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{{Use dmy dates|date=September 2023}}{{chembox| Verifiedfields = changed| Watchedfields = changed| verifiedrevid = 435630162| Name = Malondialdehyde| ImageFile = Malondialdehyd.svg| ImageFileL1 = Malondialdehyde Enol-Form.png| ImageSizeL1 = 150| ImageFileR1 = Malondialdehyde Keto-Form.png| ImageSizeR1 = 150| IUPACName = propanedial| OtherNames = Malonic aldehyde; Malonodialdehyde; Propanedial; 1,3-Propanedial ; Malonaldehyde ; Malonyldialdehyde|Section1={{Chembox Identifiers| Abbreviations = MDA

correct|CAS}}| CASNo = 542-78-9

correct|FDA}}| UNII = 4Y8F71G49Q| PubChem = 10964

correct|kegg}}| KEGG = C19440| SMILES = O=CCC=O| SMILES_Comment = dialdehyde| SMILES1 = OC=CC=O| SMILES1_Comment = enol

changed|chemspider}}| ChemSpiderID = 10499| InChI = 1/C3H4O2/c4-2-1-3-5/h2-3H,1H2| InChIKey = WSMYVTOQOOLQHP-UHFFFAOYAU

changed|chemspider}}| StdInChI = 1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2

changed|chemspider}}| StdInChIKey = WSMYVTOQOOLQHP-UHFFFAOYSA-N }}|Section2={{Chembox Properties

H=4 | O=2| MeltingPtC = 72| Density = 0.991 g/mL| BoilingPtC = 108

0377}} }}|Section3={{Chembox Hazards| IDLH = Ca [N.D.]| REL = Ca| PEL = none }}|Section4={{Chembox Related| OtherFunction_label = alkenals| OtherFunction = Glucic acid4-Hydroxynonenal}}}}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: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 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 Â°C). Biosynthesis and reactivity Malondialdehyde results from lipid peroxidation of polyunsaturated fatty acids.JOURNAL, Davey MW1, Stals E, Panis B, Keulemans J, Swennen RL, High-Throughput Determination of Malondialdehyde in Plant Tissues, Analytical Biochemistry, 347, 2, 2005, 201–207, 10.1016/j.ab.2005.09.041, 16289006, 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).JOURNAL, 10.1021/cr000068x, Mechanism of Free Radical Oxygenation of Polyunsaturated Fatty Acids by Cyclooxygenases, 2003, Rouzer, Carol A., Marnett, Lawrence J., Chemical Reviews, 103, 6, 2239–2304, 12797830, The degree of lipid peroxidation can be estimated by the amount of malondialdehyde in tissues.Reactive oxygen species degrade polyunsaturated lipids, forming malondialdehyde.JOURNAL, Pryor WA, Stanley JP, 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, 1975, 1185332, 10.1021/jo00912a038, 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).JOURNAL, Farmer EE, Davoine C, Reactive electrophile species, Curr. Opin. Plant Biol., 10, 4, 380–6, 2007, 17646124, 10.1016/j.pbi.2007.04.019, The production of this aldehyde is used as a biomarker to measure the level of oxidative stress in an organism.JOURNAL, Moore K, Roberts LJ, Measurement of lipid peroxidation, Free Radic. Res., 28, 6, 659–71, 1998, 9736317, 10.3109/10715769809065821, JOURNAL, Del Rio D, Stewart AJ, Pellegrini N, A review of recent studies on malondialdehyde as toxic molecule and biological marker of oxidative stress, Nutr Metab Cardiovasc Dis, 15, 4, 316–28, 2005, 16054557, 10.1016/j.numecd.2005.05.003, Malondialdehyde reacts with deoxyadenosine and deoxyguanosine in DNA, forming DNA adducts, the primary one being M1G, which is mutagenic.JOURNAL, Marnett LJ, Lipid peroxidation-DNA damage by malondialdehyde, Mutat. Res., 424, 1–2, 83–95, 1999, 10064852, 10.1016/S0027-5107(99)00010-X, 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.WEB,www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33, Thiobarbituric acid reactive substances (TBARS) Assay, www.amdcc.org,www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33," title="web.archive.org/web/20060914082200www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33,">web.archive.org/web/20060914082200www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33, September 14, 2006, 1-Methyl-2-phenylindole is an alternative more selective reagent. Hazards and pathology Malondialdehyde is reactive and potentially mutagenic.Hartman PE, Putative mutagens and carcinogens in foods. IV. Malonaldehyde (malondialdehyde) Environ Mutagen. 1983;5(4):603-7 It has been found in heated edible oils such as sunflower and palm oils.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}}Corneas of patients with keratoconus and bullous keratopathy have increased levels of malondialdehyde, according to one study.JOURNAL, Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ, Evidence of oxidative stress in human corneal diseases, J. Histochem. Cytochem., 50, 3, 341–51, March 2002, 11850437, 10.1177/002215540205000306, free, MDA also can be found in tissue sections of joints from patients with osteoarthritis.JOURNAL, Tiku ML, Narla H, Jain M, Yalamanchili P, Glucosamine prevents in vitro collagen degradation in chondrocytes by inhibiting advanced lipoxidation reactions and protein oxidation, Arthritis Research & Therapy, 9, 4, R76, 2007, 17686167, 2206377, 10.1186/ar2274, free, 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.JOURNAL, 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, en, 3, 2, 280–286, 10.1111/andr.297, 25331426, 28027300, free, See also Methylglyoxal 4-Hydroxynonenal Isoprostane References {{reflist}}