FComEx: Maleic acid (PC000046)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:42 UTC

Update date

2017-01-19 02:36:11 UTC

FoodComEx ID

PC000046

FoodDB Record

FDB008113

Chemical Information

Name

Maleic acid

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. [HMDB]. Maleic acid is found in many foods, some of which are cocoa bean, lovage, roselle, and corn.

CAS Number

110-16-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2Z)-2-Butenedioate	HMDB
(2Z)-2-Butenedioic acid	HMDB
(2Z)-But-2-enedioate	HMDB
(2Z)-But-2-enedioic acid	HMDB
(2Z)-Butene-2-dioate	HMDB
(2Z)-Butene-2-dioic acid	HMDB
(Z)-2-Butenedioate	Generator
(Z)-2-Butenedioic acid	ChEBI
(Z)-2-Butenedioic acid, 9CI	db_source
(Z)-Butenedioate	Generator
(Z)-Butenedioic acid	ChEBI
2-Butenedioate	HMDB
2-Butenedioic acid	HMDB
cis-1,2-Ethylenedicarboxylate	Generator
cis-1,2-Ethylenedicarboxylic acid	ChEBI
cis-2-Butenedioate	HMDB
cis-2-Butenedioic acid	HMDB
cis-But-2-enedioate	Generator
cis-But-2-enedioic acid	ChEBI
cis-Butenedioate	Generator
cis-Butenedioic acid	ChEBI
cis-Ethylene-1,2-dicarboxylic acid	db_source
H2Male	ChEBI
Kyselina maleinova	HMDB
Maleate	Generator
Maleinic acid	HMDB
Malenic acid	HMDB
Malezid cm	HMDB
Scotchbond multipurpose etchant	HMDB
Toxilate	Generator

Chemical Formula

C4H4O4

IUPAC name

(2Z)-but-2-enedioic acid

InChI Identifier

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-

InChI Key

VZCYOOQTPOCHFL-UPHRSURJSA-N

Isomeric SMILES

OC(=O)\C=C/C(O)=O

Average Molecular Weight

116.0722

Monoisotopic Molecular Weight

116.010958616

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents