Record Information
Version1.0
Creation date2010-04-08 22:05:44 UTC
Update date2018-05-29 00:38:00 UTC
Primary IDFDB003298
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHydroxyacetic acid
DescriptionFound in sugar cane (Saccharum officinarum) Glycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA). This colorless, odorless, and hygroscopic crystalline solid is highly soluble in water. It is used in various skin-care products. Glycolic acid is found in some sugar-crops.
CAS Number79-14-1
Structure
Thumb
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)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
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-cadf899be6b15d008330View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-e66ed28d8419895e0fb4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0900000000-7f84fac3284d17fa3ba6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-ed8b8e4a9e2556ea02e2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003r-2910000000-bd50bf5bab6f5327eaf4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-d724c85a3b30e3c2e4bcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a7l-9000000000-1e9466549305eb20257bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05i9-9520000000-5f0019fe63eb6e692109View in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-88af2b259f82cd1d8938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-c968a24f0640b154325bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , 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 AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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.