Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 05:17:11 UTC |
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Update Date | 2014-12-24 20:26:57 UTC |
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Accession Number | T3D4800 |
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Identification |
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Common Name | Maleic acid |
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Class | Small Molecule |
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Description | Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions. |
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Compound Type | - Food Toxin
- Household Toxin
- Industrial/Workplace Toxin
- Metabolite
- Natural Compound
- Organic Compound
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Chemical Structure | |
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Synonyms | Synonym | (2Z)-2-Butenedioate | (2Z)-2-Butenedioic acid | (2Z)-but-2-enedioate | (2Z)-but-2-enedioic acid | (2Z)-Butene-2-dioate | (2Z)-Butene-2-dioic acid | (Z)-2-Butenedioate | (Z)-2-Butenedioic acid | (z)-butenedioate | (z)-butenedioic acid | 2-Butenedioate | 2-Butenedioic acid | cis-1,2-Ethylenedicarboxylic acid | cis-2-Butenedioate | cis-2-Butenedioic acid | cis-But-2-enedioate | cis-But-2-enedioic acid | Cis-butenedioate | Cis-butenedioic acid | H2male | Kyselina maleinova | MAE | Maleate | Maleinic acid | Malenic acid | Malezid CM | Scotchbond multipurpose etchant | Toxilic acid |
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Chemical Formula | C4H4O4 |
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Average Molecular Mass | 116.072 g/mol |
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Monoisotopic Mass | 116.011 g/mol |
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CAS Registry Number | 110-16-7 |
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IUPAC Name | (2Z)-but-2-enedioic acid |
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Traditional Name | maleic acid |
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SMILES | [H]\C(=C(/[H])C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- |
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InChI Key | InChIKey=VZCYOOQTPOCHFL-UPHRSURJSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Dicarboxylic acids and derivatives |
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Direct Parent | Dicarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Fatty acyl
- Fatty acid
- Unsaturated fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Endogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | - Fibroblasts
- Muscle
- Neuron
- Pancreas
- Platelet
- Prostate
- Spleen
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 130.5°C | Boiling Point | Not Available | Solubility | 4.41E+005 mg/L (at 25°C) | LogP | -0.48 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0900000000-170a9d63d0cb31451c1d | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-001j-5940000000-59e85bafafc1675e24ad | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0uxs-9000000000-d768b92d45a58ec32ec7 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004i-9000000000-617284552377852c7c46 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-0910000000-15f30f525d5ea74dc9d4 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0900000000-170a9d63d0cb31451c1d | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-001j-5940000000-59e85bafafc1675e24ad | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0900000000-4b46518e6c4f0c6724f2 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01ba-9200000000-52f88e04bac0ff8cdf17 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00di-8920000000-06da44f348d0fe0358b3 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-00di-9200000000-77d8b2c7abcec2e3d5a1 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-00di-9200000000-8d8a8b14a723e0363227 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0229-9700000000-061b31801a2ae4703fc5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive | splash10-0uxs-9000000000-d768b92d45a58ec32ec7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-03di-2900000000-6bbe33cf398e663af0fc | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-00di-9100000000-550ee9efb3babd781bca | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00di-9000000000-18e922c569242e2111e7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-00di-9000000000-f344fe84d76f2bf06f91 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-00fu-9000000000-6f90988f5d68f87b52d2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-00di-9400000000-99bc7f4db87479b4122a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-2900000000-6bbe33cf398e663af0fc | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9100000000-550ee9efb3babd781bca | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-18e922c569242e2111e7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-f344fe84d76f2bf06f91 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00fu-9000000000-6f90988f5d68f87b52d2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-00di-9400000000-99bc7f4db87479b4122a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-31211857acba85ea77cd | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-deb5cdbb73c1005a302e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-00di-9000000000-58cd192c368bc09a750e | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-9800000000-dbf34563376daeb2901f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00xs-9200000000-113bf08cdc77707ed3ad | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00fr-9000000000-f32d7ec65e8649bc2b0a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-2900000000-408d53a9fff7acc8ca23 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-6900000000-f149e9e5a34e27dd4d4e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fxt-9000000000-cae5f71dc27daaf17d9e | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB04299 |
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HMDB ID | HMDB00176 |
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PubChem Compound ID | 444266 |
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ChEMBL ID | CHEMBL539648 |
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ChemSpider ID | 392248 |
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KEGG ID | C01384 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 18300 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | MAE |
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ACToR ID | Not Available |
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Wikipedia Link | Maleic acid |
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References |
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Synthesis Reference | Yasuhisha Fukumoto, Noboru Moriyama, Takashi Itoi, “Maleic acid copolymer, production thereof and scale-preventing agent containing the same.” U.S. Patent US4589995, issued August, 1933. |
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MSDS | Link |
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General References | - Kotikoski H, Oksala O, Vapaatalo H, Aine E: Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers. Acta Ophthalmol Scand. 2003 Aug;81(4):355-60. [12859262 ]
- Herreras JM, Pastor JC, Calonge M, Asensio VM: Ocular surface alteration after long-term treatment with an antiglaucomatous drug. Ophthalmology. 1992 Jul;99(7):1082-8. [1495787 ]
- Klose T, Welzel PB, Werner C: Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles. Colloids Surf B Biointerfaces. 2006 Aug 1;51(1):1-9. Epub 2006 May 17. [16797943 ]
- Renner L, Pompe T, Salchert K, Werner C: Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics. Langmuir. 2004 Mar 30;20(7):2928-33. [15835174 ]
- Gong Z, Lv Y, Huang Y, Zhang Z: Determination of ergometrine maleate by fluorescence detection. Luminescence. 2005 May-Jun;20(3):124-8. [15924314 ]
- Goes MF, Sinhoreti MA, Consani S, Silva MA: Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces. Braz Dent J. 1998;9(1):3-10. [9835798 ]
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
- Gallagher RM: Menstrual migraine and intermittent ergonovine therapy. Headache. 1989 Jun;29(6):366-7. [2759844 ]
- Seki T, Wakabayashi M, Nakagawa T, Imamura M, Tamai T, Nishimura A, Yamashiki N, Okamura A, Inoue K: Hepatic infarction following percutaneous ethanol injection therapy for hepatocellular carcinoma. Eur J Gastroenterol Hepatol. 1998 Nov;10(11):915-8. [9872612 ]
- Snider BJ, Moss JL, Revilla FJ, Lee CS, Wheeler VC, Macdonald ME, Choi DW: Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults. Neuroscience. 2003;120(3):617-25. [12895502 ]
- Lavit M, Saivin S, Boudra H, Michel F, Martin A, Cahiez G, Labaune JP, Chomard JM, Houin G: Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC. Arzneimittelforschung. 2000 Jul;50(7):640-4. [10965422 ]
- Strasser G, Grabner G: The influence of long-term treatment with timolol on human tear lysozyme albumin content. Graefes Arch Clin Exp Ophthalmol. 1982;218(2):93-5. [7075967 ]
- Glazunova OO, Korepanova EA, Efimov VS, Smirnov AI, Vladimirov YuA: A synthetic polycation, a copolymer of 1-vinyl-3-methylimidazole iodide with maleic acid diethyl ester, increases passive ionic permeability in erythrocyte membranes modified by fatty acids. Membr Cell Biol. 1998;12(3):401-9. [10024972 ]
- Yoshida H, Onda M, Tajiri T, Uchida E, Arima Y, Mamada Y, Yamamoto K, Kaneko M, Terada Y, Kumazaki T: Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer. Hepatogastroenterology. 1999 Jul-Aug;46(28):2612-5. [10522050 ]
- Benderli Y, Gokce K, Buyukgokcesu S: In vitro shear bond strength of adhesive to normal and fluoridated enamel under various contaminated conditions. Quintessence Int. 1999 Aug;30(8):570-5. [10635272 ]
- Liu Y, Yanai R, Lu Y, Hirano S, Sagara T, Nishida T: Effects of antiglaucoma drugs on collagen gel contraction mediated by human corneal fibroblasts. J Glaucoma. 2006 Jun;15(3):255-9. [16778650 ]
- Dorr J, Roth K, Zurbuchen U, Deisz R, Bechmann I, Lehmann TN, Meier S, Nitsch R, Zipp F: Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate. J Neuroimmunol. 2005 Oct;167(1-2):204-9. [16043230 ]
- Turcan RG, Hillbeck D, Hartley TE, Gilbert PJ, Coe RA, Troke JA, Vose CW: Disposition of [14C]velnacrine maleate in rats, dogs, and humans. Drug Metab Dispos. 1993 Nov-Dec;21(6):1037-47. [7905382 ]
- Chen CN, Huang GF, Guo MK, Lin CP: An in vitro study on restoring bond strength of a GIC to saliva contaminated enamel under unrinse condition. J Dent. 2002 Jul-Aug;30(5-6):189-94. [12450709 ]
- Daykin CA, Foxall PJ, Connor SC, Lindon JC, Nicholson JK: The comparison of plasma deproteinization methods for the detection of low-molecular-weight metabolites by (1)H nuclear magnetic resonance spectroscopy. Anal Biochem. 2002 May 15;304(2):220-30. [12009699 ]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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