Record Information |
---|
Version | 4.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2018-03-12 21:55:20 UTC |
---|
HMDB ID | HMDB0001167 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Pyruvaldehyde |
---|
Description | Pyruvaldehyde is an organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
1,2-Propanedione | ChEBI | 2-Ketopropionaldehyde | ChEBI | 2-Oxopropanal | ChEBI | 2-Oxopropionaldehyde | ChEBI | Acetylformaldehyde | ChEBI | Acetylformyl | ChEBI | alpha-Ketopropionaldehyde | ChEBI | CH3COCHO | ChEBI | Pyruvic aldehyde | ChEBI | a-Ketopropionaldehyde | Generator | α-ketopropionaldehyde | Generator | 1-Ketopropionaldehyde | HMDB | 2-keto Propionaldehyde | HMDB | 2-oxo-Propionaldehyde | HMDB | Ketopropionaldehyde | HMDB | Methylglyoxal | HMDB | Propanedione | HMDB | Propanolone | HMDB | Pyroracemic aldehyde | HMDB | Aldehyde, pyruvic | MeSH | Oxopropanal | MeSH |
|
---|
Chemical Formula | C3H4O2 |
---|
Average Molecular Weight | 72.0627 |
---|
Monoisotopic Molecular Weight | 72.021129372 |
---|
IUPAC Name | 2-oxopropanal |
---|
Traditional Name | methylglyoxal |
---|
CAS Registry Number | 78-98-8 |
---|
SMILES | CC(=O)C=O |
---|
InChI Identifier | InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3 |
---|
InChI Key | AIJULSRZWUXGPQ-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | This compound belongs to the class of organic compounds known as alpha ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Carbonyl compounds |
---|
Direct Parent | Alpha ketoaldehydes |
---|
Alternative Parents | |
---|
Substituents | - Alpha-ketoaldehyde
- Ketone
- Organic oxide
- Hydrocarbon derivative
- Short-chain aldehyde
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | < 25 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-43f9b3c94058c64733b5 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00dj-9000000000-964129275940a60a617d | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-006y-9000000000-0ae1e5fd2d50b28f967c | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00dj-9000000000-964129275940a60a617d | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-9000000000-110d6fcd891f2c54a2cb | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05fr-9000000000-bec3651f9ea6825cf4f7 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-8db5b1ba128748e220c3 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-f968a2358e6fd85ae268 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-0797bdeaa575b54943c5 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0uk9-9000000000-89ef1c082b2ef672eb67 | View in MoNA |
---|
|
---|
General References | - Wondrak GT, Cervantes-Laurean D, Roberts MJ, Qasem JG, Kim M, Jacobson EL, Jacobson MK: Identification of alpha-dicarbonyl scavengers for cellular protection against carbonyl stress. Biochem Pharmacol. 2002 Feb 1;63(3):361-73. [PubMed:11853687 ]
- Mottaran E, Stewart SF, Rolla R, Vay D, Cipriani V, Moretti M, Vidali M, Sartori M, Rigamonti C, Day CP, Albano E: Lipid peroxidation contributes to immune reactions associated with alcoholic liver disease. Free Radic Biol Med. 2002 Jan 1;32(1):38-45. [PubMed:11755315 ]
- Lo TW, Selwood T, Thornalley PJ: The reaction of methylglyoxal with aminoguanidine under physiological conditions and prevention of methylglyoxal binding to plasma proteins. Biochem Pharmacol. 1994 Nov 16;48(10):1865-70. [PubMed:7986197 ]
- Gildersleeve DL, Tobes MC, Natale RB: Rapid analysis for methylglyoxal bis(guanylhydrazone) by reversed-phase ion-pair liquid chromatography. Clin Chem. 1985 Dec;31(12):1979-84. [PubMed:4064286 ]
- Ahmed N, Thornalley PJ, Dawczynski J, Franke S, Strobel J, Stein G, Haik GM: Methylglyoxal-derived hydroimidazolone advanced glycation end-products of human lens proteins. Invest Ophthalmol Vis Sci. 2003 Dec;44(12):5287-92. [PubMed:14638728 ]
- Seppanen P, Alhonen-Hongisto L, Janne J: Polyamine deprivation-induced enhanced uptake of methylglyoxal bis(guanylhydrazone) by tumor cells. Biochim Biophys Acta. 1981 May 5;674(2):169-77. [PubMed:6786360 ]
- Ahmed MU, Brinkmann Frye E, Degenhardt TP, Thorpe SR, Baynes JW: N-epsilon-(carboxyethyl)lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins. Biochem J. 1997 Jun 1;324 ( Pt 2):565-70. [PubMed:9182719 ]
- Riley ML, Harding JJ: The reaction of methylglyoxal with human and bovine lens proteins. Biochim Biophys Acta. 1995 Jan 25;1270(1):36-43. [PubMed:7827133 ]
- Beisswenger PJ, Drummond KS, Nelson RG, Howell SK, Szwergold BS, Mauer M: Susceptibility to diabetic nephropathy is related to dicarbonyl and oxidative stress. Diabetes. 2005 Nov;54(11):3274-81. [PubMed:16249455 ]
- Nemet I, Varga-Defterdarovic L, Turk Z: Preparation and quantification of methylglyoxal in human plasma using reverse-phase high-performance liquid chromatography. Clin Biochem. 2004 Oct;37(10):875-81. [PubMed:15369718 ]
- Thornalley PJ, Argirova M, Ahmed N, Mann VM, Argirov O, Dawnay A: Mass spectrometric monitoring of albumin in uremia. Kidney Int. 2000 Nov;58(5):2228-34. [PubMed:11044246 ]
- Baskaran S, Rajan DP, Balasubramanian KA: Formation of methylglyoxal by bacteria isolated from human faeces. J Med Microbiol. 1989 Mar;28(3):211-5. [PubMed:2926792 ]
- Kuhla B, Luth HJ, Haferburg D, Boeck K, Arendt T, Munch G: Methylglyoxal, glyoxal, and their detoxification in Alzheimer's disease. Ann N Y Acad Sci. 2005 Jun;1043:211-6. [PubMed:16037241 ]
- Schupp N, Schinzel R, Heidland A, Stopper H: Genotoxicity of advanced glycation end products: involvement of oxidative stress and of angiotensin II type 1 receptors. Ann N Y Acad Sci. 2005 Jun;1043:685-95. [PubMed:16037294 ]
- Haik GM Jr, Lo TW, Thornalley PJ: Methylglyoxal concentration and glyoxalase activities in the human lens. Exp Eye Res. 1994 Oct;59(4):497-500. [PubMed:7859825 ]
- Shamsi FA, Lin K, Sady C, Nagaraj RH: Methylglyoxal-derived modifications in lens aging and cataract formation. Invest Ophthalmol Vis Sci. 1998 Nov;39(12):2355-64. [PubMed:9804144 ]
- Jan CR, Chen CH, Wang SC, Kuo SY: Effect of methylglyoxal on intracellular calcium levels and viability in renal tubular cells. Cell Signal. 2005 Jul;17(7):847-55. Epub 2004 Dec 8. [PubMed:15763427 ]
- Ahmed N, Dobler D, Dean M, Thornalley PJ: Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity. J Biol Chem. 2005 Feb 18;280(7):5724-32. Epub 2004 Nov 22. [PubMed:15557329 ]
|
---|