JPS6312697A - Modification inhibitor of tocoherol - Google Patents
Modification inhibitor of tocoherolInfo
- Publication number
- JPS6312697A JPS6312697A JP15506986A JP15506986A JPS6312697A JP S6312697 A JPS6312697 A JP S6312697A JP 15506986 A JP15506986 A JP 15506986A JP 15506986 A JP15506986 A JP 15506986A JP S6312697 A JPS6312697 A JP S6312697A
- Authority
- JP
- Japan
- Prior art keywords
- oil
- tocopherol
- water
- tocoherol
- phytic acid
- 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.)
- Pending
Links
- 239000003112 inhibitor Substances 0.000 title claims description 6
- 230000004048 modification Effects 0.000 title 1
- 238000012986 modification Methods 0.000 title 1
- 239000012071 phase Substances 0.000 claims description 12
- 239000011732 tocopherol Substances 0.000 claims description 12
- 229930003799 tocopherol Natural products 0.000 claims description 11
- 229940068041 phytic acid Drugs 0.000 claims description 10
- 239000000467 phytic acid Substances 0.000 claims description 10
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 claims description 9
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 claims description 9
- 235000002949 phytic acid Nutrition 0.000 claims description 9
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 9
- 230000036425 denaturation Effects 0.000 claims description 8
- 238000004925 denaturation Methods 0.000 claims description 8
- 229960001295 tocopherol Drugs 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 7
- 235000010384 tocopherol Nutrition 0.000 claims description 7
- 239000003995 emulsifying agent Substances 0.000 claims description 6
- 230000001804 emulsifying effect Effects 0.000 claims 1
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 235000019149 tocopherols Nutrition 0.000 description 4
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- -1 glycerin fatty acid Chemical class 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 229940064063 alpha tocotrienol Drugs 0.000 description 2
- RZFHLOLGZPDCHJ-DLQZEEBKSA-N alpha-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)(C)CCc2c1C RZFHLOLGZPDCHJ-DLQZEEBKSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000021323 fish oil Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229940074391 gallic acid Drugs 0.000 description 2
- 235000004515 gallic acid Nutrition 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000011731 tocotrienol Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- RZFHLOLGZPDCHJ-XZXLULOTSA-N α-Tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C RZFHLOLGZPDCHJ-XZXLULOTSA-N 0.000 description 2
- 239000011730 α-tocotrienol Substances 0.000 description 2
- 235000019145 α-tocotrienol Nutrition 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 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 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- PPWHTZKZQNXVAE-UHFFFAOYSA-N Tetracaine hydrochloride Chemical compound Cl.CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 PPWHTZKZQNXVAE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- ICJBPZBRDLONIF-UHFFFAOYSA-N hexane-1,1,1,2,2,3-hexol Chemical compound CCCC(O)C(O)(O)C(O)(O)O ICJBPZBRDLONIF-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、油相に分散しやすい、トコ７エーールの変性
防止剤に関し、更に詳細には、油脂中のトコ７エｐ−ル
の変性防止に有効な製剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a denaturation inhibitor for toco-7 ale that is easily dispersed in an oil phase, and more particularly, to a denaturation inhibitor for toco-7 ale in fats and oils. Concerning formulations effective for prevention.
トコフェロールは生体内及び生体外において、優れた抗
酸化剤として知られている。ところが、酸化を防止する
過稚でラジカルになった後に％重合、分解などくより変
性し、多くの場合に不活比となってしまう。従来、トコ
フェロールの保護物質としてはＬ−７スコルビン酸など
の還元作用な持つものが用いられている。（特開昭５１
−７９７４６号公報）
〔発明が解決しようとする問題点〕
上記のし一７スコルビン酸はある穆度効果は認められて
いるが、特に魚油なと高度不胞和酸を多く含む油脂中の
トコフェロールの変性な防とする効果はあまり認められ
ない。Tocopherol is known as an excellent antioxidant both in vivo and in vitro. However, after becoming radicals due to excessive oxidation prevention, they are denatured through polymerization, decomposition, etc., and in many cases become inactive. Conventionally, substances having a reducing effect such as L-7 scorbic acid have been used as protective substances for tocopherol. (Unexamined Japanese Patent Publication No. 51
-79746 Publication) [Problems to be Solved by the Invention] The above-mentioned scorbic acid has been recognized to have a certain virility effect, but especially fish oil, which contains tocopherols in fats and oils containing a large amount of highly unsulfated acids. It is not very effective in preventing degeneration.
本発明は、モノエン、ジエンな多く含む一般の植物油及
び陸上動物油中のトコフェロールばかりでなく、高度不
飽和脂肪酸を多ｊｌＫ含む油脂中のトコフェルールの変
性なも強力に防止する製剤の提供を目的とする。The purpose of the present invention is to provide a formulation that strongly prevents the denaturation of tocopherols in oils and fats that contain a large amount of highly unsaturated fatty acids, as well as tocopherols in general vegetable oils and terrestrial animal oils that contain a large amount of monoenes and dienes. do.
含有する水相を乳化剤により油相に油中水型に乳α、β
１ｒ１δ盟等トフフェロールの同族体お上ヒ、αトコト
リエノール、αトコトリエノール、δ
ｌトコトリエノール、ｌトコトリエノールなど天然に存
在するものや、ｄｔα−トコフェロールとその銹導体の
ように、合成されたものを含む。The aqueous phase contained in the milk is converted into an oil phase using an emulsifier into a water-in-oil type.
Tocopherol homologues such as 1r1δ, α-tocotrienol, α-tocotrienol, δ1-tocotrienol, and 1-tocotrienol include naturally occurring ones, and synthetic ones such as dtα-tocopherol and its salt conductor.
本発明で用いるフィチン酸とは天然及び合成のフィチン
酸（１、２、３、４、５、６−ｃｙｃｌ。The phytic acid used in the present invention is natural and synthetic phytic acid (1, 2, 3, 4, 5, 6-cycl).
ｈｅｘａｎｅ ｈｅｘｏｌ ｐｈｏｓｐｈｅｒｉｅ ａ
ｃｉｄ）である。また。hexane hexol phosphorye a
cid). Also.
水相としては水を用いるが、エタノール、グリセリン、
液境なとフィチン酸を溶かす物質を適宜用いることがで
とる。Water is used as the aqueous phase, but ethanol, glycerin,
The liquid boundary can be removed by appropriately using a substance that dissolves phytic acid.
乳化剤としては、一般市販の乳化剤の中で油中水型の乳
化に適する乳化剤、例えばグリセリン脂肪酸モノエステ
ル、ソルビタン脂肪酸モノエステル、ポリグリセリン縮
合リシルレート等な単独又は適宜組合わせて用いること
ができる。As the emulsifier, among commercially available emulsifiers, emulsifiers suitable for water-in-oil emulsification, such as glycerin fatty acid monoester, sorbitan fatty acid monoester, polyglycerin condensed lysyllate, etc., can be used alone or in appropriate combinations.
本発明では水相にフィチン酸を０．１〜７０重量％含有
するが、０．１チ未満ではトコフェロールの変性防止効
果が不充分であり、７０％を越えるとフィチン酸の溶解
が困唯となる。In the present invention, the aqueous phase contains 0.1 to 70% by weight of phytic acid, but if it is less than 0.1%, the effect of preventing the denaturation of tocopherol is insufficient, and if it exceeds 70%, it will be difficult to dissolve phytic acid. Become.
本発明の油相とは、一般の液体疎水性物質な意味するが
、特にナタネ油、大豆油、サフラワー油、コーン油、綿
実油などの植物油が好ましい。The oil phase of the present invention refers to a general liquid hydrophobic substance, and vegetable oils such as rapeseed oil, soybean oil, safflower oil, corn oil, and cottonseed oil are particularly preferred.
本発明のトコフェロールの変性防止剤を？Ａ製するにあ
たっては、水相にフィチン酸を所定量溶解し、乳化剤を
あらかじめ所定量混合した油相に乳化すれば良い。また
、乳化するＫは、高速攪拌機、ホモジナイザーなどを用
いて混合乳化すれば良い。What about the tocopherol denaturation inhibitor of the present invention? To produce A, a predetermined amount of phytic acid may be dissolved in an aqueous phase and emulsified in an oil phase in which a predetermined amount of an emulsifier is mixed in advance. Further, K to be emulsified may be mixed and emulsified using a high-speed stirrer, a homogenizer, or the like.
なお、本発明においてはフィチン酸と併せて没食子酸を
少量配合して用いることができる。In addition, in the present invention, a small amount of gallic acid can be used in combination with phytic acid.
トコフェルールの経時的な減少を著しく抑制することが
できる。The decrease in tocopherules over time can be significantly suppressed.
つぎに実施例、比較例および、試噴例により本発明を説
明する。Next, the present invention will be explained with reference to Examples, Comparative Examples, and Test Spraying Examples.
実施例１゜
油相部 重′Ｍｋチナタネ
脱臭油 ４５．０ポリグリセリン縮
合リシル−ト ５．０水相部
グリセリン ４＆０水
１、Ｏフィチ
ン酸 １．０上記に示す配合成
分な混合溶解して、それぞれ油相部と水相部を調製し、
ついで両者を混合してホモジナイザーで乳化分散させ、
油中水型のトコフェロールの変性防止剤を得た。なお以
下の実施例および比較例についても同様に行なった。Example 1゜Oil phase: Heavy Mk Chinese rape deodorized oil 45.0 Polyglycerin condensed lysate 5.0 Water phase: Glycerin 4 & 0 water
1. O-phytic acid 1.0 Mix and dissolve the ingredients shown above to prepare an oil phase and an aqueous phase, respectively.
Then, mix the two and emulsify and disperse with a homogenizer.
A water-in-oil type tocopherol denaturation inhibitor was obtained. Note that the following Examples and Comparative Examples were also conducted in the same manner.
実施例２
油相部 重量％大豆脱臭油
３０．０ソルビタンモノオレー
ト１．０
実施例３゜
油相部 重ｆチ中鎖脂肪酸ト
リグリセリド ４５．０グリセリンモノリル−ト
５．０水相部
フィチン酸 １０、Ｏ没食子酸
０． ｉ液糖（がん元麦芽糖
：水を２５チ
含む） ３９．９比較例
油相部 重看チナタネ脱臭
油 ４５．０ポリグリセリン脂肪酸
エステル ５．０水相部
水 ４
９．０Ｌ−７スコビン酸 １．０試験
例
精製魚油（α−トフフェーールを約１６０ ｐｐｍ含む
）Ｋ実ｍ列１〜３、比較例の４種の乳剤す０゜ＩＪＩ量
チの濃度で添加し、ＡＯＭ条件（９７，８Ｃ’中で空気
をｌ ３ ｄ／ｓｅｅ吹ぎ込む）Ｋ晒し、αトコフェロ
ールの残存量の経時変化を高速液体りｐマドグラフィー
により測定した。その結果は表ＩＫ示した。Example 2 Oil phase weight % Soybean deodorized oil 30.0 Sorbitan monooleate 1.0 Example 3 Oil phase Heavy chain fatty acid triglyceride 45.0 Glycerin monolyte 5.0 Water phase phytic acid 10, O gallic acid
0. I liquid sugar (gangen maltose: Contains 25 parts of water) 39.9 Comparative example Oil phase: Deodorized rapeseed oil 45.0 Polyglycerin fatty acid ester 5.0 Aqueous phase: Water 4
9.0L-7 Scobic acid 1.0 Test example Refined fish oil (contains about 160 ppm α-tophfer) K real m rows 1 to 3, Comparative example 4 emulsions Added at a concentration of 0°IJI amount The samples were exposed to AOM conditions (97.8 C' with air blown at l 3 d/see), and changes in the residual amount of α-tocopherol over time were measured by high-performance liquid polymerography. The results are shown in Table IK.
表 １．（単位ｐｐｍ）
表１より本発明のものはトコフェルールに対して優れた
変性防と力を持つことがわかる。Table 1. (Unit: ppm) From Table 1, it can be seen that the composition of the present invention has excellent denaturation resistance and power against tocopherols.
Claims (1)
剤により油相に油中水型に乳化分散してなるトコフェロ
ールの変性防止剤。A tocopherol denaturation inhibitor obtained by emulsifying and dispersing an aqueous phase containing 0.1 to 70% by weight of phytic acid in an oil phase using an emulsifier in a water-in-oil type.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15506986A JPS6312697A (en) | 1986-07-03 | 1986-07-03 | Modification inhibitor of tocoherol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15506986A JPS6312697A (en) | 1986-07-03 | 1986-07-03 | Modification inhibitor of tocoherol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6312697A true JPS6312697A (en) | 1988-01-20 |
Family
ID=15597981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15506986A Pending JPS6312697A (en) | 1986-07-03 | 1986-07-03 | Modification inhibitor of tocoherol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6312697A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5097871A (en) * | 1989-02-10 | 1992-03-24 | Kurimoto, Ltd. | Pipe for pipe jacking |
| US6248428B1 (en) | 1997-04-15 | 2001-06-19 | Ibiden Co., Ltd. | Adhesive for electroless plating, raw material composition for preparing adhesive for electroless plating and printed wiring board |
| WO2017149701A1 (en) * | 2016-03-02 | 2017-09-08 | 不二製油グループ本社株式会社 | Fat or oil composition |
| WO2017150558A1 (en) * | 2016-03-02 | 2017-09-08 | 不二製油グループ本社株式会社 | Fat or oil composition exhibiting anti-oxidation properties |
| US11957135B2 (en) | 2016-03-02 | 2024-04-16 | Fuji Oil Holdings Inc. | Chocolate-like food containing polyunsaturated fatty acid |
-
1986
- 1986-07-03 JP JP15506986A patent/JPS6312697A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5097871A (en) * | 1989-02-10 | 1992-03-24 | Kurimoto, Ltd. | Pipe for pipe jacking |
| US6248428B1 (en) | 1997-04-15 | 2001-06-19 | Ibiden Co., Ltd. | Adhesive for electroless plating, raw material composition for preparing adhesive for electroless plating and printed wiring board |
| WO2017149701A1 (en) * | 2016-03-02 | 2017-09-08 | 不二製油グループ本社株式会社 | Fat or oil composition |
| WO2017150558A1 (en) * | 2016-03-02 | 2017-09-08 | 不二製油グループ本社株式会社 | Fat or oil composition exhibiting anti-oxidation properties |
| CN108713053A (en) * | 2016-03-02 | 2018-10-26 | 不二制油集团控股株式会社 | Inhibited oil oil/fat composition |
| JPWO2017150558A1 (en) * | 2016-03-02 | 2019-01-17 | 不二製油株式会社 | Antioxidant oil composition |
| TWI726057B (en) * | 2016-03-02 | 2021-05-01 | 日商不二製油集團控股股份有限公司 | Antioxidant grease composition |
| JP2022093378A (en) * | 2016-03-02 | 2022-06-23 | 不二製油株式会社 | Fat or oil composition exhibiting anti-oxidation properties |
| US11957135B2 (en) | 2016-03-02 | 2024-04-16 | Fuji Oil Holdings Inc. | Chocolate-like food containing polyunsaturated fatty acid |
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