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Propanedioic acid is a dicarboxylic acid with structure CH2(COOH)2.
The ionized form of Propanedioic acid, as well as its esters and salts, are known as malonates.
For example, diethyl malonate is Propanedioic acid's diethyl ester.
The name originates from the Greek word μᾶλον (malon) meaning 'apple'.
CAS Number: 141-82-2
EC Number: 205-503-0
IUPAC Name: propanedioic acid
Chemical Formula: CH2COOH2
Other names: 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
Propanedioic acid is the second-smallest aliphatic dicarboxylic acid. (Oxalic acid is the smallest.)
Propanedioic acid should not be confused with malic or maleic acid, both of which also contain two carboxyls.
Propanedioic acid is a white crystalline solid with a decomposition point of ≈135 °C.
Propanedioic acid is highly soluble in water and oxygenated solvents.
Propanedioic acid has numerous commercial uses:
Propanedioic acid is a precursor to specialty polyesters; Propanedioic acid is used in the manufacture of barbiturates, coatings, and biodegradable containers; and Propanedioic acid is even a component of surgical adhesives.
Propanedioic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH₂(COOH)₂.
The ionized form of Propanedioic acid, as well as its esters and salts, are known as malonates.
For example, diethyl malonate is Propanedioic acid's diethyl ester.
The name originates from the Greek word μᾶλον (malon) meaning 'apple'.
Uses
Propanedioic acid is used as a precursor in polymers and polyester.
Propanedioic acid is used in flavours as well as the fragrance industry.
Propanedioic acid is used to control the acidity.
Propanedioic acid is used in pharmaceutical products.
Propanedioic acid is used as a cross-linking agent between potato starch and cornstarch to enhance its mechanical properties.
Propanedioic acid is used in the preparation of barbituric salt.
Propanedioic acid is used in electroplating.
Propanedioic acid is used to produce vitamin B1, vitamin B6, vitamin B2, and amino acids.
Propanedioic acid is used in chemical synthesis as a building block.
Propanedioic 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.
Propanedioic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Propanedioic acid exists in all living species, ranging from bacteria to humans.
Within humans, Propanedioic acid participates in a number of enzymatic reactions.
In particular, Propanedioic acid and acetic acid can be converted into acetoacetic acid; which is mediated by the enzyme fatty acid synthase.
What is Propanedioic acid?
The name is derived from a Greek word Malon which means apple.
Malonates are the ionized form of Propanedioic acid, along with its esters and salts.
Propanedioic acid appears as a white crystal or crystalline powder.
Propanedioic acid dissolves in alcohol, pyridine, and ether.
Propanedioic acid was first prepared in the year, 1858 by the French chemist Victor Dessaignes by the oxidation of malic acid.
Propanedioic acid is found in some fruit’s viz citrus fruits.
The amount of Propanedioic acid produced from fruits through organic farming is greater than the fruits grown through conventional agriculture.
Propanedioic acid can be produced through the fermentation of glucose.
Beta ketoacyl synthase domain.
In addition, Propanedioic acid and coenzyme A can be biosynthesized from malonyl-CoA through Propanedioic acids interaction with the enzyme fatty acid synthase.
malonyl/acetyl transferase domain.
An Propanedioic acid in which the two carboxy groups are separated by a single methylene group.
In humans, Propanedioic acid is involved in fatty acid biosynthesis. Outside of the human body, Propanedioic 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 Propanedioic acid a potential biomarker for the consumption of these foods.
Propanedioic acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, combined malonic and methylPropanedioic aciduria, and early preeclampsia; Propanedioic acid has also been linked to the inborn metabolic disorder malonyl-coa decarboxylase deficiency.
Propanedioic acid is a dicarboxylic acid with structural formula CH2(COOH)2 and chemical formula C3H4O4.
The name Propanedioic acid originated from the word ‘Malon’ which is Greek for ‘apple’.
Methane Dicarboxylic acid is another name for Propanedioic acid.
The ester and salts of Propanedioic 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 Propanedioic acid
The synthesis of Propanedioic acid usually begins with chloroacetic acid.
Propanedioic acid is also synthesized by cyanoacetic acid or by acid saponification reaction of malonates.
From monochloroacetic acid, Propanedioic 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 Propanedioic acid.
Propanedioic 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.
Propanedioic acid itself is rather unstable and has few applications.
Propanedioic acids calcium salt occurs in beetroot, but the acid Propanedioic acidself is usually prepared by hydrolyzing diethyl malonate.
Propanedioic 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.
Propanedioic acids utility in synthesis arises from the reactivity of Propanedioic 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
Propanedioic acid is a precursor to specialty polyesters.
Propanedioic 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.
Propanedioic 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 Propanedioic 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.
Propanedioic 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 Propanedioic 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.
Propanedioic 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, Propanedioic acid can be used to control acidity, either as an excipient in pharmaceutical formulation or natural preservative additive for foods.
Propanedioic 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.
Propanedioic 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 Propanedioic acid and derivatives as a surgical adhesive.
General description
The crystals of MA are triclinic at room temperature.
The oxidation of Propanedioic 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 Propanedioic acid Lewis structure has been found by the X-ray crystallography method.
The Propanedioic acid structure CH2(COOH)2 has two carboxylic acids.
The salts and esters of Propanedioic acid (malonates) have structures similar to Propanedioic acid.
Applications of Propanedioic acid
Propanedioic acids utility in synthesis arises from the reactivity of Propanedioic 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.
Propanedioic acid Uses
Propanedioic 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.
Propanedioic 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.
Propanedioic acid is used in cosmetics as a buffering and as a flavouring agent in food.
Propanedioic acid is used as a component of alkyd resins, used in coating applications to protect from UV rays, oxidation, and corrosion.
Propanedioic 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.
Propanedioic acid Application
Propanedioic acid may be used as a cross-linking agent between corn starch and potato starch to improve Propanedioic acids mechanical properties.
Sometimes alternatively referred to as propanedioic acid, Propanedioic acid is a dicarboxylic acid of ethane with a methylene group separating the two carbonyl moieties.
Propanedioic acid occurs in small quantities naturally in urine and beetroot, but is typically prepared by hydrolyzing diethyl malonate.
Molecular Weight：104.06146
Introduction: Propanedioic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2.
The ionized form of Propanedioic acid, as well as Propanedioic acids esters and salts, are known as malonates. For example, diethyl malonate is Propanedioic acid's diethyl ester.
The name originates from the Greek word (malon) meaning 'apple'.
Propanedioic acid half-oxyesters (MAHOs) and Propanedioic 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 Propanedioic 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
Propanedioic acid is a white crystalline acid derived from malic acid and used in making barbiturates.
The ionized form of Propanedioic acid, as well as Propanedioic acids esters and salts, are known as malonates.
For example, diethyl malonate is Propanedioic acid’s diethyl ester.
The name originates from the Greek word μᾶλον (malon) meaning ‘apple’.
Propanedioic acid itself is rather unstable and has few applications.
Propanedioic acids calcium salt occurs in beetroot, but the acid itself is usually prepared by hydrolyzing diethyl malonate.
Propanedioic acid undergoes the usual reactions of carboxylic acids as well as facile cleavage into acetic acid and carbon dioxide.
Propanedioic acid is often mistakenly believed to occur in beetroot at high concentration, and a study on the composition of sugar beet liquors revealed no Propanedioic acid.
Propanedioic acid exists in its normal state as white crystals.
Application Notes
Propanedioic acid is used to prepare barbiturates.
Propanedioic acids derivative diethylmalonate is used in Knoevenagel condensation reactions as well as reacts with acetone to form Meldrum's acid.
Propanedioic acid is used to control acidity, preservative additive for foods and as an excipient in pharmaceutical formulation.
Propanedioic acid acts as a precursor to polyesters and as an active component in alkyd resins.
Further, Propanedioic acid is used as a building block in chemical synthesis.
In addition to this, Propanedioic acid is used to prepare starch-based resin.
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
Propanedioic 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 Propanedioic acid than fruits produced in conventional agriculture.
Propanedioic 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 Propanedioic acid.
Industrially, however, Propanedioic acid is produced by hydrolysis of dimethyl malonate or diethyl malonate.
Propanedioic acid has also been produced through fermentation of glucose.
Organic reactions
Propanedioic 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, Propanedioic acid condenses with urea to form barbituric acid.
Propanedioic acid may also condensed be with acetone to form Meldrum's acid, a versatile intermediate in further transformations.
The esters of Propanedioic 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.
Propanedioic 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.
Propanedioic acid is a substance found in some fruits that occurs naturally.
Fruits generated in organic farming contain greater concentrations of Propanedioic acid in citrus compared to fruits generated in conventional farming.
The systematic name for Propanedioic acid IUPAC is propanedioic acid.
Propanedioic acid is the archetypal instance of a competitive inhibitor: Propanedioic acid functions in the respiratory electron transport chain against succinate dehydrogenase.
Propanedioic acid is correlated with deficiency of malonyl-CoA decarboxylase, an inborn metabolism mistake.
Propanedioic 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 Propanedioic acid than fruits produced in conventional agriculture.
Propanedioic acid was first prepared in 1858 by the French chemist Victor Dessaignes via the oxidation of malic acid.
Propanedioic acid is the archetypal example of a competitive inhibitor: Propanedioic acid acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.
Propanedioic acid is also frequently used as an enolate in Knoevenagel condensations or condensed with acetone to form Meldrum’s acid.
The esters of Propanedioic acid are also used as a −CH2COOH synthon in the malonic ester synthesis.
Propanedioic acid is also known to be a competitive inhibitor of succinic dehydrogenase, the enzyme responsible for the dehydrogenation of succinate within Krebs cycle.
Propanedioic 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.
