Polyglycerol Ester Synthesis for Solvent-Free 3-Hydroxybutyric Acid
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Solution Overview
Problem
Existing technologies lack efficient and physiologically compatible precursors or metabolites of 3-hydroxybutyric acid, which are necessary for therapeutic applications due to issues such as nausea, bitterness, kidney damage, and short plasma half-life, limiting their effectiveness in treating metabolic disorders and neurodegenerative diseases.
Innovation Solution
The development of polyol esters, particularly polyglycerol esters of optionally acylated 3-hydroxybutyric acid, produced through a novel process that avoids undesirable side reactions and enables large-scale, solvent-free synthesis, ensuring physiological compatibility and effective conversion to 3-hydroxybutyric acid in the body.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If free 3-hydroxybutyric acid or its salts are administered, then therapeutic effects for metabolic disorders and neurodegenerative diseases are achieved, but nausea, bitterness, kidney damage, and short plasma half-life occur
Solution Approach 1:
The patent uses polyol esters (particularly polyglycerol esters) of optionally acylated 3-hydroxybutyric acid as intermediary compounds. These esters serve as prodrugs that are converted in vivo to release free 3-hydroxybutyric acid, thereby providing therapeutic effects while avoiding the direct administration of free acid and its associated side effects such as nausea, bitterness, and kidney damage
Solution Approach 2:
The patent modifies the chemical parameters of 3-hydroxybutyric acid by converting it into ester forms with polyols. This parameter change (from free acid to ester) fundamentally alters the compound's properties: it becomes less irritating to the gastrointestinal tract, less bitter, less toxic to kidneys, and has prolonged plasma half-life, while maintaining the ability to release the active free acid form in the body
2Ease of manufacture
If conventional synthesis methods are used for polyol esters, then production is possible, but undesirable side reactions occur and solvent removal is required
Solution Approach 1:
The patent removes the problematic solvent step from conventional synthesis methods. The novel process enables synthesis of polyol esters without requiring solvent removal, thereby eliminating solvent contamination and simplifying the manufacturing process while maintaining production capability
Solution Approach 2:
The patent converts the potential harm of side reactions into benefit by using specific reaction conditions and catalysts that minimize unwanted byproducts. The process transforms a potentially harmful synthesis route into a clean, efficient method that produces desired polyol esters with minimal side reactions
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 polyglycerol esters provide a physiologically compatible and effective alternative to free 3-hydroxybutyric acid, allowing for prolonged therapeutic benefits without toxicity, bitterness, or kidney strain, and are suitable for industrial production.
Implementation Method 1
reacting a carboxylic anhydride, in particular 3-hydroxybutyric anhydride, optionally acylated 3-hydroxybutyric anhydride, with a polyol, in particular polyglycerol
Data Source
AI summary
The invention relates to a method for producing polyol esters, particularly polyglycerol esters, of optionally acylated 3-hydroxy butyric acid, to products obtained in this way, and to the use of same.