1.0 2010-04-08 22:07:56 UTC 2018-05-28 23:16:48 UTC FDB008116 1,3-Propanedial It is used as an indicator of fatty acid and lipid peroxidation, and oxidative changes in foods MDA 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.; Malondialdehyde (MDA) is the dialdehyde of malonic acid and a biomarker of oxidative damage to lipids caused by smoking.; Oxidized lipids are able to produce MDA as a decomposition product. The mechanism is thought to involve formation of prostaglandin-like endoperoxides from polyunsaturated fatty acids with two or more double bonds. An alternative mechanism is based on successive hydroperoxide formation and β-cleavage of polyunsaturated fatty acids. MDA is then directly formed by β-scission of a 3-hydroperoxyaldehyde or by reaction between acrolein and hydroxyl radicals. While oxidation of polyunsaturated fatty acids is the major source of MDA in vivo, other minor sources exists such as byproducts of free radical generation by ionizing radiation and of the biosynthesis of prostaglandins. Aldehydes are generally reactive species capable of forming adducts and complexes in biological systems and MDA is no exception although the main species at physiological pH is the enolate ion which is of relative low reactivity. Consistent evidence is available for the reaction between MDA and cellular macromolecules such as proteins, RNA and DNA. MDA reacts with DNA to form adducts to deoxyguanosine and deoxyadenosine which may be mutagenic and these can be quantified in several human tissues. Oxidative stress is an imbalance between oxidants and antioxidants on a cellular or individual level. Oxidative damage is one result of such an imbalance and includes oxidative modification of cellular macromolecules, induction of cell death by apoptosis or necrosis, as well as structural tissue damage. Chemically speaking, oxidants are compounds capable of oxidizing target molecules. This can take place in three ways: abstraction of hydrogen, abstraction of electrons or addition of oxygen. All cells living under aerobic conditions are continuously exposed to a large numbers of oxidants derived from various endogenous and exogenous sources. The endogenous sources of oxidants are several and include the respiratory chain in the mitochondria, immune reactions, enzymes such as xanthine oxidase and nitric oxide synthase and transition metal mediated oxidation. Various exogenous sources of ROS also contribute directly or indirectly to the total oxidant load. These include effects of ionizing and non-ionizing radiation, air pollution and natural toxic gases such as ozone, and chemicals and toxins including oxidizing disinfectants. A poor diet containing inadequate amounts of nutrients may also indirectly result in oxidative stress by impairing cellular defense mechanisms. The cellular macromolecules, in particular lipids, proteins and DNA, are natural targets of oxidation. Oxidants are capable of initiating lipid oxidation by abstraction of an allylic proton from a polyunsaturated fatty acid. This process, by multiple stages leading to the formation of lipid hydroperoxides, is a known contributor to the development of atherosclerosis. (PMID: 17336279); 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).; 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.; 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 which are 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. 1,3-Propanedialdehyde 1,3-Propanedione Malonaldehyde Malonaldehyde, 8CI Malondialdehyde Malondialdehyde, sodium Malonic aldehyde Malonic dialdehyde Malonodialdehyde Malonylaldehyde Malonyldialdehyde MDA MDD Propanedial Sodium malondialdehyde C3H4O2 72.0627 72.021129372 propanedial malonaldehyde 542-78-9 O=CCC=O InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2 WSMYVTOQOOLQHP-UHFFFAOYSA-N belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group. 1,3-dicarbonyl compounds Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Alpha-hydrogen aldehydes Hydrocarbon derivatives Organic oxides Short-chain aldehydes 1,3-dicarbonyl compound Aldehyde Aliphatic acyclic compound Alpha-hydrogen aldehyde Hydrocarbon derivative Organic oxide Short-chain aldehyde dialdehyde Solid logp 0.10 ALOGPS logs 0.52 ALOGPS solubility 2.41e+02 g/l ALOGPS melting_point Mp 72-74° logp -0.65 ChemAxon pka_strongest_acidic 6.68 ChemAxon pka_strongest_basic -6.8 ChemAxon iupac propanedial ChemAxon average_mass 72.0627 ChemAxon mono_mass 72.021129372 ChemAxon smiles O=CCC=O ChemAxon formula C3H4O2 ChemAxon inchi InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2 ChemAxon inchikey WSMYVTOQOOLQHP-UHFFFAOYSA-N ChemAxon polar_surface_area 34.14 ChemAxon refractivity 17.14 ChemAxon polarizability 6.42 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18991 Specdb::CMs 154812 Specdb::MsIr 2367 Specdb::MsIr 2368 Specdb::NmrOneD 67712 Specdb::NmrOneD 67713 Specdb::NmrOneD 67714 Specdb::NmrOneD 67715 Specdb::NmrOneD 67716 Specdb::NmrOneD 67717 Specdb::NmrOneD 67718 Specdb::NmrOneD 67719 Specdb::NmrOneD 67720 Specdb::NmrOneD 67721 Specdb::NmrOneD 67722 Specdb::NmrOneD 67723 Specdb::NmrOneD 67724 Specdb::NmrOneD 67725 Specdb::NmrOneD 67726 Specdb::NmrOneD 67727 Specdb::NmrOneD 67728 Specdb::NmrOneD 67729 Specdb::NmrOneD 67730 Specdb::NmrOneD 67731 Specdb::MsMs 81465 Specdb::MsMs 81466 Specdb::MsMs 81467 Specdb::MsMs 142581 Specdb::MsMs 142582 Specdb::MsMs 142583 Specdb::MsMs 2804046 Specdb::MsMs 2804047 Specdb::MsMs 2804048 Specdb::MsMs 2875313 Specdb::MsMs 2875314 Specdb::MsMs 2875315 HMDB06112 MDD #<Reference:0x00005612733a7a10> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823