PRODUCTS

MALONIC ACID

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 is used in flavours as well as in the fragrance industry.

CAS Number: 141-82-2
EC Number: 205-503-0
MDL Number: MFCD00002707
Molecular Formula: C3H4O4 / COOHCH2COOH

SYNONYMS:
PROPANEDIOIC ACID, MAAC, Daucic acid, CH2(COOH)2, Methane acid, Propandioic acid, Methanedicarbonic acid, METHANEDICARBOXYLIC ACID, MALONIC ACID, 99%MALONIC ACID, 99%MALONIC ACID, 99%MALONIC ACID, 99%, Malonsure, malonic acid, propanedioic acid, 141-82-2, Dicarboxymethane, Carboxyacetic acid, Methanedicarboxylic acid, malonate, USAF EK-695, 1,3-Propanedioic acid, Dicarboxylate, Malonicacid, Dicarboxylic acid, NSC 8124, UNII-9KX7ZMG0MK, 9KX7ZMG0MK, AI3-15375, H2malo, EINECS 205-503-0, MFCD00002707, BRN 1751370, Methanedicarbonic acid, CHEBI:30794, Thallium malonate, HOOC-CH2-COOH, NSC-8124, Propane-1,3-dioic acid, alpha,omega-Dicarboxylic acid, DTXSID7021659, HSDB 8437, NSC8124, 4-02-00-01874 (Beilstein Handbook Reference), 1,3-Propanoic acid, PROPANEDIOLIC ACID, METAHNEDICARBOXYLIC ACID, 2fah, MLI, Malonic acid, 99%, Malonic acid (8CI), 1o4m, Malonate dicarboxylic acid, Malonic acid, 99.5%, Propanedioic acid (9CI), SCHEMBL336, WLN: QV1VQ, MALONIC ACID [MI], CH2(COOH)2, CHEMBL7942, MALONIC ACID [INCI], DTXCID401659, SCHEMBL1471092, BDBM14673, Propanedioic acid dithallium salt, Malonic acid, analytical standard, AMY11201, BCP05571, STR00614, Tox21_200534, AC8295, LMFA01170041, s3029, Malonic acid, ReagentPlus(R), 99% AKOS000119034, CS-W019962, DB02175, PROPANEDIOIC ACID, MALONIC ACID, NCGC00248681-01, NCGC00258088-01, BP-11453, CAS-141-82-2, SY001875, Malonic acid, SAJ first grade, >=99.0%, FT-0628127, FT-0628128, FT-0690260, FT-0693474, M0028, NS00013842, EN300-18457, 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, InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7), Malonic acid, anhydrous, free-flowing, Redi-Dri(TM), ReagentPlus(R), 99%, LML, malonic acid, propanedioic acid, 141-82-2, Dicarboxymethane, Carboxyacetic acid, Methanedicarboxylic acid, malonate, Kyselina malonova, USAF EK-695, 1,3-Propanedioic acid, Dicarboxylic acid, Kyselina malonova [Czech], NSC 8124, MFCD00002707, UNII-9KX7ZMG0MK, 9KX7ZMG0MK, AI3-15375, H2malo, EINECS 205-503-0, BRN 1751370, Methanedicarbonic acid, CHEBI:30794, Thallium malonate, HOOC-CH2-COOH, NSC-8124, Propane-1,3-dioic acid, Malonicacid, alpha,omega-Dicarboxylic acid, DTXSID7021659, HSDB 8437, NSC8124, 4-02-00-01874 (Beilstein Handbook Reference), 1,3-Propanoic acid, PROPANEDIOLIC ACID, METAHNEDICARBOXYLIC ACID, 2fah, MLI, Malonic acid, 99%, Malonic acid (8CI), 1o4m, 63524-05-0, Malonate dicarboxylic acid, Malonic acid, 99.5%, Propanedioic acid (9CI), SCHEMBL336, WLN: QV1VQ, MALONIC ACID [MI], CH2(COOH)2, CHEMBL7942, DTXCID401659, SCHEMBL1471092, BDBM14673, Propanedioic acid dithallium salt, Malonic acid, analytical standard, BCP05571, STR00614, Tox21_200534, AC8295, LMFA01170041, s3029, STL194278, Malonic acid, ReagentPlus(R), 99%, AKOS000119034, CS-W019962, DB02175, PROPANEDIOIC ACID MALONIC ACID, NCGC00248681-01, NCGC00258088-01, BP-11453, CAS-141-82-2, SY001875, DB-081008, DB-088240, Malonic acid, SAJ first grade, >=99.0%, M0028, NS00013842, EN300-18457, Malonic acid, Vetec(TM) reagent grade, 98%, C00383, C02028, C04025, Q421972, 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, InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7, Malonic acid, anhydrous, free-flowing, Redi-Dri(TM), ReagentPlus(R), 99%, 87205-08-1, LML

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.
Malonic acid is a naturally occurring substance found in many fruits and vegetables.

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.

Malonic acid (IUPAC systematic name: propanedioic acid ) is a dicarboxylic acid with structure CH 2 (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
Malonic acid is a dicarboxylic acid belonging to the family of carboxylic acids.

A dicarboxylic acid contains two carboxylic acid functional groups. Usually, a dicarboxylic acid exhibits the same chemical behavior as monocarboxylic acids.
This naturally occurs in certain fruits.

Malonic Acid is a useful organic compound with various benefits.
Malonic Acid's IUPAC name is propanedioic acid.
Malonic Acid should not be confused with malic or maleic acid.

Malonic acid is also known as Propanedioic acid or Dicarboxymethane.
The name is derived from the Greek word Malon which means apple.
Malonate is the ionized form of malonic acid, along with its esters and salt.

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 fruits viz citrus fruits.
Malonic acid can be produced through the fermentation of glucose.
Malonic acid is a dicarboxylic acid with the 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 IUPAC name of malonic acid is propanedioic acid.
Malonic acid is the archetypal instance of a competitive inhibitor: it 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 (MA), also known as propanedioic acid, is a dicarboxylic acid with structure CH2(COOH)2.
Malonic Acid have three kinds of crystal forms, of which two are triclinic, and one is monoclinic.

That crystallized from ethanol is white triclinic crystals.
Malonic Acid decomposes to acetic acid and carbon dioxide at 140℃.
Malonic Acid does not decompose at 1.067×103~1.333×103Pa vacuum, but directly sublimates.

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 Latin malum, meaning apple.

Malonic acid is an alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.
Malonic Acid has a role as a human metabolite.
Malonic Acid is a conjugate acid of a malonate(1-).

Malonic Acid is a white crystals or crystalline powder.
Malonic Acid sublimes in vacuum.
Malonic Acid is water soluble.

Malonic acid appears as white crystals or crystalline powder.
Malonic Acid sublimes in vacuum.
Malonic acid is an alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.

Malonic Acid has a role as a human metabolite.
Malonic Acid is a conjugate acid of a malonate(1-).
Malonic acid has been reported in Camellia sinensis, Meum athamanticum, and other organisms with data available.

Malonic Acid is soluble in cold water.
Malonic Acid is incompatible with bases, oxidizing agents and reducing agents.
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'.

USES and APPLICATIONS of MALONIC ACID:
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 is used to control 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 finds application across various industries, including automobiles, food, fragrance, and pharmaceuticals.

Malonic Acid is used as a precursor in polyester and other polymers.
Malonic Acid is used as a flavoring agent in the fragrance industry.
Malonic Acid is suitable for controlling acidity.

Malonic Acid finds usage in pharmaceutical products.
Malonic Acid is used in the manufacture of biodegradable containers.
Malonic Acid is also a component of surgical adhesives.

Malonic Acid serves as a cross-linking agent between cornstarch and potato starch to enhance its properties.
Malonic Acid is used for the preparation of barbituric salt
Malonic Acid is used in electroplating.

Malonic Acid is used in the production of vitamins– B1, B6, B2, and amino acids.
Malonic Acid can also be used as a component in alkyd resins.
Malonic Acid is widely used in several coating applications to protect objects against UV light damage, oxidation, and corrosion.

A common application of malonic acid is as a crosslinker for low-temperature powder coatings.
These are valuable for heat-sensitive substrates.
It is on the US Department of Energy’s list of top chemicals for biomass production.

In food and drug applications, Malonic Acid acts as a natural preservative additive for foods.
Its therapeutic uses include the prevention of resorption of bone tissue in broiler chicks by adding malonic acid to feed.
Malonic acid is used as a precursor in polymers and polyester.

Malonic Acid is used in flavours as well as in the fragrance industry.
Malonic Acid is used to control 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 is used as an intermediate in the manufacture of barbiturates and other pharmaceuticals.

Malonic Acid is a component used as a stabilizer in many high-end cosmetic and pharmaceutical products.
Malonic acid is also used as a building block in chemical synthesis, specifically to introduce the molecular group -CH2-COOH.
Malonic Acid is used for the introduction of an acetic acid moiety under mild conditions by Knoevenagel condensation and subsequent decarboxylation.

Malonic acid acts as a building block in organic synthesis.
Malonic Acid is also useful as a precursor for polyesters and alkyd resins, which are used in coating applications, thereby protecting against UV light, corrosion and oxidation.

Malonic Acid acts as a cross linker in the coating industry and surgical adhesive.
Malonic Acid finds application in the production of specialty chemicals, flavors and fragrances, polymer cross linkers and pharmaceuticals.
Malonic acid is a precursor to specialty polyesters.

Malonic Acid can be converted into 1,3-propanediol for use in polyesters and polymers (whose usefulness is unclear though).
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.
In 2004, malonic acid was listed by the US Department of Energy as one of the top 30 chemicals to be produced from biomass.

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.

Malonic acid is acts as a building block in organic synthesis.
Malonic Acid is also useful as a precursor for polyesters and alkyd resins, which is used in coating applications, thereby protecting against UV light, corrosion and oxidation.

-Biotechnological Applications of Malonic Acid:
The calcium salt of malonic acid occurs in high concentrations in beetroot.
Malonic Acid exists in its normal state as white crystals.

Malonic acid is the classic example of a competitive inhibitor: Malonic Acid acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.

OCCURRENCE OF MALONIC ACID:
Malonic Acid is an organic compound naturally found in some fruits.
Fruits produced in organic farming have greater concentrations of malonic acid than those generated from conventional farming practices.

Malonic Acid is often found in some citrus fruits and vegetables.
Malonic Acid is a component of food items, it is present in animals, including humans.

The name of this acid is derived from the Greek word Malon.
It means apple.

The ionized form of malonic acid is malonate, along with its salts and esters.
Malonic Acid occurs as a white crystal or crystalline powder in nature.

Did you Know:
Several food substances contain malonic acid, including:
● Red beetroots
● Corns
● Common beets
● Scarlet beans
● Cow’s milk
Its occurrence in food items makes malonic acid a potential biomarker indicating the consumption of these foods.

HISTORY OF MALONIC ACID:
In 1858, it was prepared for the first time by a French chemist –Victor Dessaignes.
He oxidized malic acid with potassium dichromate, which is a strong oxidizing agent.

Later Malonic Acid was found to occur in some fruits viz citrus fruits.
Malonic Acid can also be produced by fermenting glucose.

SIGNIFICANCE OF MALONIC ACID:
Malonic Acid is an example of a competitive inhibitor.
Malonic Acid functions in the ETS chain against succinate dehydrogenase in respiration.

Malonic Acid is related to a deficiency of malonyl-CoA decarboxylase that leads to an inborn metabolism mistake.
It serves as a potential biomarker for tracking foods that contain malonic acids.
Malonic Acid finds usage in various industries.

FORMULA OF MALONIC ACID:
The malonic acid formula is C3H4O4.
Malonic Acid is also called propanedioic acid or dicarboxymethane, and the formula is written as CH₂(COOH)₂.

SALTS AND ESTERS OF MALONIC ACID:
Malonic acid is diprotic; that is, it can donate two protons per molecule.
Malonic Acid's first pKa is 2.8 and the second is 5.7.
Thus the malonate ion can be HOOCCH2COO− or CH2(COO)2−2.

Malonate or propanedioate compounds include salts and esters of malonic acid, such as
*Diethyl malonate
*Dimethyl malonate
*Disodium malonate
*Malonyl-CoA

REACTIOS OF MALONIC ACID:
Malonic acid reacts as a typical carboxylic acid forming amide, ester, 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 be condensed 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.

*Briggs–Rauscher reaction
Malonic acid is a key component in the Briggs–Rauscher reaction, the classic example of an oscillating chemical reaction.

*Knoevenagel condensation
Malonic acid is used to prepare a,b-unsaturated carboxylic acids by condensation and decarboxylation.
Cinnamic acids are prepared in this way:

CH2(CO2H)2 + ArCHO → ArCH=CHCO2H + H2O + CO2
In this, the so-called Knoevenagel condensation, malonic acid condenses with the carbonyl group of an aldehyde or ketone, followed by a decarboxylation.
When malonic acid is condensed in hot pyridine, the condensation is accompanied by decarboxylation, the so-called Doebner modification.

PREPARATION OF MALONIC ACID:
Malonic acid does not readily form an anhydride, dehydration gives carbon suboxide instead:
CH2(CO2H)2 → O=C=C=C=O + 2 H2O

The transformation is achieved by warming a dry mixture of phosphorus pentoxide (P4O10) and malonic acid.
Malonic Acid reacts in a similar way to malonic anhydride, forming malonates.

HISTORY OF MALONIC ACID:
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.

Hermann Kolbe and Hugo Müller independently discovered how to synthesize malonic acid from propionic acid, and decided to publish their results back-to-back in the Chemical Society journal in 1864.
This led to priority dispute with Hans Hübner and Maxwell Simpson who had independently published preliminary results on related reactions.

STRUCTURE AND PREPARATION OF MALONIC ACID:
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.
A classical preparation of malonic acid starts from chloroacetic acid

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.
It has also been produced through fermentation of glucose.

RELATED COMPOUNDS OF MALONIC ACID:
-Other anions
Malonate

-Related carboxylic acids
Oxalic acid
Propionic acid
Succinic acid
Fumaric acid

-Related compounds
Malondialdehyde
Dimethyl malonate

CHEMICAL PROPERTIES OF MALONIC ACID:
Malonic acid is a white crystalline solid that decomposes at approximately 135°C.
Malonic Acid has high solubility in water and oxygenated solvents and exhibits greater acidity than acetic acid, which has a pK value of 4.75.

The pKa values for the loss of its first and second protons are 2.83 and 5.69, respectively.
Malonic Acid is slightly soluble in pyridine.

Malonic Acid can decompose to formic acid and carbon dioxide in case of potassium permanganate.
Since that malonic acid generates carbon dioxide and water after heated without pollution problems, it can be directly used as aluminum surface treatment agent.

REACTIVITY POFILE OF MALONIC ACID:
Malonic acid is a carboxylic acid.
Carboxylic acids donate hydrogen ions if a base is present to accept them.

They react in this way with all bases, both organic (for example, the amines) and inorganic.
Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat.

Neutralization between an acid and a base produces water plus a salt.
Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water.

Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions.
The pH of solutions of carboxylic acids is therefore less than 7.0.

Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt.
Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt.

Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.
Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Malonic acid to corrode or dissolve iron, steel, and aluminum parts and containers.

Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide.
The reaction is slower for dry, solid carboxylic acids.

Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide.
Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides.

Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.
Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat.

Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents.
These reactions generate heat.
A wide variety of products is possible.

Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions Malonic acid is incompatible with strong oxidizers.
Malonic acid is also incompatible with bases and reducing agents.

BIOLOGICAL FUNCTIONS OF MALONIC ACID:
Malonic acid is the classic example of a competitive inhibitor of the enzyme succinate dehydrogenase (complex II), in the respiratory electron transport chain.

Malonic Acid binds to the active site of the enzyme without reacting, competing with the usual substrate succinate but lacking the CH2CH2 group required for dehydrogenation.
This observation was used to deduce the structure of the active site in succinate dehydrogenase.

SYNTHESIS OF MALONIC ACID:
Preparation of malonic acid starts with chloroacetic acid which is also known as MCA (monochloroacetic acid).

Step 1: Sodium carbonate produces sodium salt.
Step 2: It is made to react with sodium cyanide.
Step 3: cyanoacetic acid salt is generated through nucleophilic substitution.
Step 4: The nitrile group is hydrolyzed with sodium hydroxide to produce sodium malonate.
Step 5: The acidification results in malonic acid.

Industrially, malonic acid is produced by the hydrolysis of diethyl malonate or dimethyl malonate.
Malonic acid is a forerunner to polyester specialities.
Malonic acid is used to generate countless useful compounds as a construction block chemical.

REACTION OF MALONIC ACID:
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.

IUPAC NAME OF MALONIC ACID:
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’.

The IUPAC name of malonic acid is Propanedioic acid.
Methane Dicarboxylic acid is another name for malonic acid.
The ester and salts of malonic acid are called malonates.

Malonic 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.

STRUCTURAL FORMULA OF MALONIC ACID:
The structural formula of malonic acid can be given as
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.

PREPARATION OF MALONIC ACID:
Malonic acid is usually produced from chloroacetic acid.

Reaction:
The chloroacetic acid is added to the reaction kettle by adding sodium carbonate aqueous solution to generate sodium chloroacetate aqueous solution, and then 30% sodium cyanide solution is slowly added dropwise, and the reaction is carried out at a predetermined temperature to generate sodium cyanoacetate.

After the cyanation reaction is completed, add sodium hydroxide for heating and hydrolysis to generate sodium malonate solution, concentrate, then dropwise add sulfuric acid for acidification to generate malonic acid, filter and dry to obtain the product.

This method often does not produce a pure enough product or the pure product has an extremely low yield.
Industrially, malonic acid is also produced by hydrolyzing dimethyl malonate or diethyl malonate.

This manufacturing method is able to bring about a higher yield and purity, but the organic synthesis of malonic acid through these processes is extremely costly and environmentally hazardous.

PROPERTIES OF MALONIC ACID:
Malonic acid molecular weight: 104.061 g.mol-1
The density of malonic acid is 1.619 g/cm3.

Malonic Acid appears as a crystalline powder that is white or colourless.
At the boiling point above 140oC the compound decomposes.

The melting point is 135-137o C.
If heated to decomposition under fire Malonic Acid emits carbon oxide fumes and acrid irritating smoke.

Acidity pKa = 2.85 at 25oC. pKa1 = 2.83, pKa2 = 5.69
The molar heat of combustion is 864 kJ/mol.

The heat of vaporization is 92 kJ/mol.
Malonic Acid is soluble in water.

Solubility 763 g/L.
Malonic Acid has a white crystal or crystalline powder structure.

Malonic Acid is naturally occurring and can be found in many vegetables, fruits.
Malonic Acid compound was first prepared by Victor Dessaignes by the oxidation reaction of malic acid.

PHYSICAL PROPERTIES OF MALONIC ACID:
Solubility: Dissolves in alcohol, pyridine, and ether.
Molecular Wt/ Molar Mass: 104.06 g/mol

Density: 1.619 g/cm³
Boiling Point: Decomposes

Melting Point: 135 to 137°C
Nature: Acidic

Color: White
Stability: Usually stable under recommended conditions

Molar heat of combustion: 864 kJ/mol
The heat of vaporization: 92 kJ/mol

Malonic Acid does not have a chiral center.
So, Malonic Acid doesn’t exhibit optical isomerism.

Malonic Acid is a hygroscopic solid that sublimes in a vacuum.
Calculation of Molecular Weight of Malonic Acid

The formula of malonic acid is C3H4O4.
The atomic weight of carbon is 12.011.

The atomic weight of oxygen is 15.999.
The atomic weight of hydrogen is 1.00784.

So, its molar mass can be calculated as follows:
= (3 × 12.011) + (4 × 1.00784) + (4 × 15.999)
= 36.033 + 4. 03136 + 63.996
= 104.06 grams/ mol
Thus, the molar mass or molecular weight of malonic acid is 104.061 g/mol.

CHEMICAL PROPERTIES OF MALONIC ACID:
The chemical properties of malonic acid are as follows:

*On Heating
When It is heated, Malonic Acid gives acetic acid and carbon dioxide.

*Reaction with Phosphorus Pentoxide
On heating a dry mixture of malonic acid and phosphorus pentoxide, carbon suboxide is prepared.

*Organic Reactions
Malonic acid reactions are usually similar to a typical carboxylic acid.
Malonic Acid forms amide, anhydrides, esters, and chloride derivatives on reacting with specific reactants.

Malonic anhydride serves as an intermediate in the formation of amide derivatives.
Malonyl chloride is widely used for obtaining diamides or diesters.
Some of the popular organic reactions involving malonic acid are as follows:

*It condenses with urea to give barbituric acid.
Malonic acid also condenses with acetone to produce Meldrum’s acid.
Malonic Acid is a versatile intermediate and helps in further transformations.

Malonate’s coenzyme A derivative— malonyl-CoA, acts as an important precursor in fatty acid biosynthesis.
It is formed from acetyl CoA when it is acted upon by acetyl-CoA carboxylase.
The malonate gets transferred to an acyl carrier protein for its addition to the fatty acid chain.

*Briggs–Rauscher Reaction
A popular name reaction has malonic acid as its key component.
Malonic Acid is an example of an oscillating chemical reaction.

*Knoevenagel Condensation
The reaction is a modification of the aldol condensation reaction (the reaction between benzaldehyde and acetophenone).
It involves the interaction of malonic acid or its diesters with the carbonyl group of a ketone or an aldehyde.
This process is followed by a dehydration reaction.

PREPARATION OF MALONIC ACID:
Malonic Acid can be prepared with chloroacetic acid (also called mono chloroacetic acid).
Sodium carbonate gives sodium salt.
The salt reacts with sodium cyanide.

Nucleophilic substitution reaction gives rise to cyanoacetic acid salt.
The nitrile group is hydrolyzed with NaOH to produce sodium malonate.
The acidification of sodium malonate gives malonic acid.

PURIFICATION METHODS OF MALONIC ACID:
Crystallise malonic acid from *benzene/diethyl ether (1:1) containing 5% of pet ether (b 60-80o), wash with diethyl ether, then recrystallise it from H2O or acetone.
Dry Malonic Acid under vacuum over conc H2SO4

PATHOLOGY OF MALONIC ACID:
If elevated malonic acid levels are accompanied by elevated methylmalonic acid levels, this may indicate the metabolic disease combined malonic and methylmalonic aciduria (CMAMMA).
By calculating the malonic acid to methylmalonic acid ratio in blood plasma, CMAMMA can be distinguished from classic methylmalonic academia

BIOCHEMISTRY OF MALONIC ACID:
Malonic acid is the precursor in mitochondrial fatty acid synthesis (mtFASII), in which it is converted to malonyl-CoA by acyl-CoA synthetase family member 3 (ACSF3).

Additionally, the coenzyme A derivative of malonate, malonyl-CoA, is an important precursor in cytosolic fatty acid biosynthesis along with acetyl CoA.
Malonyl CoA is formed there 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 the classic example of a competitive inhibitor of the enzyme succinate dehydrogenase (complex II), in the respiratory electron transport chain.

Malonic Acid binds to the active site of the enzyme without reacting, competing with the usual substrate succinate but lacking the −CH2CH2− group required for dehydrogenation.
This observation was used to deduce the structure of the active site in succinate dehydrogenase.

Inhibition of this enzyme decreases cellular respiration.
Since malonic acid is a natural component of many foods, it is present in mammals including humans.

PHYSICAL and CHEMICAL PROPERTIES of MALONIC ACID:
Physical Appearance: A solid
Storage: Store at -20°C
M.Wt: 104.06
Cas No.: 141-82-2
Formula: C3H4O4
Solubility: ≥10.4 mg/mL in DMSO; ≥104 mg/mL in H2O; ≥119.8 mg/mL in EtOH
Chemical Name: malonic acid
Canonical SMILES: O=C(O)CC(O)=O
Shipping Condition: Small Molecules with Blue Ice,
Modified Nucleotides with Dry Ice.
CAS Number: 141-82-2
Molecular Weight: 104.06
Beilstein: 1751370
MDL number: MFCD00002707

Molecular Weight: 104.06 g/mol
XLogP3: -0.8
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 2
Exact Mass: 104.01095860 g/mol
Monoisotopic Mass: 104.01095860 g/mol
Topological Polar Surface Area: 74.6Å²
Heavy Atom Count: 7
Formal Charge: 0
Complexity: 83.1
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0

Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Physical state: powder
Color: white
Odor: odorless
Melting point/freezing point:
Melting point: >= 135 °C
Initial boiling point and boiling range: 215 °C at 18,66 hPa (decomposition)

Flammability (solid, gas): The product is not flammable.
Upper/lower flammability or explosive limits: No data available
Flash point: 157 °C - c.c.
Autoignition temperature: No data available
Decomposition temperature: > 140 °C
pH: No data available
Viscosity
Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Water solubility 766 g/l at 20 °C
Partition coefficient:
n-octanol/water:
log Pow: -0,81 - Bioaccumulation is not expected.

Vapor pressure: 0,002 hPa at 25 °C
Density: 1,6 g/cm3
Relative density: 1,03 at 20 °C
Relative vapor density: No data available
Particle characteristics: No data available
Explosive properties: No data available
Oxidizing properties: none
Other safety information: No data available
CAS Number: 141-82-2
InChI: InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) check
Key: OFOBLEOULBTSOW-UHFFFAOYSA-N
InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
Key: OFOBLEOULBTSOW-UHFFFAOYAJ

SMILES: O=C(O)CC(O)=O
C(C(=O)O)C(=O)O
Chemical formula: C3H4O4
Molar mass: 104.061 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: 763 g/L
Acidity (pKa): pKa1 = 2.83
pKa2 = 5.69
Magnetic susceptibility (χ): -46.3·10−6 cm3/mol
Chemical Formula: C3H4O4
Average Molecular Weight: 104.0615

Monoisotopic Molecular Weight: 104.010958616
IUPAC Name: propanedioic acid
Traditional Name: malonic acid
CAS Registry Number: 141-82-2
SMILES: OC(=O)CC(O)=O
InChI Identifier: InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
InChI Key: OFOBLEOULBTSOW-UHFFFAOYSA-N
Molecular Weight： 104.06100
Exact Mass： 104.06
EC Number： 205-503-0
UNII： 9KX7ZMG0MK
ICSC Number： 1085
NSC Number： 8124
DSSTox ID： DTXSID7021659

Color/Form： White crystals|Crystalline powder
Colorless hygroscopic solid which sublimes in vacuum
HScode： 2917190090
PSA： 74.60000
XLogP3： -0.8
Appearance： Malonic acid appears as white crystals or crystalline powder.
Sublimes in vacuum.
Density： 1.6 g/cm3
Melting Point： 135 °C (decomp)
Boiling Point: 215 °C @ Press: 14 Torr
Flash Point： 201.9ºC
Refractive Index： 1.479
Water Solubility： H2O: 1400 g/L (20 ºC)
Storage Conditions： Store at RT.

Vapor Pressure： 4.66E-07mmHg at 25°C
PKA： 2.85(at 25 °C)
Dissociation Constants： 2.85 (at 25 °C)|pKa1 = 2.8, pKa2 = 5.7 at 25 °C
Experimental Properties：
Enthalpy of Sublimation: 72.7 kJ/mol at 306 deg K, 108.0 kJ/mol at 348 deg K
Henry's Law constant = 4.8X10-13 atm-cu m/mole at 23 °C
(estimated from vapor pressure and water solubility)
Hydroxyl radical reaction rate constant = 1.6X10-12 cu-cm/molc sec at 25 °C (est)
Air and Water Reactions： Water soluble.
Reactive Group： Acids, Carboxylic
Heat of Combustion： Molar heat of combustion: 864 kJ/mol
Heat of Vaporization： 92 kJ/mol

Critical Temperature & Pressure：
Critical temperature: 805 K (estimated);
critical pressure: 5640 kPa (estimated)
CAS: 141-82-2
Molecular Formula: C3H4O4
Molecular weight: 104.06
EINECS: 205-503-0
Purity: ≥99%
Appearance: White crystal powder
Melting point: 132-135 °C (dec.) (lit.)
Boiling point: 140ºC(decomposition)
Density: 1.619 g/cm3 at 25 °C

Refractive index: 1.478
Flash Point: 157°C
Storage condition: Sealed in dry,Room Temperature
Solubility : 1 M NaOH: soluble100mg/mL, clear to slightly hazy,
colorless to faintly yellow
Pka: 2.83(at 25ºC)
Stability: Stable.
Incompatible with oxidizing agents, reducing agents, bases.
HS Code: 29171910
PH: 3.17(1 mM solution);2.5(10 mM solution);
1.94(100 mM solution)
MDL: MFCD00002707

Water Solubility: 1400 g/L (20 ºC)
Vapor Presure: 0-0.2Pa at 25ºC
Physical and Chemical Properties:
Character: white crystal.
soluble in water, soluble in ethanol and ether, pyridine.
Color: White
Formula Weight: 104.1
Percent Purity: 0.99
Physical Form: Powder
Chemical Name or Material: Malonic acid
Melting point: 132-135 °C (dec.) (lit.)
Boiling point: 140℃（decomposition）

Density: 1.619 g/cm3 at 25 °C
vapor pressure: 0-0.2Pa at 25℃
refractive index: 1.4780
Flash point: 157°C
storage temp.: Sealed in dry,Room Temperature
solubility: 1 M NaOH: soluble100mg/mL, clear to slightly hazy,
colorless to faintly yellow
form: Liquid
pka: 2.83(at 25℃)
color: White
PH: 3.17(1 mM solution);2.5(10 mM solution);1.94(100 mM solution)

Water Solubility: 1400 g/L (20 ºC)
Merck: 14,5710
BRN: 1751370
Stability: Stable.
Incompatible with oxidizing agents, reducing agents, bases.
InChIKey: OFOBLEOULBTSOW-UHFFFAOYSA-N
LogP: -0.81
CAS DataBase Reference: 141-82-2(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: 9KX7ZMG0MK
NIST Chemistry Reference: Malonic acid(141-82-2)
EPA Substance Registry System: Propanedioic acid (141-82-2)
Molecular Weight: 104.06 g/mol

XLogP3: -0.8
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 2
Exact Mass: 104.01095860 g/mol
Monoisotopic Mass: 104.01095860 g/mol
Topological Polar Surface Area: 74.6Å²
Heavy Atom Count: 7
Formal Charge: 0
Complexity: 83.1
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0

Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Chemical formula: C3H4O4
Molar mass: 104.061 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: 763 g/L
Acidity (pKa): pKa1 = 2.83

pKa2 = 5.69
Magnetic susceptibility (χ): -46.3·10−6 cm3/mol
Chemical formula: C3H4O4
Molar mass: 104.061 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: 763 g/L
Acidity (pKa): pKa1 = 2.83
pKa2 = 5.69
Magnetic susceptibility (χ): -46.3·10−6 cm3/mol
Molecular Weight: 104.06 g/mol
XLogP3: -0.8
Hydrogen Bond Donor Count: 2

Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 2
Exact Mass: 104.01095860 Da
Monoisotopic Mass: 104.01095860 Da
Topological Polar Surface Area: 74.6 Å²
Heavy Atom Count: 7
Formal Charge: 0
Complexity: 83.1
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0

Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
CAS number: 141-82-2
EC number: 205-503-0
Hill Formula: C₃H₄O₄
Chemical formula: CH₂(COOH)₂
Molar Mass: 104.06 g/mol
HS Code: 2917 19 10
Density: 1.6 g/cm3
Flash point: 157 °C
Melting Point: >=135 °C

Vapor pressure: 0.002 hPa (25 °C)
Bulk density: 950 kg/m3
Solubility: 1390 g/l
Linear Formula: CH2(COOH)2
CAS Number: 141-82-2
Molecular Weight: 104.06
Beilstein: 1751370
EC Number: 205-503-0
MDL number: MFCD00002707
UNSPSC Code: 12352100
PubChem Substance ID: 24896631
NACRES: NA.21

Physical state: powder
Color: white
Odor: odorless
Melting point/range: 132 - 135 °C - dec.
Initial boiling point and boiling range: 215 °C at 18.66 hPa (decomposition)
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits: No data available
Flash point: 157 °C - c.c.
Autoignition temperature: No data available
Decomposition temperature: > 140 °C
pH: No data available
Viscosity, kinematic: No data available

Viscosity, dynamic: No data available
Water solubility: 766 g/l at 20 °C
Partition coefficient: n-octanol/water
log Pow: -0.81 -
Bioaccumulation is not expected. (Lit.)
Vapor pressure: 0.002 hPa at 25 °C
Density: 1.6 g/cm3
Relative density: 1.03 at 20 °C
Relative vapor density: No data available
Particle characteristics: No data available
Explosive properties: No data available
Oxidizing properties: none
Other safety information: No data available

Form: Crystals or powder or crystalline powder or granules
Assay (Aqueous acid-base Titration): ≥98.5 to ≤101.5%
Assay from Supplier's CofA: ≥98.5% (U.S. sourced material)
Comment: Material Sourced in the U.S. and in other countries
Identification (FTIR): Conforms (non-U.S. sourced material)
Appearance (Color): White
IUPAC Name: propanedioic acid
Molecular Formula: C3H4O4
InChI Key: OFOBLEOULBTSOW-UHFFFAOYSA-N
SMILES: OC(=O)CC(O)=O
Molecular Weight (g/mol): 104.06
CAS: 141-82-2

FIRST AID MEASURES of MALONIC ACID:
-Description of first-aid measures
*General advice
Show this material safety data sheet to the doctor in attendance.
*If inhaled
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
*In case of eye contact
After eye contact:
Rinse out with plenty of water.
Immediately call in ophthalmologist.
Remove contact lenses.
*If swallowed
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed
No data available

ACCIDENTAL RELEASE MEASURES of MALONIC ACID:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of MALONIC ACID:
-Extinguishing media:
*Suitable extinguishing media:
Water
Foam
Carbon dioxide (CO2)
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of MALONIC ACID:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Tightly fitting safety goggles
*Skin protection:
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Splash contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter type P2
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of MALONIC ACID:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
*Storage class:
Storage class (TRGS 510): 13:
Non Combustible Solids

STABILITY and REACTIVITY of MALONIC ACID:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature) .