AFCDB: 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
Not Available	Not Available

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-2885890e3bb8c015742f	2014-09-20	View Spectrum
GC-MS	Hydroxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	Spectrum
GC-MS	Hydroxyacetic acid, 2 TMS, GC-MS Spectrum	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	Spectrum
GC-MS	Hydroxyacetic acid, 2 TMS, GC-MS Spectrum	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	Spectrum
GC-MS	Hydroxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-cadf899be6b15d008330	Spectrum
GC-MS	Hydroxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-e66ed28d8419895e0fb4	Spectrum
GC-MS	Hydroxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-7f84fac3284d17fa3ba6	Spectrum
GC-MS	Hydroxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	Spectrum
GC-MS	Hydroxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	Spectrum
GC-MS	Hydroxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	Spectrum
GC-MS	Hydroxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-d724c85a3b30e3c2e4bc	Spectrum
Predicted GC-MS	Hydroxyacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a7l-9000000000-1e9466549305eb20257b	Spectrum
Predicted GC-MS	Hydroxyacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05i9-9520000000-5f0019fe63eb6e692109	Spectrum
Predicted GC-MS	Hydroxyacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxyacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxyacetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxyacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxyacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxyacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroxyacetic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-004i-9000000000-e942bdae1d60e5f5d649	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9000000000-f225de2de3540c3f50a4	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00di-9000000000-7de217d97b44f53aad82	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-88af2b259f82cd1d8938	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-c968a24f0640b154325b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-88af2b259f82cd1d8938	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-c968a24f0640b154325b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-004i-9000000000-fa715ee3ce9abbc94edb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 2V, positive	splash10-004i-9000000000-ace3c5f526d28fd24de9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 3V, positive	splash10-004i-9000000000-ff7f922c2460adb6a10d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-004i-9000000000-1d63aaaf9cbc6d3bb3b4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-004j-9000000000-e9c74e7df728e016450c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-002b-9000000000-d0963403f3a8ff9e576d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-002b-9000000000-9e1d6b2e2b889232d610	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0002-9000000000-e9824f68b2176db90d33	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-000t-9000000000-02329982bc7150d972bf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 10V, positive	splash10-000t-9000000000-216d8ece56b0a44e5289	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-d961c3c14ec415e3141e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-67f73be970ba9f885c4a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-7445713a5fe347bbc8b8	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-26e13242443efc1aa846	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-6ba976b949118cd0a86a	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum