JP2020186359A - Conjugated fatty acid-containing oil/fat powder - Google Patents
Conjugated fatty acid-containing oil/fat powder Download PDFInfo
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 97
- 239000000194 fatty acid Substances 0.000 title claims abstract description 97
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 97
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 97
- 239000000843 powder Substances 0.000 title claims abstract description 75
- 108010073771 Soybean Proteins Proteins 0.000 claims abstract description 44
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- 230000006866 deterioration Effects 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
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- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 description 3
- 229920001353 Dextrin Polymers 0.000 description 3
- 239000004375 Dextrin Substances 0.000 description 3
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 3
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 3
- 229940108924 conjugated linoleic acid Drugs 0.000 description 3
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- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
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- 150000008163 sugars Chemical class 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000001785 acacia senegal l. willd gum Substances 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
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- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000002960 lipid emulsion Substances 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
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Abstract
Description
本発明は、共役脂肪酸含有油脂粉末及びその製造方法等に関する。 The present invention relates to a conjugated fatty acid-containing oil / fat powder and a method for producing the same.
共役二重結合をもつ共役脂肪酸は、機能性素材として注目されており、各種飲食品や医薬品、飼料等への利用が望まれている。一方で、該油脂は人体では生成できず、また一般的に安定性が低く、酸化劣化し易いことが知られている。通常、油脂を各種飲食品や医薬品、飼料等へ広く利用する場合には、粉末化することが重要となるが、油脂の粉末化では特に酸化劣化が問題となり易い。特に共役脂肪酸は通常の油脂よりも酸化され易いため、粉末化は通常の油脂よりもさらに困難なことが知られていた。 Conjugated fatty acids having a conjugated double bond are attracting attention as functional materials, and their use in various foods and drinks, pharmaceuticals, feeds, etc. is desired. On the other hand, it is known that the fats and oils cannot be produced by the human body, are generally low in stability, and are easily oxidatively deteriorated. Normally, when fats and oils are widely used in various foods and drinks, pharmaceuticals, feeds, etc., it is important to pulverize them, but oxidative deterioration is particularly likely to be a problem in powdering fats and oils. In particular, conjugated fatty acids are more easily oxidized than ordinary fats and oils, so it has been known that pulverization is even more difficult than ordinary fats and oils.
共役脂肪酸の粉末化に関して、特許文献１には、アラビアガムを用いた共役リノール酸粉末が開示されており、また、特許文献２には、澱粉であるＨＩ−ＣＡＰ１００およびＨＩ−ＣＡＰ２００から選択される賦形剤を用いた共役リノール酸粉末が開示されている。 Regarding the powdering of conjugated fatty acids, Patent Document 1 discloses conjugated linoleic acid powder using Arabic gum, and Patent Document 2 selects from starches HI-CAP100 and HI-CAP200. Conjugated linoleic acid powders using excipients are disclosed.
本発明は、共役脂肪酸含有油脂粉末及びその製造方法、並びに該組成物を使用した飲食品等を提供する。 The present invention provides a conjugated fatty acid-containing oil / fat powder, a method for producing the same, and foods and drinks using the composition.
発明者らは、共役脂肪酸の粉末化において、大豆タンパク質と糖質とを含むことで酸化され難い粉末が得られることを見出し、本発明を完成した。 The inventors have found that in the powdering of conjugated fatty acids, a powder that is difficult to be oxidized can be obtained by containing soy protein and sugar, and completed the present invention.
すなわち、本発明は、以下の［１］〜［１０］の態様に関する。
［１］共役脂肪酸、大豆タンパク質及び糖質を含む油脂粉末であって、糖質が分子量２００〜２０００であって、油脂１００重量％に対して大豆タンパク質を１０〜７５重量％含む、共役脂肪酸含有油脂粉末。
［２］油脂１００重量％に対して糖質を１０〜３００重量％含む、［１］記載の共役脂肪酸含有油脂粉末。
［３］大豆タンパク質１重量％に対して糖質を０．１５〜２０重量％含む、［１］又は［２］記載の共役脂肪酸含有油脂粉末。
［４］５０℃、５０日間保存後に酸化臭の発生が感じられない、［１］〜［３］の何れかに記載の共役脂肪酸含有油脂粉末。
［５］共役脂肪酸、大豆タンパク質及び糖質を含む油脂粉末であって、糖質が分子量２００〜２０００であって、油脂１００重量％に対して大豆タンパク質を１０〜７５重量％含む、共役脂肪酸含有油脂粉末の製造方法。
［６］油脂１００重量％に対して糖質を１０〜３００重量％含む、［５］記載の共役脂肪酸含有油脂粉末の製造方法。
［７］大豆タンパク質１重量％に対して糖質を０．１５〜２０重量％含む、［５］又は［６］記載の共役脂肪酸含有油脂粉末の製造方法。
［８］共役脂肪酸含有油脂、大豆タンパク質、糖質及び水を乳化処理した乳化液を噴霧乾燥することを特徴とする、［５］〜［７］の何れかに記載の共役脂肪酸含有油脂粉末の製造方法。
［９］乳化液中の大豆タンパク質１重量％に対して水を５〜５０重量％含む、［８］に記載の共役脂肪酸含有油脂粉末の製造方法。
［１０］［１］〜［４］記載の共役脂肪酸含有油脂粉末を含む飲食品、医薬品、医薬部外品、化粧品及び飼料。That is, the present invention relates to the following aspects [1] to [10].
[1] An oil / fat powder containing conjugated fatty acid, soy protein and sugar, which has a molecular weight of 200 to 2000 and contains 10 to 75% by weight of soy protein with respect to 100% by weight of the oil. Oil powder.
[2] The conjugated fatty acid-containing oil / fat powder according to [1], which contains 10 to 300% by weight of sugar with respect to 100% by weight of the oil / fat.
[3] The conjugated fatty acid-containing oil / fat powder according to [1] or [2], which contains 0.15 to 20% by weight of sugar with respect to 1% by weight of soybean protein.
[4] The conjugated fatty acid-containing oil / fat powder according to any one of [1] to [3], wherein no oxidative odor is felt after storage at 50 ° C. for 50 days.
[5] An oil / fat powder containing conjugated fatty acid, soybean protein and sugar, which has a molecular weight of 200 to 2000 and contains 10 to 75% by weight of soybean protein with respect to 100% by weight of the oil / fat. Method for producing fat and oil powder.
[6] The method for producing a conjugated fatty acid-containing oil / fat powder according to [5], which contains 10 to 300% by weight of sugar with respect to 100% by weight of the oil / fat.
[7] The method for producing a conjugated fatty acid-containing oil / fat powder according to [5] or [6], which contains 0.15 to 20% by weight of sugar with respect to 1% by weight of soybean protein.
[8] The conjugated fatty acid-containing oil / fat powder according to any one of [5] to [7], which comprises spray-drying an emulsion obtained by emulsifying conjugated fatty acid-containing oil / fat, soybean protein, sugar and water. Production method.
[9] The method for producing a conjugated fatty acid-containing oil / fat powder according to [8], which contains 5 to 50% by weight of water with respect to 1% by weight of soybean protein in the emulsion.
[10] Foods and drinks, pharmaceuticals, quasi-drugs, cosmetics and feeds containing the conjugated fatty acid-containing oil / fat powder according to [1] to [4].
本発明によって、酸化し易い共役脂肪酸の酸化劣化を抑え、保存性を高めた粉末、並びに該粉末を使用した飲食品を提供することができる。また、該共役脂肪酸含有油脂粉末を製造できる製造方法を提供できる。 INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a powder that suppresses oxidative deterioration of conjugated fatty acids that are easily oxidized and has improved storage stability, and foods and drinks using the powder. Further, it is possible to provide a production method capable of producing the conjugated fatty acid-containing oil / fat powder.
本発明の共役脂肪酸含有油脂粉末は、共役脂肪酸、大豆タンパク質及び糖質を含む油脂粉末である。 The conjugated fatty acid-containing oil / fat powder of the present invention is an oil / fat powder containing conjugated fatty acid, soybean protein and sugar.
本発明に用いる共役脂肪酸含有油脂は、共役脂肪酸を含有する油脂であれば特に限定されないが、共役脂肪酸含量は２０重量％以上が好ましく、３０重量％以上がより好ましく、４０重量％以上がさらに好ましく、５０〜９０重量％が特に好ましく、共役リノール酸を含む市販の油脂等を使用することができる。また、共役脂肪酸含有油脂粉末中の共役脂肪酸含量は特に限定されないが、１０〜８０重量％が好ましく、２０〜７０重量％がより好ましく、３０〜６５重量％がさらに好ましい。 The conjugated fatty acid-containing fat and oil used in the present invention is not particularly limited as long as it contains a conjugated fatty acid, but the conjugated fatty acid content is preferably 20% by weight or more, more preferably 30% by weight or more, still more preferably 40% by weight or more. , 50 to 90% by weight is particularly preferable, and commercially available fats and oils containing conjugated linoleic acid can be used. The content of the conjugated fatty acid in the conjugated fatty acid-containing oil / fat powder is not particularly limited, but is preferably 10 to 80% by weight, more preferably 20 to 70% by weight, still more preferably 30 to 65% by weight.
本発明に用いる大豆タンパク質は、乳化効果のある大豆タンパク質であれば特に限定されず、共役脂肪酸含有油脂粉末中の油脂１００重量％に対して大豆タンパク質を１０〜７５重量％、好ましくは１５〜７０重量％、より好ましくは２０〜６５重量％含む。また、共役脂肪酸１００重量％に対して大豆タンパク質を好ましくは１５〜９５重量％、より好ましくは２０〜９０重量％、さらに好ましくは３０〜８５重量％含む。これによって、共役脂肪酸の経時的な酸化劣化を抑制することができ、各種製品として利用可能な共役脂肪酸含有油脂粉末を提供することができる。 The soybean protein used in the present invention is not particularly limited as long as it is a soybean protein having an emulsifying effect, and the amount of soybean protein is 10 to 75% by weight, preferably 15 to 70% by weight, based on 100% by weight of the fat and oil in the conjugated fatty acid-containing fat and oil powder. It contains% by weight, more preferably 20 to 65% by weight. Further, the soybean protein is preferably contained in an amount of 15 to 95% by weight, more preferably 20 to 90% by weight, still more preferably 30 to 85% by weight based on 100% by weight of the conjugated fatty acid. As a result, it is possible to suppress oxidative deterioration of the conjugated fatty acid over time, and it is possible to provide a conjugated fatty acid-containing oil / fat powder that can be used as various products.
本発明に用いる糖質は、分子量２００〜２０００の糖質であれば特に限定されないが、好ましくは分子量２５０〜１５００、より好ましくは３００〜１０００で、例えば該分子量の糖類、多糖類、糖アルコール類等であって、二糖類以上の糖類、二糖以上の糖アルコール類及び澱粉分解物が好ましく、マルトース、トレハロース、マルチトール、還元水飴等が例示できる。また、共役脂肪酸含有油脂粉末中の油脂に対する糖質含量は特に限定されないが、油脂１００重量％に対して好ましくは１０〜３００重量％、より好ましくは１５〜２５０重量％、さらに好ましくは２０〜２００重量％含む。また、共役脂肪酸１００重量％に対して糖質を好ましくは１５〜５００重量％、より好ましくは２０〜４５０重量％、さらに好ましくは３０〜４００重量％含む。 The saccharide used in the present invention is not particularly limited as long as it is a saccharide having a molecular weight of 200 to 2000, but is preferably a saccharide having a molecular weight of 250 to 1500, more preferably 300 to 1000, for example, saccharides, polysaccharides and sugar alcohols having the molecular weight. Such as, saccharides of disaccharide or more, sugar alcohols of disaccharide or more, and starch decomposition products are preferable, and maltose, trehalose, martitol, reduced water candy and the like can be exemplified. The sugar content of the conjugated fatty acid-containing fat and oil powder with respect to the fat and oil is not particularly limited, but is preferably 10 to 300% by weight, more preferably 15 to 250% by weight, and further preferably 20 to 200% by weight with respect to 100% by weight of the fat and oil. Including% by weight. Further, sugar is preferably contained in an amount of 15 to 500% by weight, more preferably 20 to 450% by weight, still more preferably 30 to 400% by weight based on 100% by weight of the conjugated fatty acid.
本発明の共役脂肪酸含有油脂粉末に用いる大豆タンパク質と糖質との比率は、共役脂肪酸の酸化劣化を抑えた粉末が得られれば特に限定されないが、大豆タンパク質１重量部に対して糖質が好ましくは０．１５〜２０重量部、より好ましくは０．２０〜１５重量部、さらに好ましくは０．３０〜１０重量部である。 The ratio of the soybean protein to the sugar used in the conjugated fatty acid-containing oil / fat powder of the present invention is not particularly limited as long as a powder that suppresses oxidative deterioration of the conjugated fatty acid can be obtained, but the sugar is preferable with respect to 1 part by weight of the soybean protein. Is 0.15 to 20 parts by weight, more preferably 0.25 to 15 parts by weight, still more preferably 0.30 to 10 parts by weight.
本発明の共役脂肪酸含有油脂粉末は、共役脂肪酸含有油脂、大豆タンパク質、糖質及び水を乳化処理する工程を含み、該乳化液を乾燥することによって得られる。乳化処理液中の大豆タンパク質に対する水含量は、乳化処理ができれば特に限定されないが、大豆タンパク質１重量部に対して好ましくは５〜１００重量部、より好ましくは８〜８０重量部、さらに好ましくは１０〜６０重量部である。乾燥は、本発明の粉末が得られれば特に限定されないが、噴霧乾燥、真空乾燥及び／又は凍結乾燥等が例示でき、噴霧乾燥が好ましい。 The conjugated fatty acid-containing oil / fat powder of the present invention includes a step of emulsifying the conjugated fatty acid-containing oil / fat, soy protein, sugar and water, and is obtained by drying the emulsion. The water content of the soybean protein in the emulsification treatment solution is not particularly limited as long as the emulsification treatment can be performed, but is preferably 5 to 100 parts by weight, more preferably 8 to 80 parts by weight, still more preferably 10 parts by weight with respect to 1 part by weight of the soybean protein. ~ 60 parts by weight. The drying is not particularly limited as long as the powder of the present invention can be obtained, but spray drying, vacuum drying and / or freeze drying and the like can be exemplified, and spray drying is preferable.
本発明で行う乳化処理は、原料全体を１００重量％とした場合に、水を３０〜９５重量％含むのが好ましく、４０〜９０重量％含むのがより好ましく、５０〜８５重量％含むのがさらに好ましい。また、共役脂肪酸含有油脂を２〜５０重量％含むのが好ましく、５〜４０重量％含むのがより好ましく、１０〜３０重量％含むのがさらに好ましい。また、大豆タンパク質を０．５〜２０重量％含むのが好ましく、１〜１５重量％含むのがより好ましく、３〜１０重量％含むのがさらに好ましい。また、糖質を０．２〜４０重量％含むのが好ましく、０．５〜３５重量％含むのがより好ましく、２〜３０重量％含むのがさらに好ましい。乳化処理は、前記成分を混合し、均質化すればよく、加熱してもよく、一般的な乳化方法で行うことができる。詳細には、乳化装置を用いて行うことができ、高圧ホモジナイザー、コロイドミル、超音波乳化機、ホモミキサー、ホモディスパー等を例示でき、二種類以上の装置を組み合わせてもよい。 The emulsification treatment performed in the present invention preferably contains 30 to 95% by weight, more preferably 40 to 90% by weight, and 50 to 85% by weight, when the whole raw material is 100% by weight. More preferred. Further, the conjugated fatty acid-containing fat and oil is preferably contained in an amount of 2 to 50% by weight, more preferably 5 to 40% by weight, still more preferably 10 to 30% by weight. Further, it preferably contains 0.5 to 20% by weight of soybean protein, more preferably 1 to 15% by weight, and even more preferably 3 to 10% by weight. Further, it preferably contains 0.2 to 40% by weight of sugar, more preferably 0.5 to 35% by weight, and even more preferably 2 to 30% by weight. The emulsification treatment may be carried out by mixing the above components and homogenizing them, or by heating them, or by a general emulsification method. More specifically, it can be carried out using an emulsifying device, and examples thereof include a high-pressure homogenizer, a colloid mill, an ultrasonic emulsifying machine, a homomixer, and a homodisper, and two or more types of devices may be combined.
本発明の共役脂肪酸含有油脂粉末は、大豆タンパク質と糖質とを用いて乳化粉末とすることで、酸化し易い共役脂肪酸の経時的な酸化劣化を抑制することができ、５０℃、５０日間保存後でも酸化臭の発生が感じられない粉末である。該粉末は、好ましくは粉末化処理の影響による乳化崩壊が起こりにくく、また、５０℃、５０日間保存後の共役脂肪酸残存率が保存前の８０％以上であるのが好ましく、８５％以上であるのがより好ましく、９０％以上であるのがさらに好ましく、９５％以上であるのが特に好ましい。 By making the conjugated fatty acid-containing oil / fat powder of the present invention into an emulsified powder using soybean protein and sugar, it is possible to suppress oxidative deterioration of the easily oxidizable conjugated fatty acid over time, and store it at 50 ° C. for 50 days. It is a powder that does not give off an oxidative odor even afterwards. The powder is less likely to undergo emulsification and disintegration due to the influence of powdering treatment, and the residual ratio of conjugated fatty acids after storage at 50 ° C. for 50 days is preferably 80% or more, preferably 85% or more before storage. Is more preferable, 90% or more is further preferable, and 95% or more is particularly preferable.
本発明の共役脂肪酸含有油脂粉末は、上記のとおり、大豆タンパク質と糖質とを用いて乳化粉末とすることで、酸化し易い共役脂肪酸の酸化劣化を抑え、保存性を高めた粉末が得られ、飲料、食品、調味料、機能性食品、サプリメント等の各種飲食品、医薬品、医薬部外品、化粧品、飼料等に利用できる。添加量は特に限定されないが、好ましくは０．１〜５０％、より好ましくは０．５〜３０％、さらに好ましくは１．０〜１０％である。 As described above, the conjugated fatty acid-containing oil / fat powder of the present invention is made into an emulsified powder by using soy protein and sugar to obtain a powder having improved storage stability by suppressing oxidative deterioration of easily oxidizable conjugated fatty acids. , Beverages, foods, seasonings, functional foods, various foods and drinks such as supplements, pharmaceuticals, non-pharmaceutical products, cosmetics, feeds, etc. The amount added is not particularly limited, but is preferably 0.1 to 50%, more preferably 0.5 to 30%, and even more preferably 1.0 to 10%.
以下、実施例を示して本発明を具体的に説明するが、本発明は以下の例によって限定されるものではない。尚、本発明において、残存率以外の％は別記がない限り全て重量％である。 Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited to the following examples. In the present invention,% other than the residual ratio is all weight% unless otherwise specified.
（１．賦形剤の検討）
粉末状大豆タンパク質（フジプロ（登録商標）Ｆ、不二製油株式会社製）４９ｇ、賦形剤として各種糖質１５５ｇを水４９０ｇに分散させ、７０℃に加温した。各種糖質は次の通りで実施した。（実施例１−１）マルチトール（レシス（登録商標）、三菱商事フードテック株式会社製、平均分子量：３４４）、（実施例１−２）トレハロース（トレハ（登録商標）、株式会社林原製、分子量：３４２）、（実施例１−３）還元水飴（ＰＯ−３０、三菱商事フードテック株式会社製、平均分子量：８８５）、（比較例１−１）エリスリトール（エリスリトールＴ微粉、三菱ケミカルフーズ株式会社製、分子量：１２２）、（比較例１−２）還元水飴（ＰＯ−１０、三菱商事フードテック株式会社製、平均分子量：２３００）又は（比較例１−３）デキストリン（サンデック＃１００（登録商標）、三和澱粉工業株式会社製、平均分子量：１７０００）。共役脂肪酸含有油脂（シーエルエース（登録商標）Ｇ−８０、日清オイリオグループ株式会社製）１９６ｇを加えて７０℃で３０分間撹拌し、予備乳化を行った後、高圧ホモジナイザーで処理（４０ＭＰａ×２回）し、共役脂肪酸含有油脂乳化液を調製した。該乳化液を噴霧乾燥することによって、各共役脂肪酸含有油脂粉末（実施品１−１〜１−３、比較品１−２及び１−３）を得た。尚、比較例１−１は、粉末が得られなかった。各粉末中の配合比率、油脂に対する大豆タンパク質又は糖質の比率、及び大豆タンパク質と糖質との比率を表１に示した。(1. Examination of excipients)
49 g of powdered soybean protein (Fuji Pro (registered trademark) F, manufactured by Fuji Oil Co., Ltd.) and 155 g of various sugars as excipients were dispersed in 490 g of water and heated to 70 ° C. Various sugars were carried out as follows. (Example 1-1) Martinol (Recis (registered trademark), manufactured by Mitsubishi Corporation Food Tech Co., Ltd., average molecular weight: 344), (Example 1-2) Trehalose (treha (registered trademark), manufactured by Hayashibara Co., Ltd.) Molecular weight: 342), (Example 1-3) Reduced starch syrup (PO-30, manufactured by Mitsubishi Corporation Food Tech Co., Ltd., average molecular weight: 885), (Comparative example 1-1) Dextrin (Erythritol T fine powder, Mitsubishi Chemical Foods Co., Ltd.) Company-made, molecular weight: 122), (Comparative Example 1-2) reduced starch syrup (PO-10, manufactured by Mitsubishi Corporation Food Tech Co., Ltd., average molecular weight: 2300) or (Comparative Example 1-3) dextrin (Sandeck # 100 (registered) Trademark), manufactured by Sanwa Dextrin Industries, Ltd., average molecular weight: 17,000). Conjugated fatty acid-containing fats and oils (CLA (registered trademark) G-80, manufactured by Nisshin Oillio Group Co., Ltd.) were added, stirred at 70 ° C. for 30 minutes, pre-emulsified, and then treated with a high-pressure homogenizer (40 MPa × 2). Then, a conjugated fatty acid-containing oil and fat emulsion was prepared. By spray-drying the emulsion, each conjugated fatty acid-containing oil and fat powder (implemented products 1-1 to 1-3, comparative products 1-2 and 1-3) was obtained. In Comparative Example 1-1, no powder was obtained. Table 1 shows the blending ratio in each powder, the ratio of soybean protein or sugar to fats and oils, and the ratio of soybean protein to sugar.
［評価試験１］
（粉末表面のオイルの浸み出し量の測定）
実施品１−１〜１−３、比較品１−２及び１−３について、粉末表面のオイルの浸み出し量を測定した。前記実施品及び比較品各２０ｇ、無水硫酸マグネシウム１０ｇ及びヘキサン１００ｍＬを、２５℃、１５分間、１００ｒｐｍで振盪撹拌した後、ろ紙（ＡＤＶＡＮＴＥＣ Ｎｏ．２）を介してヘキサン層を回収し、さらにヘキサン５０ｍＬで洗浄した。続いて、エバポレーターでヘキサンを除去し、得られた油脂の重量を測定し、表面オイルとして表１に示した。[Evaluation test 1]
(Measurement of oil seepage amount on the powder surface)
The amount of oil seeping out from the powder surface was measured for the products 1-1 to 1-3 and the comparative products 1-2 and 1-3. 20 g of each of the above-mentioned product and comparative product, 10 g of anhydrous magnesium sulfate, and 100 mL of hexane were shaken and stirred at 25 ° C. for 15 minutes at 100 rpm, and then the hexane layer was recovered through a filter paper (ADVANTEC No. 2), and 50 mL of hexane was further collected. Washed with. Subsequently, hexane was removed with an evaporator, the weight of the obtained fat and oil was measured, and the surface oil was shown in Table 1.
［評価試験２］
（粉末における共役脂肪酸含量の測定）
実施品１−１〜１−３、比較品１−２及び１−３について、透明パウチに入れ、５０℃、４２日間の保存加速試験を実施し、共役脂肪酸含有量を指標として各粉末の経時変化を確認した。尚、共役脂肪酸含有量は、ガスクロマトグラフィーを用いて、以下の方法で測定した。結果を表１に示した。また、試験前後で共役脂肪酸含量に差がないものを残存率１００％として、各残存率を表１に示した。
尚、原料の共役脂肪酸含有油脂中の共役脂肪酸含量を測定し、粉末中の共役脂肪酸含量と比較したところ、粉末化による共役脂肪酸含量の減少は見られなかった。
＜ＧＣ測定条件＞
・カラム：ＤＢ−２３ ３０ｍ×０．２５ｍｍ 膜圧０．２５μｍ （Ａｇｉｌｅｎｔ Ｊ＆Ｗ製）
・注入口温度：２５０℃
・検出器温度：２５０℃
・オーブン温度：１６０℃→２２０℃（２℃／分）
・流量：１．３ｍＬ／分（ヘリウム）
・機器：ＧＣ６８５０[Evaluation test 2]
(Measurement of conjugated fatty acid content in powder)
The products 1-1 to 1-3 and the comparative products 1-2 and 1-3 were placed in a transparent pouch and subjected to a storage acceleration test at 50 ° C. for 42 days, and the time-lapse of each powder was used as an index of the conjugated fatty acid content. I confirmed the change. The conjugated fatty acid content was measured by the following method using gas chromatography. The results are shown in Table 1. Table 1 shows each residual rate, assuming that the residual rate is 100% when there is no difference in the conjugated fatty acid content before and after the test.
When the conjugated fatty acid content in the conjugated fatty acid-containing fat and oil of the raw material was measured and compared with the conjugated fatty acid content in the powder, no decrease in the conjugated fatty acid content due to powdering was observed.
<GC measurement conditions>
-Column: DB-23 30 m x 0.25 mm Membrane pressure 0.25 μm (manufactured by Agilent J & W)
・ Inlet temperature: 250 ℃
・ Detector temperature: 250 ℃
・ Oven temperature: 160 ℃ → 220 ℃ (2 ℃ / min)
・ Flow rate: 1.3 mL / min (helium)
・ Equipment: GC6850
［評価試験３］
（粉末の酸化）
実施品１−１〜１−３、比較品１−２及び１−３について、透明パウチに入れ、５０℃、５５日間の保存加速試験を実施し、試験後の粉末の酸化について、酸化臭の有無を確認した。試験後に酸化臭の発生を感じないものを「無」、酸化臭の発生を感じたものを「有」として表１に示した。[Evaluation test 3]
(Oxidation of powder)
The products 1-1 to 1-3 and the comparative products 1-2 and 1-3 were placed in a transparent pouch and subjected to a storage acceleration test at 50 ° C. for 55 days. The oxidation of the powder after the test showed an oxidative odor. The presence was confirmed. Table 1 shows those that did not feel the generation of oxidative odor after the test as "none" and those that felt the generation of oxidative odor as "yes".
実施品１−１〜１−３は、何れも５０℃、５５日間保存後の酸化臭の発生を感じなかったのに対し、比較品１−２及び１−３は、保存後に酸化臭が発生していた。また、実施品１−１〜１−３は、粉末の表面オイルが２％以下と少なく、５０℃、４２日間保存後の共役脂肪酸残存率が９６％以上と、保存後の共役脂肪酸含有量の減少がほとんどみられなかった。一方、比較品１−２及び１−３は、粉末の表面オイルが２．７％及び７．０％で、５０℃、４２日間保存後の共役脂肪酸残存率は９１％及び９４％だった。 The products 1-1 to 1-3 did not generate an oxidative odor after storage at 50 ° C. for 55 days, whereas the comparative products 1-2 and 1-3 generated an oxidative odor after storage. Was. In addition, the products 1-1 to 1-3 had a low powdered surface oil of 2% or less, a conjugated fatty acid residual rate of 96% or more after storage at 50 ° C. for 42 days, and a conjugated fatty acid content after storage. There was almost no decrease. On the other hand, in Comparative Products 1-2 and 1-3, the powdered surface oil was 2.7% and 7.0%, and the residual ratio of conjugated fatty acids after storage at 50 ° C. for 42 days was 91% and 94%.
よって、共役脂肪酸の粉末化に当たり、大豆タンパク質の他、賦形剤として、分子量が３４２〜８８５の糖質を使用することで、酸化し易い共役脂肪酸の酸化劣化を抑えた粉末が得られることが分かった。また、オイルの浸み出しがほとんど見られず、さらに、保存後の共役脂肪酸残存率も高かったことから、該分子量の糖質を使用することで、乳化が壊れ難く、かつ共役脂肪酸含量を安定に維持できる共役脂肪酸含有油脂粉末を得ることができることが分かった。 Therefore, when pulverizing the conjugated fatty acid, by using a sugar having a molecular weight of 342-885 as an excipient in addition to soy protein, it is possible to obtain a powder in which oxidative deterioration of the conjugated fatty acid, which is easily oxidized, is suppressed. Do you get it. In addition, almost no oil seepage was observed, and the residual ratio of conjugated fatty acids after storage was high. Therefore, by using a sugar having the molecular weight, emulsification is not easily broken and the content of conjugated fatty acids is stabilized. It was found that a conjugated fatty acid-containing oil and fat powder that can be maintained in the above can be obtained.
（２．大豆タンパク質含量の検討）
粉末状大豆タンパク質（フジプロＦ）及び還元麦芽糖水飴（アマルティ（登録商標）シロップ、マルチトール７５％以上、固形分７５％、三菱商事フードテック株式会社製）を水に分散させ、７０℃に加温した。粉末状大豆タンパク質、還元麦芽糖水飴及び水の重量は次の通りで実施した。（実施例２−１）５５ｇ、１６５ｇ及び５５０ｇ、（実施例２−２）１１１ｇ、９０ｇ及び１１１０ｇ、（実施例２−３）１３３ｇ、６１ｇ及び１３３０ｇ、（比較例２−１）１１ｇ、２２４ｇ及び１１０ｇ又は（比較例２−２）１７９ｇ、０ｇ及び１７９０ｇ。各々に共役脂肪酸含有油脂（シーエルエースＧ−８０）２２１ｇを加えて７０℃で３０分間撹拌し、予備乳化を行った後、高圧ホモジナイザーで処理（４０ＭＰａ×２回）し、共役脂肪酸含有油脂乳化液を調製した。該乳化液を噴霧乾燥することによって、各共役脂肪酸含有油脂粉末（実施品２−１〜２−３、比較品２−２）を得た。尚、比較例２−１は、粉末が得られなかった。各粉末中の配合比率、油脂に対する大豆タンパク質又は糖質の比率、及び大豆タンパク質と糖質との比率を表２に示した。(2. Examination of soy protein content)
Powdered soy protein (Fujipro F) and reduced maltose starch syrup (Amarti (registered trademark) syrup, maltitol 75% or more, solid content 75%, manufactured by Mitsubishi Shoji Food Tech Co., Ltd.) are dispersed in water and heated to 70 ° C. did. The weights of powdered soy protein, reduced maltose starch syrup and water were as follows. (Example 2-1) 55 g, 165 g and 550 g, (Example 2-2) 111 g, 90 g and 1110 g, (Example 2-3) 133 g, 61 g and 1330 g, (Comparative Example 2-1) 11 g, 224 g and 110 g or (Comparative Example 2-2) 179 g, 0 g and 1790 g. 221 g of conjugated fatty acid-containing fat (CLA G-80) was added to each, stirred at 70 ° C. for 30 minutes, pre-emulsified, and then treated with a high-pressure homogenizer (40 MPa x 2 times) to emulsify the conjugated fatty acid-containing fat and oil. Was prepared. By spray-drying the emulsion, each conjugated fatty acid-containing oil / fat powder (implemented product 2-1 to 2-3, comparative product 2-2) was obtained. No powder was obtained in Comparative Example 2-1. Table 2 shows the blending ratio in each powder, the ratio of soybean protein or sugar to fats and oils, and the ratio of soybean protein to sugar.
［評価試験４］
（粉末表面のオイルの浸み出し量の測定）
実施品２−１〜２−３、比較品２−２について、粉末表面のオイルの浸み出し量を測定した。前記評価試験１に記載の方法で測定し、表面オイルとして表２に示した。[Evaluation test 4]
(Measurement of oil seepage amount on the powder surface)
The amount of oil seeping out from the powder surface was measured for the product 2-1 to 2-3 and the comparative product 2-2. It was measured by the method described in Evaluation Test 1 and is shown in Table 2 as a surface oil.
［評価試験５］
（粉末における共役脂肪酸含量の測定）
実施品２−１〜２−３、比較品２−２について、透明パウチに入れ、４０℃、４４日間の保存加速試験を実施し、共役脂肪酸含有量を指標として各粉末の経時変化を確認した。尚、共役脂肪酸含有量は、ガスクロマトグラフィーを用いて、評価試験２に記載の方法で測定した。結果を表２に示した。また、試験前後で共役脂肪酸含量に差がないものを残存率１００％として、各残存率を表２に示した。さらに、共役脂肪酸含量に対する大豆タンパク質比率及び糖質比率を算出して表２に示した。
尚、原料の共役脂肪酸含有油脂中の共役脂肪酸含量を測定し、粉末中の共役脂肪酸含量と比較したところ、粉末化による共役脂肪酸含量の減少は見られなかった。[Evaluation test 5]
(Measurement of conjugated fatty acid content in powder)
The product 2-1 to 2-3 and the comparative product 2-2 were placed in a transparent pouch and subjected to a storage acceleration test at 40 ° C. for 44 days, and the change over time of each powder was confirmed using the conjugated fatty acid content as an index. .. The conjugated fatty acid content was measured by the method described in Evaluation Test 2 using gas chromatography. The results are shown in Table 2. In addition, Table 2 shows each residual rate, assuming that the residual rate is 100% when there is no difference in the conjugated fatty acid content before and after the test. Furthermore, the soybean protein ratio and the sugar ratio with respect to the conjugated fatty acid content were calculated and shown in Table 2.
When the conjugated fatty acid content in the conjugated fatty acid-containing fat and oil of the raw material was measured and compared with the conjugated fatty acid content in the powder, no decrease in the conjugated fatty acid content due to powdering was observed.
［評価試験６］
（粉末の酸化）
実施品２−１〜２−３、比較品２−２について、透明パウチに入れ、５０℃、５１日間の保存加速試験を実施し、試験後の粉末の酸化について、酸化臭の有無を確認した。試験後に酸化臭の発生を感じないものを「無」、酸化臭の発生を感じたものを「有」として表２に示した。[Evaluation test 6]
(Oxidation of powder)
The product 2-1 to 2-3 and the comparative product 2-2 were placed in a transparent pouch and subjected to a storage acceleration test at 50 ° C. for 51 days, and the presence or absence of an oxidizing odor was confirmed for the oxidation of the powder after the test. .. Table 2 shows those who did not feel the generation of oxidative odor after the test as "none" and those who felt the generation of oxidative odor as "yes".
実施品２−１〜２−３は、何れも５０℃、５１日間保存後の酸化臭の発生を感じなかったのに対し、比較品２−２は、保存後に酸化臭が発生していた。また、実施品２−１〜２−３は、４０℃、４４日間保存後の共役脂肪酸残存率が９７％以上と、保存後の共役脂肪酸含有量の減少がほとんどみられず、実施品２−２は、粉末の表面オイルが２．１％と少なかった。一方、比較品２−２は、粉末の表面オイルが２０％で、４０℃、４４日間保存後の共役脂肪酸残存率は９６％だった。 In each of the products 2-1 to 2-3, no oxidative odor was generated after storage at 50 ° C. for 51 days, whereas in the comparative product 2-2, an oxidative odor was generated after storage. Further, in the product 2-1 to 2-3, the residual ratio of the conjugated fatty acid after storage at 40 ° C. for 44 days was 97% or more, and the content of the conjugated fatty acid after storage was hardly reduced. In No. 2, the powdered surface oil was as low as 2.1%. On the other hand, Comparative Product 2-2 had a powdered surface oil of 20% and a conjugated fatty acid residual rate of 96% after storage at 40 ° C. for 44 days.
よって、共役脂肪酸の粉末化に当たり、油脂１００％に対して大豆タンパク質を２５〜６０％、共役脂肪酸１００％に対して大豆タンパク質を３４〜７９％使用することで、酸化し易い共役脂肪酸の酸化劣化を抑えた粉末が得られることが分かった。また、保存後の共役脂肪酸残存率も高かったことから、該比率で大豆タンパク質を使用することで、共役脂肪酸含量を安定に維持できる共役脂肪酸含有油脂粉末を得ることができることが分かった。 Therefore, when pulverizing the conjugated fatty acid, by using 25 to 60% of soy protein with respect to 100% of fat and oil and 34 to 79% of soy protein with respect to 100% of the conjugated fatty acid, oxidative deterioration of the conjugated fatty acid that is easily oxidized is deteriorated. It was found that a powder containing less fatty acid was obtained. In addition, since the residual ratio of conjugated fatty acids after storage was also high, it was found that by using soybean protein at this ratio, a conjugated fatty acid-containing fat and oil powder capable of stably maintaining the conjugated fatty acid content can be obtained.
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|---|---|---|---|---|
| JPH06172782A (en) * | 1992-12-10 | 1994-06-21 | Ikeda Shiyokuken Kk | Powder of fat and oil containing highly unsaturated fatty acid |
| JP2002188095A (en) * | 2000-12-21 | 2002-07-05 | Fancl Corp | Vegetable oil and fat powder and food composition containing the powder |
| JP2004513980A (en) * | 2000-04-18 | 2004-05-13 | ナチュラル アーエス | Conjugated linoleic acid powder |
| JP2014501530A (en) * | 2010-12-22 | 2014-01-23 | アボット・ラボラトリーズ | Nutritional supplements containing calcium beta-hydroxy-betamethylbutyrate and conjugated linoleic acid |
| JP2019059684A (en) * | 2017-09-26 | 2019-04-18 | 日油株式会社 | Liquid oil powder for tableting and tablet thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06172782A (en) * | 1992-12-10 | 1994-06-21 | Ikeda Shiyokuken Kk | Powder of fat and oil containing highly unsaturated fatty acid |
| JP2004513980A (en) * | 2000-04-18 | 2004-05-13 | ナチュラル アーエス | Conjugated linoleic acid powder |
| JP2002188095A (en) * | 2000-12-21 | 2002-07-05 | Fancl Corp | Vegetable oil and fat powder and food composition containing the powder |
| JP2014501530A (en) * | 2010-12-22 | 2014-01-23 | アボット・ラボラトリーズ | Nutritional supplements containing calcium beta-hydroxy-betamethylbutyrate and conjugated linoleic acid |
| JP2019059684A (en) * | 2017-09-26 | 2019-04-18 | 日油株式会社 | Liquid oil powder for tableting and tablet thereof |
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