ContaminantDB: Glycolic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-12-17 01:41:03 UTC

Update Date

2026-04-17 19:11:56 UTC

Accession Number

CHEM002629

Identification

Common Name

Glycolic acid

Class

Small Molecule

Description

Glycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA). This colorless, odorless, and hygroscopic crystalline solid is highly soluble in water. Due 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. 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. (26)

Contaminant Sources

Cosmetic Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Cosmetic Toxin
Food Toxin
Household Toxin
Industrial/Workplace Toxin
Keratolytic Agent
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxyacetic acid	ChEBI
2-Hydroxyethanoic acid	ChEBI
alpha-Hydroxyacetic acid	ChEBI
Glycollic acid	ChEBI
HOCH2COOH	ChEBI
Hydroxyacetic acid	ChEBI
Hydroxyethanoic acid	ChEBI
2-Hydroxyacetate	Generator
2-Hydroxyethanoate	Generator
a-Hydroxyacetate	Generator
a-Hydroxyacetic acid	Generator
alpha-Hydroxyacetate	Generator
Α-hydroxyacetate	Generator
Α-hydroxyacetic acid	Generator
Glycollate	Generator
Hydroxyacetate	Generator
Hydroxyethanoate	Generator
Glycolate	Generator
Glycocide	HMDB
GlyPure	HMDB
GlyPure 70	HMDB
Sodium glycolate	HMDB
Glycolic acid, 2-(14)C-labeled	HMDB
Glycolic acid, 1-(14)C-labeled	HMDB
Glycolic acid, potassium salt	HMDB
Glycolic acid, monopotassium salt	HMDB
Glycolic acid, calcium salt	HMDB
Glycolic acid, monoammonium salt	HMDB
Glycolic acid, monolithium salt	HMDB
Glycolic acid, monosodium salt	HMDB
Potassium glycolate	HMDB

Chemical Formula

C₂H₄O₃

Average Molecular Mass

76.051 g/mol

Monoisotopic Mass

76.016 g/mol

CAS Registry Number

79-14-1

IUPAC Name

2-hydroxyacetic acid

Traditional Name

glycolic acid

SMILES

OCC(O)=O

InChI Identifier

InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)

InChI Key

AEMRFAOFKBGASW-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy 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

primary alcohol (CHEBI:17497 )
2-hydroxy monocarboxylic acid (CHEBI:17497 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Peroxisome

Biofluid Locations

Not Available

Tissue Locations

Bladder
Fibroblasts
Liver
Skin
Stratum Corneum

Pathways

Name	SMPDB Link	KEGG Link
Primary Hyperoxaluria Type I	SMP00352	Not Available

Applications

keratolytic drug

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	75-80°C
Boiling Point	Not Available
Solubility	1000 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	608 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1	ChemAxon
logS	0.9	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	14.35 m³·mol⁻¹	ChemAxon
Polarizability	6.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-cadf899be6b15d008330	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-e66ed28d8419895e0fb4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0900000000-7f84fac3284d17fa3ba6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-d724c85a3b30e3c2e4bc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7l-9000000000-1e9466549305eb20257b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05i9-9520000000-5f0019fe63eb6e692109	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-004i-9000000000-e942bdae1d60e5f5d649	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9000000000-f225de2de3540c3f50a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00di-9000000000-7de217d97b44f53aad82	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-88af2b259f82cd1d8938	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-c968a24f0640b154325b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-88af2b259f82cd1d8938	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-c968a24f0640b154325b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-004i-9000000000-fa715ee3ce9abbc94edb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 2V, positive	splash10-004i-9000000000-ace3c5f526d28fd24de9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 3V, positive	splash10-004i-9000000000-ff7f922c2460adb6a10d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-004i-9000000000-1d63aaaf9cbc6d3bb3b4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-004j-9000000000-e9c74e7df728e016450c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-002b-9000000000-d0963403f3a8ff9e576d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-002b-9000000000-9e1d6b2e2b889232d610	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0002-9000000000-e9824f68b2176db90d33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-000t-9000000000-02329982bc7150d972bf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 10V, positive	splash10-000t-9000000000-216d8ece56b0a44e5289	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-d961c3c14ec415e3141e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-67f73be970ba9f885c4a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-7445713a5fe347bbc8b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-26e13242443efc1aa846	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-6ba976b949118cd0a86a	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-2885890e3bb8c015742f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (26) ; dermal (26)

Mechanism of Toxicity

Glycolic 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)

Metabolism

The 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. (27)

Toxicity Values

LD50: 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 Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Due 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. (26)

Minimum Risk Level

Not Available

Health Effects

Glycolic 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. (25) 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.

Symptoms

Glycolic acid is a strong irritant. Accumulation of glycolic acid and its metabolite, oxalic acid, causes tachycardia, hypertension, hyperventilation, and metabolic acidosis. (25, 26)

Treatment

Chronic 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.

Concentrations

Not Available

External Links

DrugBank ID

DB03085

HMDB ID

HMDB0000115

FooDB ID

FDB003298

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

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

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14585457

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15662707

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15716481

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15716482

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18498500

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19025792

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21950544

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22044748

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22128110