| Revision as of 12:20, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476186004 of page Malic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 06:06, 2 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users2,076 edits Fixes image in dark mode |
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{{short description|Dicarboxylic acid responsible for apple acidity}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Distinguish|maleic acid|malonic acid}} |
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{{chembox |
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{{redirect|Malate|the district in Manila|Malate, Manila}} |
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| verifiedrevid = 447048636 |
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{{Chembox |
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| Name = Malic acid |
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| Reference = |
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| ImageFile = Malic acid2.png |
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| ImageName = Skeletal structure |
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| verifiedrevid = 476993436 |
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| ImageFile1 = Malic-acid-3D-balls.png |
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<!-- Names -->| Name = Malic acid |
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| ImageName1 = Ball-and-stick model |
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| IUPACName = |
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| IUPACName = hydroxybutanedioic acid |
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| OtherNames = <small>L</small>-Malic acid<br /><small>D</small>-Malic acid<br />(-)-Malic acid<br />(+)-Malic acid<br />(''S'')-Hydroxybutanedioic acid<br />(''R'')-Hydroxybutanedioic acid |
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| PIN = 2-Hydroxybutanedioic acid |
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| SystematicName = |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = {{Unbulleted list |
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| PubChem = 525 |
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| ''Hydroxybutanedioic acid'' |
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| ''2-Hydroxysuccinic acid'' |
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| ''<small>(L/D)</small>-Malic acid'' |
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| ''(±)-Malic acid'' |
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| ''(S/R)-Hydroxybutanedioic acid'' |
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}} |
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| data page pagename = <!-- Images --> |
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| ImageFile = Äpfelsäure3.svg |
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| ImageClass = skin-invert |
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| ImageSize = 180px |
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| ImageName = Skeletal structure |
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| ImageFile1 = Malic-acid-3D-balls.png |
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| ImageName1 = Ball-and-stick model |
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| ImageFile2 = Sample of racemic malic acid.jpg |
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| ImageSize2 = 250px |
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| ImageCaption2 = <small>DL</small>-Malic acid |
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| ImageNameR2 = <!-- Sections --> |
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| Section1 = {{Chembox Identifiers |
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| IUPHAR_ligand = 2480 |
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| PubChem = 525 |
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| PubChem1 = 92824 |
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| PubChem1_Comment = <small>D</small>-(+) |
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| PubChem2 = 222656 |
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| PubChem2_Comment = <small>L</small>-(–) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 817L1N4CKP |
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| UNII = 817L1N4CKP |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = D04843 |
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| KEGG = C00711 |
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| KEGG1 = C00497 |
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| KEGG1_Comment = <small>D</small>-(+) |
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| KEGG2 = C00149 |
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| KEGG2_Comment = <small>L</small>-(–) |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1455497 |
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| InChI = 1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9) |
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| InChI = 1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9) |
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| InChIKey = BJEPYKJPYRNKOW-UHFFFAOYAM |
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| InChIKey = BJEPYKJPYRNKOW-UHFFFAOYAM |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 6650 |
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| ChEBI = 6650 |
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| ChEBI1 = 30796 |
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| ChEBI1_Comment = <small>D</small>-(+) |
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| ChEBI2 = 30797 |
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| ChEBI2_Comment = <small>L</small>-(–) |
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| SMILES = O=C(O)CC(O)C(=O)O |
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| SMILES = O=C(O)CC(O)C(=O)O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BJEPYKJPYRNKOW-UHFFFAOYSA-N |
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| StdInChIKey = BJEPYKJPYRNKOW-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 617-48-1 |
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| CASNo = 6915-15-7 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo = 6915-15-7 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 510 |
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| ChemSpiderID = 510 |
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| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1=83793 |
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| ChemSpiderID1 = 83793 |
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| ChemSpiderID1_Comment = D-(+)-malic acid |
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| ChemSpiderID1_Comment = <small>D</small>-(+)-malic acid |
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| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID2 = 193317 |
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| ChemSpiderID2 = 193317 |
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| ChemSpiderID2_Comment = L-(-)-malic acid |
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| ChemSpiderID2_Comment = <small>L</small>-(–)-malic acid |
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| EINECS = 230-022-8 |
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| EINECS = 230-022-8 |
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}} |
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| CoE = 17 |
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| Section2 = {{Chembox Properties |
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| FEMA = 2655 |
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| AtmosphericOHRateConstant = |
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| JECFA = 619 |
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| Appearance = Colorless |
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| BoilingPt = |
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| BoilingPtC = |
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| BoilingPt_ref = |
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| BoilingPt_notes = |
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| Density = 1.609 g⋅cm<sup>−3</sup> |
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| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>5</sub> |
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| HenryConstant = |
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| LogP = |
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| MolarMass = 134.09 g/mol |
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| MeltingPt = |
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| MeltingPtC = 130 |
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| MeltingPt_ref = |
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| MeltingPt_notes = |
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| pKa = p''K''<sub>a1</sub> = 3.40<br/>p''K''<sub>a2</sub> = 5.20<ref>{{Cite book |url=https://www.worldcat.org/oclc/11865673 |title=Data for biochemical research |date=1986 |publisher=Clarendon Press |isbn=0-19-855358-7 |edition=3rd |location=Oxford |oclc=11865673}}</ref><br/>p''K''<sub>a3</sub> = 14.5<ref name="Silva Kong Hider 2009 pp. 771–778">{{cite journal | last1=Silva | first1=Andre M. N. | last2=Kong | first2=Xiaole | last3=Hider | first3=Robert C. | title=Determination of the pKa value of the hydroxyl group in the α-hydroxycarboxylates citrate, malate and lactate by 13C NMR: implications for metal coordination in biological systems | journal=BioMetals | volume=22 | issue=5 | date=2009 | issn=0966-0844 | doi=10.1007/s10534-009-9224-5 | pages=771–778| pmid=19288211 }}</ref> |
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| pKb = |
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| Solubility = 558 g/L (at 20 °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> |
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| Solvent = |
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}} |
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| Section3 = {{Chembox Structure |
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| Coordination = |
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}} |
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| Section4 = {{Chembox Thermochemistry |
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| Entropy = |
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}} |
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| Section5 = {{Chembox Explosive |
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| Section6 = {{Chembox Pharmacology |
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| ATCvet = |
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}} |
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| Section2 = {{Chembox Properties |
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| Section7 = {{Chembox Hazards |
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| AutoignitionPt = |
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| C=4 | H=6 | O=5 |
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| MeltingPtC = 130 |
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| ExploLimits = |
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| 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> |
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| Density = 1.609 g cm<sup>−3</sup> |
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| LD50 = |
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| pKa = p''K''<sub>a1</sub> = 3.40, p''K''<sub>a2</sub> = 5.20 <ref>Dawson, R. M. C. et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref> |
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| LC50 = |
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| Solubility = 558 g/L (at 20 °C)<ref></ref> |
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| ExternalSDS = |
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| GHSPictograms = {{GHS07}} |
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}} |
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| Section4 = {{Chembox Related |
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| Section9 = {{Chembox Related |
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| OtherAnions = ] |
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| OtherAnions = ] |
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| OtherCations = |
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| Function = ]s |
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| OtherFunctn = ]<br />]<br />] |
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| OtherFunction = ]<br />]<br />] |
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| OtherFunction_label = ]s |
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| OtherCpds = ]<br />]<br />]<br />] |
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| OtherCompounds = ]<br />]<br />]<br />] |
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'''Malic acid''' is an ] with the ] {{chem2|HO2CCH(OH)CH2CO2H}}. It is a ] that is made by all living organisms, contributes to the sour taste of fruits, and is used as a ]. Malic acid has two ] forms (<small>L</small>- and <small>D</small>-enantiomers), though only the <small>L</small>-isomer exists naturally. The ] and ]s of malic acid are known as '''malates'''. The malate ] is a ] in the ]. |
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==Etymology== |
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The word 'malic' is derived from Latin {{lang|la|mālum}}, meaning 'apple'. The related Latin word {{Lang|la|mālus}}, meaning 'apple tree', is used as the name of the genus '']'', which includes all apples and crabapples;<ref>{{Cite web |last=Peffley |first=Ellen |title=Peffley: Crabapples steal the show in autumn |url=https://www.lubbockonline.com/story/lifestyle/home-garden/2021/11/23/peffley-crabapples-steal-show-autumn/8716819002/ |access-date=2022-08-08 |website=Lubbock Avalanche-Journal |language=en-US}}</ref> and is the origin of other ] classifications such as ], ], and ]. |
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==Biochemistry== |
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<small>L</small>-Malic acid is the naturally occurring form, whereas a mixture of <small>L</small>- and <small>D</small>-malic acid is produced synthetically. |
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<gallery widths="210" heights="90" style="text-align:center"> |
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File:L-Äpfelsäure.svg|<small>L</small>-Malic acid (''S'') |
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File:D-Äpfelsäure.svg|<small>D</small>-Malic acid (''R'') |
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</gallery> |
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Malate plays an important role in ]. In the ] process, malate is a source of ] in the ]. In the ], (''S'')-malate is an intermediate, formed by the addition of an ] group on the ''si'' face of fumarate. It can also be formed from pyruvate via ]. |
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Malate is also synthesized by the ] of ] in the guard cells of plant leaves. Malate, as a double anion, often accompanies potassium cations during the uptake of solutes into the guard cells in order to maintain electrical balance in the cell. The accumulation of these solutes within the guard cell decreases the ], allowing water to enter the cell and promote aperture of the stomata. |
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==In food== |
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Malic acid was first isolated from ] by ] in 1785.<ref>Carl Wilhelm Scheele (1785) (On fruit and berry acid), ''Kongliga Vetenskaps Academiens Nya Handlingar'' (New Proceedings of the Royal Academy of Science), '''6''' : 17-27. From page 21: ''" ... vil jag hådanefter kalla den ''Åple-syran''."'' ( ... I will henceforth call it ''apple acid''.)</ref> ] in 1787 proposed the name '']'', which is derived from the ] word for apple, '']''—as is its ] name '']''.<ref>de Morveau, Lavoisier, Bertholet, and de Fourcroy, ''Méthode de Nomenclature Chimique'' (Paris, France: Cuchet, 1787), </ref><ref>{{Cite journal |last=Jensen |first=William B. |date=June 2007 |title=The Origin of the Names Malic, Maleic, and Malonic Acid |url=https://pubs.acs.org/doi/abs/10.1021/ed084p924 |journal=Journal of Chemical Education |language=en |volume=84 |issue=6 |pages=924 |doi=10.1021/ed084p924 |bibcode=2007JChEd..84..924J |issn=0021-9584}}</ref> |
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In German it is named '']'' (or ''Apfelsäure'') after plural or singular of a sour thing from the apple fruit, but the salt(s) are called ''Malat(e)''. |
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Malic acid is the main acid in many fruits, including ]s, ], ], ], ]s, ]s, ]es, ]s, ]s, and ],<ref> of {{cite web|title=Fruchtsäuren|url=http://www.spektrum.de/lexikon/biologie/fruchtsaeuren/25817|website=Wissenschaft Online Lexikon der Biologie|archive-url=https://web.archive.org/web/20160515170804/http://www.spektrum.de/lexikon/biologie/fruchtsaeuren/25817|archive-date=May 15, 2016|url-status=live}}</ref> and is present in lower concentrations in other fruits, such as ] It contributes to the sourness of unripe apples. ]s contain high proportions of the acid. It is present in ]s and in most wines with concentrations sometimes as high as 5 g/L.<ref>{{Cite book |last=Ough |first=C. S. |url=https://www.worldcat.org/oclc/16866762 |title=Methods for analysis of musts and wines |date=1988 |publisher=J. Wiley |isbn=0-471-62757-7 |edition=2nd |location=New York |pages=67 |oclc=16866762}}</ref> It confers a tart taste to ]; the amount decreases with increasing fruit ]. The taste of malic acid is very clear and pure in ], a plant for which it is the primary flavor. It is also the compound responsible for the tart flavor of ] spice. It is also a component of some artificial ] flavors, such as "salt and vinegar" flavored potato chips.<ref>{{cite web|url=http://www.seriouseats.com/2012/09/the-best-salt-and-vinegar-chips-tasting-brands-most-acidic.html|title=The Science Behind Salt and Vinegar Chips|work=seriouseats.com}}</ref> |
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The process of ] converts malic acid to much milder ]. Malic acid occurs naturally in all fruits and many vegetables, and is generated in fruit metabolism.<ref> {{Webarchive|url=https://web.archive.org/web/20180625212009/http://www.bartek.ca/malic_acid.html|date=2018-06-25}}, ] (retrieved 2 February 2012)</ref> |
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Malic acid, when added to food products, is denoted by ] E296. It is sometimes used with or in place of the less sour ] in sour sweets. These sweets are sometimes labeled with a warning stating that excessive consumption can cause irritation of the mouth. It is approved for use as a ] in the EU,<ref>UK Food Standards Agency: {{cite web |url=http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist |title=Current EU approved additives and their E Numbers |access-date=2011-10-27}}</ref> US<ref name="Food Additive Status List">{{cite journal |title=Food Additive Status List |journal=FDA |date=26 August 2021 |url=https://www.fda.gov/food/food-additives-petitions/food-additive-status-list |access-date=5 May 2022}}</ref> and Australia and New Zealand<ref>Australia New Zealand Food Standards Code{{cite web |url=http://www.comlaw.gov.au/Details/F2011C00827 |title=Standard 1.2.4 - Labelling of ingredients |date=8 September 2011 |access-date=2011-10-27}}</ref> (where it is listed by its ] 296). |
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Malic acid contains 10 kJ (2.39 kilocalories) of energy per gram.<ref name="FAO">{{cite book|last=Greenfield|first=Heather|title=Food composition data: production, management and use|year=2003|publisher=Food and Agriculture Organization of the United Nations|location=Rome|isbn=978-92-5-104949-5|page=146|url=https://books.google.com/books?id=KQRzKDr9bgcC&pg=PA146|edition=2|author2=Southgate, D.A.T.|access-date=10 February 2014}}</ref> |
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==Production and main reactions== |
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] malic acid is produced industrially by the double hydration of ]. In 2000, American production capacity was 5,000 tons per year. The ]s may be separated by ] of the racemic mixture. ''S''-Malic acid is obtained by fermentation of ].<ref>{{Ullmann | author = Karlheinz Miltenberge | title = Hydroxycarboxylic Acids, Aliphatic | doi = 10.1002/14356007.a13_507}}</ref> |
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] of malic acid in the presence of ] gives the ] ]:<ref>{{cite journal| title = Coumalic acid | journal= Organic Syntheses | volume= 31 | pages = 23| year = 1951| doi= 10.15227/orgsyn.031.0023| author = Richard H. Wiley, Newton R. Smith}}</ref> |
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:{{chem2|2 HO2CCH(OH)CH2CO2H -> HO2CC4H3O2 + 2 CO + 4 H2O}} |
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] and water are liberated during this reaction. |
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Malic acid was important in the discovery of the ] and the ], in which (−)-malic acid first is converted into (+)-chlorosuccinic acid by action of ]. Wet ] then converts the chlorine compound to (+)-malic acid, which then reacts with PCl<sub>5</sub> to the (−)-chlorosuccinic acid. The cycle is completed when silver oxide takes this compound back to (−)-malic acid. |
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{{sc|l}}-malic acid is used to ] ], a versatile resolving agent in its own right.<ref>{{cite journal |doi=10.15227/orgsyn.017.0080|title=D- and l-α-Phenylethylamine|journal=Organic Syntheses|year=1937|volume=17|page=80|author=A. W. Ingersoll}}</ref> |
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==Plant defense== |
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Soil supplementation with ] increases microbial synthesis of malic acid. This is thought to occur naturally as part of ], so ] with molasses can be used as a ] treatment in horticulture.<ref name="Rosskopf-et-al-2020">{{cite journal | last1=Rosskopf | first1=Erin | last2=Di Gioia | first2=Francesco | last3=Hong | first3=Jason C. | last4=Pisani | first4=Cristina | last5=Kokalis-Burelle | first5=Nancy | title=Organic Amendments for Pathogen and Nematode Control | journal=] | publisher=] | volume=58 | issue=1 | date=2020-08-25 | issn=0066-4286 | doi=10.1146/annurev-phyto-080516-035608 | pages=277–311| pmid=32853099 | s2cid=221360634 }}</ref> |
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==Interactive pathway map== |
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{{GlycolysisGluconeogenesis_WP534| highlight = Malic_acid }} |
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==See also== |
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* ] |
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* ] |
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* ] |
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* ] |
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* ], resulting from malic acid dehydration |
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==References== |
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{{Reflist}} |
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==External links== |
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* |
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{{citric acid cycle}} |
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{{Authority control}} |
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{{DEFAULTSORT:Malic Acid}} |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
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] |