DIPICOLINIC ACID

Table of Contents

DIPICOLINIC ACID

Dipicolinic acid = 2,6-DIPICOLINIC ACID = Pyridine-2,6-dicarboxylic acid = 2,6-Pyridinedicarboxylic acid = PDC = DPA

Preferred IUPAC name: Pyridine-2,6-dicarboxylic acid

Other names: 2,6-Pyridinedicarboxylic acid

Identifiers

CAS Number: 499-83-2 

EC Number: 207-894-3

Pyridine-2,6-dicarboxylic acid

IUPAC names

2,6-PYRIDINEDICARBOXYLIC ACID

2,6-Pyridinedicarboxylic Acid

Pyridin-2,6-dicarbonsäure

Dipicolinic acid

Trade names

2,6-DIPICOLINIC ACID

Registration dossier

Dipicolinic acid

Molecular formula: C7H5NO4

Molecular Weight: 167.12

Beilstein/REAXYS Number: 131629

MDL number:MFCD00006299

eCl@ss: 39151816

PubChem Substance ID: 24898760

NACRES: NA.22

Properties

Chemical formula: C7H5NO4

Molar mass: 167.120 g·mol−1

Melting point: 248 to 250 °C (478 to 482 °F; 521 to 523 K)

Hazards

Main hazards: Irritant (Xi)

R-phrases (outdated): R36/37/38

S-phrases (outdated): S26 S36

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.

Dipicolinic acid is used in sterilising solutions to control the growth of microorganisms in food products.

Dipicolinic acid can be used in the antimicrobial agent which is intended for use in meat, poultry (as well as brines, sauces, and marinades used on poultry and pre-formed meat and poultry products), fish and seafood, egg wash, seeds and nuts, and fruit and vegetable processing plants.

Dipicolinic acid stabilizes peroxyacid equilibrium mixtures during storage for use on red meat.

Dipicolinic acid is a pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6. 

Dipicolinic acid has a role as a bacterial metabolite. 

It is a conjugate acid of a dipicolinate(1-).

Dipicolinic acid is 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 is raw material for a series of novel Schiff bases for antioxidant and iron chelating activity. 

In most cases Schiff bases derived from di-hydrazide showed higher antioxidant activity than the ones derived from mono-hydrazide and some of them are very promising considering the fact of being better antioxidants than the standards used in the investigation. 

For iron chelating activity substituents had a greater impact on the activity than mono or di-hydrazide skeleton.

Keywords: Antioxidant, dipicolinic acid, metal chelating, Schiff base, Clostridium, Bacillus, antibacterial, antifungal, antitumor, pharmaceutical

Applications of Dipicolinic acid

Intended Use of Dipicolinic acid: To stabilize peroxyacid equilibrium mixtures during storage (i.e., before dilution with water and subsequent use on food), for use on red meats such as beef and pork.

Limitations/Specifications: To be used at a maximum level of 0.7 ppm in the wash water.

Intended Use: To stabilize peroxyacid equilibrium mixtures during storage (i.e. before dilution with water and subsequent food-contact use, except for use in contact with infant formula or human milk (see Limitations/Specifications)).

Limitations/Specifications: To be used in peroxyacetic acid solutions authorized in effective Food Contact Notifications with the following limitations in use level for:meat carcasses, parts, trim, and organs at a maximum use level of 1.64 ppmpoultry carcasses, parts, trim, and organs at a maximum use level of 4.00 ppmprocessed and preformed meat and poultry at a maximum use level of 0.44 ppmfruits and vegetables in food processing facilities at a maximum use level of 0.68 ppmfish and seafood at a maximum use level of 0.38 ppmbrines, sauces, and marinades at a maximum use level of 0.10 ppm, andthe commercial sterilization of aseptic filling systems, glass and plastic food packaging and their enclosures prior to filling at a maximum use level of 9.0 ppm. 

If the peroxyacetic acid solution is applied at a rate exceeding 0.0175 milliliters treatment solution per ounce container capacity, the solution must be drained from the container and rinsed with sterile water and drained again. FDAs review of the use of the FCS in aseptic filling systems is limited to the extent that the FCS residues may transfer from the non-food contact surfaces of the aseptic filling system to food packaging materials. 

The FCS is not for use on food packaging used in contact with infant formula or human milk or on aseptic filling equipment used to fill such packaging. 

Such uses were not included as part of the intended use of the substance in the FCN.

Dipicolinic acid is used for rapidly preparing high-concentration peroxyacetic acid.

2,6-Pyridinedicarboxylic acid is used as organocatalyst for the synthesis of 1,5-benzodiazepines

2,6-Pyridinedicarboxylic acid has been found to be an effective and efficient organocatalyst for the synthesis of 1,5-benzodiazepine derivatives from o-phenylenediamine, β-ketoesters, and aromatic aldehydes by employing one-pot three-component reaction. 

As the catalyst, Dipicolinic acid plays a crucial role for the regioselective C–C bond formation at the γ position of β-ketoesters. 

The salient features of this present protocol are simple reaction procedure, requirement of cost-effective catalyst, good yields, and applicable to a wide range of substrates.

Antifungal Mechanism of Dipicolinic Acid helps for the Biocontrol of Pear Valsa Canker

Dipicolinic acid (DPA) is a major component of Bacillus spores and was first found to exhibit low millimolar inhibition for GR from Bacillus subtilis (Spies et al., 2009)

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, although this phenomenon was first investigated for using DPA in an assay for terbium by Barela and Sherry.

Extensive subsequent work by numerous scientists has elaborated on and further developed this approach.

Dipicolinic Acid is used for Spore Detection: Dipicolinic is used to determine the number of endospores in sediments and cultures. 

The method is based on the fluorimetric determination of dipicolinic acid (DPA), a spore core-specific compound, after reaction with terbium chloride. 

The concentration of dipicolinic acid in natural samples is converted into endospore numbers using endospore-forming pure cultures as standards. 

Quenching of the fluorescence by sediment constituents and background fluorescence due to humic substances hampered direct determination of dipicolinic acid in sediments.

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.

Uses

2,6-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.

Chemical Properties

White crystalline powder

Uses

Used to prepare dipicolinato ligated lanthanide1 and transition metal2 complexes.

Uses

2,6-Dipicolinic Acid 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.

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.

It has been shown that Dipicolinic Acid, a polysubstituted pyridine derivative readily biodegrades under both aerobic and anaerobic conditions.

In presenting a review on the microbial metabolism of pyridines, including DPA, Kaiser, et al. describe aerobic metabolism of DPA to carbon dioxide, ammonium, and water, and anaerobic metabolism to dihydroxypyridine which is then rapidly photodegraded to organic acids (i.e., propionic acid, acetic acid), carbon dioxide, and ammonium. 

DIPICOLINIC ACID IS USED IN THE MIXTURES OF ANTI MICROBIAL AGENTS IN PROCESS WATERS 

Dipicolinic acid is used in food contact substance (FCS), an equilibrium mixture of peroxyacetic acid, hydrogen peroxide, acetic acid, l-hydroxyethylidine-1,1-diphosphonic acid (HEDP), dipicolinic acid, and sulfuric acid as an antimicrobial agent in process water applied as a spray, wash, rinse, dip, chiller water, low-temperature (e.g., less than 40 F) immersion baths, or scald water for whole or cut poultry carcasses, parts, and trim.

The components of the FCS mixture will not exceed: 2000 parts per million (ppm)peroxyacetic acid (PAA), 403 ppm hydrogen peroxide (HP), 5 ppm HEDP, and 0.88 ppm dipicolinic acid in spray, wash, rinse, dip, chiller water, low-temperature (e.g., less than 40 F) immersion baths, or scald water for whole or cut poultry carcasses, parts, and trim.

Mixtures containing these substances have previously been cleared by other Notifiers for the same uses. 

However, this formulation at use has lower amounts of hydrogen peroxide, HEDP, and dipicolinic acid (DPA), which results in lower releases to the environment. 

The antimicrobial effect of peroxyacetic acid reduces or eliminates populations of pathogenic and nonpathogenic microorganisms that may be present on the food. 

In poultry processing, particularly, industry has now added “finishing chillers” in order to treat the pathogen Campylobacter more effectively.

Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. 

(See all compounds classified as Enzyme Inhibitors.)

Medical Subject Headings (MeSH)

Chelating Agents

Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. 

(See all compounds classified as Chelating Agents.)

Other names: Dipicolinic acid; DPac; 2,6-Dicarboxypyridine; 2,6-Dipicolinic Acid; Pyridine-2,6-dicarboxylic acid; 2,6-Pyridinedicarboxylic acid-2,6-dipicolinic acid; Pyridinedicarboxylic acid-(2,6); DPA

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

CHEMBL284104

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)

HMS1417A21

HMS2231H20

ZINC105246

ACN-S002679

ACT07463

Tox21_301129

AC-704

ANW-75410

BBL012080

CCG-44216

CL0252

SBB028480

STK092939

AKOS000112829

AM82010

DB04267

MCULE-1484050836

PS-8736

NCGC00071864-02

NCGC00255028-01

AK-49834

CAS-499-83-2

SMR000034075

ST040658

SY001460

DB-015930

A7431

CS-0016012

EU-0033484

FT-0610741

P0554

M-5988

Q417164

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

Dipicolinic Acid Fate in the Environment

Information in the scientific literature indicates that DPA, a disubstituted pyridine, readily biodegrades in fresh and marine water, and in soil under both aerobic and anaerobic conditions.

In presenting a review on the microbial metabolism of pyridines, including dipicolinic acid, Kaiser, et al. describe aerobic metabolism of dipicolinic acid to carbon dioxide, ammonium, and water, and anaerobic metabolism to dihydroxypyridine which then rapidly photodegrades to organic acids (i.e., propionic acid, acetic acid), carbon dioxide, and ammonium.

Further information indicates that dipicolinic acid is soluble in water, with the estimated water solubility of 5,000 mg/L and an octanol-water partition coefficient estimated to be 0.57. 

Based upon this information, it is reasonable to conclude that dipicolinic acid will remain substantially with water and not be absorbed to sludge, and that dipicolinic acid will be readily biodegraded during treatment at POTWs and on-site treatment facilities.

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Pyridinedicarboxylic acid is a group of organic compounds which are dicarboxylic derivatives of pyridine. Pyridinedicarboxylic acid comes in several isomers:

Quinolinic acid (2,3-pyridinedicarboxylic acid)

Lutidinic acid (2,4-pyridinedicarboxylic acid)

Isocinchomeronic acid (2,5-pyridinedicarboxylic acid)

Dipicolinic acid (2,6-pyridinedicarboxylic acid)

Cinchomeronic acid (3,4-pyridinedicarboxylic acid)

Dinicotinic acid (3,5-pyridinedicarboxylic acid)

Synonyms: 

2,6-Dicarboxypyridine

2,6-Dipicolinate

2,6-Dipicolinic acid

2,6-Pyridinedicarboxylate

Dipicolinate biospider

Dipicolinic acid

PYRIDINE-2,6-dicarboxylate

Pyridine-2,6-dicarboxylic acid

131629 [Beilstein]

2,6-Dipicolinic acid

2,6-Pyridindicarbonsäure [German] [ACD/IUPAC Name]

2,6-PYRIDINE DICARBOXYLIC ACID

2,6-Pyridinedicarboxylic acid [ACD/Index Name] [ACD/IUPAC Name]

2,6-Pyridinedicarboxylic acid solution

207-894-3 [EINECS]

499-83-2 [RN]

Acide 2,6-pyridinedicarboxylique [French] [ACD/IUPAC Name]

acide pyridine-2,6-dicarboxylique [French]

Dipicolinic acid [Wiki]

Dipicolinic acid solution

DPA

DPAC

Pyridine-2,6-dicarboxylic acid

T6NJ BVQ FVQ [WLN]

UE81S5CQ0G

[499-83-2]

2, 6-Pyridinedicarboxylic acid

2,6-Dicarboxypyridine

2,6-DI-CARBOXY-PYRIDINE

2,6-Pyridine-Dicarboxylic Acid

2,6-Pyridinedicarboxylic acid (Dipicolinic acid)

2,6-Pyridinedicarboxylic Acid (en)

2,6-pyridinedicarboxylic acid 98%

2,6-Pyridinedicarboxylic acid concentrate

2,6-pyridinedicarboxylic acid, 99%

2,6-pyridinedicarboxylic acid,99%

2.6-???????????????

2.6-吡啶二甲酸

95-68-1 [RN]

ARONIS021542

BR-49834

C7H5NO4

CHEBI:46837

EINECS 207-894-3

http:////www.amadischem.com/proen/535359/

http://www.hmdb.ca/metabolites/HMDB0033161

https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:46837

InChI=1/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12

L-042,134

MFCD00474575

Oprea1_533632

PDC

PS-8736

PY-7340

pyridine 2,6-dicarboxylic acid, ???98%

pyridine-2,6-dicarboxlic acid????????????

pyridine-2,6-dicarboxylic acid, 98%

Pyridine-2,6-dicarboxylic acid|2,6-Dipicolinic acid

SR-01000600024-2

UNII:UE81S5CQ0G

UNII-UE81S5CQ0G

ジピコリン酸 [Japanese]

2,6-Pyridinedicarboxylic acid Chemical Properties, Uses and Production

Definition

ChEBI: A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.

2,6-Pyridinedicarboxylic acid Preparation Products And Raw materials

Raw materials

2,6-Lutidine Ethyl acetate Potassium permanganate Sulfuric acid Heptanedioic acid, 2,6-dioxo- 6-Methyl-2-pyridinecarboxaldehyde 6-(4-FLUOROPHENYL)PYRIDINE-2-CARBALDEHYDE dichromic acid DIMETHYL PIMELATE trans-Cinnamic acid

Preparation Products

2,6-Pyridinedicarboxylic acid chloride DIMETHYL 4-CHLOROPYRIDINE-2,6-DICARBOXYLATE Methyl 6-methoxyformamido-4-chloropyridin-2-ylcarbamate ,97% 2,6-DIAMINO-4-CHLOROPYRIDINE ETHYL 6-(HYDROXYMETHYL)PYRIDINE-2-CARBOXYLATE 4-CHLOROPYRIDINE-2,6-DICARBOHYDRAZIDE 2,6-Diacetylpyridine 4-CHLORO-PYRIDINE-2,6-DICARBOXYLIC ACID 6-(TERT-BUTOXYCARBONYLAMINO-METHYL)-PYRIDINE-2-CARBOXYLIC ACID ETHYL 6-(CHLOROMETHYL)PYRIDINE-2-CARBOXYLATE 6-(AMINOMETHYL)PYRIDINE-2-CARBOHYDRAZIDE 6-(AMINOMETHYL)-2-PYRIDINE CARBOXYLIC ACID DIMETHYL 2,6-PYRIDINEDICARBOXYLATE

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