Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:49 UTC |
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Update date | 2019-11-26 02:55:50 UTC |
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Primary ID | FDB001044 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | L-Malic acid |
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Description | L-Malic acid, also known as malate or L-apple acid, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. L-Malic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Malic acid exists in all eukaryotes, ranging from yeast to humans. L-Malic acid, with regard to humans, has been found to be associated with several diseases such as alzheimer's disease, colorectal cancer, eosinophilic esophagitis, and missing teeth; L-malic acid has also been linked to the inborn metabolic disorder 2-ketoglutarate dehydrogenase complex deficiency. |
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CAS Number | 97-67-6 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-L-Malic acid | ChEBI | (S)-(-)-Hydroxysuccinic acid | ChEBI | L-2-Hydroxybutanedioic acid | ChEBI | L-Apple acid | ChEBI | Malate | ChEBI | Malic acid | ChEBI | S-2-Hydroxybutanedioic acid | ChEBI | L-Malate | Kegg | (-)-L-Malate | Generator | (S)-(-)-Hydroxysuccinate | Generator | L-2-Hydroxybutanedioate | Generator | S-2-Hydroxybutanedioate | Generator | (-)-(S)-Malate | HMDB | (-)-(S)-Malic acid | HMDB | (-)-Hydroxysuccinate | HMDB | (-)-Hydroxysuccinic acid | HMDB | (-)-Malic acid | HMDB | (2S)-2-Hydroxybutanedioate | HMDB | (2S)-2-Hydroxybutanedioic acid | HMDB | (S)-Hydroxy-butanedioate | HMDB | (S)-Hydroxy-butanedioic acid | HMDB | (S)-Hydroxybutanedioate | HMDB | (S)-Hydroxybutanedioic acid | HMDB | (S)-Malic acid | HMDB | Apple acid | HMDB | L-(-)-Malic acid | HMDB | L-Hydroxybutanedioate | HMDB | L-Hydroxybutanedioic acid | HMDB | L-Hydroxysuccinate | HMDB | L-Hydroxysuccinic acid | HMDB | S-(-)-Malate | HMDB | S-(-)-Malic acid | HMDB | (S)-Malate | HMDB | L-Malic acid | ChEBI | (2S)-2-Hydroxysuccinic acid | HMDB | (2S)-Malic acid | HMDB | (S)-2-Hydroxysuccinic acid | HMDB | 2-Hydroxybutanedioic acid | HMDB | 2-Hydroxyethane-1,2-dicarboxylic acid | HMDB | 2-Hydroxysuccinic acid | HMDB | Deoxytetraric acid | HMDB | Hydroxybutanedioic acid | HMDB | Hydroxysuccinic acid | HMDB | Monohydroxybutanedioic acid | HMDB | alpha-Hydroxysuccinic acid | HMDB | α-Hydroxysuccinic acid | HMDB | (-)-(s)-malate | biospider | (-)-(s)-malic acid | biospider | (-)-hydroxysuccinate | biospider | (-)-hydroxysuccinic acid | biospider | (-)-l-malic acid | biospider | (-)-malic acid | biospider | (S)-(-)-2-Hydroxysuccinic acid | biospider | (s)-(-)-hydroxysuccinate | biospider | (s)-(-)-hydroxysuccinic acid | biospider | (s)-hydroxy-butanedioate | biospider | (s)-hydroxy-butanedioic acid | biospider | (s)-hydroxybutanedioate | biospider | (s)-hydroxybutanedioic acid | biospider | (s)-malate | biospider | (s)-malic acid | biospider | Butanedioic acid, hydroxy-, (s)- | biospider | FEMA 2655 | db_source | L-(-)-malic acid | biospider | L-apple acid | biospider | L-hydroxybutanedioate | biospider | L-hydroxybutanedioic acid | biospider | L-hydroxysuccinate | biospider | L-hydroxysuccinic acid | biospider | L-malate | biospider | Malic acid, (l) | biospider | Malic acid, 8CI; L-form | db_source | Malic acid, l- | biospider | S-(-)-malate | biospider | S-(-)-malic acid | biospider |
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Predicted Properties | |
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Chemical Formula | C4H6O5 |
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IUPAC name | (2S)-2-hydroxybutanedioic acid |
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InChI Identifier | InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1 |
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InChI Key | BJEPYKJPYRNKOW-REOHCLBHSA-N |
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Isomeric SMILES | O[C@@H](CC(O)=O)C(O)=O |
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Average Molecular Weight | 134.0874 |
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Monoisotopic Molecular Weight | 134.021523302 |
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Classification |
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Description | Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Hydroxy acids and derivatives |
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Sub Class | Beta hydroxy acids and derivatives |
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Direct Parent | Beta hydroxy acids and derivatives |
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Alternative Parents | |
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Substituents | - Short-chain hydroxy acid
- Beta-hydroxy acid
- Fatty acid
- Dicarboxylic acid or derivatives
- Alpha-hydroxy acid
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 35.83%; H 4.51%; O 59.66% | DFC |
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Melting Point | Mp 104-105° (100°) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | pKa2 5.1 | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]20D -28.7 (c, 5.5 in Py) (>99.8% ee) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0076-9000000000-ad60ea592282d09e4bd8 | 2020-02-03 | View Spectrum | GC-MS | L-Malic acid, 3 TMS, GC-MS Spectrum | splash10-000t-0940000000-142d6f5fc2efbf0d5109 | Spectrum | GC-MS | L-Malic acid, 3 TMS, GC-MS Spectrum | splash10-0002-0920000000-505483ce10ee3c4c9d20 | Spectrum | GC-MS | L-Malic acid, 3 TMS, GC-MS Spectrum | splash10-00di-9710000000-8f263d045d715ae9fe2b | Spectrum | GC-MS | L-Malic acid, non-derivatized, GC-MS Spectrum | splash10-000t-0940000000-142d6f5fc2efbf0d5109 | Spectrum | GC-MS | L-Malic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0920000000-505483ce10ee3c4c9d20 | Spectrum | GC-MS | L-Malic acid, non-derivatized, GC-MS Spectrum | splash10-00di-9710000000-8f263d045d715ae9fe2b | Spectrum | GC-MS | L-Malic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0910000000-fadd80af55894555ea72 | Spectrum | Predicted GC-MS | L-Malic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9100000000-aba7652c885a434930ef | Spectrum | Predicted GC-MS | L-Malic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-02j9-7191000000-b78c78194b39deee0ca4 | Spectrum | Predicted GC-MS | L-Malic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Malic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-9300000000-acd7d0159b8bb70b80fd | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0096-9000000000-7359292556d9d393d8f4 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0097-9000000000-a111335688b3219c1fc1 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00lr-0942120000-9504700a82dcf5dc3adb | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0a4i-0900000000-45e58d8a75d957cc5c41 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-0900000000-4ec56105367de7bf0027 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-001i-0900000000-1decf12f117200e0f28d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-03di-4900000000-86fd329658581c81c0ec | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00di-9100000000-82ffef2aa053f77cdbc5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-00di-9000000000-424bd54bc81a9db65a55 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-a916941735427ee3c48d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-001i-0900000000-1decf12f117200e0f28d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-4900000000-86fd329658581c81c0ec | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9100000000-82ffef2aa053f77cdbc5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-424bd54bc81a9db65a55 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-a916941735427ee3c48d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-03di-0900000000-afdfdad3edeeb90cb3e4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-01b9-4900000000-01b3a756de8f5a3ae6de | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-01b9-4900000000-5fc3f0befc374a6fcdd6 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kr-7900000000-2a07c36db6acea9015af | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00rj-9200000000-316c7803efd1dfb76523 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dl-9000000000-a442bcaaacb6f4eec14d | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001r-9800000000-03bfaee5de56f72ed927 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0079-9200000000-26a075efe73adc63a189 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-059f-9000000000-a3281a79477ac14e2eae | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 193317 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00149 |
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Pubchem Compound ID | 222656 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15589 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00156 |
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CRC / DFC (Dictionary of Food Compounds) ID | DCG74-V:BQR68-X |
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EAFUS ID | 2098 |
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Dr. Duke ID | L-MALIC-ACID |
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BIGG ID | 34045 |
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KNApSAcK ID | C00001192 |
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HET ID | LMR |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1030861 |
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SuperScent ID | Not Available |
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Wikipedia ID | Malic_acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Fumarate hydratase, mitochondrial | FH | P07954 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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odorless |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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