JP2018502085A - ω−3系多価不飽和脂肪酸を含む組成物の安定性を向上させる方法 - Google Patents
ω−3系多価不飽和脂肪酸を含む組成物の安定性を向上させる方法 Download PDFInfo
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- JP2018502085A JP2018502085A JP2017533769A JP2017533769A JP2018502085A JP 2018502085 A JP2018502085 A JP 2018502085A JP 2017533769 A JP2017533769 A JP 2017533769A JP 2017533769 A JP2017533769 A JP 2017533769A JP 2018502085 A JP2018502085 A JP 2018502085A
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- lysine
- polyunsaturated fatty
- fatty acid
- acid
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Abstract
Description
・酸化防止剤の添加、
・マイクロカプセル化、
・MA包装。
(i)少なくとも1つのω−3系多価不飽和脂肪酸成分を含む出発組成物を調製する工程と、
(ii)リジン組成物を調製する工程と、
(iii)出発組成物およびリジン組成物の水溶液、水−アルコール溶液、またはアルコール溶液を混合し、次に、結果として生じた混合物を噴霧乾燥条件下に置いて、リジン由来の陽イオンとω−3系多価不飽和脂肪酸由来の陰イオンからなる少なくとも1つの塩を含む固体生成物組成物を生成する工程と、を有し、その生成物組成物は、SC<5wt%、SC<3wt%、SC<1wt%、およびSC<0.5wt%から選択される溶剤含有量SCを呈する方法により、ω−3系多価不飽和脂肪酸を含む組成物を酸化に対して安定させることができることが分かっている。
エイコサトリエン酸(ETE)20:3(n−3)(all−cis−11,14,17−エイコサトリエン酸)、エイコサテトラエン酸(ETA)20:4(n−3)(all−cis−8,11,14,17−エイコサテトラエン酸)、ヘネイコサペンタエン酸(HPA)21:5(n−3)(all−cis−6,9,12,15,18−ヘネイコサペンタエン酸)、ドコサペンタエン酸(イワシ酸)(DPA)22:5(n−3)(all−cis−7,10,13,16,19−ドコサペンタエン酸)、テトラコサペンタエン酸24:5(n−3)(all−cis−9,12,15,18,21−テトラコサペンタエン酸)、テトラコサヘキサエン酸(ニシン酸)24:6(n−3)(all−cis−6,9,12,15,18,21−テトラコサヘキサエン酸)。
エイコサジエン酸20:2(n−6)(all−cis−11,14−エイコサジエン酸)、ジホモ−γ−リノレン酸(DGLA)20:3(n−6)(all−cis−8,11,14−エイコサトリエン酸)、ドコサジエン酸22:2(n−6)(all−cis−13,16−ドコサジエン酸)、アドレン酸22:4(n−6)(all−cis−7,10,13,16−ドコサテトラエン酸)、ドコサペンタエン酸(オズボンド酸)22:5(n−6)(all−cis−4,7,10,13,16−ドコサペンタエン酸)、テトラコサテトラエン酸24:4(n−6)(all−cis−9,12,15,18−テトラコサテトラエン酸)、テトラコサペンタエン酸24:5(n−6)(all−cis−6,9,12,15,18−テトラコサペンタエン酸)。
試薬および溶液:
1.酢酸−クロロホルム溶液(7.2mlの酢酸と4.8mlのクロロホルム)。
2.飽和ヨウ化カリウム溶液。暗所に保管すること。
3.チオ硫酸ナトリウム溶液、0.1N。市販されている。
4.1%デンプン溶液。市販されている。
5.蒸留水または脱イオン水。
試薬の空試験を実施する。
1.100mlのガラス栓付きエルレンマイヤーフラスコに、2.00(±0.02)gの試料を入れて秤量する。重量を0.01g単位で記録する。
2.メスシリンダーを用いて、12mlの酢酸−クロロホルム溶液を添加する。
3.試料が完全に溶解するまで、フラスコ内をかき混ぜる(ホットプレート上で注意深く温めることが必要な可能性もある)。
4.1mlのモールピペットを用いて、0.2mlの飽和ヨウ化カリウム溶液を添加する。
5.フラスコに栓をし、正確に1分間、フラスコの内容物をかき混ぜる。
6.その直後に、メスシリンダーを用いて12mlの蒸留水または脱イオン水を添加し、栓をして勢いよく振り混ぜて、ヨウ素をクロロホルム層から遊離させる。
7.ビュレットに0.1Nチオ硫酸ナトリウムを充填する。
8.溶液の最初の色が深い赤みがかったオレンジ色である場合、明るい色になるまで混ぜながらゆっくりと滴定する。溶液が最初から明るい琥珀色である場合は、工程9に進む。
9.分注装置を用いて、指示薬として1mlのデンプン溶液を添加する。
10.水溶液(上層)において青みがかった灰色が消えるまで滴定する。
11.使用された滴定剤の滴定量(mls)を小数第2位まで正確に記録する。
計算:
S=試料の滴定
B=空試験の滴定
過酸化物価=(S−B)×Nチオ硫酸塩×1000/試料の重量
アニシジン価は、光学濃度の100倍と定義され、光学濃度は、溶剤と試薬との混合物100ml中の1gの被検物を含有する溶液を含む1cmセルにおいて下記の方法に従って測定される。できるだけ迅速に作業を実施し、活性光線被曝を回避する。
AV=(25×(1.2×A1−A2))/m
A1=350nmでの試験液(b)の吸光度
A2=350nmでの試験液(a)の吸光度
m=試験液(a)中の被検物の質量(グラム)
・0.90<R<1.10、x(fe)=5;PC=25;SC<1wt%
・0.90<R<1.10、x(fe)=3;PC=25;SC<1wt%
・0.90<R<1.10、x(fe)=2;PC=25;SC<1wt%
・0.90<R<1.10、x(fe)=1;PC=25;SC<1wt%
・0.95<R<1.05、x(fe)=5;PC=25;SC<1wt%
・0.95<R<1.05、x(fe)=3;PC=25;SC<1wt%
・0.95<R<1.05、x(fe)=2;PC=25;SC<1wt%
・0.95<R<1.05、x(fe)=1;PC=25;SC<1wt%
・0.98<R<1.02、x(fe)=5;PC=25;SC<1wt%
・0.98<R<1.02、x(fe)=3;PC=25;SC<1wt%
・0.98<R<1.02、x(fe)=2;PC=25;SC<1wt%
・0.98<R<1.02、x(fe)=1;PC=25;SC<1wt%
・0.90<R<1.10、x(fe)=5;PC=50;SC<1wt%
・0.90<R<1.10、x(fe)=3;PC=50;SC<1wt%
・0.90<R<1.10、x(fe)=2;PC=50;SC<1wt%
・0.90<R<1.10、x(fe)=1;PC=50;SC<1wt%
・0.95<R<1.05、x(fe)=5;PC=50;SC<1wt%
・0.95<R<1.05、x(fe)=3;PC=50;SC<1wt%
・0.95<R<1.05、x(fe)=2;PC=50;SC<1wt%
・0.95<R<1.05、x(fe)=1;PC=50;SC<1wt%
・0.98<R<1.02、x(fe)=5;PC=50;SC<1wt%
・0.98<R<1.02、x(fe)=3;PC=50;SC<1wt%
・0.98<R<1.02、x(fe)=2;PC=50;SC<1wt%
・0.98<R<1.02、x(fe)=1;PC=50;SC<1wt%
・0.90<R<1.10、x(fe)=5;PC=75;SC<1wt%
・0.90<R<1.10、x(fe)=3;PC=75;SC<1wt%
・0.90<R<1.10、x(fe)=2;PC=75;SC<1wt%
・0.90<R<1.10、x(fe)=1;PC=75;SC<1wt%
・0.95<R<1.05、x(fe)=5;PC=75;SC<1wt%
・0.95<R<1.05、x(fe)=3;PC=75;SC<1wt%
・0.95<R<1.05、x(fe)=2;PC=75;SC<1wt%
・0.95<R<1.05、x(fe)=1;PC=75;SC<1wt%
・0.98<R<1.02、x(fe)=5;PC=75;SC<1wt%
・0.98<R<1.02、x(fe)=3;PC=75;SC<1wt%
・0.98<R<1.02、x(fe)=2;PC=75;SC<1wt%
・0.98<R<1.02、x(fe)=1;PC=75;SC<1wt%
・0.90<R<1.10、x(fe)=5;PC=90;SC<1wt%
・0.90<R<1.10、x(fe)=3;PC=90;SC<1wt%
・0.90<R<1.10、x(fe)=2;PC=90;SC<1wt%
・0.90<R<1.10、x(fe)=1;PC=90;SC<1wt%
・0.95<R<1.05、x(fe)=5;PC=90;SC<1wt%
・0.95<R<1.05、x(fe)=3;PC=90;SC<1wt%
・0.95<R<1.05、x(fe)=2;PC=90;SC<1wt%
・0.95<R<1.05、x(fe)=1;PC=90;SC<1wt%
・0.98<R<1.02、x(fe)=5;PC=90;SC<1wt%
・0.98<R<1.02、x(fe)=3;PC=90;SC<1wt%
・0.98<R<1.02、x(fe)=2;PC=90;SC<1wt%
・0.98<R<1.02、x(fe)=1;PC=90;SC<1wt%
本明細書に記載されるように工程(iii)において噴霧乾燥を利用する本発明の方法によって得られる好ましい組成物は、以下の選択肢のうちの1つにより特徴づけられる。
・0.90<R<1.10、x(fe)=1、SC<3wt%、sp=90
・0.90<R<1.10、x(fe)=1、SC<3wt%、sp=95
・0.90<R<1.10、x(fe)=3、SC<3wt%、sp=90
・0.90<R<1.10、x(fe)=3、SC<3wt%、sp=95
・0.95<R<1.05、x(fe)=1、SC<3wt%、sp=90
・0.95<R<1.05、x(fe)=1、SC<3wt%、sp=95
・0.95<R<1.05、x(fe)=3、SC<3wt%、sp=90
・0.95<R<1.05、x(fe)=3、SC<3wt%、sp=95
・0.98<R<1.02、x(fe)=1、SC<3wt%、sp=95
・0.98<R<1.02、x(fe)=1、SC<3wt%、sp=97
・0.98<R<1.02、x(fe)=3、SC<3wt%、sp=95
・0.98<R<1.02、x(fe)=3、SC<3wt%、sp=97
・0.90<R<1.10、x(fe)=1、SC<1wt%、sp=90
・0.90<R<1.10、x(fe)=1、SC<1wt%、sp=95
・0.90<R<1.10、x(fe)=3、SC<1wt%、sp=90
・0.90<R<1.10、x(fe)=3、SC<1wt%、sp=95
・0.95<R<1.05、x(fe)=1、SC<1wt%、sp=90
・0.95<R<1.05、x(fe)=1、SC<1wt%、sp=95
・0.95<R<1.05、x(fe)=3、SC<1wt%、sp=90
・0.95<R<1.05、x(fe)=3、SC<1wt%、sp=95
・0.98<R<1.02、x(fe)=1、SC<1wt%、sp=95
・0.98<R<1.02、x(fe)=1、SC<1wt%、sp=97
・0.98<R<1.02、x(fe)=3、SC<1wt%、sp=95
・0.98<R<1.02、x(fe)=3、SC<1wt%、sp=97
・0.90<R<1.10、x(fe)=1、SC<0.5wt%、sp=90
・0.90<R<1.10、x(fe)=1、SC<0.5wt%、sp=95
・0.90<R<1.10、x(fe)=3、SC<0.5wt%、sp=90
・0.90<R<1.10、x(fe)=3、SC<0.5wt%、sp=95
・0.95<R<1.05、x(fe)=1、SC<0.5wt%、sp=90
・0.95<R<1.05、x(fe)=1、SC<0.5wt%、sp=95
・0.95<R<1.05、x(fe)=3、SC<0.5wt%、sp=90
・0.95<R<1.05、x(fe)=3、SC<0.5wt%、sp=95
・0.98<R<1.02、x(fe)=1、SC<0.5wt%、sp=95
・0.98<R<1.02、x(fe)=1、SC<0.5wt%、sp=97
・0.98<R<1.02、x(fe)=3、SC<0.5wt%、sp=95
・0.98<R<1.02、x(fe)=3、SC<0.5wt%、sp=97
実験例
分析方法:
実験例1:エイコサペンタエン酸エチルエステル(EPA−OEt)から得られるエイコサペンタエン酸(EPA)
実験例2:ドコサヘキサエン酸エチルエステル(DHA−OEt)から得られるドコサヘキサエン酸(DHA)
実験例3:エイコサペンタエン酸(EPA)およびL−リジン(L−Lys)から得られるエイコサペンタエン酸−L−リジン塩(EPA−Lys)
実験例4:ドコサヘキサエン酸(DHA)およびL−リジン(L−Lys)から得られるドコサヘキサエン酸−L−リジン塩(DHA−Lys)
実験例5:エイコサペンタエン酸(EPA)およびNaOHから得られるエイコサペンタエン酸ナトリウム塩(EPA−Na)
実験例6:ドコサヘキサエン酸(DHA)およびNaOHから得られるドコサヘキサエン酸ナトリウム塩(DHA−Na)
実験例7:高温(50℃)かつ空気に曝露させた状態での保管に関する、PUFAおよびその誘導体の安定性についての検討
Claims (8)
- ω−3系多価不飽和脂肪酸を含む組成物の酸化安定性を向上させる方法であって、前記方法は、
(i)少なくとも1つのω−3系多価不飽和脂肪酸成分を含む出発組成物を調製する工程と、
(ii)リジン組成物を調製する工程と、
(iii)出発組成物およびリジン組成物の水溶液、水−アルコール溶液、またはアルコール溶液を混合し、続いて、結果として生じた混合物を噴霧乾燥条件下に置いて、リジン由来の陽イオンとω−3系多価不飽和脂肪酸由来の陰イオンとからなる少なくとも1つの塩を含む固体生成物組成物を生成する工程と、を有し、前記生成物組成物は、SC<5wt%、SC<3wt%、SC<1wt%、およびSC<0.5wt%から選択される溶剤含有量SCを呈する方法。 - 工程(i)で調製する前記出発組成物のカルボン酸官能基量n(ca)と工程(ii)で調製する前記リジン組成物のリジン量n(lys)との比R=n(ca)/n(lys)が、0.9<R<1.1、0.95<R<1.05、および、0.98<R<1.02から選択される範囲にあるようにして、工程(ii)におけるリジン組成物を調製することを特徴とする、請求項1に記載の方法。
- 工程(i)で調製する前記出発組成物は、x(fe)wt%以下の脂肪酸エステルを含み、x(fe)は、5、3、1、0.3、および0から選択されることを特徴とする、請求項1〜2のいずれか一項に記載の方法。
- 前記生成物組成物の少なくともspwt%が、リジン由来の陽イオンならびに1つ以上のω−3系多価不飽和脂肪酸および他の天然脂肪酸由来の陰イオンからなる1つ以上の塩からなり、spは、90、95、97、98、99、および100から選択されるようにして、工程(i)における出発組成物と工程(ii)におけるリジン組成物とを調製することを特徴とする、請求項1〜3のいずれか一項に記載の方法。
- 請求項1〜4のいずれか一項に記載の方法によって得ることができる組成物。
- ω−3系多価不飽和脂肪酸を含む食品を製造するための、請求項5に記載の組成物の使用。
- ω−3系多価不飽和脂肪酸を含む栄養製品を製造するための、請求項5に記載の組成物の使用。
- ω−3系多価不飽和脂肪酸を含む医薬品を製造するための、請求項5に記載の組成物の使用。
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