105638-31-1

Basic information

• Product Name: 3-(3,4-Dimethoxyphenyl)-pentane-2-one
• Synonyms: 17P-[(N,N-dimethylcarbamoyl)thio]carbonyl-6a,9adifluoro-11~-hydroxy-l6a-methyl-l7a-propionyloxy-3-oxoandrosta-l,4-di;3-(3,4-Dimethoxyphenyl)pentane-2-one;Fluticasone intermediate FN-1(2)
• CAS NO: 105638-31-1
• Molecular Formula: C₂₇H₃₅F₂NO₆S
• Molecular Weight: 222.28
• Mol File: 105638-31-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 624.2±65.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• PKA: 12.56±0.70(Predicted)
• CAS DataBase Reference: 3-(3,4-Dimethoxyphenyl)-pentane-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3,4-Dimethoxyphenyl)-pentane-2-one(105638-31-1)
• EPA Substance Registry System: 3-(3,4-Dimethoxyphenyl)-pentane-2-one(105638-31-1)

Safety Data

• Hazardous Substances Data: 105638-31-1(Hazardous Substances Data)

Usage

General Description

3-(3,4-Dimethoxyphenyl)-pentane-2-one is a chemical compound with the molecular formula C13H18O3. It is also known as 3,4-dimethoxyphenylpentane-2-one and is a yellow to orange liquid with a sweet, floral odor. 3-(3,4-Dimethoxyphenyl)-pentane-2-one is used as a flavor and fragrance ingredient in the food and beverage industry, as well as in perfumes and cosmetics. It is primarily sourced from natural plant extracts and has been found to have antimicrobial and antioxidant properties. Additionally, it is used as a building block in the synthesis of other organic compounds and pharmaceuticals. However, the exact uses and applications of 3-(3,4-Dimethoxyphenyl)-pentane-2-one can vary depending on the specific industry and its regulations.

Upstream product

• 28416-82-2 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid 
• 65429-42-7 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 2135-17-3 flumetasone 

Downstream Products

• 80474-14-2 flixotide 
• 59860-80-9 methyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carboxylate 
• 80474-45-9 17-propionate carbothioic acid 
• 80474-67-5 S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxo-androsta-1,4-diene-17β-carbothioate 
• 80486-69-7 S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate 

Relevant articles and documents

Synthesis and structure-activity relationships in a series of antiinflammatory corticosteroid analogues, halomethyl androstane-17β- carbothioates and -17β-carboselenoates

The preparation and topical antiinflammatory potencies of a series of halomethyl 17α-(acyloxy)-11β-hydroxy-3-oxoandrosta-1,4-diene-17β- carbothioates, carrying combinations of 6α-fluoro, 9α-fluoro, 16-methyl, and 16-methylene substituents, are described. Key synthetic stages were the preparation of carbothioic acids and their reaction with dihalomethanes. The carbothioic acids were formed from 17β-carboxylic acids by initial reaction with dimethylthiocarbamoyl chloride followed by aminolysis of the resulting rearranged mixed anhydride with diethylamine, or by carboxyl activation with 1,1'-carbonyldiimidazole (CDI) or 2-fluoro-N-methylpyridinium tosylate (FMPT) and reaction with hydrogen sulfide, the choice of reagent being governed by the 17α-substituent. Carboxyl activation with FMPT and reaction with sodium hydrogen selenide led to the halomethyl 16-methyleneandrostane-17β- carboselenoate analogues. Anti-inflammatory potencies were measured in humans using the vasoconstriction assay and in rats and mice by a modification the Tonelli croton oil ear assay. Best activities were shown by fluoromethyl and chloromethyl carbothioates with a 17α-propionyloxy group. S-Fluoromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta- 1,4-diene-17β-carbothioate (fluticasone propionate, FP) was selected for clinical study as it showed high topical antiinflammatory activity but caused little hypothalamic-pituitary-adrenal suppression after topical or oral administration to rodents.

METHODS OF PREPARING INTERMEDIATE OF FLUTICASONE PROPIONATE

A method of preparing a thioic acid intermediate of fluticasone propionate includes: treating a 17β-[(N,N-dimethyl carbamoyl)thio]carbonyl compound in a solution including an alcohol and an alkali metal hydroxide, an alkaline-earth metal hydroxide, or a mixture thereof to cleave an amide from the 17β-[(N,N-dimethyl carbamoyl)thio]carbonyl compound; treating the solution to separate an aqueous portion; and adding an acid to the aqueous portion to obtain the thioic acid intermediate of fluticasone propionate. A method of preparing fluticasone propionate includes preparing the thioic acid intermediate of fluticasone propionate, and alkylating the thioic acid intermediate of fluticasone propionate to prepare the fluticasone propionate.

METHOD FOR PREPARATION OF FLUTICASONE PROPIONATE

Taught is a method for preparing S-fluoromethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxoandrosta-1,4-diene-17β-carbothioate (fluticasone propionate). The present method is simple, convenient, and mild, yields highly pure product, and is suitable for use commercially on a large scale.