{{위키데이터 속성 추적}}
{{Chembox
| IUPACName = Malonic acid
| ImageFile = Malonsäure.svg
| ImageAlt = Skeletal formula of malonic acid
| ImageFile1 = Malonic acid molecule ball from xtal.png
| ImageAlt1 = Ball-and-stick model of the malonic acid molecule
| PIN = Propanedioic acid<ref>{{서적 인용|author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=746 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| OtherNames = Methanedicarboxylic acid
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 141-82-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9KX7ZMG0MK
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 30794
| PubChem = 867
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 7942
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02175
| SMILES = O=C(O)CC(O)=O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 844
| SMILES2 = C(C(=O)O)C(=O)O
| InChI = 1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
| InChIKey = OFOBLEOULBTSOW-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OFOBLEOULBTSOW-UHFFFAOYSA-N
 }}
| Section2 = {{Chembox Properties
| C=3 | H=4 | O=4
| MeltingPtC = 135 ~ 137
| Density = 1.619 g/cm<sup>3</sup>
| Solubility = 763 g/L
| pKa = pK<sub>a1</sub> = 2.83<ref name="Williams">[http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf pKa Data Compiled by R. Williams (pdf; 77&nbsp;kB)] {{webarchive|url=https://web.archive.org/web/20100602043012/http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf |date=2010-06-02 }}</ref> <br />pK<sub>a2</sub> = 5.69<ref name="Williams" />
| MagSus = -46.3·10<sup>−6</sup> cm<sup>3</sup>/mol
 }}
| Section7 = {{Chembox Hazards
| ExternalSDS = [https://beta-static.fishersci.com/content/dam/fishersci/en_US/documents/programs/education/regulatory-documents/sds/chemicals/chemicals-m/S25416.pdf External MSDS]
 }}
}}

'''말론산'''은 [[다이카복실산]]의 일종이며, [[석신산 탈수소효소]]의 [[경쟁적 저해제]]다.<ref>{{저널 인용
| last1 = Potter | first1 = V. R.
| last2 = Dubois | first2 = K. P.
| title = Studies on the Mechanism of Hydrogen Transport in Animal Tissues : Vi. Inhibitor Studies with Succinic Dehydrogenase
| journal = The Journal of General Physiology
| volume = 26
| issue = 4
| pages = 391–404
| year = 1943
| pmid = 19873352
| pmc = 2142566
 | doi=10.1085/jgp.26.4.391
}}</ref><ref>{{저널 인용|author=Dervartanian DV, Veeger C.|title=Studies on succinate dehydrogenase. I. Spectral properties of the purified enzyme and formation of enzyme-competitive inhibitor complexes|journal=Biochim. Biophys. Acta|volume=92|issue=|pages=233–47|year=1964|month=November|pmid=14249115}}</ref> 화학식은 C<sub>3</sub>H<sub>4</sub>O<sub>4</sub>이다.

== 병리학 ==
말론산 수치 상승 시 [[메틸말론산]] 수치 상승 효과가 동반될 때는 흔히 간과되는 대사 질환인<ref>{{저널 인용|제목=Exome sequencing identifies ACSF3 as a cause of combined malonic and methylmalonic aciduria|저널=Nature Genetics|성=NIH Intramural Sequencing Center Group|성2=Sloan|이름2=Jennifer L|url=http://www.nature.com/articles/ng.908|날짜=2011-09|권=43|호=9|쪽=883–886|언어=en|doi=10.1038/ng.908|issn=1061-4036|pmc=PMC3163731|pmid=21841779|성3=Johnston|이름3=Jennifer J|성4=Manoli|이름4=Irini|성5=Chandler|이름5=Randy J|성6=Krause|이름6=Caitlin|성7=Carrillo-Carrasco|이름7=Nuria|성8=Chandrasekaran|이름8=Suma D|성9=Sysol|이름9=Justin R}}</ref> [[복합 말론산 메틸말론산 산성뇨증]](CMAMMA)을 시사하는 소견일 수 있다. 혈장에서 말론산과 메틸말론산의 비율을 계산하여 전형적인 메틸말론산뇨와 감별할 수 있다.<ref>{{서적 인용|url=http://link.springer.com/10.1007/8904_2016_531|제목=A New Approach for Fast Metabolic Diagnostics in CMAMMA|성=de Sain-van der Velden|이름=Monique G. M.|성2=van der Ham|이름2=Maria|날짜=2016|편집자-성=Morava|편집자-이름=Eva|편집자2-성=Baumgartner|편집자2-이름=Matthias|권=30|출판사=Springer Berlin Heidelberg|위치=Berlin, Heidelberg|쪽=15–22|doi=10.1007/8904_2016_531|isbn=978-3-662-53680-3|pmc=PMC5110436|pmid=26915364|성3=Jans|이름3=Judith J.|성4=Visser|이름4=Gepke|성5=Prinsen|이름5=Hubertus C. M. T.|성6=Verhoeven-Duif|이름6=Nanda M.|성7=van Gassen|이름7=Koen L. I.|성8=van Hasselt|이름8=Peter M.|편집자3-성=Patterson|편집자3-이름=Marc|편집자4-성=Rahman|편집자4-이름=Shamima|편집자5-성=Zschocke|편집자5-이름=Johannes|편집자6-성=Peters|편집자6-이름=Verena}}</ref>

== 생화학 ==
미토콘드리아 [[지방산 합성]](mtFASII)에서 말론산은 시작 기질을 형성하며, 이 기질은 mtFASII의 첫 번째 단계에서 [[ACSF3|아실-CoA 합성 효소 계열 3]](ACSF3)에 의해 [[말로닐-CoA]]로 전환됩니다.<ref>{{저널 인용|제목=Mammalian ACSF3 Protein Is a Malonyl-CoA Synthetase That Supplies the Chain Extender Units for Mitochondrial Fatty Acid Synthesis|저널=Journal of Biological Chemistry|성=Witkowski|이름=Andrzej|성2=Thweatt|이름2=Jennifer|url=https://linkinghub.elsevier.com/retrieve/pii/S0021925820739189|날짜=2011-09|권=286|호=39|쪽=33729–33736|언어=en|doi=10.1074/jbc.M111.291591|pmc=PMC3190830|pmid=21846720|성3=Smith|이름3=Stuart}}</ref><ref>{{저널 인용|제목=The Mammalian Malonyl-CoA Synthetase ACSF3 Is Required for Mitochondrial Protein Malonylation and Metabolic Efficiency|저널=Cell Chemical Biology|성=Bowman|이름=Caitlyn E.|성2=Rodriguez|이름2=Susana|url=https://linkinghub.elsevier.com/retrieve/pii/S2451945617301095|날짜=2017-06|권=24|호=6|쪽=673–684.e4|언어=en|doi=10.1016/j.chembiol.2017.04.009|pmc=PMC5482780|pmid=28479296|성3=Selen Alpergin|이름3=Ebru S.|성4=Acoba|이름4=Michelle G.|성5=Zhao|이름5=Liang|성6=Hartung|이름6=Thomas|성7=Claypool|이름7=Steven M.|성8=Watkins|이름8=Paul A.|성9=Wolfgang|이름9=Michael J.}}</ref> 말론산은 [[산화적 인산화|전자 전달계]]를 구성하는 [[효소]]인 [[석신산 탈수소효소]](II번 복합체)의 [[경쟁적 저해제]]이다.<ref name="pardee_potter">{{저널 인용| vauthors = Pardee AB, Potter VR | title = Malonate inhibition of oxidations in the Krebs tricarboxylic acid cycle | journal = The Journal of Biological Chemistry | volume = 178 | issue = 1 | pages = 241–250 | date = March 1949 | pmid = 18112108 | doi = 10.1016/S0021-9258(18)56954-4 | doi-access = free }}</ref> 말론산은 석신산 탈수소효소의 [[활성 부위]]에 결합하지만 반응은 일으키지 않으며, 따라서 보통 기질로 작용하는 [[석신산]]과 경쟁한다. 이때 탈수소 반응에 필요한 −CH<sub>2</sub>CH<sub>2</sub>− 기는 가지고 있지 않다. 이 사실은 석신산 탈수소효소 활성 부위의 구조를 추론하는 데에 이용되었다. 석신산 탈수소효소가 억제되면서 [[세포 호흡]]은 저하된다.<ref>{{저널 인용| vauthors = Potter VR, Dubois KP | title = Studies on the Mechanism of Hydrogen Transport in Animal Tissues : VI. Inhibitor Studies with Succinic Dehydrogenase | journal = The Journal of General Physiology | volume = 26 | issue = 4 | pages = 391–404 | date = March 1943 | pmid = 19873352 | pmc = 2142566 | doi = 10.1085/jgp.26.4.391 }}</ref><ref>{{저널 인용|doi=10.1016/0926-6569(64)90182-8 |title=Studies on succinate dehydrogenase |year=1964 | vauthors = Dervartanian DV, Veeger C |journal=Biochimica et Biophysica Acta (BBA) - Specialized Section on Enzymological Subjects |volume=92 |issue=2 |pages=233–247 }}</ref> 말론산은 많은 음식에 자연적으로 포함되어 있는 물질이므로 사람을 포함한 [[포유류]]에도 존재한다.<ref>{{웹 인용|url=https://hmdb.ca/metabolites/HMDB0000691 |title=Metabocard for Malonic acid |website= Human Metabolome Database |access-date=2020-10-06 |date=2020-03-13 }}</ref>

== 각주 ==
{{각주}}
{{전거 통제}}

[[분류:다이카복실산]]
[[분류:3개의 탄소 원자를 가진 유기 화합물]]