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The preparation method of royal jelly acid

A technology of royal jelly acid and acid anhydride, which is applied in the field of preparation of royal jelly acid, can solve the problems of unstable Grignard reagent, high requirements for reaction conditions, and many by-products, and solve the problems of non-recyclable use, high price, and high selectivity Effect

Inactive Publication Date: 2011-12-07
JIAXING UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation process of this process is relatively simple, but the oxidation uses PCC, the oxidant cannot be recycled and reused and there is heavy metal pollution
[0006] Chinese patent application CN101747181A uses 1,1-dialkoxy-6-hexyl magnesium halide as raw material to obtain royal jelly acid through four-step reaction. The Grignard reagent used in this process is unstable and requires high reaction conditions, so it is also Not suitable for industrial production
The disadvantage of this method is that 8-hydroxyoctanal can form a hemiacetal structure in the molecule to hinder the next step of the reaction, and the catalyst Tempo used cannot be recycled.
In addition, the present inventors used 1,8-octanediol as the starting material to prepare 8-hydroxyoctanal by the unilateral oxidation of hypochlorite by the above-mentioned method. There were many by-products in the reaction, and the yield was only about 40%. , but not as high as 98-100% of the yield reported in the patent application

Method used

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  • The preparation method of royal jelly acid
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  • The preparation method of royal jelly acid

Examples

Experimental program
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preparation example Construction

[0042] SiO 2 - Preparation of Tempo:

[0043] Add 30g of Tempo, 80mL of dimethylformamide and 70g of nano-silica into a 250ml round bottom flask, heat and stir at 90°C for 1 hour, and remove the solvent to obtain the supported product SiO 2 -Tempo 100g, dry for later use.

Embodiment 1

[0045] Add 5 grams (0.034mol) of 1,8-octanediol, 40mL of dry tetrahydrofuran and 5.47mL (0.068mol) of pyridine in a 100mL single-necked bottle, and add 3.18mL (0.034mol) of acetic anhydride dropwise to the mixture under stirring in an ice bath, After 30 minutes of dripping, the reaction was continued for 4.5 hours. This reaction adopts TLC to detect the degree of progress of the reaction (developing agent is sherwood oil / ethyl acetate (volume ratio 1: 1), R f = 0.5). After the reaction is complete, remove tetrahydrofuran and pyridine under vacuum, dissolve the residue with dichloromethane, wash with water, separate the organic phase, anhydrous MgSO 4 Dry, filter, and put the filtrate at about 0°C to crystallize overnight. Unreacted 1,8-octanediol (1 gram) was removed by filtration and reclaimed, and the solvent was evaporated from the filtrate to obtain 4.26 grams of a light yellow oily liquid product of the general formula II compound (R is methyl, i.e. 8-acetoxyoctanol). ...

Embodiment 2

[0054] Add 10 grams (0.068mol) of 1,8-octanediol, 70mL of dry tetrahydrofuran and 10.3mL (0.128mol) of pyridine in a 250mL single-necked bottle, and add 6mL (0.064mol) of acetic anhydride dropwise to the mixture under stirring in an ice bath, 40 Minutes dripping, dripping and continue to react for 4h. After the reaction was complete, after removal of tetrahydrofuran and pyridine in vacuo, the residue was washed with CH 2 Cl 2 Dissolve, wash with water, separate organic layer, anhydrous MgSO 4 Dry, filter, and put the filtrate at about 0°C to crystallize overnight. Unreacted 1,8-octanediol (2 grams) was removed by filtration and reclaimed, and the filtrate was evaporated to obtain 11.8 grams of a light yellow oily liquid product general formula II compound (R is methyl, i.e. 8-acetoxy octanol) , the yield was 98.0% (excluding the recovered 1,8-octanediol).

[0055] Add 11.8 grams (0.063mol) of 8-acetoxy octanol and 80mL of methylene chloride in a 250mL three-neck round bott...

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Abstract

The invention discloses a preparation method of royal jelly acid. The preparation method comprises the following steps: carrying out monoacylation reaction on 1,8-octanediol used as an original raw material and anhydride (RCO)2O to obtain a compound shown in a general formula II; carrying out Tempo oxidation reaction on the compound shown in the general formula II to obtain a compound shown in a general formula III, namely 8-alkanoyloxy octyl aldehyde; carrying out Witting-Horner reaction on 8-alkanoyloxy octyl aldehyde and triethyl phosphonoacetate to obtain a compound shown in a general formula IV; and hydrolyzing and acidifying the compound shown in the general formula IV to obtain the royal jelly acid. In the preparation method disclosed by the invention, 8-alkanoyloxy octyl aldehyde is prepared by carrying out monoesterification on 1,8-octanediol used as the raw material by use of the anhydride and then oxidizing, thus the selectivity and yield are high; in the Witting-Horner reaction, an ionic liquid is used as a catalyst and has the actions of the catalyst and phase transfer catalysis, thereby greatly shortening the reaction time; and the technical route has the characteristics of short route, simplicity in operation and easiness for industrial production, and is a very economical and simple method for synthesizing the royal jelly acid.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and more specifically relates to a preparation method of royal jelly acid. Background technique [0002] Royal jelly acid is the main organic component of royal jelly, and its content is one of the main indicators to measure the quality of royal jelly. Its chemical name is (E)-10-hydroxy-2-decenoic acid, or 10-HDA for short. Because of its anti-bacterial, anti-cancer, anti-radiation and strong body and other physiological functions, it has attracted the attention of workers in the fields of chemistry, biology and medicine. At present, royal jelly and its products have become best-selling products in domestic and foreign markets. Although royal jelly acid can be extracted from royal jelly, the product prepared by synthetic method has high purity and quality is easier to guarantee. There are many synthetic routes published at home and abroad, but from a practical point of view, many routes are ei...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/42C07C27/02
Inventor 宗乾收黄林美吴建一包琳
Owner JIAXING UNIV
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