| |||
Names | |||
---|---|---|---|
IUPAC name
propanedial
| |||
Other names
Malonic aldehyde; Malonodialdehyde; Propanedial; 1,3-Propanedial ; Malonaldehyde ; Malonyldialdehyde
| |||
Identifiers | |||
3D model (
JSmol)
|
| ||
Abbreviations | MDA | ||
ChemSpider | |||
KEGG | |||
PubChem
CID
|
|||
UNII | |||
CompTox Dashboard (
EPA)
|
|||
| |||
| |||
Properties | |||
C3H4O2 | |||
Molar mass | 72.063 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) | ||
Hazards | |||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
|
none [1] | ||
REL (Recommended)
|
Ca [1] | ||
IDLH (Immediate danger)
|
Ca [N.D.] [1] | ||
Related compounds | |||
Related alkenals
|
Glucic acid | ||
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Malondialdehyde belong to the class of β-dicarbonyls. A colorless liquid, malondialdehyde is a highly reactive compound that occurs as the enol. [2] It is a physiological metabolite, and a marker for oxidative stress.
Malondialdehyde mainly exists as its enol, hydroxyacrolein: [2]
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. [2] Malondialdehyde 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] 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). [4] The degree of lipid peroxidation can be estimated by the amount of malondialdehyde in tissues. [3]
Reactive oxygen species degrade polyunsaturated lipids, forming malondialdehyde. [5] 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). [6] The production of this aldehyde is used as a biomarker to measure the level of oxidative stress in an organism. [7] [8]
Malondialdehyde reacts with deoxyadenosine and deoxyguanosine in DNA, forming DNA adducts, the primary one being M1G, which is mutagenic. [9] 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. [2] [10] 1-Methyl-2-phenylindole is an alternative more selective reagent. [2]
Malondialdehyde is reactive and potentially mutagenic. [11] It has been found in heated edible oils such as sunflower and palm oils. [12]
Corneas of patients with keratoconus and bullous keratopathy have increased levels of malondialdehyde, according to one study. [13] MDA also can be found in tissue sections of joints from patients with osteoarthritis. [14]
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. [15]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link) CS1 maint: numeric names: authors list (
link)