Citrazinic acid

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Citrazinic acid
Names
Preferred IUPAC name
6-Hydroxy-2-oxo-1,2-dihydropyridine-4-carboxylic acid
Other names
2,6-Dihydroxyisonicotinic acid; 2,6-Dihydroxypyridine-4-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.483 Edit this at Wikidata
EC Number
  • 202-731-2
MeSH acid Citrazinic acid
RTECS number
  • NS1400000
UNII
  • InChI=1S/C6H5NO4/c8-4-1-3(6(10)11)2-5(9)7-4/h1-2H,(H,10,11)(H2,7,8,9) ☒N
    Key: CSGQJHQYWJLPKY-UHFFFAOYSA-N ☒N
  • O=C(O)C=1\C=C(\O)NC(=O)C=1
Properties
C6H5NO4
Molar mass 155.109 g·mol−1
Appearance yellow powder
Melting point >300 °C (decomp.)
Slightly soluble
Solubility Slightly soluble in methanol, DMSO, acidic solutions
Very soluble in alkaline solutions
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P280, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Lethal dose or concentration (LD, LC):
> 3200 mg/kg ( Rat )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Citrazinic acid (CZA) is a heterocyclic compound consisting of a dihydropyridine ring derived with a carboxylate group. The yellow solid exists as multiple tautomers, and it frequently forms dimers.[1]

Citrazinic acid is commonly formed in citric acid based carbon nanodots (CND). It is responsible for the blue light found in citric acid CNDs. The wavelengths of light emitted by citrazinic in CNDs can be shifted by changing the pH of the solution.[2]

Preparation

Citrazinic acid can be prepared creating a solution of citric acid and toluenesulfonic acid, which forms a 1,3-diester. That solution, when added to a heated ammonia solution results in citrazinic acid.[3]

References

  1. ^ Stagi L, Mura S, Malfatti L, Carbonaro CM, Ricci PC, Porcu S, et al. (May 2020). "Anomalous Optical Properties of Citrazinic Acid under Extreme pH Conditions". ACS Omega. 5 (19): 10958–10964. doi:10.1021/acsomega.0c00775. PMC 7241015. PMID 32455216.
  2. ^ Mocci F, Olla C, Cappai A, Corpino R, Ricci PC, Chiriu D, et al. (February 2021). "Formation of Citrazinic Acid Ions and Their Contribution to Optical and Magnetic Features of Carbon Nanodots: A Combined Experimental and Computational Approach". Materials. 14 (4): 770. Bibcode:2021Mate...14..770M. doi:10.3390/ma14040770. PMC 7914458. PMID 33562081.
  3. ^ Baizer MM, Dub M, Gister S, Steinberg NG (July 1956). "Synthesis of isoniazid from citric acid". Journal of the American Pharmaceutical Association. 45 (7): 478–480. doi:10.1002/jps.3030450714. PMID 13345683.
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