| Identification | More | [Name]
Methylglyoxal | [CAS]
78-98-8 | [Synonyms]
2-Ketopropionaldehyde
2-oxopropanal
ACETYLFORMALDEHYDE
FEMA 2969
METHYLGLYOXAL
PYRUVALDEHYDE
PYRUVIC ALDEHYDE
1,2-Propanedione
1-Ketopropionaldehyde
2-oxo-propana
2-oxo-propionaldehyd
Acetylformyl
alpha-Ketopropionaldehyde
CH3COCHO
Glyoxal, methyl
glyoxal,methyl
NSC 79019
nsc79019
Propanal,2-oxo-
Propanedione | [EINECS(EC#)]
201-164-8 | [Molecular Formula]
C3H4O2 | [MDL Number]
MFCD00006960 | [Molecular Weight]
72.06 | [MOL File]
78-98-8.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow to yellow-brown solution | [Melting point ]
25 °C
| [Boiling point ]
72 °C
| [density ]
1.19 g/mL at 20 °C
| [vapor pressure ]
25.09hPa at 20℃ | [FEMA ]
2969 | [refractive index ]
n20/D 1.4209
| [RTECS ]
UZ0700000 | [storage temp. ]
2-8°C
| [solubility ]
DMSO (Slightly), Methanol (Slightly), Water (Soluble) | [form ]
Solution | [color ]
Clear yellow to yellow-brown | [Odor]
at 1.00 % in propylene glycol. sweet acidic ethereal brown rum | [Odor Type]
caramellic | [Water Solubility ]
>=10 g/100 mL at 17 ºC | [Sensitive ]
Air Sensitive | [JECFA Number]
937 | [Merck ]
14,6081 | [BRN ]
906750 | [InChIKey]
AIJULSRZWUXGPQ-UHFFFAOYSA-N | [LogP]
-1.06 at 25℃ | [Uses]
Organic synthesis, as of complex chemical com-
pounds such as pyrethrins, tanning leather, flavor-
ing. | [CAS DataBase Reference]
78-98-8(CAS DataBase Reference) | [IARC]
3 (Vol. 51) 1991 | [NIST Chemistry Reference]
Propanal, 2-oxo-(78-98-8) | [EPA Substance Registry System]
78-98-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 3265 8 / PGIII | [WGK Germany ]
-
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29121900 | [Hazardous Substances Data]
78-98-8(Hazardous Substances Data) |
| Hazard Information | Back Directory | [General Description]
Clear yellow slightly viscous liquid with a pungent odor. Yellowish-green vapors. Faintly acidic to litmus. | [Reactivity Profile]
METHYLGLYOXAL(78-98-8) polymerizes readily. METHYLGLYOXAL(78-98-8) is hygroscopic. This chemical is incompatible with strong oxidizing agents and bases. METHYLGLYOXAL(78-98-8) is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. | [Air & Water Reactions]
Water soluble. | [Fire Hazard]
Literature sources indicate that this chemical is nonflammable. | [Occurrence]
Reported found in the dry distillate of Manilla copal. Also reported found in apple juice, orange juice, celery root, rutabaga, tomato, wheaten bread, white bread, roasted and raw turkey, cognac, roasted barley, beer, cocoa, coffee and roasted pecans. | [Definition]
ChEBI: A 2-oxo aldehyde derived from propanal. | [Preparation]
By distilling a dilute solution of dihydroxyacetone from calcium carbonate; by oxidation of acetone with selenium dioxide; by heating dihydroxy acetone with phosphorus pentoxide; by warming isonitroso acetone with diluted H2SO4. | [Taste threshold values]
Taste characteristics at 0.1%: sweet, caramellic with a dairy creamy nuance | [Flammability and Explosibility]
Nonflammable | [Environmental Fate]
Methylglyoxal production and use as a chemical intermediate
and flavoring agent may result in its release to the environment
through various waste streams. If released into water, MG is not
expected to adsorb to suspended solids and sediment based on
the estimated Koc. Volatilization from water surfaces is not
expected to be an important fate process based upon the estimated
Henry’s Law constant. If released to soil, MG is expected
to have very high mobility based upon an estimated Koc of 1
determined from the structure estimation method. Hydrolysis
is not expected to be an important environmental fate process
since this compound lacks functional groups that hydrolyze
under environmental conditions.
Methylglyoxal serves as a substrate for the isozymes E1, E2,
and E3 of human aldehyde dehydrogenase. Oxidation of MG
by these isozymes generated pyruvate. Methylglyoxal is
a partially oxidized compound obtained from the tropospheric
oxidation of numerous hydrocarbons, of both biogenic and
anthropogenic origin. If released to the air, an estimated vapor
pressure of 27 mm Hg at 25 ℃ indicates MG will exist solely as
a vapor in the atmosphere. Vapor-phase MG will be degraded
in the atmosphere by reaction with photochemically produced
hydroxyl radicals; the half-life for this reaction in air is estimated
to be 30 h. Methylglyoxal absorbs light at wavelengths
>290 nm and, therefore, is susceptible to direct photolysis by
sunlight; half-lives of 2–4 h have been reported. | [storage]
Store at 2-8°C | [Purification Methods]
Commercial 30% (w/v) aqueous solution is diluted to about 10% and distilled twice, taking the fraction boiling below 50o/20mm Hg. (This treatment does not remove lactic acid). [Beilstein 1 IV 3631.] | [Toxicity evaluation]
Endogenously formed MG modifies arginine and lysine residues
in proteins that form AGEs, which have been associated
with diabetic complications and some neurodegenerative
diseases. In different cell lines, MG treatment has been shown to induce apoptosis as measured by nuclear fragmentation and
apoptotic body formation, indicating an increase in apoptosis.
At the mitochondrial level, exogenous MG is highly toxic as it
promotes proliferation, swelling, and membrane derangement.
In both in vitro and in vivo studies, MG treatment has been
shown to significantly reduce antioxidant enzymes and elevate
reactive oxygen species that lead to oxidative stress-mediated
cell death. Genotoxicity has been observed in both in vivo
and in vitro studies, as MG is capable of binding to cellular
macromolecules and forming DNA adducts. |
| Questions And Answer | Back Directory | [Chemical Properties]
Methylglyoxal (MG, C3H4O2) is also known as 2-oxopropanal, pyruvaldehyde, pyruvic aldehyde, 2-ketopropionaldehyde, acetylformaldehyde, propanedione, or propionaldehyde, which is a clear yellow slightly viscous liquid with a pungent odor which polymerizes readily and forms a variety of cyclic and acyclic structures. It is faintly acidic to litmus. The solubility of methylglyoxal is more than 10 g/100 mL water at 17°C. In water, MG is present mostly in the mono and dihydrate forms, while non hydrated MG is only present in traces.
| [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.
| [Sources]
Many food products, beverages, water, rain, clouds, fog water, and urban atmosphere as well as cigarette smoke represent exogenous sources of methylglyoxal. The origins of MG in food and beverages are sugars, the products of the Maillard reaction, lipids and microorganisms formed during industrial processing, cooking, and prolonged storage. In vivo Methylglyoxal can be formed in many enzymatic and nonenzymatic pathways. Enzymatic pathways include reactions catalyzed by triosephosphate isomerase, cytochrome P450 2E1, myeloperoxidase, and aminooxidase, whereas nonenzymatic pathways include decomposition of dihydroxyacetone phosphate (DAP), the Maillard reaction, oxidation of acetol, and lipid peroxidation.
| [References]
https://en.wikipedia.org/wiki/Methylglyoxal
https://pubchem.ncbi.nlm.nih.gov/compound/880#section=Top
http://www.cancertreatmentsresearch.com/methilglyoxal/
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