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			{{Use dmy dates|date=September 2023}}
	{{chembox		{{chembox
	| Verifiedfields = changed		| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 410007008		| verifiedrevid = 435630162
	| Name = Malondialdehyde		| Name = Malondialdehyde
	| ImageFile = Malondialdehyde.png		| ImageFile = Malondialdehyd.svg
			| ImageFileL1 = Malondialdehyde Enol-Form.png
⚫	| IUPACName = propanedial
			| ImageSizeL1 = 150
⚫	| Section1 = {{Chembox Identifiers
			| ImageFileR1 = Malondialdehyde Keto-Form.png
⚫	| CASNo = 542-78-9
			| ImageSizeR1 = 150
		⚫	| IUPACName = propanedial
			| OtherNames = Malonic aldehyde; Malonodialdehyde; Propanedial; 1,3-Propanedial ; Malonaldehyde ; Malonyldialdehyde
		⚫	|Section1={{Chembox Identifiers
			| Abbreviations = MDA
			| CASNo_Ref = {{cascite|correct|CAS}}
		⚫	| CASNo = 542-78-9
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 4Y8F71G49Q
	| PubChem = 10964		| PubChem = 10964
	| KEGG_Ref = {{keggcite|changed|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C19440		| KEGG = C19440
	| SMILES = C(C=O)C=O		| SMILES = O=CCC=O
			| SMILES_Comment = dialdehyde
⚫	}}
			| SMILES1 = OC=CC=O
⚫	| Section2 = {{Chembox Properties
			| SMILES1_Comment = enol
	| Formula = C<sub>3</sub>H<sub>4</sub>O<sub>2</sub>
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
	| MolarMass = 72.0636 g/mol
	| MeltingPtC = 72		| ChemSpiderID = 10499
			| InChI = 1/C3H4O2/c4-2-1-3-5/h2-3H,1H2
	| Density =
			| InChIKey = WSMYVTOQOOLQHP-UHFFFAOYAU
⚫	}}
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫	| Section3 = {{Chembox Related
			| StdInChI = 1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2
⚫	| Function = alkenals
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫	| OtherFunctn = ]<br />
			| StdInChIKey = WSMYVTOQOOLQHP-UHFFFAOYSA-N
		⚫	}}
		⚫	|Section2={{Chembox Properties
			| C=3 | H=4 | O=2
			| MeltingPtC = 72
			| Density = 0.991 g/mL
			| BoilingPtC = 108
			| Appearance = Needle-like solid<ref name=PGCH>{{PGCH|0377}}</ref>
		⚫	}}
		⚫	|Section3={{Chembox Hazards
			| IDLH = Ca <ref name=PGCH/>
			| REL = Ca<ref name=PGCH/>
			| PEL = none<ref name=PGCH/>
			}}
			|Section4={{Chembox Related
		⚫	| OtherFunction_label = alkenals
		⚫	| OtherFunction = ]<br />
	]		]
	}}		}}
	}}		}}
	'''Malonaldehyde''' is the ] with the ] CH<sub>2</sub>(CHO)<sub>2</sub>. The structure of this species is more complex than this formula suggests. This reactive species occurs naturally and is a marker for ].		'''Malondialdehyde''' belong to the class of β-dicarbonyls. A colorless liquid, malondialdehyde is a highly reactive compound that occurs as the ].<ref name="eEROS"/> It is a physiological metabolite, and a marker for ].
	== Structure and synthesis ==		== Structure and synthesis ==
	Malonaldehyde mainly exists in the ] form:<ref name="eEROS">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</ref>		Malondialdehyde mainly exists as its ], hydroxyacrolein:<ref name="eEROS">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</ref>
⚫	:CH<sub>2</sub>(CHO)<sub>2</sub> → HOCH=CH-CHO
⚫	In organic solvents, the cis isomer is favored, whereas in water the trans isomer predominates.
		⚫	:CH<sub>2</sub>(CHO)<sub>2</sub> → HOC(H)=CH-CHO
⚫	Malonaldehyde 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.<ref name=eEROS/> It is easily deprotonated to give the sodium salt of the enolate (m.p.&nbsp;245 °C).
		⚫	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 ], which is commercially available and shelf-stable, unlike malondialdehyde.<ref name=eEROS/> Malondialdehyde is easily deprotonated to give the sodium salt of the enolate (m.p.&nbsp;245&nbsp;°C).
	== Biochemistry ==
⚫	] degrade ], forming malondialdehyde.<ref>{{cite journal |author=Pryor WA, Stanley JP |title=Letter: A suggested mechanism for the production of malonaldehyde during the autoxidation of polyunsaturated fatty acids. Nonenzymatic production of prostaglandin endoperoxides during autoxidation |journal=J. Org. Chem. |volume=40 |issue=24 |pages=3615–7 |year=1975 |pmid=1185332 |doi=10.1021/jo00912a038}}</ref> This compound is a reactive ] and is one of the many ''reactive electrophile species'' that cause toxic stress in cells and form covalent protein adducts referred to as ] (ALE), in analogy to ] (AGE).<ref>{{cite journal |author=Farmer EE, Davoine C |title=Reactive electrophile species |journal=Curr. Opin. Plant Biol. |volume=10 |issue=4 |pages=380–6 |year=2007 |pmid=17646124 |doi=10.1016/j.pbi.2007.04.019}}</ref> The production of this aldehyde is used as a biomarker to measure the level of ] in an organism.<ref>{{cite journal |author=Moore K, Roberts LJ |title=Measurement of lipid peroxidation |journal=Free Radic. Res. |volume=28 |issue=6 |pages=659–71 |year=1998 |pmid=9736317 |doi=10.3109/10715769809065821}}</ref><ref>{{cite journal |author=Del Rio D, Stewart AJ, Pellegrini N |title=A review of recent studies on malonaldehyde as toxic molecule and biological marker of oxidative stress |journal=Nutr Metab Cardiovasc Dis |volume=15 |issue=4 |pages=316–28 |year=2005 |pmid=16054557 |doi=10.1016/j.numecd.2005.05.003}}</ref>
			==Biosynthesis and reactivity==
⚫	Malonaldehyde reacts with ] and ] in DNA, forming ], the primary one being ], which is ].<ref name=martnett>{{cite journal |author=Marnett LJ |title=Lipid peroxidation-DNA damage by malondialdehyde |journal=Mutat. Res. |volume=424 |issue=1-2 |pages=83–95 |year=1999 |pmid=10064852 |doi=10.1016/S0027-5107(99)00010-X}}</ref> The guanidine group of arginine residues condense with MDA to give 2-aminopyrimidines.
			Malondialdehyde results from ] of ].<ref name="pmid16289006">{{cite journal | author=Davey MW1, Stals E, Panis B, Keulemans J, Swennen RL | title=High-Throughput Determination of Malondialdehyde in Plant Tissues | journal=] | volume=347 | issue=2 | year=2005 | pages=201–207 | doi=10.1016/j.ab.2005.09.041 | pmid=16289006}}</ref> It is a prominent product in ] synthesis wherein ] or cycloxygenase 2 metabolizes ] to ] by ] and a wide array of other cell types and tissues. This product is further metabolized by ] to ], ], 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 ]).<ref name=Marnett>{{cite journal |doi=10.1021/cr000068x |title=Mechanism of Free Radical Oxygenation of Polyunsaturated Fatty Acids by Cyclooxygenases |date=2003 |last1=Rouzer |first1=Carol A. |last2=Marnett |first2=Lawrence J. |journal=Chemical Reviews |volume=103 |issue=6 |pages=2239–2304 |pmid=12797830 }}</ref> The degree of lipid peroxidation can be estimated by the amount of malondialdehyde in tissues.<ref name="pmid16289006" />
		⚫	] degrade ], forming malondialdehyde.<ref>{{cite journal |vauthors=Pryor WA, Stanley JP |title=Letter: A suggested mechanism for the production of malondialdehyde during the autoxidation of polyunsaturated fatty acids. Nonenzymatic production of prostaglandin endoperoxides during autoxidation |journal=J. Org. Chem. |volume=40 |issue=24 |pages=3615–7 |year=1975 |pmid=1185332 |doi=10.1021/jo00912a038}}</ref> This compound is a reactive ] 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 ] (AGE).<ref>{{cite journal |vauthors=Farmer EE, Davoine C |title=Reactive electrophile species |journal=Curr. Opin. Plant Biol. |volume=10 |issue=4 |pages=380–6 |year=2007 |pmid=17646124 |doi=10.1016/j.pbi.2007.04.019|bibcode=2007COPB...10..380F }}</ref> The production of this aldehyde is used as a biomarker to measure the level of ] in an organism.<ref>{{cite journal |vauthors=Moore K, Roberts LJ |title=Measurement of lipid peroxidation |journal=Free Radic. Res. |volume=28 |issue=6 |pages=659–71 |year=1998 |pmid=9736317 |doi=10.3109/10715769809065821}}</ref><ref>{{cite journal |vauthors=Del Rio D, Stewart AJ, Pellegrini N |title=A review of recent studies on malondialdehyde as toxic molecule and biological marker of oxidative stress |journal=Nutr Metab Cardiovasc Dis |volume=15 |issue=4 |pages=316–28 |year=2005 |pmid=16054557 |doi=10.1016/j.numecd.2005.05.003}}</ref>
⚫	Human ] aldehyde dehydrogenase is capable of oxidising malonaldehyde.
		⚫	Malondialdehyde reacts with ] and ] in DNA, forming ], the primary one being ], which is ].<ref name=martnett>{{cite journal |author=Marnett LJ |title=Lipid peroxidation-DNA damage by malondialdehyde |journal=Mutat. Res. |volume=424 |issue=1–2 |pages=83–95 |year=1999 |pmid=10064852 |doi=10.1016/S0027-5107(99)00010-X|bibcode=1999MRFMM.424...83M }}</ref> The guanidine group of arginine residues condense with malondialdehyde to give 2-aminopyrimidines.
	=== Analysis ===
⚫	MDA and other "]" (TBARS) condense with two equivalents of ] to give a fluorescent red derivative that can be assayed spectrophotometrically.<ref name=eEROS/><ref>http://www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33</ref> 1-Methyl-2-phenylindole is an alternative more selective reagent.<ref name=eEROS/>
		⚫	Human ] aldehyde dehydrogenase is capable of oxidizing malondialdehyde.
⚫	==Hazards==
	MDA is reactive and potentially mutagenic.
	== Pathology ==		=== Analysis ===
		⚫	Malondialdehyde and other ] (TBARS) condense with two equivalents of ] to give a fluorescent red derivative that can be assayed spectrophotometrically.<ref name=eEROS/><ref>{{cite web |url=http://www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33 |title=Thiobarbituric acid reactive substances (TBARS) Assay |website=www.amdcc.org |archive-url=https://web.archive.org/web/20060914082200/http://www.amdcc.org/shared/showFile.aspx?doctypeid=3&docid=33 |archive-date=September 14, 2006}}</ref> 1-Methyl-2-phenylindole is an alternative more selective reagent.<ref name=eEROS/>
	]s of patients suffering from ] and ] have increased levels of MDA, according to one study.<!--
		⚫	==Hazards and pathology ==
	--><ref name="pmid11850437">{{cite journal |author=Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ |title=Evidence of oxidative stress in human corneal diseases |journal=] |volume=50 |issue=3 |pages=341–51 |year=2002 |month=March |pmid=11850437 |doi= |url=http://www.jhc.org/cgi/pmidlookup?view=long&pmid=11850437}}</ref><!--
			Malondialdehyde is reactive and potentially mutagenic.<ref>Hartman PE, Putative mutagens and carcinogens in foods. IV. Malonaldehyde (malondialdehyde) Environ Mutagen. 1983;5(4):603-7</ref> It has been found in heated edible oils such as sunflower and palm oils.<ref>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}}</ref>
			]s of patients with ] and ] have increased levels of malondialdehyde, according to one study.<ref name="pmid11850437">{{cite journal |vauthors=Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ |title=Evidence of oxidative stress in human corneal diseases |journal=] |volume=50 |issue=3 |pages=341–51 |date=March 2002 |pmid=11850437 |doi=10.1177/002215540205000306 |doi-access=free }}</ref> MDA also can be found in tissue sections of joints from patients with ].<ref name="pmid17686167">{{cite journal |vauthors=Tiku ML, Narla H, Jain M, Yalamanchili P |title=Glucosamine prevents in vitro collagen degradation in chondrocytes by inhibiting advanced lipoxidation reactions and protein oxidation |journal=] |volume=9 |issue=4 |pages=R76 |year=2007 |pmid=17686167 |pmc=2206377 |doi=10.1186/ar2274 |doi-access=free }}</ref>
	--> MDA also can be found in tissue sections of joints from patients with ].<!--
			Levels of malondialdehyde can be also considered (as a marker of ]) to assess the membrane damage in spermatozoa; this is crucial because ] affects sperm function by altering membrane fluidity, permeability and impairing sperm functional competence.<ref>{{Cite journal|last1=Collodel|first1=G.|last2=Moretti|first2=E.|last3=Micheli|first3=L.|last4=Menchiari|first4=A.|last5=Moltoni|first5=L.|last6=Cerretani|first6=D.|date=March 2015|title=Semen characteristics and malondialdehyde levels in men with different reproductive problems|journal=Andrology|language=en|volume=3|issue=2|pages=280–286|doi=10.1111/andr.297|pmid=25331426|s2cid=28027300|doi-access=free}}</ref>
	--><ref name="pmid17686167">{{cite journal |author=Tiku ML, Narla H, Jain M, Yalamanchili P |title=Glucosamine prevents in vitro collagen degradation in chondrocytes by inhibiting advanced lipoxidation reactions and protein oxidation |journal=] |volume=9 |issue=4 |pages=R76 |year=2007 |pmid=17686167 |pmc=2206377 |doi=10.1186/ar2274 |url=http://arthritis-research.com/content/9/4/R76}}</ref>
	==See also==		==See also==
	*]		*]
	*]		*]
			*]
	==References==		==References==
	{{reflist}}		{{reflist}}
			]
	]		]
			]
	{{biochem-stub}}
	]
	]
	]