Maleic acid (BioCAD00000013668)
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Metabolite Card
Formula: C4H4O4 (116.011)
SMILES: OC(=O)\C=C/C(O)=O
Synonyms [en]
maleic acid; cis-butenedioic acid; maleate; cis-1,2-Ethylenedicarboxylic acid; (2Z)-but-2-enedioic acid; (Z)-Butenedioic acid
Last reviewed on 2024-06-28.
Cite this Page
Maleic acid. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000013668). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Maleic acid is a dicarboxylic acid, a molecule with two carboxyl groups. It 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 oC) is also much lower than that of fumaric acid (287 oC). Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. Maleic acid is used in making polyesters for fibre-reinforced laminated moldings and paint vehicles. More specifically it is used in the manufacture of phthalic-type alkyd and polyester resins, surface coatings, copolymers, plasticizers, lubricant additives and agricultural chemicals. It is also found in adhesives and sealants and as a preservative for oils and fats. In the natural world, maleic acid has been identified in ginseng, pineapple, cacao plants, sour cherries and corn. A large number of microbes are able to convert maleic acid to D-malate using the enzyme maleate hydratase (PMID: 1444397).
DBLinks
- CAS Registry Number: 110-16-7
- PubChem CID: 444266
- ChEBI: 18300
- HMDB: HMDB0000176
- LipidMaps:
- KEGG: C01384
- BioCyc: MALEATE
- NCBI MeSH: maleic acid
- Wikipedia: Maleic_acid
Other DBLinks
- CAS Registry Number: 10237-70-4
- CAS Registry Number: 110-16-7
- CAS Registry Number: 26099-09-2
- PubChem: 444266
- PubChem: 4579
- PubChem: 61293
- ChEBI: ChEBI:18300
- HMDB: HMDB0000176
- KEGG: C01384
- BioCyc: MALEATE
- NCBI MeSH: maleic acid
- Wikipedia: Maleic_acid
- DrugBank: DB04299
- RefMet: RM0153373
- MoNA: BAF_UVA_POS000156
- MoNA: BAF_UVA_POS000157
- MoNA: BAF_UVA_POS000158
- MoNA: CCMSLIB00000578307
- MoNA: CCMSLIB00005720797
- MoNA: EMBL-MCF_spec70217
- MoNA: EMBL_MCF_2_0_HRMS_Library000337
- MoNA: FiehnHILIC001308
- MoNA: FiehnHILIC002811
- MoNA: FiehnLib000391
- MoNA: GLS00150
- MoNA: HMDB0000176_c_ms_1063
- MoNA: HMDB0000176_ms_ms_206
- MoNA: HMDB0000176_ms_ms_207
- MoNA: HMDB0000176_ms_ms_208
- MoNA: JP004046
- MoNA: JP010474
- MoNA: KO001361
- MoNA: KO001362
- MoNA: KO001363
- MoNA: KO001364
- MoNA: KO001365
- MoNA: MoNA002184
- MoNA: MoNA002185
- MoNA: MoNA002186
- MoNA: MoNA023862
- MoNA: MoNA034329
- MoNA: MoNA034332
- MoNA: MoNA037979
- MoNA: OUF00336
- MoNA: PR100889
- MoNA: PS109801
- MoNA: PS109802
- MoNA: PS109807
- MoNA: PT210980
- Metlin: METLIN_4198
Class / Ontology
- WishartLab ClassyFire: [Dicarboxylic acids and derivatives] Dicarboxylic acids and derivatives
- RefMet: [Dicarboxylic acids] Dicarboxylic acids
- ChEBI: [CHEBI:18300] maleic acid
| ID | EC Number | Name |
|---|---|---|
| KEGG:R01087 | 5.2.1.1 | maleate cis-trans-isomerase |
| KEGG:R02419 | 4.2.1.31 | (R)-malate hydro-lyase |
| KEGG:R03540 | 3.5.1.107 | maleamate amidohydrolase |
| KEGG:R11257 | 3.7.1.23 | (2Z)-4,6-dioxohept-2-enedioate acylhydrolase |
| BioCyc:RXN-10447 | 3.7.1.23 | CPD-1070 + WATER --> PROTON + MALEATE + PYRUVATE |
| BioCyc:MALEATE-HYDRATASE-RXN | 4.2.1.31 | CPD-660<=>WATER + MALEATE |
| BioCyc:RXN-646 | 3.5.1.107 | MALEAMATE + WATER --> MALEATE + AMMONIUM |
| BioCyc:MALEATE-ISOMERASE-RXN | 5.2.1.1 | MALEATE<=>FUM |