JP2023147529A - Composition including highly unsaturated fatty acid or ester thereof and ascorbyl long-chain saturated fatty acid ester - Google Patents
Composition including highly unsaturated fatty acid or ester thereof and ascorbyl long-chain saturated fatty acid ester Download PDFInfo
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- -1 saturated fatty acid ester Chemical class 0.000 title claims abstract description 65
- 150000002148 esters Chemical class 0.000 title claims abstract description 64
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims abstract description 51
- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims abstract description 49
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 title abstract description 4
- 229940106134 krill oil Drugs 0.000 claims abstract description 19
- 238000001556 precipitation Methods 0.000 claims abstract description 17
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 17
- 235000021281 monounsaturated fatty acids Nutrition 0.000 claims abstract description 16
- 230000003647 oxidation Effects 0.000 claims abstract description 15
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 15
- 235000013871 bee wax Nutrition 0.000 claims abstract description 14
- 239000012166 beeswax Substances 0.000 claims abstract description 14
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 64
- 229960005070 ascorbic acid Drugs 0.000 claims description 33
- 235000010323 ascorbic acid Nutrition 0.000 claims description 32
- 239000011668 ascorbic acid Substances 0.000 claims description 32
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 20
- 229930195729 fatty acid Natural products 0.000 claims description 20
- 239000000194 fatty acid Substances 0.000 claims description 20
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 16
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
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- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims description 9
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 9
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 9
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 9
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 9
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 7
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- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 2
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- 239000002253 acid Substances 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 2
- BYNVYIUJKRRNNC-UHFFFAOYSA-N docosanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCCCCCC(O)=O BYNVYIUJKRRNNC-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- 235000003441 saturated fatty acids Nutrition 0.000 description 2
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- PBTPTBMYJPCXRQ-MGMRMFRLSA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;hexadecanoic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O.CCCCCCCCCCCCCCCC(O)=O PBTPTBMYJPCXRQ-MGMRMFRLSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
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- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 239000004261 Ascorbyl stearate Substances 0.000 description 1
- LITUBCVUXPBCGA-WMZHIEFXSA-N Ascorbyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O LITUBCVUXPBCGA-WMZHIEFXSA-N 0.000 description 1
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- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Natural products OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
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- Coloring Foods And Improving Nutritive Qualities (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Edible Oils And Fats (AREA)
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Abstract
Description
本発明は、高度不飽和脂肪酸又はそのエステルとアスコルビン酸長鎖飽和脂肪酸エステルを含有する組成物に関する。
詳細には、高度不飽和脂肪酸又はそのエステルとアスコルビン酸長鎖飽和脂肪酸エステルに加え、さらにクリルオイル及び／又はミツロウ及び／又は飽和又は一価不飽和脂肪酸エステルを含有する組成物に関する。
The present invention relates to a composition containing a highly unsaturated fatty acid or its ester and an ascorbic acid long chain saturated fatty acid ester.
Specifically, the present invention relates to a composition containing, in addition to highly unsaturated fatty acids or esters thereof and ascorbic acid long-chain saturated fatty acid esters, krill oil and/or beeswax and/or saturated or monounsaturated fatty acid esters.
魚油中などに含有されている高度不飽和脂肪酸及びそのエステルは、医学上又は栄養学上極めて重要な物質であることが知られている。例えば、魚油中の高度不飽和脂肪酸であるエイコサペンタエン酸（ＥＰＡ）は、血液中の中性脂肪およびコレステロール低下作用、血栓の抑制効果を有することから、心筋梗塞、脳梗塞、動脈硬化等の予防、治療等に有効であり、又、ドコサヘキサエン酸（ＤＨＡ）は、学習機能の向上、抗腫瘍、抗アレルギー等の優れた効果を有することが知られている。さらに、ＥＰＡ又はＤＨＡはアトピー性等の皮膚炎に対しても有効であることが知られている。そのため、ＥＰＡ、ＤＨＡ等の高度不飽和脂肪酸は、その広範な有効性から、食品、健康食品、医薬品として市販されている。 It is known that highly unsaturated fatty acids and their esters contained in fish oil and the like are extremely important substances from a medical or nutritional point of view. For example, eicosapentaenoic acid (EPA), a highly unsaturated fatty acid found in fish oil, has the effect of lowering neutral fat and cholesterol in the blood and inhibiting blood clots, thereby preventing myocardial infarction, cerebral infarction, arteriosclerosis, etc. In addition, docosahexaenoic acid (DHA) is known to have excellent effects such as improving learning function, antitumor, and antiallergy. Furthermore, EPA or DHA is known to be effective against dermatitis such as atopic dermatitis. Therefore, highly unsaturated fatty acids such as EPA and DHA are commercially available as foods, health foods, and medicines due to their wide range of effectiveness.
しかしながら、高度不飽和脂肪酸又はそのエステルはその不飽和結合部分が酸化されやすいという欠点を有しており、酸素・熱・光等により容易に酸化を受け、酸化されると魚のような異味異臭を発生し、健康への悪影響も懸念される過酸化物質が生成する。 However, highly unsaturated fatty acids or their esters have the disadvantage that their unsaturated bond parts are easily oxidized, and they are easily oxidized by oxygen, heat, light, etc., and when oxidized, they produce a fishy, off-flavor taste. This results in the production of peroxide substances, which may have negative health effects.
このような高度不飽和脂肪酸又はそのエステルの酸化を防止するために、アスコルビン酸パルミチン酸エステルを添加することが試みられている。しかし、アスコルビン酸パルミチン酸エステルは油脂に対する溶解度が低いため、油脂中での結晶の析出、沈殿、分離が生じ、十分な酸化抑制効果が発揮されないと同時に、外観上の不都合も生じるという問題があった。
そこで、アスコルビン酸パルミチン酸エステルの油脂中における析出、沈殿、分離を抑制する手段がいくつか報告されている。
In order to prevent the oxidation of such highly unsaturated fatty acids or their esters, attempts have been made to add ascorbic acid palmitate. However, ascorbic acid palmitate ester has a low solubility in fats and oils, so crystals precipitate, precipitate, and separate in fats and oils, resulting in insufficient oxidation-suppressing effects and problems in appearance. Ta.
Therefore, several methods have been reported for suppressing the precipitation, precipitation, and separation of ascorbyl palmitate ester in fats and oils.
例えば、特許文献１には、Ｌ－アスコルビン酸パルミチン酸エステル、ペースト状レシチンおよび中鎖脂肪酸トリグリセライドからなる製剤を油脂に溶解させる方法が開示されている。 For example, Patent Document 1 discloses a method in which a preparation consisting of L-ascorbic acid palmitate, paste lecithin, and medium-chain fatty acid triglyceride is dissolved in oil or fat.
また、特許文献２には、Ｌ－アスコルビン酸パルミチン酸エステル、ショ糖パルミチン酸エステルおよびナタネ油からなる製剤を油脂に溶解させる方法が開示されて、特許文献３には、Ｌ－アスコルビン酸脂肪酸エステル、ポリグリセリン不飽和脂肪酸エステル、ポリグリセリン縮合リシノール酸エステル、並びに油脂および／またはトコフェロールを含有する組成物が開示されている。 Further, Patent Document 2 discloses a method of dissolving a preparation consisting of L-ascorbic acid palmitate ester, sucrose palmitate ester, and rapeseed oil in fats and oils, and Patent Document 3 discloses L-ascorbic acid fatty acid ester , a polyglycerin unsaturated fatty acid ester, a polyglycerin condensed ricinoleic acid ester, and a composition containing oil and fat and/or tocopherol.
ところが、高度不飽和脂肪酸又はそのエステルとアスコルビン酸パルミチン酸エステルにレシチンを添加すると、高度不飽和脂肪酸又はそのエステルに対する酸化防止効果は認められるものの、レシチン自体が析出して、カプセル内容物の透明性が失われるという問題が生じることがわかった。また、レシチンは原料のＧＭＯ管理が必要であるため、使い勝手が悪いという難点もある。同様な現象は、アスコルビン酸パルミチン酸エステルだけでなく、アスコルビン酸長鎖飽和脂肪酸エステルを用いた場合にも観察される。 However, when lecithin is added to highly unsaturated fatty acids or their esters and ascorbic acid palmitate, although an antioxidant effect on the highly unsaturated fatty acids or their esters is observed, the lecithin itself precipitates, reducing the transparency of the capsule contents. It has been found that the problem of loss of information occurs. Furthermore, because lecithin requires GMO control of its raw materials, it is difficult to use. A similar phenomenon is observed when not only ascorbic acid palmitate ester but also ascorbic acid long chain saturated fatty acid ester is used.
アスコルビン酸長鎖飽和脂肪酸エステルは、高度不飽和脂肪酸又はそのエステルには溶解しにくく、溶解するためには、１００℃以上に加熱、撹拌する必要があるが、そうすると高度不飽和脂肪酸又はそのエステルは容易に酸化してしまうという問題がある。そのため、高度不飽和脂肪酸又はそのエステルにアスコルビン酸長鎖飽和脂肪酸エステルを溶解させる際には、できるだけ加熱、撹拌条件を温和なものに抑える必要があるが、アスコルビン酸長鎖飽和脂肪酸エステルの析出防止と高度不飽和脂肪酸又はそのエステルの十分な酸化防止を両立する手段は見出されていなかった。 Ascorbic acid long-chain saturated fatty acid esters are difficult to dissolve in polyunsaturated fatty acids or their esters, and in order to dissolve them, it is necessary to heat them to 100°C or higher and stir them. The problem is that it oxidizes easily. Therefore, when dissolving ascorbic acid long chain saturated fatty acid ester in highly unsaturated fatty acid or its ester, it is necessary to keep the heating and stirring conditions as mild as possible, but it is necessary to prevent the precipitation of ascorbic acid long chain saturated fatty acid ester. No means have been found to achieve both sufficient oxidation prevention of polyunsaturated fatty acids and their esters.
本発明の課題は、高度不飽和脂肪酸又はそのエステルの酸化抑制のためにアスコルビン酸長鎖飽和脂肪酸エステルを添加する際に、アスコルビン酸長鎖飽和脂肪酸エステルの析出、沈殿、分離が生じず、好ましい外観と十分な酸化抑制効果を両立できる組成物を得ることである。 An object of the present invention is to avoid precipitation, precipitation, and separation of ascorbic acid long-chain saturated fatty acid esters when adding ascorbic acid long-chain saturated fatty acid esters to suppress the oxidation of highly unsaturated fatty acids or their esters. The object of the present invention is to obtain a composition that can have both appearance and a sufficient oxidation-inhibiting effect.
本発明者らは、上記課題を解決するために鋭意検討を重ねた結果、高度不飽和脂肪酸又はそのエステルにアスコルビン酸長鎖飽和脂肪酸エステルを配合し、さらに、クリルオイル、ミツロウ、飽和又は一価不飽和脂肪酸エステルを添加することが有効であることを見出し、本発明を完成させた。 As a result of extensive studies in order to solve the above problems, the present inventors have blended ascorbic acid long chain saturated fatty acid ester with highly unsaturated fatty acids or their esters, and further added krill oil, beeswax, saturated or monovalent fatty acid. It was discovered that adding an unsaturated fatty acid ester was effective, and the present invention was completed.
したがって、上記の課題は、以下の組成物、カプセル製剤及び酸化抑制方法によって解決することができる。
（１）高度不飽和脂肪酸又はそのエステルと、アスコルビン酸長鎖飽和脂肪酸エステルと、クリルオイル及び／又はミツロウ及び／又は飽和又は一価不飽和脂肪酸エステルを含有する高度不飽和脂肪酸又はそのエステル含有組成物。
（２）高度不飽和脂肪酸又はそのエステルが、エイコサペンタエン酸及び／又はドコサヘキサエン酸又はそれらのエステルを含有する、（１）の組成物。
（３）アスコルビン酸長鎖飽和脂肪酸エステルに対するクリルオイル及び／又はミツロウ及び／又は飽和又は一価不飽和脂肪酸エステルの配合比が、１：１０～１０００である、（１）又は（２）の組成物。
（４）飽和又は一価不飽和脂肪酸エステルが、グリセリン脂肪酸エステルである、（１）～（３）の組成物。
（５）グリセリン脂肪酸エステルが、モノグリセリン脂肪酸エステル、ジグリセリン脂肪酸エステルから選択される1種以上である、（４）の組成物。
（６）アスコルビン酸長鎖飽和脂肪酸エステルが、アスコルビン酸パルミチン酸エステル又はアスコルビン酸ステアリン酸エステルである、（１）～（５）の組成物。
（７）アスコルビン酸長鎖飽和脂肪酸エステルが、アスコルビン酸パルミチン酸エステルである、（１）～（６）の組成物。
（８）（１）～（７）の組成物を含有するカプセル製剤。
（９）（１）～（７）の組成物を使用する高度不飽和脂肪酸又はそのエステルの酸化抑制及びアスコルビン酸長鎖飽和脂肪酸エステル析出抑制方法であって、高度不飽和脂肪酸又はそのエステルを含有する組成物に、アスコルビン酸長鎖飽和脂肪酸エステルと、クリル
オイル及び／又はミツロウ及び／又は飽和又は一価不飽和脂肪酸エステルを配合することを特徴とする、酸化抑制、析出抑制方法。
Therefore, the above-mentioned problems can be solved by the following composition, capsule formulation, and method for inhibiting oxidation.
(1) Highly unsaturated fatty acid or ester-containing composition containing highly unsaturated fatty acid or its ester, ascorbic acid long-chain saturated fatty acid ester, krill oil and/or beeswax and/or saturated or monounsaturated fatty acid ester thing.
(2) The composition of (1), wherein the highly unsaturated fatty acid or ester thereof contains eicosapentaenoic acid and/or docosahexaenoic acid or an ester thereof.
(3) The composition of (1) or (2), wherein the blending ratio of krill oil and/or beeswax and/or saturated or monounsaturated fatty acid ester to ascorbic acid long-chain saturated fatty acid ester is 1:10 to 1000. thing.
(4) The compositions of (1) to (3), wherein the saturated or monounsaturated fatty acid ester is a glycerin fatty acid ester.
(5) The composition according to (4), wherein the glycerin fatty acid ester is one or more types selected from monoglycerin fatty acid ester and diglycerin fatty acid ester.
(6) The compositions of (1) to (5), wherein the ascorbic acid long-chain saturated fatty acid ester is ascorbic acid palmitate or ascorbic acid stearate.
(7) The compositions of (1) to (6), wherein the ascorbic acid long-chain saturated fatty acid ester is ascorbic acid palmitate ester.
(8) A capsule formulation containing the compositions of (1) to (7).
(9) A method for suppressing the oxidation of a highly unsaturated fatty acid or its ester and suppressing the precipitation of ascorbic acid long chain saturated fatty acid ester using the composition of (1) to (7), which contains the highly unsaturated fatty acid or its ester. A method for inhibiting oxidation and precipitation, comprising blending an ascorbic acid long-chain saturated fatty acid ester, krill oil and/or beeswax, and/or a saturated or monounsaturated fatty acid ester into a composition.
本発明の、高度不飽和脂肪酸又はそのエステルと、アスコルビン酸長鎖飽和脂肪酸エステルと、クリルオイル及び／又はミツロウ及び／又は飽和又は一価不飽和脂肪酸エステルを含有する組成物は、高度不飽和脂肪酸又はそのエステルに対するアスコルビン酸長鎖飽和脂肪酸エステルの溶解性が向上して、すぐれた酸化抑制効果が発揮され、保存中におけるアスコルビン酸長鎖飽和脂肪酸エステルの析出、沈殿、分離などの問題が生じにくい。本発明の組成物は、様々な製剤形態で使用することができるが、内容物が見えるような透明な皮膜を用いたソフトカプセル剤において、特に有用である。 The composition of the present invention containing a highly unsaturated fatty acid or an ester thereof, an ascorbic acid long chain saturated fatty acid ester, krill oil and/or beeswax and/or a saturated or monounsaturated fatty acid ester is a highly unsaturated fatty acid. Or, the solubility of ascorbic acid long chain saturated fatty acid ester in its ester is improved, exhibiting an excellent oxidation inhibiting effect, and problems such as precipitation, precipitation, and separation of ascorbic acid long chain saturated fatty acid ester during storage are less likely to occur. . The composition of the present invention can be used in a variety of formulations, but is particularly useful in soft capsules with transparent membranes that allow the contents to be seen.
本発明の高度不飽和脂肪酸又はそのエステルを含有する組成物、カプセル製剤、酸化抑制、析出抑制方法について、以下に説明する。 The composition, capsule formulation, oxidation suppression, and precipitation suppression method containing the highly unsaturated fatty acid or its ester of the present invention will be explained below.
（高度不飽和脂肪酸）
本明細書において、高度不飽和脂肪酸又はそのエステルにおける高度不飽和脂肪酸とは、ω-６脂肪酸やω-３脂肪酸などの不飽和結合を２つ以上持つ脂肪酸をいう。高度不飽和脂肪酸の例としては、リノール酸、γ-リノレン酸やアラキドン酸、α-リノレン酸、エイコサペンタエン酸（ＥＰＡ）、ドコサヘキサエン酸（ＤＨＡ）などを挙げることができ、エイコサペンタエン酸（ＥＰＡ、２０：５ｎ－３）、ドコサヘキサエン酸（ＤＨＡ、２２：６ｎ－３）は、特に好ましいものである。
(Highly unsaturated fatty acids)
In this specification, highly unsaturated fatty acids or highly unsaturated fatty acids in their esters refer to fatty acids having two or more unsaturated bonds, such as ω-6 fatty acids and ω-3 fatty acids. Examples of highly unsaturated fatty acids include linoleic acid, γ-linolenic acid, arachidonic acid, α-linolenic acid, eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), etc. 20:5n-3) and docosahexaenoic acid (DHA, 22:6n-3) are particularly preferred.
本発明で用いる高度不飽和脂肪酸又はそのエステルの原料としては、主として天然物由来の油脂混合物であって、上述した高度不飽和脂肪酸又はそのエステルが含まれているものが挙げられる。そのような原料の例としては、魚類等の海産動物やプランクトン由来の油脂、藻類等の微生物由来の油脂などが挙げられ、中でもイワシ、ハマチ等の魚類由来の油脂が好ましい。 The raw material for the highly unsaturated fatty acid or its ester used in the present invention includes oil and fat mixtures mainly derived from natural products, which contain the above-mentioned highly unsaturated fatty acid or its ester. Examples of such raw materials include oils and fats derived from marine animals such as fish and plankton, and oils and fats derived from microorganisms such as algae, among which oils and fats derived from fish such as sardines and yellowtail are preferred.
本発明において、高度不飽和脂肪酸又はそのエステルには、高度不飽和脂肪酸の遊離脂肪酸、高度不飽和脂肪酸のエステル、特にメチルエステルやエチルエステルなどの低級アルキルエステルや高度不飽和脂肪酸のモノ、ジ若しくはトリグリセリド等が含まれ、高度不飽和脂肪酸又はそのエステルは、単独でも、混合物であってもよい。
本発明の組成物においては、高度不飽和脂肪酸又はそのエステルとして、エイコサペンタエン酸及び／又はドコサヘキサエン酸又はそのエステルを５～７０％程度含むものものが好ましく、４５～７０％程度含むものがさらに好ましい。
In the present invention, highly unsaturated fatty acids or esters thereof include free fatty acids of highly unsaturated fatty acids, esters of highly unsaturated fatty acids, especially lower alkyl esters such as methyl esters and ethyl esters, and mono-, di-, or esters of highly unsaturated fatty acids. Triglycerides and the like are included, and the highly unsaturated fatty acids or esters thereof may be used alone or in a mixture.
In the composition of the present invention, the highly unsaturated fatty acid or its ester preferably contains about 5 to 70% of eicosapentaenoic acid and/or docosahexaenoic acid or its ester, more preferably about 45 to 70%. .
本発明の高度不飽和脂肪酸又はそのエステルとしては、市販されている油脂類を用いてもよく、例えば、含有する高度不飽和脂肪酸又はそのエステルの種類や量が規格化された市販の魚油由来の油脂類などを用いることが好ましい。 As the highly unsaturated fatty acids or esters thereof of the present invention, commercially available oils and fats may be used. It is preferable to use oils and fats.
（アスコルビン酸長鎖飽和脂肪酸エステル）
本発明で用いるアスコルビン酸長鎖飽和脂肪酸エステルにおける長鎖飽和脂肪酸としては、炭素数１４～１８の長鎖飽和脂肪酸を使用することができ、具体的には、アスコルビン酸ミリスチン酸エステル、アスコルビン酸パルミチン酸エステル及びアスコルビン酸ステアリン酸エステルを挙げることができる。なかでも、アスコルビン酸パルミチン酸エステル及びアスコルビン酸ステアリン酸エステルが好ましく、アスコルビン酸パルミチン酸エステルが特に好ましい。アスコルビン酸長鎖飽和脂肪酸エステルは、高度不飽和脂肪酸又はそのエステル１００質量部に対して、好ましくは、０．０１～１質量％添加する。
(Ascorbic acid long chain saturated fatty acid ester)
As the long chain saturated fatty acid in the ascorbic acid long chain saturated fatty acid ester used in the present invention, long chain saturated fatty acids having 14 to 18 carbon atoms can be used, and specifically, ascorbic acid myristic acid ester, ascorbyl acid palmitate, Mention may be made of acid esters and ascorbic acid stearate esters. Among these, ascorbyl palmitate and ascorbyl stearate are preferred, and ascorbyl palmitate is particularly preferred. The ascorbic acid long-chain saturated fatty acid ester is preferably added in an amount of 0.01 to 1% by mass based on 100 parts by mass of the highly unsaturated fatty acid or ester thereof.
（クリルオイル）
クリルオイルは、南極オキアミから抽出される油脂成分である。クリルオイルの油脂は前記魚油と異なり、リン脂質が結合している。そのため、クリルオイルは、親水性が高く、水との混合が容易な油脂であるとされる。
(krill oil)
Krill oil is an oil component extracted from Antarctic krill. Krill oil differs from the fish oil in that it has phospholipids bound to it. Therefore, krill oil is considered to be a highly hydrophilic oil and fat that is easily mixed with water.
（飽和又は一価不飽和脂肪酸エステル）
飽和又は一価不飽和脂肪酸エステルとしては、乳化作用のあるグリセリン脂肪酸エステル、ショ糖脂肪酸エステル、レチノール脂肪酸エステル、プロピレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、ポリソルベート等を挙げることができるが、グリセリン脂肪酸エステルは特に好ましい。
グリセリン脂肪酸エステルの種類としては、例えば、モノグリセリン脂肪酸エステル、ジグリセリン脂肪酸エステルが挙げられ、特に、グリセリンモノベヘネート、ジグリセリンモノオレートが好ましい。
(Saturated or monounsaturated fatty acid ester)
Examples of saturated or monounsaturated fatty acid esters include glycerin fatty acid esters, sucrose fatty acid esters, retinol fatty acid esters, propylene glycol fatty acid esters, sorbitan fatty acid esters, and polysorbates, which have emulsifying properties. Particularly preferred.
Examples of the type of glycerin fatty acid ester include monoglycerin fatty acid ester and diglycerin fatty acid ester, with glycerin monobehenate and diglycerin monooleate being particularly preferred.
アスコルビン酸長鎖飽和脂肪酸エステルに対して、クリルオイル及び／又はミツロウ及び／又は飽和又は一価不飽和脂肪酸エステルは１：１より多く配合することが好ましく、特に好ましい配合比は、１：１０～１０００である。 It is preferable to mix more than 1:1 of krill oil and/or beeswax and/or saturated or monounsaturated fatty acid ester to ascorbic acid long-chain saturated fatty acid ester, and a particularly preferable blending ratio is 1:10 to 1:1. It is 1000.
（製造方法）
本発明の組成物の製造方法は特に限定されないが、例えば、原料を加温しながら撹拌・混合することにより製造することができる。高度不飽和脂肪酸又はそのエステルの酸化防止の観点から、加熱温度は１００℃以下が好ましい。
(Production method)
Although the method for producing the composition of the present invention is not particularly limited, it can be produced, for example, by stirring and mixing raw materials while heating them. From the viewpoint of preventing oxidation of highly unsaturated fatty acids or esters thereof, the heating temperature is preferably 100° C. or lower.
（その他成分）
本発明の組成物には、本発明の効果を妨げない範囲で、所望により、上記成分に加えて、更に、着色剤（例えば、酸化チタン、ベンガラ、タール系色素など）、香料、抗酸化剤（例えば、ビタミンＥ、アスコルビン酸など）など、油脂組成物の製造に通常使用される添加剤を配合することができる。
(Other ingredients)
The composition of the present invention may optionally contain, in addition to the above-mentioned components, a coloring agent (e.g., titanium oxide, red iron oxide, tar-based pigment, etc.), a fragrance, and an antioxidant, within a range that does not impede the effects of the present invention. (For example, vitamin E, ascorbic acid, etc.) and other additives commonly used in the production of oil and fat compositions can be blended.
（カプセル製剤化）
本発明の組成物が内包されたカプセル剤の形態としては、ソフトカプセルが好ましい。ソフトカプセル剤の製造方法としては、浸漬法、打ち抜き法、滴下法等、通常用いられる方法を特に制限なく採用できる。
(Capsule formulation)
The preferred form of capsules containing the composition of the present invention is soft capsules. As a method for producing soft capsules, commonly used methods such as a dipping method, a punching method, and a dropping method can be employed without particular limitation.
カプセルの素材は、ゼラチン又は植物由来のセルロースを変性させたセルロース誘導体を基材とすることができる。このうち、食品であるゼラチンを基材とすることが好ましい。 The capsule material can be based on gelatin or a cellulose derivative obtained by modifying cellulose derived from plants. Among these, it is preferable to use gelatin, which is a food product, as the base material.
ゼラチンとしては、特に制限はなく、目的に応じて適宜選択することができ、例えば、牛皮、豚皮、牛骨などに含まれる動物性コラーゲンに由来するもの、魚由来のゼラチンなどが挙げられる。これらの中でも、牛以外の動物由来のゼラチンが、狂牛病感染の恐れがない点で、好ましい。
セルロ－ス誘導体としては、例えば、アルキルセルロース（例えば、メチルセルロース等）、ヒドロキシアルキルセルロース（例えば、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロースなど）、ヒドロキシアルキルアルキルセルロース（例えば、ヒドロキシプロピルメチルセルロース（ＨＰＭＣ）、ヒドロキシエチルメチルセルロース、ヒドロキシエチルエチルセルロースなど）などが挙げられる。これらは、１種単独で用いてもよく、２種以上を併用してもよい。
The gelatin is not particularly limited and can be appropriately selected depending on the purpose. Examples include gelatin derived from animal collagen contained in cow skin, pig skin, cow bones, etc., and gelatin derived from fish. Among these, gelatin derived from animals other than cows is preferred since there is no risk of mad cow disease infection.
Examples of cellulose derivatives include alkylcelluloses (e.g., methylcellulose, etc.), hydroxyalkylcelluloses (e.g., hydroxyethylcellulose, hydroxypropylcellulose, etc.), hydroxyalkylalkylcelluloses (e.g., hydroxypropylmethylcellulose (HPMC), hydroxyethylmethylcellulose, etc.) , hydroxyethyl ethylcellulose, etc.). These may be used alone or in combination of two or more.
（酸化抑制評価）
本発明の高度不飽和脂肪酸又はそのエステルを含有する組成物の酸化指標は、過酸化物価（ＰＯＶ）で表すことができる。本発明の組成物は、３５℃、７５％Ｒ.Ｈ.で７日間保管後のＰＯＶ（ｍＥｑ／ｋｇ）が、好ましくは２５以下、より好ましくは２０以下、さらに好ましくは１５以下である。ＰＯＶはヨウ素滴定法（ＩＳＯ ３９６０：２００７）などによって測定することができる。
(oxidation inhibition evaluation)
The oxidation index of the composition containing the highly unsaturated fatty acid or ester thereof of the present invention can be expressed in terms of peroxide value (POV). The composition of the present invention has a POV (mEq/kg) after storage for 7 days at 35° C. and 75% R.H., preferably 25 or less, more preferably 20 or less, still more preferably 15 or less. POV can be measured by iodine titration method (ISO 3960:2007) or the like.
次に、アスコルビン酸長鎖飽和脂肪酸エステルとしてアスコルビン酸パルミチン酸エステルを用いた実施例により本発明をさらに詳細に説明するが、本発明は以下の実施例に限定されるものではない。 Next, the present invention will be explained in more detail with examples using ascorbic acid palmitate ester as the ascorbic acid long chain saturated fatty acid ester, but the present invention is not limited to the following examples.
実施例、比較例
（試料調製方法）
表に記載の各原料を１００ｇスケールでビーカーに入れ、８０℃に加温し、ホモミクサー（ＴＫ ＲＯＢＯＭＩＸ、プライミクス株式会社）で３０００ｒｐｍ 、５分間混合した。ホモミクサーを回転したまま、室温まで冷却して試料液を得た。調製した試料液は、３５℃、７５％Ｒ.Ｈ.の恒温槽に７日間保管した。
Examples, comparative examples (sample preparation method)
Each raw material listed in the table was placed in a beaker in a 100 g scale, heated to 80° C., and mixed for 5 minutes at 3000 rpm using a homomixer (TK ROBOMIX, Primix Co., Ltd.). While the homomixer was still rotating, it was cooled to room temperature to obtain a sample solution. The prepared sample solution was stored in a constant temperature bath at 35° C. and 75% R.H. for 7 days.
（原料）
・魚油（ＤＨＡ－４６Ｇ、日本水産製）
・アスコルビン酸パルミチン酸エステル（ビタミンＣパルミテート、三菱ケミカル製）
・クリルオイル（クリルオイルＩＩ、清光薬品工業製）
・ミツロウ（ビースワックスＧＢ、三木化学工業製）
・グリセリン脂肪酸エステル
：ジグリセリンモノオレート（ポエムＤＯ－１００Ｖ、理研ビタミン製）
：グリセリンモノベヘネート（ポエムＢ－１００、理研ビタミン製）
(material)
・Fish oil (DHA-46G, manufactured by Nippon Suisan)
・Ascorbic acid palmitate (vitamin C palmitate, manufactured by Mitsubishi Chemical)
・Krill oil (Krill oil II, manufactured by Seiko Pharmaceutical Industries)
・Beeswax (Beeswax GB, manufactured by Miki Chemical Industry)
・Glycerin fatty acid ester: diglycerin monooleate (Poem DO-100V, manufactured by Riken Vitamin)
: Glycerin monobehenate (Poem B-100, manufactured by Riken Vitamin)
（評価方法）
３５℃、７５％Ｒ.Ｈ.の恒温槽に７日間保管後の過酸化物価（ＰＯＶ）を電位差滴定法で測定した。ＰＯＶが２５以下を効果ありとした。
また、以下の基準で外観評価（目視／析出、沈殿、分離）を行った。
◎：沈殿や析出物がなく、澄明な液体。
〇：ごくわずかに沈殿や析出物がみられる。
×：沈殿や析出物があり、液体が濁っている。
(Evaluation method)
The peroxide value (POV) after being stored in a constant temperature bath at 35° C. and 75% R.H. for 7 days was measured by potentiometric titration. A POV of 25 or less was considered effective.
In addition, appearance evaluation (visual observation/precipitation, precipitation, separation) was performed based on the following criteria.
◎: Clear liquid with no precipitates or precipitates.
○: A very slight amount of precipitate or precipitate is observed.
×: Precipitates and precipitates are present, and the liquid is cloudy.
（結果）
表１の比較例１～３からは、高度不飽和脂肪酸又はそのエステルを含む魚油は、３５℃、７５％Ｒ.Ｈ.で７日間保管後に酸化されて高いＰＯＶ値を示し（比較例１）、アスコルビン酸パルミチン酸エステルを配合することにより一定の酸化防止効果は得られるものの十分ではなく、しかも外観評価が劣ったものになること（比較例２）、レシチンを添加すれば酸化防止効果の点では十分であるものの、外観評価は劣ったものであること（比較例３）が理解できる。 From Comparative Examples 1 to 3 in Table 1, fish oil containing highly unsaturated fatty acids or their esters was oxidized and exhibited a high POV value after being stored at 35°C and 75% R.H. for 7 days (Comparative Example 1) , Although a certain antioxidant effect can be obtained by blending ascorbyl palmitate ester, it is not sufficient and the appearance evaluation is inferior (Comparative Example 2), and adding lecithin improves the antioxidant effect. It can be seen that although this was sufficient, the appearance evaluation was poor (Comparative Example 3).
これに対して、表１の実施例１～５に示した、高度不飽和脂肪酸又はそのエステルとアスコルビン酸パルミチン酸エステルに加え、さらにクリルオイル及び／又はミツロウ及び／又は飽和又は一価不飽和脂肪酸エステルを含有する本発明の組成物では、３５℃、７５％Ｒ.Ｈ.で７日間保管後にも優れた高度不飽和脂肪酸の酸化防止効果が達成され、外観評価も好適なものであった。 On the other hand, in addition to the highly unsaturated fatty acids or their esters and ascorbic acid palmitate shown in Examples 1 to 5 in Table 1, krill oil and/or beeswax and/or saturated or monounsaturated fatty acids In the composition of the present invention containing an ester, an excellent antioxidant effect on highly unsaturated fatty acids was achieved even after storage at 35° C. and 75% R.H. for 7 days, and the appearance evaluation was also favorable.
また、表２及び表３に示すように、クリルオイルや飽和又は一価不飽和脂肪酸エステルの配合量比を変化させても、酸化防止及び外観評価の両面で十分な性能を得ることができる。 Further, as shown in Tables 2 and 3, even if the blending ratio of krill oil or saturated or monounsaturated fatty acid ester is changed, sufficient performance can be obtained in terms of both antioxidant prevention and appearance evaluation.
本発明により、高度不飽和脂肪酸又はそのエステルの酸化が防止されて、異味異臭や、過酸化物質の生成が抑制され、しかもアスコルビン酸長鎖飽和脂肪酸エステルの析出、沈殿、分離が生じない、高度不飽和脂肪酸又はそのエステル含有組成物を提供することができるので、食品、健康食品、医薬品等として、極めて利用性が高い。 The present invention prevents the oxidation of highly unsaturated fatty acids or their esters, suppresses the generation of off-flavors and peroxides, and prevents precipitation, precipitation, and separation of ascorbic acid long-chain saturated fatty acid esters. Since it can provide a composition containing unsaturated fatty acids or their esters, it has extremely high utility as foods, health foods, pharmaceuticals, etc.
Claims (9)
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| JP2022055081A JP2023147529A (en) | 2022-03-30 | 2022-03-30 | Composition including highly unsaturated fatty acid or ester thereof and ascorbyl long-chain saturated fatty acid ester |
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| JP2022055081A JP2023147529A (en) | 2022-03-30 | 2022-03-30 | Composition including highly unsaturated fatty acid or ester thereof and ascorbyl long-chain saturated fatty acid ester |
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2022
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