PROPANEDIOIC ACID
PROPANEDIOIC ACID
Propanedioic acid, a dicarboxylic acid with the structure CH₂(COOH)₂, is used in the manufacture of barbiturates, coatings, biodegradable containers, and even surgical adhesives.
The ionized form of Propanedioic acid, along with its esters and salts, are known as malonates, and are important precursors in the biosynthesis of fatty acids and various biochemical processes.
Propanedioic acid is a white crystalline solid with numerous commercial uses, including as a precursor to specialty polyesters and a component in organic synthesis, such as in the production of vitamins B1 and B6.
CAS Number: 141-82-2
EC Number: 205-503-0
Chemical Formula: C3H4O4
Molecular Weight: 104.06100
Synonyms: 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 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.
Propanedioic acid is a conjugate acid of a malonate(1-).
Propanedioic acid appears as white crystals or crystalline powder.
Propanedioic acid sublimes in vacuum.
Propanedioic acid, is a dicarboxylic acid.
Propanedioic acid is a dicarboxylic acid with the CH2(COOH)2 structure.
The ionized forms of Propanedioic acid and its esters and salts are known as malonates.
For example, diethyl malonate is the diethyl ester of Propanedioic acid.
The name of Propanedioic acid comes from the Greek μλον (maron), which means “apple”.
The crystals of Propanedioic acids 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 Propanedioic acid in aqueous suspensions of titanium dioxide (TiO2) have been described.
Propanedioic acid is an alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.
Propanedioic acid has a role as a human metabolite.
Propanedioic acid is a conjugate acid of a malonate(1-).
The calcium salt of Propanedioic acid occurs in high concentrations in beetroot.
Propanedioic acid exists in its normal state as white crystals.
Propanedioic acid is the classic example of a competitive inhibitor:
Propanedioic acid acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.
In a well-known reaction, Propanedioic acid condenses with urea to form barbituric acid.
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 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 μλον (malon) meaning ‘apple’.
Propanedioic acid is also known as Dicarboxymethane.
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.
In addition, Propanedioic acid and coenzyme A can be biosynthesized from malonyl-CoA through Propanedioic acids interaction with the enzyme fatty acid synthase.
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.
Propanedioic acid is a dicarboxylic acid.
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.
Propanedioic acid is a white crystalline acid derived from malic acid and used in making barbiturates.
Propanedioic acid is 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 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.
Uses of Propanedioic acid:
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.
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 is a precursor to specialty polyesters.
Propanedioic acid can be converted into 1,3-propanediol for use in polyesters and polymers (whose usefulness is unclear though).
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.
In 2004, Propanedioic acid was listed by the US Department of Energy as one of the top 30 chemicals to be produced from biomass.
Propanedioic acid may be used as a cross-linking agent between corn starch and potato starch to improve Propanedioic acid mechanical properties.
Propanedioic acid is used in organic intermediates of vitamin B1, B2, B6 and spices, adhesives, resin additives, Propanedioic acid can be used for electroplating polishing compound and welding fluxing additive, etc.
Propanedioic acid may be used as a cross-linking agent between corn starch and potato starch to improve Propanedioic acid mechanical properties.
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 may be used as a cross-linking agent between corn starch and potato starch to improve Propanedioic acid mechanical properties.
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 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.
Applications of Propanedioic acid:
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.
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.
Propanedioic acid may be used as a cross-linking agent between corn starch and potato starch to improve Propanedioic acids mechanical properties.
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.
Propanedioic acid is a normal component of human urine, in small quantities, but a genetic disorder called methyl Propanedioic aciduria (also known as Propanedioic aciduria) causes high levels of methyl Propanedioic 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 Propanedioic acid’s more severe forms, neonatal death.
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 is 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.
Related Chemicals of Propanedioic acid:
The fluorinated version of Propanedioic acid is difluoromalonic acid.
Propanedioic acid is diprotic.
That is, Propanedioic acid can donate two protons per molecule.
Propanedioic acid’s first 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 Propanedioic acid, such as Diethyl malonate, Dimethyl malonate, Disodium malonate, Malonyl-CoA.
Structure and Preparation of Propanedioic 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.
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.
Preparation:
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.
Reactions of Propanedioic acid:
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.
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.
Briggs–Rauscher reaction:
Propanedioic acid is a key component in the Briggs–Rauscher reaction, the classic example of an oscillating chemical reaction.
Knoevenagel condensation:
In Knoevenagel condensation, Propanedioic acid or its diesters are reacted with the carbonyl group of an aldehyde or ketone, followed by a dehydration reaction.
Z=COOH (Propanedioic acid) or Z=COOR’ (malonate ester)
When Propanedioic acid itself is used normally because the desired product is one in which a second step has occurred, with loss of carbon dioxide, in the so-called Doebner modification.
The Doebner modification of the Knoevenagel condensation.
Thus, for example, the reaction product of acrolein and Propanedioic acid in pyridine is trans-2,4-Pentadienoic acid with one carboxylic acid group and not two.
Preparation of carbon suboxide:
Carbon suboxide is prepared by warming a dry mixture of phosphorus pentoxide (P4O10) and Propanedioic acid.
Propanedioic acid reacts in a similar way to malonic anhydride, forming malonates.
Biochemistry of Propanedioic acid:
Propanedioic acid is the classic example of a competitive inhibitor of the enzyme succinate dehydrogenase (complex II), in the respiratory electron transport chain.
Propanedioic 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 Propanedioic acid is a natural component of many foods, its is present in mammals including humans.
Pathology of Propanedioic acid:
If elevated Propanedioic acid levels are accompanied by elevated methylmalonic acid levels, this may indicate the metabolic disease combined malonic and methylmalonic aciduria (CMAMMA).
By calculating the Propanedioic acid to methylmalonic acid ratio in blood plasma, CMAMMA can be distinguished from classic methylmalonic academia.
History of Propanedioic acid:
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.
Handling and Storage of Propanedioic acid:
Handling:
Wear appropriate personal protective equipment (PPE) such as gloves, goggles, and lab coats.
Avoid inhalation, ingestion, and direct contact with skin and eyes.
Use in well-ventilated areas to minimize inhalation risks.
Avoid creating dust and keep containers tightly closed when not in use.
Storage:
Store in a cool, dry place away from incompatible substances.
Keep away from strong oxidizing agents and bases.
Store in a sealed container to prevent contamination and degradation.
Stability and Reactivity of Propanedioic acid:
Stability:
Propanedioic acid is stable under normal conditions of use and storage.
Avoid exposure to moisture and high temperatures, which can cause decomposition.
Reactivity:
Reacts with strong oxidizers, strong bases, and certain metals.
Can undergo reactions with alkalis and other bases, leading to formation of salts and release of heat.
First Aid Measures of Propanedioic acid:
Inhalation:
Move the affected person to fresh air immediately.
Seek medical attention if respiratory symptoms develop or persist.
Skin Contact:
Remove contaminated clothing.
Rinse the affected skin with plenty of water for at least 15 minutes.
Seek medical advice if irritation or symptoms persist.
Eye Contact:
Rinse immediately with plenty of water for at least 15 minutes.
Remove contact lenses if present and easy to do.
Seek medical attention promptly.
Ingestion:
Do not induce vomiting.
Rinse mouth thoroughly with water.
Seek medical attention immediately.
Firefighting Measures of Propanedioic acid:
Suitable Extinguishing Media:
Use water spray, dry chemical, or foam to extinguish fires.
Avoid using water jets as they may spread the fire.
Specific Hazards:
Decomposes on heating, emitting toxic fumes including carbon monoxide and carbon dioxide.
Protective Equipment:
Firefighters should wear self-contained breathing apparatus and protective clothing to prevent exposure to smoke and fumes.
Accidental Release Measures of Propanedioic acid:
Personal Precautions:
Evacuate the area if necessary and ensure adequate ventilation.
Wear appropriate PPE to avoid direct contact.
Containment:
Contain spills with inert materials such as sand or earth.
Prevent the release of the substance into drains or watercourses.
Cleanup:
Collect the spilled material using suitable methods and dispose of Propanedioic acid in accordance with local regulations.
Clean the affected area with water and detergent.
Exposure Controls/Personal Protective Equipment of Propanedioic acid:
Exposure Limits:
No specific exposure limits are established; however, avoid inhalation and prolonged skin contact.
Engineering Controls:
Use in well-ventilated areas or under a fume hood to reduce airborne dust and vapors.
Personal Protective Equipment (PPE):
Respiratory Protection:
Use a dust mask or respirator if dust is generated or if ventilation is insufficient.
Hand Protection:
Wear protective gloves, such as nitrile or neoprene gloves.
Eye Protection:
Wear safety goggles or glasses with side shields.
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Identifiers of Propanedioic acid:
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: Propanedioic acid appears as white crystals or crystalline powder. Sublimes in vacuum.
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: Propanedioic 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
Properties of Propanedioic acid:
Exact Mass: 104.01095860 g/mol
Monoisotopic Mass: 104.01095860 g/mol
Topological Polar Surface Area: 74.6Ų
Heavy Atom Count: 7
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
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: Propanedioic 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: 74.6Ų
Heavy Atom Count: 7
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
Related compounds of Propanedioic acid:
Malondialdehyde
Dimethyl malonate
Other anions:
Malonate
Related carboxylic acids:
Oxalic acid
Propionic acid
Succinic acid
Fumaric acid
Names of Propanedioic acid:
Preferred IUPAC name:
Propanedioic acid
Other names:
Methanedicarboxylic acid