Carboxyacetic acid (Malonic acid) (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2.
The ionized form of Carboxyacetic acid (Malonic acid), as well as its esters and salts, are known as malonates. For example, diethyl malonate is Carboxyacetic acid (Malonic 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
Molecular Formula: C3H4O4
Other names: Malonic Acid, propanedioic acid, 141-82-2, Dicarboxymethane, Carboxyacetic acid, Methanedicarboxylic acid, malonate, Kyselina malonova, 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, Carboxyacetic acid (Malonic Acid), 99%, Carboxyacetic acid (Malonic Acid) (8CI), 1o4m, MLI, Malonate dicarboxylic acid, Carboxyacetic acid (Malonic Acid), 99.5%, Propanedioic acid (9CI), SCHEMBL336, WLN: QV1VQ, Carboxyacetic acid (Malonic Acid) [MI], CH2(COOH)2, CHEMBL7942, Carboxyacetic acid (Malonic Acid) [INCI], DTXCID401659, SCHEMBL1471092, BDBM14673, Propanedioic acid dithallium salt, Carboxyacetic acid (Malonic Acid), analytical standard, AMY11201, BCP05571, STR00614, Tox21_200534, AC8295, LMFA01170041, s3029, Carboxyacetic acid (Malonic Acid), ReagentPlus(R), 99%, AKOS000119034, CS-W019962, DB02175, PROPANEDIOIC ACID Carboxyacetic acid (Malonic Acid), NCGC00248681-01, NCGC00258088-01, BP-11453, CAS-141-82-2, SY001875, Carboxyacetic acid (Malonic Acid), SAJ first grade, >=99.0%, FT-0628127, FT-0628128, FT-0690260, FT-0693474, M0028, NS00013842, EN300-18457, Carboxyacetic acid (Malonic Acid), Vetec(TM) reagent grade, 98%, C00383, C02028, C04025, Q421972, J-521669, Z57965450, F1908-0177, Carboxyacetic acid (Malonic Acid), certified reference material, TraceCERT(R), 592A9849-68C3-4635-AA3D-CBC44965EA3A, Carboxyacetic acid (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, Carboxyacetic acid (Malonic Acid), anhydrous, free-flowing, Redi-Dri(TM), ReagentPlus(R), 99%, LML.
History
Carboxyacetic 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 Carboxyacetic acid (Malonic acid) than fruits produced in conventional agriculture.
Carboxyacetic acid (Malonic acid) was first prepared in 1858 by the French chemist Victor Dessaignes via the oxidation of malic acid.
Structure and preparation
The structure has been determined by X-ray crystallography and extensive property data including for condensed phase thermochemistry are available from the National Institute of Standards and Technology.
A classical preparation of Carboxyacetic acid (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 Carboxyacetic acid (Malonic acid).
Industrially, however, Carboxyacetic acid (Malonic acid) is produced by hydrolysis of dimethyl malonate or diethyl malonate.
It has also been produced through fermentation of glucose.
Organic reactions
Carboxyacetic acid (Malonic acid) reacts as a typical carboxylic acid: forming amide, ester, anhydride, and chloride derivatives.
Malonic anhydride can be used as an intermediate to mono-ester or amide derivatives, while malonyl chloride is most useful to obtain diesters or diamides.
In a well-known reaction, Carboxyacetic acid (Malonic acid) condenses with urea to form barbituric acid.
Carboxyacetic acid (Malonic acid) may also be condensed with acetone to form Meldrum's acid, a versatile intermediate in further transformations.
The esters of Carboxyacetic acid (Malonic acid) are also used as a −CH2COOH synthon in the malonic ester synthesis.
Mitochondrial fatty acid synthesis
Carboxyacetic acid (Malonic acid) is the starting substrate of mitochondrial fatty acid synthesis (mtFASII), in which it is converted to malonyl-CoA by malonyl-CoA synthetase (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.
Briggs–Rauscher reaction
Carboxyacetic acid (Malonic acid) is a key component in the Briggs–Rauscher reaction, the classic example of an oscillating chemical reaction.
Knoevenagel condensation
In Knoevenagel condensation, Carboxyacetic acid (Malonic acid) or its diesters are reacted with the carbonyl group of an aldehyde or ketone, followed by a dehydration reaction.
When Carboxyacetic acid (Malonic acid) itself is used, it is 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.
Thus, for example, the reaction product of acrolein and Carboxyacetic acid (Malonic 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 Carboxyacetic acid (Malonic acid).
It reacts in a similar way to malonic anhydride, forming malonates.
Applications
Carboxyacetic acid (Malonic acid) is a precursor to specialty polyesters.
It can be converted into 1,3-propanediol for use in polyesters and polymers (whose usefulness is unclear though).
It 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 Carboxyacetic acid (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.
It 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 Carboxyacetic acid (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, Carboxyacetic acid (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, Carboxyacetic acid (Malonic acid) can be used to control acidity, either as an excipient in pharmaceutical formulation or natural preservative additive for foods.
Carboxyacetic acid (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.
Carboxyacetic acid (Malonic acid) (up to 37.5% w/w) has been used to cross-link corn and potato starches to produce a biodegradable thermoplastic; the process is performed in water using non-toxic catalysts.
Starch-based polymers comprised 38% of the global biodegradable polymers market in 2014 with food packaging, foam packaging, and compost bags as the largest end-use segments.
Eastman Kodak company and others use Carboxyacetic acid (Malonic acid) and derivatives as a surgical adhesive.
Pathology
If elevated Carboxyacetic acid (Malonic acid) levels are accompanied by elevated methylCarboxyacetic acid (Malonic acid) levels, this may indicate the metabolic disease combined malonic and methylCarboxyacetic acid (Malonic acid)uria (CMAMMA).
By calculating the Carboxyacetic acid (Malonic acid) to methylCarboxyacetic acid (Malonic acid) ratio in blood plasma, CMAMMA can be distinguished from classic methylCarboxyacetic acid (Malonic acid)emia.
Biochemistry
Carboxyacetic acid (Malonic acid) is the classic example of a competitive inhibitor of the enzyme succinate dehydrogenase (complex II), in the respiratory electron transport chain.
It 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 Carboxyacetic acid (Malonic acid) is a natural component of many foods, it is present in mammals including humans.
Consumer Uses
Carboxyacetic acid (Malonic acid) is used in the following products: adhesives and sealants, inks and toners, pH regulators and water treatment products, washing & cleaning products, coating products, fillers, putties, plasters, modelling clay, polishes and waxes and cosmetics and personal care products.
Other release to the environment of Carboxyacetic acid (Malonic acid) is likely to occur from: indoor use as reactive substance.
Other release to the environment of Carboxyacetic acid (Malonic acid) is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Widespread uses by professional workers
Carboxyacetic acid (Malonic acid) is used in the following products: coating products, metal surface treatment products, non-metal-surface treatment products, polymers and laboratory chemicals.
Carboxyacetic acid (Malonic acid) is used for the manufacture of: plastic products, fabricated metal products, electrical, electronic and optical equipment and machinery and vehicles.
Other release to the environment of Carboxyacetic acid (Malonic acid) is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).
Formulation
Carboxyacetic acid (Malonic acid) is used in the following products: laboratory chemicals, coating products, metal surface treatment products, non-metal-surface treatment products, pharmaceuticals and polymers.
Release to the environment of Carboxyacetic acid (Malonic acid) can occur from industrial use: formulation of mixtures.
Uses at industrial sites
Carboxyacetic acid (Malonic acid) is used in the following products: pH regulators and water treatment products, pharmaceuticals, laboratory chemicals, polymers, non-metal-surface treatment products, coating products and metal surface treatment products.
Carboxyacetic acid (Malonic acid) is used for the manufacture of: chemicals, plastic products, fabricated metal products, electrical, electronic and optical equipment and machinery and vehicles.
Release to the environment of Carboxyacetic acid (Malonic acid) can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid, in the production of articles and as processing aid.
Molar mass: 104.061 g·mol−1
Density: 1.619 g/cm3
Melting point: 135 to 137 °C
Solubility in water: 763 g/L
Acidity (pKa): pKa1 = 2.83
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
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Carboxyacetic acid (Malonic Acid) is a useful organic compound with various benefits.
Carboxyacetic acid (Malonic Acid) is IUPAC name is propanedioic acid.
Carboxyacetic acid (Malonic Acid) should not be confused with malic or maleic acid.
Carboxyacetic acid (Malonic Acid), also known as propanedioic acid, is a dicarboxylic acid with structure CH2(COOH)2.
Carboxyacetic acid (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.
Carboxyacetic acid (Malonic Acid) decomposes to acetic acid and carbon dioxide at 140℃.
Carboxyacetic acid (Malonic Acid) does not decompose at 1.067×103~1.333×103Pa vacuum, but directly sublimates.
The ionised form of Carboxyacetic acid (Malonic Acid), as well as its esters and salts, are known as malonates.
For example, diethyl malonate is Carboxyacetic acid (Malonic Acid)'s ethyl ester.
The name originates from Latin malum, meaning apple.
Carboxyacetic acid (Malonic Acid) is a white crystalline solid that decomposes at approximately 135°C.
Carboxyacetic acid (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.
Carboxyacetic acid (Malonic Acid) is slightly soluble in pyridine.
Carboxyacetic acid (Malonic Acid) can decompose to formic acid and carbon dioxide in case of potassium permanganate.
Since that Carboxyacetic acid (Malonic Acid) generates carbon dioxide and water after heated without pollution problems, it can be directly used as aluminum surface treatment agent.
Carboxyacetic acid (Malonic Acid) is a dicarboxylic acid belonging to the family of carboxylic acids.
A Carboxyacetic acid (Malonic Acid) contains two carboxylic acid functional groups.
Usually, a Carboxyacetic acid (Malonic Acid) exhibits the same chemical behavior as monocarboxylic acids.
This naturally occurs in certain fruits.
Carboxyacetic acid (Malonic Acid), is a dicarboxylic acid with the chemical formula CH₂(COOH)₂.
Carboxyacetic acid (Malonic Acid) is a compound containing two carboxylic acid functional groups (-COOH) attached to a central carbon atom.
Carboxyacetic acid (Malonic Acid) is notable for its use in organic chemistry, particularly in the preparation of certain chemicals through a series of reactions known as the malonic ester synthesis.
In this synthesis, the diester of Carboxyacetic acid (Malonic Acid) is often used as a starting material to introduce a two-carbon unit into a molecule.
Carboxyacetic acid (Malonic Acid) is an alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.
Carboxyacetic acid (Malonic Acid) has a role as a human metabolite.
Carboxyacetic acid (Malonic Acid) is a conjugate acid of a malonate(1-).
Carboxyacetic acid (Malonic Acid) is an organic compound naturally found in some fruits.
Fruits produced in organic farming have greater concentrations of Carboxyacetic acid (Malonic Acid) than those generated from conventional farming practices.
Carboxyacetic acid (Malonic Acid) is often found in some citrus fruits and vegetables.
Carboxyacetic acid (Malonic Acid) is a component of food items, it is present in animals, including humans.
Carboxyacetic acid (Malonic Acid) is a dicarboxylic acid with structure CH2(COOH)2.
The ionized form of Carboxyacetic acid (Malonic Acid), as well as its esters and salts, are known as malonates.
For example, diethyl malonate is Carboxyacetic acid (Malonic Acid)'s diethyl ester.
The name originates from the Greek word μᾶλον (malon) meaning 'apple'.
Carboxyacetic 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 Carboxyacetic acid (Malonic Acid) than fruits produced in conventional agriculture.
Carboxyacetic acid (Malonic Acid), also known as malonate or H2MALO, belongs to the class of organic compounds known as dicarboxylic acids and derivatives.
These are organic compounds containing exactly two carboxylic acid groups.
Carboxyacetic acid (Malonic Acid) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Carboxyacetic acid (Malonic Acid) exists in all living species, ranging from bacteria to humans.
Within humans, Carboxyacetic acid (Malonic Acid) participates in a number of enzymatic reactions.
In particular, Carboxyacetic acid (Malonic Acid) and acetic acid can be converted into acetoacetic acid; which is mediated by the enzyme fatty acid synthase.
In addition, Carboxyacetic acid (Malonic Acid) and coenzyme A can be biosynthesized from malonyl-CoA through its interaction with the enzyme fatty acid synthase.
An Carboxyacetic acid (Malonic Acid) in which the two carboxy groups are separated by a single methylene group.
In humans, Carboxyacetic acid (Malonic Acid) is involved in fatty acid biosynthesis.
Outside of the human body, Carboxyacetic acid (Malonic Acid) has been detected, but not quantified in, several different foods, such as red beetroots, corns, scarlet beans, common beets, and cow milks.
This could make Carboxyacetic acid (Malonic Acid) a potential biomarker for the consumption of these foods.
Carboxyacetic acid (Malonic Acid), with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, combined malonic and methylCarboxyacetic acid (Malonic Acid)uria, and early preeclampsia; Carboxyacetic acid (Malonic Acid) has also been linked to the inborn metabolic disorder malonyl-coa decarboxylase deficiency.
Carboxyacetic acid (Malonic Acid) is a white crystalline solid at room temperature and is soluble in water.
Carboxyacetic acid (Malonic Acid) has been used in various chemical reactions and organic syntheses due to its ability to act as a versatile building block for the introduction of carboxylic acid groups into organic molecules.
Carboxyacetic acid (Malonic Acid) synthesis is used to synthesise carboxylic acid derivatives by creating a substituted acetic acid.
Carboxyacetic acid (Malonic Acid) synthesis is a method used in organic chemistry to synthesise carboxylic acid derivatives.
Carboxyacetic acid (Malonic Acid) involves the alkylation and subsequent acidic hydrolysis of a malonic ester to create a substituted acetic acid.
The process is named after the reagent Carboxyacetic acid (Malonic Acid), which is used as the starting material in the reaction.
The first step in the Carboxyacetic acid (Malonic Acid) synthesis is the deprotonation of the malonic ester.
This is achieved by treating the ester with a strong base, typically sodium ethoxide.
This results in the formation of an enolate ion, which is a highly reactive species.
The enolate ion then undergoes alkylation.
This involves the reaction of the enolate ion with an alkyl halide, resulting in the substitution of a hydrogen atom on the Carboxyacetic acid (Malonic Acid) with an alkyl group.
This step can be repeated to introduce two alkyl groups onto the malonic ester.
The final step in the Malonic ester synthesis is the acidic hydrolysis and decarboxylation of the alkylated malonic ester.
This involves treating the ester with an acid, typically hydrochloric acid, and heating.
This results in the loss of a molecule of carbon dioxide and the formation of a substituted acetic acid.
Carboxyacetic acid (Malonic Acid) synthesis is a versatile method for the synthesis of carboxylic acid derivatives.
Carboxyacetic acid (Malonic Acid) allows for the introduction of a wide range of alkyl groups onto the acetic acid molecule, providing a method for the synthesis of a wide range of carboxylic acid derivatives.
The reaction conditions are relatively mild, and the reagents and starting materials are readily available, making it a practical method for the synthesis of carboxylic acid derivatives.
Carboxyacetic acid (Malonic Acid)s 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 Carboxyacetic acid (Malonic Acid).
Industrially, however, Carboxyacetic acid (Malonic Acid) is produced by hydrolysis of dimethyl malonate or diethyl malonate.
Carboxyacetic acid (Malonic Acid) has also been produced through fermentation of glucose.
Carboxyacetic acid (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.
Carboxyacetic acid (Malonic Acid) is a substance found in some fruits that occurs naturally.
Fruits generated in organic farming contain greater concentrations of Carboxyacetic acid (Malonic Acid) in citrus compared to fruits generated in conventional farming.
Carboxyacetic acid (Malonic Acid) is a normal component of human urine, in small quantities, but a genetic disorder called methyl Carboxyacetic acid (Malonic Acid)uria (also known as Carboxyacetic acid (Malonic Acid)uria) causes high levels of methyl Carboxyacetic acid (Malonic Acid) in the blood serum and urine.
Patients with this disorder suffer from severe metabolic acidosis and a metabolic block in the vitamin B12 dependent conversion of propionyl CoA to succinyl CoA.
In infants, symptoms can include developmental delay, cardiomyopathy, mental retardation, and in its more severe forms, neonatal death.
The calcium salt of Carboxyacetic acid (Malonic Acid) occurs in high concentrations in beetroot.
Carboxyacetic acid (Malonic Acid) exists in its normal state as white crystals.
Carboxyacetic acid (Malonic Acid) is the classic example of a competitive inhibitor: It acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.
Carboxyacetic acid (Malonic Acid) reacts as a typical carboxylic acid: forming amide, ester, anhydride, and chloride derivatives.
Carboxyacetic acid (Malonic Acid) 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, Carboxyacetic acid (Malonic Acid) condenses with urea to form barbituric acid.
Carboxyacetic acid (Malonic Acid) may also be condensed with acetone to form Meldrum's acid, a versatile intermediate in further transformations.
The esters of Carboxyacetic acid (Malonic Acid) are also used as a −CH2COOH synthon in the malonic ester synthesis.
Carboxyacetic acid (Malonic Acid), also called Propanedioic Acid, (HO2CCH2CO2H), a dibasic organic acid whose diethyl ester is used in syntheses of vitamins B1 and B6, barbiturates, and numerous other valuable compounds.
Carboxyacetic acid (Malonic Acid) itself is rather unstable and has few applications.
Carboxyacetic acid (Malonic Acid)s calcium salt occurs in beetroot, but the acid Carboxyacetic acid (Malonic Acid)self is usually prepared by hydrolyzing diethyl malonate.
Carboxyacetic acid (Malonic Acid) undergoes the usual reactions of carboxylic acids as well as facile cleavage into acetic acid and carbon dioxide.
Carboxyacetic acid (Malonic Acid), also called malonic ester, is prepared by the reaction of ethyl alcohol with cyanoacetic acid.
Carboxyacetic acid (Malonic Acid)s utility in synthesis arises from the reactivity of Carboxyacetic acid (Malonic Acid)s 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.
Carboxyacetic acid (Malonic Acid) is a colourless, fragrant liquid boiling at 181.4° C.
Carboxyacetic acid (Malonic Acid) is the starting substrate of mitochondrial fatty acid synthesis (mtFASII), in which it is converted to malonyl-CoA by malonyl-CoA synthetase (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.
The carboxyl functional group that characterizes the carboxylic acids is unusual in that it is composed of two functional groups described earlier in this text.
As may be seen in the formula on the right, the carboxyl group is made up of a hydroxyl group bonded to a carbonyl group.
Carboxyacetic acid (Malonic Acid) is often written in condensed form as –CO2H or –COOH.
Other combinations of functional groups were described previously, and significant changes in chemical behavior as a result of group interactions were described (e.g. phenol & aniline).
In this case, the change in chemical and physical properties resulting from the interaction of the hydroxyl and carbonyl group are so profound that the combination is customarily treated as a distinct and different functional group.
Carboxyacetic acid (Malonic Acid), formally propanedioic acid, is the second-smallest aliphatic dicarboxylic acid. (Oxalic acid is the smallest.)
Carboxyacetic acid (Malonic Acid) should not be confused with malic or maleic acid, both of which also contain two carboxyls.
Carboxyacetic acid (Malonic Acid) is a white crystalline solid with a decomposition point of ≈135 °C.
Carboxyacetic acid (Malonic Acid) is highly soluble in water and oxygenated solvents.
Carboxyacetic acid (Malonic Acid) is a precursor to specialty polyesters; Carboxyacetic acid (Malonic Acid) is used in the manufacture of barbiturates, coatings, and biodegradable containers; and Carboxyacetic acid (Malonic Acid) is even a component of surgical adhesives.
Carboxyacetic acid (Malonic Acid) (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH₂(COOH)₂.
The ionized form of Carboxyacetic acid (Malonic Acid), as well as its esters and salts, are known as malonates.
For example, diethyl malonate is Carboxyacetic acid (Malonic Acid)'s diethyl ester.
Carboxyacetic acid (Malonic Acid) is a dicarboxylic acid with a chemical formula C3H4O4.
Carboxyacetic acid (Malonic Acid)s are organic compounds containing two carboxylic acid functional groups.
Carboxyacetic acid (Malonic Acid)s generally show the same chemical behaviour and reactivity as monocarboxylic acids.
Carboxyacetic acid (Malonic Acid) is a substance found in some fruits that occurs naturally.
Fruits generated in organic farming contain greater concentrations of Carboxyacetic acid (Malonic Acid) in citrus compared to fruits generated in conventional farming
Carboxyacetic acid (Malonic Acid) condenses with urea to form barbituric acid.
Carboxyacetic 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 Carboxyacetic acid (Malonic Acid) are also used as a - CH2COOH synthon in the malonic ester synthesis.
Carboxyacetic acid (Malonic Acid) is the classic example of a competitive inhibitor of the enzyme succinate dehydrogenase (complex II), in the respiratory electron transport chain.
Carboxyacetic acid (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.
Carboxyacetic acid (Malonic Acid)s 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.
Carboxyacetic acid (Malonic Acid)s 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 Carboxyacetic acid (Malonic Acid) dissociate to an extent in water to yield hydrogen ions.
The pH of solutions of Carboxyacetic acid (Malonic Acid)s 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.
Carboxyacetic acid (Malonic Acid)s 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 Carboxyacetic acid (Malonic Acid)s 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 Carboxyacetic acid (Malonic Acid) to corrode or dissolve iron, steel, and aluminum parts and containers.
Carboxyacetic acid (Malonic Acid)s, 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 Carboxyacetic acid (Malonic Acid)s with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides.
Carboxyacetic acid (Malonic Acid)s, 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 Carboxyacetic acid (Malonic Acid) is incompatible with strong oxidizers.
Carboxyacetic acid (Malonic Acid) is also incompatible with bases and reducing agents.
Carboxyacetic acid (Malonic Acid), (HO2CCH2CO2H), a dibasic organic acid whose diethyl ester is used in syntheses of vitamins B1 and B6, barbiturates, and numerous other valuable compounds.
Carboxyacetic acid (Malonic Acid) itself is rather unstable and has few applications.
Carboxyacetic acid (Malonic Acid) is calcium salt occurs in beetroot, but the acid itself is usually prepared by hydrolyzing diethyl malonate.
Carboxyacetic acid (Malonic Acid) undergoes the usual reactions of carboxylic acids as well as facile cleavage into acetic acid and carbon dioxide.
Carboxyacetic acid (Malonic Acid), also called malonic ester, is prepared by the reaction of ethyl alcohol with cyanoacetic acid.
Carboxyacetic acid (Malonic Acid) is utility in synthesis arises from the reactivity of its 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.
Carboxyacetic acid (Malonic Acid) is a colourless, fragrant liquid boiling at 181.4° C.
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 Carboxyacetic acid (Malonic Acid) starts from chloroacetic acid:[9]
Carboxyacetic acid (Malonic Acid) is the classic example of a competitive inhibitor of the enzyme succinate dehydrogenase (complex II), in the respiratory electron transport chain.
Carboxyacetic acid (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 Carboxyacetic acid (Malonic Acid) is a natural component of many foods, it is present in mammals including humans.
Carboxyacetic acid (Malonic Acid) is also known as Propanedioic Acid or Dicarboxymethane.
The name is derived from a Greek word Malon which means apple.
Malonates are the ionized form of Carboxyacetic acid (Malonic Acid), along with its esters and salts.
Carboxyacetic acid (Malonic Acid) appears as a white crystal or crystalline powder.
Carboxyacetic acid (Malonic Acid) dissolves in alcohol, pyridine, and ether.
Carboxyacetic acid (Malonic Acid) was first prepared in the year, 1858 by the French chemist Victor Dessaignes by the oxidation of malic acid.
Carboxyacetic acid (Malonic Acid) is found in some fruit’s viz citrus fruits.
The amount of Carboxyacetic acid (Malonic Acid) produced from fruits through organic farming is greater than the fruits grown through conventional agriculture.
Carboxyacetic acid (Malonic Acid) can be produced through the fermentation of glucose.
In addition, Carboxyacetic acid (Malonic Acid) and coenzyme A can be biosynthesized from malonyl-CoA through Carboxyacetic acid (Malonic Acid)s interaction with the enzyme fatty acid synthase.
malonyl/acetyl transferase domain.
An Carboxyacetic acid (Malonic Acid) in which the two carboxy groups are separated by a single methylene group.
In humans, Carboxyacetic acid (Malonic Acid) is involved in fatty acid biosynthesis.
Outside of the human body, Carboxyacetic acid (Malonic Acid) has been detected, but not quantified in, several different foods, such as red beetroots, corns, scarlet beans, common beets, and cow milks.
This could make Carboxyacetic acid (Malonic Acid) a potential biomarker for the consumption of these foods.
Carboxyacetic acid (Malonic Acid), with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, combined malonic and methylCarboxyacetic acid
Carboxyacetic acid (Malonic Acid), and early preeclampsia; Carboxyacetic acid (Malonic Acid) has also been linked to the inborn metabolic disorder malonyl-coa decarboxylase deficiency.
Carboxyacetic acid (Malonic Acid) is a dicarboxylic acid with structural formula CH2(COOH)2 and chemical formula C3H4O4.
The name Carboxyacetic acid (Malonic Acid) originated from the word ‘Malon’ which is Greek for ‘apple’.
Methane Carboxyacetic acid (Malonic Acid) is another name for Carboxyacetic acid (Malonic Acid).
The ester and salts of Carboxyacetic acid (Malonic Acid) are called malonates.
The Carboxyacetic acid (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
Preparation:
Carboxyacetic acid (Malonic Acid) is usually produced from chloroacetic acid.
Reaction: The Carboxyacetic acid (Malonic 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 Carboxyacetic acid (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, Carboxyacetic acid (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 Carboxyacetic acid (Malonic Acid) through these processes is extremely costly and environmentally hazardous.
Uses:
Carboxyacetic acid (Malonic Acid) is used as an intermediate in the manufacture of barbiturates and other pharmaceuticals.
Carboxyacetic acid (Malonic Acid) is a component used as a stabilizer in many high-end cosmetic and pharmaceutical products. Carboxyacetic acid (Malonic Acid) is also used as building block in chemical synthesis, specifically to introduce the molecular group -CH2-COOH.
Carboxyacetic acid (Malonic Acid) is used for the introduction of an acetic acid moiety under mild conditions by Knoevenagel condensation and subsequent decarboxylation.
Carboxyacetic acid (Malonic Acid) is acts as a building block in organic synthesis.
Carboxyacetic acid (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.
Carboxyacetic acid (Malonic Acid) acts as a cross linker in the coating industry and surgical adhesive.
Carboxyacetic acid (Malonic Acid) finds application in the production of specialty chemicals, flavors and fragrances, polymer cross linkers and pharmaceuticals.
Carboxyacetic acid (Malonic Acid) is a precursor to specialty polyesters.
Carboxyacetic acid (Malonic Acid) can be converted into 1,3-propanediol for use in polyesters and polymers (whose usefulness is unclear though).
Carboxyacetic acid (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 Carboxyacetic acid (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.
Carboxyacetic acid (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 Carboxyacetic acid (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, Carboxyacetic acid (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, Carboxyacetic acid (Malonic Acid) can be used to control acidity, either as an excipient in pharmaceutical formulation or natural preservative additive for foods.
Carboxyacetic acid (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.
Carboxyacetic acid (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.
Carboxyacetic acid (Malonic Acid) is a key component in the malonic ester synthesis, a versatile method for introducing a two-carbon unit into a molecule.
The diester derived from Carboxyacetic acid (Malonic Acid) can undergo nucleophilic substitution reactions, providing a pathway for the synthesis of various organic compounds.
Carboxyacetic acid (Malonic Acid) can act as a weak dibasic acid, forming salts and esters.
Carboxyacetic acid (Malonic Acid) is acidic protons make it suitable for reactions involving acid-base chemistry.
The malonic ester synthesis is widely used in the pharmaceutical industry for the synthesis of intermediates that are further transformed into various drugs.
This includes the preparation of barbiturates and other pharmaceutical compounds.
Carboxyacetic acid (Malonic Acid) can be used as an indicator in certain analytical chemistry methods, especially in titrations involving weak acids and bases.
Metal Complex Formation: Carboxyacetic acid (Malonic Acid) can form complexes with various metal ions.
These complexes can have applications in catalysis and other chemical processes.
Carboxyacetic acid (Malonic Acid) derivatives are used in the flavor and fragrance industry to synthesize aroma compounds.
These compounds contribute to the characteristic smells and tastes of certain foods, beverages, and perfumes.
Carboxyacetic acid (Malonic Acid) is often employed in the synthesis of pyrazoles, a class of compounds with diverse applications, including as pharmaceuticals and agrochemicals.
Carboxyacetic acid (Malonic Acid) derivatives are valuable in organic synthesis for the preparation of a variety of compounds, such as acetic acids, keto acids, and amino acids.
Carboxyacetic acid (Malonic Acid) derivatives find application in the dye industry, where they are used in the synthesis of certain dyes and pigments.
Carboxyacetic acid (Malonic Acid) has been used in the preparation of chemicals employed in photographic development processes.
Carboxyacetic acid (Malonic Acid) and its derivatives are commonly used in research laboratories for organic synthesis and as building blocks for the construction of more complex molecules.
Carboxyacetic acid (Malonic Acid) derivatives can be utilized in certain polymerization reactions, contributing to the production of polymers with specific properties.
Carboxyacetic acid (Malonic Acid) can be used as a buffer in certain chemical and biological applications due to its ability to maintain a stable pH.
Carboxyacetic acid (Malonic Acid) is employed in some electroplating processes as a complexing agent for certain metal ions, aiding in the deposition of metal coatings.
Carboxyacetic acid (Malonic Acid) derivatives are commonly employed in the development of new synthetic methodologies and the exploration of organic reaction mechanisms in research settings.
Carboxyacetic acid (Malonic Acid) and its derivatives are used in the synthesis of specialty chemicals, including some that find applications in unique industrial processes.
Carboxyacetic acid (Malonic Acid) can be used in certain chemical analyses and experiments, serving as a reactant or a starting material in laboratory procedures.
Some studies suggest that Carboxyacetic acid (Malonic Acid) may have antioxidant properties, which could have potential applications in health-related research.
Carboxyacetic acid (Malonic Acid) is a precursor to various malonate salts, which have applications in different industries, including the production of certain cleaning agents and detergents.
Safety Profile:
Carboxyacetic acid (Malonic Acid) may cause irritation to the skin, eyes, and mucous membranes.
Carboxyacetic acid (Malonic Acid) is advisable to use appropriate personal protective equipment, such as gloves and safety goggles, when handling this compound.
Ingesting or inhaling Carboxyacetic acid (Malonic Acid) can be harmful.
Carboxyacetic acid (Malonic Acid) is important to avoid these routes of exposure. Ingestion may lead to irritation of the gastrointestinal tract.
Carboxyacetic acid (Malonic Acid) is not combustible on its own, but it may emit irritating or toxic fumes when heated.
Carboxyacetic acid (Malonic Acid) should be stored away from heat sources and open flames.
While Carboxyacetic acid (Malonic Acid) itself is biodegradable, its derivatives and by-products may have different environmental impacts.
Proper disposal practices should be followed to minimize any potential environmental harm.