Record Information
Version1.0
Creation date2010-04-08 22:07:55 UTC
Update date2019-11-26 03:02:07 UTC
Primary IDFDB008113
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMaleic acid
DescriptionMaleic 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. [HMDB]. Maleic acid is found in many foods, some of which are cocoa bean, lovage, roselle, and corn.
CAS Number110-16-7
Structure
Thumb
Synonyms
SynonymSource
(Z)-2-Butenedioic acidChEBI
(Z)-Butenedioic acidChEBI
cis-1,2-Ethylenedicarboxylic acidChEBI
cis-But-2-enedioic acidChEBI
cis-Butenedioic acidChEBI
H2MaleChEBI
Toxilic acidChEBI
MaleateKegg
(Z)-2-ButenedioateGenerator
(Z)-ButenedioateGenerator
cis-1,2-EthylenedicarboxylateGenerator
cis-But-2-enedioateGenerator
cis-ButenedioateGenerator
ToxilateGenerator
(2Z)-2-ButenedioateHMDB
(2Z)-2-Butenedioic acidHMDB
(2Z)-But-2-enedioateHMDB
(2Z)-But-2-enedioic acidHMDB
(2Z)-Butene-2-dioateHMDB
(2Z)-Butene-2-dioic acidHMDB
2-ButenedioateHMDB
2-Butenedioic acidHMDB
cis-2-ButenedioateHMDB
cis-2-Butenedioic acidHMDB
Kyselina maleinovaHMDB
MAEHMDB
Maleinic acidHMDB
Malenic acidHMDB
Malezid CMHMDB
Scotchbond multipurpose etchantHMDB
Maleic acid, disodium saltHMDB
Maleic acid, monocopper (2+) saltHMDB
Maleic acid, potassium saltHMDB
Maleic acid, sodium saltHMDB
Sodium maleateHMDB
Hydrogen maleateHMDB
Maleic acid, ammonium saltHMDB
Maleic acid, calcium saltHMDB
Maleic acid, iron saltHMDB
Maleic acid, neodymium saltHMDB
Maleic acid, dipotassium saltHMDB
Maleic acid, monoammonium saltHMDB
Maleic acid, monosodium saltHMDB
(Z)-2-Butenedioic acid, 9CIdb_source
cis-Ethylene-1,2-dicarboxylic aciddb_source
Malezid cmHMDB
Predicted PropertiesNot Available
Chemical FormulaC4H4O4
IUPAC name
InChI IdentifierInChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
InChI KeyVZCYOOQTPOCHFL-UPHRSURJSA-N
Isomeric SMILESOC(=O)\C=C/C(O)=O
Average Molecular Weight116.0722
Monoisotopic Molecular Weight116.010958616
Classification
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 41.39%; H 3.47%; O 55.14%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID392248
ChEMBL IDCHEMBL539648
KEGG Compound IDC01384
Pubchem Compound ID444266
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00176
CRC / DFC (Dictionary of Food Compounds) IDDCG46-O:DCG46-O
EAFUS IDNot Available
Dr. Duke IDMALEIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDMAE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).