ECHA InfoCard 100.001.059
C 3 H 4 O 2
g·mol 72.063 −1
1.046 g/cm 3
72 °C (162 °F; 345 K)
GHS Signal word
H290, H302, H315, H317, H318, H319, H335, H341
P201, P202, P234, P261, P264, P270, P271, P272, P280, P281, P301+312, P302+352, P304+340, P305+351+338, P308+313, P310, P312, P321, P330, P332+313, P333+313, P337+313, P362, P363, P390
Except where otherwise noted, data are given for materials in their
(at 25 °C [77 °F], 100 kPa).
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Methylglyoxal ( MGO) is the organic compound with the formula CH 3C(O)CHO. It is a reduced derivative of pyruvic acid. It is a reactive compound that is implicated in the biology of diabetes. Methylglyoxal is produced industrially by degradation of carbohydrates using overexpressed methylglyoxal synthase.
Gaseous methylglyoxal has two
carbonyl groups, an aldehyde and a ketone. In the presence of water, it exists as hydrates and oligomers. The formation of these hydrates is indicative of the high reactivity of MGO, which is relevant to its biological behavior.
Biosynthesis and biodegradation
In organisms, methylglyoxal is formed as a side-product of several
metabolic pathways. Methylglyoxal mainly arises as side products of  glycolysis involving glyceraldehyde-3-phosphate and dihydroxyacetone phosphate. It is also thought to arise via the degradation of acetone and threonine. Illustrative of the myriad pathways to MGO,  aristolochic acid caused 12-fold increase of methylglyoxal from 18 to 231 μg/mg of kidney protein in poisoned mice. It may form from  3-aminoacetone, which is an intermediate of threonine catabolism, as well as through lipid peroxidation. However, the most important source is glycolysis. Here, methylglyoxal arises from nonenzymatic phosphate elimination from glyceraldehyde phosphate and dihydroxyacetone phosphate (DHAP), two intermediates of glycolysis. This conversion is the basis of a potential biotechnological route to the commodity chemical 1,2-propanediol.
Since methylglyoxal is highly
cytotoxic, several detoxification mechanisms have evolved. One of these is the glyoxalase system. Methylglyoxal is detoxified by glutathione. Glutathione reacts with methylglyoxal to give a hemithioacetal, which converted into S- D-lactoyl-glutathione by glyoxalase I. This thioester is hydrolyzed to  by D-lactate glyoxalase II.
Methylglyoxal is involved in the formation of
advanced glycation endproducts (AGEs). In this process, methylglyoxal reacts with free amino groups of  lysine and arginine and with thiol groups of cysteine forming AGEs. Histones are also heavily susceptible to modification by methylglyoxal and these modifications are elevated in breast cancer. 
AGEs derived from the action of methylglyoxal on arginine.
Due to increased blood glucose levels, methylglyoxal has higher concentrations in
diabetics and has been linked to arterial atherogenesis. Damage by methylglyoxal to low-density lipoprotein through glycation causes a fourfold increase of atherogenesis in diabetics. Methylglyoxal binds directly to the nerve endings and by that increases the chronic extremity soreness in  diabetic neuropathy. 
Methylglyoxal is a component of some kinds of honey, including
mānuka honey; it appears to have activity against and E. coli and may help prevent formation of S. aureus biofilms formed by . P. aeruginosa
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