Methylglyoxal

Base Information

• Chemical Name: Methylglyoxal
• CAS No.: 78-98-8
• Molecular Formula: C3H4O2
• Molecular Weight: 72.0636
• Hs Code.: 29121900
• European Community (EC) Number: 201-164-8
• NSC Number: 626580,133493,133492,79019
• UN Number: 1993
• UNII: 722KLD7415
• DSSTox Substance ID: DTXSID0021628
• Nikkaji Number: J1.489C
• Wikipedia: Methylglyoxal
• Wikidata: Q903881
• Metabolomics Workbench ID: 37635
• ChEMBL ID: CHEMBL170721
• Mol file: 78-98-8.mol

Synonyms:Acetylformaldehyde;Aldehyde, Pyruvic;Methylglyoxal;Oxopropanal;Pyruvaldehyde;Pyruvic Aldehyde

Chemical Property of Methylglyoxal

Chemical Property:

• Appearance/Colour: Clear yellow slightly viscous liquid with a pungent odor
• Vapor Pressure: 121mmHg at 25°C
• Melting Point: 25 ºC
• Refractive Index: n20/D 1.4209
• Boiling Point: 71.999 ºC at 760 mmHg
• Flash Point: 2.468 ºC
• PSA: 34.14000
• Density: 0.994 g/cm³
• LogP: -0.22570
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: >=10 g/100 mL at 17 ºC
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 72.021129366
• Heavy Atom Count: 5
• Complexity: 55.9
• Transport DOT Label: Combustible Liquid

Purity/Quality:

99% ^*data from raw suppliers

Pyruvaldehyde(35%w/waqueous) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi,C
• Statements: 22-36-35
• Safety Statements: 26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: CC(=O)C=O
• Description: Methylglyoxal is an organic compound formed as a side-product of several metabolic pathways. It has been proved to be an intermediate in the metabolism of acetone and its derivatives. It is produced to insure every cell's health, which is used commonly as a reagent in organic synthesis, as a flavoring agent, and in tanning. However, the most important application is in pharmaceuticals. Methylglyoxal is found in all honeys, especially in manuka honey, in which it has strong antibacterial and antiviral property. Methylglyoxal is transferred into the honey where it remains stable. Dietary Methylglyoxal found in Manuka Honey is resistant to heat, light, body fluids and enzymatic activity. This property makes MGO Manuka Honey superior to any other honey. Its anti-cancer potential has been already demonstrated in human body and it has proved to be effective to eradicate most cancer types. Methylglyoxal (MG) is a highly reactive a-dicarbonyl compound that is primarily generated endogenously during glycolytic pathways (glucose and fructose metabolism) in cells and exogenously due to autoxidation of sugar, degradation of lipids, and fermentation during food and drink processing. Methylglyoxal polymerizes readily; it is hygroscopic and incompatible with strong oxidizing agents and bases. Methylglyoxal may be present as a free molecule in the diet or bound to biological materials, such as proteins, and as advanced glycation end products (AGEs), which are poorly absorbed. Methylglyoxal has been indicated in pathological events associated with hyperglycemia in both type 1 and type 2 diabetes and in other diabetic complications as either a direct toxin or as a precursor for AGEs. In animal studies, MG has been shown to induce tumorigenesis, but has also been reported as a tumoristatic agent. Methylglyoxal has been identified as the dominant antibacterial constituent of manuka honey.
• Uses: Organic synthesis, as of complex chemical com- pounds such as pyrethrins, tanning leather, flavor- ing. Used in organic synthesis, as a flavoring agent, and in tanning leather. Commercial formulation is available as a 30% aqueous solution. No safety concern at current levels of intake when used as a flavoring agent. Methylglyoxal solution has been used:to assess glyoxalase 1 (GLO1) enzymatic activityas an advanced glycation end (AGE) forming agent for the preparation of albumin in vitroto regulate anxiety like behavior in miceto induce peritoneal fibrosis in ratsto study the chromatographic retention characteristics of organic chemicals and metal DNA adductsfor intraplantar injection in mice to investigate peripheral and central components of methylglyoxal (MG)-transient receptor potential ankyrin 1 (TRPA1)-adenylyl cyclase 1 isoform (AC1) pathway

Technology Process of Methylglyoxal

There total 354 articles about Methylglyoxal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 24.0%

1-Phenylbut-1-en-3-one (122-57-6) → benzaldehyde (100-52-7) + 2-oxopropanal (78-98-8)

Guidance literature:

With dihydrogen peroxide; In water; acetonitrile; at 20 ℃; for 5h; under 760.051 Torr;

DOI:10.1007/s10562-011-0668-1

Reference yield:

Glycidaldehyde (765-34-4) → DL-glyceraldehyde 3-phosphate (142-10-9,591-57-1,20283-52-7,591-59-3) + acrolein (107-02-8,25068-14-8) + 2-oxopropanal (78-98-8)

Guidance literature:

In aq. phosphate buffer; at 20 ℃; pH=5 - 8;

DOI:10.1039/c7cc02183f

Reference yield:

5-chloro-4-hydroxy-hex-2-enoic acid + ozone (10028-15-6) → ethylglyoxal (4417-81-6) + oxalic acid (144-62-7,97993-78-7) + ethyl acetate (141-78-6) + 2-oxopropanal (78-98-8)

Guidance literature:

upstream raw materials:

pyridine

1-(diethylamino)propan-2-one

dibenzoyl peroxide

4-methyleneoxetan-2-one

Downstream raw materials:

dimethylglyoxal

1-morpholin-4-yl-butane-2,3-dione 2-phenylhydrazone

7-methyl-2,4-diaminopteridine

2-(4-nitro-benzoyloxy)-acetoacetonitrile

Refernces

• 1、 Zhao, Guofeng,Hu, Huanyun,Jiang, Zheng,Zhang, Shuo,Lu, Yong. "NiO-doped Au/Ti-powder: A catalyst with dramatic improvement in activity for gas-phase oxidation of alcohols". . p. 171 - 177. Retrieved 2013.
• 2、 Neuberg,Kobel. "-". . p. 243. Retrieved 1929.
• 3、 Betterton, Eric A.,Hoffmann, Michael R.. "Kinetics, Mechanism, and Thermodynamics of the Reversible Reaction of Methylglyoxal (CH3COCHO) with S(IV)". . p. 3011 - 3020. Retrieved 1987.
• 4、 Raveux. "-". . p. 157. Retrieved 1946.
• 5、 Neuberg,Scheuer. "-". . p. 1031. Retrieved 1929.
• 6、 Kostytschew,Jegorowa. "-". . p. 279. Retrieved 1929.
• 7、 Kloepfer, Antje,Spanneberg, Robert,Glomb, Marcus A.. "Formation of arginine modifications in a model system of N α- Tert -butoxycarbonyl (Boc)-arginine with methylglyoxal". . p. 394 - 401. Retrieved 2011.
• 8、 Kitajima, Nobumasa,Whang, Kaehong,Moro-oka, Yoshihiko,Uchida, Akira,Sasada, Yoshio. "Oxidations of Primary Alcohols with a Copper(II) Complex as a Possible Galactose Oxidase Model". . p. 1504 - 1505. Retrieved 1986.
• 9、 Saraiva, Marco A.,Borges, Carlos M.,Florencio, M. Helena. "Reactions of a modified lysine with aldehydic and diketonic dicarbonyl compounds: An electrospray mass spectrometry structure/activity study". . p. 216 - 228. Retrieved 2006.
• 10、 Evans,Hockett. "-". . p. 4384. Retrieved 1931.