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{{short description|Dicarboxylic acid responsible for apple acidity}}
{{Distinguish|maleic acid|malonic acid}}
{{redirect|Malate|the district in Manila|Malate, Manila}}
{{Chembox
| Reference =
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 476993436
<!-- Names -->| Name = Malic acid
| IUPACName =
| PIN = 2-Hydroxybutanedioic acid
| SystematicName =
| OtherNames = {{Unbulleted list
| ''Hydroxybutanedioic acid''
| ''2-Hydroxysuccinic acid''
| ''<small>(L/D)</small>-Malic acid''
| ''(±)-Malic acid''
| ''(S/R)-Hydroxybutanedioic acid''
}}
| data page pagename = <!-- Images -->
| ImageFile = Äpfelsäure3.svg
| ImageSize = 180px
| ImageAlt =
| ImageName = Skeletal structure
| ImageCaption =
| ImageFile1 = Malic-acid-3D-balls.png
| ImageSize1 =
| ImageAlt1 =
| ImageName1 = Ball-and-stick model
| ImageCaption1 =
| ImageFile2 = Sample of racemic malic acid.jpg
| ImageSize2 = 250px
| ImageAlt2 =
| ImageName2 =
| ImageCaption2 = <small>DL</small>-Malic acid
| ImageFile3 =
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| ImageAltR2 =
| ImageNameR2 = <!-- Sections -->
| Section1 = {{Chembox Identifiers
| IUPHAR_ligand = 2480
| PubChem = 525
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 817L1N4CKP
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C00149
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1455497
| InChI = 1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
| InChIKey = BJEPYKJPYRNKOW-UHFFFAOYAM
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 6650
| SMILES = O=C(O)CC(O)C(=O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BJEPYKJPYRNKOW-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 6915-15-7
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 510
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1 = 83793
| ChemSpiderID1_Comment = D-(+)-malic acid
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID2 = 193317
| ChemSpiderID2_Comment = L-(–)-malic acid
| EINECS = 230-022-8
}}
| Section2 = {{Chembox Properties
| AtmosphericOHRateConstant =
| Appearance = Colorless
| BoilingPt =
| BoilingPtC =
| BoilingPt_ref =
| BoilingPt_notes =
| Density = 1.609{{nbsp}}g⋅cm<sup>−3</sup>
| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>5</sub>
| HenryConstant =
| LogP =
| MolarMass = 134.09 g/mol
| MeltingPt =
| MeltingPtC = 130
| MeltingPt_ref =
| MeltingPt_notes =
| pKa = p''K''<sub>a1</sub> = 3.40<br/>p''K''<sub>a2</sub> = 5.20<ref>Dawson, R. M. C. et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref>
| pKb =
| Solubility = 558{{nbsp}}g/L (at 20{{nbsp}}°C)<ref>{{cite web|url=http://chemblink.com/products/6915-15-7.htm|title=chemBlink Database of Chemicals from Around the World|work=chemblink.com|url-status=dead|archive-url=https://web.archive.org/web/20090122220534/http://www.chemblink.com/products/6915-15-7.htm|archive-date=2009-01-22}}</ref>
| SolubleOther =
| Solvent =
| VaporPressure =
}}
| Section3 = {{Chembox Structure
| Coordination =
| CrystalStruct =
| MolShape =
}}
| Section4 = {{Chembox Thermochemistry
| DeltaGf =
| DeltaHc =
| DeltaHf =
| Entropy =
| HeatCapacity =
}}
| Section5 = {{Chembox Explosive
| ShockSens =
| FrictionSens =
| DetonationV =
| REFactor =
}}
| Section6 = {{Chembox Pharmacology
| ATCvet =
| ATCCode_prefix =
| ATCCode_suffix =
| ATC_Supplemental =
| AdminRoutes =
| Bioavail =
| Excretion =
| HalfLife =
| Metabolism =
| Legal_status =
| Legal_AU =
| Legal_AU_comment =
| Legal_CA =
| Legal_CA_comment =
| Legal_NZ =
| Legal_NZ_comment =
| Legal_US =
| Legal_US_comment =
| Legal_UK =
| Legal_UK_comment =
| Legal_EU =
| Legal_EU_comment =
| Legal_UN =
| Legal_UN_comment =
| Pregnancy_category =
| Pregnancy_AU =
| Pregnancy_AU_comment =
| ProteinBound =
| Dependence_liability =
| Addiction_liability =
}}
| Section7 = {{Chembox Hazards
| AutoignitionPt =
| ExploLimits =
| FlashPt = 203 °C<ref>{{cite web |url=https://www.merckmillipore.com/en/product/msds/MDA_CHEM-100383|title=DL-Malic acid - (DL-Malic acid) SDS|last= |first= |date= |website=Merck Millipore|publisher= |access-date= |quote=}}</ref>
| LD50 =
| LC50 =
| MainHazards =
| NFPA-F =
| NFPA-H =
| NFPA-R =
| NFPA-S =
| PEL =
| REL =
| ExternalSDS =
| GHSPictograms = {{GHS07}}
| GHSSignalWord =
| HPhrases =
| PPhrases =
}}
| Section9 = {{Chembox Related
| OtherAnions = [[Malate]]
| OtherCations =
| OtherFunction = [[Succinic acid]]<br />[[Tartaric acid]]<br />[[Fumaric acid]]
| OtherFunction_label = [[carboxylic acid]]s
| OtherCompounds = [[1-butanol|Butanol]]<br />[[Butyraldehyde]]<br />[[Crotonaldehyde]]<br />[[Sodium malate]]
}}
}}
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