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Preparation method of optical pure gamma/delta-lactone spice

A lactone and fragrance technology, which is applied in the field of optically pure γ-lactone fragrance preparation, can solve the problems of many operation steps, long time, low yield, etc., and achieve the effect of good authenticity and pure aroma

Inactive Publication Date: 2010-04-14
BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current chemical resolution method and biological resolution method still have defects such as many operation steps, long time, large amount of waste liquid discharge, low yield or low optical purity.

Method used

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  • Preparation method of optical pure gamma/delta-lactone spice

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The chromatographic column specification is 250mm×10mm, the particle size is 10μm, the stationary phase filled is amylose-tris(3,5-dimethylphenylcarbamate), the column temperature is 31°C, the column pressure is 11MPa, the modifier The content of isopropanol is 2.0% v / v, the flow rate of the mobile phase is 9.4ml / min, and the wavelength of the ultraviolet detector is 220nm. 16 mg of racemic γ-nonanolide was injected for each separation, and the injection was repeated 10 times. According to the retention time of S-(-)-γ-nonanolide being 7.5 min and the retention time of R-(+)-γ-nonanolide being 8.8 min, the corresponding product fractions were collected. The solvent was removed by heating in a water bath to obtain 77 mg of S-(-)-γ-nonanolide, with an enantiomeric excess of 99%, and 78 mg of R-(+)-γ-nonanolactone, with an enantiomeric excess of 100%.

Embodiment 2

[0019] The chromatographic column specification is 250mm×10mm, the particle size is 5μm, the stationary phase filled is amylose-tris(3,5-dimethylphenylcarbamate), the column temperature is 30°C, the column pressure is 13MPa, the modifier The content of isopropanol is 2.1% v / v, the flow rate of the mobile phase is 9.2ml / min, and the wavelength of the ultraviolet detector is 220nm. 15 mg of racemic γ-undecalactone was injected for each separation, and the injection was repeated 8 times. According to the retention time of S-(-)-γ-undecalactone being 6.5 min and the retention time of R-(+)-γ-undecalactone being 7.4 min, the corresponding product fractions were collected. The solvent was removed by heating in a water bath to obtain 56 mg of S-(-)-γ-undecalactone with an enantiomeric excess of 98%, and 58 mg of R-(+)-γ-undecalactone with an enantiomeric excess of 99%.

Embodiment 3

[0021] The chromatographic column specification is 250mm×10mm, the particle size is 10μm, the stationary phase filled is cellulose-tris(benzoate), the column temperature is 31°C, the column pressure is 10MPa, the modifier isopropanol content is 1.1% v / v, and the flow The phase flow rate is 7.0ml / min, and the wavelength of the ultraviolet detector is 235nm. 15.5 mg of racemic δ-octylactone was injected for each separation, and the injection was repeated 20 times. According to the retention time of S-(-)-δ-octyl lactone being 9.5 min and the retention time of R-(+)-δ-octyl lactone being 11.2 min, the corresponding product fractions were collected. The solvent was removed by heating in a water bath to obtain 146 mg of S-(-)-δ-octylactone, with an enantiomeric excess of 99%, and 148 mg of R-(+)-δ-octylactone, with an enantiomeric excess of 99%.

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Abstract

The invention discloses a preparation method of optical pure gamma / delta-lactone spice, comprising the following steps of utilizing the supercritical CO2 fluid chromatography, selecting a proper chiral stationary phase, and directly resolving racemic gamma / delta-lactone spice under the conditions that the column temperature is 30-40 DEG C, the column pressure is 7-20 MPa , and the modifier content in CO2 mobile phase is 0.5%-10% v / v to obtain the optical pure R and S configuration gamma / delta-lactone spice products. The preparation method has the advantages of green, environment protection, mild operation condition, high separating speed, high optical purity of products, easy realization of industrial enlargement and the like.

Description

technical field [0001] The invention relates to a method for preparing optically pure γ (or δ)-lactone spices. The prepared optically pure γ (or δ)-lactones can be used as raw materials to prepare flavors such as fruit, milk, and meat. The flavors are used in food or It is used for adding fragrance to daily necessities, which has the advantages of pure fragrance and good authenticity. Background technique [0002] The present invention relates to a kind of preparation method of optically pure γ (or δ)-lactone fragrance, promptly adopts supercritical CO 2 A method for directly resolving racemic γ (or δ)-lactone fragrances by fluid chromatography to obtain optically pure R- and S-configured γ (or δ)-lactone fragrances. [0003] γ-Lactone and δ-Lactone are one of the most demanded varieties of commonly used spices, and are widely used in various food flavors such as fruits, milk, meat, and some daily flavors. Due to the existence of chiral centers in the molecules, γ-lactone ...

Claims

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Application Information

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IPC IPC(8): C11B9/00A23L1/22C07D307/33C07D309/30C07D307/58A23L27/00
CPCY02P20/54
Inventor 谢建春孙宝国程劼郑福平韩蕙澜刘玉平田红玉陈海涛黄明泉
Owner BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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