Showing Compound Hydroxyacetic acid (FDB003298)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:44 UTC

Update date

2019-11-26 02:58:51 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. Glycolic acid has been detected, but not quantified in, several different foods, such as canola, guava, lingonberries, wild celeries, and sweet marjorams. This could make glycolic acid a potential biomarker for the consumption of these foods. Glycolic acid is a potentially toxic compound. Glycolic acid has been found to be associated with several diseases such as lung cancer, ethylene glycol poisoning, colorectal cancer, and hemodialysis; also glycolic acid has been linked to the inborn metabolic disorders including d-2-hydroxyglutaric aciduria.

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

Property	Value	Source
Water Solubility	608 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1	ChemAxon
logS	0.9	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	14.35 m³·mol⁻¹	ChemAxon
Polarizability	6.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C2H4O3

IUPAC name

2-hydroxyacetic acid

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

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-cadf899be6b15d008330	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-e66ed28d8419895e0fb4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0900000000-7f84fac3284d17fa3ba6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-d724c85a3b30e3c2e4bc	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7l-9000000000-1e9466549305eb20257b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05i9-9520000000-5f0019fe63eb6e692109	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-004i-9000000000-e942bdae1d60e5f5d649	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9000000000-f225de2de3540c3f50a4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00di-9000000000-7de217d97b44f53aad82	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-88af2b259f82cd1d8938	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-c968a24f0640b154325b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-88af2b259f82cd1d8938	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-c968a24f0640b154325b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-d961c3c14ec415e3141e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-67f73be970ba9f885c4a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-7445713a5fe347bbc8b8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-26e13242443efc1aa846	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-6ba976b949118cd0a86a	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-2885890e3bb8c015742f	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer