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Malondialdehyde

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Malondialdehyde
Names
IUPAC name propanedial
Identifiers
CAS Number
3D model (JSmol)
KEGG
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • C(C=O)C=O
Properties
Chemical formula C3H4O2
Molar mass 72.0636 g/mol
Melting point 72 °C (162 °F; 345 K)
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Malonaldehyde is the organic compound with the formula CH2(CHO)2. The structure of this species is more complex than this formula suggests. This reactive species occurs naturally and is a marker for oxidative stress.

Structure and synthesis

Malonaldehyde mainly exists in the enol form:

CH2(CHO)2 → HOCH=CH-CHO

In organic solvents, the cis isomer is favored, whereas in water the trans isomer predominates.

Malonaldehyde is a highly reactive compound that is not typically observed in pure form. In the laboratory it can be generated in situ by hydrolysis of 1,1,3,3-tetramethoxypropane, which is commercially available. It is easily deprotonated to give the sodium salt of the enolate (m.p. 245 °C).

Biochemistry

Reactive oxygen species degrade polyunsaturated lipids, forming malondialdehyde. This compound is a reactive aldehyde and is one of the many reactive electrophile species that cause toxic stress in cells and form covalent protein adducts referred to as advanced lipoxidation end-products (ALE), in analogy to advanced glycation end-products (AGE). The production of this aldehyde is used as a biomarker to measure the level of oxidative stress in an organism.

Malonaldehyde reacts with deoxyadenosine and deoxyguanosine in DNA, forming DNA adducts, the primary one being M1G, which is mutagenic. The guanidine group of arginine residues condense with MDA to give 2-aminopyrimidines.

Human ALDH1A1 aldehyde dehydrogenase is capable of oxidising malonaldehyde.

Analysis

MDA and other "thiobarbituric reactive substances" (TBARS) condense with two equivalents of thiobarbituric acid to give a fluorescent red derivative that can be assayed spectrophotometrically. 1-Methyl-2-phenylindole is an alternative more selective reagent.

Hazards

MDA is reactive and potentially mutagenic.

Pathology

Corneas of patients suffering from keratoconus and bullous keratopathy have increased levels of MDA, according to one study. MDA also can be found in tissue sections of joints from patients with osteoarthritis.

See also

References

  1. ^ V. Nair, C. L. O'Neil, P. G. Wang “Malondialdehyde” Encyclopedia of Reagents for Organic Synthesis, 2008, John Wiley & Sons, New York. doi:10.1002/047084289X.rm013.pub2 Article Online Posting Date: March 14, 2008
  2. Pryor WA, Stanley JP (1975). "Letter: A suggested mechanism for the production of malonaldehyde during the autoxidation of polyunsaturated fatty acids. Nonenzymatic production of prostaglandin endoperoxides during autoxidation". J. Org. Chem. 40 (24): 3615–7. doi:10.1021/jo00912a038. PMID 1185332.
  3. Farmer EE, Davoine C (2007). "Reactive electrophile species". Curr. Opin. Plant Biol. 10 (4): 380–6. doi:10.1016/j.pbi.2007.04.019. PMID 17646124.
  4. Moore K, Roberts LJ (1998). "Measurement of lipid peroxidation". Free Radic. Res. 28 (6): 659–71. doi:10.3109/10715769809065821. PMID 9736317.
  5. Del Rio D, Stewart AJ, Pellegrini N (2005). "A review of recent studies on malonaldehyde as toxic molecule and biological marker of oxidative stress". Nutr Metab Cardiovasc Dis. 15 (4): 316–28. doi:10.1016/j.numecd.2005.05.003. PMID 16054557.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. Marnett LJ (1999). "Lipid peroxidation-DNA damage by malondialdehyde". Mutat. Res. 424 (1–2): 83–95. doi:10.1016/S0027-5107(99)00010-X. PMID 10064852.
  7. http://www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33
  8. Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ (2002). "Evidence of oxidative stress in human corneal diseases". J. Histochem. Cytochem. 50 (3): 341–51. PMID 11850437. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  9. Tiku ML, Narla H, Jain M, Yalamanchili P (2007). "Glucosamine prevents in vitro collagen degradation in chondrocytes by inhibiting advanced lipoxidation reactions and protein oxidation". Arthritis Res. Ther. 9 (4): R76. doi:10.1186/ar2274. PMC 2206377. PMID 17686167.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)


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