Hypericin Synthesis via Protohypericin Salt Photoreaction
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Solution Overview
Problem
The existing methods for isolating hypericin from Hypericum plants are inefficient due to low yield and purity, and synthetic processes also face challenges in achieving high yield and purity, particularly in separating hypericin from pseudo-hypericin and requiring lengthy solvent extraction and chromatographic separations.
Innovation Solution
A process involving the conversion of emodin to emodin anthrone, followed by dimerization to protohypericin, then conversion to a salt, and subsequent visible light irradiation to produce hypericin, combined with a purification method using solvents and recrystallization to achieve high purity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If hypericin is isolated from Hypericum plants using traditional extraction and chromatographic methods, then pure hypericin can be obtained, but the process is lengthy and requires large volumes of solvents and cumbersome chromatographic separations
Solution Approach 1:
The patent employs parameter changes by converting emodin to emodin anthrone through controlled chemical transformation, then dimerizing to form protohypericin, and finally using visible light irradiation to convert tohypericin. This systematic transformation of chemical parameters achieves high purity (≥95%) while dramatically reducing process time compared to traditional plant extraction methods
Solution Approach 2:
The patent utilizes phase transitions in the purification process, specifically employing recrystallization from polar solvents and precipitation using non-polar solvents to obtain purehypericin. The compound transitions between dissolved and crystalline phases, enabling efficient separation and purification without lengthy chromatographic procedures
2Quantity of substance
If hypericin is isolated from Hypericum plants, then hypericin can be obtained, but the yield is very low not more than 0.3% based on dry plant material
Solution Approach 1:
The patent applies preliminary action by starting with emodin as the starting material and performing preparative transformations (conversion to emodin anthrone, then dimerization to protohypericin) before the final phot conversion tohypericin. This preliminary preparation of the molecular structure enables high-yield production (≥95%) compared to the 0.3% yield from plant material
Solution Approach 2:
The patent replaces mechanical extraction and separation systems with a chemical synthesis pathway. Instead of mechanically extractinghypericin from plants through solvent extraction and chromatography, the invention uses chemical transformations and photoreactions to synthesizehypericin from emodin, achieving dramatically improved material efficiency and yield
3Productivity
If emodin is converted to emodin anthrone and dimerized to form protohypericin followed by visible light irradiation, thenhypericin can be synthesized, but the existing process produces low yield and purity of the final product
Solution Approach 1:
The patent uses intermediaries in the form of emodin anthrone and protohypericin as intermediate compounds in the synthesis pathway. The conversion proceeds through emodin → emodin anthrone → protohypericin →hypericin, with each intermediate serving as a necessary precursor. The use of protohypericin salt as an intermediate before final phot conversion specifically enables high yield and purity of the final product
Solution Approach 2:
The patent employs periodic action through the multi-step sequential process: first converting emodin to emodin anthrone, then dimerizing to protohypericin, converting to protohypericin salt, and finally using visible light irradiation to producehypericin. This periodic transformation through distinct stages, each optimized for its specific conversion, achieves both high yield and high purity (≥95%)
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 process results in hypericin with a purity of at least 95% and a yield improvement, allowing for the production of hypericin at greater than 98% purity through efficient photoreaction and purification steps.
Implementation Method 1
Visible light irradiation, preferably at about 400-700 nm, is then used to convert the protohypericin salt tohypericin
Implementation Method 2
dissolving the crudehypericin in a solvent, preferably a polar solvent such as methanol, by heating, preferably to about 50-55° C.
Implementation Method 3
The filtered solid product is then dried, preferably in vacuo at about 50-60° C., to obtainhypericin at greater than 98% pure
Implementation Method 4
The filtrate is also cooled to precipitatehypericin
Data Source
AI summary
The present invention provides a method for making hypericin comprising the steps of converting a protohypericin to a protohypericin salt, and irradiating the protohypericin salt with visible light to form hypericin. The present invention also provides an apparatus comprising a transparent column having a top end and a bottom end, an inlet attached to the column at the top end to flow reactants into the column, a container attached to the column at the bottom end; and a visible light source positioned to cast light on to the column. The present invention further provides a method for making hypericin using said apparatus.