Quinocetone Chemical Properties

Melting point:

183-188 °C

Boiling point:

576.9±60.0 °C(Predicted)

Density 

1.22

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)

pka

1.62±0.30(Predicted)

form 

Solid

color 

Yellow

InChI

InChI=1S/C18H14N2O3/c1-13-18(17(21)12-11-14-7-3-2-4-8-14)20(23)16-10-6-5-9-15(16)19(13)22/h2-12H,1H3

InChIKey

IOKWXGMNRWVQHX-UHFFFAOYSA-N

SMILES

C(C1=C(C)[N+]([O-])=C2C(=[N+]1[O-])C=CC=C2)(=O)C=CC1=CC=CC=C1

Quinocetone Usage And Synthesis

Description

Quinocetone is a novel veterinary chemicals that is also bacteriocide and potential anti-tumor agent.

Uses

Quinocetone can be used as analyte in analytical study for multi-residue determination of 210 drugs in pork by ultra-high-performance liquid chromatography-tandem mass spectrometry. Bacteriocide and potential anti-tumor agent.

Definition

Quinocetone is a quinoxaline-N,N-dioxide antimicrobial agent used in veterinary medicine as a feed additive for livestock, birds and fish. It is an antidiarrheal growth promotion drug developed in Lanzhou, China. Quinocetone has also been seen to induce a decline in aldosterone production from the swine adrenal glands in vivo and in vitro, and thus cause hypovolemia, hyponatremia and hyperkalemia. The compound is under investigation for potential benefits against aldosterone dysmetabolism disease via the reduction of aldosterone production in adrenal and/or the cardiovascular tissues. This may provide a new option in the therapy for aldosterone dysmetabolism disease, especially in the cardiovascular system.

Biological Activity

Quinocetone is a potent synthetic antimicrobial agent that is used for improving the feed efficiency and controlling dysentery in food-producing animals.

Synthesis

In a 250 mL three-neck flask, 64 mL of methanol and 5.05 g (0.0455 mol) of anhydrous CaCl? were added and stirred until completely dissolved. Subsequently, 3.70 g (0.0344 mol) of hydroxyethylamine formate solution was added slowly and dropwise. Next, 20.25 g (0.1908 mol) of benzaldehyde was added, stirred and the temperature of the reaction system was raised to 50 °C. Then, 37.50 g (0.1718 mol) of 2-acetyl-3-methylquinoxaline 1,4-dioxide was added and slowly heated to 60-65 °C and kept at this temperature for 3 hours of reaction. The progress of the reaction was monitored by TLC and the heating was stopped after confirming the completion of the reaction. The reaction mixture was cooled to 25°C and subjected to diafiltration. The resulting solid was washed 3 times with methanol, evacuated and dried under vacuum to give 49.98 g of bright yellow powdery solid product 2-cinnamoyl-3-methylquinoxaline 1,4-dioxide with a melting point of 189-191 °C, purity of 98.7% and yield of 95.0%.

References

[1] Patent: CN105566234, 2016, A. Location in patent: Paragraph 0016; 0017; 0018
[2] Journal of the Serbian Chemical Society, 2018, vol. 83, # 3, p. 265 - 270
[3] Patent: CN104672155, 2017, B. Location in patent: Paragraph 0018; 0032-0041
[4] Heterocycles, 1987, vol. 26, # 1, p. 55 - 58
[5] European Journal of Medicinal Chemistry, 2010, vol. 45, # 10, p. 4682 - 4686

Quinocetone(81810-66-4)Related Product Information

• Basic Violet 1
• Acetonitrile
• 3-（trifluoromethyl) Cinnamaldehyde
• alpha-Methylcinnamic acid
• Quinoxaline
• Methylparaben
• Methyl acetate
• Methyl acrylate
• Sulfurous Acid
• Paraquat dichloride
• Zirconium dioxide
• PHENYL VALERATE
• Thiourea dioxide
• Kresoxim-methyl
• Chlorine dioxide
• 3-(Trifluoromethyl)cinnamic acid
• Quartz
• Methanol