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

A method for preparing thioalkyl/alkenyl cysteine ​​sulfoxide by fractional crystallization

A technology of cysteine ​​sulfoxide and thioalkyl, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as by-products and impurities, affecting product purity, toxicity, etc., to achieve Avoid complex process, high product purity and improved yield

Active Publication Date: 2016-07-20
JIANGNAN UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are also some disadvantages: firstly, because the free mercapto and allyl groups in the reactant are too reactive, many by-products and impurities are easily generated, and the purity of the product cannot be guaranteed; secondly, the product is an enantiomer with left-handed (-) and The two forms of dextrorotation (+) affect the purity of the product
Moreover, the product is easy to form a racemate, which has no optical activity, and its physiological activity is uncertain compared with natural products, and may even be toxic. Therefore, the enantiomers in the product must be separated, and only natural D-cysteine ​​sulfoxide

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

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A method for preparing thioalkyl/alkenyl cysteine ​​sulfoxide by fractional crystallization
  • A method for preparing thioalkyl/alkenyl cysteine ​​sulfoxide by fractional crystallization
  • A method for preparing thioalkyl/alkenyl cysteine ​​sulfoxide by fractional crystallization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Preparation of (+)S-methyl-L-cysteine ​​sulfoxide ((+)MCSO)

[0046] (1) Take L-cysteine ​​hydrochloride (1mol) and evenly disperse in 3L absolute ethanol, add 3.5mol sodium hydroxide solution (20mol / L) dropwise under magnetic stirring at room temperature, and continue stirring for 5min ; Then add 1.1mol methyl bromide, keep a constant temperature for 6h, generate deoxythiomethylcysteine ​​sulfoxide (MCS) crude solution. The solution was transferred to a clean container, and the pH was adjusted to 5.2 with acid at 30°C. White deoxygenated MCS crystals were formed at 4°C for 12h.

[0047] (2) Filter the MCS crystals obtained in step (1), dry them at 40°C, redissolve them in 10 mL of distilled water containing 1% glacial acetic acid, and heat to boiling. Pour the solution into 150 mL of boiling absolute ethanol for recrystallization. At this time, the MCS crystals will stand upside down in the solvent and the solution will become cloudy. The solution was plac...

Embodiment 2

[0052] Example 2: Preparation of (+) S-allyl-L-cysteine ​​sulfoxide ((+) 2-PeCSO)

[0053] (1) Take L-cysteine ​​(1mol) and evenly disperse it in 3L absolute ethanol, add 3.5mol sodium hydroxide solution (20mol / L) dropwise under magnetic stirring at room temperature, and continue stirring for 10min; then add 1.1mol of allyl bromide was reacted at room temperature for 6 hours to generate a crude solution of deoxythioallyl cysteine ​​sulfoxide (2-PeCS). The solution was transferred to a clean container, and the pH was adjusted to 5.5 with acid at 30°C. White deoxygenated 2-PeCS crystals were formed at 4°C for 12h.

[0054] (2) Filter the 2-PeCS crystal obtained in step (1), dry it at 50°C, then redissolve it in 10 mL of distilled water containing 1% glacial acetic acid, and heat it to boiling. Pour the solution into 150 mL of boiling ethanol for recrystallization. The solution was placed at 4°C for 12 hours for recrystallization, and the crystals were filtered and dried at 50°...

Embodiment 3

[0058] Example 3: Preparation of (+) S-propyl-L-cysteine ​​sulfoxide ((+) PCSO)

[0059] (1) Take L-cysteine ​​(1mol) and evenly disperse it in 3L absolute ethanol, add 3.5mol sodium hydroxide solution (20mol / L) dropwise under magnetic stirring at room temperature, and continue stirring for 10min; then add 1.1 mol of 1-bromopropane was reacted at room temperature for 6 hours to generate a crude solution of deoxythiopropyl cysteine ​​sulfoxide (PCS). The solution was transferred to a clean container, and the pH was adjusted to 5.18 with acid at 30°C. White deoxidized PCS crystals were formed at 4°C for 12h.

[0060] (2) Filter the PCS crystals obtained in step (1), dry them at 50°C, then redissolve them in 10 mL of distilled water containing 1% glacial acetic acid, and heat to boiling. Pour the solution into 150 mL of boiling ethanol for recrystallization. The solution was placed at 4°C for 12 hours for recrystallization, and the crystals were filtered and dried at 50°C to ob...

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
melting pointaaaaaaaaaa
specific rotationaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a method for preparing thioalkyl / alkenyl cysteine ​​sulfoxide by fractional crystallization, which belongs to the technical field of compound preparation. In the present invention, cysteine ​​or its salts, sodium hydroxide solution, and R group (alkyl, alkenyl) sources are sequentially added to absolute ethanol to react to synthesize crude ACSs, and the ACSs are recrystallized and purified, and then oxidized to ACSOs, dextro-ACSOs in natural state obtained by fractional crystallization; different kinds of ACSOs contained in Allium were synthesized by replacing the source of R group; enantiomers in racemates were separated by fractional crystallization body, to obtain natural ACSOs dextrorotary substance, which has optical activity. Compared with the traditional extraction method, this method has high yield and high purity, avoids the complicated process of traditional extraction, and the product has optical activity, and its physical properties are close to natural extracts. The products are used in health care products, pharmaceuticals and other fields to exert the antibacterial, anticancer and blood lipid lowering effects of ACSOs, or as intermediates such as the active ingredient diallylthiosulfinate of the genus Allium.

Description

technical field [0001] The invention relates to a method for chemically preparing thioalkyl (alkenyl) cysteine ​​sulfoxides (ACSOs), belonging to the technical field of compound preparation. Background technique [0002] Studies have confirmed that the thioalkyl (alkenyl) cysteine ​​sulfoxides (ACSOs) rich in allium plants have antibacterial, antiviral, blood lipid-lowering, anti-aging, anti-tumor, and promotion of cancer cell apoptosis, etc. Physiologically active, with strong medicinal value. [0003] Common ACSOs in Alliums include: S-methyl-L-cysteine ​​sulfoxide (MCSO); S-ethyl-L-cysteine ​​sulfoxide (ECSO); S-propyl-L- Cysteine ​​sulfoxide (PCSO); S-propenyl-L-cysteine ​​sulfoxide (2-PeCSO); S-allyl-L-cysteine ​​sulfoxide (1-PeCSO); S -Butyl-L-cysteine ​​sulfoxide (BCSO). [0004] Alliin is the most important ACSOs in allium plants. Alliin, ginkgo leaf extract and ginsenoside are known as the three most important and promising drugs in the 21st century. [0005] At...

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 Patents(China)
IPC IPC(8): C07C317/48C07C315/02
Inventor 孔祥珍陈海桥华欲飞丁秀臻张彩猛陈业明
Owner JIANGNAN UNIV
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