| Record Information |
|---|
| Version | 1.0 |
|---|
| Created at | 2005-11-16 15:48:42 UTC |
|---|
| Updated at | 2023-04-28 21:51:53 UTC |
|---|
| NP-MRD ID | NP0000402 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | Glycolic acid |
|---|
| Description | Glycolic 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. |
|---|
| Structure | InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5) |
|---|
| 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 Mass | 76.0514 Da |
|---|
| Monoisotopic Mass | 76.01604 Da |
|---|
| IUPAC Name | 2-hydroxyacetic acid |
|---|
| Traditional Name | glycolic 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 |
|---|
| Experimental Spectra |
|---|
|
| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
|---|
| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2023-04-28 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, experimental) | Ahselim | | | 2023-04-28 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
|---|
|
| Not Available | | Chemical Shift Submissions |
|---|
|
| Not Available | | Species |
|---|
| Species of Origin | |
|---|
| Species Where Detected | |
|---|
| 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 | |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | |
|---|
| Predicted Properties | |
|---|
| General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. [PubMed:6592775 ]
- 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 ]
- Hua X, Zhou X, Xu Y: Improving techno-economics of bioproduct glycolic acid by successive recycled-cell catalysis of ethylene glycol with Gluconobacter oxydans. Bioprocess Biosyst Eng. 2018 Oct;41(10):1555-1559. doi: 10.1007/s00449-018-1968-2. Epub 2018 Jun 15. [PubMed:29948215 ]
|
|---|
