Lycopene Synthesis via C15-Wittig Salt Purification
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Solution Overview
Problem
Conventional synthesis processes for producing synthetic lycopene result in low all-E content, with E/Z isomer ratios of 3.4:1 to 3.8:1, failing to meet the specifications of biological lycopene extracted from natural sources like Blakeslea trispora, and existing thermal isomerization processes only increase all-E content to 73.4% to 87.8%.
Innovation Solution
Purification of C15-Wittig salts using a series of steps in aprotic solvents such as ethyl acetate, chloroform, and acetone, followed by a double Wittig reaction with C10-dialdehyde, allows for the production of lycopene with up to 95% all-E content or 97% 5Z content by controlling E/Z isomer ratios through solvent combinations and temperature adjustments.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional synthesis process is used to produce synthetic lycopene, then lycopene can be manufactured, but the all-E content is low (E/Z ratio of 3.4:1 to 3.8:1)
Solution Approach 1:
The patent applies preliminary action by purifying all-trans-pseudoionone before synthesis to increase its content to 95-98%, and by pre-forming C15-Wittig salts with high all-E content (90-95%) through controlled reaction conditions. This preliminary purification and preparation eliminates the need for complex post-synthesis separation, directly achieving high all-E lycopene content while simplifying the overall manufacturing process.
2Manufacturing precision
If all-trans-pseudoionone is separated from cis/trans mixture by fractional distillation, then higher all-E containing lycopene can be obtained, but the synthesis process becomes more complex
Solution Approach 1:
The patent changes the purification parameter from fractional distillation to silica gel column chromatography, utilizing differential adsorption properties. By optimizing the eluent system (petroleum ether/ethyl acetate ratios) and column parameters, all-trans-pseudoionone is separated with 95-98% purity. This parameter change maintains high all-E content while simplifying the process compared to multiple distillation steps.
3Productivity
If C15 phosphonium salt is synthesized to produce lycopene, then lycopene can be manufactured, but the E isomer/Z isomer ratio decreases (only 65.2% to 71.1% all-E content)
Solution Approach 1:
The patent optimizes multiple reaction parameters: using purified all-trans-pseudoionone (95-98% purity) as starting material, controlling reaction temperature (0-25°C), selecting appropriate bases (n-BuLi, LDA), and optimizing solvent systems. These parameter changes ensure the C15-Wittig salt maintains 90-95% all-E content throughout synthesis, directly producing high all-E lycopene without requiring post-synthesis isomerization or extensive purification.
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 achieves E/Z isomer ratios greater than 15:1 for all-E lycopene and less than 1:30 for 5Z lycopene, meeting or exceeding the specifications for biological lycopene, thereby producing synthetic lycopene with high all-E or 5Z content.
Implementation Method 1
Purification of C15-Wittig salts using a series of steps in aprotic solvents such as ethyl acetate, chloroform, and acetone
Implementation Method 2
The method achieves E/Z isomer ratios greater than 15:1 for all-E lycopene and less than 1:30 for 5Z lycopene, meeting or exceeding the specifications for biological lycopene
Data Source
AI summary
The present invention relates to methods for preparation of lycopenes, especially to lycopenes with high all-E contents or high 6Z contents from C15-Wittig salts mixtures (with high all-E-contents and high 6Z-contents, respectively). C15-Wittig salts mixtures are purified and 6Z-C15-Wittig salts are extracted from the mixtures. The extracted 6Z-C 15-Wittig salts are used in the synthesis of lycopenes with high 6Z contents and the residues are used in the synthesis of lycopenes with high all-E contents.