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DIPICOLONIC ACID


EC / List no.: 207-894-3
CAS no.: 499-83-2
Mol. formula: C7H5NO4


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. 
Dipicolinic acid is also used to prepare dipicolinato ligated lanthanide and transition metal complexes for ion chromatography.

Biological role
Dipicolinic composes 5% to 15% of the dry weight of bacterial spores.
Dipicolinic acid 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 Dipicolinic acid 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 Dipicolinic acid based on photoluminescence in the presence of terbium, although this phenomenon was first investigated for using Dipicolinic acid in an assay for terbium by Barela and Sherry.
Extensive subsequent work by numerous scientists has elaborated on and further developed this approach.

Environmental behavior
Simple substituted pyridines vary significantly in environmental fate characteristics, such as volatility, adsorption, and biodegradation.
Dipicolinic acid is among the least volatile, least adsorbed by soil, and most rapidly degraded of the simple pyridines.
A number of studies have confirmed dipicolinic acid is biodegradable in aerobic and anaerobic environments, which is consistent with the widespread occurrence of the compound in nature.
With a high solubility (5g/liter) and limited sorption (estimated Koc = 1.86), utilization of dipicolinic acid as a growth substrate by microorganisms is not limited by bioavailability in nature.


Dipicolinic acid is a pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6. 
Dipicolinic acid has a role as a bacterial metabolite.
Dipicolinic acid is a conjugate acid of a dipicolinate(1-).


Uses of Dipicolinic acid

Dipicolinic acid is released from the autoclave killing of Geobacillus stearothermophilus spores used in biological indicators; 
Dipicolinic acid induces the aggregation of chitosan stabilized gold nanoparticles, causing the solution to change colors varying from red to blue.

Used to prepare dipicolinato ligated lanthanide and transition metal complexes.


Dipicolinic acid, Beauveria sp. 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 recognized 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 sterilization.


About Dipicolinic acid
Helpful information
Dipicolinic acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 to < 100 tonnes per annum.

Dipicolinic acid is used by consumers, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

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 Dipicolinic acid is likely to occur from: indoor use as processing aid.

Article service life
ECHA has no public registered data on the routes by which Dipicolinic acid is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.

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 Dipicolinic acid. Other release to the environment of Dipicolinic acid is likely to occur from: indoor use as processing aid.
Formulation or re-packing
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 Dipicolinic acid can occur from industrial use: formulation of mixtures and formulation in materials.
Uses at industrial sites
Dipicolinic acid is used in the following products: pharmaceuticals.
Dipicolinic acid is used for the manufacture of: chemicals.
Release to the environment of Dipicolinic acid 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.
Manufacture
Release to the environment of Dipicolinic acid can occur from industrial use: manufacturing of the substance.

Dipicolinic Acid is a chemical compound which composes 5% to 15% of the dry weight of bacterial spores. 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. 
Dipicolinic acid is also used to prepare transition metal complexes for ion chromatography.


Dipicolinic acid is a disubstituted pyridine derivative containing two carboxylic acid groups. 
Dipicolinic acid is commonly found in bacterial spores, as it confers heat resistance to the endospore. 
Dipicolinic acid is a powerful complexation agent and has several uses in biochemistry and transition metal chemistry

Properties
Chemical
Dipicolinates are good chelation agents. 
There are multiple free electron pairs on the molecule, one on the lone nitrogen atom and two on oxygen atoms in the carboxylate groups, making it a tridentate ligand.
Numerous metals will complex to the dipicolinate ion, most notably chromium and the lanthanides.

Physical
When dipicolinic acid is added to lanthanide ions, the dipicolinato groups are able to transfer the energy of ultraviolet light to the lanthanide ion, resulting in greater fluorescence. 
By substituting all of the water molecules which normally coordinate to a lanthanide ion, it reduces the absorption of ultraviolet light and fluorescence is enhanced, especially in solution.

Dipicolinic acid melts at 248-250°C.

Availability
Chromium dipicolinate is available as a supplement, but this is an impractical method of producing dipicolinic acid.

Preparation
Dipicolinic acid may be synthesized froom 2,6-dichloropyridine.


Dicarboxylic acids, such as the phthalic acids and their derivatives, are monomeric components in several important polyesters and polyamides. 
In most cases, these compounds are derived from fossil fuels and are not easily biodegradable. 
Dipicolinic acid (DPA) is a biologically derived aromatic di-acid that has a similar structure to isophthalic acid. 
Furthermore, Dipicolinic acid has been shown to make polyesters, is readily biodegradable, and is non-toxic. 
Dipicolinic acid is naturally produced by Bacillus and Clostridium species during sporulation and can comprise up to 15% of the dry weight. 
In this paper we demonstrate the first heterologous production of dipicolinic acid and identify the genes appropriate for gram-scale production in the industrial workhorse organism, E. coli. First, several genetic constructs were designed to identify the genes necessary for recombinant production in E. coli from the aspartate pre-cursor. 
The in vitro activity of dipicolinate synthase was then compared between Bacillus subtilits and Clostridium perfringens. 
Next, in order to improve Dipicolinic acid production from glucose an optimized strain was created containing the elimination of several genes resulting in 5.21 g/L Dipicolinic acid when 5 g/L of aspartate was supplied. 
Then, several aspartate kinsases and dipicolinate synthases were screened for optimal activity in E. coli. 
The optimal genes were combined with the overexpression of phosphoenolpyruvate carboxylase, developing a full biosynthetic pathway capable of producing a titer of 4.7 g/L Dipicolinic acid directly from glucose. 


Dipicolinic acid are active in the metabolism of body. 
Application: Syntheses Materials Intermediates; Pharmaceutical Raw Intermediates

Storage Condition: Store in a cool, dry place. Keep container closed when not in use.

Dipicolinic acid is used in the preparation of dipicolinato ligated lanthanide and transition metal complexes. 
Dipicolinic acid 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. 
Dipicolinic acid plays an important role as a marker for the effectiveness of sterilization.


 An amphoteric polar metabolite produced by many bacterial and fungal species; a microbial metabolite; dipicolinic acid had long been recognised as a chelating agent for many metal ions; reaches high concentrations (~10% w/w) in bacillus endospores aiding

Dipicolinic acid Usage
1. Used as a competitive inhibitor of bovine liver glutamate dehydrogenase
2.Ligand complex for the preparation of dipicolinato(R) and transition metals

Product Name: Dipicolinic acid
CAS: 499-83-2
Molecular Formula:C7H5NO4
Molecular weight:167.12
EINECS: 207-894-3
Melting point 248-250 °C (dec.)(lit.)
Boiling point 295.67°C (rough estimate)
density 1.5216 (rough estimate)
vapor pressure <0.01 hPa (20 °C)
refractive index 1.6280 (estimate)

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.

Dipicolinic acid is a pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.
Dipicolinic acid has a role as a bacterial metabolite. 
Dipicolinic acid is a conjugate acid of a dipicolinate(1-). 


Chemical Properties: White crystalline powder
Uses: Used to prepare dipicolinato ligated lanthanide1 and transition metal2 complexes.
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.

IUPAC NAMES
2,6-PYRIDINEDICARBOXYLIC ACID
2,6-Pyridinedicarboxylic Acid
2,6-Pyridinedicarboxylic AcidPyridin-2,6-dicarbonsäurePyridine-2,6-dicarboxylic Acid
Dipicolinic acid
Pyridin-2,6-dicarbonsäure
Pyridine-2,6-dicarboxylic Acid
Pyridine-2,6-dicarboxylic acid
pyridine-2,6-dicarboxylic acid

SYNONYMS:
2,6-Pyridinedicarboxylic acid
499-83-2
PYRIDINE-2,6-DICARBOXYLIC ACID
Dipicolinic acid
2,6-Dipicolinic acid
Dipicolinate
2,6-Dicarboxypyridine
MFCD00006299
UNII-UE81S5CQ0G
2,6-pyridinedicarboxylate
DPAC
UE81S5CQ0G
CHEMBL28410
2,6-pyridine dicarboxylic acid
CHEBI:46837
2,6-Pyridinedicarboxylic acid, 99%
2,6-pyridinedicarboxylic acid (dipicolinic acid)
NSC 176
EINECS 207-894-3
pyridine-2
pydcH2
PubChem8067
4ih3
ACMC-20aiw4
pyridine carboxylate, 6d
DSSTox_CID_2043
DSSTox_RID_76466
DSSTox_GSID_22043
Oprea1_533632
SCHEMBL34595
MLS000080748
pyridine-2,6-dicarboxlic acid
ARONIS021542
IFLab1_001781
NSC176
DTXSID7022043
BDBM26116
2,6-DI-CARBOXY-PYRIDINE
NSC-176
Pyridinedicarboxylic acid-(2,6)
2,6-Pyridinedicarboxylic acid-2,6-dipicolinic acid
SR-01000600024-2
W-105996
L-042,134
Z57202012
B63A70CE-B9AB-4EA2-834A-6C7634226BB0
F0451-0137
2,6-Pyridinedicarboxylic acid, for ion chromatography, >=99.5% (T)
2,6-Pyridinedicarboxylic acid concentrate, 0.02 M C7H5NO4 in water (0.04N), for ion chromatography, eluent concentrate
Pyridine-2,6-dicarboxylic acid 98%
2,6-Pyridinedicarboxylic acid solution, Eluent concentrate for IC, 0.02M in water
2,6-PyridinedicarboxylicAcid99%
Pyridine-2,6-dicarboxylicacid,98%
IFLAB-BB F0451-0137
LABOTEST-BB LT00848023
RARECHEM AL BO 1335
PYRIDINE-2,6-DICARBOXYLIC ACID
2,6-Dicarboxypyridine
2,6-Pyridinedicarboxylic acid-2,6-dipicolinic acid
dipicolinic
Pyridinedicarboxylic acid-(2,6)
JACS-499-83-2
2,6-Pyridinedicarboxylic acid 99%
2,6-Pyridinedicarboxylic Acid(DPA)
2,6-Pyridinedicarboxylic acid concentrate
Dipicolinic Acid 〔Pyridine-2,6-dicarboxylic Acid〕
Pyridine-2,6-dicarboxylic acid for synthesis
2,6-DIPICOLINIC ACID
2,6-PYRIDINEDICARBOXYLIC ACID
AKOS 2002
DIPICOLINIC ACID
'DIPICOLINIC ACID'
6-Pyridinedicarboxylic acid
2,6-PyridinedicarboxyL
2,6-PYRIDINECARBOXYLIC ACID
DIPLCOLINIC ACID OR PYRIDINE-2,6-DCA PYRIDINE-2,6-DICARBOXYLIC ACID
2,6-PYRIDINEDICARBOXYLIC ACID (DIPICOLINIC ACID)
PYRIDINE-2,6-DICARBOXYLIC ACID extrapure
2,6-Pyridinedicarboxylic acid solution
Dipicolinic acid solution
6-Carboxypicolinic acid
L-042134
Pyridine-2,6-biscarboxylic acid
Pyridine-2,6-dicarboxylate
2,6-Pyridine Dicarboxylic Acid 98% Min
2,6-Pyridinedicarboxylic acid, 99% 100GR
2,6-Pyridinedicarboxylic acid, 99% 25GR
2,6-Pyridinedicarboxylic acid, 99% 500GR
2,6-Pyridinedicarboxylic acid , Pyridine-2,6-dicarboxylic acid
PYRIDINE-2,6-DICARBOXYLIC ACID FOR SYNTH
2,6-Pyridin-dicarboxylic acid
Pyridinedicarboxylic aci
2,6-PyridinedicarboxylicAcid>
ipicolinicaci
2,6-Pyridinedicarboxylic acid ISO 9001:2015 REACH
Pyridine-2,6-dimethyl acid
2,6-Pyridinedicarboxylic acida


 

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