【発明の詳細な説明】【０００１】【産業上の利用分野】本発明は、ドコサヘキサエン酸
（以下、ＤＨＡと略す）を高濃度に含有する天然油脂に
関する。【０００２】【従来の技術】ω３系高度不飽和脂肪酸を含有するグリ
セリドである天然油脂は、トリグリセリドの形態で魚油
等に多く含まれる。特にＤＨＡは、学習機能改善、抗動
脈硬化性、抗腫瘍性、免疫賦活、抗アレルギー等の有用
な生理活性を有することが知られている。このＤＨＡ
は、天然に存在するグリセリドである天然油脂には、構
成脂肪酸中多くても２０〜３０％であり、この他に大量
のパルミチン酸、ステアリン酸等の飽和脂肪酸や、リノ
ール酸に代表されるω６系高度不飽和脂肪酸が含まれて
いるため、この天然油脂を健康食品や医薬品として使用
する際に脂質過多の面で不都合である。このために、Ｄ
ＨＡ以外の脂肪酸を低減した油脂が酵素法によって調製
された（Ｙｕｋｉｈｉｓａ Ｔａｎａｋａ ｅｔ ａ
ｌ，Ｊｏｕｒｎａｌ ｏｆ Ａｍｅｒｉｃａｎ Ｏｉｌ
Ｃｈｅｍｉｃａｌ Ｓｏｃｉｅｔｙ，６９，（１９９
２） １２１０−１２１４）。【０００３】また、遊離の高純度ＤＨＡとグリセリンと
を原料に用いたリパーゼの合成反応や、高純度ＤＨＡエ
チルエステルとのリパーゼのエステル交換反応を利用し
て調製した高濃度ＤＨＡ油脂に関する報告（田中幸久
等、油化学、４１巻、１９９２年、５６３ー５６７頁お
よび特開平５ー３３１１０５）がなされている。【０００４】【発明が解決しようとする課題】上記に報告されている
ように、従来の技術では、リパーゼを用いた脂肪酸種に
対する最適な選択加水分解反応により得られる油脂です
ら、構成脂肪酸中のＤＨＡ含量が５３％であり、グリセ
リドの７５％がトリグリセリド、２４％がジグリセリ
ド、１％がモノグリセリドのトリグリセリドを主成分と
するものであった。また、リパーゼの合成反応やエステ
ル交換反応によって調製した油脂は、トリグリセリドか
らなるものであった。一般に食物として摂取されたトリ
グリセリドは、膵臓から分泌される消化酵素であるリパ
ーゼの作用により、ジグリセリドを経由して遊離の脂肪
酸とモノグリセリドとに加水分解され、分解されたモノ
グリセリドと遊離の脂肪酸は、胆汁酸塩とミセルを形成
し吸収されることが知られている。しかし、トリグリセ
リドからなる油脂は、分子内に親水性残基を有しないた
めに、水系に分散させるには高濃度の分散剤の使用や超
音波処理等の操作が必須であった。以上の点に鑑みて、
本発明は、水への分散性がよく、吸収性の良好な天然油
脂を提供することを目的とするものである。【０００５】【課題を解決するための手段】本発明者らは、上記課題
を解決するため鋭意研究を行った結果、目的を達成でき
る天然油脂として、ＤＨＡを高濃度に含有し、飽和脂肪
酸含量が少ない天然油脂を得ることに成功し、本発明を
完成するに到った。【０００６】すなわち、本発明は、油脂の構成脂肪酸の
うちＤＨＡを６０％以上含有し、グリセリド全体の中の
ジグリセリドの比率が７０％以上である天然油脂であっ
て、原料油脂をリパ−ゼ反応する際に水溶性高分子化合
物の存在下に行うことによって得られる天然油脂に関す
るものである。以下、本発明をさらに詳細に説明する。【０００７】本発明でいう天然油脂とは、天然に存在す
る脂肪酸グリセリンエステルまたは天然に存在する脂肪
酸グリセリンエステルを酵素分解して得られる脂肪酸グ
リセリンエステルを指す。本発明で得られる高濃度ＤＨ
Ａ含有油脂の原料としては、ＤＨＡを豊富に含む魚油、
鯨油等の海産性天然油脂や微生物由来の天然油脂を使用
することができる。これらの油脂を脂肪酸種に対する特
異性を利用して、ＤＨＡ以外の一般脂肪酸を選択的に加
水分解すればよいのであるが、加水分解に適した酵素と
しては、ＤＨＡに対して基質特異性の低いリパーゼであ
り、特にキャンディダ・シリンドラセやキャンディダ・
リポリティカ由来の酵素が好ましい。【０００８】上記の酵素により酵素反応を行なっても、
基質である油脂の他には水のみしか使用しない従来法に
よっては、ＤＨＡを６０％以上の高濃度に含有し、本発
明で規定する組成の天然油脂を得ることはできない。本
発明においては、リパーゼ反応を行なう際に、反応系に
水溶性高分子化合物を添加することによって、目的とす
る天然油脂を得ることができたのである。【０００９】リパーゼの反応系に添加する水溶性高分子
化合物は、リパーゼ反応を阻害しない性質のものであれ
ばよく、天然由来でも合成高分子化合物でもよい。天然
由来の水溶性高分子化合物としては、可溶性澱粉、デキ
ストリン、デキストラン、ペクチン、アラビアゴム、キ
サンタンガム等の天然高分子糖類化合物、ゼラチン、コ
ーン蛋白質由来ペプチド等のアミノ酸高分子化合物、カ
ルボキシメチルセルローズ等のセルロース誘導体等を使
用することができる。合成高分子化合物としては、ポリ
ビニールアルコール等を使用することができる。リパー
ゼの反応系に添加するこれらの水溶性高分子化合物の濃
度は、使用する油脂の濃度によっても変化するが、カル
ボキシメチルセルラース、カチナール、ペクチン、キサ
ンタンガム等の化合物では０．１〜５％の範囲で使用で
き、好ましくは０．５〜２％であり、ゼラチン、コーン
由来ペプチド、可溶性澱粉、デキストラン、アラビアゴ
ム等の化合物では１〜２０％の範囲で使用でき、好まし
くは２〜５％である。【００１０】上記酵素で加水分解する反応は、酵素の活
性を発現するのに十分の量の水の存下で行うが、その量
は、油脂に対して１〜３００％であり、好ましくは４０
〜１００％程度である。前記酵素の使用量は、基質に含
有される高度不飽和脂肪酸の濃度、反応温度、反応ｐ
Ｈ、反応時間によっても変わるが、油脂１ｇあたり１０
〜１０００ユニット（Ｕ）であり、好ましくは５０〜３
００ユニット（Ｕ）程度である。反応温度はリパーゼが
失活しない範囲（２０〜６０℃）で適宜選ぶことができ
るが、特に好ましくは２５〜４０℃である。【００１１】また、加水分解の反応におけるｐＨを一定
に保つために、水の代わりに緩衝液を用いてもよい。ｐ
Ｈは７〜９の範囲で反応できるが、特に好ましくは７．
５〜８．５である。さらに、加水分解の反応を速めるた
めに、カルシウムやマグネシウム等の２価の金属イオン
を反応液に添加してもよい。その濃度は１０〜５００ｍ
Ｍの範囲で使用できるが、特に好ましくは１５０〜２５
０ｍＭのカルシウムイオンを用いる。酵素反応は空気の
存在下でも十分に問題なく進行するが、一般的に高度不
飽和脂肪酸は酸化されやすいので、窒素やアルゴンガス
等の不活性ガス用いて、酸素を制限した環境下で反応を
行う方が好ましい。【００１２】油脂の加水分解率は、遊離した脂肪酸をア
ルカリで滴定して測定する方法やガスクロマトグラフィ
ー等の方法で求めることができるが、脂肪酸種の総量と
脂肪酸種の分離定量が同時にできるガスクロマトグラフ
ィーが測定精度の点で有利である。加水分解の測定は次
式により求めた。【数１】加水分解率は６０〜８０％の範囲になるように制御すれ
ばよいが、好ましくは６５〜７５％である。【００１３】上記の酵素を使用し、酵素反応を行なう際
に、反応系に水溶性高分子化合物を添加することによ
り、高度不飽和脂肪酸含有油脂に含まれる高度不飽和脂
肪酸エステルを殆ど加水分解しないか、もしくは加水分
解してもその程度は極めて低いので、高度不飽和脂肪酸
以外の脂肪酸は優先的に加水分解されるために、これを
除去し未分解で残存するグリセリドを分離回収すれば、
高度不飽和脂肪酸特にＤＨＡを高濃度に含有するジグリ
セリド、モノグリセリドを主成分とする油脂を得ること
ができる。上記のリパーゼによる加水分解油よりグリセ
リド（天然油脂）画分を採取するには、通常行われてい
るアルカリ脱酸法、水蒸気蒸留法、イオン交換樹脂によ
る分画、分子蒸留、吸着クロマト等の手段を利用すれば
よく、特にその方法は問わい。【００１４】【発明の効果】本発明の天然油脂は、ＤＨＡを高濃度に
含有し、ジグリセリド、モノグリセリドを主成分として
いるため消化吸収に優れており、また、飽和脂肪酸の含
有率が極めて低いためにエネルギー過剰摂取の問題が少
なく、さらに、水系で使用する際に良好な分散性を有し
ており、ＤＨＡの有用な生理活性を発現しやすく成人病
の予防や治療に有効に用いられる。【００１５】【実施例】以下に、実施例を挙げて本発明をさらに詳細
に説明するが、本発明は、これによりなんら限定される
ものではない。（実施例１）０．０５Ｍトリスー塩酸緩衝液（ｐＨ８．
２）、０．２Ｍ塩化カルシウム、５％アラビアゴムから
構成される反応液１００ｍｌに１２，５００ユニットの
キャンディダ・リポリティカ由来のリパーゼ（天野製薬
社製）を溶解し、さらに、マグロ頭部より採取した魚油
Ａ（脂肪酸組成は表１に記載）１０ｇを混合して４５℃
で１５時間撹拌し、２Ｎ水酸化ナトリウムで連続的にｐ
Ｈを８．２に調整しながら加水分解反応を行い、分解油
を得た。ヘキサン１００ｍｌで油脂を抽出し、遠心分離
（３，０００回転、１０分間）後、ヘキサン層を回収し
た。この抽出液に４０ｍｌのアセトン、次いで、２０ｍ
ｌの０．３Ｎ水酸化ナトリウム溶液を加え、室温で１時
間撹拌した。遊離の脂肪酸が除去されたグリセリドがヘ
キサン層に回収でき、溶媒を減圧下で溜去した重量は
２．３ｇであった。本品をアルカリで鹸化後、メチルエ
ステル誘導体に変換し、ガスクロマトグラフィー法によ
り脂肪酸組成を測定した。その測定結果を表１に示し
た。脂肪酸中のＤＨＡ含量は６３．９％であった。【００１６】（比較例１）実施例１に示した魚油Ａを他の原料である魚油Ｂ（脂肪
酸組成は表２に記載）に変えて、他は同じ条件で酵素反
応と抽出、精製を行い、最終的に３．４ｇのグリセリド
を得た。その脂肪酸組成を表２に示した。本品をアルカ
リで鹸化後、メチルエステル誘導体に変換し、ガスクロ
マトグラフィー法により脂肪酸組成を測定した。その測
定結果を表１に示した。脂肪酸中のＤＨＡ含量は６３．
２％であった。【００１７】【表１】【００１８】【表２】【００１９】（実施例２）実施例１で得られた油脂１ｇをクロロホルム：アセトン
（９５：４、ｖ／ｖ）５ｍｌに溶解し、同じ組成の混合
溶媒に懸濁し充填したシリカゲルカラムにかけ、同一組
成の混合溶媒で溶出した。薄層クロマトにより各グリセ
リドを検出してトリグリセリド、ジグリセリドを含む画
分を得（２００ｍｌ）、次いで、この画分を減圧下で溶
媒を溜去して０．７８ｇの油脂を得た。比較例１および
実施例２で得られた油脂について、イアトロスキャンを
用いてグリセリドの組成を測定した。結果を表３に示し
た。【００２０】【表３】【００２１】また、比較例１、実施例２で得られた油脂
および魚油Ｂ各々０．２ｇを２ｍｌの精製水に加え、ホ
モゲナイザー（０℃、６０００回転）で５分間処理し
た。処理後の油脂分散液を４℃に２０時間静置して、そ
の状態変化を観察した。表４に結果を示した。【００２２】【表４】−：油脂と水とが２層に完全に分離＋＋＋：完全に分散した状態で２層に分離していない＋＋：分散状態は良好であるが、一部僅かに分離した状
態【００２３】また、比較例１および実施例２で得られた
油脂を、表５に示した条件で３５℃で２週間静置した
後、油脂の分析をイヤトロスキャンを用いて行った。結
果を表６に示した。実施例２で得られた油脂は、水溶液
でも油脂の状態でも安定であったが、比較例１で得られ
た油脂は、モノグリセリドが水溶液状態でのみ僅かに分
解を受けた。【００２４】【表５】＊Ａ−Ｄ共に密閉容器を使用して気相は窒素で置換し
た。【００２５】【表６】Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a natural fat or oil containing docosahexaenoic acid (hereinafter abbreviated as DHA) at a high concentration. [0002] Natural oils and fats, which are glycerides containing ω3 polyunsaturated fatty acids, are often contained in fish oils and the like in the form of triglycerides. In particular, DHA is known to have useful physiological activities such as improvement of learning function, anti-atherosclerosis, anti-tumor, immunostimulation, and anti-allergy. This DHA
Natural fats and oils, which are naturally occurring glycerides, contain at most 20 to 30% of the constituent fatty acids. In addition, large amounts of saturated fatty acids such as palmitic acid and stearic acid and ω6 represented by linoleic acid Since these natural fats and oils are used as health foods and pharmaceuticals, they are inconvenient in terms of lipid excess because they contain system unsaturated fatty acids. For this, D
Fats and oils reduced in fatty acids other than HA were prepared by an enzymatic method (Yukihisa Tanaka et a).
1, Journal of American Oil
Chemical Society, 69, (199
2) 1210-1214). [0003] Further, a report on a high-concentration DHA oil / fat prepared by using a lipase synthesis reaction using free high-purity DHA and glycerin as raw materials or a transesterification reaction of lipase with high-purity DHA ethyl ester (Tanaka). Yukihisa et al., Oil Chemistry, 41, 1992, pp. 563-567 and JP-A-5-331105). [0004] As reported above, in the prior art, even fats and oils obtained by an optimal selective hydrolysis reaction of fatty acid species using a lipase, even in fats and oils contained in the constituent fatty acids. The DHA content was 53%, and 75% of the glyceride was mainly composed of triglyceride, 24% of diglyceride, and 1% of monoglyceride as a main component. In addition, fats and oils prepared by a lipase synthesis reaction or a transesterification reaction consisted of triglycerides. Generally, triglyceride ingested as food is hydrolyzed to free fatty acids and monoglycerides via diglycerides by the action of lipase, a digestive enzyme secreted from the pancreas, and the decomposed monoglycerides and free fatty acids are converted into bile. It is known to form and absorb micelles with acid salts. However, since fats and oils composed of triglycerides do not have a hydrophilic residue in the molecule, operations such as use of a high-concentration dispersant and ultrasonic treatment were essential to disperse them in an aqueous system. In view of the above,
An object of the present invention is to provide a natural fat / oil having good dispersibility in water and good absorbability. The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems. As a result, the present inventors have found that DHA is contained at a high concentration as a natural fat and oil capable of achieving the object, and a saturated fatty acid content is obtained. The present invention succeeded in obtaining natural fats and oils with a small amount, and completed the present invention. [0006] That is, the present invention relates to anatural fat oroil containing 60% or more of DHA among the constituent fatty acids of the fat and oil, and having a diglyceride ratio of 70% or more in the whole glyceride.
Water-soluble polymer compound
The present invention relatesto natural fats and oilsobtained by performing in the presence of a product . Hereinafter, the present invention will be described in more detail. [0007] The term "natural fat / oil" as used in the present invention means a naturally occurring fatty acid glycerin ester or a fatty acid glycerin ester obtained by enzymatically decomposing a naturally occurring fatty acid glycerin ester. High concentration DH obtained by the present invention
Raw materials for A-containing fats and oils include fish oil rich in DHA,
Marine natural fats and oils such as whale oil and microorganism-derived natural fats and oils can be used. These fats and oils may be selectively hydrolyzed to general fatty acids other than DHA by utilizing the specificity for fatty acid species. However, as enzymes suitable for hydrolysis, substrates having low substrate specificity for DHA are preferred. It is a lipase, especially Candida Sylindrase and Candida
Enzymes derived from Ripolitica are preferred. [0008] Even when an enzyme reaction is carried out with the above enzyme,
According to the conventional method using only water in addition to the substrate fats and oils, it is not possible to obtain natural fats and oils containing DHA at a high concentration of 60% or more and having the composition specified in the present invention. In the present invention, the desired natural fats and oils could be obtained by adding a water-soluble polymer compound to the reaction system when performing the lipase reaction. The water-soluble polymer compound to be added to the lipase reaction system only has to have a property that does not inhibit the lipase reaction, and may be a naturally occurring or synthetic polymer compound. Examples of the naturally occurring water-soluble polymer compound include soluble starch, dextrin, dextran, pectin, gum arabic, natural polymer saccharide compounds such as xanthan gum, gelatin, amino acid polymer compounds such as corn protein-derived peptides, and carboxymethyl cellulose. Cellulose derivatives and the like can be used. Polyvinyl alcohol or the like can be used as the synthetic polymer compound. The concentration of these water-soluble polymer compounds to be added to the lipase reaction system varies depending on the concentration of fats and oils used, but 0.1 to 5% for compounds such as carboxymethylcellulose, katinal, pectin and xanthan gum. It can be used in the range of 0.5 to 2%, and can be used in the range of 1 to 20% for compounds such as gelatin, corn-derived peptide, soluble starch, dextran and gum arabic, and preferably 2 to 5%. is there. [0010] The reaction of hydrolysis with the above enzyme is carried out in the presence of water in an amount sufficient to exhibit the activity of the enzyme.
About 100%. The amount of the enzyme used depends on the concentration of the polyunsaturated fatty acid contained in the substrate, the reaction temperature, and the reaction p.
H, depending on the reaction time, 10 g / g
~ 1000 units (U), preferably 50-3
It is about 00 units (U). The reaction temperature can be appropriately selected within a range in which lipase is not inactivated (20 to 60 ° C), and particularly preferably 25 to 40 ° C. A buffer may be used instead of water in order to keep the pH in the hydrolysis reaction constant. p
H can be reacted in the range of 7 to 9, but is particularly preferably 7.
5 to 8.5. Further, a divalent metal ion such as calcium or magnesium may be added to the reaction solution in order to accelerate the hydrolysis reaction. Its concentration is 10-500m
Although it can be used in the range of M, particularly preferably 150 to 25
Use 0 mM calcium ions. The enzymatic reaction proceeds without any problem even in the presence of air, but polyunsaturated fatty acids are generally easily oxidized, so use an inert gas such as nitrogen or argon gas to perform the reaction in an oxygen-restricted environment. It is preferable to do so. The rate of hydrolysis of fats and oils can be determined by a method such as titration of liberated fatty acids with an alkali or by a method such as gas chromatography. Chromatography is advantageous in terms of measurement accuracy. The hydrolysis was determined by the following equation. (Equation 1) The hydrolysis rate may be controlled so as to be in the range of 60 to 80%, but is preferably 65 to 75%. When the above enzyme is used to carry out the enzymatic reaction, by adding a water-soluble polymer compound to the reaction system, the highly unsaturated fatty acid ester contained in the fat and oil containing the highly unsaturated fatty acid is hardly hydrolyzed. Or, since the degree of hydrolysis is extremely low, fatty acids other than polyunsaturated fatty acids are preferentially hydrolyzed, so if this is removed and undecomposed residual glyceride is separated and collected,
It is possible to obtain oils and fats containing diglycerides and monoglycerides containing polyunsaturated fatty acids at a high concentration, especially DHA at a high concentration. In order to collect a glyceride (natural oil and fat) fraction from the hydrolyzed oil by the above lipase, a commonly used means such as an alkali deacidification method, a steam distillation method, a fractionation using an ion exchange resin, a molecular distillation, an adsorption chromatography, etc. The method may be used. The natural fats and oils of the present invention contain DHA at a high concentration and are mainly composed of diglycerides and monoglycerides, so that they are excellent in digestion and absorption, and the content of saturated fatty acids is extremely low. In addition, it has few problems of excessive energy intake, and has good dispersibility when used in an aqueous system, and easily exhibits useful physiological activity of DHA, and is effectively used for prevention and treatment of adult diseases. EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited thereto. (Example 1) 0.05 M Tris-HCl buffer (pH 8.
2) Dissolve 12,500 units of lipase derived from Candida lipolytica (manufactured by Amano Pharmaceutical Co., Ltd.) in 100 ml of a reaction solution composed of 0.2 M calcium chloride and 5% gum arabic, and further collect from the tuna head 45 g of mixed fish oil A (fatty acid composition is described in Table 1) 10 g
For 15 hours and continuously p with 2N sodium hydroxide.
The hydrolysis reaction was performed while adjusting H to 8.2, to obtain a decomposed oil. Oils and fats were extracted with 100 ml of hexane, centrifuged (3,000 rpm, 10 minutes), and the hexane layer was recovered. 40 ml of acetone, then 20 m
l of 0.3N sodium hydroxide solution was added, and the mixture was stirred at room temperature for 1 hour. Glyceride from which free fatty acids had been removed could be recovered in the hexane layer, and the weight of the solvent distilled off under reduced pressure was 2.3 g. This product was saponified with an alkali, converted to a methyl ester derivative, and the fatty acid composition was measured by gas chromatography. Table 1 shows the measurement results. The DHA content in the fatty acids was 63.9%.Comparative Example 1 Enzyme reaction, extraction and purification were carried out under the same conditions except that fish oil A shown in Example 1 was replaced with fish oil B (fatty acid composition is described in Table 2) as another raw material. Finally, 3.4 g of glyceride was obtained. The fatty acid composition is shown in Table 2. This product was saponified with an alkali, converted to a methyl ester derivative, and the fatty acid composition was measured by gas chromatography. Table 1 shows the measurement results. The DHA content in the fatty acids is 63.
2%. [Table 1] [Table 2] Example2 1 g of the oil or fat obtained in Example 1 was dissolved in 5 ml of chloroform: acetone (95: 4, v / v), and the solution was applied to a silica gel column filled and suspended in a mixed solvent having the same composition. Elution was carried out with a mixed solvent of the composition. Each glyceride was detected by thin layer chromatography to obtain a fraction containing triglyceride and diglyceride (200 ml). Then, the solvent was distilled off from this fraction under reduced pressure to obtain 0.78 g of oil and fat.With respect to the fats and oils obtained inComparative Example 1 and Example2 , the composition of glyceride was measured using Iatroscan. The results are shown in Table 3. [Table 3] Further, 0.2 g of each of the fats and oils and fish oil B obtained inComparative Example 1 and Example2 were added to 2 ml of purified water, and treated with a homogenizer (0 ° C., 6000 rpm) for 5 minutes. The treated oil and fat dispersion was allowed to stand at 4 ° C. for 20 hours, and its state change was observed. Table 4 shows the results. [Table 4] -: Oil and fat completely separated into two layers +++: completely dispersed and not separated into two layers ++: dispersed state is good, but partially separated slightly.After the oils and fats obtained inComparative Example 1 and Example2 were allowed to stand at 35 ° C. for 2 weeks under the conditions shown in Table 5, the analysis of the oils and fats was performed by using an ear scan. The results are shown in Table 6. The oils and fats obtained in Example2 were stable both in an aqueous solution and in the state of oils and fats, but the oils and fats obtained inComparative Example 1 were slightly decomposed only in a monoglyceride aqueous solution state. [Table 5] * For both A and D, a closed vessel was used and the gas phase was replaced with nitrogen. [Table 6]
─────────────────────────────────────────────────────フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) C11C 3/00 - 3/14 C11B 3/02 - 3/08 C11B 7/00 A23D 9/00 - 9/06 ＪＩＣＳＴファイル（ＪＯＩＳ)──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl.7 , DB name) C11C 3/00-3/14 C11B 3/02-3/08 C11B 7/00 A23D 9/00-9 / 06 JICST file (JOIS)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21830094AJP3526632B2 (en) | 1994-08-22 | 1994-08-22 | Fats and oils containing highly unsaturated fatty acids |
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21830094AJP3526632B2 (en) | 1994-08-22 | 1994-08-22 | Fats and oils containing highly unsaturated fatty acids |
| Publication Number | Publication Date |
|---|---|
| JPH0860181A JPH0860181A (en) | 1996-03-05 |
| JP3526632B2true JP3526632B2 (en) | 2004-05-17 |
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21830094AExpired - Fee RelatedJP3526632B2 (en) | 1994-08-22 | 1994-08-22 | Fats and oils containing highly unsaturated fatty acids |
| Country | Link |
|---|---|
| JP (1) | JP3526632B2 (en) |
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6762203B2 (en) | 1999-08-03 | 2004-07-13 | Kao Corporation | Oil composition |
| JP4098927B2 (en)* | 1999-08-03 | 2008-06-11 | 花王株式会社 | Oil composition |
| JP3752127B2 (en)* | 2000-03-21 | 2006-03-08 | 花王株式会社 | Oil composition |
| JP4995377B2 (en)* | 2001-04-26 | 2012-08-08 | 花王株式会社 | Oil composition |
| US20040209953A1 (en)* | 2002-12-06 | 2004-10-21 | Wai Lee Theresa Siu-Ling | Glyceride compositions and methods of making and using same |
| ES2264886B1 (en)* | 2005-05-12 | 2008-02-01 | Proyecto Empresarial Brudy, S.L. | USE OF DOCOSAHEXAENOIC ACID FOR THE TREATMENT OF TUMOR DISEASES. |
| JP4719715B2 (en)* | 2007-05-18 | 2011-07-06 | 花王株式会社 | Oil composition |
| JP4862022B2 (en)* | 2008-08-11 | 2012-01-25 | 花王株式会社 | Insulin resistance improving agent |
| JP2020503388A (en)* | 2016-12-23 | 2020-01-30 | ビーエーエスエフ エーエス | Omega-3 fatty acid composition for preventing and / or treating cachexia |
| Publication number | Publication date |
|---|---|
| JPH0860181A (en) | 1996-03-05 |
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