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Method for performing pre-column derivation high performance liquid chromatography chiral resolution on DL-menthol by using chiral derivation reagent

A technology of high performance liquid chromatography and derivatization reagent, which is applied in the field of pre-column derivatization high performance liquid chromatography analysis and separation, can solve the problems of high cost, difficult recovery, low sensitivity, etc., and achieves low cost, accurate separation and separation, and high sensitivity. Effect

Active Publication Date: 2015-04-22
上海柏狮生物科技有限公司
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Problems solved by technology

However, this separation technology also has major disadvantages: first, the optically active reagents used in the reaction are expensive and difficult to recycle; second, the subsequent separation process is complicated and cannot be mass-produced
The chiral analysis methods currently include: using substituted β-cyclodextrin as a stationary phase for gas chromatographic separation, but complete separation cannot be achieved; Liquid chromatography uses chiral packing for separation, which is expensive

Method used

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  • Method for performing pre-column derivation high performance liquid chromatography chiral resolution on DL-menthol by using chiral derivation reagent
  • Method for performing pre-column derivation high performance liquid chromatography chiral resolution on DL-menthol by using chiral derivation reagent
  • Method for performing pre-column derivation high performance liquid chromatography chiral resolution on DL-menthol by using chiral derivation reagent

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preparation example Construction

[0033] The synthetic method of D-mandelic acid-DL-menthyl ester used in each embodiment of the present invention, (+)-naproxen-DL-menthyl ester, concrete steps are as follows:

[0034] Add chiral aromatic acid, DL-menthol and p-toluenesulfonic acid monohydrate sequentially into a 250 mL three-neck flask equipped with a thermometer, water separator, spherical condenser and drying tube, and the molar ratio is 1.2:1:0.05 , dissolved in 100 mL toluene, add toluene to the water separator, heat to 110 o C was stirred and refluxed overnight, and TLC detected that the reaction of the raw materials was complete. Cool the reaction system to room temperature, add 20 mL of water to the system to quench the reaction, stir for 10 min and then separate the liquids, extract the aqueous phase with ethyl acetate, and wash the combined organic phase with saturated sodium bicarbonate solution and saturated brine in sequence , dried over anhydrous magnesium sulfate and concentrated to obtain crud...

Embodiment 1

[0037] A method for performing pre-column derivatization high performance liquid chromatography chiral resolution of DL-menthol by using a chiral derivatization reagent, the specific steps are as follows:

[0038] (1) Add chiral aromatic acid D-mandelic acid (5.84 g, 38.39 mmol), DL-menthol (5 g, 31.99 mmol) and catalyst p-toluenesulfonic acid monohydrate (0.31 g, 1.60 mmol), calculated by molar ratio, that is, chiral aromatic acid: DL-menthol: catalyst monohydrate p-toluenesulfonic acid is 1.2:1:0.05, then add 100 mL of toluene as solvent, shake well and add magneton, install Water separator, spherical condenser and drying pipe, fill the water separator with toluene, heat it at about 110°C, stir and reflux, condense and separate the water. After the reaction is completed, the water in the water separator will no longer increase. Cool the reaction system to room temperature, add 20 mL of water, separate the organic layer, wash the organic layer with saturated sodium bicarbonat...

Embodiment 2

[0057] A method for performing pre-column derivatization high performance liquid chromatography chiral resolution of DL-menthol by using a chiral derivatization reagent, the specific steps are as follows:

[0058]In a 250mL three-necked flask, the chiral aromatic acid (+)-naproxen (8.84 g, 38.39 mmol), DL-menthol (5 g, 31.99 mmol) and the catalyst p-toluenesulfonic acid monohydrate (0.31 g, 1.60 mmol), calculated by molar ratio, that is, chiral aromatic acid: DL-menthol: catalyst monohydrate p-toluenesulfonic acid is 1.2:1:0.05, then add 100mL of toluene as solvent, shake well and add magnets, install Water tank, spherical condenser and drying tube, fill the water separator with toluene, heat it at about 110°C, stir and reflux, condense and separate the water. After the reaction is completed, the water in the water separator will no longer increase. Cool the system to room temperature, add 20mL of water, separate the organic layer, wash the organic layer with saturated sodium ...

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Abstract

The invention discloses a method for performing pre-column derivation high performance liquid chromatography chiral resolution on DL-menthol by using a chiral derivation reagent, which comprises the following steps: performing pre-column derivation reaction on chiral aromatic acid and DL-menthol to obtain a DL-menthol ester derivative having ultraviolet absorption property; through a high performance liquid chromatograph provided with an ultraviolet-visible detector, by using a common non-chiral silica gel chromatographic column and adopting a water phase and an organic phase as mobile phases for reversed-phase elution, preparing the obtained DL-menthol ester derivative into a 0.5-1.0 mg / mL sample solution, wherein the flow rate is controlled at 0.4-1.2 mL / min, the sample size is 2-10 muL, and the detection wavelength is 210-285 nm; then performing chromatographic column separation under the condition that a column oven of the chromatographic column is at 20-35 DEG C to perform separation and detection on the obtained DL-menthol ester diastereoisomer; and finally, hydrolyzing respectively to obtain D-menthol and L-menthol.

Description

technical field [0001] The invention relates to a pre-column derivatization high-performance liquid chromatography analysis and separation method using a chiral derivatization reagent. Specifically, a chiral aromatic acid is used as a derivatization reagent to perform pre-column ultraviolet derivatization on DL-menthol to obtain non- For enantiomeric derivatives, achiral conventional C18 chromatographic columns and diode array detectors are used to resolve and detect derivatives. Background technique [0002] Mint (Mentha haplocalyx), also known as mint, jelly mother, nightshade, water mint, fish herb, dandelion, tomato, etc., is a perennial herb of Lamiaceae. It is a kind of special economic value. The aromatic crops are widely distributed all over the country. Menthol, scientific name 5-methyl-2-isopropylcyclohexanol, commonly known as menthol, organic compound, colorless needle crystal or granular. As the main component of peppermint and peppermint essential oils, menth...

Claims

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Application Information

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IPC IPC(8): C07C35/12C07C29/88G01N30/28
CPCC07B2200/07C07C29/88C07C67/08C07C67/56C07C2601/14G01N30/28C07C35/12C07C69/013C07C69/732C07C69/736
Inventor 潘仙华于一文徐娜刘烽李晓军张瑞敏陈思羽王亚萍于万盛王琨
Owner 上海柏狮生物科技有限公司
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