Lycopene Intermediate Synthesis via C-14 Enol Ether
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Solution Overview
Problem
Existing methods for synthesizing lycopene, such as the Wittig-Horner reaction and other processes, face challenges including the difficulty in obtaining key intermediates and the need for expensive, toxic, or hazardous reagents, making them unsuitable for industrial production.
Innovation Solution
A new synthetic route involving the preparation of 1-methoxyl-2, 6, 10-trimethyl-1, 3, 5, 9-undec-tetraene (C-14 enol ether) through a rearrangement dissociation reaction and Wittig-Horner condensation, followed by hydrolysis to obtain pure 2-pos double bond C-14 aldehyde, simplifying the process and using more readily available and cost-effective materials.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Device complexity
If the Wittig-Horner reaction method is used to synthesize lycopene, then the synthesis route is simplified and fewer reaction steps are required, but the key intermediate (6) is difficult to obtain and the reduction technology is difficult to grasp
Solution Approach 1:
The patent segments the synthesis route by introducing a new key intermediate (1,3,6,10-tetra-double bond pentadec-carbon phosphonate) with a different structural arrangement. This segmentation allows the synthesis to proceed through more accessible reaction steps while maintaining the simplified Wittig-Horner condensation approach with decadialdehyde.
Solution Approach 2:
The patent changes the positional parameters of the double bonds in the key intermediate from the conventional structure to a 1,3,6,10-tetra-double bond configuration. This parameter change enables better obtainability of the intermediate through standard organic synthesis methods while preserving the efficiency of the condensation reaction with decadialdehyde.
2Productivity
If triphenylphosphine is used as raw material in the Wittig reaction, then the synthesis can proceed, but expensive and toxic reagents are required
Solution Approach 1:
The patent replaces the expensive and toxic triphenylphosphine with more economical and environmentally friendly phosphorus reagents. The new key intermediate uses readily available phosphonate compounds that are less toxic and more cost-effective, while still enabling the Wittig-Horner condensation reaction to proceed efficiently.
Solution Approach 2:
The patent introduces a novel phosphonate intermediate (1,3,6,10-tetra-double bond pentadec-carbon phosphonate) that serves as a mediator between the starting materials and the final lycopene product. This intermediary compound enables the reaction to proceed without requiring triphenylphosphine, thus eliminating the associated toxicity and cost issues.
3Ease of manufacture
If the method using C-14 aldehyde with 3-pos double bond is employed, then the intermediate can be obtained, but expensive methyl iodide, polluting dimethyl sulphide and dangerous strong base are needed
Solution Approach 1:
The patent converts the harmful reagents (methyl iodide, dimethyl sulphide, strong base) into a safer and more environmentally friendly synthesis pathway. By using the 1,3,6,10-tetra-double bond phosphonate intermediate, the reaction conditions can be optimized to avoid or minimize the use of hazardous substances, thus converting a potentially harmful process into a benign one.
Solution Approach 2:
The patent changes the reaction parameters by using a phosphonate intermediate with a specific 1,3,6,10-tetra-double bond configuration. This structural parameter change allows the synthesis to proceed under milder and safer conditions, eliminating the need for expensive methyl iodide, polluting dimethyl sulphide, and dangerous strong bases.
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 approach simplifies the synthesis of lycopene intermediates, reduces the need for expensive reagents, and enhances the suitability for industrial production by achieving high purity and yield with a more straightforward process.
Implementation Method 1
C-4 phosphate ester, shown as Formula (6), is subjected to rearrangement dissociation reaction under the protection of inert gas and at the presence of organic solvent and base
Implementation Method 2
citral, shown as Formula (5), is then added to the substance derived from the step 1) to perform Wittig-Horner condensation reaction
Implementation Method 3
followed by hydrolysis to obtain pure 2-pos double bond C-14 aldehyde
Data Source
AI summary
The invention discloses an intermediate 1-methoxyl-2, 6, 10-trimethyl-1, 3, 5, 9-undec-tetraene, and a preparation method and uses thereof. In the synthesis method for the current lycopene intermediate 2-pos double bond C-14 aldehyde (2, 6, 10-trimethyl-2, 5, 9-undecatriene-1-aldehyde), expensive methyl iodide, polluting dimethyl sulphide and dangerous strong base are needed, so that the method is hardly applied to industrial production. The invention provides a new compound 1-methoxyl-2, 6, 10-trimethyl-1, 3, 5, 9-undec-tetraene, and pure 2-pos double bond C-14 aldehyde can be prepared by hydrolyzing and refining the compound. The synthetic route is simplified and the great suitability for industrial production is achieved.