, mono(4-methylphenyl) esterHMDB
Chemical FormulaC7H8O3S
Average Molecular Mass172.202 g/mol
Monoisotopic Mass172.019 g/mol
CAS Registry Number104-15-4
IUPAC Name(4-methylphenyl)oxidanesulfonic acid
Traditional Name(4-methylphenyl)oxidanesulfonic acid
SMILESCC1=CC=C(C=C1)S(O)(=O)=O
InChI IdentifierInChI=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 phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassArylsulfates
Direct ParentPhenylsulfates
Alternative Parents
Substituents
  • Phenylsulfate
  • Phenoxy compound
  • Toluene
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP-0.55ALOGPS
logP1.71ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.07 m³·mol⁻¹ChemAxon
Polarizability17.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-004m-7970000000-1d52a5deeb555385dd84Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-004m-7970000000-1d52a5deeb555385dd84Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9300000000-938ee4a29fd12e145c3eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-0fa26790bdae62d2f937Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05di-7900000000-d4586ea5109738cd28deNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-3efcc1fdafaf68596c13Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9200000000-e6d02384d163b8652ef6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9400000000-3acc4cb96eb90c46eab7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9300000000-4786552fedf27d52f5ffNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-8e801c5f02b8b91ac0c8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-d4f2ab7d5f049cf00bceNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-9df35bcc2b4f4ad07c7dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05di-6900000000-114fba49849a17a55579Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-e6e656b40417d4e53cbcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-403b11ba3a676ce16d8eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-d0b1914485d9ea6a8ed1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1900000000-74933fb0a0cfaed5004fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fvi-9100000000-e58b15b2e4247f942ffdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-297c45510f8bcc2c7332Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1900000000-10b19a616e398d436d3dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-a5047b754e5ca626159bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-9800000000-6a6e47b392412e3380cfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-47d2029de8830d06652eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-678d1f8502351120ed4eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-fccc99d7e49724825430Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-f7c1cb2b8c24df5cd33eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-4900000000-2ad36f938d38a4332b30Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2481.0Log mg/kg[1400:4400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
490Personal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
622Game AccessoriesRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
639Degreasing LeatherTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
641Foam DyeingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)27.6365
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)28.1036
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)54.3388
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)28.7264
Click to view 3D structureBeta-ketoacyl-ACP-synthase IIIO77078Plasmodium falciparumPredicted (SEA)0.389246
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)81.8195
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)14.9471
Click to view 3D structureCarbonic anhydrase 2P00921Bos taurusPredicted (SEA)9.34191
Click to view 3D structureDelta carbonic anhydraseQ5U9J1Conticribra weissflogiiPredicted (SEA)10.1982
Click to view 3D structureCarbonate dehydrataseB2V8E3Sulfurihydrogenibium sp. (strain YO3AOP1)Predicted (SEA)14.2464
Click to view 3D structureAstrosclerin-3A6YCJ1Astrosclera willeyanaPredicted (SEA)15.6477
Click to view 3D structureCarbonic anhydraseQ6FTL6Candida glabrata CBS 138Predicted (SEA)22.4984
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)13.7015
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)17.4382
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)33.9423
Click to view 3D structureCarbonic anhydrase, alpha familyQ31FD6Thiomicrospira crunogenaPredicted (SEA)14.2464
Click to view 3D structureCarbonic anhydraseC0IX24Stylophora pistillataPredicted (SEA)13.7015
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)23.4326
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)41.2601
Click to view 3D structureCarbonic anhydraseO24855Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)Predicted (SEA)16.2705
Click to view 3D structureBeta-carbonic anhydrase 1P9WPJ7Mycobacterium tuberculosisPredicted (SEA)22.8098
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)48.5001
Click to view 3D structureGlucose-6-phosphate dehydrogenase-6-phosphogluconolactonaseQ9BHT9Plasmodium bergheiPredicted (SEA)6.77288
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)60.2553
Carbonic anhydrase 3 structureClick to view 3D structureCarbonic anhydrase 3P07451HumansPredicted (SEA)23.9776
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0011635
FooDB IDFDB028333
Phenol Explorer IDNot Available
KNApSAcK IDC00052378
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID3806481
ChEBI ID82914
PubChem Compound ID4615423
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10775436
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18941347
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21751871
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24231664
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25147155
6. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
7. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8
8. Cao L, Kirk MC, Coward LU, Jackson P, Whitaker JN: p-Cresol sulfate is the dominant component of urinary myelin basic protein like material. Arch Biochem Biophys. 2000 May 1;377(1):9-21.
9. Raff AC, Meyer TW, Hostetter TH: New insights into uremic toxicity. Curr Opin Nephrol Hypertens. 2008 Nov;17(6):560-5. doi: 10.1097/MNH.0b013e32830f45b6.
10. Sivsammye G, Sims HV: Presumptive identification of Clostridium difficile by detection of p-cresol in prepared peptone yeast glucose broth supplemented with p-hydroxyphenylacetic acid. J Clin Microbiol. 1990 Aug;28(8):1851-3.
11. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24.
12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.