JPS60204739A - Powder containing eicosapolyenoic acid based compound - Google Patents

Abstract

PURPOSE:The titled powder, which contains lecithin, etc., eicosapentaenoic acid based compound, etc. and cyclodextrin, is a precursor for a compound having good palatability, easily handleable, exhibits physiological activity and useful as medicines, healt supplementary foods, etc. CONSTITUTION:Powder containing at least one selected from lecithin, constituent compounds thereof and hydrogenated substances thereof, at least one selected from eicosapentaenoic acid based compounds and derivatives thereof and cyclodextrin. For example, the lecithin is dissolved in the eicosapentaenoic acid based compound under heating. In the process, the amount of the lecithin to be incorporated is preferably >=0.5wt% based on the eicosapentaenoic acid based compound. The cyclodextrin is added to the resultant oily material under stirring, and the resultant mixture is cooled to give the titled powder. The amount of the cyclodextrin to be added is preferably >=3 times that of the eicosapentaenoic acid based compound.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a stable composition containing an eicosapolyenoic acid compound.

Eicosapolyenoic acid is a fatty acid with 20 carbon atoms and 3 or more (usually 3 to 6) double bonds, and examples of this include arachidonic acid (eicosatetraenoic acid, AA ) Eicosapen citric acid (E P
A) Examples include docosahexaenoic acid (DMA).

These AA, EPA, and DHA belong to a group of substances called prostaglandin (PG), lomphoxan, and leukotriene, respectively. It is an important substance that acts as a precursor for blood clots, arteriosclerosis prevention, and anticancer effects. must be supplied from

By the way, these substances are abundant in marine products in nature, especially in popular fish called "green" such as sardines and mackerel, so eicosapolyenoic acid is extracted from these fish as sardine oil and mackerel oil. However, it is provided as pharmaceuticals, health supplements, etc., either as it is or in the form of esters such as alkyl esters and triglycerides, and amides.

However, all of these eicosapolyenoic acid compounds have many unsaturated bonds, so they are poor in stability and deteriorate in a short period of time, have a unique odor and bitter taste, and are oily. It has problems, such as being inconvenient to administer and handle, and having a bad texture.

The present invention aims to solve the above-mentioned problems all at once, and its gist consists of at least one selected from lecithin, its constituent compounds, and hydrogenated products thereof, eicosaben citric acid-based compounds, and The present invention relates to an eicosapolyenoic acid compound-containing powder containing at least one compound selected from its derivatives and cyclodextrin.

In the present invention, eicosapolyenoic acid compounds are fatty acids having 20 carbon atoms and 3 or more (usually 3 to 6) double bonds, and derivatives of the fatty acids, particularly derivatives of the carboxyl group ( For example, alkyl esters, esters such as triglycerides, amides, etc.). In addition, examples of the alkyl in the above alkyl ester include lower alkyl having 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and t-butyl, and as amides, It may also be an alkyl-substituted amide such as diethylamide.

Lecithin is a mixture of compounds [hereinafter referred to as compound (1)] represented by the general formula % (R1 and R2 each represent a fatty acid residue), and in the present invention, only lecithin, which is such a mixture, is used. However, when specific compound (1) (ie, lecithin constituent compound), and further R1 and/or R2 are unsaturated fatty acids, hydrogenated versions thereof may be used. These lecithins, their constituent compounds, and their hydrogenated products may be used alone or as a mixture of two or more of them.

Examples of lecithin constituent compounds include phosphatidylcholine, phosphatidylethanosulamine, lysophosphatidylcholine, and inositol phosphatide.

The cyclodextrin used in the present invention is α-form, β-form
It may be either a body or a single body, or a mixture thereof. Furthermore, it may be a mixture with dextrin.

The method for producing the eicosapolyenoic acid compound composition powder of the present invention is, for example, as follows.

First, lecithins are dissolved in an eicosapene citric acid compound by heating. At this time, the amount of lecithin may be small relative to the eicosapene citric acid compound, but it is preferably 0.5% by weight or more. The heating temperature is a temperature at which the eicosaben citric acid compound and lecithin are dissolved.

After adding cyclodextrin to the thus obtained oily substance while stirring, the desired powder is obtained by cooling. The amount of cyclodextrin added is usually at least the same weight as the eicosapolyenoic acid compound, preferably at least 3 times the weight.

The powder of the present invention may further contain vitamin A, vitamin E, etc., and these additives may be added at any step of producing the powder of the present invention.

The powder of the present invention obtained in this manner has significantly reduced characteristic bad odor and bitterness, and has excellent stability as is clear from the results described in the experimental examples below. It has a pleasant texture and is convenient to handle.

The powder of the present invention can be made into the form of tablets, capsules, or granules either as it is or by adding powders such as vitamin C and calcium preparations as desired.

Example I 2 g of soybean lecithin was added to 2.5 g of EPA oil (containing 25% EPA liglyceride and 13% DHA triglyceride), dissolved by heating at 50°C, and while stirring, β-
Add 15 g of cyclodextrin and stir for 10 minutes. It is then cooled to obtain a pale yellow EPA oil powder.

Example 2 7.5 g of EPA oil (described above), 2 g of egg yolk lecithin, and 0.5 g of α-tocopherol are heated and dissolved at 40°C, 20 g of Toyozolin-P (manufactured by Toyo Jozo) is added, and the same procedure as in Example 1 is carried out. A pale yellow stable EPA oil powder is obtained.

Example 3 2.5 g of EPA ethyl ester (70% purity).

High purity lecithin (lecithin content 95% or more, EPI-C
RON 200 (manufactured by Lukus Meyer)) 2g
By heating and melting the powder at 45° C., adding 15 g of Lindenox-P (manufactured by Sanraku Ocean) and operating in the same manner as in Example 1, a stable and free-flowing powder can be obtained.

Experimental Example 1 The powder obtained in Example 1 (Powder A) and the powder obtained by removing lecithin from the formulation of Example 1 (Powder B) were heated at 37°C for 30
When the EPA residual rate of both powders was measured after being left for days, powder A had a residual rate of 85%, and powder B had a residual rate of 22%.

As is clear from this result, the eicosapolyenoic acid compound in the powder of the present invention exists extremely stably.

Further, all of the powders obtained in Examples 1-3 had no unique odor and had almost no bitter taste.

Patent applicant Hirokichi Kamoto Masataka Procedural Amendment (Chief) 6 June 27, 1980 Commissioner of the Patent Office 1981 Patent Application No. 60062 2 Name of the invention Powder containing eicosapolyenoic acid compound 3 , Relationship to the case of the person making the amendment Patent applicant name: Hiroshi Kaimoto Hiroshi IkL (06) 227-1156 Contents of amendment in the "Detailed Description of the Invention" column of the specification (1) Pages 1 and 14 of the specification Correct the line "Eicosapolyenoic acid has 20 carbon atoms" to "Eicosapolyenoic acid compounds have 20 to 22 carbon atoms."

(2) Structural formula on page 2 of the same book (Structural formula on page 2 of the same book) " do.

(4) On page 4 of the same book, in the first line, after “20”, “~22”
join.

Claims (1)

[Claims] An eicosapolyenoic acid compound-containing powder containing at least one compound selected from lecithin, constituent compounds thereof, and hydrogenated products thereof, at least one compound selected from eicosapene citric acid compounds and derivatives thereof, and cyclodextrin.