Malondialdehyde

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Malondialdehyde
Malondialdehyde.png
Identifiers
Abbreviations MDA
CAS number 542-78-9 YesY
PubChem 10964
ChemSpider 10499 N
KEGG C19440 YesY
Jmol-3D images Image 1
Properties
Molecular formula C3H4O2
Molar mass 72.06 g mol−1
Appearance Needle-like solid[1]
Density 0.991 g/mL
Melting point 72 °C (162 °F; 345 K)
Boiling point 108 °C (226 °F; 381 K)
Related compounds
Related alkenals Glucic acid

4-Hydroxynonenal

Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Malondialdehyde 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[edit]

Malondialdehyde mainly exists in the enol form:[2]

CH2(CHO)2 → HOCH=CH-CHO

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

Malondialdehyde 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.[2] It is easily deprotonated to give the sodium salt of the enolate (m.p. 245 °C).

Malondialdehyde is generated from reactive oxygen species (ROS), and as such is assayed in vivo as a bio-marker of oxidative stress.[3]

Biochemistry[edit]

Reactive oxygen species degrade polyunsaturated lipids, forming malondialdehyde.[4] 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).[5] The production of this aldehyde is used as a biomarker to measure the level of oxidative stress in an organism.[6][7]

Malondialdehyde reacts with deoxyadenosine and deoxyguanosine in DNA, forming DNA adducts, the primary one being M1G, which is mutagenic.[8] The guanidine group of arginine residues condense with malondialdehyde to give 2-aminopyrimidines.

Human ALDH1A1 aldehyde dehydrogenase is capable of oxidizing malondialdehyde.

Analysis[edit]

Malondialdehyde and other thiobarbituric reactive substances (TBARS) condense with two equivalents of thiobarbituric acid to give a fluorescent red derivative that can be assayed spectrophotometrically.[2][9] 1-Methyl-2-phenylindole is an alternative more selective reagent.[2]

Hazards and pathology[edit]

Malondialdehyde is reactive and potentially mutagenic.[10] It has been found in heated edible oils such as sunflower and palm oils.[11]

Corneas of patients suffering from keratoconus and bullous keratopathy have increased levels of malondialdehyde, according to one study.[12] MDA also can be found in tissue sections of joints from patients with osteoarthritis.[13]

See also[edit]

References[edit]

  1. ^ CDC - NIOSH Pocket Guide to Chemical Hazards
  2. ^ a b c d 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
  3. ^ Am J Clin Nutr 94: 422–430. 2011. 
  4. ^ Pryor WA, Stanley JP (1975). "Letter: A suggested mechanism for the production of malondialdehyde 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. 
  5. ^ 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. 
  6. ^ Moore K, Roberts LJ (1998). "Measurement of lipid peroxidation". Free Radic. Res. 28 (6): 659–71. doi:10.3109/10715769809065821. PMID 9736317. 
  7. ^ Del Rio D, Stewart AJ, Pellegrini N (2005). "A review of recent studies on malondialdehyde 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. 
  8. ^ 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. 
  9. ^ http://www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33[dead link]
  10. ^ Hartman PE, Putative mutagens and carcinogens in foods. IV. Malonaldehyde (malondialdehyde) Environ Mutagen. 1983;5(4):603-7
  11. ^ Dourerdjou, P.; Koner, B. C. (2008), Effect of Different Cooking Vessels on Heat-Induced Lipid Peroxidation of Different Edible Oils" Journal of Food Biochemistry, 32: 740–751. doi: 10.1111/j.1745-4514.2008.00195.x
  12. ^ Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ (March 2002). "Evidence of oxidative stress in human corneal diseases". J. Histochem. Cytochem. 50 (3): 341–51. doi:10.1177/002215540205000306. PMID 11850437. 
  13. ^ 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.