|Jmol-3D images||Image 1|
|Molar mass||72.06 g mol−1|
|Melting point||72 °C (162 °F; 345 K)|
|Boiling point||108 °C (226 °F; 381 K)|
|Related alkenals||Glucic acid
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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
- 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. It is easily deprotonated to give the sodium salt of the enolate (m.p. 245 °C).
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.
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
Corneas of patients suffering from 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.
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