81810-66-4

Basic information

• Product Name: Quinocetone
• Synonyms: 2-Cinnamoyl-3-methylquinoxaline 1,4-dioxide;QUINOCETONE;1-(3-Methyl-1,4-dioxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one;1-(3-Methyl-2-quinoxalinyl)-3-phenyl-2-propen-1-one N,N'-dioxide
• CAS NO: 81810-66-4
• Molecular Formula: C₁₈H₁₄N₂O₃
• Molecular Weight: 306.32
• EINECS: 1312995-182-4
• Mol File: 81810-66-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 183-188 °C
• Boiling Point: 576.9±60.0 °C(Predicted)
• Appearance: /
• Density: 1.22
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 1.62±0.30(Predicted)
• CAS DataBase Reference: Quinocetone(CAS DataBase Reference)
• NIST Chemistry Reference: Quinocetone(81810-66-4)
• EPA Substance Registry System: Quinocetone(81810-66-4)

Safety Data

• Hazardous Substances Data: 81810-66-4(Hazardous Substances Data)

Usage

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.

Upstream product

• 88-74-4 2-nitro-aniline 
• 480-96-6 benzofurazan oxide 
• 100-52-7 benzaldehyde 
• 123-54-6 acetylacetone 
• 13297-17-1 3-methyl-2-acetylquinoxaline-1,4-dioxide 

Downstream Products

• 80109-63-3 1-(3-methyl-2-quinoxalinyl)-3-phenyl-2-propen-1-one 
• 111232-63-4 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one 

Relevant articles and documents

Synthesis method of quinocetone

The invention discloses a new synthesis method of quinocetone. Quinocetone is synthesized from mequindox and benzaldehyde as raw materials by reaction in an amino acids-alkali composite catalytic system. The product yield is 90% or higher and purity can reach 99%. Besides, the catalytic system promotes rapid reaction of mequindox and benzaldehyde at a lower temperature in the water phase to prepare the high-quality product, reaction conditions are mild, yield is excellent, and the production process is simple and convenient, safe and reliable; after the product is removed, the catalytic systemcan be recycled 3 times without changing the catalytic effect, and accordingly, the production cost can be reduced.

Improved synthesis of quinocetone

The invention discloses a preparation method of improved quinocetone and the preparation method can be used for solving the problems in the prior art that the reaction time is long, low in product yield, poor in product quality and the lime. The preparation method is characterized by comprising the following steps: dissolving benzaldehyde, a catalyst, a water adsorbent and mequindox in methanol; in a heating state, stirring to react for 1-6 hours; after reaction, cooling and separating out a product; and filtering, washing and drying to obtain the product which meets the quality standard of quinocetone related to Veterinary Drug National Standard (Volume One) of Department of Agriculture. The yield of quinocetone prepared by the method reaches over 93% which is far higher than that recorded in available literatures, and the purity reaches over 98.5% which is higher than the content requirement of Department of Agriculture. Moreover, the reaction time is short, and the labor efficiency and the utilization ratio of equipment are improved.

Quinocetone preparation method

The present invention discloses an improved quinocetone preparation method comprising the following steps: in a reaction vessel equipped with a stirrer and a condenser tube, a solvent, mequindox, benzaldehyde, a water-absorbing agent and an ionic liquid catalyst are added successively, the temperature is raised from room temperature to 60-65 DEG C for reaction while stirring for 3.5 hours, and the mixture is cooled to 30 DEG C, filtered, washed and dried to obtain quinocetone with a purity of 98.5% or more and a yield of 94.5% or more, wherein the molar feeding ratio of mequindox to benzaldehyde to catalyst is 1.0: 1.11-1.21: 0.14. During the preparation of the quinocetone, a product does not need to be refined, and the pure product can be obtained by direct filtration, washing and drying. The improved quinocetone preparation method has the characteristics of easily obtained raw materials, short reaction time, simple operation, high product purity, high yield and low production cost.