Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 14:22:58 -0600 |
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Update Date | 2015-06-03 17:19:07 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | (R)-Malate |
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Description | Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. In its ionised form it is malate, an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. |
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Structure | |
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Synonyms: | - (+)-D-malate
- (+)-D-malic acid
- (+-)-1-Hydroxy-1,2-ethanedicarboxylate
- (+-)-1-Hydroxy-1,2-ethanedicarboxylic acid
- (-)-1-Hydroxy-1,2-ethanedicarboxylate
- (-)-1-Hydroxy-1,2-ethanedicarboxylic acid
- (-)-hydroxysuccinate
- (-)-hydroxysuccinic acid
- (-)-L-malate
- (-)-L-malic acid
- (-)-malate
- (-)-malic acid
- (2R)-2-hydroxybutanedioate
- (2R)-2-hydroxybutanedioic acid
- (2S)-2-Hydroxybutanedioate
- (2S)-2-Hydroxybutanedioic acid
- (R)-(+)-2-Hydroxysuccinate
- (R)-(+)-2-Hydroxysuccinic acid
- (R)-hydroxybutanedioate
- (R)-hydroxybutanedioic acid
- (R)-malate
- (R)-Malic acid
- (S)-2-Hydroxybutanedioate
- (S)-2-Hydroxybutanedioic acid
- (S)-Hydroxybutanedioate
- (S)-Hydroxybutanedioic acid
- (S)-malate
- (S)-malic acid
- .+-.-malate
- .+-.-malic acid
- 2-Hydroxy-Butanedioate
- 2-Hydroxy-Butanedioic acid
- 2-HYDROXY-succinate
- 2-HYDROXY-SUCCINIC ACID
- 2-Hydroxybutanedioate
- 2-Hydroxybutanedioic acid
- 2-Hydroxydicarboxylate
- 2-Hydroxydicarboxylic acid
- 2-Hydroxyethane-1,2-dicarboxylate
- 2-Hydroxyethane-1,2-dicarboxylic acid
- 2-Hydroxysuccinate
- 2-Hydroxysuccinic acid
- A-Hydroxysuccinate
- A-Hydroxysuccinic acid
- Aepfelsaeure
- Alpha-Hydroxysuccinate
- Alpha-Hydroxysuccinic acid
- Apple acid
- Butanedioate, hydroxy-, (S)- (9CI)
- Butanedioate, hydroxy-, homopolymer
- Butanedioic acid, hydroxy-, (S)- (9CI)
- Butanedioic acid, hydroxy-, homopolymer
- D-(+)-Malate
- D-(+)-Malic acid
- D-Hydroxybutanedioate
- D-Hydroxybutanedioic acid
- D-Malate
- D-Malic acid
- Deoxytetrarate
- Deoxytetraric acid
- DL-hydroxybutanedioate
- DL-hydroxybutanedioic acid
- DL-Malate
- DL-malic acid
- DL-malic disodium salt
- DMR
- H2mal
- Hydroxy-(.+-.)-Butanedioate
- Hydroxy-(.+-.)-Butanedioic acid
- Hydroxy-(.+/-.)-Butanedioate
- Hydroxy-(.+/-.)-Butanedioic acid
- Hydroxy-(2S)-Butanedioate
- Hydroxy-(2S)-Butanedioic acid
- Hydroxy-(R)-Butanedioate
- Hydroxy-(R)-Butanedioic acid
- Hydroxy-(S)-Butanedioate
- Hydroxy-(S)-Butanedioic acid
- Hydroxy-Butanedioate
- Hydroxy-Butanedioic acid
- Hydroxy-Succinate
- Hydroxy-Succinic acid
- Hydroxybutandisaeure
- Hydroxybutanedioate
- Hydroxybutanedioate homopolymer
- Hydroxybutanedioic acid
- Hydroxybutanedioic acid homopolymer
- Hydroxysuccinate
- Hydroxysuccinic acid
- Hydroxysuccinnate (-)
- Hydroxysuccinnic acid (-)
- Kyselina hydroxybutandiova [czech]
- Kyselina jablecna
- Kyselina jablecna [czech]
- L(+)-Malate
- L(+)-Malic acid
- L-(-)-Malate
- L-(-)-Malic acid
- L-Mal
- L-Malate
- L-Malic acid
- MAL
- Malate
- Malate D-(+)-form
- Malate homopolymer
- Malate L-(-)-form
- Malate,(DL)
- Malic acid
- Malic acid D-(+)-form
- Malic acid homopolymer
- Malic acid L-(-)-form
- Malic acid,(DL)
- MLT
- Monohydroxybernsteinsaeure
- Musashi-no-ringosan
- Nchembio.145-comp29
- OAA
- Poly (L-malate)
- Poly (L-malic acid)
- Poly(malate)
- Poly(malic acid)
- Pomalus acid
- R,S(+-)-Malate
- R,S(+-)-Malic acid
- R,S-Malate
- R,S-Malic acid
- R,Smalate
- R,Smalic acid
- R-Malate
- R-Malic acid
- S-(-)-Malate
- S-(-)-Malic acid
- S-2-Hydroxybutanedioate
- S-2-Hydroxybutanedioic acid
- TEO
- α-Hydroxysuccinate
- α-Hydroxysuccinic acid
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Chemical Formula: | C4H6O5 |
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Weight: | Average: 134.0874 Monoisotopic: 134.021523302 |
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InChI Key: | BJEPYKJPYRNKOW-UWTATZPHSA-N |
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InChI: | InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1 |
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CAS number: | 636-61-3 |
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IUPAC Name: | (2R)-2-hydroxybutanedioic acid |
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Traditional IUPAC Name: | .+-.-malic acid |
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SMILES: | O[C@H](CC(O)=O)C(O)=O |
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Chemical Taxonomy |
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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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Physical Properties |
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State: | Solid |
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Charge: | -2 |
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Melting point: | 131-133 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 364 mg/mL at 20 oC [BEILSTEIN] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | - Butanoate metabolism ec00650
- Glyoxylate and dicarboxylate metabolism ec00630
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EcoCyc Pathways: | |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0930000000-53a536e3bc82b8e91612 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9610000000-883e07f52319a029b9f9 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0930000000-53a536e3bc82b8e91612 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9610000000-883e07f52319a029b9f9 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9100000000-add08efe51cfe6d9243c | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-02j9-7191000000-b78c78194b39deee0ca4 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0159-3900000000-b601107a03ca7060bc56 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-01b9-7900000000-7e16d13cd13953520b72 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-ed4a8a4776b51e62327c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-22c9ebc50090b4cd6671 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-6900000000-3b7d14a7ed7bb42627e4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01bj-9300000000-20f68e610aeba32d1947 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dl-9000000000-044292489a383c81ae1d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00m0-8900000000-9da4062d3c439ed2f7eb | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00ri-9200000000-c4d019ab4961e5b1a1ae | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fu-9000000000-bc073c2d0e1a2f8a82e3 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00y0-9400000000-b346287170f4b47937d9 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00du-9000000000-94fcc5032bed94eae77e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-43c40f8a7715a996c55b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00ri-9400000000-a20ca040dba0bb25ae2b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0095-9000000000-90064952bc6def150ecc | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-4dd1a07ea5d3aab2c6ea | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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