| Malondialdehyde |
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| Identifiers |
| Abbreviations |
MDA |
| CAS number |
542-78-9 Y |
| PubChem |
10964 |
| ChemSpider |
10499 N |
| KEGG |
C19440 Y |
| Jmol-3D images |
Image 1 |
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InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2 N
Key: WSMYVTOQOOLQHP-UHFFFAOYSA-N N
InChI=1/C3H4O2/c4-2-1-3-5/h2-3H,1H2
Key: WSMYVTOQOOLQHP-UHFFFAOYAU
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| 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
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| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| N (verify) (what is: Y/N?) |
| Infobox references |
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Malondialdehyde (MDA) 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.
Contents
- 1 Structure and synthesis
- 2 Biochemistry
- 3 Hazards and pathology
- 4 See also
- 5 References
Structure and synthesis
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 results from lipid peroxidation of polyunsaturated fatty acids.[3] The degree of lipid peroxidation can be estimated by the amount of malondialdehyde in tissues.[3]
Biochemistry
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
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
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
- Methylglyoxal
- 4-Hydroxynonenal
References
- ^ CDC - NIOSH Pocket Guide to Chemical Hazards
- ^ 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
- ^ a b 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. PMID 16289006.
- ^ 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.
- ^ 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.
- ^ Moore K, Roberts LJ (1998). "Measurement of lipid peroxidation". Free Radic. Res. 28 (6): 659–71. doi:10.3109/10715769809065821. PMID 9736317.
- ^ 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.
- ^ 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.
- ^ http://www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33[dead link]
- ^ Hartman PE, Putative mutagens and carcinogens in foods. IV. Malonaldehyde (malondialdehyde) Environ Mutagen. 1983;5(4):603-7
- ^ 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
- ^ 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.
- ^ 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.
