Showing Compound Hydroxyacetic acid (FDB003298)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:44 UTC

Update date

2020-09-17 15:38:20 UTC

Primary ID

FDB003298

Secondary Accession Numbers

FDB030894

Chemical Information

FooDB Name

Hydroxyacetic acid

Description

Glycolic acid, also known as 2-hydroxyacetate or glycolate, 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. Glycolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycolic acid exists in all living species, ranging from bacteria to humans. In humans, glycolic acid is involved in rosiglitazone metabolism pathway. Outside of the human body, Glycolic acid has been detected, but not quantified in, several different foods, such as sourdocks, pineappple sages, celeriacs, cloves, and feijoa. This could make glycolic acid a potential biomarker for the consumption of these foods. 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. Glycolic acid is a potentially toxic compound. Glycolic acid, with regard to humans, has been found to be associated with several diseases such as transurethral resection of the prostate and biliary atresia; glycolic acid has also been linked to several inborn metabolic disorders including glutaric acidemia type 2, glycolic aciduria, and d-2-hydroxyglutaric aciduria. Glycolic and oxalic acid, along with excess lactic acid, are responsible for the anion gap metabolic acidosis.

CAS Number

79-14-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
α-hydroxyacetic acid	biospider
2-Hydroxy carboxylate	biospider
2-Hydroxy carboxylic acid	biospider
Acetic acid, 2-hydroxy-	biospider
Acetic acid, hydroxy- (9CI)	biospider
Glycolic acid	db_source
α-hydroxyacetate	Generator
α-hydroxyacetic acid	Generator

Predicted Properties

Not Available

Chemical Formula

C2H4O3

IUPAC name

InChI Identifier

InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)

InChI Key

AEMRFAOFKBGASW-UHFFFAOYSA-N

Isomeric SMILES

OCC(O)=O

Average Molecular Weight

76.0514

Monoisotopic Molecular Weight

76.016043994

Classification

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

primary alcohol (CHEBI:17497 )
2-hydroxy monocarboxylic acid (CHEBI:17497 )

Ontology

Dermal

Enteral:

Ingestion

Source:

Biological location:

Tissue and substructures:

Epidermis

Organ and components:

Cell and elements:

Cell:

Fibroblast

Subcellular:

Biofluid and excreta:

Role

Indirect biological role:

Nephrotoxin

Biological role:

Metabolite

Industrial application:

Personal care products

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 31.59%; H 5.30%; O 63.11%	DFC
Melting Point	Mp 80°	DFC
Boiling Point	Bp 100° dec.	DFC
Experimental Water Solubility	Not Available
Experimental logP	-1.11	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 3.82	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available