Dipicolinic acid

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Structural formula
Structural formula of dipicolinic acid
General
Surname Dipicolinic acid
other names
  • Pyridine-2,6-dicarboxylic acid
  • DPA
  • PDC
  • 2,6-DICARBOXYPYRIDINE ( INCI )
Molecular formula C 7 H 5 NO 4
Brief description

colorless, almost odorless needles

External identifiers / databases
CAS number 499-83-2
EC number 207-894-3
ECHA InfoCard 100.007.178
PubChem 10367
ChemSpider 9940
DrugBank DB04267
Wikidata Q417164
properties
Molar mass 167.10 g mol −1
Physical state

firmly

Melting point

Decomposition from 248 ° C

pK s value
  • pK s 1 (25 ° C) = 2.17
  • pK s 2 (25 ° C) = 4.97
solubility
  • poor in water (5 g l −1 at 20 ° C)
  • soluble in alkalis
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 302 + 352-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dipicolinic acid ( pyridine-2,6-dicarboxylic acid ) is an organic compound that belongs to the heterocycles (more precisely: heteroaromatic compounds ). It belongs to the group of pyridinedicarboxylic acids and consists of a pyridine ring that has two carboxy groups in the 2- and 6-position. The name is derived from picolinic acid ( pyridine-2-carboxylic acid ), which has only one carboxy group in the 2-position on the pyridine ring .

Occurrence and representation

The compound is a substance that is formed by microorganisms during sporulation (spore formation) . It occurs only in the nucleus (spore protoplasts) of endospores (5–15% of dry weight), but is not contained in vegetative cells.

A representation takes place z. B. from 2,6-lutidine by oxidation of the methyl groups .

properties

When heated, it decomposes from 248 ° C through decarboxylation to picolinic acid :

Decarboxylation

Biological importance

Dipicolinic acid is responsible for the thermal resistance of some bacteria and is often present as a chelate with calcium ions (Ca 2+ ).

use

Dipicolinic acid is used in the chemical industry for the preparation of lanthanoids bound with dipicolin (as a chelating ligand ) and as a complexing agent for transition metal complexes as well as a stabilizer for peroxides and as an intermediate product for the production of other chemical compounds.

Individual evidence

  1. ↑ Entry on 2,6-DICARBOXYPYRIDINE in the CosIng database of the EU Commission, accessed on June 27, 2020.
  2. ↑ a b Entry on dipicolinic acid. In: Römpp Online . Georg Thieme Verlag, accessed on July 28, 2014.
  3. ↑ a b c d e f Entry on pyridine-2,6-dicarboxylic acid in the GESTIS substance database of the IFA , accessed on February 18, 2017(JavaScript required) .
  4. ↑ a b D'Ans-Lax: Pocket book for chemists and physicists. 3rd edition, Volume 1, Springer-Verlag, Berlin-Göttingen-Heidelberg 1967 ( ChemieOnline - pK b and pK s values ).
  5. ↑ H. Höffeler: Bildatlas cytology. Harri Deutsch Verlag, Frankfurt / Main 2003, ISBN 3-8171-1685-3 , p. 39.
  6. ↑ Rainer Bültermann: Investigations into the heat resistance of bacterial spores and the pasteurization of foodstuffs with germs on the surface . Karlsruhe 1997, DNB  1014057590 , urn : nbn: de: swb: 90-AAA3161973 (dissertation, University of Karlsruhe).
  7. ↑ Jörg Fichtel: Determination of the proportion of endospores in the microbial community in tidal flats: = Determination of the abundance of endospores within the microbial community in tidal flat sediments . Oldenburg 2008, DNB  989264467 , urn : nbn: de: gbv: 715-oops-7657 (dissertation, University of Oldenburg).
  8. ↑ A. Steinbüchel, FB Oppermann-Sanio: Microbiological internship. Trials and theory. Springer Verlag, Berlin 2003, ISBN 3-540-44383-5 , p. 59.
  9. ↑ Dipicolinic acid data sheet from Sigma-Aldrich , accessed on March 31, 2010 ( PDF ).Template: Sigma-Aldrich / name not given
  10. ↑ Sabrina Dehn: Enantiomerically pure β-diketonates [beta-diketonates] for luminescent helicate-like complexes . Aachen 2007, DNB  98372718X , urn : nbn: de: hbz: 82-opus-18115 (dissertation, RWTH Aachen).
  11. ↑ Patent EP0742206 : Percarboxylic acid solutions with improved stability in presence steel. Published on September 29, 1999 , inventors: Georg Thiele, Peter Täubl. ‌

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