Carboxylic Acid Ester Fragrance with Bulky Ring Structure
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
There is a need for novel fragrance components that can provide diverse scents to cater to changing consumer preferences, and compounds with bulky ring structures are required for various applications including medicines, agricultural chemicals, and functional materials.
Innovation Solution
The development of carboxylic acid ester compounds represented by the general formula (1) and their production method, which involves reacting 4-isopropenyl-1-methyl-1-cyclohexene with carbon monoxide in the presence of hydrogen fluoride, followed by esterification, to create compounds with unique aromas and structural properties suitable for fragrances and other materials.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If conventional esters are used for fragrances, then familiar scents (rose-like, jasmine-like, fruity) are provided, but novel and unprecedented fragrance components are lacking
Solution Approach 1:
The patent modifies the molecular structure parameters of ester compounds by introducing bulky ring structures (norbornene, adamantane) and specific substituent patterns (methyl groups at positions 1 and 3, carboxymethyl groups at positions 3 and 5). This structural parameter change creates novel fragrance compounds with both unprecedented scents and improved aroma sustainability, resolving the contradiction between fragrance diversity and aroma reliability.
2Adaptability or versatility
If compounds with bulky ring structures are synthesized for various applications, then novel compounds for medicines, agricultural chemicals, and functional materials are obtained, but the development of specific novel compounds with desired properties becomes time-consuming
Solution Approach 1:
The patent performs preliminary structural design by pre-establishing the core bulky ring structure (2,4-dimethylbicyclo[2.2.2]octane) with predetermined substituent positions. This preliminary action creates a versatile scaffold that can be efficiently modified to produce multiple novel compounds for different applications (medicines, agricultural chemicals, fragrances, functional materials), thereby improving compound development efficiency while maintaining broad application range.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The resulting carboxylic acid ester compounds offer intense, fruity, and spicy floral aromas with excellent sustainability, enabling the diversification of fragrances in various products and serving as effective raw materials for multiple industrial applications due to their structural properties.
Implementation Method 1
allowing, in the presence of hydrogen fluoride, 4-isopropenyl-1-methyl-1-cyclohexene represented by the formula (2) to react with carbon monoxide and a monovalent alcohol having 1 to 4 carbon atoms
Data Source
AI summary
The present invention provides a novel carboxylic acid ester compound useful as a fragrance component or a material for a compound fragrance and a method for producing the same, and provides a fragrance composition including the carboxylic acid ester compound. The present invention also provides an acyl fluorides of a 2,4-dimethyl-bicyclo[2.2.2]octane compound and the esters thereof, useful as the raw materials (inclusive of the intermediates of organic synthesis), for example, for the medicines, agricultural chemicals, fragrances, functional resins, optical functional materials and electronic functional materials. The carboxylic acid ester compound of the present invention is a compound represented by the general formula (1). (In the formula, one of R1 and R2 is a methyl group and the other of R1 and R2 is - COOR, and R is an alkyl group having 1 to 4 carbon atoms.)