MedKoo Cat#: 558630 | Name: Citrazinic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Citrazinic acid inhibits 3-dehydroquinate dehydratase from Mycobacterium tuberculosis.

Chemical Structure

Citrazinic acid
Citrazinic acid
CAS#99-11-6

Theoretical Analysis

MedKoo Cat#: 558630

Name: Citrazinic acid

CAS#: 99-11-6

Chemical Formula: C6H5NO4

Exact Mass: 155.0200

Molecular Weight: 155.11

Elemental Analysis: C, 46.46; H, 3.25; N, 9.03; O, 41.26

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
25g USD 450.00 2 Weeks
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Related CAS #
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Synonym
Citrazinic acid; Kyselina citrazinova; 2,6-Dihydroxyisonicotinate; 2,6-Dihydroxyisonicotinic acid;
IUPAC/Chemical Name
2,6-Dihydroxyisonicotinic acid
InChi Key
CSGQJHQYWJLPKY-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H5NO4/c8-4-1-3(6(10)11)2-5(9)7-4/h1-2H,(H,10,11)(H2,7,8,9)
SMILES Code
O=C(O)C1=CC(O)=NC(O)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 155.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Sarkar S, Chowdhury J, Dutta S, Pal T. A pH dependent Raman and surface enhanced Raman spectroscopic studies of citrazinic acid aided by theoretical calculations. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Dec 5;169:108-15. doi: 10.1016/j.saa.2016.06.023. Epub 2016 Jun 16. PubMed PMID: 27344521. 2: Hossan AS, Abu-Melha HM, Al-Omar MA, Amr Ael-G. Synthesis and antimicrobial activity of some new pyrimidinone and oxazinone derivatives fused with thiophene rings using 2-chloro-6-ethoxy-4-acetylpyridine as starting material. Molecules. 2012 Nov 19;17(11):13642-55. doi: 10.3390/molecules171113642. PubMed PMID: 23165308. 3: Masoud MS, Ibrahim AA, Khalil EA, El-Marghany A. Spectral properties of some metal complexes derived from uracil-thiouracil and citrazinic acid compounds. Spectrochim Acta A Mol Biomol Spectrosc. 2007 Jul;67(3-4):662-8. Epub 2006 Aug 25. PubMed PMID: 17029947. 4: Dias MV, Snee WC, Bromfield KM, Payne RJ, Palaninathan SK, Ciulli A, Howard NI, Abell C, Sacchettini JC, Blundell TL. Structural investigation of inhibitor designs targeting 3-dehydroquinate dehydratase from the shikimate pathway of Mycobacterium tuberculosis. Biochem J. 2011 Jun 15;436(3):729-39. doi: 10.1042/BJ20110002. PubMed PMID: 21410435. 5: Adamczyk M, Akireddy SR, Reddy RE. An efficient enantioselective synthesis of (S)-(-)-acromelobic acid. Org Lett. 2000 Nov 2;2(22):3421-3. PubMed PMID: 11081998. 6: Howard NI, Dias MV, Peyrot F, Chen L, Schmidt MF, Blundell TL, Abell C. Design and structural analysis of aromatic inhibitors of type II dehydroquinase from Mycobacterium tuberculosis. ChemMedChem. 2015 Jan;10(1):116-33. doi: 10.1002/cmdc.201402298. Epub 2014 Sep 18. PubMed PMID: 25234229. 7: Masoud MS, Khalil EA, Hindawy AM, Ali AE, Mohamed EF. Spectroscopic studies on some azo compounds and their cobalt, copper and nickel complexes. Spectrochim Acta A Mol Biomol Spectrosc. 2004 Oct;60(12):2807-17. PubMed PMID: 15350916. 8: Amb CM, Rasmussen SC. 6,6'-Dibromo-4,4'-di(hexoxymethyl)-2,2'- bipyridine: a new solubilizing building block for macromolecular and supramolecular applications. J Org Chem. 2006 Jun 9;71(12):4696-9. PubMed PMID: 16749811. 9: Iqbal N, Kumar M, Sharma P, Yadav SP, Kaur P, Sharma S, Singh TP. Binding studies and structure determination of the recombinantly produced type-II 3-dehydroquinate dehydratase from Acinetobacter baumannii. Int J Biol Macromol. 2017 Jan;94(Pt A):459-465. doi: 10.1016/j.ijbiomac.2016.10.049. Epub 2016 Oct 18. PubMed PMID: 27769928. 10: McCormick SJ, Tunnicliff G. Inhibitors of synaptosomal gamma-hydroxybutyrate transport. Pharmacology. 1998 Sep;57(3):124-31. PubMed PMID: 9691232. 11: Sharma A, Gadly T, Neogy S, Ghosh SK, Kumbhakar M. Molecular Origin and Self-Assembly of Fluorescent Carbon Nanodots in Polar Solvents. J Phys Chem Lett. 2017 Mar 2;8(5):1044-1052. doi: 10.1021/acs.jpclett.7b00170. Epub 2017 Feb 17. PubMed PMID: 28198626. 12: Fukushima M, Iizuka K, Jin C, Zhang C, Hong M, Eshima K. Development of new promising antimetabolite, DFP-11207 with self-controlled toxicity in rodents. Drug Des Devel Ther. 2017 Jun 7;11:1693-1705. doi: 10.2147/DDDT.S128420. eCollection 2017. PubMed PMID: 28652707; PubMed Central PMCID: PMC5472421. 13: Ehrat F, Bhattacharyya S, Schneider J, Löf A, Wyrwich R, Rogach AL, Stolarczyk JK, Urban AS, Feldmann J. Tracking the Source of Carbon Dot Photoluminescence: Aromatic Domains versus Molecular Fluorophores. Nano Lett. 2017 Dec 13;17(12):7710-7716. doi: 10.1021/acs.nanolett.7b03863. Epub 2017 Dec 1. PubMed PMID: 29188711.