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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:48 UTC
Update Date2019-07-23 06:08:56 UTC
HMDB IDHMDB0031520
Secondary Accession Numbers
  • HMDB31520
Metabolite Identification
Common Name2-Mercaptopropanoic acid
Description2-Mercaptopropanoic acid, also known as 2-thiolactic acid or 2-thiolactate, belongs to the class of organic compounds known as alpha-mercaptocarboxylic acids. These are carboxylic acids that bear a thiol group at the C-2 position. Alpha-mercaptocarboxylic acids have the general formula RC(S)C(=O)O, where R = H, organyl group. Thiolactic acid is the organosulfur compound with the formula HSCH2CO2H. 2-Mercaptopropanoic acid is a weakly acidic compound (based on its pKa). Instead of using the acid itself, its salts are used. 2-Mercaptopropanoic acid is a meaty, roasted, and sulfurous tasting compound. Outside of the human body,. The molecule contains both carboxylic acid and thiol functional groups. It is structurally related to lactic acid by the interchange of SH for OH. It is a colorless oil. It is now mainly used for depilation. Thiolactic acid was once widely used in hair permanent waving formulations, but has been displaced by formulations based on thioglycolic acid.
Structure
Data?1563862136
Synonyms
ValueSource
2-Mercaptopropionic acidChEBI
2-Thiolactic acidChEBI
2-Thiolpropionic acidChEBI
alpha-Mercaptopropanoic acidChEBI
alpha-Mercaptopropionic acidChEBI
Thiolactic acidChEBI
2-MercaptopropionateGenerator
2-ThiolactateGenerator
2-ThiolpropionateGenerator
a-MercaptopropanoateGenerator
a-Mercaptopropanoic acidGenerator
alpha-MercaptopropanoateGenerator
Α-mercaptopropanoateGenerator
Α-mercaptopropanoic acidGenerator
a-MercaptopropionateGenerator
a-Mercaptopropionic acidGenerator
alpha-MercaptopropionateGenerator
Α-mercaptopropionateGenerator
Α-mercaptopropionic acidGenerator
ThiolactateGenerator
2-MercaptopropanoateGenerator
2-Mercapto-propanoic acidHMDB
2-Mercapto-propionic acidHMDB
2-Sulfanylpropanoic acidHMDB
alpha -Mercaptopropanoic acidHMDB
alpha -Mercaptopropionic acidHMDB
FEMA 3180HMDB
Ammonium thiolactateMeSH
Thiolactic acid, (S)-isomerMeSH
Thiolactic acid, disilver salt (+1)MeSH
Thiolactic acid, monoammonium saltMeSH
Thiolactic acid, calcium salt (2:1)MeSH
Thiolactic acid, strontium salt (2:1)MeSH
Thiolactic acid, (R)-isomerMeSH
Thiolactic acid, monolithium saltMeSH
Chemical FormulaC3H6O2S
Average Molecular Weight106.144
Monoisotopic Molecular Weight106.008850126
IUPAC Name2-sulfanylpropanoic acid
Traditional Namethiolactic acid
CAS Registry Number79-42-5
SMILES
CC(S)C(O)=O
InChI Identifier
InChI=1S/C3H6O2S/c1-2(6)3(4)5/h2,6H,1H3,(H,4,5)
InChI KeyPMNLUUOXGOOLSP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-mercaptocarboxylic acids. These are carboxylic acids that bear a thiol group at the C-2 position. Alpha-mercaptocarboxylic acids have the general formula RC(S)C(=O)O, where R = H, organyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct Parentalpha-Mercaptocarboxylic acids
Alternative Parents
Substituents
  • 2-mercaptocarboxylic acid
  • Monocarboxylic acid or derivatives
  • Alkylthiol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point12 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.5 g/LALOGPS
logP0.62ALOGPS
logP0.57ChemAxon
logS-0.81ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity24.97 m³·mol⁻¹ChemAxon
Polarizability10.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08ou-9100000000-1ddf1e7864794c2a9d67Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-024r-9300000000-c8b327dd622ce8610af7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-8e01a7bcebf854db93b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g0-9100000000-6a8bb0d8374bd2086a27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-32e7619d6cd6cc5ac61eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-6900000000-82a7fd269418d8e68299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9300000000-05b84a2072b802d6d685Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fer-9000000000-54b8055a55c3e7f9c304Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB008120
KNApSAcK IDNot Available
Chemspider ID56121
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThiolactic acid
METLIN IDNot Available
PubChem Compound62326
PDB IDNot Available
ChEBI ID47872
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .