Method for extraction of high purity solanocupsin and synthesis of isodecyl dienol and isoprenol

An extraction method, solanesol technology, applied in chemical instruments and methods, preparation of organic compounds, separation/purification of hydroxyl compounds, etc., can solve the problem of only 90%, low purity, and failure to meet the requirements of pharmaceuticals, etc. problem, to achieve the effect of low cost and high yield

Inactive Publication Date: 2008-09-10
玉溪健坤生物药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many methods for extracting solanesol from tobacco, such as the method for extracting solanesol from nicotine-extracted tobacco with the patent No. 94107849.3. , using Cs---G2 aliphatic alkane as a solvent to extract, concentrate the extract, add soda ash solution for saponification, remove water and solvent, treat with a mixed solvent of ketone and alcohol, cool, and separate out solanesol, solanesol extracted by this method Alcohol, the purity can only reach 90%, the purity is low, and it cannot meet the requirements of pharmaceuticals

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0006] Example 1 1.1 Extraction of high-purity solanesol (96%)

[0007] 50g of crude solanesol (content 17%) is saponified with alkali in 1000ml mixed organic solvent (methanol, petroleum ether 95:5), the reaction time is 4 hours, and the reaction temperature is 60°C. After the reaction is completed, add 1500ml mixed solvent Continue stirring with the decolorizing agent for 1 hour, cool the precipitate, and centrifuge to separate. The filtrate crystallizes at -25°C-0°C. The obtained crystals are separated and recrystallized with the above mixed solvent to obtain solanesol with a content of 50-75%. The latter is dissolved in a non-organic organic solvent, and the impurity is removed by tubular clarification and filtration. The filtrate is concentrated and purified by column chromatography. The eluate can be concentrated and crystallized to obtain solanesol with a content of ≥90%, which is purified on the column for the second time. Finally, 48g of high-purity solanesol with a c...

Embodiment 2

[0012] Example 2 2.1. Extraction of high-purity solanesol (96%).

[0013] 50g crude solanesol (content 17%), in 1000ml mixed organic solvent (ethanol, sherwood oil 95: 5), add alkali saponification, reaction time 6h, reaction temperature 70 ℃, after reaction finishes, add 1200ml mixed solvent and Continue to stir the decolorant for 1 hour, cool down and precipitate, and centrifuge to separate. The filtrate is crystallized at 0-15° C., and the obtained crystals are separated, and then recrystallized with the above-mentioned mixed solvent to obtain solanesol with a content of 50-75%. The latter is dissolved in a non-polar organic solvent, and vacuum filtration is used to remove impurities. After the filtrate is concentrated, it is purified and separated by column chromatography. 43g of high-purity solanesol with a content of 96% can be obtained, and the yield is 48%.

[0014] 2.2 Preparation of isodecprenol

[0015] Take 100g of 95% solanesol, dissolve it in 160ml of dry dieth...

Embodiment 3

[0018] Example 3 3.1. Extraction of high-purity solanesol (96%)

[0019] 50g crude solanesol (content 17%), in 1000ml mixed organic solvent (methanol, sherwood oil 98: 2), add alkali saponification, reaction time 2h, reaction temperature 80 ℃, after reaction finishes, add 1500ml mixed solvent and Continue to stir the decolorizer for 1 hour, cool down and precipitate, and centrifuge to separate. The filtrate is crystallized at 0-10° C., and the obtained crystals are separated, and then recrystallized with the above-mentioned mixed solvent to obtain solanesol with a content of 50-75%. The latter is dissolved in a non-polar organic solvent, clarified and filtered. Centrifugal separation and filtration to remove impurities, and the filtrate is concentrated and then purified by column chromatography. The eluate should be concentrated and then crystallized to reach 90% solanesol. After the second column purification, 96% high-purity can be obtained. Solanesol 46g, the yield is 54%....

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PUM

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Abstract

The invention provides a process for preparing high-purity solanesol, which is used as the raw material for halogenating, and reacting with acetoacetic ester to obtain solanesol propanone, then is subject to reaction with the chlorovinyl magnesium to obtain isoprene alcohol, wherein the overall yield rate of solanesol is 48%.

Description

Technical field: [0001] The invention relates to a method for purifying solanesol from an extract containing solanesol. Background technique: [0002] The English name of solanesol is Solanesol, which is the main intermediate for the synthesis of coenzyme Q10 and vitamin K2 and an important intermediate for the manufacture of certain anti-allergic drugs, anti-ulcer drugs, hypolipidemic drugs, and anti-cancer drugs. It mainly exists in animal organs. In organs and plant leaves, the content is highest in tobacco. There are many methods for extracting solanesol from tobacco, such as the method for extracting solanesol from nicotine-extracted tobacco with the patent No. 94107849.3. , using Cs---G2 aliphatic alkane as a solvent to extract, concentrate the extract, add soda ash solution for saponification, remove water and solvent, treat with a mixed solvent of ketone and alcohol, cool, and separate out solanesol, solanesol extracted by this method Alcohol, the purity can only r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/76C07C29/32C07C33/02
Inventor 马震
Owner 玉溪健坤生物药业有限公司
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