81468-73-7

Basic information

• Product Name: Ethanone, 1-(5-butyl-2,4-dihydroxyphenyl)-
• Synonyms: 2,4-dihydroxy-5-n-butylacetophenone;1-(5-butyl-2,4-dihydroxy-phenyl)-ethanone;1-(5-butyl-2,4-dihydroxyphenyl)ethanone;5-butyl-2,4-dihydroxyacetophenone;2,4-dihydroxy-5-butylacetophenone;1-(5-Butyl-2,4-dihydroxy-phenyl)-aethanon
• CAS NO: 81468-73-7
• Molecular Formula: C12H16O3
• Molecular Weight: 208.25400
• Mol File: 81468-73-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 60 - 70 °C
• Boiling Point: 370.6±27.0 °C(Predicted)
• Density: 1.133±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Ethanone, 1-(5-butyl-2,4-dihydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(5-butyl-2,4-dihydroxyphenyl)-(81468-73-7)
• EPA Substance Registry System: Ethanone, 1-(5-butyl-2,4-dihydroxyphenyl)-(81468-73-7)

Safety Data

• Hazardous Substances Data: 81468-73-7(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of acetonitrile on 4-n-butylresorcinol (Hoesch reaction) (80%) [.

Upstream product

• 18979-61-8 4-butylresorcinol 
• 75-05-8 acetonitrile 
• 75-36-5 acetyl chloride 
• 373-61-5 boron trifluoride diacetate 
• 2161-86-6 2,4-diacetylphloroglucinol 
• 108-22-5 Isopropenyl acetate 
• 2466-76-4 N-Acetylimidazole 
• 108-46-3 recorcinol 
• 151-10-0 1,3-Dimethoxybenzene 
• 117705-67-6 1-(2,4-dimethoxyphenyl)-1-butanol 
• 6703-00-0 1-(2,4-dimethoxyphenyl)butan-1-one 
• 54459-33-5 2,4-dimethoxy-n-butylbenzene 
• 4390-92-5 1-(2,4-dihydroxyphenyl)butan-1-one 
• 117690-82-1 5-butyl-2,4-dimethoxyacetophenone 

Downstream Products

• 81468-79-3 2-ethoxy-4-methoxy-5-butylacetophenone oxime 
• 81468-76-0 2-ethoxy-4-methoxy-5-butylacetophenone 
• 343956-23-0 4-methoxy-2-hydroxy-5-butylacetophenone 
• 117690-69-4 4-(4-cyanobutoxy)-5-butyl-2-hydroxyacetophenone 
• 90547-05-0 2,4-diethoxy-5-n-butylacetophenone 

Relevant articles and documents

Thioesters as Acyl Donors in Biocatalytic Friedel-Crafts-type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens

Functionalization of aromatic compounds by acylation has considerable significance in synthetic organic chemistry. As an alternative to chemical Friedel-Crafts acylation, the C-acyltransferase from Pseudomonas protegens has been found to catalyze C?C bond formation with non-natural resorcinol substrates. Extending the scope of acyl donors, it is now shown that the enzyme is also able to catalyze C?S bond cleavage prior to C?C bond formation, thus aliphatic and aromatic thioesters can be used as acyl donors. It is worth to mention that this reaction can be performed in aqueous buffer. Identifying ethyl thioacetate as the most suitable acetyl donor, the products were obtained with up to >99 % conversion and up to 88 % isolated yield without using additional base additives; this represents a significant advancement to prior protocols.

Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists

Compound 1 (IC50 = 35.2 ± 7.2 μM), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 ± 0.1 μM. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity.

ANTI-INFLAMMATORY AGENTS

This invention provides benzene derivatives, pharmaceutical formulations of those derivatives, and a method of using the derivatives for the treatment of inflammation in mammals.