Hydroxyacetate

HCID 5460308

基本情報

CAS
666-14-8
標準SMILES
O=C([O-])CO
InChIKey
AEMRFAOFKBGASW-UHFFFAOYSA-M
分子式
C2H3O3-
平均分子量
75.04 g/mol
単同位体質量
75.00876754

概要

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.

名称と識別子

優先名称
Hydroxyacetate
IUPAC
2-hydroxyacetate

名称と別名

hydroxyacetate666-14-8RefChem:3483852-hydroxyacetateAcetic acid, hydroxy-, ion(1-)glycolate anionAEMRFAOFKBGASW-UHFFFAOYSA-MDTXSID901036536Q27104089

データベース識別子

CAS
666-14-8
PubChem CID
5460308
DTXSID
DTXSID901036536
ChEBI
CHEBI:29805
Nikkaji
J816.702H

物性

構造計算による物性

XLogP
-0.2
極性表面積
60.4 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
0
重原子数
5

安全と法規制

毒性情報

Treatment · 1 件

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 · 1 件

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.

Exposure RoutesOral (L1909) ; dermal (L1909)
Toxicity Summary · 1 件

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)

Signs and SymptomsGlycolic acid is a strong irritant. Accumulation of glycolic acid and its metabolite, oxalic acid, causes tachycardia, hypertension, hyperventilation, and metabolic acidosis. (L1023, L1909)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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)

用途と製造

Uses · 1 件

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)

関連反応

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