Human Metabolome Database Version 3.5

Showing metabocard for Glycolic acid (HMDB00115)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:54 -0700
HMDB ID HMDB00115
Secondary Accession Numbers
  • HMDB03035
Metabolite Identification
Common Name Glycolic acid
Description Glycolic 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C2H4O3
Average Molecular Weight 76.0514
Monoisotopic Molecular Weight 76.016043994
IUPAC Name 2-hydroxyacetic acid
Traditional IUPAC Name hydroxyacetic acid
CAS Registry Number 79-14-1
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
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Hydroxy Acids and Derivatives
Sub Class Alpha Hydroxy Acids and Derivatives
Other Descriptors
  • 2-hydroxy monocarboxylic acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • primary alcohol(ChEBI)
Substituents
  • Carboxylic Acid
  • Primary Alcohol
Direct Parent Alpha Hydroxy Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Mitochondria
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 75 - 80 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -1.11 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 608 g/L ALOGPS
LogP -1.02 ALOGPS
LogP -1 ChemAxon
LogS 0.90 ALOGPS
pKa (strongest acidic) 3.53 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 14.35 ChemAxon
Polarizability 6.2 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Liver
  • Skin
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
7.9 +/- 2.4 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
7.8 +/- 1.7 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
54.0 +/- 50.0 uM Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
57.00 (11.00-103.00) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
67.9 (36.0-324.4) umol/mmol creatinine Adolescent (13-18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
30.0 (15.8-52.6) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
41.6 (3.7-122.1) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
38.10 +/- 27.35 umol/mmol creatinine Children (1-13 year old) Not Specified Comment Normal
Urine Detected and Quantified
64.0 (21.0-107.0) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
32.8 (8.8-71.6) umol/mmol creatinine Newborn (0-30 days old) Both Normal
Urine Detected and Quantified
248.5(72.0-425.0) umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected and Quantified
169.5 (46.0-293.0) umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected and Quantified
128.0 (48.0-208.0) umol/mmol creatinine Children (1-13 year old) Both Normal
Urine Detected and Quantified
110.0 (34.0-186.0) umol/mmol creatinine Adolescent (13-18 years old) Both Normal
Urine Detected and Quantified
35 (18-55) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
39.4 (2.9-78.1) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
39.6 (16.7-89.1) umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected and Quantified
77.1 (33.1-122.0) umol/mmol creatinine Children (1-13 year old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 7.3 +/- 10.1 uM Adult (>18 years old) Both Comment Hemodialysis
Blood Detected and Quantified 0.6 +/- 2.3 uM Adult (>18 years old) Both Comment Hemodialysis
Blood Detected and Quantified 48.0 (40.0 - 56.0) uM Adult (>18 years old) Both Ethylene Glycol Poisoning
Cerebrospinal Fluid (CSF) Detected and Quantified 1868 uM Adult (>18 years old) Both Transurethral Prostatic Resection
Urine Detected and Quantified 300.00 (100.00-500.00) umol/mmol creatinine Children (1-13 year old) Both Primary hyperoxaluria I
Urine Detected and Quantified 23.0 +/- 14.0 umol/mmol creatinine Adult (>18 years old) Both Lung cancer
Urine Detected and Quantified 0.40 +/- 0.36 umol/mmol creatinine Adult (>18 years old) Both Biliary atresia
Associated Disorders and Diseases
Disease References
Ethylene glycol poisoning
  • 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 Link_out
      Transurethral resection of the prostate
      • 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 Link_out
          Lung Cancer
          • 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 Link_out
              Hemodialysis
              • 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 Link_out
                  Primary hyperoxaluria I, PH1
                      Biliary atresia
                      • 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 Link_out
                          Associated OMIM IDs
                          DrugBank ID DB03085 Link_out
                          DrugBank Metabolite ID Not Available
                          Phenol Explorer Compound ID Not Available
                          Phenol Explorer Metabolite ID Not Available
                          FoodDB ID FDB003298
                          KNApSAcK ID C00007461 Link_out
                          Chemspider ID 737 Link_out
                          KEGG Compound ID C00160 Link_out
                          BioCyc ID GLYCOLLATE Link_out
                          BiGG ID 34090 Link_out
                          Wikipedia Link Glycolic acid Link_out
                          NuGOwiki Link HMDB00115 Link_out
                          Metagene Link HMDB00115 Link_out
                          METLIN ID 3219 Link_out
                          PubChem Compound 757 Link_out
                          PDB ID GOA Link_out
                          ChEBI ID 17497 Link_out
                          References
                          Synthesis Reference Witzemann, 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. 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 Link_out
                          2. 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 Link_out
                          3. 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 Link_out
                          4. 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 Link_out
                          5. 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 Link_out
                          6. 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 Link_out
                          7. 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 Link_out
                          8. 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 Link_out
                          9. 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 Link_out
                          10. 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 Link_out
                          11. 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 Link_out
                          12. 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 Link_out
                          13. 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 Link_out
                          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 Link_out
                          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 Link_out
                          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 Link_out
                          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 Link_out
                          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 Link_out
                          19. Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. Pubmed: 6592775 Link_out
                          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 Link_out

                          Enzymes
                          Name: Glucose-6-phosphate 1-dehydrogenase
                          Reactions: Not Available
                          Gene Name: G6PD
                          Uniprot ID: P11413 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Glyoxylate reductase/hydroxypyruvate reductase
                          Reactions:
                          Glycolic acid + NADP unknown Glyoxylic acid + NADPH details
                          Glycolic acid + NADP unknown Glyoxylic acid + NADPH + Hydrogen Ion details
                          Gene Name: GRHPR
                          Uniprot ID: Q9UBQ7 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Cytochrome P450 4A11
                          Reactions:
                          Fatty acid + Oxygen + Reduced flavoprotein unknown Glycolic acid + Oxidized flavoprotein + Water details
                          Gene Name: CYP4A11
                          Uniprot ID: Q02928 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Hydroxyacid oxidase 1
                          Reactions:
                          Glycolic acid + Oxygen unknown Glyoxylic acid + Hydrogen peroxide details
                          Gene Name: HAO1
                          Uniprot ID: Q9UJM8 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Hydroxyacid oxidase 2
                          Reactions:
                          Glycolic acid + Oxygen unknown Glyoxylic acid + Hydrogen peroxide details
                          Gene Name: HAO2
                          Uniprot ID: Q9NYQ3 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Phosphoglycolate phosphatase
                          Reactions:
                          Phosphoglycolic acid + Water unknown Glycolic acid + Phosphoric acid details
                          Gene Name: PGP
                          Uniprot ID: A6NDG6 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Cytochrome P450 4A22
                          Reactions:
                          Fatty acid + Oxygen + Reduced flavoprotein unknown Glycolic acid + Oxidized flavoprotein + Water details
                          Gene Name: CYP4A22
                          Uniprot ID: Q5TCH4 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA