Method for synthesizing 13C-labeled cholesterol carboxylic ester

A technology of cholesteryl carboxylate and cholesteryl caprylate, which is applied in the field of synthesis of 13C-labeled cholesteryl carboxylate, and can solve problems such as the absence of cholesteryl caprylate reported in literature

Inactive Publication Date: 2010-09-08
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Not yet seen related 13 Literature Report

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  • Method for synthesizing 13C-labeled cholesterol carboxylic ester
  • Method for synthesizing 13C-labeled cholesterol carboxylic ester

Examples

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Embodiment 1

[0035] Cholesteryl caprylate-octanoyl-1- 13 Synthesis of C

[0036] Under nitrogen protection, cholesterol (0.002mol) and octanoic acid-1- 13 C (0.004mol) was dissolved in DMSO (55ml), and EEDQ (0.005mol) and HOBt (0.004mol) were added at 0°C. After the addition was complete, the reaction continued for 40 hours at 10°C. After the reaction solution was concentrated, it was purified by column chromatography. A white solid was obtained (yield 85%).

Embodiment 2

[0038] Cholesteryl Laurate-Lauroyl-1- 13 Synthesis of C

[0039] Under nitrogen protection, cholesterol (0.002mol) and lauric acid-1- 13 C (0.003mol) was dissolved in dichloroethane (45ml), and EEDQ (0.005mol) and DCC (0.004mol) were added at 0°C. After the addition was completed, the reaction was continued at 20°C for 36 hours. After the reaction solution was concentrated, it was passed through the column Chromatographic purification afforded a white solid (yield 82%).

Embodiment 3

[0041] Cholesteryl Palmitate-Palmitoyl-1- 13 Synthesis of C

[0042] Under nitrogen protection, cholesterol (0.002mol) and palmitic acid-1- 13 C (0.005mol) was dissolved in chloroform (50ml), and HOBt (0.005mol) and DCC (0.004mol) were added at 10°C. After the addition, the reaction continued at 30 for 24 hours. After the reaction solution was concentrated, it was purified by column chromatography to obtain White solid (85% yield).

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Abstract

The invention discloses a method for synthesizing 13C-labeled cholesterol carboxylic ester. The 13C-labeled cholesterol carboxylic ester is synthesized by using 13C-labeled carboxylic acid and cholesterol as raw materials in the presence of condensing agent. The yield of the synthesized 13C-labeled cholesterol carboxylic ester is 80 to 90 percent, the 13C abundance is 99 atom percent, the chemical purity is 99 percent, and the 13C-labeled cholesterol carboxylic ester fully meets the requirement of medicinal reagent. The 13C-labeled cholesterol carboxylic ester is a medicinal 13C respiration reagent, and can be used for diagnosis of pancreatic disease and the like.

Description

technical field [0001] The present invention relates to a synthesis method of reagents for disease diagnosis, in particular to a 13 The synthetic method of C labeled cholesteryl carboxylate, it is with 13 C-labeled carboxylic acid and cholesterol as raw materials, synthesized in the presence of a condensing agent 13 C marks cholesteryl carboxylate. Background technique [0002] 13 C-labeled cholesteryl carboxylate (Cholesteryl carboxylic acid esters- 13 C), including carboxyl for 13 C-labeled cholesteryl carboxylate-carboxyl-1- 13 C and cholesteryl carboxylate-carboxyl-1,2- 13 C 2 and cholesteryl for 13 C-labeled cholesteryl carboxylate-cholesteryl-3- 13 C, cholesteryl carboxylate-cholesteryl-4- 13 C and cholesteryl carboxylate-cholesteryl-3,4- 13 C 2 . [0003] 13 C-labeled cholesteryl carboxylate is usually a white crystalline powder with optical activity, insoluble in water, soluble in alcohol, n-hexane, dichloromethane and chloroform. For example, the spec...

Claims

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Application Information

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IPC IPC(8): C07J9/00C07J75/00C07B59/00
Inventor 卢伟京李帅卢浩徐仲杰侯秀红李美华李孝武杨维成石洵予
Owner SHANGHAI RES INST OF CHEM IND
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