Showing Compound Maleic acid (FDB008113)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:55 UTC

Update date

2019-11-26 03:02:07 UTC

Primary ID

FDB008113

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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

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Search:

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

Showing 1 to 10 of 46 entries

Predicted Properties

Property	Value	Source
Water Solubility	24.1 g/L	ALOGPS
logP	0.21	ALOGPS
logP	-0.041	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	3.05	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	24.61 m³·mol⁻¹	ChemAxon
Polarizability	9.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

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.

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

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 Framework

Aliphatic acyclic compounds

External Descriptors

butenedioic acid (CHEBI:18300 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 41.39%; H 3.47%; O 55.14%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-170a9d63d0cb31451c1d	Spectrum
GC-MS	Fumaric acid, 2 TMS, GC-MS Spectrum	splash10-001j-5940000000-59e85bafafc1675e24ad	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0uxs-9000000000-d768b92d45a58ec32ec7	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-004i-9000000000-617284552377852c7c46	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0910000000-15f30f525d5ea74dc9d4	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-170a9d63d0cb31451c1d	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-001j-5940000000-59e85bafafc1675e24ad	Spectrum
GC-MS	Fumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-4b46518e6c4f0c6724f2	Spectrum
Predicted GC-MS	Fumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01ba-9200000000-52f88e04bac0ff8cdf17	Spectrum
Predicted GC-MS	Fumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-8920000000-06da44f348d0fe0358b3	Spectrum
Predicted GC-MS	Fumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fumaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fumaric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fumaric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9200000000-77d8b2c7abcec2e3d5a1	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9200000000-8d8a8b14a723e0363227	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0229-9700000000-061b31801a2ae4703fc5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0uxs-9000000000-d768b92d45a58ec32ec7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-2900000000-6bbe33cf398e663af0fc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9100000000-550ee9efb3babd781bca	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-18e922c569242e2111e7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-9000000000-f344fe84d76f2bf06f91	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00fu-9000000000-6f90988f5d68f87b52d2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00di-9400000000-99bc7f4db87479b4122a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-2900000000-6bbe33cf398e663af0fc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9100000000-550ee9efb3babd781bca	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-18e922c569242e2111e7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-f344fe84d76f2bf06f91	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00fu-9000000000-6f90988f5d68f87b52d2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-9400000000-99bc7f4db87479b4122a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-31211857acba85ea77cd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-deb5cdbb73c1005a302e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-9000000000-58cd192c368bc09a750e	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9800000000-dbf34563376daeb2901f	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xs-9200000000-113bf08cdc77707ed3ad	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fr-9000000000-f32d7ec65e8649bc2b0a	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-408d53a9fff7acc8ca23	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-6900000000-f149e9e5a34e27dd4d4e	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fxt-9000000000-cae5f71dc27daaf17d9e	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum