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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-12-01 23:10:25 UTC
HMDB IDHMDB00115
Secondary Accession Numbers
  • HMDB03035
Metabolite Identification
Common NameGlycolic acid
DescriptionGlycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA). In its pure form, glycolic acid is a colorless crystalline solid. Due to its excellent capability to penetrate skin, glycolic acid finds applications in skin care products, most often as a chemical peel. Glycolic acid is also used for tattoo removal.
Structure
Thumb
Synonyms
  1. 2-Hydroxyacetate
  2. 2-Hydroxyacetic acid
  3. a-Hydroxyacetate
  4. a-Hydroxyacetic acid
  5. alpha-Hydroxyacetate
  6. alpha-Hydroxyacetic acid
  7. Glycocide
  8. Glycolate
  9. Glycolic acid
  10. Glycollate
  11. Glycollic acid
  12. GlyPure
  13. GlyPure 70
  14. Hydroxyacetate
  15. Hydroxyacetic acid
  16. Hydroxyethanoate
  17. Hydroxyethanoic acid
  18. Sodium glycolate
Chemical FormulaC2H4O3
Average Molecular Weight76.0514
Monoisotopic Molecular Weight76.016043994
IUPAC Name2-hydroxyacetic acid
Traditional Namehydroxyacetic acid
CAS Registry Number79-14-1
SMILES
OCC(O)=O
InChI Identifier
InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
InChI KeyAEMRFAOFKBGASW-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassHydroxy Acids and Derivatives
Sub ClassAlpha Hydroxy Acids and Derivatives
Other Descriptors
  • 2-hydroxy monocarboxylic acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • primary alcohol(ChEBI)
Substituents
  • Carboxylic Acid
  • Primary Alcohol
Direct ParentAlpha Hydroxy Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
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 Solubility608.0ALOGPS
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
Spectra
SpectraGC-MSMS/MSLC-MSMS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Liver
  • Skin
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.9 +/- 2.4 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.8 +/- 1.7 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified54.0 +/- 50.0 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
FecesDetected and Quantified174.882 +/- 63.115 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified8.64 +/- 3.09 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified9.67 +/- 3.35 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified10.7 +/- 1.79 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified10.9 +/- 2.45 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Dame, ZT. et al. ...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Dame, ZT. et al. ...
details
SalivaDetected and Quantified21.65 +/- 13.0 uMAdult (>18 years old)BothNormal
    • Dame, ZT. et al. ...
details
UrineDetected and Quantified57.00 (11.00-103.00) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified67.9 (36.0-324.4) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified30.0 (15.8-52.6) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified41.6 (3.7-122.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified38.10 +/- 27.35 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified64.0 (21.0-107.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified32.8 (8.8-71.6) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified248.5(72.0-425.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified169.5 (46.0-293.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified128.0 (48.0-208.0) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified110.0 (34.0-186.0) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified35 (18-55) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified39.4 (2.9-78.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified39.6 (16.7-89.1) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified77.1 (33.1-122.0) umol/mmol creatinineChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.3 +/- 10.1 uMAdult (>18 years old)Both
Hemodialysis
details
BloodDetected and Quantified0.6 +/- 2.3 uMAdult (>18 years old)Both
Hemodialysis
details
BloodDetected and Quantified48.0 (40.0 - 56.0) uMAdult (>18 years old)BothEthylene Glycol Poisoning details
Cerebrospinal Fluid (CSF)Detected and Quantified1868 uMAdult (>18 years old)BothTransurethral prostatectomy syndrome details
UrineDetected and Quantified300.00 (100.00-500.00) umol/mmol creatinineChildren (1-13 years old)BothPrimary hyperoxaluria I details
UrineDetected and Quantified23.0 +/- 14.0 umol/mmol creatinineAdult (>18 years old)BothLung cancer details
UrineDetected and Quantified0.40 +/- 0.36 umol/mmol creatinineAdult (>18 years old)BothBiliary atresia details
Associated Disorders and Diseases
Disease References
Biliary atresia
  1. Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. Pubmed: 3944741
Ethylene glycol poisoning
  1. Jacobsen D, Hewlett TP, Webb R, Brown ST, Ordinario AT, McMartin KE: Ethylene glycol intoxication: evaluation of kinetics and crystalluria. Am J Med. 1988 Jan;84(1):145-52. Pubmed: 3337119
Hemodialysis
  1. Ogawa Y, Machida N, Jahana M, Gakiya M, Chinen Y, Oda M, Morozumi M, Sugaya K: Major factors modulating the serum oxalic acid level in hemodialysis patients. Front Biosci. 2004 Sep 1;9:2901-8. Pubmed: 15353324
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. Pubmed: 18953024
Transurethral resection of the prostate
  1. Perier C, Mahul P, Molliex S, Auboyer C, Frey J: Progressive changes in glycine and glycine derivatives in plasma and cerebrospinal fluid after transurethral prostatic resection. Clin Chem. 1990 Dec;36(12):2152-3. Pubmed: 2253377
Primary hyperoxaluria I
  1. MetaGene
Associated OMIM IDs
DrugBank IDDB03085
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003298
KNApSAcK IDC00007461
Chemspider ID737
KEGG Compound IDC00160
BioCyc IDGLYCOLLATE
BiGG ID34090
Wikipedia LinkGlycolic acid
NuGOwiki LinkHMDB00115
Metagene LinkHMDB00115
METLIN ID3219
PubChem Compound757
PDB IDGOA
ChEBI ID17497
References
Synthesis ReferenceWitzemann, Edgar J. Preparation of glycollic acid. Journal of the American Chemical Society (1917), 39 109-12.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  3. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
  4. Horikoshi T, Matsumoto M, Usuki A, Igarashi S, Hikima R, Uchiwa H, Hayashi S, Brysk MM, Ichihashi M, Funasaka Y: Effects of glycolic acid on desquamation-regulating proteinases in human stratum corneum. Exp Dermatol. 2005 Jan;14(1):34-40. Pubmed: 15660917
  5. DiNardo JC, Grove GL, Moy LS: Clinical and histological effects of glycolic acid at different concentrations and pH levels. Dermatol Surg. 1996 May;22(5):421-4. Pubmed: 8634803
  6. Marangella M, Petrarulo M, Bianco O, Vitale C, Finocchiaro P, Linari F: Glycolate determination detects type I primary hyperoxaluria in dialysis patients. Kidney Int. 1991 Jan;39(1):149-54. Pubmed: 2002628
  7. Tsiafoulis CG, Prodromidis MI, Karayannis MI: Development of amperometric biosensors for the determination of glycolic acid in real samples. Anal Chem. 2002 Jan 1;74(1):132-9. Pubmed: 11795781
  8. Porter WH, Rutter PW, Yao HH: Simultaneous determination of ethylene glycol and glycolic acid in serum by gas chromatography-mass spectrometry. J Anal Toxicol. 1999 Nov-Dec;23(7):591-7. Pubmed: 10595845
  9. Jacobsen D, Hewlett TP, Webb R, Brown ST, Ordinario AT, McMartin KE: Ethylene glycol intoxication: evaluation of kinetics and crystalluria. Am J Med. 1988 Jan;84(1):145-52. Pubmed: 3337119
  10. Bernstein EF, Lee J, Brown DB, Yu R, Van Scott E: Glycolic acid treatment increases type I collagen mRNA and hyaluronic acid content of human skin. Dermatol Surg. 2001 May;27(5):429-33. Pubmed: 11359487
  11. Leumann EP, Dietl A, Matasovic A: Urinary oxalate and glycolate excretion in healthy infants and children. Pediatr Nephrol. 1990 Sep;4(5):493-7. Pubmed: 2242313
  12. Booth ED, Dofferhoff O, Boogaard PJ, Watson WP: Comparison of the metabolism of ethylene glycol and glycolic acid in vitro by precision-cut tissue slices from female rat, rabbit and human liver. Xenobiotica. 2004 Jan;34(1):31-48. Pubmed: 14742135
  13. Mahul P, Molliex S, Auboyer C, Levigne F, Jospe R, Dumont A, Gilloz A: [Neurotoxic role of glycocolle and derivatives in transurethral resection of the prostate] Ann Fr Anesth Reanim. 1993;12(5):512-4. Pubmed: 8311360
  14. Marangella M, Petrarulo M, Vitale C, Cosseddu D, Linari F: Plasma and urine glycolate assays for differentiating the hyperoxaluria syndromes. J Urol. 1992 Sep;148(3 Pt 2):986-9. Pubmed: 1507356
  15. Effendy I, Kwangsukstith C, Lee JY, Maibach HI: Functional changes in human stratum corneum induced by topical glycolic acid: comparison with all-trans retinoic acid. Acta Derm Venereol. 1995 Nov;75(6):455-8. Pubmed: 8651024
  16. Pien K, van Vlem B, van Coster R, Dacremont G, Piette M: An inherited metabolic disorder presenting as ethylene glycol intoxication in a young adult. Am J Forensic Med Pathol. 2002 Mar;23(1):96-100. Pubmed: 11953504
  17. Dietzen DJ, Wilhite TR, Kenagy DN, Milliner DS, Smith CH, Landt M: Extraction of glyceric and glycolic acids from urine with tetrahydrofuran: utility in detection of primary hyperoxaluria. Clin Chem. 1997 Aug;43(8 Pt 1):1315-20. Pubmed: 9267307
  18. Newman N, Newman A, Moy LS, Babapour R, Harris AG, Moy RL: Clinical improvement of photoaged skin with 50% glycolic acid. A double-blind vehicle-controlled study. Dermatol Surg. 1996 May;22(5):455-60. Pubmed: 8634809
  19. Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. Pubmed: 6592775
  20. Porter WH, Rutter PW, Bush BA, Pappas AA, Dunnington JE: Ethylene glycol toxicity: the role of serum glycolic acid in hemodialysis. J Toxicol Clin Toxicol. 2001;39(6):607-15. Pubmed: 11762669

Enzymes

General function:
Involved in glucose-6-phosphate dehydrogenase activity
Specific function:
Produces pentose sugars for nucleic acid synthesis and main producer of NADPH reducing power.
Gene Name:
G6PD
Uniprot ID:
P11413
Molecular weight:
62467.88
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Enzyme with hydroxy-pyruvate reductase, glyoxylate reductase and D-glycerate dehydrogenase enzymatic activities. Reduces hydroxypyruvate to D-glycerate, glyoxylate to glycolate oxidizes D-glycerate to hydroxypyruvate.
Gene Name:
GRHPR
Uniprot ID:
Q9UBQ7
Molecular weight:
35667.875
Reactions
Glycolic acid + NADP → Glyoxylic acid + NADPHdetails
Glycolic acid + NADP → Glyoxylic acid + NADPH + Hydrogen Iondetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE).
Gene Name:
CYP4A11
Uniprot ID:
Q02928
Molecular weight:
59347.31
Reactions
Fatty acid + Oxygen + Reduced flavoprotein → Glycolic acid + Oxidized flavoprotein + Waterdetails
General function:
Involved in FMN binding
Specific function:
Has 2-hydroxyacid oxidase activity. Most active on the 2-carbon substrate glycolate, but is also active on 2-hydroxy fatty acids, with high activity towards 2-hydroxy palmitate and 2-hydroxy octanoate.
Gene Name:
HAO1
Uniprot ID:
Q9UJM8
Molecular weight:
40923.945
Reactions
Glycolic acid + Oxygen → Glyoxylic acid + Hydrogen peroxidedetails
General function:
Involved in FMN binding
Specific function:
Catalyzes the oxidation of L-alpha-hydroxy acids as well as, more slowly, that of L-alpha-amino acids.
Gene Name:
HAO2
Uniprot ID:
Q9NYQ3
Molecular weight:
38838.35
Reactions
Glycolic acid + Oxygen → Glyoxylic acid + Hydrogen peroxidedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGP
Uniprot ID:
A6NDG6
Molecular weight:
34005.69
Reactions
Phosphoglycolic acid + Water → Glycolic acid + Phosphoric aciddetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate and palmitate. Shows no activity towards arachidonic acid and prostaglandin A1. Lacks functional activity in the kidney and does not contribute to renal 20-hydroxyeicosatetraenoic acid (20-HETE) biosynthesis.
Gene Name:
CYP4A22
Uniprot ID:
Q5TCH4
Molecular weight:
59245.28
Reactions
Fatty acid + Oxygen + Reduced flavoprotein → Glycolic acid + Oxidized flavoprotein + Waterdetails