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Dipicolinic acid (pyridine-2,6-dicarboxylic acid or PDC and DPA) is a chemical compound which plays a role in the heat resistance of bacterial endospores. It is also used to prepare dipicolinato ligated lanthanide and transition metal complexes for ion chromatography.
CAS Number: 499-83-2
EC Number: 207-894-3
IUPAC Name: Pyridine-2,6-dicarboxylic acid
Chemical Formula: C7H5NO4
Other names: 2,6-Pyridinedicarboxylic acid, 499-83-2, PYRIDINE-2,6-DICARBOXYLIC ACID, Dipicolinic acid, 2,6-pyridinedicarboxylate, NSC 176, UNII-UE81S5CQ0G, EINECS 207-894-3, DTXSID7022043, CHEBI:46837, NSC-176, 2,6-DIPICLINIC ACID, 6-CARBOXYPICOLINIC ACID, DTXCID602043, 2,6-DI-CARBOXY-PYRIDINE, Pyridinedicarboxylic acid-(2,6), zinc dipicolinate, 2,6-Pyridinedicarboxylic acid-2,6-dipicolinic acid, calcium dipicolinic acid, 3,4-pyridinedicarboxylate, dipicolinic acid, zinc salt, dipicolinic acid, calcium salt, dipicolinic acid, disodium salt, dipicolinic acid, monosodium salt, dipicolinic acid, dipotassium salt, 2,6-Dipicolinate, 2,6Dipicolinic acid, Pyridine2,6dicarboxylic acid, inchi=1/c7h5no4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3h,(h,9,10)(h,11,12, wjjmndumqpnecx-uhfffaoysa-n, 2,6-Dipicolinic acid, Dipicolinate, 2,6-Dicarboxypyridine, MFCD00006299, UE81S5CQ0G, CHEMBL284104, 2,6-Pyridinedicarboxylic acid, 99%, 2,6-pyridine dicarboxylic acid, pyridine-2, pydcH2, Dipicolinic acid;DPA, 4ih3, pyridine carboxylate, 6d, pyridine, 2,6-dicarboxy-, 2,6-pyridinedicarboxylic acid (dipicolinic acid), Oprea1_533632, SCHEMBL34595, MLS000080748, IFLab1_001781, NSC176, Dipicolinic acid, Beauveria sp., BDBM26116, HMS1417A21, HMS2231H20, HY-Y1024, Tox21_301129, AC-704, BBL012080, CCG-44216, CL0252, STK092939, PYRIDINE-2,6-DICARBOXYLICACID, AKOS000112829, DB04267, FP34525, PS-8736, NCGC00071864-02, NCGC00255028-01, CAS-499-83-2, SMR000034075, SY001460, DB-015930, CS-0016012, EU-0033484, NS00013573, P0554, EN300-18133, Q417164, SR-01000600024-2, L-042,134, Z57202012, B63A70CE-B9AB-4EA2-834A-6C7634226BB0, F0451-0137, 2,6-Pyridinedicarboxylic acid, for ion chromatography, >=99.5% (T)
Biological role
Dipicolinic composes 5% to 15% of the dry weight of bacterial spores.
It has been implicated as responsible for the heat resistance of the endospore, although mutants resistant to heat but lacking dipicolinic acid have been isolated, suggesting other mechanisms contributing to heat resistance are at work.
Two genera of bacterial pathogens are known to produce endospores: the aerobic Bacillus and anaerobic Clostridium.
Dipicolinic acid forms a complex with calcium ions within the endospore core. This complex binds free water molecules, causing dehydration of the spore. As a result, the heat resistance of macromolecules within the core increases. The calcium-dipicolinic acid complex also functions to protect DNA from heat denaturation by inserting itself between the nucleobases, thereby increasing the stability of DNA.
The high concentration of DPA in and specificity to bacterial endospores has long made it a prime target in analytical methods for the detection and measurement of bacterial endospores. A particularly important development in this area was the demonstration by Rosen et al. of an assay for DPA based on photoluminescence in the presence of terbium,[8] although this phenomenon was first investigated for using DPA in an assay for terbium by Barela and Sherry.[9] Extensive subsequent work by numerous scientists has elaborated on and further developed this approach.
Consumer Uses
Dipicolinic acid is used in the following products: cosmetics and personal care products, biocides (e.g. disinfectants, pest control products) and washing & cleaning products.
Other release to the environment of this substance is likely to occur from: indoor use as processing aid.
Widespread uses by professional workers
Dipicolinic acid is used in the following products: cosmetics and personal care products. ECHA has no public registered data on the types of manufacture using this substance. Other release to the environment of this substance is likely to occur from: indoor use as processing aid.
Formulation
Dipicolinic acid is used in the following products: biocides (e.g. disinfectants, pest control products), paper chemicals and dyes, pharmaceuticals and cosmetics and personal care products.
Release to the environment of this substance can occur from industrial use: formulation of mixtures and formulation in materials.
Uses at industry
Dipicolinic acid is used in the following products: pharmaceuticals.
Dipicolinic acid is used for the manufacture of: chemicals.
Release to the environment of this substance can occur from industrial use: in processing aids at industrial sites, in the production of articles, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid, for thermoplastic manufacture, as processing aid and of substances in closed systems with minimal release.
Physical State :Solid
Solubility :Soluble in Water: 1%
Storage :Store at room temperature
Melting Point :248-250° C (lit.)(dec.)
Boiling Point :~463.7° C at 760 mmHg (Predicted)
Density :~1.6 g/cm3 (Predicted)
Refractive Index :n20D 1.63 (Predicted)
Dipicolinic acid is used in the preparation of dipicolinate ligated lanthanide and transition metal complexes.
It acts as a chelating agent for chromium, zinc, manganese, copper, iron and molybdenum. Its calcium-dipcolinic acid complex is used to protect deoxyribonucleic acid (DNA) from heat denaturation which enhances the DNA stability. It plays an important role as a marker for the effectiveness of sterilization.
Dipicolinic Acid is a chemical compound that causes the heat resistance of the endospore. The bacteria anaerobic Clostridium and aerobic Bacillus are known to produce endospores. It is also used to prepare lanthanide and transition metal complexes for ion chromatography. Ungraded products supplied by Spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use.
Dipicolinic Acid is released from the autoclave killing of Geobacillus stearothermophilus spores used in biological indicators; It induces the aggregation of chitosan stabilized gold nanoparticles, causing the solution to change colors varying from red to blue.
Used as a competitive inhibitor of bovine liver glutamate dehydrogenase
Ligand complex for preparing dipicolinato lanthanum and transition metal
Description
Dipicolinic acid forms a complex with calcium ions within the endospore core. This complex binds free water molecules, causing dehydration of the spore. As a result, the heat resistance of macromolecules within the core increases.
Application
D 2347 (OTTO) 2,6-Dipicolinic acid, 99% Cas no 499-83-2 - used to prepare dipicolinato ligated lanthanide and transition metal complexes for ion chromatography.
USES
Includes food packaging, paper plates, cutlery, small appliances such as roasters, etc.; does not include facilities that manufacture food *Type of pesticide used to destroy or inhibit the growth of disease-causing mechanisms, can be impregnated into clothing
Inert ingredients in a pesticide
Includes preservatives used in cosmetics, film, wood preserving agents, foods, etc (note food preservatives are also indicated as food_additive)
Dipicolinic acid is a pyridinedicarboxylic acid carrying two carboxyl groups at positions 2 and 6. It has a role as a bacterial metabolite. It is a conjugate acid of a dipicolinate.
Dipicolinic acids are interesting oxido pincer ligands with an O,N,O donor set. They are derived from the potentially O,N,O tridentate binding 2,6-dicarboxylic acid (pydicH2) (Scheme 1).Dipicolinic acid (pydic2−) is a frequently used ligand and coordinates are usually in a deprotonated tridentate mode. The coordinates use the N donor atom and the two carboxylate O donor functions, including the possibility of bridging (Scheme 1) [1–14]. In contrast to this, the pydic ester ligands are neutral and have three options of tris-chelate O,N,O binding, which gives rise to three different isomers Ocarbonyl–M–Ocarbonyl (CC isomer), Ocarbonyl–M–Oalkoxy (CA isomer), and Oalkoxy–M–Oalkoxy (AA isomer)while a bridging mode observed frequently for pydic2− is less probable.
Used for transition metal ions, organic peroxides. Also be used as enzyme inhibitor in biochemistry. Used as a bifunctional monomer and a pharmaceutical intermediate.
Dipicolinic acid, also known as 2,6-dipicolinic acid or 2,6-dicarboxypyridine, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. 2,6-Pyridinedicarboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Dipicolinic acid is used in the preparation of dipicolinato ligated lanthanide and transition metal complexes. It acts as a chelating agent for chromium, zinc, manganese, copper, iron and molybdenum. Its calcium-dipcolinic acid complex is used to protect deoxyribonucleic acid (DNA) from heat denaturation which enhances the DNA stability. It plays an important role as a marker for the effectiveness of sterilization.
Uses
Used to prepare dipicolinato ligated lanthanide1 and transition metal2 complexes.
Uses
Dipicolinic acid is an amphoteric polar metabolite produced by many bacterial and fungal species. Prior to its discovery as a microbial metabolite, dipicolinic acid had long been recognised as a chelating agent for many metal ions. Wide distribution of dipicolinic acid among microbes makes it an important dereplication standard in discovery.
Dipicolinic acid reaches high concentrations (~10% w/w) in Bacillus endospores aiding heat resistance and is used in laboratories as a marker for the effectiveness of sterilisation.
Dipicolinic acid is used in the preparation of dipicolinato ligated lanthanide and transition metal complexes.
Its calcium-dipcolinic acid complex is used to protect deoxyribonucleic acid (DNA) from heat denaturation which enhances the DNA stability.
Dipicolinic acid is active in the metabolism of body. For example, nicotinic acid (3-pyridinecarboxylic acid) is is a constituent of the redox coenzymes nicotinamide adenine dinucleotide and nicotinamide adenine dinucleotide phosphate which are essential in energy metabolism in the living cell.
Dipicolinic acid act as chelating agents of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the body. They are involved in phenylalanine, tryptophan, and alkaloids production, and for the quantitative detection of calcium. This forms a complex with zinc, may facilitate the passage of zinc through the gastrointestinal wall and into the circulatory system.
Dipicolinic acid reacts with hemoglobin and myoglobin, which provide an application in meat processing to form brighter colour. It acts to reduce plasma cholesterol, as a vasodilator and to treat pellagra. It is used for the prophylaxis.
Dipicolinic acids and their derivatives can be studied for these effects. They used as intermediate to produce pharmaceuticals and metal salts for the application of nutritional supplements. Quinolinic acid inhibits glucose synthesis.
Dipicolinic acid inhibits dopamine beta-hydroxylase activity.
Dipicolinic acids are very important in industrial field as well as in bio chemistry. Nucleotide consist of either a nitrogenous heterocyclic base (purine or pyrimidine). Three major pyrimidines in living systems are cytosine, thymine, and uracil.
Dipicolinic acids are biologically important components of nucleic acids (DNA, RNA) and coenzymes. Some pyridine system is active in the metabolism in the body. Certain nitrogenous plant products also have pyridine class compounds. They can be the parent compound of many drugs, including the barbiturates.
Dipicolinic acids are used as solvents and starting material for the synthesis of target compounds such as insecticides, herbicides, medicines, vitamins, food flavorings, feed additives, dyes, rubber chemicals, explosives, disinfectants, and adhesives.
Dipicolinic acid is also used as a denaturant for antifreeze mixtures, as a dyeing assistant in textiles and in fungicides.
