Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Cleaning production technique of 16-dehydro pregnenetrolone and its same kind compound

A technology of pregnenolone and production technology, which is applied in the field of degrading steroidal sapogenin into 16-dehydropregnenolone and similar products, can solve problems such as failure to remove it, achieve improved utilization and eliminate environmental pollution problems, the effect of improving product yield

Inactive Publication Date: 2004-02-18
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
View PDF3 Cites 26 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although this degradation method is continuously improved (Micovic I.V.Synthesis, 1990,591), it still fails to change its shortcomings.
That is, the chromic anhydride oxidation reaction in the degradation process cannot be eliminated, that is to say: the environmental pollution problem in the degradation process of steroidal saponin has not yet been resolved

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Oxidative degradation of timogenin into 3β-hydroxy-5β-pregna-16(17)-en-20-one and 3S-methyl-δ-valerolactone:

[0028] 10 grams of timogenin were dissolved in acetic acid and acetic anhydride, reacted in an autoclave for 1 hour, and added 3.3 mg of Na 2 WO 1 2H 2 O (0.01mmol), 5ml hydrogen peroxide (30%H 2 O), stirred and reacted in an oil bath at 80° C. for 2 hours. The acetic acid was distilled off under reduced pressure to obtain a crude product of oxidative degradation, which was dissolved in 50 ml of ethanol, refluxed for 2 hours with 5% lithium hydroxide, concentrated, added with water, and filtered to obtain 6.3 g of 3β-hydroxy-5β-pregna-16(17)- en-20-one. Yield 84%. m.p.186-8℃, hydrogen nuclear magnetic resonance spectrum (300MHz, CDCl 3 )δ: 6.61(dd, J=1.3Hz, 1H, 16-H), 3.5(m, 1H, 3-H), 2.26(s, 3H, CH 3 CO-, 21-H), 0.84 (s, 3H, 18-H), 0.88 (s, 3H, 19-H) ppm. Mass Spectrum (m / z, %): 316 (M + ), 301 (M + -CH 3 ), 28...

Embodiment 2

[0029] Example 2 Oxidative degradation of timogenin into 3β-hydroxy-5β-pregna-16(17)-en-20-one and 3S-methyl-δ-valerolactone:

[0030] 100 grams of timogenin were dissolved in acetic acid and acetic anhydride, reacted in an autoclave for 1 hour, and the solvent was removed under reduced pressure, and the obtained pseudogenin was dissolved in 500 milliliters of butanol, and 23 milligrams of WO 3 (0.1mmol), 10 grams of isophthalic acid, 50 milliliters of hydrogen peroxide (30% H 2 O), stirring and reacting in an oil bath at 80° C. for 2 hours. Add potassium hydroxide and continue to reflux for 2 hours, concentrate, add water, and filter to obtain 66 g of 3β-hydroxy-5β-pregna-16(17)-en-20-one. Yield 88%. The aqueous layer was acidified and extracted to obtain 22 g of 3S-methyl-δ-valerolactone with a yield of 84%. The spectral data are the same as in Example 1.

Embodiment 3

[0031]Example 3 Oxidative degradation of timogenin into 3β-hydroxy-5β-pregna-16(17)-en-20-one and 3S-methyl-δ-valerolactone:

[0032] 100 grams of timogenin were dissolved in acetic acid and acetic anhydride, reacted in an autoclave for 1 hour, and the solvent was removed under reduced pressure, and the obtained pseudogenin was dissolved in 500 milliliters of butanol, and 23 mg of WO was added. 3 (0.1mmol), 1 gram of p-toluenesulfonic acid, 50 milliliters of hydrogen peroxide (30% H 2 O), stirred and reacted in an oil bath at 80° C. for 2 hours. Add potassium hydroxide and continue to reflux for 2 hours, concentrate, add water, and filter to obtain 60 g of 3β-hydroxy-5β-pregna-16(17)-en-20-one. Yield 80%. The aqueous layer was acidified and extracted to obtain 22 g of 3S-methyl-δ-valerolactone with a yield of 84%. The spectral data are the same as in Example 1.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
IR spectroscopyaaaaaaaaaa
Login to View More

Abstract

A clean process for preparing 16-dehydropregnenolone and its analog includes cracking steroid sapogenin to obtain pseudo-steroid sapogenin, reacting on H2O2 in organic solvent under existance of metallic catalyst and acid, and reacting on alkali to obtain 16-dehydropregneno / one or its analog and 3R (or S)- methyl-4-hydroxy-valerate. Its advantages are high output rate and no environmental pollution.

Description

technical field [0001] The invention relates to a method for degrading steroidal saponin into 16-dehydropregnenolone and its similar products. Background technique [0002] 16-Dehydropregnenolone (3β-hydroxy-pregnenol-5(6), 16(17)-dien-20-one) is a commercial product 16-dehydropregnenolone acetate (known as It is the hydrolysis product of "diene). Its congeners include: 3β-hydroxy-5α-pregna-16(17)-ene-20-one, 3β-hydroxy-5β-pregna-16(17)-ene- 20-keto, 3β, 12β-dihydroxy-5α-pregna-16(17)-en-20-one, 3β, 12α-dihydroxy-5α-pregna-16(17)-en-20-one, 3β-hydroxy-5α-pregna-12,20-dione, etc. [0003] 16-Dehydropregnenol acetate and 3β-hydroxy-5α-pregna-16(17)-en-20-one acetate are important intermediates of steroid hormone drugs. The production capacity of the former in my country is more than dry tons, and the production capacity of the latter is hundreds of tons in my country. [0004] The current production of 16-dehydropregnenol acetate and 3β-hydroxy-5α-pregna-16(17)-en-20-one a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00C07J71/00
CPCC07J71/00C07J7/00
Inventor 田伟生刘闪闪邱丙开吴秀静
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com