Antimicrobial Propanone for Stable Deodorant Formulations

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Solution Overview

Problem

Current cosmetic and pharmaceutical products lack effective, toxicologically safe, and stable antimicrobial agents that can inhibit or kill microorganisms causing body odor, such as Staphylococcus epidermidis, Corynebacterium xerosis, and Brevibacterium epidermidis, without causing skin irritation or discoloration.

Innovation Solution

The development of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone, a compound with excellent antimicrobial properties, high stability across various temperatures and pH ranges, and a weak vanilla-like odor, suitable for use in cosmetic and pharmaceutical formulations, which is produced through an aldol condensation reaction followed by hydrogenation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional antimicrobial agents are used to inhibit microorganisms causing body odor, then antimicrobial activity is achieved, but toxicological safety and skin compatibility deteriorate

Engineering Contradiction:
Improveantimicrobial activityVSAvoidtoxicological safety and skin compatibility
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of known antimicrobial compounds (such as dihydrochalcones and flavonoids) through specific substitution patterns and functional groups to achieve optimal balance between antimicrobial activity and skin compatibility. The compound 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone represents a specific parameter optimization that maintains efficacy while improving safety profile.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If strong antimicrobial agents are used to kill odor-forming bacteria, then antimicrobial efficacy is improved, but skin irritation and discoloration increase

Engineering Contradiction:
Improveantimicrobial efficacyVSAvoidskin irritation and discoloration
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent applies local quality by introducing specific functional groups (hydroxy, methoxy) at particular positions on the molecular structure to create localized regions of desired chemical properties. This allows the compound to exhibit strong antimicrobial activity at specific interaction sites while maintaining overall gentleness and stability toward skin tissues.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs composite material principles by combining multiple functional groups (ketone, hydroxy, methoxy) within a single molecular framework to achieve a compound that integrates antimicrobial efficacy with skin compatibility and color stability in cosmetic formulations.

Inventive Principle:
Principle #40Composite materials

3Reliability

If existing antimicrobial substances are applied to inhibit sweat bacteria, then deodorant effect is achieved, but stability in cosmetic formulations deteriorates

Engineering Contradiction:
Improvedeodorant effectVSAvoidformulation stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by optimizing the chemical structure to achieve pH stability across a wide range (pH 3-10) and thermal stability up to 80°C, ensuring the compound remains effective and stable in various cosmetic formulation conditions while maintaining its deodorant function.

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

This compound effectively inhibits the growth of odor-forming microorganisms, providing a stable and safe alternative for deodorant applications, maintaining colorlessness and skin compatibility, and is suitable for a wide range of cosmetic and pharmaceutical products.

Implementation Method 1

the novel compound according to the invention of the formula 1, namely 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone, has excellent antimicrobial properties and in particular is active against the stated microorganisms

Methodology Applied
Scientific EffectAntimicrobial action:

Implementation Method 2

The production method preferred according to the invention may be illustrated by the following scheme: (a) reaction (aldol condensation) of p-hydroxyacetophenone with vanillin

Methodology Applied
Scientific EffectAldol condensation: Chemical Bonding

Implementation Method 3

(b) reduction, preferably hydrogenation, of the reaction product obtained in step (a)

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentEP2170796B13-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone and use thereof as an antimicrobial active ingredient
Publication Date: 2012.09.12 SYMRISE GMBH & CO KG
  • EP2170796B1 patent drawing
  • EP2170796B1 patent drawing
  • EP2170796B1 patent drawing

AI summary

Antimicrobially active 3-(4-hydroxy-3-methoxyphenyl)-1 -(4-hydroxyphenyl)-1 - propanone of the following formula 1 is described, as is a method for producing this compound and the use thereof as an antimicrobial active ingredient. Formula (I).