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Record Information
Creation Date2009-12-17 01:41:03 UTC
Update Date2018-03-21 17:46:25 UTC
Accession NumberT3D3660
Common NameGlycolic acid
ClassSmall Molecule
DescriptionGlycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA). This colourless, odourless, and hygroscopic crystalline solid is highly soluble in water. Due to its excellent capability to penetrate skin, glycolic acid is often used in skin care products, most often as a chemical peel. It may reduce wrinkles, acne scarring, and hyperpigmentation and improve many other skin conditions, including actinic keratosis, hyperkeratosis, and seborrheic keratosis. 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. This allows the outer skin to dissolve, revealing the underlying skin. It is thought that this is due to the reduction of calcium ion concentrations in the epidermis and the removal of calcium ions from cell adhesions, leading to desquamation. Glycolic acid is a known inhibitor of tyrosinase. This can suppress melanin formation and lead to a lightening of skin colour. Acute doses of glycolic acid on skin or eyes leads to local effects that are typical of a strong acid (e.g. dermal and eye irritation). Glycolate is a nephrotoxin if consumed orally. A nephrotoxin is a compound that causes damage to the kidney and kidney tissues. Glycolic acid's renal toxicity is due to its metabolism to oxalic acid. Glycolic and oxalic acid, along with excess lactic acid, are responsible for the anion gap metabolic acidosis. Oxalic acid readily precipitates with calcium to form insoluble calcium oxalate crystals. Renal tissue injury is caused by widespread deposition of oxalate crystals and the toxic effects of glycolic acid. Glycolic acid does exhibit some inhalation toxicity and can cause respiratory, thymus, and liver damage if present in very high levels over long periods of time.
Compound Type
  • Cosmetic Toxin
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Keratolytic Agent
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
2-Hydroxyacetic acid
a-Hydroxyacetic acid
alpha-Hydroxyacetic acid
Glycollic acid
GlyPure 70
Hydroxyacetic acid
Hydroxyethanoic acid
Sodium glycolate
Chemical FormulaC2H4O3
Average Molecular Mass76.051 g/mol
Monoisotopic Mass76.016 g/mol
CAS Registry Number79-14-1
IUPAC Name2-hydroxyacetic acid
Traditional Nameglycolic acid
InChI IdentifierInChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
Chemical Taxonomy
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
  • 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
Biological Properties
StatusDetected and Not Quantified
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Peroxisome
Biofluid LocationsNot Available
Tissue Locations
  • Bladder
  • Fibroblasts
  • Liver
  • Skin
  • Stratum Corneum
Primary Hyperoxaluria Type ISMP00352 Not Available
Biological Roles
Chemical RolesNot Available
Physical Properties
AppearanceWhite powder.
Experimental Properties
Melting Point75-80°C
Boiling PointNot Available
Solubility1000 mg/mL at 25°C
Predicted Properties
Water Solubility608 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-ed8b8e4a9e2556ea02e2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-003r-2910000000-bd50bf5bab6f5327eaf4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-cadf899be6b15d008330JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-e66ed28d8419895e0fb4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0900000000-7f84fac3284d17fa3ba6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-ed8b8e4a9e2556ea02e2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003r-2910000000-bd50bf5bab6f5327eaf4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-d724c85a3b30e3c2e4bcJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a7l-9000000000-1e9466549305eb20257bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05i9-9520000000-5f0019fe63eb6e692109JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-9000000000-e942bdae1d60e5f5d649JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9000000000-f225de2de3540c3f50a4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-7de217d97b44f53aad82JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-88af2b259f82cd1d8938JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-c968a24f0640b154325bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0059-9000000000-1dfacf30bf94ce3bf8bbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-88af2b259f82cd1d8938JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-c968a24f0640b154325bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0059-9000000000-1dfacf30bf94ce3bf8bbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-004i-9000000000-fa715ee3ce9abbc94edbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 2V, positivesplash10-004i-9000000000-ace3c5f526d28fd24de9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 3V, positivesplash10-004i-9000000000-ff7f922c2460adb6a10dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-004i-9000000000-1d63aaaf9cbc6d3bb3b4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-004j-9000000000-e9c74e7df728e016450cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-002b-9000000000-d0963403f3a8ff9e576dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-002b-9000000000-9e1d6b2e2b889232d610JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0002-9000000000-e9824f68b2176db90d33JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-000t-9000000000-02329982bc7150d972bfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-000t-9000000000-216d8ece56b0a44e5289JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-d961c3c14ec415e3141eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-67f73be970ba9f885c4aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-7445713a5fe347bbc8b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-26e13242443efc1aa846JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-6ba976b949118cd0a86aJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-2885890e3bb8c015742fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureOral (30) ; dermal (30)
Mechanism of ToxicityGlycolic acid's toxicity is due to its metabolism to oxalic acid. Glycolic and oxalic acid, along with excess lactic acid, are responsible for the anion gap metabolic acidosis. Oxalic acid readily precipitates with calcium to form insoluble calcium oxalate crystals. Tissue injury is caused by widespread deposition of oxalate crystals and the toxic effects of glycolic acid. (1, 2)
MetabolismThe main path of the degradation of glycolic acid is to glyoxylic acid. This reaction is mediated by lactic dehydrogenase or glycolic acid oxidase. Once glyoxylic acid is formed, it is apparently degraded very rapidly to a variety of products, a few of which have been observed. Its breakdown to 2-hydroxy-3-oxoadipate it is thought, is mediated by thiamine pyrophosphate in the presence of magnesium ions. The formation of glycine involves pyridoxal phosphate and glyoxylate transaminase, whereas the formation of carbon dioxide and water via formic acid apparently involves coenzyme A (CoA) and flavin mononucleotides. (25)
Toxicity ValuesLD50: 1950 mg/kg (Oral, Rat) (3) LD50: 1000 mg/kg (Intravenous, Cat) (4) LC50: 7.7-14 mg/L over 4 hours (Inhalation, Rat) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesDue to its excellent capability to penetrate skin, glycolic acid finds applications in skin care products, most often as a chemical peel. It may reduce wrinkles, acne scarring, hyperpigmentation and improve many other skin conditions, including actinic keratosis, hyperkeratosis, and seborrheic keratosis. Glycolic acid is also a useful intermediate for organic synthesis and finds employment in the textile industry as a dyeing and tanning agent, in food processing as a flavoring agent and as a preservative. Glycolic acid is often included into emulsion polymers, solvents and additives for ink and paint in order to improve flow properties and impart gloss. (30)
Minimum Risk LevelNot Available
Health EffectsGlycolic acid metabolizes to oxalic acid, which reacts with calcium and forms calcium oxalate crystals in the kidney. This can cause kidney injury, leading to acute kidney failure. (31) Chronically high levels of glycolic acid are associated with the inborn error of metabolism known as Type I primary hyperoxaluria. Oxalate stones in primary hyperoxaluria tend to be severe, resulting in relatively early kidney damage (before age 20), which impairs the excretion of oxalate leading to a further acceleration in accumulation of oxalate in the body. After the development of renal failure patients may develop oxalate deposits in the bones, joints and bone marrow. Severe cases may develop haematological problems such as anaemia and thrombocytopaenia. The deposition of oxalate in the body is sometimes called "oxalosis" to be distinguished from "oxaluria" which refers to oxalate in the urine.
SymptomsGlycolic acid is a strong irritant. Accumulation of glycolic acid and its metabolite, oxalic acid, causes tachycardia, hypertension, hyperventilation, and metabolic acidosis. (31, 30)
TreatmentChronic Exposure: In some patients with primary hyperoxaluria type 1, pyridoxine treatment (vitamin B6) may decrease oxalate excretion and prevent kidney stone formation. Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB03085
PubChem Compound ID757
ChemSpider ID737
UniProt IDNot Available
OMIM ID259900 , 260000
ChEBI ID29805
CTD IDNot Available
Stitch IDNot Available
ACToR IDNot Available
Wikipedia LinkGlycolic_acid
Synthesis Reference

David Y. Tang, Arthur M. Foster, “(3-Trifluoromethylphenyl)-alpha-hydroxyacetic acid and process for preparation.” U.S. Patent US4296244, issued January, 1977.

General References
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Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available


General Function:
Protein homodimerization activity
Specific Function:
Catalyzes the rate-limiting step of the oxidative pentose-phosphate pathway, which represents a route for the dissimilation of carbohydrates besides glycolysis. The main function of this enzyme is to provide reducing power (NADPH) and pentose phosphates for fatty acid and nucleic acid synthesis.
Gene Name:
Uniprot ID:
Molecular Weight:
59256.31 Da
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