Fatty Alcohol Hydroxybutyrate Ester Synthesis via Enzyme Catalysis

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Solution Overview

Problem

Existing methods for producing 3-hydroxybutyric acid and its salts are inefficient, physiologically incompatible, and lead to significant side reactions, making them unsuitable for therapeutic applications due to toxicity and poor physiological compatibility.

Innovation Solution

A method for producing fatty alcohol esters of 3-hydroxybutyric acid and acylated derivatives through a single-step synthesis using commercially available starting materials, avoiding solvents and minimizing by-products, which are physiologically compatible and can be broken down to release 3-hydroxybutyric acid or its salts.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If existing methods for producing 3-hydroxybutyric acid and its salts are used, then production can be achieved, but the methods are inefficient and lead to significant side reactions with toxicity

Engineering Contradiction:
Improveproduction efficiencyVSAvoidtoxicity and side reactions
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent uses an enzyme (catalyst) as an intermediary to mediate the reaction between the starting material and 3-hydroxybutyric acid. This enzymatic catalysis provides a selective and efficient pathway that avoids the toxic side reactions associated with conventional chemical methods, while maintaining high production efficiency

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the reaction parameters by using mild enzymatic conditions instead of harsh chemical conditions. This includes controlling temperature, pH, and using specific enzymes to achieve high productivity while eliminating toxicity and side reactions associated with traditional methods

Inventive Principle:
Principle #35Parameter changes

2Productivity

If existing production methods are used, then 3-hydroxybutyric acid can be produced, but the products are physiologically incompatible and unsuitable for therapeutic applications

Engineering Contradiction:
Improveproduction capabilityVSAvoidphysiological compatibility
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The enzyme acts as a mediator that ensures the production of physiologically compatible 3-hydroxybutyric acid through biologically appropriate pathways, making the product suitable for therapeutic applications while maintaining production capability

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent replaces conventional chemical synthesis mechanisms with biological enzymatic mechanisms. This substitution ensures that the production process and resulting product are physiologically compatible, while still achieving efficient production through catalytic action

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

3Quantity of substance

If larger quantities of 3-hydroxybutyric acid are administered, then therapeutic effectiveness may improve, but toxicity increases with existing production methods

Engineering Contradiction:
Improveadministerable quantityVSAvoidtoxicity
Core Design Contradiction:
Quantity of substanceVSObject-generated harmful factors

Solution Approach 1:

The enzymatic catalyst provides a clean reaction pathway that eliminates toxic by-products, enabling the administration of larger quantities of 3-hydroxybutyric acid for therapeutic purposes without the toxicity constraints that limit dosing in conventional methods

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent converts the potential harm of toxicity into a benefit by using enzymatic selectivity to avoid toxic side reactions entirely. This allows larger therapeutic doses to be administered safely, as the production method inherently prevents toxin formation rather than merely mitigating it

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 method enables the production of physiologically compatible fatty alcohol esters of 3-hydroxybutyric acid, allowing for larger quantities to be administered without toxicity, providing a stable and effective alternative for therapeutic use.

Implementation Method 1

The reaction of the ethyl 3-hydroxybutyrate with the fatty alcohol yields the fatty alcohol ester of the 3-hydroxybutyric acid and ethanol. In a preferred embodiment, the reaction is carried out in the presence of a catalyst, especially an enzyme and/or a metal-containing and/or metal-based, acidic or basic catalyst

Methodology Applied
Scientific EffectEnzyme catalysis: Enzyme

Implementation Method 2

The reaction of the ethyl 3-hydroxybutyrate with the fatty alcohol yields the fatty alcohol ester of the 3-hydroxybutyric acid and ethanol

Methodology Applied
Scientific EffectTransesterification: Chemical Bonding

Data Source

PatentUS12365645B2Method for producing fatty alcohol esters of hydroxycarboxylic acids
Publication Date: 2025.07.22 KETOLIPIX THERAPEUTICS GMBH
  • US12365645B2 patent drawing
  • US12365645B2 patent drawing
  • US12365645B2 patent drawing

AI summary

The invention relates to a method for producing fatty alcohol esters of 3-hydroxybutyric acid and their acylated derivatives, as well as the products thus obtained and their use.