Hydroxyacetate
Grundinformationen
- CAS
666-14-8- Standard-SMILES
O=C([O-])CO- InChIKey
AEMRFAOFKBGASW-UHFFFAOYSA-M- Summenformel
- C2H3O3-
- Durchschnittliche Molmasse
- 75,04 g/mol
- Monoisotopische Masse
- 75,00876754
Überblick
Glycolate is a hydroxy monocarboxylic acid anion that is acetate where the methyl group has been hydroxylated. It has a role as a human metabolite and an algal metabolite. It is functionally related to an acetate. It is a conjugate base of a glycolic acid.
Namen und Bezeichner
- Bevorzugter Name
- Hydroxyacetate
- IUPAC
- 2-hydroxyacetate
Namen und Synonyme
Datenbank-Bezeichner
- CAS
666-14-8- PubChem CID
- 5460308
- DTXSID
DTXSID901036536- ChEBI
CHEBI:29805- Nikkaji
- J816.702H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,2
- Polarare Oberfläche (TPSA)
- 60,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 5
- Formalladung
- -1
- Komplexität
- 34,6
Sicherheit und Regulatorisches
Toxikologische Informationen
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.
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. (L1023) 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.
Toxicity Summary
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. (A612, A613)
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
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. (T29)
Verwendung und Herstellung
Uses
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. (L1909)
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