関: maleic acid

maleic acid

WordNet

a salt or ester of maleic acid; used as a nontricyclic antidepressant drug for psychomotor activation

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/10/17 21:45:05」(JST)

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Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO₂CCHCHCO₂H. Maleic acid is the cis-isomer of butenedioic acid, whereas fumaric acid is the trans-isomer. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few applications.

Physical properties

Maleic acid is a less stable molecule than fumaric acid. The difference in heat of combustion is 22.7 kJ·mol⁻¹. The heat of combustion is -1355 kJ/mole.^[4] Maleic acid is more soluble in water than fumaric acid. The melting point of maleic acid (135 °C) is also much lower than that of fumaric acid (287 °C). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding^[5] that takes place in maleic acid at the expense of intermolecular interactions, and that are not possible in fumaric acid for geometric reasons.

Production and industrial applications

In industry, maleic acid is derived by hydrolysis of maleic anhydride, the latter being produced by oxidation of benzene or butane.^[6]

Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis.^[7]

Maleic acid may be used to form acid addition salts with drugs to make them more stable, such as indacaterol maleate.

Maleic acid is also used as an adhesion promoter for different substrates, such as nylon and zinc coated metals e.g galvanized steel, in methyl methacrylate based adhesives.

Isomerization to fumaric acid

The major industrial use of maleic acid is its conversion to fumaric acid. This conversion, an isomerization, is catalysed by a variety of reagents, such as mineral acids and thiourea. Again, the large difference in water solubility makes fumaric acid purification easy.

The isomerization is a popular topic in schools. Maleic acid and fumaric acid do not spontaneously interconvert because rotation around a carbon carbon double bond is not energetically favourable. However, conversion of the cis isomer into the trans isomer is possible by photolysis in the presence of a small amount of bromine.^[8] Light converts elemental bromine into a bromine radical, which attacks the alkene in a radical addition reaction to a bromo-alkane radical; and now single bond rotation is possible. The bromine radicals recombine and fumaric acid is formed. In another method (used as a classroom demonstration), maleic acid is transformed into fumaric acid through the process of heating the maleic acid in hydrochloric acid solution. Reversible addition (of H⁺) leads to free rotation about the central C-C bond and formation of the more stable and less soluble fumaric acid.

Some bacteria produce the enzyme maleate isomerase, which is used by bacteria in nicotinate metabolism. This enzyme catalyses isomerization between fumarate and maleate.

Other reactions

Although not practised commercially, maleic acid can be converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation (ethanol / palladium on carbon).^[9] 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, being electrophilic, participates as a dienophile in many Diels-Alder reactions.

Maleates

The maleate ion is the ionized form of maleic acid. The maleate ion is useful in biochemistry as an inhibitor of transaminase reactions. Maleic acid esters are also called maleates, for instance dimethyl maleate.

Use in pharmaceutical drugs

Many drugs are provided as maleates, eg. carfenazine, chlorpheniramine, pyrilamine, methylergonovine, and thiethylperazine.

References

^ Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
^ ^a ^b Record in the GESTIS Substance Database of the IFA
^ CRC Handbook of Chemistry and Physics, 73rd ed.; CRC Press: Boca Raton, FL., 1993
^ Maleic Anhydride, Maleic Acid, and Fumaric Acid, Huntsman Petrochemical Corporation
^ M. N. G James, G. J. B Williams (1974). "A Refinement of the Crystal Structure of Maleic Acid". Acta Crystallographica. B30 (5) (5): 1249–1275. doi:10.1107/S0567740874004626.
^ Kurt Lohbeck, Herbert Haferkorn, Werner Fuhrmann and Norbert Fedtke "Maleic and Fumaric Acids" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000. doi:10.1002/14356007.a16_053
^ DSM glyoxylic acid production
^ Light isomerization experiment (from the University of Regensburg, with video)
^ Kwesi Amoa (2007). "Catalytic Hydrogenation of Maleic Acid at Moderate Pressures A Laboratory Demonstration". Journal of Chemical Education. 84 (12): 1948. doi:10.1021/ed084p1948.

External links

International Chemical Safety Card 1186
Calculator: Water and solute activities in aqueous maleic acid

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English Journal

Development and validation of multivariate calibration methods for simultaneous estimation of Paracetamol, Enalapril maleate and hydrochlorothiazide in pharmaceutical dosage form.

Singh VD1, Daharwal SJ2.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2017 Jan 15;171:369-375. doi: 10.1016/j.saa.2016.08.028. Epub 2016 Aug 20.
Three multivariate calibration spectrophotometric methods were developed for simultaneous estimation of Paracetamol (PARA), Enalapril maleate (ENM) and Hydrochlorothiazide (HCTZ) in tablet dosage form; namely multi-linear regression calibration (MLRC), trilinear regression calibration method (TLRC)
PMID 27569769

Fluvoxamine maleate normalizes striatal neuronal inflammatory cytokine activity in a Parkinsonian rat model associated with depression.

Dallé E1, Daniels WM1, Mabandla MV2.
Behavioural brain research.Behav Brain Res.2017 Jan 1;316:189-196. doi: 10.1016/j.bbr.2016.08.005. Epub 2016 Aug 25.
Cytokine dysfunction is associated with both depression and Parkinson's disease (PD) pathophysiology. Inflammatory cytokines in neural and behavioral processes are involved in the production and/or maintenance of depression in PD. In this study we looked at how Fluvoxamine treatment regulates depres
PMID 27569183

Isolation of yeast complex IV in native lipid nanodiscs.

Smirnova IA1, Sjöstrand D2, Li F3, Björck M2, Schäfer J2, Östbye H2, Högbom M4, von Ballmoos C5, Lander GC3, Ädelroth P2, Brzezinski P6.
Biochimica et biophysica acta.Biochim Biophys Acta.2016 Dec;1858(12):2984-2992. doi: 10.1016/j.bbamem.2016.09.004. Epub 2016 Sep 13.
We used the amphipathic styrene maleic acid (SMA) co-polymer to extract cytochrome c oxidase (CytcO) in its native lipid environment from S. cerevisiae mitochondria. Native nanodiscs containing one CytcO per disc were purified using affinity chromatography. The longest cross-sections of the native n
PMID 27620332

Japanese Journal

がん化学療法における副作用に対する「患者に優しい製剤」の開発

YAKUGAKU ZASSHI 138(2), 169-175, 2018
NAID 130006328033

Negative chemotaxis of Ralstonia pseudosolanacearum to maleate and identification of the maleate chemosensory protein

Journal of bioscience and bioengineering 124(6), 647-652, 2017-12
NAID 40021420076

Engineering a synthetic pathway for maleate in Escherichia coli

Nature Communications 8, 1153, 2017-10-27
NAID 120006365366

Related Pictures

★リンクテーブル★

リンク元	「マレイン酸」「マレイン酸塩」「マレイン酸エステル」「maleic acid」
拡張検索	「thiethylperazine maleate」「butaperazine maleate」「timolol maleate」

「マレイン酸」

Maleic acid, maleinic acid
Names
	Preferred IUPAC name (2Z)-But-2-enedioic acid
	Other names (Z)-butenedioic acid, cis-butenedioic acid, malenic acid, maleinic acid, toxilic acid
Identifiers
CAS Number	110-16-7
ChEBI	CHEBI:18300
ChEMBL	ChEMBL539648
ChemSpider	392248
ECHA InfoCard	100.003.403
EC Number	203-742-5
Jmol 3D model	Interactive image
KEGG	C01384
RTECS number	OM9625000
UNII	91XW058U2C
	InChI InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- Key: VZCYOOQTPOCHFL-UPHRSURJSA-N ; InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- Key: VZCYOOQTPOCHFL-UPHRSURJBG ;
	SMILES O=C(O)\C=C/C(=O)O ;
Properties
Chemical formula	C4H4O4
Molar mass	116.07 g·mol−1
Appearance	White solid
Density	1.59 g/cm³
Melting point	135 °C (275 °F; 408 K) (decomposes)
Solubility in water	478.8 g/L at 20 C
Acidity (pKa)	pka1 = 1.9; pka2 = 6.07
Hazards
Safety data sheet	MSDS from J. T. Baker
EU classification (DSD)	Harmful (Xn)
R-phrases	R22 R36/37/38
S-phrases	(S2) S26 S28 S37
NFPA 704	0 3 0
Related compounds
Related carboxylic acids	fumaric acid; succinic acid; crotonic acid
Related compounds	maleic anhydride; maleimide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: maleic acid, maleate
関: マレイン酸エステル、マレイン酸塩

不飽和ジカルボン酸
HOOCCH=CHCOOH

「マレイン酸塩」

　　[★]

英: maleate
関: マレイン酸、マレイン酸エステル

「マレイン酸エステル」

　　[★]

英: maleate
関: マレイン酸、マレイン酸塩

「maleic acid」

　　[★]

マレイン酸

関: maleate

「thiethylperazine maleate」

　　[★]

マレイン酸チエチルペラジン

関: thiethylperazine、thiethylperazine malate

「butaperazine maleate」

　　[★]

マレイン酸ブタペラジン

関: butaperazine

「timolol maleate」

　　[★] マレイン酸チモロール

[Merck-1] Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123

[GESTIS-2] Record in the GESTIS Substance Database of the IFA

[3] CRC Handbook of Chemistry and Physics, 73rd ed.; CRC Press: Boca Raton, FL., 1993

[4] Maleic Anhydride, Maleic Acid, and Fumaric Acid, Huntsman Petrochemical Corporation

[5] M. N. G James, G. J. B Williams (1974). "A Refinement of the Crystal Structure of Maleic Acid". Acta Crystallographica. B30 (5) (5): 1249–1275. doi:10.1107/S0567740874004626.

[6] Kurt Lohbeck, Herbert Haferkorn, Werner Fuhrmann and Norbert Fedtke "Maleic and Fumaric Acids" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000. doi:10.1002/14356007.a16_053

[7] DSM glyoxylic acid production

[8] Light isomerization experiment (from the University of Regensburg, with video)

[9] Kwesi Amoa (2007). "Catalytic Hydrogenation of Maleic Acid at Moderate Pressures A Laboratory Demonstration". Journal of Chemical Education. 84 (12): 1948. doi:10.1021/ed084p1948.

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案内

案内

maleate