MALONIC ACID

MALONIC ACID

CAS Number: 141-82-2
EC Number: 205-503-0
Molecular Mass: 104.06
Molecular Formula: CH2COOH2
IUPAC: propanedioic acid

Malonic 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'.

Malonic acid, formally propanedioic acid, is the second-smallest aliphatic dicarboxylic acid. (Oxalic acid is the smallest.) 
Malonic acid should not be confused with malic or maleic acid, both of which also contain two carboxyls.
Malonic acid is a white crystalline solid with a decomposition point of ≈135 °C. 
Malonic acid is highly soluble in water and oxygenated solvents. 
Malonic acid has numerous commercial uses: 
Malonic acid is a precursor to specialty polyesters; Malonic acid is used in the manufacture of barbiturates, coatings, and biodegradable containers; and Malonic acid is even a component of surgical adhesives.

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'.

Uses
Malonic acid is used as a precursor in polymers and polyester.
Malonic acid is used in flavours as well as the fragrance industry.
Malonic acid is used to control the acidity.
Malonic acid is used in pharmaceutical products.
Malonic acid is used as a cross-linking agent between potato starch and cornstarch to enhance its mechanical properties.
Malonic acid is used in the preparation of barbituric salt.
Malonic acid is used in electroplating.
Malonic acid is used to produce vitamin B1, vitamin B6, vitamin B2, and amino acids.
Malonic acid is used in chemical synthesis as a building block.

Malonic acid, also known as malonate or H2MALO, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. 
These are organic compounds containing exactly two carboxylic acid groups. 
Malonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 
Malonic acid exists in all living species, ranging from bacteria to humans. 
Within humans, malonic acid participates in a number of enzymatic reactions. 
In particular, malonic acid and acetic acid can be converted into acetoacetic acid; which is mediated by the enzyme fatty acid synthase. 

What is Malonic acid?
Malonic acid is also known as Propanedioic Acid or Dicarboxymethane. 
The name is derived from a Greek word Malon which means apple. 
Malonates are the ionized form of malonic acid, along with its esters and salts. 
Malonic acid appears as a white crystal or crystalline powder.
Malonic acid dissolves in alcohol, pyridine, and ether.

Malonic acid was first prepared in the year, 1858 by the French chemist Victor Dessaignes by the oxidation of malic acid. 
Malonic acid is found in some fruit’s viz citrus fruits. 
The amount of malonic acid produced from fruits through organic farming is greater than the fruits grown through conventional agriculture. 
Malonic acid can be produced through the fermentation of glucose.

Beta ketoacyl synthase domain. 
In addition, malonic acid and coenzyme A can be biosynthesized from malonyl-CoA through Malonic acids interaction with the enzyme fatty acid synthase. 
malonyl/acetyl transferase domain. 
An Malonic acid in which the two carboxy groups are separated by a single methylene group. 
In humans, malonic acid is involved in fatty acid biosynthesis. Outside of the human body, Malonic acid has been detected, but not quantified in, several different foods, such as red beetroots, corns, scarlet beans, common beets, and cow milks. 
This could make malonic acid a potential biomarker for the consumption of these foods. 
Malonic acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, combined malonic and methylmalonic aciduria, and early preeclampsia; malonic acid has also been linked to the inborn metabolic disorder malonyl-coa decarboxylase deficiency.

Malonic acid is a dicarboxylic acid with structural formula CH2(COOH)2 and chemical formula C3H4O4. 
The name malonic acid originated from the word ‘Malon’ which is Greek for ‘apple’. 
Methane Dicarboxylic acid is another name for malonic acid. 
The ester and salts of malonic acid are called malonates. 
The dicarboxylic acid has organic reactions similar to the monocarboxylic acid where amide, ester, anhydride, and chloride derivatives are formed. 
Lastly, the malonic ester malonate as a coenzyme A derivative malonyl CoA that is as important a precursor as Acetyl CoA in the biosynthesis of fatty acids. 

Synthesis of Malonic Acid 
The synthesis of malonic acid usually begins with chloroacetic acid. 
Malonic acid is also synthesized by cyanoacetic acid or by acid saponification reaction of malonates. 
From monochloroacetic acid, Malonic acid is produced by sodium or potassium cyanide. 
The sodium carbonate primarily breaks down to give sodium salt which reacts with sodium cyanide to give sodium salt of cyanoacetic acid by the process of nucleophilic substitution.
Further, via hydrolyzation, the nitrile group binds with sodium malonate, whose acidification results in the production of malonic acid. 

Malonic acid, also called Propanedioic Acid, (HO2CCH2CO2H), a dibasic organic acid whose diethyl ester is used in syntheses of vitamins B1 and B6, barbiturates, and numerous other valuable compounds.
Malonic acid itself is rather unstable and has few applications. 
Malonic acids calcium salt occurs in beetroot, but the acid Malonic acidself is usually prepared by hydrolyzing diethyl malonate. 
Malonic acid undergoes the usual reactions of carboxylic acids as well as facile cleavage into acetic acid and carbon dioxide.
Diethyl malonate, CH2(CO2C2H5)2, also called malonic ester, is prepared by the reaction of ethyl alcohol with cyanoacetic acid. 
Malonic acids utility in synthesis arises from the reactivity of Malonic acids methylene (CH2) group; a hydrogen atom is easily removed by sodium ethoxide or other strong base, and the resulting derivative reacts readily with an alkyl halide to form a diethyl alkylmalonate. 
A second alkyl group may be similarly introduced. 
The diethyl dialkylmalonates are converted by reaction with urea to barbiturates. 
Diethyl malonate is a colourless, fragrant liquid boiling at 181.4° C.

Applications
Malonic acid is a precursor to specialty polyesters. 
Malonic acid can be converted into 1,3-propanediol for use in polyesters and polymers and a projected market size of $621.2 million by 2021.
Malonic acid can also be a component in alkyd resins, which are used in a number of coatings applications for protecting against damage caused by UV light, oxidation, and corrosion. 
One application of malonic acid is in the coatings industry as a crosslinker for low-temperature cure powder coatings, which are becoming increasingly valuable for heat sensitive substrates and a desire to speed up the coatings process.
The global coatings market for automobiles was estimated to be $18.59 billion in 2014 with projected combined annual growth rate of 5.1% through 2022.
Malonic acid is used in a number of manufacturing processes as a high value specialty chemical including the electronics industry, flavors and fragrances industry, specialty solvents, polymer crosslinking, and pharmaceutical industry. 
In 2004, annual global production of malonic acid and related diesters was over 20,000 metric tons.

Potential growth of these markets could result from advances in industrial biotechnology that seeks to displace petroleum-based chemicals in industrial applications.
Malonic acid was listed as one of the top 30 chemicals to be produced from biomass by the US Department of Energy.
In food and drug applications, malonic acid can be used to control acidity, either as an excipient in pharmaceutical formulation or natural preservative additive for foods.
Malonic acid is used as a building block chemical to produce numerous valuable compounds, including the flavor and fragrance compounds gamma-nonalactone, cinnamic acid, and the pharmaceutical compound valproate.
Malonic acid (up to 37.5% w/w) has been used to cross-link corn and potato starches to produce a biodegradable thermoplastic; the process is performed in water using non-toxic catalysts.
Starch-based polymers comprised 38% of the global biodegradable polymers market in 2014 with food packaging, foam packaging, and compost bags as the largest end-use segments.
Eastman Kodak company and others use malonic acid and derivatives as a surgical adhesive.

General description
Malonic acid (MA), also known as propanedioic acid, is a dicarboxylic acid. 
The crystals of MA are triclinic at room temperature. 
The oxidation of malonic acid by cerium (IV) in sulfuric acid solution has been studied. 
The reaction kinetics of the photocatalytic decomposition of MA in aqueous suspensions of titanium dioxide (TiO2) have been described.
The malonic acid Lewis structure has been found by the X-ray crystallography method. 
The malonic acid structure CH2(COOH)2 has two carboxylic acids. 
The salts and esters of malonic acid (malonates) have structures similar to malonic acid.    

Applications of Malonic Acid
Diethyl malonate, CH2 (CO2C2H5)2, also called malonic ester, is prepared by the reaction of ethyl alcohol with cyanoacetic acid. 
Malonic acids utility in synthesis arises from the reactivity of Malonic acids methylene (CH2) group; a hydrogen atom is easily removed by sodium ethoxide or other strong base, and the resulting derivative reacts readily with an alkyl halide to form a diethyl alkylmalonate.

Malonic Acid Uses
Malonic acid acts as a precursor for conversion to 1,3-propanediol, which is a compound used in polyesters and polymers with the huge market size.
Malonic acid is used for the preparation of cinnamic acid, a compound used for the formation of cin metacin which is an anti-inflammatory. 
The malonates are used in syntheses of B1 and B6, barbiturates, and several other valuable compounds. 
Malonic acid is used in cosmetics as a buffering and as a flavouring agent in food.
Malonic acid is used as a component of alkyd resins, used in coating applications to protect from UV rays, oxidation, and corrosion.
Malonic acid is a building block to many valuable compounds in food and drug applications, pharmaceutical, electronics industry, fragrances, specialty polymer, specialty solvents, and many more.   

Malonic acid Application
Malonic acid may be used as a cross-linking agent between corn starch and potato starch to improve Malonic acids mechanical properties.

Sometimes alternatively referred to as propanedioic acid, malonic acid is a dicarboxylic acid of ethane with a methylene group separating the two carbonyl moieties. 
Malonic acid occurs in small quantities naturally in urine and beetroot, but is typically prepared by hydrolyzing diethyl malonate.

Molecular Weight：104.06146
Introduction: 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 Malonic acids esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. 
The name originates from the Greek word (malon) meaning 'apple'.

Malonic acid half-oxyesters (MAHOs) and malonic acid half-thioesters (MAHTs) can be converted to ester or thioester enolates, respectively, by decarboxylation under mild reaction conditions, avoiding the use of either strong bases or Lewis acids and thus increasing the environmental compatibility of the transformation.
Sylvie Condon, Marc Presset, and colleagues, Université Paris Est Créteil, CNRS, ICMPE, Thiais, France, have developed a new route for the preparation of β2,3-aminoesters involving an organocatalyzed decarboxylative Mannich reaction. 
The team began by the optimization of the decarboxylative Mannich reaction between tosyl imines and substituted malonic acids half-oxyesters (SMAHOs).
The tertiary amine, 1,4-diazabicyclo[2.2.2]octane (DABCO), was used as catalyst, and tetrahydrofuran (THF) as solvent. 
The reaction proceeds under simple reaction conditions and tolerates a broad range of substrates, affording general access to aminoesters, the syn diastereomer being the major one. 
An alternative multicomponent protocol has also been developed to increase the overall eco-compatibility of the process.

Definition
Malonic Acid (or C3H4O4) is a white crystalline acid derived from malic acid and used in making barbiturates. 
Malonic acid is also called Propanedioic Acid, (HO2CCH2CO2H), and a dibasic organic acid whose diethyl ester is used in syntheses of vitamins B1 and B6, barbiturates, and numerous other valuable compounds.

The ionized form of malonic acid, as well as Malonic acids 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’.
Malonic Acid itself is rather unstable and has few applications. 
Malonic acids calcium salt occurs in beetroot, but the acid itself is usually prepared by hydrolyzing diethyl malonate. 
Malonic acid undergoes the usual reactions of carboxylic acids as well as facile cleavage into acetic acid and carbon dioxide. 
Malonic acid is often mistakenly believed to occur in beetroot at high concentration, and a study on the composition of sugar beet liquors revealed no malonic acid. 
Malonic acid exists in its normal state as white crystals.

Application Notes
Malonic acid is used to prepare barbiturates. 
Malonic acids derivative diethylmalonate is used in Knoevenagel condensation reactions as well as reacts with acetone to form Meldrum's acid. 
Malonic acid is used to control acidity, preservative additive for foods and as an excipient in pharmaceutical formulation. 
Malonic acid acts as a precursor to polyesters and as an active component in alkyd resins. 
Further, Malonic acid is used as a building block in chemical synthesis. 
In addition to this, Malonic acid is used to prepare starch-based resin.

Malonic acid is a normal component of human urine, in small quantities, but a genetic disorder called methyl malonic aciduria (also known as malonic aciduria) causes high levels of methyl malonic acid in the blood serum and urine. 
Patients with this disorder suffer from severe metabolic acidosis and a metabolic block in the vitamin B12 dependent conversion of propionyl CoA to succinyl CoA. 
In infants, symptoms can include developmental delay, cardiomyopathy, mental retardation, and in its more severe forms, neonatal death.

History
Malonic acid is a naturally occurring substance found in many fruits and vegetables.
There is a suggestion that citrus fruits produced in organic farming contain higher levels of malonic acid than fruits produced in conventional agriculture.
Malonic acid was first prepared in 1858 by the French chemist Victor Dessaignes via the oxidation of malic acid.

Structure and preparation
The structure has been determined by X-ray crystallography and extensive property data including for condensed phase thermochemistry are available from the National Institute of Standards and Technology.

Sodium carbonate generates the sodium salt, which is then reacted with sodium cyanide to provide the sodium salt of cyanoacetic acid via a nucleophilic substitution. 
The nitrile group can be hydrolyzed with sodium hydroxide to sodium malonate, and acidification affords malonic acid. 
Industrially, however, malonic acid is produced by hydrolysis of dimethyl malonate or diethyl malonate.
Malonic acid has also been produced through fermentation of glucose.

Organic reactions
Malonic acid reacts as a typical carboxylic acid: forming amide, ester, anhydride, and chloride derivatives.
Malonic anhydride can be used as an intermediate to mono-ester or amide derivatives, while malonyl chloride is most useful to obtain diesters or diamides. 
In a well-known reaction, malonic acid condenses with urea to form barbituric acid. 
Malonic acid may also condensed be with acetone to form Meldrum's acid, a versatile intermediate in further transformations. 
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.

Malonic acid is a dicarboxylic acid with a chemical formula C3H4O4. 
Dicarboxylic acids are organic compounds containing two carboxylic acid functional groups. 
Dicarboxylic acids generally show the same chemical behaviour and reactivity as monocarboxylic acids. 
Malonic acid is a substance found in some fruits that occurs naturally. 
Fruits generated in organic farming contain greater concentrations of malonic acid in citrus compared to fruits generated in conventional farming.

The systematic name for malonic acid IUPAC is propanedioic acid. 
Malonic acid is the archetypal instance of a competitive inhibitor: Malonic acid functions in the respiratory electron transport chain against succinate dehydrogenase. 
Malonic acid is correlated with deficiency of malonyl-CoA decarboxylase, an inborn metabolism mistake.

Malonic acid is a naturally occurring substance found in many fruits and vegetables.
There is a suggestion that citrus fruits produced in organic farming contain higher levels of malonic acid than fruits produced in conventional agriculture.
Malonic acid was first prepared in 1858 by the French chemist Victor Dessaignes via the oxidation of malic acid.

Malonic acid is the archetypal example of a competitive inhibitor: Malonic acid acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain. 
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. 
Malonic acid is also known to be a competitive inhibitor of succinic dehydrogenase, the enzyme responsible for the dehydrogenation of succinate within Krebs cycle.
Malonic acid and its esters are characterized by the large number of condensation products. 
They are important intermediates in syntheses of vitamins B1 and B6, barbiturates, non-steroidal anti-inflammatory agents, other numerous pharmaceuticals, agrochemicals and flavors & fragrances compounds.

Synomys:
malonic acid
propanedioic acid
141-82-2
Dicarboxymethane
Carboxyacetic acid
Methanedicarboxylic acid
Kyselina malonova
USAF EK-695
Dicarboxylate
Dicarboxylic acid
MFCD00002707
UNII-9KX7ZMG0MK
NSC 8124
Methanedicarbonic acid
Malonic acid, 99%
Thallium malonate
AI3-15375
1,3-propanedioic acid
141-82-2 [RN]
1751370 [Beilstein]
212-385-4 [EINECS]
Malonic acid
Methanedicarbonic acid
MFCD00002707 [MDL number]
Propanedioic acid
118690-08-7 [RN]
3-HYDROXY-PROPANOIC ACID
Benzophenone-1-hydroxy cyclohexyl phenyl ketone mixture
Carboxyacetic acid
CH2(COOH)2 [Formula]
dicarboxylic acid
DICARBOXYLIC ACID C3
dicarboxymethane
DXX
HOOC-CH2-COOH [Formula]
hydrogen malonate
Malonate dicarboxylic acid
Malonic acid|Propanedioic acid
Metahnedicarboxylic acid
Methanedicarboxylic acid
Methylmalonic acid
MLA
MLI
propandioic acid
Propane-1,3-dioic acid
Propanediolic acid
QV1VQ [WLN]
STR00614
WLN: QV1VQ
α,ω-dicarboxylic acid
Propane-1,3-dioic acid
9KX7ZMG0MK
alpha,omega-Dicarboxylic acid
CHEBI:30794
NSC8124
1,3-Propanoic acid
Malonicacid
PROPANEDIOLIC ACID
METAHNEDICARBOXYLIC ACID
1,3-Propanedioic acid
EINECS 205-503-0
BRN 1751370
propanedioicacid
C3H4O4
H2malo
2fah
malonic acid group
Malonic acid (8CI)
1o4m
ACMC-1BSLG
HOOC-CH2-COOH
MLI
C3-120-beta-polymorph
C3-140-beta-polymorph
C3-180-beta-polymorph
C3-220-beta-polymorph
C3-260-beta-polymorph
C3-298-beta-polymorph
Malonate dicarboxylic acid
Propanedioic acid (9CI)
DSSTox_CID_1659
SCHEMBL336
WLN: QV1VQ
CH2(COOH)2
CHEMBL7942
DSSTox_RID_76271
Malonic acid, Reagent Grade
DSSTox_GSID_21659
4-02-00-01874 (Beilstein Handbook Reference)
SCHEMBL1471092
DTXSID7021659
OC(=O)[C]C(O)=O
BDBM14673
HSDB 8437
Propanedioic acid dithallium salt
Malonic acid, analytical standard
ZINC895212
ACN-S002266
AMY11201
BCP05571
NSC-8124
STR00614
Tox21_200534
ANW-20648
BBL019770
LMFA01170041
s3029
SBB040552
STL194278
Malonic acid, ReagentPlus(R), 99%
AKOS000119034
CS-W019962
DB02175
MCULE-5893043131
MP-2177
PROPANEDIOIC ACID MALONIC ACID
NCGC00248681-01
NCGC00258088-01
AK-98172
BP-11453
CAS-141-82-2
SY001875
DB-081008
DB-088240
Malonic acid, SAJ first grade, >=99.0%
FT-0628127
FT-0628128
FT-0690260
FT-0693474
M0028
ST50213926
Malonic acid, Vetec(TM) reagent grade, 98%
C00383
C02028
C04025
Q421972
J-521669
Z57965450
F1908-0177
Malonic acid, certified reference material, TraceCERT(R)
592A9849-68C3-4635-AA3D-CBC44965EA3A
Malonic acid, sublimed grade, >=99.95% trace metals basis
DICARBOXYLIC ACID C3; PROPANEDIOLIC ACID; METHANEDICARBOXYLIC ACID
Malonic acid, anhydrous, free-flowing, Redi-Dri(TM), ReagentPlus(R), 99%
87205-08-1
LML