Cyclopropane Fragrance Compounds for Diffusive Lasting Citrus Notes

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Solution Overview

Problem

There is a demand for flavor and fragrance compounds with high diffusibility, unique odor quality, long-lasting properties, and high safety, particularly for floral or citrus-like odors, which are currently insufficiently met by existing substances.

Innovation Solution

A compound with a cyclopropane ring, specifically an allyl alcohol derivative subjected to cyclopropane formation, is developed to impart a strong floral or citrus-like odor, suitable for use in various products such as cosmetics, pharmaceuticals, and food items.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional flavor and fragrance substances are used, then basic odor functionality is provided, but the odor quality is insufficient and lacks uniqueness, high diffusibility, and long-lasting characteristics

Engineering Contradiction:
Improveodor quality and performanceVSAvoidsuitability for diverse modern products
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent modifies the molecular structure of conventional fragrance compounds by introducing a cyclopropane ring structure and specific substituent groups (R1-R5, m, n parameters) to create novel compounds with enhanced odor properties including higher diffusibility, unique floral or citrus-like odor quality, and improved stability for modern product applications

Inventive Principle:
Principle #35Parameter changes

2Reliability

If new flavor and fragrance compounds are developed to meet high standards, then odor quality and diffusibility are improved, but the number of available compounds remains insufficient

Engineering Contradiction:
Improveodor performance characteristicsVSAvoidnumber of available compounds
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent systematically varies multiple parameters (R1-R5 substituents, m and n values, cyclopropane ring configuration) of the core molecular structure to generate a family of novel compounds, thereby increasing the quantity of available high-performance fragrance substances through structured molecular diversification

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

By modifying structural parameters (different alkyl groups, hydroxyl positions, cyclopropane substitutions) of the base molecule, the patent creates multiple distinct compounds with enhanced odor properties, expanding the available repertoire of high-performance fragrance materials

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS9296675B2Compound having cyclopropane ring, and flavor and/or fragrance composition containing same
Publication Date: 2016.03.29 TAKASAGO INTERNATIONAL CORP
  • US9296675B2 patent drawing
  • US9296675B2 patent drawing
  • US9296675B2 patent drawing

AI summary

Provided are a compound of formula (1), having a cyclopropane ring, which can impart a floral or citrus-like aroma and a flavor composition containing at least one compound of formula (1):wherein, R1, R2, R3 and R5 independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, wherein at least two groups among R1, R2, R3 and R5 independently represent an alkyl group; R4 represents a group selected from a formyl group, a hydroxymethyl group, a 1-hydroxy-1-ethyl group, a 1-hydroxy-1-propyl group, a 1-hydroxy-1-butyl group and a 2-hydroxy-1-propyl group; m represents 0 to 2; n represents 0 or 1; and a wavy line stands for a cis-configuration, a trans-configuration or a mixture of a cis-configuration and a trans-configuration with respect to position-2 on a cyclopropane ring.