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Malondialdehyde

Malondialdehyde

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Names IUPAC name propanedial Other names

Malonic aldehyde; Malonodialdehyde; Propanedial; 1,3-Propanedial ; Malonaldehyde ; Malonyldialdehyde

Identifiers CAS Number 542-78-9 3D model (JSmol)

dialdehyde: Interactive image

enol: Interactive image

Abbreviations MDA ChemSpider 10499 KEGG C19440 PubChem CID 10964 UNII 4Y8F71G49Q

CompTox Dashboard (EPA)

DTXSID90202556 InChI SMILES Properties

Chemical formula 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

4-Hydroxynonenal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

verify (what is  ?) Infobox references

Malondialdehyde (MDA) is the organic compound with the nominal formula CH2(CHO)2. A colorless liquid, malondialdehyde is a highly reactive compound that occurs as the enol.[2] It occurs naturally and is a marker for oxidative stress.

Contents

1 Structure and synthesis

2 Biosynthesis and reactivity

2.1 Analysis

3 Hazards and pathology

4 See also 5 References

Structure and synthesis[edit]

Malondialdehyde mainly exists as the enol:[2]

CH2(CHO)2 → HOC(H)=CH-CHO

In organic solvents, the -isomer is favored, whereas in water the -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).

Biosynthesis and reactivity[edit]

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.[4][5] 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).[6] The degree of lipid peroxidation can be estimated by the amount of malondialdehyde in tissues.[3]

Reactive oxygen species degrade polyunsaturated lipids, forming malondialdehyde.[7] 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).[8] The production of this aldehyde is used as a biomarker to measure the level of oxidative stress in an organism.[9][10]

Malondialdehyde reacts with deoxyadenosine and deoxyguanosine in DNA, forming DNA adducts, the primary one being M1G, which is mutagenic.[11] The guanidine group of arginine residues condense with malondialdehyde to give 2-aminopyrimidines.

Human ALDH1A1 aldehyde dehydrogenase is capable of oxidizing malondialdehyde.

Analysis[edit]

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][12] 1-Methyl-2-phenylindole is an alternative more selective reagent.[2]

Hazards and pathology[edit]

Malondialdehyde is reactive and potentially mutagenic.[13] It has been found in heated edible oils such as sunflower and palm oils.[14]

Corneas of patients with keratoconus and bullous keratopathy have increased levels of malondialdehyde, according to one study.[15] MDA also can be found in tissue sections of joints from patients with osteoarthritis.[16]

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.[17]

See also[edit]

Methylglyoxal 4-Hydroxynonenal Isoprostane

References[edit]

^ NIOSH Pocket Guide to Chemical Hazards. "#0377". National Institute for Occupational Safety and Health (NIOSH).

^ V. Nair, C. L. O'Neil, P. G. Wang "Malondialdehyde", , 2008, John Wiley & Sons, New York. doi:10.1002/047084289X.rm013.pub2 Article Online Posting Date: March 14, 2008

^ Davey MW1, Stals E, Panis B, Keulemans J, Swennen RL (2005). "High-throughput determination of malondialdehyde in plant tissues". . 347 (2): 201–207. doi:10.1016/j.ab.2005.09.041. PMID 16289006.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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منبع مطلب : en.wikipedia.org

[Malondialdehyde (MDA) as a lipid peroxidation marker]

Free radicals generate the lipid peroxidation process in an organism. Malondialdehyde (MDA) is one of the final products of polyunsaturated fatty acids peroxidation in the cells. An increase in free radicals causes overproduction of MDA. Malondialdehyde level is commonly known as a marker of oxidati …

Review

. 2004;57(9-10):453-5.

[Malondialdehyde (MDA) as a lipid peroxidation marker]

[Article in Polish]

Stefan Gaweł  1 , Maria Wardas, Elzbieta Niedworok, Piotr Wardas

Affiliations

Affiliation

1 Oddziału Schorzeń Układu Oddechowego Szpitala nr 2 im. dr. Karola Zahorskiego w Sosnowcu.

PMID: 15765761 Review

[Malondialdehyde (MDA) as a lipid peroxidation marker]

[Article in Polish]

Stefan Gaweł et al. Wiad Lek. 2004.

. 2004;57(9-10):453-5.

Authors

Stefan Gaweł  1 , Maria Wardas, Elzbieta Niedworok, Piotr Wardas

Affiliation

1 Oddziału Schorzeń Układu Oddechowego Szpitala nr 2 im. dr. Karola Zahorskiego w Sosnowcu.

PMID: 15765761

Abstract

Free radicals generate the lipid peroxidation process in an organism. Malondialdehyde (MDA) is one of the final products of polyunsaturated fatty acids peroxidation in the cells. An increase in free radicals causes overproduction of MDA. Malondialdehyde level is commonly known as a marker of oxidative stress and the antioxidant status in cancerous patients.

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Kowalczuk K, et al. Ann Univ Mariae Curie Sklodowska Med. 2002. PMID: 12898834

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