Dipicolinic acid

  • CAT Number: M009332
  • CAS Number: 499-83-2
  • Molecular Formula: C7H5NO4
  • Molecular Weight: 167.12
  • Purity: ≥95%
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Dipicolinic acid (Cat No.:M009332) is an organic compound with the chemical formula C7H5NO4. It is known for its unique role as a major component of bacterial endospores, which are highly resistant, dormant forms of bacteria. Dipicolinic acid plays a critical role in the heat resistance and protective mechanisms of endospores, contributing to their ability to survive extreme conditions like high temperatures and desiccation. Due to its association with endospores, it is often used as a biomarker in microbiological and environmental studies to detect and identify bacterial spores. Additionally, dipicolinic acid has applications in analytical chemistry and as a metal chelator.

Catalog Number M009332
CAS Number 499-83-2
Molecular Formula

C7H5NO4

Purity 95%
Storage -20°C
IUPAC Name pyridine-2,6-dicarboxylic acid
InChI InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12)
InChIKey WJJMNDUMQPNECX-UHFFFAOYSA-N
SMILES C1=CC(=NC(=C1)C(=O)O)C(=O)O
Reference

1: Martin AD, Britton J, Easun TL, Blake AJ, Lewis W, Schröder M. Hirshfeld
Surface Investigation of Structure-Directing Interactions within Dipicolinic Acid
Derivatives. Cryst Growth Des. 2015 Apr 1;15(4):1697-1706. Epub 2015 Mar 20.
PubMed PMID: 25866487; PubMed Central PMCID: PMC4386464.
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2: Han Y, Zhou S, Wang L, Guan X. Nanopore back titration analysis of dipicolinic
acid. Electrophoresis. 2015 Feb;36(3):467-70. doi: 10.1002/elps.201400255. Epub
2014 Oct 3. PubMed PMID: 25074707; PubMed Central PMCID: PMC4511083.

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3: Datta S, Chatterjee S, Mitra S, Basu S. A reliable phenotypic assay for
detection of ESBLs and AmpCs in MBL-producing gram-negative bacteria with the use
of aminophenylboronic acid, dipicolinic acid and cloxacillin. J Microbiol
Methods. 2015 Aug;115:100-3. doi: 10.1016/j.mimet.2015.05.028. Epub 2015 Jun 3.
PubMed PMID: 26048656.
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4: van Dijk K, Voets GM, Scharringa J, Voskuil S, Fluit AC, Rottier WC,
Leverstein-Van Hall MA, Cohen Stuart JW. A disc diffusion assay for detection of
class A, B and OXA-48 carbapenemases in Enterobacteriaceae using phenyl boronic
acid, dipicolinic acid and temocillin. Clin Microbiol Infect. 2014
Apr;20(4):345-9. doi: 10.1111/1469-0691.12322. Epub 2013 Aug 9. PubMed PMID:
23927659.

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5: Francis MB, Allen CA, Sorg JA. Spore Cortex Hydrolysis Precedes Dipicolinic
Acid Release during Clostridium difficile Spore Germination. J Bacteriol. 2015
Jul;197(14):2276-83. doi: 10.1128/JB.02575-14. Epub 2015 Apr 27. PubMed PMID:
25917906; PubMed Central PMCID: PMC4524186.
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6: Takahashi F, Sumitomo N, Hagihara H, Ozaki K. Increased dipicolinic acid
production with an enhanced spoVF operon in Bacillus subtilis and medium
optimization. Biosci Biotechnol Biochem. 2015;79(3):505-11. doi:
10.1080/09168451.2014.978261. Epub 2014 Nov 17. PubMed PMID: 25402593.

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7: Wang J, de Kool RH, Velders AH. Lanthanide-Dipicolinic Acid Coordination
Driven Micelles with Enhanced Stability and Tunable Function. Langmuir. 2015 Nov
10;31(44):12251-9. doi: 10.1021/acs.langmuir.5b03226. Epub 2015 Oct 28. PubMed
PMID: 26479961.

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