Cryptochlorogenic acid preparation method

Abstract

The present invention discloses a cryptochlorogenic acid preparation method comprising the following steps: taking chlorogenic acid, dissolving the chlorogenic acid in methanol, then adding 1-2mol / L hydrochloric acid for the reaction while stirring for 6-8h, using a 1-2mol / L NaOH solution for adjusting pH to be neutral, concentrating, dissolved in methanol, filtering, concentrating under reduced pressure, adding water for dissolving, and filtering to obtain a filtrate; taking the filtrate for pretreatment by a reverse phase C18 column, washing with water, collecting a water washing solution, concentrating, centrifuging, filtering, and preparing cryptochlorogenic acid by reverse phase industrial preparative chromatography. According to the cryptochlorogenic acid preparation method, best acid conversion conditions and alkali neutralization reaction conditions can be obtained by screening by system experiments, the high purity cryptochlorogenic acid can be prepared by the reverse phase industrial preparative chromatography, and the method is high in yield and suitable for large-scale preparation, and achieves good technical results.

Description

technical field

[0001] The invention relates to a preparation method of an organic acid, in particular to a preparation method of cryptochlorogenic acid. Background technique

[0002] Cryptochlorogenic acid is 4-caffeoylquinic acid, which belongs to the monocaffeoylquinic acid compound and is an isomer of chlorogenic acid (3-caffeoylquinic acid). In recent years, scholars at home and abroad have conducted in-depth research on the pharmacological activities of caffeoylquinic acid compounds, and found that they have some important biological activities, such as antioxidant, anti-inflammatory, antibacterial, antiviral, inhibiting smooth muscle contraction, lowering blood lipids, etc. It has clinical application value and is expected to play an important role in the treatment of viral hepatitis and cervical cancer. However, at present, such compounds are only in the laboratory research stage, and there is no method and technology for large-scale preparation, which greatly limit...

Examples

Embodiment 1

[0041] 1, a preparation method of cryptochlorogenic acid, it comprises the following steps:

[0042] (1) Take 10 g of chlorogenic acid, add 10 times the volume concentration of 50% methanol to dissolve, add 20 times the volume of 1mol / L hydrochloric acid, stir and react on a 60°C water bath for 6 hours, and cool down to room temperature after the reaction to obtain a reaction solution ;

[0043] (2) Add 1mol / L NaOH solution to the reaction solution to adjust the pH to neutrality, concentrate to dryness under reduced pressure below 50°C, add methanol to dissolve, filter the precipitated white solid, and concentrate the filtrate to dryness under reduced pressure below 50°C, add a small amount of Dissolve in water, filter to obtain filtrate;

[0044] (3) take the filtrate and pass through reverse phase C 18 The column was pretreated, washed with water, collected and concentrated, centrifuged, passed through a 0.45 μm filter membrane, and prepared by industrial preparative chromat...

Embodiment 2

[0049] 1, a preparation method of cryptochlorogenic acid, it comprises the following steps:

[0050] (1) Take 200 g of chlorogenic acid, add 10 times the volume concentration of 50% methanol to dissolve, add 20 times the amount of 1mol / L hydrochloric acid, stir and react on a 60°C water bath for 6h, and cool down to room temperature after the reaction to obtain a reaction solution ;

[0051] (2) Add 1mol / L NaOH solution to the reaction solution to adjust the pH to neutrality, concentrate to dryness under reduced pressure below 50°C, add methanol to dissolve, filter the precipitated white solid, and concentrate the filtrate to dryness under reduced pressure below 50°C, add a small amount of Dissolve in water, filter to obtain filtrate;

[0052] (3) take the filtrate and pass through reverse phase C 18 The column was pretreated, washed with water, collected and concentrated, centrifuged, passed through a 0.45 μm filter membrane, and prepared by industrial preparative chromatog...

Embodiment 3

[0057] A preparation method of cryptochlorogenic acid, comprising the following steps:

[0058] (1) Take 500 g of chlorogenic acid, add 10 times the volume concentration of 80% methanol to dissolve, add 10 times the volume of 2mol / L hydrochloric acid, stir and react on a 60°C water bath for 8h, and cool down to room temperature after the reaction to obtain a reaction solution ;

[0059] (2) Add 2mol / L NaOH solution to the reaction solution to adjust the pH to neutrality, concentrate to dryness under reduced pressure below 50°C, add methanol to dissolve, filter the precipitated white solid, and concentrate the filtrate to dryness under reduced pressure below 50°C, add a small amount of Dissolve in water, filter to obtain filtrate;

[0060] (3) take the filtrate and pass through reverse phase C 18 The column was pretreated, washed with water, collected and concentrated, centrifuged, passed through a 0.45 μm filter membrane, and prepared by industrial preparative chromatography...

technical field

[0001] The invention relates to a preparation method of an organic acid, in particular to a preparation method of cryptochlorogenic acid. Background technique

[0002] Cryptochlorogenic acid is 4-caffeoylquinic acid, which belongs to the monocaffeoylquinic acid compound and is an isomer of chlorogenic acid (3-caffeoylquinic acid). In recent years, scholars at home and abroad have conducted in-depth research on the pharmacological activities of caffeoylquinic acid compounds, and found that they have some important biological activities, such as antioxidant, anti-inflammatory, antibacterial, antiviral, inhibiting smooth muscle contraction, lowering blood lipids, etc. It has clinical application value and is expected to play an important role in the treatment of viral hepatitis and cervical cancer. However, at present, such compounds are only in the laboratory research stage, and there is no method and technology for large-scale preparation, which greatly limit...

Examples

Embodiment 1

[0041] 1, a preparation method of cryptochlorogenic acid, it comprises the following steps:

[0042] (1) Take 10 g of chlorogenic acid, add 10 times the volume concentration of 50% methanol to dissolve, add 20 times the volume of 1mol / L hydrochloric acid, stir and react on a 60°C water bath for 6 hours, and cool down to room temperature after the reaction to obtain a reaction solution ;

[0043] (2) Add 1mol / L NaOH solution to the reaction solution to adjust the pH to neutrality, concentrate to dryness under reduced pressure below 50°C, add methanol to dissolve, filter the precipitated white solid, and concentrate the filtrate to dryness under reduced pressure below 50°C, add a small amount of Dissolve in water, filter to obtain filtrate;

[0044] (3) take the filtrate and pass through reverse phase C 18 The column was pretreated, washed with water, collected and concentrated, centrifuged, passed through a 0.45 μm filter membrane, and prepared by industrial preparative chromat...

Embodiment 2

[0049] 1, a preparation method of cryptochlorogenic acid, it comprises the following steps:

[0050] (1) Take 200 g of chlorogenic acid, add 10 times the volume concentration of 50% methanol to dissolve, add 20 times the amount of 1mol / L hydrochloric acid, stir and react on a 60°C water bath for 6h, and cool down to room temperature after the reaction to obtain a reaction solution ;

[0051] (2) Add 1mol / L NaOH solution to the reaction solution to adjust the pH to neutrality, concentrate to dryness under reduced pressure below 50°C, add methanol to dissolve, filter the precipitated white solid, and concentrate the filtrate to dryness under reduced pressure below 50°C, add a small amount of Dissolve in water, filter to obtain filtrate;

[0052] (3) take the filtrate and pass through reverse phase C 18 The column was pretreated, washed with water, collected and concentrated, centrifuged, passed through a 0.45 μm filter membrane, and prepared by industrial preparative chromatog...

Embodiment 3

[0057] A preparation method of cryptochlorogenic acid, comprising the following steps:

[0058] (1) Take 500 g of chlorogenic acid, add 10 times the volume concentration of 80% methanol to dissolve, add 10 times the volume of 2mol / L hydrochloric acid, stir and react on a 60°C water bath for 8h, and cool down to room temperature after the reaction to obtain a reaction solution ;

[0059] (2) Add 2mol / L NaOH solution to the reaction solution to adjust the pH to neutrality, concentrate to dryness under reduced pressure below 50°C, add methanol to dissolve, filter the precipitated white solid, and concentrate the filtrate to dryness under reduced pressure below 50°C, add a small amount of Dissolve in water, filter to obtain filtrate;

[0060] (3) take the filtrate and pass through reverse phase C 18 The column was pretreated, washed with water, collected and concentrated, centrifuged, passed through a 0.45 μm filter membrane, and prepared by industrial preparative chromatography...

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