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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/04/07 08:19:40」(JST)

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Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH₂(COOH)₂. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.

Biochemistry

The calcium salt of malonic acid occurs in high concentrations in beetroot. It exists in its normal state as white crystals. Malonic acid is the classic example of a competitive inhibitor: It acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.

Preparation

A classical preparation of malonic acid starts from chloroacetic acid:^[2]

Preparation of malonic acid from chloroacetic acid.

Sodium carbonate generates the sodium salt, which is then reacted with sodium cyanide to provide the cyano acetic acid salt via a nucleophilic substitution. The nitrile group can be hydrolyzed with sodium hydroxide to sodium malonate, and acidification affords malonic acid.

Malonic acid was first prepared in 1858 by the French chemist Victor Dessaignes (1800-1885) via the oxidation of malic acid.^[3]

Organic reactions

In a well-known reaction, malonic acid condenses with urea to form barbituric acid. Malonic acid is also frequently used as an enolate in Knoevenagel condensations or condensed with acetone to form Meldrum's acid. The esters of malonic acid are also used as a ⁻CH₂COOH synthon in the malonic ester synthesis.

Additionally, the coenzyme A derivative of malonate, malonyl-CoA, is an important precursor in fatty acid biosynthesis along with acetyl CoA. Malonyl CoA is formed from acetyl CoA by the action of acetyl-CoA carboxylase, and the malonate is transferred to an acyl carrier protein to be added to a fatty acid chain.

Applications

Malonic acid is a precursor to specialty polyesters. It can also be a component in alkyd resins. It is used in a number of manufacturing processes including the electronics industry.

Malonic acid is used as a building block chemical to produce numerous valuable compounds.^[4]

References

^ ^a ^b pKa Data Compiled by R. Williams (pdf; 77 kB)
^ Nathan Weiner. "Malonic acid". Org. Synth. ; Coll. Vol. 2, p. 376
^ See:
- Dessaignes (1858) "Note sur un acide obtenu par l'oxydation de l'acide malique" (Note on an acid obtained by oxidation of malic acid), Comptes rendus, 47 : 76-79.
- Dessaignes (1858) "Ueber eine durch Oxydation der Aepfelsäure erhaltene Säure" (On an acid obtained by oxidation of malic acid) Annalen der Chemie und Pharmacie, 107 : 251-254.
^ Malonic Acid & Derivatives

External links

pH-Spectrum of Disodium Malonate
pH-Spectrum of Malonate-copper-complex
Calculator: Water and solute activities in aqueous malonic acid
[1]

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

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English Journal

An unexpected fluctuating reactivity for odd and even carbon numbers in the TiO2-based photocatalytic decarboxylation of C2-C6 dicarboxylic acids.

Sun Y1, Chang W, Ji H, Chen C, Ma W, Zhao J.
Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2014 Feb 10;20(7):1861-70. doi: 10.1002/chem.201303236. Epub 2014 Jan 8.
The degradation behaviours of five straight-chain dicarboxylic acids (from ethanedioic acid to hexanedioic acid) were compared in aqueous TiO2-based photocatalysis. When all other conditions were identical, the degradation rates were found to fluctuate regularly with the parity of the number of carb
PMID 24402745

A high activity of Ti/SnO2-Sb electrode in the electrochemical degradation of 2,4-dichlorophenol in aqueous solution.

Niu J1, Maharana D, Xu J, Chai Z, Bao Y.
Journal of environmental sciences (China).J Environ Sci (China).2013 Jul 1;25(7):1424-30.
Electrochemical degradation of 2,4-dichlorophenol (2,4-DCP) in aqueous solution was investigated over Ti/SnO2-Sb anode. The factors influencing the degradation rate, such as applied current density (2-40 mA/cm2), pH (3-11) and initial concentration (5-200 mg/L) were evaluated. The degradation of 2,4
PMID 24218856

Rapid synthesis of flavor compound 4-ethyloctanoic acid under microwave irradiation.

Liu YP1, Yin DC, Chen HT, Sun BG.
International journal of molecular sciences.Int J Mol Sci.2010 Oct 25;11(10):4165-74. doi: 10.3390/ijms11104165.
Rapid synthesis of 4-ethyloctanoic acid by means of microwave irradiation is described. Diethyl malonate reacted with 2-ethyl-1-bromohexane in the presence of sodium ethoxide to give diethyl (2-ethylhexyl)malonate (1b). 1b was saponified in the solution of ethanol and potassium hydroxide and then ac
PMID 21152328

Japanese Journal

ONE-POT SYNTHESIS OF 2-(1,4-DIHYDRO-2H-3,1-BENZOTHIAZIN-2-YLIDENE)PROPANEDIOIC ACID DERIVATIVES BY THE REACTION OF 2-(1-BROMOALKYL)PHENYL ISOTHIOCYANATES WITH PROPANEDIOIC ACID DERIVATIVES USING SODIUM HYDRIDE

Kobayashi Kazuhiro,Ezaki Kosuke
Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 85(12), 3007-3013, 2012-12-01
NAID 40019500569

Isolation and characterization of bacterial strains Paenibacillus sp. and Bacillus sp. for kraft lignin decolorization from pulp paper mill waste

Chandra Ram,Singh Shail,Krishna Reddy M. M.,Patel D. K.,J. Purohit Hemant,Kapley Atya
The Journal of General and Applied Microbiology 54(6), 399-407, 2008
… namely, acetic acid, propanoic acid, butanoic acid, guaiacol, hexanoic acid, and ITRC S<SUB>8</SUB>, namely acetic acid, propanoic acid, ethanedioic acid, furan carboxylic acid, 2-propanoic acid, butanoic acid, 3-acetoxybutyric acid, propanedioic …
NAID 130004449251

Decolorization and degradation products of the melanoidins by hydrogen peroxide.

HAYASE Fumitaka,KIM Seon Bong,KATO Hiromichi
Agricultural and Biological Chemistry 48(11), 2711-2717, 1984
… by oxidative degradation of alkaline hydrogen peroxide were identified as 2- methyl-2, 4-pentanediol, Af, 7V-dimethylacetamide, phenol, acetic acid, oxalic acid, methylpropanedioic acid, propanedioic acid, 2-furancarboxylic acid, butanedioic acid, 2-hydroxypropanoic acid, 2, 5-furandicarboxylic aicd and 5-(hydroxymethyl)-2-furancarboxylic acid. …
NAID 130000027138

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★リンクテーブル★

リンク元

「マロン酸」

Malonic acid
Names
	IUPAC name propanedioic acid
	Other names methanedicarboxylic acid
Identifiers
CAS Registry Number	141-82-2
ChEBI	CHEBI:30794
ChEMBL	ChEMBL7942
ChemSpider	844
DrugBank	DB02175
	InChI InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) ; Key: OFOBLEOULBTSOW-UHFFFAOYSA-N ; InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7); Key: OFOBLEOULBTSOW-UHFFFAOYAJ ;
Jmol-3D images	Image; Image
PubChem	867
	SMILES O=C(O)CC(O)=O ; C(C(=O)O)C(=O)O ;
Properties
Molecular formula	C3H4O4
Molar mass	104.06 g·mol−1
Density	1.619 g/cm3
Melting point	135 to 137 °C (275 to 279 °F; 408 to 410 K) (decomposes)
Boiling point	decomposes
Solubility in water	Miscible
Acidity (pKa)	pKa1 = 2.83; pKa2 = 5.69
Related compounds
Other anions	malonate
Related carboxylic acids	acetic acid; oxalic acid; propionic acid; tartronic acid; acrylic acid; butyric acid; succinic acid; fumaric acid
Related compounds	propanone; propionaldehyde; propanedial; dimethyl malonate
Hazards
MSDS	External MSDS
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	verify (what is: /?)
	Infobox references

　　[★]

英: malonate, malonic acid
同: プロパン二酸 propanedioic acid
関: ジカルボン酸、コハク酸。メチルマロン酸

HOOC-CH₂-COOH

コハク酸の構造に類似　→　コハク酸脱水素酵素の働きを競合的に阻害　→　ミトコンドリアの呼吸阻害薬

[Williams-1] Ka Data Compiled by R. Williams (pdf; 77 kB)

[2] Nathan Weiner. "Malonic acid". Org. Synth. ; Coll. Vol. 2, p. 376

[3] See:

Dessaignes (1858) "Note sur un acide obtenu par l'oxydation de l'acide malique" (Note on an acid obtained by oxidation of malic acid), Comptes rendus, 47 : 76-79.

Dessaignes (1858) "Ueber eine durch Oxydation der Aepfelsäure erhaltene Säure" (On an acid obtained by oxidation of malic acid) Annalen der Chemie und Pharmacie, 107 : 251-254.

[4] Dessaignes (1858) "Note sur un acide obtenu par l'oxydation de l'acide malique" (Note on an acid obtained by oxidation of malic acid), Comptes rendus, 47 : 76-79.

[5] Dessaignes (1858) "Ueber eine durch Oxydation der Aepfelsäure erhaltene Säure" (On an acid obtained by oxidation of malic acid) Annalen der Chemie und Pharmacie, 107 : 251-254.

[4] Malonic Acid & Derivatives

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案内

propanedioic acid