AFCDB: Glyoxylic acid (FDB001478)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:59 UTC

Update date

2020-09-17 15:38:20 UTC

Primary ID

FDB001478

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glyoxylic acid

Description

Glyoxylic acid, also known as a-ketoacetate or glyoxalate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Glyoxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom. Glyoxylic acid exists in all living species, ranging from bacteria to humans. L-alanine and glyoxylic acid can be biosynthesized from glycine and pyruvic acid through its interaction with the enzyme serine--pyruvate aminotransferase. In humans, glyoxylic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Outside of the human body, Glyoxylic acid has been detected, but not quantified in, tamarinds. This could make glyoxylic acid a potential biomarker for the consumption of these foods. Glyoxylic acid is a potentially toxic compound. Glyoxylic acid, with regard to humans, has been found to be associated with several diseases such as bladder infections and transurethral resection of the prostate; glyoxylic acid has also been linked to the inborn metabolic disorder primary hyperoxaluria I.

CAS Number

298-12-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	224 g/L	ALOGPS
logP	-0.59	ALOGPS
logP	-0.13	ChemAxon
logS	0.48	ALOGPS
pKa (Strongest Acidic)	2.61	ChemAxon
pKa (Strongest Basic)	-9.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	13.5 m³·mol⁻¹	ChemAxon
Polarizability	5.35 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

C2H2O3

IUPAC name

2-oxoacetic acid

InChI Identifier

InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)

InChI Key

HHLFWLYXYJOTON-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C=O

Average Molecular Weight

74.0355

Monoisotopic Molecular Weight

74.00039393

Classification

Description

Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic acids

Alternative Parents

Substituents

Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:16891 )
aldehydic acid (CHEBI:16891 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	V. deliquescent prisms giving yellow aq. soln.	CCD
Mass Composition	C 32.45%; H 2.72%; O 64.83%	CCD
Melting Point	Mp 104 - 107° (sinters from 94°)	CCD
Boiling Point	Not Available
Experimental Water Solubility	V. sol. H2O; spar. sol. EtOH, Et2O	CCD
Experimental logP	Not Available
Experimental pKa	p Ka2.32	CCD
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)	splash10-004l-9000000000-a04bafbf8e0b990094a3	2014-09-20	View Spectrum
GC-MS	Glyoxylic acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-03di-3900000000-16bc69e0e9d51e54854e	Spectrum
GC-MS	Glyoxylic acid, non-derivatized, GC-MS Spectrum	splash10-03di-3900000000-16bc69e0e9d51e54854e	Spectrum
Predicted GC-MS	Glyoxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0096-9000000000-042540a05be250278f8b	Spectrum
Predicted GC-MS	Glyoxylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-9200000000-c60b627ed670285ec37f	Spectrum
Predicted GC-MS	Glyoxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glyoxylic acid, TBDMS_1_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)	splash10-00di-9000000000-72c34bc34b8c3341442b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9000000000-920a0dc738957201d4ba	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00di-9000000000-857c7f2d72c3d4c10dbf	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-9b5825d5d9d8b094fefa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9000000000-de556f03ea428deff5e2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00dl-9000000000-74b253632894213d473c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-9b5825d5d9d8b094fefa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-de556f03ea428deff5e2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00dl-9000000000-74b253632894213d473c	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-a8cc2c89793394fdf9e4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-d20183b08984d4766e8a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-ea9968e3933fd734506c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-cef8efc477a2500a7ead	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-3817c0865df629803538	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-bb935f857fb5fd08c7e3	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-8f50f0d32d4c40b5b935	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-b6216caa16afdf328489	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-aa6a654e73df38a43273	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-c6f38ec60bcf8724ecd1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-c6f38ec60bcf8724ecd1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9000000000-641421c616a0929ce01e	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, 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, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum