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Malondialdehyde

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Malondialdehyde
Names
IUPAC name propanedial
Other names Malonic aldehyde; Malonodialdehyde; Propanedial; 1,3-Propanedial ; Malonaldehyde ; Malonyldialdehyde
Identifiers
CAS Number
3D model (JSmol)
Abbreviations MDA
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2Key: WSMYVTOQOOLQHP-UHFFFAOYSA-N
  • InChI=1/C3H4O2/c4-2-1-3-5/h2-3H,1H2Key: WSMYVTOQOOLQHP-UHFFFAOYAU
SMILES
  • dialdehyde: O=CCC=O
  • enol: OC=CC=O
Properties
Chemical formula C3H4O2
Molar mass 72.063 g·mol
Appearance Needle-like solid
Density 0.991 g/mL
Melting point 72 °C (162 °F; 345 K)
Boiling point 108 °C (226 °F; 381 K)
Hazards
NIOSH (US health exposure limits):
PEL (Permissible) none
REL (Recommended) Ca
IDLH (Immediate danger) Ca
Related compounds
Related alkenals Glucic acid

4-Hydroxynonenal

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

Malondialdehyde belong to the class of β-dicarbonyls. A colorless liquid, malondialdehyde is a highly reactive compound that occurs as the enol. It is a physiological metabolite, and a marker for oxidative stress.

Structure and synthesis

Malondialdehyde mainly exists as its enol, hydroxyacrolein:

CH2(CHO)2 → HOC(H)=CH-CHO

In organic solvents, the cis-isomer is favored, whereas in water the trans-isomer predominates. The equilibrium is rapid and is inconsequential for many purposes.

In the laboratory it can be generated in situ by hydrolysis of its acetal 1,1,3,3-tetramethoxypropane, which is commercially available and shelf-stable, unlike malondialdehyde. Malondialdehyde is easily deprotonated to give the sodium salt of the enolate (m.p. 245 °C).

Biosynthesis and reactivity

Malondialdehyde results from lipid peroxidation of polyunsaturated fatty acids. It is a prominent product in thromboxane A2 synthesis wherein cyclooxygenase 1 or cycloxygenase 2 metabolizes arachidonic acid to prostaglandin H2 by platelets and a wide array of other cell types and tissues. This product is further metabolized by thromboxane synthase to thromboxane A2, 12-hydroxyheptadecatrienoic acid, and malonyldialdehyde. Alternatively, it may rearrange non-enzymatically to a mixture of 8-cis and 8-trans isomers of 12-hydroxyeicosaheptaenoic acid plus malonyldialdehyde (see 12-Hydroxyheptadecatrienoic acid). The degree of lipid peroxidation can be estimated by the amount of malondialdehyde in tissues.

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.

Malondialdehyde 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 malondialdehyde to give 2-aminopyrimidines.

Human ALDH1A1 aldehyde dehydrogenase is capable of oxidizing malondialdehyde.

Analysis

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. 1-Methyl-2-phenylindole is an alternative more selective reagent.

Hazards and pathology

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

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

Levels of malondialdehyde can be also considered (as a marker of lipid peroxidation) to assess the membrane damage in spermatozoa; this is crucial because oxidative stress affects sperm function by altering membrane fluidity, permeability and impairing sperm functional competence.

See also

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0377". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ 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. ^ Davey MW1, Stals E, Panis B, Keulemans J, Swennen RL (2005). "High-Throughput Determination of Malondialdehyde in Plant Tissues". Analytical Biochemistry. 347 (2): 201–207. doi:10.1016/j.ab.2005.09.041. PMID 16289006.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  4. Rouzer, Carol A.; Marnett, Lawrence J. (2003). "Mechanism of Free Radical Oxygenation of Polyunsaturated Fatty Acids by Cyclooxygenases". Chemical Reviews. 103 (6): 2239–2304. doi:10.1021/cr000068x. PMID 12797830.
  5. 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.
  6. Farmer EE, Davoine C (2007). "Reactive electrophile species". Curr. Opin. Plant Biol. 10 (4): 380–6. Bibcode:2007COPB...10..380F. doi:10.1016/j.pbi.2007.04.019. PMID 17646124.
  7. Moore K, Roberts LJ (1998). "Measurement of lipid peroxidation". Free Radic. Res. 28 (6): 659–71. doi:10.3109/10715769809065821. PMID 9736317.
  8. 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.
  9. Marnett LJ (1999). "Lipid peroxidation-DNA damage by malondialdehyde". Mutat. Res. 424 (1–2): 83–95. Bibcode:1999MRFMM.424...83M. doi:10.1016/S0027-5107(99)00010-X. PMID 10064852.
  10. "Thiobarbituric acid reactive substances (TBARS) Assay". www.amdcc.org. Archived from the original on 14 September 2006.
  11. Hartman PE, Putative mutagens and carcinogens in foods. IV. Malonaldehyde (malondialdehyde) Environ Mutagen. 1983;5(4):603-7
  12. 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
  13. 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.
  14. 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 Research & Therapy. 9 (4): R76. doi:10.1186/ar2274. PMC 2206377. PMID 17686167.
  15. Collodel, G.; Moretti, E.; Micheli, L.; Menchiari, A.; Moltoni, L.; Cerretani, D. (March 2015). "Semen characteristics and malondialdehyde levels in men with different reproductive problems". Andrology. 3 (2): 280–286. doi:10.1111/andr.297. PMID 25331426. S2CID 28027300.
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