JP2697834B2 - Artificial milk with polyunsaturated fatty acid component - Google Patents

Artificial milk with polyunsaturated fatty acid component

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Publication number
JP2697834B2
JP2697834B2 JP63021170A JP2117088A JP2697834B2 JP 2697834 B2 JP2697834 B2 JP 2697834B2 JP 63021170 A JP63021170 A JP 63021170A JP 2117088 A JP2117088 A JP 2117088A JP 2697834 B2 JP2697834 B2 JP 2697834B2
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JP
Japan
Prior art keywords
fatty acid
milk
acid
fat
oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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JP63021170A
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Japanese (ja)
Other versions
JPH01196255A (en
Inventor
芳史 新免
健吾 秋元
秀明 山田
昌 清水
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Suntory Ltd
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Suntory Ltd
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Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は粉末ミルク又は液体ミルク等の人工乳中に欠
けている又は不足している微量脂肪酸成分を強化した人
工乳に関する。
Description: FIELD OF THE INVENTION The present invention relates to an artificial milk in which a trace fatty acid component missing or missing in an artificial milk such as powdered milk or liquid milk is fortified.

〔従来の技術〕[Conventional technology]

γ−リノレン酸、エイコサジエン酸、ビスホモγ−リ
ノレン酸、アラキドン酸、及びエイコサペンタエン酸
(各々以下GLA、EDA、DGLA、ARA、EPAと略す)は高等動
物に不可欠な脂肪酸であり、生体内では、血圧調節作
用、ホルモン分泌調節作用等、重要な働きを示すプロス
タグランディン類の前駆体として、これら自身も生理活
性を有する高度不飽和脂肪酸である。これらは、必須脂
肪酸であるリノール酸やα−リノレン酸から不飽和化酵
素(desaturase)と炭素鎖伸長酵素(elongation enzym
e)によって誘導される。このうちデサチュラーゼは、
老化、癌、糖尿病その他の疾病により、活性が弱めら
れ、その結果プロスタグランディン生成が抑制されるの
で種々の健康障害を引き起こすことが知られている。従
って上記の高度不飽和脂肪酸を直接摂取することは、こ
れらの健康障害に対する治療法又は予防法として有効で
ある。
γ-linolenic acid, eicosadienoic acid, bishomo γ-linolenic acid, arachidonic acid, and eicosapentaenoic acid (hereinafter abbreviated as GLA, EDA, DGLA, ARA, and EPA) are indispensable fatty acids for higher animals, and in vivo, As precursors of prostaglandins that have important functions such as blood pressure regulation and hormone secretion regulation, they are themselves highly unsaturated fatty acids having physiological activity. These are derived from essential fatty acids such as linoleic acid and α-linolenic acid, from desaturases and elongation enzymes.
Induced by e). Of these, desaturase is
It is known that aging, cancer, diabetes and other diseases weaken the activity and consequently suppress the production of prostaglandins, thereby causing various health disorders. Therefore, directly ingesting the above-mentioned polyunsaturated fatty acids is effective as a treatment or prevention for these health disorders.

乳児においては、これらの高度不飽和脂肪酸は母乳か
ら得ている。高度不飽和脂肪酸から誘導されるプロスタ
グランディン類は免疫機能の発現にも関与していると言
われ、乳児にとってこれらの成分を母体から吸収するこ
とは、生命維持のために非常に重要な要素となってい
る。
In infants, these polyunsaturated fatty acids are obtained from breast milk. It is said that prostaglandins derived from polyunsaturated fatty acids are also involved in the expression of immune function, and that absorption of these components from the mother for infants is a very important factor for life support. It has become.

しかしながら、ヒトの天然母乳中の前記脂肪酸類の含
有量が正確に知られておらず、また前記の脂肪酸類が非
常に高価であること等のため、粉ミルクや液体ミルク等
の人工乳に微量脂肪酸類を添加して、ヒト天然母乳と同
等又はそれ以上の脂肪酸組成を有する粉ミルクが液体ミ
ルクや製造することは困難であった。
However, since the content of the fatty acids in human natural breast milk is not accurately known, and the fatty acids are very expensive, etc., trace amounts of fatty acids are contained in artificial milk such as powdered milk and liquid milk. It has been difficult to produce powdered milk having a fatty acid composition equal to or greater than that of human natural milk by adding liquid milk or liquid milk.

〔発明が解決しようとする課題〕[Problems to be solved by the invention]

従って本発明は、微量脂肪酸類が強化されており、ヒ
ト天然母乳に近い脂肪酸組成を有するミルクを提供しよ
うとするものである。
Accordingly, an object of the present invention is to provide a milk which is enriched in trace fatty acids and has a fatty acid composition close to that of natural human milk.

〔課題を解決するための手段〕[Means for solving the problem]

本発明者等は、ヒト天然母乳の脂肪酸組成、及び通常
の方法により製造される粉ミルク類の脂肪酸組成を解明
し、これらを比較することにより、粉ミルク類にはGL
A、EDA、DGLA、ARA、EPA等が不足していることを明らか
にし、他方これらの脂肪酸を発酵法により安価に製造す
る方法を別途発明し、本発明を完成した。
The present inventors have elucidated the fatty acid composition of human natural breast milk and the fatty acid composition of milk powders produced by an ordinary method, and by comparing these, GLs in milk powders have been identified.
The inventors clarified that A, EDA, DGLA, ARA, EPA, etc. were deficient, and separately invented a method for producing these fatty acids at low cost by fermentation, thereby completing the present invention.

従って本発明は、エイコサジエン酸、ビスホモ−γ−
リノレン酸もしくはアラキドン酸、又は前記脂肪酸のエ
ステル、前記脂肪酸を含有する油脂、前記油脂の加水分
解物もしくは前記油脂分解物のエステル化物をそれぞれ
単独で又は混合して添加し、あるいは、さらにそれらの
ほかにγ−リノレン酸もしくはエイコサペンタエン酸、
又は前記脂肪酸のエステル、前記脂肪酸を含有する油
脂、前記油脂の加水分解物もしくは前記油脂分解物のエ
ステル化物をそれぞれ単独で又は混合して添加した人工
乳を提供する。
Therefore, the present invention provides eicosadienoic acid, bishomo-γ-
Linolenic acid or arachidonic acid, or an ester of the fatty acid, an oil or fat containing the fatty acid, a hydrolyzate of the oil or fat, or an esterified product of the oil or fat decomposed product is added alone or in combination, or further. Γ-linolenic acid or eicosapentaenoic acid,
Alternatively, the present invention provides an artificial milk to which an ester of the fatty acid, a fat or oil containing the fatty acid, a hydrolyzate of the fat or oil, or an esterified product of the fat or fat decomposition product is added alone or in combination.

〔具体的な説明〕[Specific explanation]

まず、ヒト母乳(産後5ケ月)及び2種類の市販粉ミ
ルク(13g/100mlの濃度で水に溶かしたもの)の脂肪酸
組成を次の表に示す。
First, the following table shows the fatty acid composition of human breast milk (five months after birth) and two types of commercially available powdered milk (dissolved in water at a concentration of 13 g / 100 ml).

従って天然母乳と人工乳を比較した場合、人工乳には
γ−リノレン酸、エイコサジエン酸、ビスホモγ−リノ
レン酸、アラキドン酸、エイコサペンタエン酸等の微量
脂肪酸が不足している。従って本発明においては、粉子
等、人工乳の製造行程において又は製品に上記のごとき
脂肪酸を添加することにより、天然母乳に近い微量脂肪
酸組成を有する人工乳を得る。
Therefore, when natural breast milk is compared with artificial milk, the artificial milk is deficient in trace fatty acids such as γ-linolenic acid, eicosadienoic acid, bishomo γ-linolenic acid, arachidonic acid and eicosapentaenoic acid. Therefore, in the present invention, an artificial milk having a trace amount of fatty acid composition close to that of natural mother milk is obtained in the process of producing artificial milk, such as powder, or by adding the above-described fatty acid to the product.

この場合上記脂肪酸の添加量は種々の条件により異
る。例えば、ヒト母乳の脂肪酸組成は出産後の経過期間
と共に変化すると考えられるから、脂肪酸の添加量は出
産後いかなる時期の授乳に供する人工乳を目的とするか
により異る。また、人工乳の原料、人工乳の製造行程等
によっても異る。従って、本発明においては、これらの
条件に応じて上記の脂肪酸又は脂肪酸含有物を単独で又
は組合わせて加える。
In this case, the amount of the fatty acid to be added varies depending on various conditions. For example, since the fatty acid composition of human breast milk is considered to change with the lapse of time after childbirth, the amount of the fatty acid to be added differs depending on at what time after childbirth the purpose is to formulate milk for lactation. It also varies depending on the raw material of the artificial milk, the production process of the artificial milk, and the like. Therefore, in the present invention, the above fatty acids or fatty acid-containing substances are added alone or in combination depending on these conditions.

例えば、乾燥製品に対してγ−リノレン酸0.02〜0.03
%、エイコサジエン酸0.05〜0.08%、ビスホモγ−リノ
レン酸0.05〜0.08%、アラキドン酸0.2〜0.3%、エイコ
サペンタエン酸0.01〜0.03%を添加する。また、複数の
脂肪酸を含有する材料、例えば脂質やその加水分解物等
を使用する場合には、これと単独の脂肪酸類とを適宜組
合わせて目的とする量の脂肪酸類を強化することができ
る。一般的な添加量の範囲としては、脂肪酸又は脂肪酸
エステルの量は、粉末ミルクの場合0.001〜2重量%が
好ましく、液体ミルクの場合0.0001〜0.2%程度が好ま
しい。
For example, 0.02-0.03 γ-linolenic acid for the dried product
%, Eicosadienoic acid 0.05-0.08%, bis-homo gamma-linolenic acid 0.05-0.08%, arachidonic acid 0.2-0.3%, and eicosapentaenoic acid 0.01-0.03%. Further, when a material containing a plurality of fatty acids, for example, a lipid or a hydrolyzate thereof is used, a desired amount of the fatty acids can be strengthened by appropriately combining this with a single fatty acid. . As a general range of the addition amount, the amount of the fatty acid or fatty acid ester is preferably 0.001 to 2% by weight in the case of powdered milk, and about 0.0001 to 0.2% in the case of liquid milk.

前記の脂肪酸は種々の形態で添加することができる。
例えば遊離の脂肪酸として添加することもでき、又それ
らの塩、例えばナトリウム塩、カリウム塩等として加え
ることもできる。エステル、例えばメチルエステル又は
エチルエステルとして添加することもできる。また、上
記の脂肪酸を高比率で含有する脂質、例えばトリグリセ
ライド、又はその加水分解物、あるいはこの加水分解物
をエステル化、例えばメチルエステル化もしくはエチル
エステル化したもの、等の形で使用することができる。
The above fatty acids can be added in various forms.
For example, they can be added as free fatty acids, or their salts, for example, sodium salts, potassium salts and the like. It can also be added as an ester, for example a methyl ester or an ethyl ester. In addition, lipids containing a high proportion of the above fatty acids, for example, triglyceride, or a hydrolyzate thereof, or esterification of the hydrolyzate, such as those obtained by esterification, for example, methyl ester or ethyl ester, may be used. it can.

上記脂肪酸は、これを個々の脂肪酸の形で単独で又は
2種類以上混合して使用する場合、これらは、任意の製
造法により製造されたものを使用することができる。例
えば、上記の不飽和脂肪酸の高い生産能を有するモルテ
ィエレア属に属する微生物を使用して、発酵法、酵素法
等により添加物を調製することができる。例えば、該モ
ルティエラ属微生物を培養し、その培養菌体を、所望に
より乾燥した後、有機溶剤で抽出し、この抽出物を蒸発
乾固することにより得られる脂質は前記の不飽和脂肪酸
を高比率で含んでおり、この脂質を本発明の原料脂質と
して使用することができる。また、この脂質を常法に従
って加水分解することにより脂肪酸混合物、又は脂肪酸
塩混合物、例えばナトリウム塩混合物が得られ、これら
を本発明の脂肪酸原料として使用することができる。さ
らに、これらの脂肪酸混合物を常法に従ってエステル化
し、脂肪酸エステル、例えばメチルエステル又はエチル
エステル、の混合物を得、これを本発明の脂肪酸原料と
して使用することができる。さらに、この様にして得ら
れた脂肪酸混合物又は脂肪酸エステル混合物を個々の脂
肪酸もしくは脂肪酸塩又は脂肪酸エステルとして単離し
た後、これらを使用することができる。
When the above-mentioned fatty acids are used alone or in combination of two or more kinds in the form of individual fatty acids, those produced by any production method can be used. For example, an additive can be prepared by a fermentation method, an enzymatic method, or the like using a microorganism belonging to the genus Mortierea having a high productivity of unsaturated fatty acids. For example, after culturing the Mortierella microorganism, drying the cultured cells if desired, extracting with an organic solvent, and evaporating the extract to dryness, the lipid obtained by the above-mentioned unsaturated fatty acid has a high content. This lipid can be used as a raw material lipid of the present invention. Further, a fatty acid mixture or a fatty acid salt mixture such as a sodium salt mixture is obtained by hydrolyzing the lipid according to a conventional method, and these can be used as the fatty acid raw material of the present invention. Further, these fatty acid mixtures are esterified according to a conventional method to obtain a mixture of fatty acid esters such as methyl ester or ethyl ester, which can be used as the fatty acid raw material of the present invention. Further, the fatty acid mixture or fatty acid ester mixture thus obtained can be used after being isolated as individual fatty acids or fatty acid salts or fatty acid esters.

上記の脂肪酸もしくはその塩、又は脂肪酸エステル、
あるいはこれらの混合物は、そのまま使用することもで
きるが、より良い均一性を得るためにこれらをシクロデ
キストリンの包接化合物とした後、粉末ミルクや液体ミ
ルクに添加するのが良い。シクロデキストリンはα,
β,γいずれのタイプも用いることができる。GLA、ED
A、DGLA、ARAもしくはEPAの脂肪酸又は脂肪酸エステル
から、シクロデキストリンの包接化合物の合成は下記の
ごとく行なう。シクロデキストリンの飽和あるいは過飽
和水溶液中に、一定量のGLA、EDA、DGLA、ARA、EPA等を
脂肪酸の形で又は脂肪酸エステルの形で添加し、10分〜
10時間攪拌することにより、沈殿物として包接化合物が
得られる。又、シクロデキストリンに少量の水を加え、
ミキサーで練り混ぜながら、一定量のGLA、EDA、DGLA、
ARA、EPAを脂肪酸の形で又は脂肪酸エステルの形で添加
し、1〜5時間攪拌することにより包接化合物が得られ
る。
The above fatty acids or salts thereof, or fatty acid esters,
Alternatively, these mixtures can be used as they are, but in order to obtain better homogeneity, it is preferable to add them to powdered milk or liquid milk after forming them as inclusion compounds of cyclodextrin. Cyclodextrin is α,
Both β and γ types can be used. GLA, ED
The synthesis of the inclusion compound of cyclodextrin from the fatty acid or fatty acid ester of A, DGLA, ARA or EPA is performed as follows. In a saturated or supersaturated aqueous solution of cyclodextrin, add a certain amount of GLA, EDA, DGLA, ARA, EPA, etc. in the form of a fatty acid or in the form of a fatty acid ester.
After stirring for 10 hours, the inclusion compound is obtained as a precipitate. Also, add a small amount of water to cyclodextrin,
While mixing with a mixer, a certain amount of GLA, EDA, DGLA,
Addition of ARA or EPA in the form of a fatty acid or in the form of a fatty acid ester and stirring for 1 to 5 hours give an inclusion compound.

本発明の人工乳には、必要に応じて、酸化防止のた
め、トコフェロール、セサモール、メラノイジン、フラ
ボン誘導体、BHTなどを粉末ミルクの場合、0.0001〜0.1
%、液体ミルクの場合0.00001〜0.01%程度添加するこ
とが好ましい。又、酸化防止剤としてはこれらに限らず
一般に知られているものを全て使用することができる。
In the artificial milk of the present invention, if necessary, to prevent oxidation, tocopherol, sesamol, melanoidin, flavone derivative, BHT and the like in the case of powdered milk, 0.0001 to 0.1
%, In the case of liquid milk, it is preferable to add about 0.00001 to 0.01%. The antioxidants are not limited to these, and any generally known antioxidants can be used.

次に、実施例により、この発明をさらに具体的に説明
する。
Next, the present invention will be described more specifically with reference to examples.

実施例1. β−シクロデキストリン2gを20%エタノール水溶液20
mlに添加し、ここにスターラーで攪拌しながら、EDA100
mgを加え、50℃に2時間インキュベートした。室温冷却
(約1時間)後、さらに攪拌を続けながら4℃に10時間
インキュベートした。生成した沈殿を、遠心分離により
回収し、n−ヘキサンで洗浄後、凍結乾燥を行ない、ED
A5%含有シクロデキストリン包接化合物1.8gを得た。こ
の粉末1gを粉末ミルク1kgに混ぜ合わせ、均質なEDA含有
ミルクを調製した。
Example 1. 2 g of β-cyclodextrin was added to a 20% aqueous ethanol solution 20
Add EDA 100 ml while stirring with a stirrer.
mg was added and incubated at 50 ° C. for 2 hours. After cooling at room temperature (about 1 hour), the mixture was incubated at 4 ° C. for 10 hours while continuing stirring. The resulting precipitate was collected by centrifugation, washed with n-hexane, freeze-dried, and
1.8 g of a cyclodextrin inclusion compound containing 5% of A was obtained. 1 g of this powder was mixed with 1 kg of powdered milk to prepare a homogeneous EDA-containing milk.

実施例2. DGLA、ARA、及びEPAについて実施例1と同様の操作を
行なった所、それぞれ均質なDGLA含有ミルク、ARA含有
ミルク、及びEPA含有ミルクが得られた。
Example 2 The same operation as in Example 1 was performed for DGLA, ARA, and EPA, and homogeneous DGLA-containing milk, ARA-containing milk, and EPA-containing milk were obtained, respectively.

実施例3. EDA、DGLA、ARA、及びEPAのそれぞれのエチルエステ
ルについて実施例1と同様の操作を行なった所、それぞ
れ均質なEDAエチルエステル含有ミルク、DGLAエチルエ
ステル含有ミルク、ARAエチルエステル含有ミルク、及
びEPAエチルエステル含有ミルクが得られた。
Example 3 The same operation as in Example 1 was performed for each of the ethyl esters of EDA, DGLA, ARA, and EPA, and the same milk containing EDA ethyl ester, milk containing DGLA ethyl ester, milk containing ARA ethyl ester was obtained. , And EPA ethyl ester containing milk were obtained.

実施例4. モルティエレラ・エロンガタSAM0219(FERMP−8703)
の培養菌体より得られた菌体油脂20gを無水エタノール
−塩酸(95:5)を用いて、50℃にて3時間処理すること
によってエチルエステル化し、n−ヘキサンで抽出して
15gの脂肪酸エステルを得た。このものの組成はパルミ
チン酸エチル16%、ステアリン酸エチル5%、オレイン
酸エチル27%、リノール酸エチル10%、GLAエチル4
%、EDAエチル1%、DGLAエチル7%、ARAエチル20%、
及びEPAエチル10%であった。この脂肪酸エチルエステ
ル混合物2gについて実施例1と同様の操作を行なった
所、均質な粉末ミルクが得られた。又、デキストリン包
接化合物0.1gを液体ミルク1に混ぜ合わせた所、均質
な液体ミルクが得られた。
Example 4. Mortierella elongata SAM0219 (FERMP-8703)
20 g of the cell fat obtained from the cultured cells of the above was treated with anhydrous ethanol-hydrochloric acid (95: 5) at 50 ° C. for 3 hours to be ethyl-esterified, and extracted with n-hexane.
15 g of fatty acid ester were obtained. The composition of this is 16% ethyl palmitate, 5% ethyl stearate, 27% ethyl oleate, 10% ethyl linoleate, 4% ethyl GLA
%, EDA ethyl 1%, DGLA ethyl 7%, ARA ethyl 20%,
And EPA ethyl 10%. When 2 g of this fatty acid ethyl ester mixture was subjected to the same operation as in Example 1, a homogeneous powdered milk was obtained. When 0.1 g of the dextrin clathrate compound was mixed with liquid milk 1, a homogeneous liquid milk was obtained.

実施例5. β−シクロデキストリン20gに50%エタノール水溶液5
mlを加え、60℃の恒温槽中につけた乳鉢中に入れた。こ
れにDGLAエチル2gを加え、ゆっくりと3時間、練り合ぜ
た。室温冷却(2時間)後、4℃に10時間インキュベー
トした。水1を加えて1時間インキュベートした。水
1を加えて1時間攪拌後、遠心分離により、沈殿物を
回収した。n−ヘキサンで洗浄後、凍結乾燥を行ない、
DGLA10%含有シクロデキストリン包接化合物8.5gを得
た。この粉末2gを2kgの粉末ミルク、及び150の液体ミ
ルクに混ぜ合せた所、いずれも均質なミルクが得られ
た。
Example 5 β-cyclodextrin (20 g) and 50% ethanol aqueous solution (5)
Then, the mixture was placed in a mortar placed in a thermostat at 60 ° C. To this, 2 g of DGLA ethyl was added and kneaded slowly for 3 hours. After cooling at room temperature (2 hours), the mixture was incubated at 4 ° C. for 10 hours. Water 1 was added and incubated for 1 hour. After adding water 1 and stirring for 1 hour, the precipitate was recovered by centrifugation. After washing with n-hexane, freeze-drying is performed,
8.5 g of a cyclodextrin inclusion compound containing 10% of DGLA was obtained. When 2 g of this powder was mixed with 2 kg of powdered milk and 150 liquid milks, homogeneous milk was obtained in each case.

実施例6. GLAエチル、EDAエチル、DGLAエチル、ARAエチル、EPA
エチルをそれぞれ重量比2:1:6:4:8の割合で混ぜ合わせ
た混合脂肪酸エチル2gについて、実施例5と同様の操作
を行なった所、均質な粉末ミルク及び液体ミルクが得ら
れた。
Example 6. GLA ethyl, EDA ethyl, DGLA ethyl, ARA ethyl, EPA
The same operation as in Example 5 was performed on 2 g of the mixed fatty acid ethyl obtained by mixing ethyl at a weight ratio of 2: 1: 6: 4: 8 to obtain homogeneous powdered milk and liquid milk.

───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭62−79732(JP,A) 特開 昭64−80250(JP,A) ──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-62-79732 (JP, A) JP-A-64-80250 (JP, A)

Claims (3)

(57)【特許請求の範囲】(57) [Claims] 【請求項1】エイコサジエン酸、ビスホモ−γ−リノレ
ン酸もしくはアラキドン酸、又は前記脂肪酸のエステ
ル、前記脂肪酸を含有する油脂、前記油脂の加水分解物
もしくは前記油脂分解物のエステル化物をそれぞれ単独
で又は混合して添加し、あるいは、さらにそれらのほか
にγ−リノレン酸もしくはエイコサペンタエン酸、又は
前記脂肪酸のエステル、前記脂肪酸を含有する油脂、前
記油脂の加水分解物もしくは前記油脂分解物のエステル
化物をそれぞれ単独で又は混合して添加した人工乳。
1. Eicosadienoic acid, bishomo-γ-linolenic acid or arachidonic acid, or an ester of the fatty acid, an oil or fat containing the fatty acid, a hydrolyzate of the oil or fat, or an esterified product of the oil or fat decomposed product, respectively. Mixing and adding, or, in addition to them, γ-linolenic acid or eicosapentaenoic acid, or an ester of the fatty acid, an oil or fat containing the fatty acid, a hydrolyzate of the oil or fat, or an esterified product of the oil or fat decomposition product. Artificial milk added alone or in combination.
【請求項2】前記の脂肪酸を含有する油脂として、モル
ティエレラ属に属する微生物により生産される油脂であ
ってアラキドン酸を含有するものを添加した、請求項1
に記載の人工乳。
2. An oil or fat produced by a microorganism belonging to the genus Mortierella, which contains arachidonic acid, as the oil or fat containing the fatty acid.
The artificial milk according to the above.
【請求項3】前記油脂がトリグリセライドである、請求
項1又は2に記載の人工乳。
3. The artificial milk according to claim 1, wherein the fat or oil is triglyceride.
JP63021170A 1988-02-02 1988-02-02 Artificial milk with polyunsaturated fatty acid component Expired - Lifetime JP2697834B2 (en)

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JP2697834B2 true JP2697834B2 (en) 1998-01-14

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5407957A (en) * 1990-02-13 1995-04-18 Martek Corporation Production of docosahexaenoic acid by dinoflagellates
US5013569A (en) * 1990-05-21 1991-05-07 Century Laboratories, Inc. Infant formula
US5658767A (en) * 1991-01-24 1997-08-19 Martek Corporation Arachidonic acid and methods for the production and use thereof
PH11992043811B1 (en) * 1991-01-24 2002-08-22 Martek Corp Arachidonic acid and methods for the production and use thereof
EP1092352A3 (en) * 1991-01-24 2003-08-27 Martek Corporation Microbial oil mixtures and uses thereof
JP3419897B2 (en) * 1994-07-22 2003-06-23 明治乳業株式会社 Hypoallergenic formula
US5518751A (en) * 1994-09-08 1996-05-21 Friesland Brands B.V. Process for the preparation of milk concentrates and milk powders having a long storage life
US5583019A (en) 1995-01-24 1996-12-10 Omegatech Inc. Method for production of arachidonic acid
JP3792309B2 (en) 1996-08-30 2006-07-05 サントリー株式会社 Process for producing unsaturated fatty acid-containing fats and oils
JP4633204B2 (en) * 1996-10-11 2011-02-16 サントリーホールディングス株式会社 Arachidonic acid-containing edible oil and fat and food containing the same
JP3203485B2 (en) * 1998-08-19 2001-08-27 明治乳業株式会社 Infant food composition with adjusted phospholipid and fatty acid composition
US10532065B2 (en) 2014-12-19 2020-01-14 Nagasaki University Bisphosphonic acid derivative and application for same

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6279732A (en) * 1985-10-02 1987-04-13 Agency Of Ind Science & Technol Milk containing added triglyceride containing gamma-linolenic acid
JP2525624B2 (en) * 1987-09-21 1996-08-21 雪印乳業株式会社 Baby milk powder containing polyunsaturated fatty acids

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