You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-13 07:01:17 UTC
Update Date2019-01-11 19:17:47 UTC
HMDB IDHMDB0003903
Secondary Accession Numbers
  • HMDB03903
Metabolite Identification
Common Name2-Hydroxyethanesulfonate
Description2-Hydroxyethanesulfonate (also known as 2-Hydroxyethanesulfonic acid or isethionic acid) is an organosulfur compound containing a short chain alkane sulfonate linked to a hydroxyl group. It is a water-soluble liquid used in the manufacture of mild, biodegradable, and high-foaming anionic surfactants. These surfactants provide gentle cleansing and a soft skin feel. 2-Hydroxyethanesulfonate forms a colourless, syrupy, and strongly acidic liquid that can form detergents with oleic acid. 2-Hydroxyethanesulfonate is frequently used in the industrial production of taurine. Mammals are also able to endogenously synthesize 2-hydroxyethanesulfonate via taurine through a possible enzymatic deamination process (PMID: 14490797 ). 2-Hydroxyethanesulfonate can be found in both human plasma and urine (PMID: 1159536 , PMID: 6066118 ). Higher plasma levels of 2-hydroxyethanesulfonate have been shown to be protective against type 2 diabetes.
Structure
Data?1547234267
Synonyms
ValueSource
2-Hydroxyethane-1-sulfonic acidChEBI
2-Hydroxyethanesulfonic acidChEBI
2-Hydroxyethylsulfonic acidChEBI
beta-Hydroxyethanesulfonic acidChEBI
Isethionic acidKegg
IsethionateKegg
2-Hydroxyethane-1-sulfonateGenerator
2-Hydroxyethane-1-sulphonateGenerator
2-Hydroxyethane-1-sulphonic acidGenerator
2-HydroxyethanesulphonateGenerator
2-Hydroxyethanesulphonic acidGenerator
2-HydroxyethylsulfonateGenerator
2-HydroxyethylsulphonateGenerator
2-Hydroxyethylsulphonic acidGenerator
b-HydroxyethanesulfonateGenerator
b-Hydroxyethanesulfonic acidGenerator
b-HydroxyethanesulphonateGenerator
b-Hydroxyethanesulphonic acidGenerator
beta-HydroxyethanesulfonateGenerator
beta-HydroxyethanesulphonateGenerator
beta-Hydroxyethanesulphonic acidGenerator
Β-hydroxyethanesulfonateGenerator
Β-hydroxyethanesulfonic acidGenerator
Β-hydroxyethanesulphonateGenerator
Β-hydroxyethanesulphonic acidGenerator
(2-Hydroxyethyl)sulfonateHMDB
(2-Hydroxyethyl)sulfonic acidHMDB
EthanolsulfonateHMDB
Ethanolsulfonic acidHMDB
HydroxyethylsulfonateHMDB
Hydroxyethylsulfonic acidHMDB
Isethionic acid sodium saltHMDB
Kyselina isethionovaHMDB
Potassium 2-hydroxyethanesulfonateHMDB
Potassium isethionateHMDB
Sodium 2-hydroxyethanesulfonateHMDB
Sodium 2-hydroxyethyl sulfonateHMDB
Sodium beta-hydroxyethanesulfonateHMDB
Sodium isethionateHMDB
Isethionate, sodiumHMDB
Acid, isethionicHMDB
Isethionic acid monopotassium saltHMDB
Isethionic acid monosodium saltHMDB
Acid, hydroxyethylsulfonicHMDB
Isethionic acid monoammonium saltHMDB
2-HydroxyethanesulfonateGenerator
Chemical FormulaC2H6O4S
Average Molecular Weight126.132
Monoisotopic Molecular Weight125.99867937
IUPAC Name2-hydroxyethane-1-sulfonic acid
Traditional Namesodium isethionate
CAS Registry Number107-36-8
SMILES
OCCS(O)(=O)=O
InChI Identifier
InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)
InChI KeySUMDYPCJJOFFON-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
Substituents
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility103 g/LALOGPS
logP-2.2ALOGPS
logP-2.9ChemAxon
logS-0.09ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.95 m³·mol⁻¹ChemAxon
Polarizability10.43 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000y-9100000000-91c2f22c70185fb5bafeJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9300000000-7f0eccc0156cbd7e5b23JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-b8df238a554a2725a4d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-6900000000-c72536efb4cfd09b2759JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-61473ee5b4612e7ca273JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-d85e73096201062faad2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-ce44d57a4275daa8f563JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0900000000-f83dca3bb4164fb39fc2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054k-8900000000-111dba10014f3cc5c403JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9300000000-5cc44eb483ce09d49510JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-6900000000-c1573e4b7aa0acf67018JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-9600000000-894c171421adedc823bbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-b8c542a1a77eb7a6a191JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023245
KNApSAcK IDNot Available
Chemspider ID7578
KEGG Compound IDC05123
BioCyc IDCPD-3745
BiGG IDNot Available
Wikipedia LinkIsethionic_acid
METLIN ID6987
PubChem Compound7866
PDB IDNot Available
ChEBI ID1157
References
Synthesis ReferenceChen, Zhiwen; Liao, Xiangxu; Qian, Weiqiang; et al. Process for preparation of hydroxyalkanesulfonic acids for plating solutions. Faming Zhuanli Shenqing Gongkai Shuomingshu (1990), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kersten A, Althaus C, Seitz HM, Pfahl HG, Sundmacher R: [Bilateral microsporidial keratitis in an HIV-positive patient with AIDS stage infection]. Klin Monbl Augenheilkd. 1998 Jun;212(6):476-9. [PubMed:9715470 ]
  2. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
  3. READ WO, WELTY JD: Synthesis of taurine and isethionic acid by dog heart slices. J Biol Chem. 1962 May;237:1521-2. [PubMed:14490797 ]
  4. Sturman JA, Hepner GW, Hofmann AF, Thomas PJ: Metabolism of [35S]taurine in man. J Nutr. 1975 Sep;105(9):1206-14. [PubMed:1159536 ]
  5. Jacobsen JG, Collins LL, Smith LH Jr: Urinary excretion of isethionic acid in man. Nature. 1967 Jun 17;214(5094):1247-8. [PubMed:6066118 ]