Malonic acid

Malonic acid
Malonic acid
Identifiers
CAS number 141-82-2 YesY
PubChem 867
DrugBank DB02175
ChEMBL CHEMBL7942 N
Jmol-3D images Image 1
Properties
Molecular formula C3H4O4
Molar mass 104.06 g mol−1
Exact mass 104.010959
Density 1.619 g/cm3
Melting point

135–136 °C

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
 N acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

Contents

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:[1]

Synthesis of malonic acid.png

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.

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.

References

External links


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Look at other dictionaries:

  • malonic acid — [mə lō′nik, məlän′ik] n. [Fr malonique, altered < malique: see MALIC ACID] a crystalline, dibasic acid, HOOCCH2COOH, obtained from malic acid by oxidation and used in synthesizing barbiturates …   English World dictionary

  • malonic acid — Chem. a white, crystalline, water soluble, dibasic acid, C3H4O4, easily decomposed by heat: used chiefly as an intermediate in the synthesis of barbiturates. [1885 90] * * * ▪ chemical compound also called  Propanedioic Acid        (HO2CCH2CO2H) …   Universalium

  • malonic acid — məˈlōnik , länik noun Etymology: malonic from F. malonique (in acide malonique malonic acid), alteration of malique malic (in acide malique malic acid) more at malic acid : a crystalline dicarboxylic acid CH2(COOH)2 obtained by oxidation of malic …   Useful english dictionary

  • malonic acid — malono rūgštis statusas T sritis chemija formulė CH₂(COOH)₂ atitikmenys: angl. malonic acid rus. малоновая кислота ryšiai: sinonimas – propano dirūgštis …   Chemijos terminų aiškinamasis žodynas

  • malonic acid — A dicarboxylic acid of importance in intermediary metabolism; an inhibitor of succinate dehydrogenase. SYN: propanedioic acid. * * * ma·lo·nic acid mə lōn ik , län n a crystalline dicarboxylic acid CH2(COOH)2 used esp. in the form of its diethyl… …   Medical dictionary

  • malonic acid — noun a white crystalline dicarboxylic acid, CH(COOH), used in making barbiturates See Also: malonate …   Wiktionary

  • malonic acid — ma•lo′nic ac′id [[t]məˈloʊ nɪk, ˈlɒn ɪk[/t]] n. chem. a white, crystalline, water soluble, dibasic acid, C3H4O4, used chiefly in the synthesis of barbiturates • Etymology: < F (acide) malonique (1858), alter. ofmalique malic …   From formal English to slang

  • malonic acid — /məˌlɒnɪk ˈæsəd/ (say muh.lonik asuhd), /məˌloʊnɪk/ (say muh.lohnik) noun a dibasic acid, CH2(COOH)2, easily decomposed by heat. {French malonique, alteration of malique malic} …  

  • malonic — MALÓNIC adj. (chim.; în sintagma) Acid malonic = acid dicarboxilic folosit împreună cu derivaţii săi în sinteze organice şi farmaceutice. – Din fr. malonique. Trimis de claudia, 13.09.2007. Sursa: DEX 98  malónic adj. m. Trimis de siveco,… …   Dicționar Român

  • Malonic anhydride — Malonic anhydride …   Wikipedia

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