Methylglyoxal

Structural formula
General
Surname	Methylglyoxal
other names	2-oxopropanal 2-ketopropanal Pyruvaldehyde
Molecular formula	C 3 H 4 O 2
External identifiers / databases
CAS number 78-98-8 EC number 201-164-8 ECHA InfoCard 100.001.059 PubChem 880 ChemSpider 857 DrugBank DB03587 Wikidata Q903881
properties
Molar mass	72.0627 g mol −1
Physical state	liquid
density	1.0455 g cm −3 (20  ° C )
boiling point	72 ° C
Refractive index	1.4002 (18 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 290-302-317-318-341 P: 305 + 351 + 338
Thermodynamic properties
ΔH f 0	−309.1 kJ / mol
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Methylglyoxal , also known as 2-oxopropanal, is the reduced form of pyruvic acid and has the empirical formula C ₃ H ₄ O ₂ . It has two carbonyl groups and is aldehyde and ketone alike . It is the simplest member of the ketoaldehydes group .

Analytics

The reliable qualitative and quantitative determination in the various test materials is possible after adequate sample preparation by coupling gas chromatography or HPLC with mass spectrometry .

Biological importance

In organisms, methylglyoxal is often produced as a by-product of metabolic processes, especially in connection with glycolysis . It is formed during the non-enzymatic elimination of the phosphate group of glyceraldehyde-3-phosphate or dihydroxyacetone phosphate (DHAP) . Both materials provide intermediates of glycolysis, which in the aldol cleavage of -bisphosphate fructose 1,6 by the aldolase produced. However, since methylglyoxal has a cytotoxic effect, the body has a breakdown mechanism in which the substance is converted into lactate by the enzymes glyoxylase I and glyoxylase II .

The importance of methylglyoxal for the development of diabetic nerve disease was discovered in 2012. Methylglyoxal binds directly to the pain-conducting nerve tracts and makes them overly sensitive.

Methylglyoxal is found in manuka honey in measurable concentrations.

Individual evidence

1. ↑ ^{a b c} David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-440.
2. ↑ Entry on 2-oxopropanal in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
3. ↑ Data sheet Methylglyoxal solution technical, ~ 40% in H ₂ O from Sigma-Aldrich , accessed on January 31, 2017 ( PDF ).
4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-23.
5. ↑ MY Wu, BG Chen, CD Chang, MH Huang, TG Wu, DM Chang, YJ Lee, HC Wang, CI Lee, CL Chern, RH Liu: A novel derivatization approach for simultaneous determination of glyoxal, methylglyoxal, and 3-deoxyglucosone in plasma by gas chromatography-mass spectrometry. In: J Chromatogr A. 1204 (1), Sep 12, 2008, pp. 81-86. PMID 18692194 .
6. ↑ JL Scheijen, CG Schalkwijk: Quantification of glyoxal, methylglyoxal and 3-deoxyglucosone in blood and plasma by ultra performance liquid chromatography tandem mass spectrometry: evaluation of blood specimen. In: Clin Chem Lab Med. 52 (1), Jan 1, 2014, pp. 85-91. PMID 23492564 .
7. ^ S. Oelschlaegel, M. Gruner, PN Wang, A. Boettcher, I. Koelling-Speer, K. Speer: Classification and characterization of manuka honeys based on phenolic compounds and methylglyoxal. In: J Agric Food Chem . 60 (29), Jul 25, 2012, pp. 7229-7237. PMID 22676798 .
8. ^ Y. Inoue, A. Kimura: Methylglyoxal and regulation of its metabolism in microorganisms. In: Advances in Microbial Physiology . Volume 37, 1995, pp. 177-227, PMID 8540421 . (Review).
9. ↑ B. Hellwig: Methylglyoxal intensifies the pain. In: Deutsche Apotheker Zeitung . May 21, 2012.
10. ↑ A. Bierhaus, T. Fleming et al .: Methylglyoxal modification of Nav1.8 facilitates nociceptive neuron firing and causes hyperalgesia in diabetic neuropathy. In: Nature Medicine . Volume 18, Number 6, June 2012, pp. 926-933, doi: 10.1038 / nm.2750 . PMID 22581285 .
11. ↑ E. Rabie, JC Serem, HM Oberholzer, AR Gaspar, MJ Bester: How methylglyoxal kills bacteria: An ultrastructural study. In: Ultrastruct Pathol. 40 (2), 2016, pp. 107–111. PMID 26986806 .