Process for producing oleanolic acid and/or maslinic acid

A technology of oleanolic acid and maslinic acid, which is applied in the separation/purification of carboxylic acid compounds, steroids, organic chemistry, etc., can solve the problems of high production cost and unstable supply of compounds, and achieve the effect of low production cost

Inactive Publication Date: 2003-10-15
THE NISSHIN OILLIO GRP LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore there is a problem that these compounds cannot be supplied stably, and they require high production costs
[0008] In addition, no method has been found for the preparation of either or both of oleanolic acid and maslinic acid in a highly purified state from the same natural raw material, nor is there any method for industrially efficient large-scale preparation of these substance

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0119] Add 10 times the volume of hexane to 1 kg of the pressing residue produced in the olive oil preparation process and originating in Italy, at 20 ° C and 1.02 × 10 5 Extraction was continued at Pa for 3 hours while vigorously stirring the extraction system. After the entire extraction system passed through the filter, the resulting filtrate was concentrated to dryness, thereby obtaining 117 g of the extracted product. The contents of oleanolic acid and its salts and maslinic acid and its salts were determined by gas chromatography (GC).

[0120] All the extracted products were processed by silica gel column chromatography using a column packed with 40 volumes of silica gel (4680 g). First, an eluent (3:1 hexane / ethyl acetate mixed solvent) was passed through the column in an amount about 5 times (23.4 L) the volume of silica gel packed in the column to remove various undesired components. Subsequently, an eluent (3:1 hexane / ethyl acetate mixed solvent) was passed throug...

preparation example 2

[0124] To 1kg of olive oil production process and originate from Italian pressing residue, add 10 volumes of hydrous ethanol with an ethanol content of 65% by mass, at 20°C and 1.02×10 5 Extraction was continued at Pa for 3 hours while vigorously stirring the extraction system. After the entire extraction system passed through the filter, the resulting filtrate was concentrated to dryness, thereby obtaining 58.9 g of the extracted product. The contents of oleanolic acid and its salts and maslinic acid and its salts were determined by GC technique.

[0125] To the extracted product, 3 L of n-butanol and 3 L of water were added, followed by stirring the resulting mixture for 10 minutes, and the system was separated into an n-butanol phase and an aqueous phase. After removal of n-butanol from the n-butanol phase, the resulting residue was vacuum-dried to obtain 46.2 g of a concentrate.

[0126] The whole concentrate was worked up by silica gel column chromatography using a colu...

preparation example 3

[0132] Add 10 volumes of hexane to 1 kg of the extraction residue produced in the olive oil preparation process and originate from Italy, at 20°C and 1.02×10 5 Extraction was continued at Pa for 3 hours while vigorously stirring the extraction system. After the entire extraction system passed through the filter, the resulting filtrate was concentrated to dryness, thereby obtaining 25 g of the extracted product. The contents of oleanolic acid and its salts and maslinic acid and its salts were determined by GC technique.

[0133] All the extracted products were processed by silica gel column chromatography using a column packed with 40 volumes of silica gel (1000 g). First, an eluent (3:1 hexane / ethyl acetate mixed solvent) was passed through the column in an amount about 5 times (5 L) the volume of silica gel packed in the column to remove various undesired components. Subsequently, an eluent (3:1 hexane / ethyl acetate mixed solvent) was passed through the column in an amount ...

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PUM

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Abstract

A process for producing oleanolic acid and / or maslinic acid and physiologically acceptable salts thereof characterized by comprising extracting with water and / or an organic solvent olive plant and / or products formed in the course of the production of olive oil and then concentrating and / or fractionating and purifying.

Description

technical field [0001] The present invention relates to a process for the preparation of oleanolic acid and / or maslinic acid and their physiologically acceptable salts, in particular to the preparation of oleanolic acid from the olive plant (Olea oleifera) and / or from the products obtained during the production of olive oil AHA and / or maslinic acid approach. Background of the invention [0002] Olive belongs to the olive plant of Oleaceae, and it is used as a raw material for food. The olive is a plant that has long been widely cultivated and is now commonly cultivated on a large scale in the Mediterranean coastal regions. As for its application, it is very important, in almost all countries in the world, including Japan and the United States, not to mention European countries, it is not only used as an oil raw material such as olive oil, but also as a salt preservation food or cosmetic material , and even herbs (medicinal plants). Additionally, olive oil cakes have been ...

Claims

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Application Information

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IPC IPC(8): C07J63/00
CPCC07J63/008C07C51/42
Inventor 久野宪康筱原刚
Owner THE NISSHIN OILLIO GRP LTD
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