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 quinoxaline-N,N-dioxide antimicrobial agent used in veterinary medicine as a feed additive for livestock, birds, and fish. It is a novel veterinary chemical that serves as a bactericide and potential anti-tumor agent. Developed in Lanzhou, China, as an antidiarrheal growth promotion drug, Quinocetone has been observed to induce a decline in aldosterone production from swine adrenal glands, leading to hypovolemia, hyponatremia, and hyperkalemia. Quinocetone is under investigation for its potential benefits against aldosterone dysmetabolism disease by reducing aldosterone production in adrenal and/or cardiovascular tissues, offering a new therapeutic option for aldosterone dysmetabolism disease, particularly in the cardiovascular system.

Uses

Used in Analytical Studies:
Quinocetone is used as an analyte in analytical studies for multi-residue determination of 210 drugs in pork by ultra-high-performance liquid chromatography-tandem mass spectrometry.
Used in Veterinary Medicine:
Quinocetone is used as a feed additive for livestock, birds, and fish, serving as a bactericide and potential anti-tumor agent.
Used in Growth Promotion and Diarrhea Treatment:
As an antidiarrheal growth promotion drug, Quinocetone is used to promote growth and treat diarrhea in animals.
Used in Aldosterone Dysmetabolism Disease Therapy:
Quinocetone is being investigated for its potential benefits against aldosterone dysmetabolism disease by reducing aldosterone production in adrenal and/or cardiovascular tissues, providing 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

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

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.

Preparation method of quinocetone

The invention discloses a preparation method of quinocetone. The preparation method comprises that benzofurazan, acetylacetone and benzaldehyde as raw materials in the presence of magnetic magnesium-aluminum hydrotalcite solid alkali and alkaline quaternary ammonium salt as catalysts in anhydrous ethanol as a solvent undergo a reaction at a temperature of 10-100 DEG C for 1-10h, and then the reaction product liquid is treated to form quinocetone. Through use of the magnetic magnesium-aluminum hydrotalcite solid alkali catalyst, the preparation method has simple processes, can be operated easily, realizes easy product separation, has small environmental pollution, is suitable for industrial production with a certain scale and is a green and clean synthesis route.