Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110053
Identification
Name: glycolate
Description:A hydroxy monocarboxylic acid anion that is acetate where the methyl group has been hydroxylated.
Structure
Thumb
Synonyms:
  • hydroxyacetic acid
  • glycolic acid
  • glycollate
Chemical Formula: C2H3O3
Average Molecular Weight: 75.044
Monoisotopic Molecular Weight: 76.0160439947
InChI Key: AEMRFAOFKBGASW-UHFFFAOYSA-M
InChI: InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)/p-1
CAS number: 79-14-1
IUPAC Name:hydroxyacetate
Traditional IUPAC Name: glycolic acid
SMILES:C(C(=O)[O-])O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassHydroxy acids and derivatives
Direct Parent Alpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 75 - 80 °C
Experimental Properties:
PropertyValueReference
Melting Point75 - 80 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.11HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility608.0 mg/mLALOGPS
logP-1ALOGPS
logP-1ChemAxon
logS0.9ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.35 m3·mol-1ChemAxon
Polarizability6.2 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0900000000-ed8b8e4a9e2556ea02e2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-003r-2910000000-bd50bf5bab6f5327eaf4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-9000000000-e942bdae1d60e5f5d649View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9000000000-f225de2de3540c3f50a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-7de217d97b44f53aad82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-88af2b259f82cd1d8938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-c968a24f0640b154325bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0059-9000000000-1dfacf30bf94ce3bf8bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-d961c3c14ec415e3141eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-67f73be970ba9f885c4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-7445713a5fe347bbc8b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-26e13242443efc1aa846View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-6ba976b949118cd0a86aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-2885890e3bb8c015742fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human. Physiological genomics 29, Pubmed: 17190852
  • Grostern A, Sales CM, Zhuang WQ, Erbilgin O, Alvarez-Cohen L (2012)Glyoxylate metabolism is a key feature of the metabolic degradation of 1,4-dioxane by Pseudonocardia dioxanivorans strain CB1190. Applied and environmental microbiology 78, Pubmed: 22327578
  • Niessen M, Krause K, Horst I, Staebler N, Klaus S, Gaertner S, Kebeish R, Araujo WL, Fernie AR, Peterhansel C (2012)Two alanine aminotranferases link mitochondrial glycolate oxidation to the major photorespiratory pathway in Arabidopsis and rice. Journal of experimental botany 63, Pubmed: 22268146
  • Schmitt DC, Malow EJ, Johnson JS (2012)Three-component glycolate Michael reactions of enolates, silyl glyoxylates, and a,ß-enones. The Journal of organic chemistry 77, Pubmed: 22394389
  • Jiang J, Johnson LC, Knight J, Callahan MF, Riedel TJ, Holmes RP, Lowther WT (2012)Metabolism of [13C5]hydroxyproline in vitro and in vivo: implications for primary hyperoxaluria. American journal of physiology. Gastrointestinal and liver physiology 302, Pubmed: 22207577
  • Knight J, Hinsdale M, Holmes R (2012)Glycolate and 2-phosphoglycolate content of tissues measured by ion chromatography coupled to mass spectrometry. Analytical biochemistry 421, Pubmed: 22093610
  • Salido E, Pey AL, Rodriguez R, Lorenzo V (2012)Primary hyperoxalurias: disorders of glyoxylate detoxification. Biochimica et biophysica acta 1822, Pubmed: 22446032
Synthesis Reference: Witzemann, Edgar J. Preparation of glycollic acid. Journal of the American Chemical Society (1917), 39 109-12.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS79-14-1
ChEBI29805
ChemSpider4573887
DrugBankDB03085
HMDBHMDB00115
IAF126034090
KEGGC00160
MetaboLightsMTBLC29805
PubChem5460308