Full racemic phytol composition, and preparation method and application thereof

A technology of phytoalcohol and composition, which is applied in the application field of the whole racemic phytoalcohol composition and the preparation of vitamin K1, can solve the problems of reducing, not providing, and difficult to control the content of Z-isomer

Pending Publication Date: 2020-11-27
SICHUAN HAISCO PHARMA CO LTD
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, according to the prior art, it is difficult to control the Z-isomer content to be lower than 15.0% when the double bond of isophytol is rearranged, and the prior art does not provide further reduction of vitamin K in subsequent intermediates or products. 1 Method for Z-isomer content in

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
  • Full racemic phytol composition, and preparation method and application thereof
  • Full racemic phytol composition, and preparation method and application thereof
  • Full racemic phytol composition, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Example 1 Preparation of the all-racemic phytoalcohol composition (formula VII) with high E-type configuration content

[0084] (1), the preparation of the composition shown in formula V-a

[0085]

[0086] Dissolve 5 kg of isophytic alcohol (formula III) in 18 kg of methyl tert-butyl ether, stir and cool to below -10°C, and add dropwise 2.28 kg of phosphorus tribromide and methyl tert-butyl ether under temperature control below 0°C 2kg of the solution prepared; after dropping, continue to control the temperature and react below 0°C; after TLC monitors the reaction, add 1 kg of water dropwise under the temperature control below 0°C; 5-6. Dry over anhydrous sodium sulfate, filter, and concentrate to obtain the composition represented by formula V-a, which is directly used in the next reaction.

[0087] (2), the preparation of the composition shown in formula VIII-a

[0088]

[0089] Add the composition represented by the formula V-a obtained above, 268 g of tetrabu...

Embodiment 2

[0095] Example 2 Preparation of the all-racemic phytoalcohol composition (formula VII) with high E-type configuration content

[0096] (1), the preparation of the composition shown in formula V-b

[0097]

[0098] Mix 0.5kg of isophytic alcohol (formula III), 3.5kg of concentrated hydrochloric acid and 20g of tetramethylammonium chloride, and stir the reaction at 10-20°C under temperature control; after the reaction is monitored by TLC, add n-heptane for extraction; the obtained organic The phase was washed with water to pH=5-6, dried over anhydrous sodium sulfate, filtered and concentrated to obtain the composition represented by formula V-b, which was directly used in the next reaction.

[0099] (2), the preparation of the composition shown in formula VIII-b

[0100]

[0101] Add the composition shown in the formula V-b obtained above, 30 g of tetramethylammonium chloride and 344 g of sodium formate into 5 kg of acetonitrile, and stir the reaction at 50-60 ° C; TLC mo...

Embodiment 3

[0107] Example 3 Preparation of the all-racemic phytoalcohol composition (formula VII) with high E-type configuration content

[0108] (1), the preparation of the composition shown in formula V-a

[0109]

[0110] Dissolve 5 kg of isophytic alcohol (formula III) in 18 kg of methyl tert-butyl ether, stir and cool to below -10°C, and add 2.28 kg of phosphorus tribromide and methyl tert-butyl ether dropwise under temperature control below 0°C 2kg of the solution; after dropping, continue to control the temperature below 0°C to react; after the reaction is monitored by TLC, add 1 kg of water dropwise at the temperature below 0°C; The aqueous solution was washed until the pH of the aqueous phase = 5-6, and the obtained organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to obtain the composition represented by formula V-a, which was directly used in the next reaction.

[0111] (2), the preparation of the composition shown in formula VIII-a

[0112...

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
Specific rotationaaaaaaaaaa
Login to view more

Abstract

The present invention provides a full racemic phytol composition with high E-configuration content, a preparation method of the full racemic phytol composition and applications of the full racemic phytol composition in preparation of vitamin K1. The full racemic phytol composition comprises Z-configuration full racemic phytol and E-configuration full racemic phytol, wherein a ratio of Z / (Z+E) is less than or equal to 15%. The preparation method comprises the following steps: with isophytol as a raw material, performing halogenation, esterification, ester group removal reaction and the like toobtain the full racemic phytol composition with high E-configuration content.

Description

technical field [0001] The invention provides a composition and its preparation method and application, in particular to a whole racemic phytoalcohol composition, its preparation method and its use in the preparation of vitamin K 1 Applications in organic chemistry and pharmacy. Background technique [0002] Vitamin K 1 , naturally occurring in a variety of plants, the chemical name of its naturally occurring form is 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexade-2-ene -1-yl]-1,4-naphthoquinone, the chemical structural formula is as shown in formula I-1. [0003] [0004] Vitamin K 1 It is a fat-soluble vitamin drug that plays a very important role in human blood coagulation, energy metabolism and body tissue activities. Vitamin K 1 May be used in the treatment of vitamin K 1 Bleeding caused by deficiency, such as bleeding caused by obstructive jaundice, biliary fistula, chronic diarrhea, hypoprothrombinemia caused by coumarins and sodium salicylate, neonatal h...

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
IPC IPC(8): C07C50/14C07C46/00C07C50/20C07C17/16C07C21/14C07C21/04C07C67/11C07C69/145C07C69/07C07C29/09C07C33/03
CPCC07C50/14C07C46/00C07C50/20C07C17/16C07C21/14C07C21/04C07C67/11C07C29/095C07C33/03C07B2200/09C07C2603/86C07C2602/10C07B2200/07C07C69/145C07C69/07
Inventor 易仕旭何永耀江伟叶观浩李彦霖唐佳宾高炳坤罗杰
Owner SICHUAN HAISCO PHARMA CO LTD
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
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap