320-77-4

Basic information

• Product Name: 3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid
• Synonyms: Isocitric acid; 3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid; 3-carboxy-2,3-dideoxypentaric acid
• CAS NO: 320-77-4
• Molecular Formula: C₆H₈O₇
• Molecular Weight: 192.1235
• EINECS: 206-282-3
• Mol File: 320-77-4.mol

Chemical Properties

• Boiling Point: 329.6°C at 760 mmHg
• Flash Point: 167.4°C
• Density: 1.751g/cm³
• Vapor Pressure: 1.3E-05mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: 3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid(320-77-4)
• EPA Substance Registry System: 3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid(320-77-4)

Safety Data

• Hazardous Substances Data: 320-77-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
3-cDDHPTCA is utilized as a building block for the synthesis of complex pharmaceutical molecules, leveraging its unique structure and functional groups to create new compounds with potential therapeutic properties.
Used in Biochemical Research:
In biochemical research, 3-cDDHPTCA serves as a research tool to study the reactivity and behavior of tricarboxylic acids, providing insights into their interactions within chemical and biological systems.
Used in Chemical Synthesis:
3-cDDHPTCA is employed as an intermediate in the synthesis of a variety of chemical compounds, taking advantage of its multiple carboxylic acid functional groups to facilitate the formation of new molecular structures.
Used in Industrial Applications:
3-cDDHPTCA may find use in various industrial applications, such as the development of new materials or the improvement of existing processes, due to its versatile chemical properties and potential for modification and functionalization.

Upstream product

• 585-84-2 cis-aconitic acid 
• 2280-44-6 D-Glucose 
• 492-61-5 β-D-glucose 
• 72-18-4 L-valine 
• 63-68-3 L-methionine 
• 56-87-1 L-lysine 
• 56-84-8 L-Aspartic acid 
• 72-19-5 L-threonine 
• 73-32-5 L-isoleucine 
• 1120-36-1 1-tetradecene 
• 328-50-7 α-ketoglutaric acid 
• 124-38-9 carbon dioxide 
• 56-41-7 L-alanin 
• 544-76-3 Hexadecane 

Downstream Products

• 4702-32-3 (2RS,3SR)-5-oxotetrahydrofuran-2,3-dicarboxylic acid 
• 1948-82-9 oxalosuccinic acid 
• 328-50-7 α-ketoglutaric acid 

Relevant articles and documents

Photocatalytic Fixation of Carbon Dioxide in Oxoglutaric Acid using Isocitrate Dehydrogenase and Cadmium Sulphide

Photocatalytic fixation of CO2 in oxoglutaric acid to yield isocitric acid was investigated with the use of isocitrate dehydrogenase as a catalyst, methyl viologen as an electron mediator and cadmium sulphide as a photocatalyst.The rate of the isocitric acid production depended on the concentration of oxoglutaric acid and methyl viologen, and the rate equation to meet these findungs was derived.The Michaelis-Menten constant determined by using this equation (Km1 and Km2) was 23.9 mmol dm-3 for the substrate and 0.030 mmol dm-3 for the mediator, suggesting that the electron transfer between isocitrate dehydrogenase and the substrate is the rate-determining step.

Cyanide as a primordial reductant enables a protometabolic reductive glyoxylate pathway

Investigation of prebiotic metabolic pathways is predominantly based on abiotically replicating the reductive citric acid cycle. While attractive from a parsimony point of view, attempts using metal/mineral-mediated reductions have produced complex mixtures with inefficient and uncontrolled reactions. Here we show that cyanide acts as a mild and efficient reducing agent mediating abiotic transformations of tricarboxylic acid intermediates and derivatives. The hydrolysis of the cyanide adducts followed by their decarboxylation enables the reduction of oxaloacetate to malate and of fumarate to succinate, whereas pyruvate and α-ketoglutarate themselves are not reduced. In the presence of glyoxylate, malonate and malononitrile, alternative pathways emerge that bypass the challenging reductive carboxylation steps to produce metabolic intermediates and compounds found in meteorites. These results suggest a simpler prebiotic forerunner of today’s metabolism, involving a reductive glyoxylate pathway without oxaloacetate and α-ketoglutarate—implying that the extant metabolic reductive carboxylation chemistries are an evolutionary invention mediated by complex metalloproteins. [Figure not available: see fulltext.].

Photochemical Fixation of Carbon Dioxide: Enzymic Photosynthesis of Malic, Aspartic, Isocitric, and Formic Acids in Artificial Media

Photosensitized regeneration of 1,4-dihydronicotinamide adenine dinucleotide phosphate (NADPH) with an artificial photosystem allows the enzymic fixation of CO2 through carboxylation of α-oxo acids using sacrificial electron donors.Pyruvic acid is carboxylated to malic acid and α-oxoglutaric acid is carboxylated to isocitric acid with the malic enzyme and isocitrate dehydrogenase (ICDH) as biocatalysts, φ=1.9percent.Malic acid formed through the photosensitized process is used as a synthetic building block for subsequent sesquestered enzymic transformations, and its conversion into aspartic acid is accomplished with fumarase and aspartase as biocatalysts.Photoreduction of CO2 to formate is accomplished in the presence of formate dehydrogenase (FDH) as catalyst.Photosensitized reduction of different bipyridinium relay systems, i.e.N,N'-dimethyl-4,4'-bipyridinium (MV(2+)) (1), N,N'-dimethyl-2,2'-bipyridinium (DM(2+)) (2), N,N'-trimethylene-2,2'-bipyridinium (DT(2+)) (3), and N,N'-tetramethylene-2,2'-bipyridinium (DQ(2+)) (4), to the corresponding radical cation yields reduced relays that act as cofactors for FDH, which mediates the reduction of CO2 to formate.The quantum yield for formate formation is in the range φ=0.5-1.6percent.

Role of Methylcitric Acid Cycle in Catabolism of Amino Acids by Saccharomycopsis lipolitica

We examined the production of 2-methylisocitric acid, an intermediate of the constitutive methylcitric acid cycle involved in propionyl-CoA oxidation during the catabolism of different amino acids by a mutant lacking 2-methylisocitrate lyase, a key enzyme of the cycle.The acid was produced equmolarly from isoleucine within a range of amounts of the amino acid added.The amount of the acid produced also increased depending upon the amounts of valine, threonine, methionine, homoserine, and α-aminobutyric acid.However, only a little acid was produced from the 13 other amino acids tested.These results indicated that propionyl-CoA was involved in the catabolism of the first six amino acids named, but not in the other 13.Intramolecular amino acids were therefore part of metabolic turnover and the constitutive cycle functioned in the catabolism of propionyl-CoA derived from the turnover.

Production of Isocitric Acid from Glucose by Candida ravautii

A strain of yeast, No. 325, having been isolated as a threo-Ds-isocitric acid producer and identified as Candida brumptii, was reidentified as Candida ravautii after taxonomical reexamination.All the tested strains of C. ravautii produced mainly isocitric acid.The tested strains were found to be unable to assimilate isocitric acid, although the assimilability of citric acid is one of the taxonomical characteristics of C. ravautii.A mutant was selected as the best producer of isocitric acid in media supplemented with yeast extract: the yield of isocitric acid amounted to about 50percent on the basis of glucose supplied under suitable conditions in shaken culture.

Mode of Metabolism of 1-Tetradecene by Candida Yeasts and Citrates Production

Metabolic pathways for the oxidation of 1-tetradecene by Candida lipolytica were investigated and compared with those for Candida tropicalis in oder to elucidate the difference in the productivity of citrates reported in the previous paper.No difference was found in the pathways for the initial stage of oxidation of 1-tetradecene between the two strains, indicating that the difference in the productivity of citrates is not attributable to the metabolic pathways.The metabolic rate of 1-tetradecene with C. lipolytica was found to be much lower than that with C. tropicalis.The production of citrates was much enhanced in the presence of surfactants which were known to be stimulative for microbial metabolism of hydrocarbons and 11-15 g/liters was attained on the 6th day of cultivation.

Method for the production of novel anhydride polycarboxylates

Novel polyfunctional compounds and a process for their preparation are disclosed. These compounds and their alkali metal salts are useful metal sequestrants and/or detergent builders. Selected compounds are also intermediates useful in the syntheses of aconitic acid as well as isocitric and alloisocitric acids and their lactones. The novel polyfunctional compounds are obtained from the reaction of maleic anhydride with selected active methylene or methane containing compounds.

Reaction of maleic anhydride with active methylene or methine containing compounds

Novel polyfunctional compounds and a process for their preparation are disclosed. These compounds and their alkali metal salts are useful metal sequestrants and/or detergent builders. Selected compounds are also intermediates useful in the syntheses of aconitic acid as well as isocitric and alloisocitric acids and their lactones. The novel polyfunctional compounds are obtained from the reaction of maleic anhydride with selected active methylene or methine containing compounds.

Preparation of cis and trans aconitic acids and their salts

Novel polyfunctional compounds and a novel process for their preparation are disclosed. These compounds may be converted into the acid or salt forms of cis and trans aconitic acids as well as into a racemic mixture of isocitric acid, alloisocitric acid and the lactones of isocitric acid and alloisocitric acid and their salts. All of the acid and salt forms produced are useful as metal sequestrants and/or detergent builders. The novel polyfunctional compounds can also be saponified to their corresponding alkali metal salts which, in turn, are also metal ion seqestering agents and detergent builders. The polyfunctional compounds are the reaction products obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds.