What is stigmasterol
Stigmesterol is a natural plant sterol. Natural phytosterols are similar in structure to animal sterols such as cholesterol. They are an active ingredient in plants and are found in various vegetable oils. They are widely used in medicine, food, cosmetics and other industries. Stigmesterol is an organic compound with the molecular formula C29H48O. Belongs to plant sterols. The pure product is colorless crystal. Soluble in general organic solvents, hardly soluble in water. It is isolated from soybeans and lentils.
What is the use of stigmasterol
Stigmesterol is mainly used as a raw material for the synthesis of steroid hormones and can also be used as a raw material for the production of vitamin D3. It is used in biochemical research to produce progesterone, and is also a raw material for producing progesterone in medicine.
Plant extraction method of stigmasterol
At present, the main methods for extracting stigmasterol from mixed phytosterols are: solvent method and solvent crystallization method. Directly utilize the solubility difference of each component in the mixed phytosterols, select appropriate organic solvents for multi-step extraction, recrystallization and separation; use organic acids and alcohol hydroxyl groups contained in the mixed phytosterols to undergo a esterification reaction to generate the corresponding phytosterols Derivatives can increase the difference in physical properties, and then use recrystallization and other methods to separate them; use the sterol ring and the double bond on the branch to undergo a halogen addition reaction to increase the difference in physical parameters of the generated derivatives, and then select the appropriate Organic solvents are used for extraction and recrystallization separation.
Solvent method, using soybean mixed plant alcohol as raw material, by adjusting the material-liquid ratio and crystallization temperature, it is proved that after 2 to 3 stages of step-by-step crystallization, the purity of soybean alcohol can be obtained >60%. Through 4-5 levels of crystallization, the purity can reach more than 85%.
2. Solvent crystallization method A comparison of the processes for separating mixed phytosterols from the solvent crystallization method found that the presence of a small amount of water can not only greatly increase the sterol yield, but also improve the stigmasterol selectivity in certain ranges, helping to obtain high-purity beans. Sterol and sitosterol products.
2.1 Multi-stage fractional crystallization method. The reaction steps of this method are as follows: in the first step, add solvent anhydrous ethanol, n-propanol or n-butanol to phytosterol, raise the temperature to dissolve, then slowly cool down the temperature to crystallize , filter, and repeat the above concentration steps 0~ Once, then perform centrifugal separation and vacuum drying; in the second step, add a separation solvent to the phytosterol concentrate obtained in the first step, raise the temperature to dissolve, then slowly cool down to crystallize, filter, and repeat the above separation steps 2~ 3 times. This invention greatly improves the purity and yield of stigmasterol through two separate steps of concentration and separation and refining of raw materials, and does not pollute the environment.
2.2 Polar solvent crystallization method: First use non-polar solvents to enrich stigmasterol to 90%, and then use polar solvents to crystallize to obtain high-purity stigmasterol. The process is to dissolve the raw materials in toluene to prepare a 25% solution, cool to 25°C, hold at a constant temperature for 1 hour, crystallize, and repeat 6 times to obtain stigmasterol with a purity of 92%. When the purity of stigmasterol is greater than 90%, it can no longer be enriched by crystallization. At this time, the obtained stigmasterol is dissolved in acetone under anhydrous conditions at a ratio of 1:20, slowly cooled, and crystallized to reduce the purity. Increased to 98%.
2.3 Organic solvent crystallization method Wang Yaqiong et al. used mixed plant sterols as raw materials to study the separation and crystallization characteristics of stigmasterol in three solvents: toluene, toluene methanol and toluene acetone. It showed that using toluene (90%) and acetone (10%) Mixed solvents, after 5 times of crystallization, the stigmasterol content is >70%, and the total stigmasterol yield is >50%. Gao Yuying et al. used n-butanol as the solvent to enrich stigmasterol from mixed soybean phytosterols. The solid-liquid ratio was 1:4, placed in a constant temperature water bath at 20°C to 30°C, crystallized for 1 to 2 hours, and then filtered or centrifuged at a constant temperature. 4 ~ Level 5 crystallization yields stigmasterol with a content of more than 85%.
Preparation method of stigmasterol
The effective separation of mixed phytosterols is an important research topic in the process of realizing large-scale production of single-component high-purity phytosterols. The separation and purification of mixed phytosterols can provide a relatively cheap method for the production of steroid drugs. Common extraction and separation methods include the following methods:
Using ethyl acetate as the extractant and soybean oil as the raw material, ultrasound was used to assist in the extraction of stigmasterol in soybean oil. On the basis of single factor experiment, the extraction process was optimized through orthogonal experiment L9 (34). The results It shows that the optimal process conditions for ultrasound-assisted extraction of stigmasterol from soybean oil are: ultrasonic temperature of 50°C, ultrasonic time of 40 minutes, and liquid-to-solid ratio of 19 mL/g. Under these optimal conditions, the extraction rate of stigmasterol was the highest, reaching 34.15%.
Due to the extreme similarity in structure, it is a difficult and tedious task to separate and remove β-sitosterol, rapeseedosterol and campesterol from plant sterols to obtain monomer stigmasterol with higher purity. In 1906, Windaus and Hauth proposed using the chemical reaction of bromoacetyl compounds to enrich stigmasterol. Stigmosterol is refluxed in acetic anhydride to form stigmasterol acetate. Then brominate dichloropropylene with excess bromine in to generate 5,6,22,23-tetrabromide stigmasterol acetate and 5,6-dibromide β-sitosterol acetate. These two substances are Slightly soluble or relatively soluble. Stigmisterol acetyl tetrabromide can be crystallized in ethanol, treated with zinc powder, and then subjected to saponification reaction, that is, debromination and deacetylation, to regenerate stigmasterol. Finally, pure stigmasterol can be obtained by crystallization in acetone to achieve the purpose of separation.
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