GLYOXAL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C2H2O2
Molecular Weight	58.0361
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=CC=O

InChI

InChIKey=LEQAOMBKQFMDFZ-UHFFFAOYSA-N

InChI=1S/C2H2O2/c3-1-2-4/h1-2H

HIDE SMILES / InChI

Molecular Formula	C2H2O2
Molecular Weight	58.0361
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29030489 | https://www.ncbi.nlm.nih.gov/pubmed/28106725

Glyoxal refers to the reactive electrophilic species (RES) and is formed during different processes, e.g., lipid peroxidation, DNA oxidation. RES cause the damage of proteins and nucleotides and thus can cause different diseases in human, e.g., diabetes. Glyoxal reacting with free guanines in RNAs can be is used for chemical probing of RNA structure.

Approval Year

PubMed

Title	Date	PubMed
Chemistry and pathobiology of advanced glycation end products.	2001	11125554
Protein glycation: creation of catalytic sites for free radical generation.	2001 Apr	11795527
Synthesis and liquid membrane transport properties of photolabile molecular clips based on dithiane-spiro-crown ethers.	2001 Aug 23	11506596
Proteasome inhibition in glyoxal-treated fibroblasts and resistance of glycated glucose-6-phosphate dehydrogenase to 20 S proteasome degradation in vitro.	2001 Dec 7	11559702
The sugar model: catalysis by amines and amino acid products.	2001 Feb-Apr	11296525
Metabolism of the 2-oxoaldehyde methylglyoxal by aldose reductase and by glyoxalase-I: roles for glutathione in both enzymes and implications for diabetic complications.	2001 Jan 30	11306074
Dialysis-related amyloidosis: pathogenesis focusing on AGE modification.	2001 Mar-Apr	11264780
Peptide and small molecule microarray for high throughput cell adhesion and functional assays.	2001 May-Jun	11353531
Immunological detection of a novel advanced glycation end-product.	2001 Nov	11788793
Total asymmetric synthesis of the putative structure of the cytotoxic diterpenoid (-)-sclerophytin a and of the authentic natural sclerophytins A and B.	2001 Sep 19	11552810
A novel three-component butenolide synthesis.	2001 Sep 6	11529779
Toward new designed proteins derived from bovine pancreatic trypsin inhibitor (BPTI): covalent cross-linking of two 'core modules' by oxime-forming ligation.	2001 Sep-Oct	11562191
Use of Relibase for retrieving complex three-dimensional interaction patterns including crystallographic packing effects.	2001-2002	11987159
Multi site polyadenylation and transcriptional response to stress of a vacuolar type H+-ATPase subunit A gene in Arabidopsis thaliana.	2002 Apr 2	11985780
How hyperglycemia promotes atherosclerosis: molecular mechanisms.	2002 Apr 8	12119059
Alterations in renal mitochondrial respiration in response to the reactive oxoaldehyde methylglyoxal.	2002 Jul	12060586
Combined thioether/hydrazone chemoselective ligation reactions for the synthesis of glycocluster-antigen peptide conjugates.	2002 Jul-Aug	12121146
Conversion of Amadori products of the Maillard reaction to N(epsilon)-(carboxymethyl)lysine by short-term heating: possible detection of artifacts by immunohistochemistry.	2002 Jun	12065691
Molecular structures and excited states of CpM(CO)(2) (Cp = eta(5)-C(5)H(5); M = Rh, Ir) and [Cl(2)Rh(CO)(2)](-). Theoretical evidence for a competitive charge transfer mechanism.	2002 Mar 20	11890817
Polyfluoroether derivatives via nucleophilic fluorination of glyoxal hydrates with deoxofluor.	2002 Mar 22	11895411
The enzymes with benzil reductase activity conserved from bacteria to mammals.	2002 Mar 28	11796169
Chromatographic assay of glycation adducts in human serum albumin glycated in vitro by derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl-carbamate and intrinsic fluorescence.	2002 May 15	11988071

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:23:12 UTC 2023` Edited by `admin` on `Fri Dec 15 17:23:12 UTC 2023`
Record UNII	50NP6JJ975
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLYOXAL

Official Name

English

GLYOXAL [INCI]

Common Name

English

GLYOXAL [MART.]

Common Name

English

GLYOXAL [HSDB]

Common Name

English

DIFORMYL

Common Name

English

OXALALDEHYDE

Systematic Name

English

BIFORMYL

Common Name

English

Glyoxal [WHO-DD]

Common Name

English

ETHANEDIAL

Systematic Name

English

GLYOXAL [MI]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 176.170