Terpene Ester Synthesis for Novel Fragrance Profiles

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Solution Overview

Problem

The fragrance and flavor industry lacks new natural scents and tastes, as existing terpene-based compounds are either difficult to obtain economically or lack the desired natural character.

Innovation Solution

Development of terpene esters with unique structures, specifically through the esterification of 2-methyl-2-butenenitrile or 2-methyl-3-butenenitrile with prenyl chloride, followed by saponification and subsequent esterification with haloalkanes or alcohols, creating compounds like ethyl, n-propyl, and methyl 2,5-dimethyl-2-vinyl-4-hexenoate, which exhibit distinct floral, fruity, and balsamic scents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If existing terpene-based compounds are used, then the natural character is maintained, but the variety and novelty of fragrance profiles are limited

Engineering Contradiction:

Improvevariety of fragrance profilesVSAvoidnovelty of compounds

Core Design Contradiction:

Adaptability or versatilityVSQuantity of substance

Solution Approach 1:

The patent segments the traditional terpene structure by introducing a new functional group (cyano group at position 2) and modifying the substitution pattern (prenyl groups at positions 5 and 6), thereby creating distinct molecular segments that combine to form novel fragrance compounds with unique profiles

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The patent creates composite molecular structures by combining the cyano-terpene core with various ester groups (acetate, propionate, butyrate, etc.), resulting in hybrid compounds that exhibit both the natural character of terpenes and the diverse olfactory properties of ester functional groups

Inventive Principle:

Principle #40Composite materials

2Adaptability or versatility

If new terpene structures are developed, then the fragrance variety is improved, but the production complexity increases

Engineering Contradiction:

Improvenovelty of fragrance profilesVSAvoidsynthesis process complexity

Core Design Contradiction:

Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent employs preliminary action by first establishing the core cyano-terpene structure through alkylation of 2-methyl-2-butenonitrile, then systematically deriving various ester compounds from this pre-formed core, thereby simplifying the overall synthesis pathway

Inventive Principle:

Principle #10Preliminary action

Solution Approach 2:

The patent uses the cyano-terpene core structure as an intermediary compound that serves as a common precursor for generating multiple different ester derivatives, thereby reducing the need for separate synthesis routes for each fragrance variant

Inventive Principle:

Principle #24Intermediary (Mediator)

3Reliability

If natural terpene esters are obtained from plant sources, then the natural character is preserved, but the extraction cost and difficulty increase

Engineering Contradiction:

Improvenatural character of fragranceVSAvoidextraction difficulty

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The patent replaces the mechanical extraction process (distillation, solvent extraction from plant materials) with a chemical synthesis approach that uses readily available starting materials and straightforward organic reactions to produce the same natural-character compounds

Inventive Principle:

Principle #28Mechanics substitution (Replace mechanical system)

Solution Approach 2:

The patent changes the production parameters from natural extraction (requiring large quantities of plant material, complex separation processes) to controlled chemical synthesis (using stoichiometric reactions, purified reagents, and standard organic synthesis techniques)

Inventive Principle:

Principle #35Parameter changes

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

These terpene esters provide new, natural fragrance and flavor profiles that can be used in perfumery and cosmetic products, enhancing creativity and meeting industry demands for unique scents, with specific examples like ethyl 2,5-dimethyl-2-vinyl-4-hexenoate offering a strong, natural appeal with fruity and floral hints, and methyl 2,5-dimethyl-2-vinyl-4-hexenoate providing a bitter, spicy note reminiscent of citrus and coriander.

Implementation Method 1

phase-transfer-catalyzed alkylation of the industrially available 2-methyl-2-butenonitrile or 2-methyl-3-butenonitrile with prenym chloride

Methodology Applied

Scientific EffectPhase-transfer catalysis:

Implementation Method 2

alkylation of the industrially available 2-methyl-2-butenonitrile or 2-methyl-3-butenonitrile with prenym chloride

Methodology Applied

Scientific EffectAlkylation:

Implementation Method 3

Saponification of the 2,5-dimethyl-2-vinyl-4-hexenonitrile obtained in step (i) to give 2,5-dimethyl-2-vinyl-4-hexenoic acid

Methodology Applied

Scientific EffectSaponification: Hydrolysis

Implementation Method 4

Esterification of the compound obtained in step (ii) with the corresponding haloalkane or alcohol

Methodology Applied

Scientific EffectEsterification:

Data Source

PatentEP3786149A1Terpene esters, their preparation and use as flavourings and perfumes

Publication Date: 2021.03.03 MILTITZ AROMATICS GMBH

AI summary

The invention relates to a compound of formula (I), wherein R is a linear or branched C2 to C8 alkyl group or C2 to C8 alkenyl group or a C3 to C8 cycloalkyl group, as well as a process for producing such a compound and the use of a compound of formula (I) as a fragrance or flavoring agent, wherein R is a linear or branched C1 to C8 alkyl group or C2 to C8 alkenyl group or a C3 to C8 cycloalkyl group.