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Showing Compound Hydroxyacetic acid (FDB003298)

Record Information
Version1.0
Creation date2010-04-08 22:05:44 UTC
Update date2020-09-17 15:38:20 UTC
Primary IDFDB003298
Secondary Accession Numbers
  • FDB030894
Chemical Information
FooDB NameHydroxyacetic acid
DescriptionGlycolic acid, also known as 2-hydroxyacetate or glycolate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. Glycolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycolic acid exists in all living species, ranging from bacteria to humans. In humans, glycolic acid is involved in rosiglitazone metabolism pathway. Outside of the human body, Glycolic acid has been detected, but not quantified in, several different foods, such as sourdocks, pineappple sages, celeriacs, cloves, and feijoa. This could make glycolic acid a potential biomarker for the consumption of these foods. Once applied, glycolic acid reacts with the upper layer of the epidermis, weakening the binding properties of the lipids that hold the dead skin cells together. Glycolic acid is a potentially toxic compound. Glycolic acid, with regard to humans, has been found to be associated with several diseases such as transurethral resection of the prostate and biliary atresia; glycolic acid has also been linked to several inborn metabolic disorders including glutaric acidemia type 2, glycolic aciduria, and d-2-hydroxyglutaric aciduria. Glycolic and oxalic acid, along with excess lactic acid, are responsible for the anion gap metabolic acidosis.
CAS Number79-14-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-Hydroxyacetic acidChEBI
2-Hydroxyethanoic acidChEBI
alpha-Hydroxyacetic acidChEBI
Glycollic acidChEBI
HOCH2COOHChEBI
Hydroxyacetic acidChEBI
Hydroxyethanoic acidChEBI
2-HydroxyacetateGenerator
2-HydroxyethanoateGenerator
a-HydroxyacetateGenerator
a-Hydroxyacetic acidGenerator
alpha-HydroxyacetateGenerator
Α-hydroxyacetateGenerator
Α-hydroxyacetic acidGenerator
GlycollateGenerator
HydroxyacetateGenerator
HydroxyethanoateGenerator
GlycolateGenerator
GlycocideHMDB
GlyPureHMDB
GlyPure 70HMDB
Sodium glycolateHMDB
Glycolic acid, 2-(14)C-labeledHMDB
Glycolic acid, 1-(14)C-labeledHMDB
Glycolic acid, potassium saltHMDB
Glycolic acid, monopotassium saltHMDB
Glycolic acid, calcium saltHMDB
Glycolic acid, monoammonium saltHMDB
Glycolic acid, monolithium saltHMDB
Glycolic acid, monosodium saltHMDB
Potassium glycolateHMDB
α-hydroxyacetic acidbiospider
2-Hydroxy carboxylatebiospider
2-Hydroxy carboxylic acidbiospider
Acetic acid, 2-hydroxy-biospider
Acetic acid, hydroxy- (9CI)biospider
Glycolic aciddb_source
α-hydroxyacetateGenerator
α-hydroxyacetic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility608 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.35 m³·mol⁻¹ChemAxon
Polarizability6.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC2H4O3
IUPAC name2-hydroxyacetic acid
InChI IdentifierInChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
InChI KeyAEMRFAOFKBGASW-UHFFFAOYSA-N
Isomeric SMILESOCC(O)=O
Average Molecular Weight76.0514
Monoisotopic Molecular Weight76.016043994
Classification
Description Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 31.59%; H 5.30%; O 63.11%DFC
Melting PointMp 80°DFC
Boiling PointBp 100° dec.DFC
Experimental Water SolubilityNot Available
Experimental logP-1.11HANSCH,C ET AL. (1995)
Experimental pKapKa 3.82DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-2885890e3bb8c015742fSpectrum
GC-MSHydroxyacetic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-ed8b8e4a9e2556ea02e2Spectrum
GC-MSHydroxyacetic acid, 2 TMS, GC-MS Spectrumsplash10-00dj-9600000000-8bafc88c7bf4e90fb5e8Spectrum
GC-MSHydroxyacetic acid, 2 TMS, GC-MS Spectrumsplash10-003r-2910000000-bd50bf5bab6f5327eaf4Spectrum
GC-MSHydroxyacetic acid, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-cadf899be6b15d008330Spectrum
GC-MSHydroxyacetic acid, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-e66ed28d8419895e0fb4Spectrum
GC-MSHydroxyacetic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-7f84fac3284d17fa3ba6Spectrum
GC-MSHydroxyacetic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-ed8b8e4a9e2556ea02e2Spectrum
GC-MSHydroxyacetic acid, non-derivatized, GC-MS Spectrumsplash10-00dj-9600000000-8bafc88c7bf4e90fb5e8Spectrum
GC-MSHydroxyacetic acid, non-derivatized, GC-MS Spectrumsplash10-003r-2910000000-bd50bf5bab6f5327eaf4Spectrum
GC-MSHydroxyacetic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-d724c85a3b30e3c2e4bcSpectrum
Predicted GC-MSHydroxyacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a7l-9000000000-1e9466549305eb20257bSpectrum
Predicted GC-MSHydroxyacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i9-9520000000-5f0019fe63eb6e692109Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-9000000000-e942bdae1d60e5f5d649Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9000000000-f225de2de3540c3f50a4Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-7de217d97b44f53aad82Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-88af2b259f82cd1d8938Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-c968a24f0640b154325bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0059-9000000000-1dfacf30bf94ce3bf8bbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-88af2b259f82cd1d8938Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-c968a24f0640b154325bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0059-9000000000-1dfacf30bf94ce3bf8bbSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-004i-9000000000-fa715ee3ce9abbc94edbSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 2V, positivesplash10-004i-9000000000-ace3c5f526d28fd24de9Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 3V, positivesplash10-004i-9000000000-ff7f922c2460adb6a10dSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-004i-9000000000-1d63aaaf9cbc6d3bb3b4Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-004j-9000000000-e9c74e7df728e016450cSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-002b-9000000000-d0963403f3a8ff9e576dSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-002b-9000000000-9e1d6b2e2b889232d610Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0002-9000000000-e9824f68b2176db90d33Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-000t-9000000000-02329982bc7150d972bfSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-000t-9000000000-216d8ece56b0a44e5289Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-d961c3c14ec415e3141eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-67f73be970ba9f885c4aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-7445713a5fe347bbc8b8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-26e13242443efc1aa846Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-6ba976b949118cd0a86aSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID737
ChEMBL IDCHEMBL252557
KEGG Compound IDC03547
Pubchem Compound ID757
Pubchem Substance IDNot Available
ChEBI ID17497
Phenol-Explorer IDNot Available
DrugBank IDDB03085
HMDB IDHMDB00115
CRC / DFC (Dictionary of Food Compounds) IDCVS61-P:CVS61-P
EAFUS IDNot Available
Dr. Duke IDGLYCOLLIC-ACID|GLYCOLIC-ACID
BIGG ID34090
KNApSAcK IDC00007461
HET IDGOA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGlycolic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cholesterolyticDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hepatotonicDUKE
irritantDUKE
Enzymes
NameGene NameUniProt ID
Glucose-6-phosphate 1-dehydrogenaseG6PDP11413
Phosphoglycolate phosphatasePGPA6NDG6
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.