Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Process for preparing carotenoid polyene chain compounds and intermediates for preparing same

A compound, monoxide technology, applied in the field of lycopene, can solve problems such as not easy to form double bonds

Inactive Publication Date: 2003-10-29
具相湖 +1
View PDF0 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The method for synthesizing lycopene in Reaction Scheme 2 is quite simple, but it is not easy to form a double bond with trans configuration

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

[0066] Example 1: 2-Methyl-4-phenylthio-2-butenyl-1-ol

[0067] Dissolve isoprene monoxide (0.30 ml, 3.1 mmol) in N,N-dimethylformamide (DMF) (7 ml), and add cuprous iodide (CuI) to it at 0°C (15 mg, 0.08 mmol) and thiophenol (PhSH) (0.33 mL, 3.2 mmol). The final reaction mixture was stirred at the same temperature for about 6 hours.

[0068] When the reaction was complete, the reaction mixture was diluted with ether, then washed three times with 1M-HCl (10 mL×3), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2-methyl-4-phenylthio-2-butenyl-1-ol (0.52 g, 2.7 mmol ) (Yield: 87%). according to 1 According to the analysis data of H-NMR and gas chromatography, the ratio of trans-type and cis-type double bonds is not less than 6:1.

[0069] 1 H-NMR: trans δ 1.56(s, 3H), 2.38(br s, 1H), 3.55(d, 2H, J=7.7Hz), 3.92(s, 2H), 5.54(t, 1...

Embodiment 2

[0072] Example 2: 4-bromo-3-methyl-2-butenylphenyl sulfide

[0073] Slowly add ether (80 ml), PBr 3 (16.5 g, 61 mmol). The final reacted mixture was stirred at 0°C for about 1 hour. When the reaction was completed, the reaction mixture was diluted with ether, washed with distilled water, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-bromo-3-methyl-2-butenylphenyl sulfide (26.8 g, 104 mmol) ( Yield: 85%).

[0074] 1 H-NMR: trans δ1.64(s, 3H), 3.51(d, 2H, J=7.7Hz), 3.92(s, 2H), 5.72(t, 1H, J=7.7Hz), 7.18~7.41( m, 5H); cis δ1.85(s, 3H), 3.56(d, 2H, J=7.9Hz), 3.79(s, 2H), 5.52(t, 1H, J=7.9Hz), 7.18~7.41 (m, 5H).

[0075] 13 C-NMR: δ 14.7, 32.4, 40.4, 125.9, 126.7, 128.9, 130.9, 135.4, 135.5.

Embodiment 3-1

[0076] Example 3-1: 5-Benzenesulfonyl-1-phenylthio-3,7,11-trimethyl-2,6,10-dodecatriene

[0077] Geranyl sulfone (28.7 g, 103 mmol) was dissolved in THF (150 ml), and then n-BuLi (1.6M hexane-solvent solution / 64 ml, 103 mmol) was slowly added thereto at 0°C . The final reacted mixture was stirred for about 20 minutes. 4-Bromo-3-methyl-2-butenylphenylsulfide (29.1 g, 113 mmol) was added to the reaction mixture. The reaction temperature was slowly raised to room temperature, and the mixture was stirred at the same temperature for about 11 hours.

[0078] 100 mL of ether was added to the reaction mixture, and the final mixture was washed well with 1M-HCl aqueous solution (20 mL×2) and distilled water (30 mL). The mixture was dried over anhydrous sodium sulfate and filtered.

[0079] The filtrate was concentrated by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 5-benzenesulfonyl-1-phenylthio-3,7,11-trimethyl-2,6...

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

No PUM Login to View More

Abstract

The present invention provides an intermediate compound used for synthesis of polyene chain structure, that is an important moiety of carotenoid compounds, a process for preparing the same, and carotenoid polyene chain compounds prepared by using the intermediate, and, in particular, a process for preparing lycopene. The process for preparing the carotenoid polyene chain compound employs an allylic sulfone compound as starting material, which is reacted with C-5 sulfide compound to extend the carbon chain. The resultant thio-sulfone compound is oxidized, and the obtained disulfone compound is combined with C-10 di(haloallylic) sulfide compound to form a chain compound containing the desired number of carbon atoms. Then, the diallylic sulfone obtained by oxidation of the diallylic sulfide is subjected to Ramberg-Baklund reaction in order to form the central triene bond. After removal of sulfonyl groups, carotenoid polyene chain compound is obtained.

Description

technical field [0001] The invention relates to a method for preparing carotenoid polyene chain compounds. More specifically, it relates to intermediate compounds for the synthesis of polyene chain structures, methods for preparing such compounds and methods for preparing carotenoid polyene chain compounds, especially lycopene, using the intermediate compounds. Background technique [0002] Carotenoids have a polyene chain structure. Specific examples of this compound include β-carotene, lycopene, astaxanthin, nopain and the like. Carotenoid compounds have been widely used as natural dyes, and it has recently been reported that these compounds have good anticancer effects due to their ability to selectively react with free radicals and singlet oxygen atoms known as carcinogens. Against this background, various commercial products containing carotene, including cosmetics and flavored foods, have been marketed. However, there are still conflicting views on the anticancer ef...

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): C07C323/09C07B61/00C07C1/32C07C11/21C07C315/02C07C315/04C07C317/08C07C317/34C07C317/44C07C319/18C07C319/20C07C323/01C07C323/05C07C323/14C07C323/65
CPCC07C1/322C07C315/02C07C315/04C07C319/18C07C319/20C07C323/05C07C323/14C07C317/08C07C323/65C07C11/21C07C323/01
Inventor 具相湖池敏求
Owner 具相湖
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap 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