Modified fish oil type material containing highly unsaturated fatty acid and/or esters thereof, and a composition containing said material

An improved modified fish oil type material which does not generate special fish oil offensive odor after long term preservation and does not generate offensive odor by heating, that is, superior at preservation stability and heat stability, a fish oil type composition containing said material, a method for preparation thereof, an emulsion prepared using said material and composition and foods and cosmetics containing said material, composition or emulsion.

BACKGROUND OF THE INVENTION
 1. Field of the Invention
 The present invention relates to an improved fish oil type composition
 having good preservative stability and heat resistance, which does not
 have a specific offensive fish oil odor after long term preservation and
 does not generate odor by heating. Further, the present invention relates
 to a preparation method for said fish oil type composition, an emulsion
 prepared using said composition and foods and cosmetics containing said
 composition or emulsion. The improved fish oil composition of this
 invention contains large amount of highly unsaturated fatty acid types
 such as DHA or EPA and ester thereof, and can be applied to foods,
 cosmetics and other uses because of said non odor feature of long term,
 good preservative stability and heat resistance.
 2. Description of Prior Art
 Specific kinds of highly unsaturated fatty acid and esters thereof
 contained in fish oil are known to be useful from the medical and dietetic
 view points. For example, since eicosapentaenoic acid (hereinafter,
 shortened to EPA) and its esters have effects to reduce the content of
 cholesterol in blood and to control thrombus, it is effective for the
 prevention and the medical treatment of cardiac infarction, cerebral
 infarction and arteriosclerosis. And docosahexaenoic acid (hereinafter,
 shortened to DHA) and its ester are known to have excellent effects for
 the improvement of learning function, antitumor effect, anti-allergy
 effect and improvement of eye sight. Further, both EPA and DHA have a good
 effect against atopic dermatitis. Therefore, highly unsaturated fatty acid
 and its ester are being developed to be applied to the use of foods,
 healthy foods, cosmetics and drugs, and several kinds of them are already
 developed and on the market as healthy foods and drugs.
 However, the unsaturated bonds of highly unsaturated fatty acid and its
 ester can easily be decomposed and has a defect to generate specific
 offensive odor. To prevent this decomposition, the method to add an anti
 oxidation agent or a deodorant such as natural tocopherol, extract from
 tea and ascorbic acid are proposed, but these methods are not sufficient
 to obtain a good result. Further, the method to mix DHA with large amount
 of starch so as to wrap DHA in starch powder and to make it odorless is
 also provided. However, when the product obtained by said method is used,
 not only large amount of starch used for the wrapping of DHA gives bad
 effects to the taste of foods, but also the offensive odor based on DHA is
 not prevented, therefore, the possible amount of it to be used is
 restricted.
 Concerning the above mentioned situation, the inventors of this invention
 have already found that the bread manufactured using starting material to
 which the suspension composed by DHA based fish oil and vinegar or citrus
 fruits juice does not generate offensive odor of fish oil and had already
 disclosed this art in Japanese Patent Laid open publication 7-274806 and
 Japanese Patent Laid open publication 7-270807. However, the suspension
 composed by DHA based fish oil (and vinegar or citrus fruits juice is
 odorless at the preparation of the suspension and can be effectively used
 at the production of bread. But, when the suspension is left for long
 term, the offensive odor is regenerated. That is, it is necessary to
 improve the preservative stability of it.
 The inventors of this invention have conduced further intensive study to
 obtain a fish oil or a highly unsaturated fatty acid or an ester of it
 derived from fish oil which has good preservative stability and can
 maintain an odorless state effective for long term preservation.
 Consequently, the inventors of this invention have accomplished the
 following technique. That is, to fish oil or to a highly unsaturated fatty
 acid or an ester of it derived from fish oil, there is added at least one
 substance selected from the group composed by vinegar or citrus fruits
 juice and stirred, then the mixture (suspension) is settled so as to
 separate to oil phase and water phase. After removing of water phase, the
 oil phase is recovered as the modified fish oil. The obtained modified
 fish oil containing highly unsaturated fatty acid such as DHA or EPA
 and/or its ester, does not have an offensive odor in initial stage and
 does not generate offensive odor even after long term preservation.
 The inventors of this invention have conducted further intensive study and
 have found that by the addition of vegetable oil to said modified fish oil
 type material, the initial odorless state can be maintained during long
 term preservation, namely becomes to have a good preservation stability
 and an offensive odor does not generate even if it is heated. Further the
 inventors have also found that the clearness of the modified fish oil can
 be further improved by adding at least one substance selected from the
 group composed by collagen, starch and agar--agar. At the preparation of
 foods and cosmetics containing fish oil or highly unsaturated fatty acid
 derived from the fish oil such as DHA or EPA and/or its ester, the
 possibility for the heat treatment during the preparation procedure is so
 many. Therefore, said excellent feature that the addition of vegetable oil
 to the modified fish oil prevents the generation of offensive odor and
 maintains an odorless state when it is heated, is very effective from the
 view point of the practical use of fish oil or highly unsaturated fatty
 acid derived from the fish oil and/or its ester.
 SUMMARY OF THE INVENTION
 The main object of this invention is to provide a modified fish oil
 containing highly unsaturated fatty acid and/or its ester such as DHA or
 EPA which does not have an offensive odor and maintains an odorless state
 after preserved for long term (hereinafter shortened to "modified fish oil
 type material"). And the 2nd object of this invention is to provide a
 composition containing said modified fish oil type material (hereinafter,
 shortened to "modified fish oil composition"). The 3rd object of this
 invention is to provide an emulsion containing said modified fish oil type
 material or said composition. The 4th object of this invention is to
 provide foods containing said modified fish oil type material or said
 composition. The 5th object of this invention is to provide cosmetics
 containing said modified fish oil type material or said composition. And
 the 6th object of this invention is to provide medicines containing said
 modified fish oil type material or said composition.
 These objects can be accomplished by adding and mixing at least one
 substance selected from a group composed by vinegar and juice of citrus
 fruits to a fish oil material composed by at least one substance selected
 from a group composed by fish oil, highly unsaturated fatty acid derived
 from fish oil and its ester, and removing water phase after settling.
 Hereinafter, said obtained products can be shortened to "modified fish oil
 type material". And to the obtained modified fish oil type materials,
 vegetable oil, and at least one substance selected from collagen, starch
 and agar--agar can be added. These compounds can be called as "modified
 fish oil composition". Further, these modified fish oil type material and
 modified fish oil composition can be added to foods, cosmetics and
 medicines as an emulsifier.
 DETAILED DESCRIPTION OF THE INVENTION
 Details of the present invention is illustrated as follows.
 As the starting material to obtain a modified fish oil type material which
 can be used for the modified fish oil type material of this invention,
 fish oil, highly unsaturated fatty acid derived from fish oil or its ester
 can be mentioned. In the present invention, the term of "fish oil"
 indicates oil and fat extracted from animals living in water (namely, fish
 oil in a broad sense) and fish oil extracted from fish (fish oil in a
 narrow sense), sea animals oil and cod-liver oil are included. All type of
 said fish oil (fish oil in broad sense) contains EPA, DHA and other types
 of highly unsaturated fatty acid and/or their esters. And the term of
 "highly unsaturated fatty acid derived from fish oil" indicates fatty acid
 having 2 or more unsaturated bonds obtained by refining and separating of
 said fish oil in broad sense, and as the concrete example, EPA or DHA can
 be mentioned, however the invention is, not limited to them. Further, the
 term of "esters of highly unsaturated fatty acid" indicates the esters of
 said highly unsaturated fatty acid and glycerin (mono, di and/or tri
 glyceride), and esters of said highly unsaturated fatty acid and lower
 alcohol (for instance, methyl ester, ethyl ester and so on).
 In the present invention, as the material of fish oil, following kinds of
 compound can be used. That is, crude fish oil, lower refined fish oil,
 highly refined fish oil, mixture of highly unsaturated fatty acid and/or
 its ester separating highly unsaturated fatty acid and/or esters contained
 in fish oil from fish oil as a mixture of plural types of highly
 unsaturated fatty acid and/or its ester and single substance of specific
 highly unsaturated fatty acid and/or its ester obtained from fish oil can
 be mentioned. In general, as the fish oil material, the fish oil extracted
 from sardine, mackerel, codfish and tuna (fish oil in a narrow sense),
 lower and highly refined oil of it, highly unsaturated fatty acid obtained
 from said fish oil and its ester are preferably used from the view of
 easily procuring and lower price. Further, in the present invention, the
 product in which more than 10 weight % of DHA and/or EPA are contained is
 desirably used from the view point of health promotion, and illness
 prevention and treatment. In this invention, the fish oil material on the
 market or the newly prepared fish oil materials developed for this
 invention can be preferably used.
 Further, in the present invention, the modified fish oil type materials can
 be prepared by adding vinegar and/or juice of citrus fruits to the said
 fish oil type materials and treating. That is, when vinegar and/or a juice
 of citrus fruits is added to a fish oil material and stirred, then the
 obtained mixture (suspension) is settled, the mixture separates to upper
 oil layer and lower water layer. The lower water layer is removed, and the
 upper oil layer is recovered as the modified fish oil type material.
 As the vinegar to be used in this case, both a brewing vinegar or a
 synthetic vinegar can be used. As the example of a brewing vinegar, a
 grain vinegar such as rice vinegar, raw rice vinegar and malt vinegar,
 apple vinegar and grape vinegar can be mentioned. And as the example of a
 synthetic vinegar, the diluted acetic acid by water and amino acid and
 saccharides are added, a vinegar to which synthetic acetic acid is added
 can be mentioned. As the example of a juice of citrus fruits, juice from
 lime, lemon, zamboa, bitter orange, grape fruit, summer orange, citron
 orange, sudachi orange and the concentrated juice of them can be
 mentioned.
 In the present invention, said brewing vinegar, synthetic vinegar and juice
 of citrus fruits can be used alone or can be used in combination. In the
 case of combination use, a combination of more than two kinds of brewing
 vinegar, a combination of more than two kinds of synthetic vinegar, a
 combination of one or more kinds of brewing vinegar with one or more kinds
 of synthetic vinegar, a combination of one or more kinds of brewing
 vinegar or synthetic vinegar with one or more kinds of citrus fruits
 juice, or a combination of one or more kinds of citrus fruits juice can be
 used. Especially, vinegar from fruits such as apple vinegar is preferably
 used. The reason is not clear, however, in the apple vinegar, organic
 acids such as malic acid, citric acid, oxalic acid and tartalic acid are
 contained with acetic acid, and they deem to generate synergism effect.
 The desirable proportion of vinegar and/or citrus fruits juice to be added
 to the fish oil type material is 2-70 weight parts (total weight, when
 more than two kinds of vinegar and/or citrus fruits juice are used) to 100
 parts of fish oil type material, more desirably 10-65 weight parts. When
 the amount of added vinegar and/or citrus fruits juice is smaller than 2
 weight parts, it is difficult to remove the offensive odor of fish oil
 type material, and when more than 70 weight parts, acid flavor becomes too
 strong and deteriorates the flavor and taste of the modified fish oil type
 material.
 As the mixing and stirring method after vinegar and/or citrus fruits juice
 is added to the fish oil type material, a conventional mixing stirring
 apparatus can be used, and as the concrete example, a propeller mixer, a
 turbine mixer and a homogeneous-mixer can be used. From the view point of
 preventing the quality change and the solidification of the fish oil type
 material, the desirable temperature during the mixing and stirring
 procedure is generally 10-25.degree. C. Further, the mixing and stirring
 can be continued until the homogeneous suspension can be obtained, and the
 time for mixing and stirring is not restricted, however, when above
 mentioned conventional mixing stirring apparatuses are used, preferable
 mixing and stirring time is generally 1-30 minutes. And when the mixing
 and stirring procedure after vinegar and/or citrus fruits juice is added
 to the fish oil type material is carried out under the inert gas
 atmosphere such as nitrogen gas, the oxidation of highly unsaturated fatty
 acid and/or ester thereof contained in fish oil type material can be more
 effectively controlled, and the modified fish oil type which is more
 superior at remaining odorless can be obtained.
 After generating the suspension by above mentioned mixing and stirring
 treatment, the water phase is removed. The suspension obtained by the
 conventional stirring procedure is settled so as to separate to the oil
 phase and to the water phase, and the upper oil phase is separated from
 the lower water layer, then the modified fish oil type material is
 recovered. The obtained modified fish oil type material is characterized
 as an odorless product which does not have an offensive odor specialized
 to fish oil, and the odorless state can be maintained after the long term
 preservation, that is, has a good preservative stability. By adding
 adequate amount of water, emulsion can be obtained. The fused oxygen in
 the water to be added at the emulsification is desirably removed
 previously by replacing with inert gas such as nitrogen. The desirable
 amount of water is 100-300% to the amount of treated oil (modified fish
 oil material). The obtained emulsion can be added to foods or cosmetics
 and the foods or the cosmetics in which DHA and EPA are contained can be
 obtained. The food in which 100-300 mg of DHA and EPA are contained can be
 obtained without spoiling the original flavor and taste of the food.
 Similarly, the colorless and odorless cosmetics can be obtained by adding
 said emulsion to a cosmetic such as milky lotion, hand cream, skin cream,
 makeup lotion, jelly or pack.
 Further, in the present invention, vegetable oil is added to the obtained
 modified fish oil material and the modified fish oil composition which has
 good preservative stability maintaining odorless state after the long term
 preservation and has a good heat stability not generating offensive odor
 by heating is prepared. As the vegetable oil to be added to the modified
 fish oil material, any kinds of vegetable oil can be used as long as these
 are safe to the human health. As the concrete example, grape oil, rice
 oil, wheat germ oil, olive oil, perilla oil, safflower oil, soy bean oil,
 sesame oil, corn oil, cotton seed oil, salad oil and the hydrogenated oil
 of them can be mentioned. Among them, grape oil, rice oil, wheat germ oil,
 olive oil and/or perilla oil can be preferably used from the view point of
 preservative stability and flavor.
 The desirable amount of vegetable oil to be added is 10-120 weight parts to
 100 weight parts of the modified fish oil type material, and more
 desirably 30-100 weight parts. When the amount of vegetable oil to be
 added is smaller than 10 weight parts to 100 weight parts of the modified
 fish oil type material, the heat stability of the modified fish oil type
 material is not improved sufficiently. In the meanwhile, when it is more
 than 120 weight parts, the proportion of the modified fish oil material in
 the composition is decreased, consequently, the proportion of the
 effective highly unsaturated fatty acid and/or ester of it such as DHA or
 EPA in the modified fish oil composition is relatively low, and the effect
 of DHA or EPA in foods or cosmetics becomes difficult to be displayed
 fully.
 Regarding to the method to add the vegetable oil to the modified fish oil
 type material, there is no limitation, and any kinds of methods which are
 possible to mix the vegetable oil homogeneously into the modified fish oil
 type material can be Let: used. Generally, it is possible to mix them
 using said conventional mixing and stirring apparatus, at the temperature
 lower than 30.degree. C. and higher than the solidifying temperature of
 the modified fish oil type material.
 And, in the present invention, at least one kind of additives selected from
 the group composed by collagen, starch and agar--agar can be added to the
 modified fish oil type material with vegetable oil at need. When at least
 one kind of additives selected from the group composed by collagen, starch
 and agar--agar is added to the modified fish oil type material, the
 modified fish oil composition which is superior in clearness can be
 obtained. At the addition of at least one additives selected from
 collagen, starch and agar--agar, the amount of addition (total amount,
 when two kinds of additives are used) is desirably to be 0.05-1 weight
 parts to 100 weight parts of the modified fish oil type material, and more
 desirably 0.05-0.2 weight parts. When the amount of addition of at least
 one additive selected from collagen, starch and agar--agar is bigger than
 one weight parts, the sedimentation is easily generated.
 As a collagen, the collagen obtained from the binding tissue of animal,
 cartilage and tendon, or the soluble type of gelatin of them obtained by
 heating them in water can be used. Especially, a water soluble gelatin is
 preferably used from the view point of possibility of homogeneously mixing
 into the modified fish oil type material, easily handling and reducing
 cost. As a starch, potato starch, wheat starch and corn starch can be
 used. Especially, a granular type of starch is desirably used, from the
 view point of easily handling and clearness. Further, as an agar--agar,
 the product which is extracted from cell wall component of red algae,
 dehydrated and dried up is used. Solid type agar--agar, square pole type
 agar--agar, string type agar--agar, granular type agar--agar and powder
 type agar--agar can be used. However, from the view point of easily
 handling and clearness, the powder type agar--agar is preferably used.
 The timing to add at least one additive selected from collagen, starch and
 agar--agar to the modified fish oil type material is not restricted. They
 can be added before, together with or after the addition of the vegetable
 oil. Especially, at least one additive selected from collagen, starch and
 agar--agar is desirably added before adding vegetable oil so as to obtain
 the modified fish oil composition which has better clearness.
 The modified fish oil material and/or the modified fish oil composition of
 this invention obtained by above mentioned method can be added to many
 kinds of foods, cosmetic and others, or can be used alone as a medicine or
 mixed with other components. And said products to which modified fish oil
 material and/or the modified fish oil composition of this invention have
 effects for reducing of the content of cholesterol in blood, prevention
 and medical treatment of cardiac infarction, cerebral infarction and
 arteriosclerosis, improvement of learning function, antitumor,
 anti-allergy and improvement of eye sight according to the kind of highly
 unsaturated fatty acid and/or ester of it contained in the modified fish
 oil material and/or modified fish oil type material composition.
 When the modified fish oil material and/or modified fish oil composition of
 this invention are added to foods, there is no limitation to the kind of
 food. As the concrete example, bakery products such as bread, steamed
 rice, noodles, soy bean processed foods such as bean curd, animal meat
 processed foods such as sausage and ham, confectioneries such as cake,
 cookie, bean-jam bun, rice cracker, ice-cream, pudding, bean-jam sweet
 jelly and candy, dairy products such as butter and yogurt, seasonings such
 as mayonnaise, dressing, soy bean sauce, soy bean paste and sauce,
 saccharoids such as glucose and liquid oligosaccharide, drinks such as
 fruits beverage, soy bean milk and vegetable juice and an arum root paste
 can be mentioned.
 In a case of fish oil and derived highly unsaturated fatty acid and/or its
 ester, the upper limit of blending proportion of DHA or EPA and/or its
 ester to 600 g weight of bread is 20-30 mg because of it's offensive odor
 based on fish oil. However, in the case of the modified fish oil material
 and/or modified fish oil composition of this invention 100-300 mg of DHA
 or EPA and/or its ester can be blended to 600 g weight of bread and other
 foods which can fully display the excellent effect based on highly
 unsaturated fatty acid or its ester such as DHA or EPA.
 Further, the modified fish oil material and/or modified fish oil
 composition (modified fish oil composition) of this invention obtained as
 above can be an emulsion with water using adequate emulsifier by
 conventional well known method, and the obtained emulsion can be used for
 the production of above mentioned foods, for the production of cosmetics
 such as milky lotion, hand cream, skin cream, massage cream, makeup lotion
 or pack or for any other applications

EXAMPLES
 The present invention is illustrated more readily with reference to the
 following Examples, however, not intended to be construed to limit the
 scope of the invention.
 Example 1
 (Preparation of Modified Fish Oil Type Material)
 10 weight parts of apple vinegar is added to 100 weight parts of fish oil
 containing 25 weight parts of DHA and mixed. The obtained suspension is
 settled over 24 hours and lower water layer is removed, and the odorless
 modified fish oil type material is obtained.
 Example 2
 Fused oxygen gas in water is previously removed by replacing with nitrogen
 gas, and 100 weight parts of said treated water is added to 100 weight
 parts of odorless modified fish oil type material obtained in Example 1,
 mixed in mixer, emulsified, then the emulsion containing odorless DHA is
 obtained.
 Example 3
 65 weight parts of apple vinegar is added to 100 weight parts of fish oil
 containing 45 weight % of DHA. The obtained suspension is settled over 24
 hours and lower water layer is removed, and the odorless modified fish oil
 type material is obtained.
 Example 4
 Fused oxygen gas in water is previously removed by replacing with nitrogen
 gas, and 150 weight parts of said treated water is added to 100 weight
 parts of odorless modified fish oil type material obtained in Example 3,
 mixed in a mixer, emulsified, then the emulsion containing odorless DHA is
 obtained.
 Example 5
 30 weight parts of apple vinegar is added to 100 weight parts of fish oil
 containing 45 weight % of DHA ethyl ester. The obtained suspension is
 settled over 24 hours and lower water layer is removed, and the odorless
 modified fish oil type material is obtained.
 Example 6
 Fused oxygen gas in water is previously removed by replacing with nitrogen
 gas, and 200 weight parts of said treated water is added to 100 weight
 parts of odorless modified fish oil type material in Example 5, mixed in a
 mixer, emulsified, then the emulsion containing odorless DHA ethyl ester
 is obtained.
 Example 7
 Same procedures as Example 1, 3, 5 are carried out except using lemon juice
 instead of apple vinegar, and three kinds of odorless modified fish oil
 type material are obtained.
 Example 8
 Fused oxygen gas in water is previously removed by replacing with nitrogen
 gas, and 100, 200 and 300 weight parts of said treated water are added to
 100 weight parts of odorless modified fish oil type materal obtained in
 Example 7, mixed in a mixer, emulsified, then the three kinds of emulsion
 containing odorless DHA are obtained.
 Example 9
 Same procedures as Example 1 are carried out except using the fish oil
 containing 20 wt % of EPA instead of the fish oil containing 25 wt % of
 DHA, and the odorless modified fish oil type material is obtained.
 Example 10
 Fused oxygen gas in water is previously removed by replacing with nitrogen
 gas, and 120 weight parts of said treated water is added to 100 weight
 parts of odorless modified fish oil type material obtained in Example 9,
 mixed in a mixer, emulsified, then the emulsion containing odorless EPA is
 obtained.
 Example 11
 Same procedures as Example 3 are carried out except using the fish oil
 containing 55 wt % of EPA instead of the fish oil containing 45 wt % of
 DHA, and the odorless modified fish oil type material is obtained.
 Example 12
 Fused oxygen gas in water is previously removed by replacing with nitrogen
 gas, and 220 weight parts of said treated water is added to 100 weight
 parts of odorless modified fish oil type material obtained in Example 11,
 mixed in mixer, emulsified, then the emulsion containing odorless EPA is
 obtained.
 Example 13
 Same procedures as Example 5 are carried out except using fish oil
 containing 90 wt % of EPA ethyl ester instead of the fish oil containing
 75 wt % of DHA ethyl ester, and the odorless modified fish oil type
 material is obtained.
 Example 14
 Fused oxygen gas in water is previously removed by replacing with nitrogen
 gas, and 300 weight parts of said treated water is added to 100 weight
 parts of odorless modified fish oil type material obtained in Example 13,
 mixed in a mixer, emulsified, then the emulsion containing odorless EPA is
 obtained.
 Example 15
 Same procedures as Example 9, 11, 13 are carried out except using lemon
 juice instead of apple vinegar, and 3 kinds of oil containing the odorless
 modified fish oil type material are obtained.
 Example 16
 Fused oxygen gas in water is previously removed by replacing with nitrogen
 gas, and 100, 150 and 300 weight parts of said treated water are added to
 100 weight parts of the odorless modified fish oil type material obtained
 in Example 15, mixed in a mixer, emulsified, then the 3 kinds of emulsion
 containing odorless EPA are obtained.
 Comparative Example 1
 2, 10 and 50 weight parts of apple vinegar are added to 100 weight parts of
 fish oil containing 25 wt % of DHA and three samples of suspension are
 prepared. The generation of special offensive odor of fish oil by aging of
 these three samples of suspension are investigated in comparison with
 samples of odorless modified fish oil type material obtained in Example 1,
 3, 5, 9, 11, 13 and 15 and samples of emulsion obtained in Example 2, 4,
 6, 10, 12, 14 and 16 of this invention. Immediately after the preparation,
 these samples of suspension, odorless modified fish oil type materials and
 emulsions of this invention are packed in sealed container and preserved
 in room temperature. Each samples are investigated after 2 days, 1 week
 and 1 month whether special offensive odor is generate. Referring to said
 samples of suspension, they generate special offensive odor of fish after
 2 days, on the contrary the odorless modified fish oil type materials and
 emulsions of this invention maintained odorless state after 1 month.
 Example 17
 (Preparation of Modified Fish Oil Composition)
 (1) 10 weight parts of rice vinegar is added to 100 weight parts of fish
 oil containing 27 wt % of DHA. Maintaining the temperature of the mixture
 at 10.degree. C., the mixture is mixed and stirred for 5 minutes by 500
 r.p.m. using a mixer having Pfaudler type 2 wing stirrer in the nitrogen
 gas atmosphere, and the suspension is prepared.
 (2) After the suspension obtained by procedure (1) is settled for 24 hours
 in the nitrogen gas atmosphere and separated to a oil phase and an water
 phase, the lower water phase is removed. Then the upper oil phase is
 recovered, and the odorless modified fish oil type material is obtained.
 (3) 100 weight parts of wheat germ oil is added to 100 weight % of the
 modified fish oil type material obtained by (2), mixed and stirred well in
 the nitrogen gas atmosphere and the modified fish oil composition
 containing DHA is prepared.
 (4) Three small portions are sampled from the modified fish oil composition
 obtained by above (3) procedure, and heated for 10 minutes at the
 temperature of 60.degree. C., 70.degree. C. and 80.degree. C. Whether
 there is offensive odor or not is investigated on each samples by five
 panelists according to the evaluation standard shown in Table 1. The
 results by five panelists are averaged and summarized in Table 2.
 Example 18
 (Preparation of Modified Fish Oil Composition)
 (1) 5 weight parts of apple vinegar is added to 100 weight parts of fish
 oil containing 45 wt % of DHA. After the suspension is prepared by same
 mixing and stirring procedure as to (1) of Example 17, the obtained
 suspension is settled for 24 hours at room temperature and separated to an
 oil phase and an water phase. The lower water phase is removed off and
 then the upper oil phase is recovered, thus the odorless modified fish oil
 type material is obtained.
 (2) 30 weight parts of brewing olive oil is added to 100 parts of modified
 fish oil type material obtained by procedure (1), and mixed and stirred
 well in the nitrogen gas atmosphere and the modified fish oil composition
 containing DHA is prepared.
 (3) Three small portions are sampled from the modified fish oil composition
 obtained by above (2) procedure, and heated according to the procedure (4)
 of Example 17. Whether there is offensive odor or not is investigated on
 each samples by five panelists according to the following evaluation
 standard shown in Table 1. The results by five panelists are averaged and
 summarized in Table 2.
 Example 19
 (Preparation of Modified Fish Oil Composition)
 (1) 10 weight parts of apple vinegar is added to 100 weight parts of fish
 oil containing 45 wt % of DHA. After the suspension is prepared by same
 mixing and stirring procedure as to (1) of Example 17, the obtained
 suspension is settled for 24 hours at room temperature and separated to a
 oil phase and an water phase. The lower water phase is removed off and
 then the upper oil phase is recovered, thus the odorless modified fish oil
 type material is obtained.
 (2) 0.05 weight parts of water soluble gelatin is added to 100 parts of
 modified fish oil type material obtained by procedure (1) and settled for
 24 hours. The fish oil which has good transparency is obtained.
 (3) 100 weight parts of brewing grape oil is added to 100 parts of modified
 fish oil type material obtained by procedure (2), mixed and stirred well
 in the nitrogen gas atmosphere and the modified fish oil composition
 containing DHA is prepared.
 (4) Three small portions are sampled from the modified fish oil composition
 obtained by above procedure (3), and heated according to the procedure (4)
 of Example 17. Whether there is offensive odor or not is investigated on
 each samples by five panelists according to the following evaluation
 standard shown in Table 1. The results by five panelists are averaged and
 summarized in Table 2.
 Example 20
 (Preparation of Modified Fish Oil Composition)
 (1) 20 weight parts of apple vinegar is added to 100 weight parts of fish
 oil containing 70 wt % of DHA ethyl ester obtained by the ester transfer
 reaction of fish oil. After the suspension is prepared by same mixing and
 stirring procedure as to (1) of Example 17, the obtained suspension is
 settled for 24 hours at room temperature and separated to an oil phase a
 an water phase. The lower water phase is removed off and then the upper
 oil phase is recovered, thus the odorless modified fish oil type material
 is obtained.
 (2) 100 weight parts of rice oil is added to 100 parts of modified fish oil
 type material obtained by procedure (1), and mixed and stirred well in the
 nitrogen gas atmosphere and the modified fish oil composition containing
 DHA is prepared.
 (3) Three small portions are sampled from the modified fish oil composition
 obtained by above procedure (2), and heated according to the procedure (4)
 of Example 17. Whether there is offensive odor or not is investigated on
 each samples by five panelists according to the following evaluation
 standard shown in Table 1. The results by five panelists are averaged and
 summarized in Table 2.
 Example 21
 (Preparation of Modified Fish Oil Composition)
 (1) The odorless modified fish oil type material is prepared by same
 procedure to Example 17 except using fish oil containing 25 wt % of EPA
 instead of fish oil containing 27 wt % of DHA, then the modified fish oil
 composition containing wheat germ oil is prepared by same procedure to
 Example 17.
 (2) Three small portions are sampled from the modified fish oil composition
 obtained by above procedure (1), and heated according to the procedure (4)
 of Example 17. Whether there is offensive odor or not is investigated on
 each samples by five panelists according to the following evaluation
 standard shown in Table 1. The results by five panelists are averaged and
 summarized in Table 2.
 Example 22
 (Preparation of Modified Fish Oil Composition)
 (1) The odorless modified fish oil type material is prepared by same
 procedure to Example 18 except using fish oil containing 55 wt % of EPA
 instead of fish oil containing 45 wt % of DHA, then the modified fish oil
 composition containing olive oil is prepared by same procedure to Example
 18.
 (2) Three small portions are sampled from the modified fish oil composition
 obtained by above procedure (1), and heated according to the procedure (4)
 of Example 17. Whether there is offensive odor or not is investigated on
 each samples by five panelists according to the following evaluation
 standard shown in Table 1. The results by five panelists are averaged and
 summarized in Table 2.
 Example 23
 (Preparation of Modified Fish Oil Composition)
 (1) The odorless modified fish oil type material is prepared by same
 procedure as Example 19 except using fish oil containing 45 wt % of EPA
 instead of fish oil containing 45 wt % of DHA, then the modified fish oil
 composition containing grape oil is prepared by same procedure to Example
 19.
 (2) Three small portions are sampled from the modified fish oil composition
 obtained by above procedure (1), and heated according to the procedure (4)
 of Example 17. Whether there is offensive odor or not is investigated on
 each samples by five panelists according to the following evaluation
 standard shown in Table 1. The results by five panelists are averaged and
 summarized in Table 2.
 Example 24
 (Preparation of Modified Fish Oil Composition)
 (1) The odorless modified fish oil type material is prepared by same
 procedure as Example 20 except using fish oil containing 90 wt % of EPA
 ethyl ester instead of fish oil containing 70 wt % of DHA ethyl ester,
 then the modified fish oil composition containing rice oil is prepared by
 same procedure to Example 20.
 (2) Three small portions are sampled from the modified fish oil composition
 obtained by above procedure (1), and heated according to the procedure (4)
 of Example 17. Whether there is offensive odor or not is investigated on
 each samples by five panelists according to the following evaluation
 standard shown in Table 1. The results by five panelists are averaged and
 summarized in Table 2.
 Example 25
 (Preparation of Modified Fish Oil Composition)
 (1) 10 weight parts of lemon juice is added to 100 weight parts of fish oil
 containing 27 wt % of DHA. After the suspension is prepared by same mixing
 and stirring procedure as to (1) of Example 17, the obtained suspension is
 settled for 24 hours at room temperature and separated to a oil phase and
 an water phase. The lower water phase is removed off and then the upper
 oil phase is recovered, thus the odorless modified fish oil type material
 is obtained.
 (2) 30 weight parts of olive oil is added to 100 parts of modified fish oil
 type material obtained by procedure (1), and mixed and stirred well in the
 nitrogen gas atmosphere and the modified fish oil composition containing
 DHA is prepared.
 (3) Three small portions are sampled from the modified fish oil composition
 obtained by above procedure (2), and heated according to the procedure (4)
 of Example 17. Whether there is offensive odor or not is investigated on
 each samples by five panelists according to the following evaluation
 standard shown in Table 1. The results by five panelists are averaged and
 summarized in Table 2.
 Comparative Example 2-4
 (Preparation of Fish Oil Composition)
 (1) To 100 weight parts of fish oil containing 27 wt % of DHA, 5 weight
 parts (Comparative Example 2), 10 weight parts (Comparative Example 3) and
 20 weight parts (Comparative Example 4) of apple vinegar is added. After
 three kinds of suspension are prepared by same mixing and stirring
 procedure as to (1) of Example 17, 100 weight parts of grape oil is added
 to said three kinds of suspension and are mixed and stirred well at
 25.degree. C. in the nitrogen gas atmosphere. Thus three samples of
 suspension are prepared.
 (2) Three samples of suspension prepared by above mentioned procedure (1)
 are heated for 10 minutes at the temperature of 60.degree. C., 70.degree.
 C. and 80.degree. C. Whether there is a generation of offensive odor is
 investigated by five panelists according to the evaluation standard shown
 in Table 1. The results by five panelists are averaged and summarized in
 Table 2.
 TABLE 1
 Odor evaluation standard for modified fish oil composition
 Point evaluation
 4 no offensive odor of fish oil, very good
 3 slightly have offensive odor but not be anxious, good
 2 have offensive odor of fish oil, not good
 1 have strong offensive odor of fish oil, bad
 TABLE 2
 modified fish oil
 contents composition
 Example of modified fish offensive odor
 and Com- fish oil oil preparation vegetable by heating
 parative (cont. component oil.sup.2 (10 minutes)
 Example in fish and proportion weight temp.(.degree. C.)
 number oil.sup.1) (weight parts) parts.sup.3 60 70 80
 Ex. 17 DHA 27% rice vinegar 10/ A 100 4 4 4
 fish oil 100
 Ex. 18 DHA 45%.sup.4 apple vinegar 5/ B 30 4 4 3.6
 fish oil 100
 Ex. 19 DHA 45% apple vinegar 10/ C 100 4 4 3.8
 fish oil 100
 Ex. 20 DHA ester apple vinegar 20/ D 100 4 3.8 3.8
 70% fish oil 100
 Ex. 21 EPA 25% rice vinegar 10/ A 100 4 4 4
 fish oil 100
 Ex. 22 EPA 55%.sup.4 apple vinegar 5/ B 30 4 3.8 3.8
 fish oil 100
 Ex. 23 EPA 45% apple vinegar 10/ C 100 4 4 3.8
 fish oil 100
 Ex. 24 EPA ester apple vinegar 20/ D 100 4 3.8 3.6
 90% fish oil 100
 Ex. 25 DHA 27% lemon juice 10/ D 30 4 4 4
 fish oil 100
 Co. Ex. 2 DHA 27% apple vinegar 5/ C 100.sup.5 1.6 1.2 1.2
 fish oil 100.sup.5
 Co. Ex. 3 DHA 27% apple vinegar 10/ C 100.sup.5 2 1.2 l.2
 fish oil 100.sup.5
 Co. Ex. 4 DHA 27% apple vinegar 20/ C 100.sup.5 2 1.2 1
 fish oil 100.sup.5
 Remarks
 .sup.1 contents of DHA or EPA in fish oil (wt %)
 .sup.2 kinds of vegetable oil
 A: wheat germ oil, B: olive oil, C: grape oil, D: rice oil
 .sup.3 weight parts of vegetable oil to 100 parts of modified fish oil
 .sup.4 water soluble gelatin is added to modified fish oil before addition
 of vegetable oil
 .sup.5 grape oil is directly added to the suspension of fish oil and apple
 vinegar
 From the results of above mentioned Table 2, it is clearly understood that
 the modified fish oil compositions of Example 17-25 of this invention have
 good heat stability because they do not generate the special offensive
 odor of fish oil even if they are heated. Said compositions of Example
 17-25 are prepared by following procedure. That is, vinegar and/or juice
 of citrus fruits are added to the fish oil containing highly unsaturated
 fatty acid and/or esters thereof such as DHA or EPA and mixed, stirred and
 settled, then upper oil layer is recovered as the modified fish oil type
 material and vegetable oil is added. Further, from the results of above
 mentioned Example 18 and 22, when collagen is added with vegetable oil,
 since the transparency is improved, it is understood that the quality of
 the modified fish oil composition is furthermore improved.
 On the contrary, in the cases of Comparative Example 2-4, it is obvious
 that, even if vinegar and vegetable oil are added to fish oil containing
 highly unsaturated fatty acid and/or esters thereof such as DHA or EPA,
 when vegetable oil is added directly to a suspension obtained by adding
 vinegar to fish oil, the fish oil composition having good heat stability
 can not be obtained, and it generates a special offensive fish oil odor.
 The modified fish oil type materials and emulsions containing odorless DHA
 or EPA which are prepared according to the method of said Example 1-16 are
 added to many kinds of foods and cosmetics, and the flavor and taste of
 obtained foods, smell and color tone of cosmetics are investigated by
 comparison experiments.
 Example 26
 Manufacturing of Bread

wheat powder 100.0 parts
 yeast 3.0 parts
 powdered milk 3.0 parts
 sugar 5.0 parts
 water 70.0 parts
 yeast food 0.1 parts
 salt 2.0 parts
 margarine 7.0 parts
 To the bread base of above mentioned recipe, the modified fish oil type
 material containing odorless DHA obtained by Example 1 is blended. After
 kneaded, take 60 minutes floor time at 25.degree. C., 30 minutes of bench
 time at room temperature, pour into a mold and maintain it in 35.degree.
 C. temperature and 90% humidity for one hour for fermentation. The
 prepared bread base is baked in an oven and a bread is obtained. The
 odorless modified fish oil type materials obtained by Examples 3, 5, 7, 9,
 11, 13, 15 or emulsions obtained by Examples 2, 4, 6, 8, 10, 12, 14, 16
 are added to the bread base and baked a bread. Each bread contains 250 mg
 of DHA or EPA per 400 g of bread.
 The bread to which odorless modified fish oil type material or emulsion is
 added, has not special offensive fish oil odor, and the flavor and taste
 of the bread is not different from that of ordinary bread.
 Example 27
 Manufacturing of Bean Curd
 After soy beans are boiled, separated to soybean milk (10-12%) and
 bean-curd refuse. 3 g of bittern per 1 liter of soybean milk and the
 modified fish oil type material containing odorless DHA obtained in
 Example 1 and stirred in a stainless steel bowl. After settled for 20
 minutes, transferred to a mold box and pressed by a hydraulic power jack
 and a bean curd is prepared. The odorless modified fish oil type materials
 obtained by Examples 3, 5, 7, 9, 11, 13, 15 or emulsions obtained by
 Examples 2, 4, 6, 8, 10, 12, 14, 16 are added by same procedure and bean
 curds are prepared. Each bean curd contains 100 mg of DHA or EPA to 100 g
 of bean curd.
 The bean curd to which odorless modified fish oil type material or emulsion
 is added, has not special offensive fish oil odor, and the flavor and
 taste of the bean curd is not different from that of ordinary bean curd.
 Example 28
 Preparation of Mayonnaise
 To 15 g of egg yolk, 10 g of salt and 1 g of sugar is added and stirred
 well, then 75 g of vegetable oil is added gradually under constant
 stirring. After changed to paste state, 10 g of vinegar, the odorless
 modified fish oil type materials obtained by Examples 1, 3, 5, 7, 9, 11,
 13, 15 or emulsions obtained by Examples 2, 4, 6, 8, 10, 12, 14, 16 are
 added by adjusting viscosity and mayonnaise are prepared. Each mayonnaise
 contains 100 mg of DHA or EPA per 100 g of mayonnaise.
 The mayonnaise to which odorless modified fish oil type material or
 emulsion is added, has not special offensive fish oil odor, and the flavor
 and taste of the mayonnaise is not different from that of ordinary
 mayonnaise.
 Example 29
 Preparation of Arum Root Paste
 10 weight parts of vinegar is added to 100 parts of oil containing 25 wt %
 of DHA. Obtained white suspension is settled as to be separated to two
 layers. The lower vinegar base layer is filtrated and removed. 100 parts
 of white suspension containing DHA treated as above and 100 parts of water
 is mixed in a mixer and emulsified. In this case, it is desirable to
 replace the fused oxygen gas in water previously by nitrogen gas.
 The obtained emulsion is an odorless and stabilized emulsion. By adding
 said emulsion to an arum root paste, the arum root paste containing DHA by
 high proportion which is suited as a healthy food without spoiling the
 flavor of arum root paste.
 Example 30
 Preparation of Arum Root Paste
 10 weight parts of vinegar is added to 100 parts of oil containing 25 wt %
 of EPA. Obtained white suspension is settled as to be separated to two
 layers. The lower vinegar base layer is filtrated and removed. 100 parts
 of white suspension containing EPA treated as above and 100 parts of water
 is mixed in a mixer and emulsified. In this case, it is desirable to
 replace the fused oxygen gas in water previously by nitrogen gas.
 The obtained emulsion is an odorless and stabilized emulsion. By adding
 said emulsion to an arum root paste, the arum root paste contains EPA by
 high proportion which is suited as a healthy food without spoiling the
 flavor of arum root paste.
 Example 31
 The odorless modified fish oil type materials obtained by Examples 1, 3, 5,
 7, 9, 11, 13, 15 or emulsions obtained by Examples 2, 4, 6, 8, 10, 12, 14,
 16 are added to ice cream, yogurt, margarine and soy bean paste. 0.2
 weight parts of DHA or ethyl ester of it or EPA or ethyl ester of it are
 contained in 100 weight parts of ice cream, 100 weight parts of yogurt, 10
 weight parts of margarine and 100 weight parts of soy bean paste. The
 flavor and taste of each foods are checked, and all of these foods do not
 have a special offensive fish oil odor and are not different from the
 conventional ones.
 Example 32

liquid paraffin 45 weight parts
 stearyl alcohol 7 weight parts
 stearic acid 3 weight parts
 squarane 7 weight parts
 vaseline 13 weight parts
 propylene glycol 12 weight parts
 lanoline hydrate 3 weight parts
 10 weight % of the odorless modified fish oil type materials obtained by
 Examples 1, 3, 5, 7, 9, 11, 13, 15 or emulsions obtained by Examples 2, 4,
 6, 8, 10, 12, 14, 16 are added respectively to the mixture of above
 mentioned recipe melted at the temperature of 70.degree. C. and are
 emulsified homogeneously, cooled down and cream products are obtained.
 Color and smell are checked just after and one month after the
 preparation, and these products do not have color change and a special
 offensive fish oil odor.
 Example 33

ethyl alcohol 15 weight parts
 propylene glycol 12 weight parts
 glycerin 3 weight parts
 stearic acid 2 weight parts
 cetyl alcohol 1 weight parts
 pure water 59 weight parts
 5.0 weight % of the odorless modified fish oil type materials obtained by
 Examples 1, 3, 5, 7, 9, 11, 13, 15 or 10.0 weight % of emulsions obtained
 by Examples 2, 4, 6, 8, 10, 12, 14, 16 are added respectively to the
 mixture of above mentioned proportion, stirred, mixed and milky lotion
 products are obtained. Color and smell of these products are checked just
 after and one month after the preparation, and these products do not have
 color change and a special offensive fish oil odor.
 Example 34
 (Addition of Modified Fish Oil Composition to Sweetners)
 (1) 20 weight parts of the before heat treatment modified fish oil
 composition obtained in Example 17 and 2 weight parts of emulsifier
 (product of Mitsubishi Chemical Co., Ltd. "Sugar Ester S1170") are added
 to 78 weight parts of liquid sweetners on market, mixed for 3 minutes by
 10,000 r.p.m. in a homogeneous mixer and an artificial sweetners
 containing the modified fish oil composition is prepared.
 (2) 5 weight parts of artificial sweetners obtained in procedure (1) is
 poured into 100 weight parts of 80.degree. C. hot water and stirred, and
 whether there is a special fish oil odor or not is estimated by five
 panelists according to the evaluation standard shown in Table 1. Total
 points by five panelists is 18, therefore, a special offensive fish oil
 odor is not generated.
 Example 35-42
 (Addition of Modified Fish Oil Composition to Sweetners)
 (1) Artificial sweetners containing the modified fish oil composition are
 prepared by same procedure of Example 34, except using the before heat
 treatment modified fish oil composition obtained in Examples 18-25.
 (2) 5 weight parts of artificial sweetners obtained in procedure (1) is
 poured into 100 weight parts of 80.degree. C. hot water and stirred, and
 whether there is a special fish oil odor or not is estimated by five
 panelists according to the evaluation standard shown in Table 1. Total
 points by five panelists is 19, therefore, a special offensive fish oil
 odor is not generated.
 Example 43
 (Addition of Modified Fish Oil Composition to Milk)
 1 weight parts of the before heat treatment modified fish oil composition
 obtained in Example 17 is added to 100 weight parts of milk, mixed well,
 then heated for 30 minutes at 63.degree. C. Preserved in sealed container
 at room temperature for 7 days. After 7 days, the container is opened and
 whether there is a special fish oil odor or not is estimated by five
 panelists according to the evaluation standard shown in Table 1. Total
 points by five panelists is 20, therefore, a special offensive fish oil
 odor is not generated and the taste of milk is not changed.
 Example 44-48
 (Addition of Modified Fish Oil Composition to Milk)
 Samples of milk containing the modified fish oil composition are prepared
 by same procedure as Example 43, except using the before heat treatment
 modified fish oil composition obtained in Examples 18-22, then heated for
 30 minutes at 63.degree. C. Preserved in sealed containers at room
 temperature for 7 days. After 7 days, these containers are opened and
 whether there is a special fish oil odor or not for each samples are
 estimated by five panelists according to the evaluation standard shown in
 Table 1. Total points by five panelists for these samples are bigger than
 18, therefore, a special offensive fish oil odor is not generated and the
 taste of these samples of milk are not changed.
 Example 49
 (Manufacturing of Bread Containing Modified Fish Oil Composition)
 (1) At the kneading process of starting material of bread (100 weight parts
 of wheat powder, 3 weight parts of yeast, 3 weight parts of powdered milk,
 5 weight parts of sugar, 70 weight parts of water, 2 weight parts of salt,
 7 weight parts of margarine), the modified fish oil composition obtained
 in Example 17 is added to wheat powder, kneaded, fermentated and the bread
 base is prepared. After taking 60 minutes floor time, the bread base is
 divided, and take 30 minutes of bench time at room temperature. Then
 poured into a mold, maintained at the condition of 38.degree. C.
 temperature and 90% humidity for 30 minutes then bakes in oven
 (190.degree. C., 45 minutes) and obtain a bread.
 (2) Whether there is a special fish oil odor or not for the bread obtained
 in above mentioned procedure (1) is estimated by five panelists according
 to the evaluation standard shown in Table 1. Total points by five
 panelists for the bread is 19, therefore, a special offensive fish oil
 odor is not generated and the bread has a good flavor. The outer
 appearance, inner appearance, texture and taste of the bread are good, and
 there is no difference between ordinary bread baked without adding
 modified fish oil composition.
 Example 50-57
 (Manufacturing of Bread Containing Modified Fish Oil Composition)
 Samples of bread containing the modified fish oil composition are prepared
 by same procedure as Example 49, except using the before heat treatment
 modified fish oil composition obtained in Examples 18-25. Whether there is
 a special fish oil odor or not for each breads are estimated by five
 panelists according to the evaluation standard shown in Table 1. Total
 points by five panelists for these samples are bigger than 18, therefore,
 a special offensive fish oil odor is not generated and the taste of these
 breads are good. The outer appearance, inner appearance, texture and taste
 of the breads obtained in Examples 50-57 are good.
 Example 58
 (Manufacturing of Bean Curd Containing Modified Fish Oil Composition)
 (1) After soy beans are boiled, separated to soybean milk and bean-curd
 refuse. At the temperature of 70-75.degree. C., 0.003 weight parts of
 bittern and 0.3 weight parts of modified fish oil composition are added to
 1 weight parts of soybean milk (10-12%), and stirred in a stainless steel
 bowl. After settled for 20 minutes, transferred into a mold box and
 pressed by a hydraulic power jack, thus a bean curd is manufactured. (2)
 Whether there is a special fish oil odor or not for the bean curd obtained
 in above mentioned procedure (1) is estimated by five panelists according
 to the evaluation standard shown in Table 1. Total points by five
 panelists for the bean curd is 20, therefore, a special offensive fish oil
 odor is not generate, and the obtained bean curd has good flavor. The
 taste of the obtained bean curd are good, and there is no difference
 between ordinary bean curd manufactured without adding modified fish oil
 composition.
 Example 59-66
 (Manufacturing of Bean Curd Containing Modified Fish Oil Composition)
 Samples of bean curd containing the modified fish oil composition are
 prepared by same procedure as Example 58, except using the before heat
 treatment modified fish oil composition obtained in Examples 18-25.
 Whether there is a special fish oil odor or not for each bean curd are
 estimated by five panelists according to the evaluation standard shown in
 Table 1. Total points by five panelists for these samples are bigger than
 19, therefore, a special offensive fish oil odor is not generated and the
 taste of these bean curds are good, and there is no difference between
 ordinary bean curd manufactured without adding modified fish oil
 composition.
 Example 67
 (Preparation of Emulsion Containing Modified Fish Oil Composition)
 5 weight parts of modified fish oil composition obtained in Example 17 is
 added to 100 weight parts of the starting material of an emulsion (15
 weight parts of ethyl alcohol, 12 weight parts of propylene glycol, 3
 weight parts of glycerin, 2 weight parts of stearic acid, 1 weight parts
 of cetyl alcohol and 59 parts of water), mixed and stirred well at room
 temperature and an emulsion is prepared. The obtained emulsion is odorless
 and does not have special offensive fish oil odor, and after 1 month
 preservation does not generate offensive odor.
 Effect of Invention
 The modified fish oil type composition of this invention which can be
 obtained by adding at least one additive selected from vinegar and citrus
 fruits juice to the fish oil type material composed by at least one
 additive selected from a group composed by fish oil, highly unsaturated
 fatty acid derived from fish oil and ester of it, mixing, stirring then
 settling and removing water phase, and the modified fish oil composition
 obtained by adding vegetable oil to said material, can be applied to many
 kinds of field such as foods, cosmetics and medicines, because they have
 good preservation stability and maintain odorless state not only
 immediately after the preparation but also after long term preservation,
 further they have good heat stability which does not generate offensive
 odor when heated. And, since the modified fish oil type material and
 modified fish oil composition of this invention contain highly unsaturated
 fatty acid and/or esters thereof such as DHA or EPA which are useful for
 human body by large quantity, they are effective for reducing the content
 of choresterol in blood, for the prevention and the medical treatment of
 cardiac infraction, cerebral infraction and arteriosclerosis, for
 improvement of learning function, antitumor effect, anti-allergy effect
 and improvement of eye sight. Further, in the present invention, when at
 least one additive selected from the group composed by collagen, starch
 and agar--agar are added and used together with the vegetable oil, the
 modified fish oil composition which has more excellent clearness can be
 obtained.