LONG-CHAIN POLYUNSATURATED FATTY-ACID-CONTAINING FAT AND FOOD CONTAINING SAME

Abstract

The present invention addresses the problem of providing a versatile, flavorful long-chain polyunsaturated fatty-acid-containing fat having exceptional oxidation stability, and a food that utilizes the fat. The problem can be solved by a long-chain polyunsaturated fatty-acid-containing fat having a specific linoleic acid content and a specific tocopherol-tocotrienol content, the fat containing a fatty acid having five or more double bonds.

Claims

1. A long-chain polyunsaturated fatty acid-containing fat comprising 1 to 35 parts by weight of linoleic acid and 0.001 part by weight to 0.05 part by weight of total amount of the following components (A), on the basis of 1 part by weight of the content of a long-chain polyunsaturated fatty acid having 5 or more double bonds in the constituent fatty acid composition, wherein components (A): β-tocopherol, γ-tocopherol, δ-tocopherol, β-tocotrienol, γ-tocotrienol and δ-tocotrienol.

2. The long-chain polyunsaturated fatty acid-containing fat according to claim 1, wherein the long-chain polyunsaturated fatty acid having 5 or more double bonds is DHA and/or EPA.

3. The long-chain polyunsaturated fatty acid-containing fat according to claim 1, wherein the linoleic acid is 1 to 5 parts by weight, on the basis of 1 part by weight of the content of the long-chain polyunsaturated fatty acid having 5 or more double bonds in the constituent fatty acid composition.

4. The long-chain polyunsaturated fatty acid-containing fat according to claim 3, wherein the content of the long-chain polyunsaturated fatty acid having 5 or more double bonds in the constituent fatty acid composition is 7 to 30% by weight.

5. The long-chain polyunsaturated fatty acid-containing fat according to claim 1, further comprising an oxidation inhibitor.

6. The long-chain polyunsaturated fatty acid-containing fat according to claim 5, wherein the oxidation inhibitor is at least one agent selected from the group consisting of ascorbic acid, ascorbic acid derivative, tea extract, gallic acid, gallic acid derivative and lecithin.

7. The long-chain polyunsaturated fatty acid-containing fat according to claim 1, which is in a state of liquid at 20° C.

8. A food comprising the long-chain polyunsaturated fatty acid-containing fat according to claim 1.

9. A long-chain polyunsaturated fatty acid-containing fat comprising 7% by weight or more and 30% by weight or less of a long-chain polyunsaturated fatty acid having 5 or more double bonds in the constituent fatty acid composition, and 1 to 5 parts by weight of linoleic acid and 0.001 part by weight to 0.05 part by weight of total amount of the components (A), on the basis of 1 part by weight of the content of the long-chain polyunsaturated fatty acid having 5 or more double bonds in the constituent fatty acid composition, wherein a peroxide value after three days obtained from a preservation test of the long-chain polyunsaturated fatty acid-containing fat described below is 65 meq/kg or less: (Method of preservation test of long-chain polyunsaturated fatty acid-containing fat) putting 30 g of uniformly mixed fat into a 100-ml Erlenmeyer flask; letting the Erlenmeyer flask opened to contact with air; and stirring the Erlenmeyer flask in a thermostatic shaking incubator (rotation number: 100 rpm, set at 60° C.) with heating.

10. A long-chain polyunsaturated fatty acid-containing fat comprising 1.5% by weight or more and less than 7% by weight of a long-chain polyunsaturated fatty acid having 5 or more double bonds in the constituent fatty acid composition, and 5 to 35 parts by weight of linoleic acid and 0.001 part by weight to 0.05 part by weight of total amount of the components (A), on the basis of 1 part by weight of the content of the long-chain polyunsaturated fatty acid having 5 or more double bonds in the constituent fatty acid composition, wherein a peroxide value after three days obtained from the preservation test of the long-chain polyunsaturated fatty acid-containing fat is 40 meq/kg or less.

11. A method for suppressing increase in peroxide value of a long-chain polyunsaturated fatty acid-containing fat comprising making a content of linoleic acid to 1 to 35 parts by weight and the total amount of the components (A) to 0.001 part by weight to 0.05 part by weight, on the basis of 1 part by weight of the content of the long-chain polyunsaturated fatty acid having 5 or more double bonds in the constituent fatty acid composition.

12. A method for suppressing increase in peroxide value of a long-chain polyunsaturated fatty acid-containing fat comprising making a content of linoleic acid to 1 to 5 parts by weight and the total amount of the components (A) to 0.001 part by weight to 0.05 part by weight, on the basis of 1 part by weight of the content of the long-chain polyunsaturated fatty acid having 5 or more double bonds in the constituent fatty acid composition.

13. A method for suppressing increase in peroxide value of a food comprising using the long-chain polyunsaturated fatty acid-containing fat according to claim 1.

Description

EXAMPLES

[0067] Examples of the present invention will be explained in more detail herein below. In the examples, both of % and part mean weight basis.

[0068] <Method of Flavor Evaluation of Long-Chain Polyunsaturated Fatty Acid-Containing Fat>

[0069] Evaluation was carried out by 8 panelists on a four level scale by the following basis:

[0070] ◯; no sensible odor

[0071] Δ; slightly sensible odor

[0072] x; oxidative rancidity

[0073] xx; irritating odor

Example 1 to Example 5, Comparative Example 1 to Comparative Example 5

[0074] By using purified fish oil and various purified vegetable oils having the fatty acid composition and tocopherol/tocotrienol shown in Table 1, the fat was uniformly mixed at the ratio described in Tables 2, 4 and 5. POV of the mixed fat was 0. Thirty grams of the mixed fat were put into a 100-ml Erlenmeyer flask and stirred in a thermostatic shaking incubator (rotation number: 100 rpm, set at 60° C.) with the flask opened, and sampling was carried out over time, to analyze POV (meq/kg). Flavor evaluation was carried out in terms of Table 2. The results are shown in Table 3. Additionally, in Example 4, tocopherol composition was appropriately adjusted by adding 0.1 part by weight of Mixed Tocopherol (manufactured by RIKEN VITAMIN Co., Ltd.) on the basis of the fat combination of Comparative Example 1.

TABLE-US-00001 TABLE 1 High-oleic Palm superolein Fish oil Soybean oil Corn oil Rapeseed oil Safflower oil sunflower oil oil Fatty acid C16:0 15.3 10.8 11.2 4.2 6.1 3.7 31.9 composition C18:0 2.5 4.2 1.9 1.8 2.5 2.8 2.8 C18:1 7.7 23.7 30.1 63.2 16.6 85.2 50.5 C18:2 1.4 50.5 52.2 19.0 70.6 6.0 12.2 C18:3 0.1 6.1 1.2 8.5 0.0 0.4 0.4 C20:5 9.7 0.0 0.0 0.0 0.0 0.0 0.0 C22:6 7.2 0.0 0.0 0.0 0.0 0.0 0.0 Tocopherol/Tocotrienol αT* 57 72 146 110 283 626 160 composition αT3* 8 0 7 6 5 0 249 (×10.sup.4) βT 0 16 7 1 0 11 0 γT 2 394 283 210 8 4 0 γT3 0 0 33 53 9 0 27 δT 0 76 17 8 0 0 230 δT3 0 0 0 4 0 0 49 *T indicates tocopherol, and T3 indicates tocotrienol.

TABLE-US-00002 TABLE 2 Comparative Example 4 Fish oil/ Comparative Comparative Comparative Example 3 Safflower oil/ Example 1 Example 2 Example 1 Example 2 Example 3 Fish oil/ High-oleic Fish oil/ Fish Fish oil/ Fish oil/ Fish oil/Palm Soybean oil/ sunflower oil/ Soybean oil = oil/Corn oil = Safflower oil = High-oleic sunflower superolein oil = Corn oil = Linseed oil = 50/50 50/50 50/50 oil = 50/50 50/50 30/50/20 30/51/12/6 Added tocopherol — — — — — — — Fatty acid C16:0 — 13.0 13.2 10.7 9.5 23.6 12.2 8.5 composition C18:0 — 3.3 2.2 2.5 2.6 2.6 3.2 2.6 C18:1 — 15.7 18.9 12.1 46.4 29.1 20.2 23.2 C18:2 A 25.9 26.8 36.0 3.7 6.8 36.1 38.2 C18:3 — 3.1 0.7 0.1 0.3 0.3 3.4 3.1 C20:5 B 4.9 4.9 4.9 4.9 4.9 2.9 2.9 C22:6 C 3.6 3.6 3.6 3.6 3.6 2.2 2.2 B + C 8.4 8.4 8.4 8.4 8.4 5.1 5.1 A/(B + C) 3.1 3.2 4.3 0.4 0.8 7.1 7.5 Tocopherol/ αT* — 65 101 170 341 108 83 243 Tocotrienol αT3* 4 7 6 4 128 4 5 composition βT D 8 4 0 6 0 9 1 (×10.sup.4) γT 198 143 5 3 1 254 5 γT3 0 16 5 0 13 7 5 δT 38 8 0 0 115 41 0 δT3 0 0 0 0 25 0 0 D/(B + C) 28.9 20.2 1.1 1 18.2 61.4 2.2 POV Day 2 2 2 257 39 17 <1 25 Day 3 12 15 >300 105 71 2 66 Day 5 189 155 — >300 >300 12 >300 *T indicates tocopherol, and T3 indicates tocotrienol.

TABLE-US-00003 TABLE 3 Comparative Example 4 Fish oil/ Comparative Comparative Example 3 Safflower oil/ Example 1 Comparative Example 2 Example 3 Fish oil/ High-oleic Fish oil/ Example 2 Example 1 Fish oil/ Fish oil/Palm Soybean oil/ sunflower oil/ soybean oil = Fish oil/ Fish oil/ High-oleic sunflower superolein oil = Corn oil = Linseed oil = 50/50 Corn oil = 50/50 Safflower oil = 50/50 oil = 50/50 50/50 30/50/20 30/51/12/6 Flavor Day 2 ◯ ◯ X X ◯ ◯ X Day 3 ◯ ◯ XX X X ◯ X Day 5 X X — XX XX ◯ XX

[0075] Fatty acid composition, tocopherol/tocotrienol and POV values are shown in Table 2. It became clear that increase in POV was remarkably high in a case of where the fatty acid composition ratio (A/(B+C)) and the tocopherol/tocotrienol ratio (D/(B+C)) to the DHA+EPA content (B+C) did not satisfy the conditions of the present invention, in comparison of the DHA/EPA content in Examples 1 to 2 and Comparative Examples 1 to 3. In addition, from the comparison of Comparative Example 1 and Examples 1 and 2, it was shown that not only the fatty acid composition ratio (A/(B+C)) but also the tocopherol/tocotrienol ratio (D/(B+C)) was important for suppression of increase in POV value. Furthermore, it became clear that (Comparative Example 1), which satisfied the claimed scope of Patent Document 26 in which effect of suppressing fish odor was regarded as high, did not suppress increase in POV, and that increase in POV was suppressed by using a fat of which fatty acid composition ratio (A/(B+C)) and tocopherol/tocotrienol ratio (D/(B+C)) to DHA+EPA content (B+C) satisfied the conditions of the present invention.

[0076] Additionally, better flavor evaluation was obtained in Examples as compared with that of Comparative Examples.

TABLE-US-00004 TABLE 4 Comparative Example 4 Example 1 Fish oil/ Fish oil/ Safflower oil = Safflower oil = 50/50 50/50 Added tocopherol 1000 ppm — Fatty acid C16:0 — 10.7 10.7 composition C18:0 — 2.5 2.5 C18:1 — 12.1 12.1 C18:2 A 36.0 36.0 C18:3 — 0.1 0.1 C20:5 B 4.9 4.9 C22:6 C 3.6 3.6 B + C 8.4 8.4 A/(B + C) 4.3 4.3 Tocopherol/ αT*  — 185 170 Tocotrienol αT3* 6 6 composition βT D 14 0 (×10.sup.4) γT  347 5 γT3 5 5 δT  354 0 δT3 0 0 D/(B + C) 85.3 1.1 POV Day 2 23 257 Day 3 50 >300 Day 5 >300 — *T indicates tocopherol, and T3 indicates tocotrienol.

[0077] In Example 4, in which Mixed Tocopherol was additionally added to appropriately adjust the tocopherol/tocotrienol ratio (D/(B+C)) to DHA+EPA content (B+C), increase in POV was suppressed as compared with Comparative Example 1, which had an equivalent fat combination.

TABLE-US-00005 TABLE 5 Comparative Example 5 Example 5 Fish oil/Safflower Fish oil/ oil/High-oleic Soybean oil/ sunflower oil/ Corn oil = Linseed oil = 10/55/35 10/62/20/10 Added tocopherol — — Fatty acid C16:0 — 11.4 6.5 composition C18:0 — 3.2 2.6 C18:1 — 24.3 29.9 C18:2 A 46.2 46.4 C18:3 — 3.8 4.1 C20:5 B 1.0 1.0 C22:6 C 0.7 0.7 B + C 1.7 1.7 A/(B + C) 27.3 27.5 Tocopherol/ αT*  — 97 306 Tocotrienol αT3* 3 4 composition βT D 11 2 (×10.sup.4) γT  316 6 γT3 12 6 δT  47 0 δT3 0 0 D/(B + C) 228.6 8.4 POV Day 2 <1 — Day 3 2 24 Day 5 2 70 *T indicates tocopherol, and T3 indicates tocotrienol.

[0078] It became clear that increase in POV was small and oxidation stability was high in Example 5 in which the fatty acid composition ratio (A/(B+C)) and the tocopherol/tocotrienol ratio (D/(B+C)) to the DHA+EPA content (B+C) were appropriately adjusted, even under conditions of low DHA/EPA content.

Example 6 to Example 13 and Comparative Example 6 to Comparative Example 11

[0079] By using purified tuna oil and various purified vegetable oils having the fatty acid composition and tocopherol/tocotrienol shown in Table 6, the fat was uniformly mixed at the ratio described in Tables 7 and 9. POV of the mixed fat was 0. Thirty grams of the mixed fat were put into a 100-ml Erlenmeyer flask and stirred in a thermostatic shaking incubator (rotation number: 100 rpm, set at 60° C.) with the flask opened, and sampling was carried out over time, to analyze POV (meq/kg). Flavor evaluation was carried out in terms of Table 7. The results are shown in Table 8. Additionally, in Example 13, 0.05 part by weight of tea polyphenol-containing composition (manufactured by Taiyo Kagaku Co., Ltd., product name: Sunphenon 90S) was added to the combination described in Example 12. Additionally, the long-chain polyunsaturated fatty acid-containing fat of Example 13 was prepared by preparing an aqueous solution to which 50% by weight tea polyphenol-containing composition was dissolved, adding 0.1 part by weight of the 50% by weight aqueous tea polyphenol solution and 0.1 part by weight of emulsifier (manufactured by RIKEN VITAMIN Co., Ltd., POEM PR-100) to 99.8 parts by weight of oil, and stirring the mixture by a homomixer (TK ROBO MIX, manufactured by Tokusyu Kika Kogyo Co., Ltd.) at 10000 rpm×5 minutes.

TABLE-US-00006 TABLE 6 High-oleic Palm auperolein Tuna oil Soybean oil Rapeseed oil Safflower oil sunflower oil oil Fatty acid C16:0 19.4 10.8 4.2 6.1 3.7 31.9 composition C18:0 5.1 4.2 1.8 2.5 2.8 2.8 C18:1 19.4 23.7 63.2 16.6 85.2 50.5 C18:2 1.1 50.5 19.0 70.6 6.0 12.2 C18:3 0.6 6.1 8.5 0.0 0.4 0.4 C20:5 6.3 0.0 0.0 0.0 0.0 0.0 C22:6 21.7 0.0 0.0 0.0 0.0 0.0 Tocopherol/ αT* 162 73 110 283 626 160 Tocotrienol αT3* 9 0 6 5 0 249 composition βT 0 16 1 0 11 0 (×10.sup.4) γT 7 394 210 8 4 0 γT3 0 0 53 9 0 27 δT 0 76 8 0 0 230 δT3 0 0 4 0 0 49 *T indicates tocopherol, and T3 indicates tocotrienol.

TABLE-US-00007 TABLE 7 Comparative Example 9 Example 6 Example 7 Example 8 Example 6 Tuna oil/ Example 10 Tuna oil/ Tuna oil/ Tuna oil/ Tuna oil/ Soybean Tuna Soybean Soybean Soybean Soybean oil/Rapeseed oil = oil/Rapeseed oil = oil = 18/82 oil = 25/75 oil = 50/50 oil = 75/25 18/41/41 18/82 Fatty acid C16:0 — 12.3 13.0 15.1 17.3 9.6 6.9 composition C18:0 — 4.4 4.4 4.7 4.9 3.4 2.4 C18:1 — 22.9 22.6 21.6 20.5 39.1 55.3 C18:2 A 41.6 38.2 25.8 13.5 28.7 15.8 C18:3 — 5.1 4.7 3.4 2.0 6.1 7.1 C20:5 B 1.1 1.6 3.2 4.7 1.1 1.1 C22:6 C 3.9 5.4 10.9 16.3 3.9 3.9 B + C 5.0 7.0 14.0 21.0 5.0 5.0 A/(B + C) 8.3 5.5 1.8 0.6 5.7 3.1 Tocopherol/ αT* — 89 95 118 140 104 119 Tocotrienol αT3* 2 2 5 7 4 7 composition βT D 13 12 8 4 7 1 (×10.sup.4) γT 324 297 201 104 249 174 γT3 0 0 0 0 22 43 δT 62 57 38 19 34 7 δT3 0 0 0 0 1 3 D/(B + C) 79.2 52.3 17.6 6 62.1 45 POV Day 2 <1 2 3 109 <1 1 Day 3 <1 2 50 >300 <1 7 Day 5 11 109 >300 — 17 51 Comparative Comparative Comparative Example 7 Example 8 Example 11 Example 9 Tuna Tuna oil/High- Tuna oil/Palm Tuna oil/Palm Comparative Example 10 oil/Saffolwer oleic sunflower superolein oil = superolein oil = Tuna oil/Palm superolein oil = oil = 50/50 oil = 50/50 25/75 50/50 75/25 Fatty acid C16:0 — 12.8 11.6 28.8 25.7 22.5 composition C18:0 — 3.8 4.0 3.4 4.0 4.5 C18:1 — 18.0 52.3 42.7 35.0 27.2 C18:2 A 35.9 3.6 9.4 6.7 3.9 C18:3 — 0.3 0.5 0.5 0.5 0.6 C20:5 B 3.2 3.2 1.6 3.2 4.7 C22:6 C 10.9 10.9 5.4 10.9 16.3 B + C 14.0 14.0 7.0 14.0 21.0 A/(B + C) 2.6 0.3 1.3 0.5 0.2 Tocopherol/ αT* — 222 394 160 161 161 Tocotrienol αT3* 7 5 189 129 69 composition βT D 0 6 0 0 0 (×10.sup.4) γT 8 6 2 4 6 γT3 5 0 20 13 7 δT 0 0 173 115 58 δT3 0 0 37 25 12 D/(B + C) 0.9 0.8 33 11.2 3.9 POV Day 2 >300 101 17 92 236 Day 3 — 272 54 217 >300 Day 5 — >300 230 >300 — *T indicates tocopherol, and T3 indicates tocotrienol.

TABLE-US-00008 TABLE 8 Compar- Compar- Compar- Compar- Example Compar- ative ative ative ative 9 ative Example Example Example Example Example Example Example Example Tuna oil/ Example Example 8 11 9 10 6 7 8 6 Soybean 10 7 Tuna oil/ Tuna oil/ Tuna oil/ Tuna oil/ Tuna oil/ Tuna oil/ Tuna oil/ Tuna oil/ oil/ Tuna oil/ Tuna oil/ High-oleic Palm Palm Palm Soybean Soybean Soybean Soybean Rapeseed Rapeseed Safflower sunflower superolein superolein superolein oil = oil = oil = oil = oil = oil = oil = oil = oil = oil = oil = 18/82 25/75 50/50 75/25 18/41/41 18/82 50/50 50/50 25/75 50/50 75/25 Flavor Day 2 ◯ ◯ ◯ X ◯ ◯ XX X ◯ X XX Day 3 ◯ ◯ Δ XX ◯ ◯ — XX Δ XX — Day 5 ◯ X XX — Δ Δ — — XX — —

[0080] In tuna oil, there was also a tendency that increase in POV was suppressed and that oxidation stability of the fat was high in Examples in which the fatty acid composition ratio (A/(B+C)) and the tocopherol/tocotrienol ratio (D/(B+C)) to the DHA+EPA content (B+C) were appropriately adjusted, as is the case with the test on fish oil. For example, while DHA/EPA content was same in Example 8 and Comparative Examples 7 and 9, increase in POV over time was small and oxidation stability was remarkably high in Example 8, which corresponds to the conditions of the present invention.

[0081] Additionally, good flavor evaluation was obtained in Examples as compared with that in Comparative Examples.

TABLE-US-00009 TABLE 9 Comparative Example 11 Example 12 Example 13 Tuna oil/High- Tuna oil/Soybean Tuna oil/Soybean oleic sunflower oil = 6/94 oil = 6/94 oil = 6/94 Added — Tea — antioxidative polyphenol substance 0.05% Fatty acid composition C16:0 — 11.3 11.3 4.6 C18:0 — 4.3 4.3 2.9 C18:1 — 23.4 23.4 81.3 C18:2 A 47.5 47.5 5.7 C18:3 — 5.8 5.8 0.4 C20:5 B 0.4 0.4 0.4 C22:6 C 1.3 1.3 1.3 B + C 1.7 1.7 1.7 A/(B + C) 28.3 28.3 3.4 Tocopherol/Tocotrienol αT* — 79 79 598 composition (×10.sup.4) αT3* 1 1 1 βT D 15 15 10 γT 371 371 4 γT3 0 0 0 δT 71 71 0 δT3 0 0 0 D/(B + C) 271.8 271.8 8.8 POV Day 2 <1 <1 <1 Day 3 <1 <1 <1 Day 5 8 <1 49 *T indicates tocopherol, and T3 indicates tocotrienol.

[0082] It became clear that increase in POV was small and that oxidation stability was high in Examples in which the fatty acid composition ratio (A/(B+C)) and the tocopherol/tocotrienol ratio (D/(B+C)) to the DHA+EPA content (B+C) were appropriately adjusted, even in Examples 12 and 13 in which tocopherol+tocotrienol total content was smaller than that of Comparative Example 11, under the conditions of low DHA/EPA content. In addition, from Examples 12 and 13, it also became clear that oxidation stability was further increased by adding an oxidation inhibitor.

Example 14, Example 15, Comparative Example 12 and Comparative Example 13

[0083] By using purified algae oil and various purified vegetable oils having the fatty acid composition and tocopherol/tocotrienol shown in Table 10, the fat was uniformly mixed at the ratio described in Tables 11 and 12. POV of the mixed fat was 0. Thirty grams of the mixed fat were put into a 100-ml Erlenmeyer flask and stirred in a thermostatic shaking incubator (rotation number: 100 rpm, set at 60° C.) with the flask opened, and sampling was carried out over time, to analyze POV (meq/kg).

TABLE-US-00010 TABLE 10 High-oleic Palm Algae Soybean sunflower superolein oil oil oil oil Fatty acid C16:0 20.7 10.8 3.7 31.9 composition C18:0 1.5 4.2 2.8 2.8 C18:1 4.7 23.7 85.2 50.5 C18:2 0.0 50.5 6.0 12.2 C18:3 0.0 6.1 0.4 0.4 C20:5 0.3 0.0 0.0 0.0 C22:6 50.7 0.0 0.0 0.0 Tocopherol/ αT*  412 73 626 160 Tocotrienol αT3* 5 0 0 249 composition βT 0 16 11 0 (×10.sup.4) γT  0 394 4 0 γT3 0 0 0 27 δT  0 76 0 230 δT3 0 0 0 49 *T indicates tocopherol, and T3 indicates tocotrienol.

TABLE-US-00011 TABLE 21 Comparative Example 14 Example 12 Algae oil/ Algae oil/Palm Soybean superolein oil = oil = 30/70 30/70 Fatty acid C16:0 — 13.8 28.5 composition C18:0 — 3.4 2.4 C18:1 — 18.0 36.8 C18:2 A 35.4 8.5 C18:3 — 4.3 0.3 C20:5 B 0.1 0.1 C22:6 C 15.2 15.2 B + C 15.3 15.3 A/(B + C) 2.3 0.6 Tocopherol/ αT*  — 175 236 Tocotrienol αT3* 2 176 composition βT D 11 0 (×10.sup.4) γT  276 0 γT3 0 19 δT  53 161 δT3 0 34 D/(B + C) 22.2 14 POV Day 2 5 73 Day 3 20 >300 *T indicates tocopherol, and T3 indicates tocotrienol.

[0084] While the contents of DHA and EPA were same in Example 14 and Comparative Example 12, increase in POV was small and oxidation stability was high in Example 14 in which the fatty acid composition ratio (A/(B+C)) and the tocopherol/tocotrienol ratio (D/(B+C)) to the DHA+EPA content (B+C) were appropriately adjusted.

TABLE-US-00012 TABLE 12 Comparative Example 13 Example 15 Algae oil/ Algae oil/ High-oleic Soybean sunflower oil = 48/52 oil = 48/52 Fatty acid C16:0 — 15.6 12.1 composition C18:0 — 2.9 1.7 C18:1 — 14.6 35.1 C18:2 A 26.3 9.9 C18:3 — 3.2 4.4 C20:5 B 0.1 0.1 C22:6 C 24.3 24.3 B + C 24.5 24.5 A/(B + C) 1.1 0.4 Tocopherol/ αT*  — 236 255 Tocotrienol αT3* 2 6 composition βT D 8 0 (×10.sup.4) γT  205 109 γT3 0 27 δT  39 4 δT3 0 2 D/(B + C) 10.3 5.8 POV Day 2 147 >300 Day 3 >300 — *T indicates tocopherol, and T3 indicates tocotrienol.

[0085] While the contents of DHA and EPA were same in Example 15 and Comparative Example 13, increase in POV was small and oxidation stability was high in Example 15 in which the fatty acid composition ratio (A/(B+C)) and the tocopherol/tocotrienol ratio (D/(B+C)) to the DHA+EPA content (B+C) were appropriately adjusted.

Example 16 and Example 17

[0086] By using purified tuna oil and various purified vegetable oils having the fatty acid composition and tocopherol/tocotrienol shown in Tables 1 and 6, the fat was uniformly mixed at the ratio described in Table 13. POV of the mixed fat was 0. Thirty grams of the mixed fat were put into a 100-ml Erlenmeyer flask and stirred in a thermostatic shaking incubator (rotation number: 100 rpm, set at 60° C.) with the flask opened, and sampling was carried out over time, to analyze POV (meq/kg). Additionally, as a method of adding ascorbic acid, an aqueous solution to which 16.7% by weight ascorbic acid-containing composition was dissolved was prepared, and 0.3 part by weight of the 16.7% by weight aqueous ascorbic acid solution, 0.1 part by weight of emulsifier (manufactured by RIKEN VITAMIN Co., Ltd., POEM PR-100) were added to 99.6 parts by weight of oil, and then stirred with a homomixer (TK ROBO MIX, manufactured by Tokusyu Kika Kogyo Co., Ltd.) at 10000 rpm×5 minutes.

TABLE-US-00013 TABLE 13 Example 16 Example17 Tuna oil/ Tuna oil/ Soybean Corn oil = oil = 40/60 40/60 Added antioxidative Ascorbic acid Ascorbic acid substance 0.05% 0.05% Fatty acid C16:0 — 16.0 16.1 composition C18:0 — 4.7 3.8 C18:1 — 21.1 23.7 C18:2 A 20.9 21.7 C18:3 — 2.8 0.8 C20:5 B 3.8 3.8 C22:6 C 13.0 13.0 B + C 16.8 16.8 A/(B + C) 1.2 1.3 Tocopherol/ αT*  — 126.3 155.4 Tocotrienol αT3* 5.6 8.3 composition βT D 6.3 2.9 (×10.sup.4) γT  162.0 117.6 γT3 0.0 13.2 δT  30.2 6.6 δT3 0.0 0.0 D/(B + C) 11.8 8.4 POV Day 8  <0.5 <0.5 Day 21 18.8 13.0 *T indicates tocopherol, and T3 indicates tocotrienol.

[0087] Oxidation stability was improved by adding ascorbic acid as is the case with addition of tea polyphenol, and a long-chain polyunsaturated fatty acid-containing fat having good oxidation stability of which POV value on day 8 is 0.5 and the POV on day 21 was less than 20 was obtained.

INDUSTRIAL APPLICABILITY

[0088] According to the present invention, a long-chain polyunsaturated fatty acid-containing fat having improved oxidation stability and good flavor is obtained by a simple method, and a long-chain polyunsaturated fatty acid-containing fat wherein generation of reversion odor and unpleasant odor, and peroxide substance which adversely acts on health is suppressed for a long period of time, and having high health advantage is utilized for food, pharmaceutical composition, cosmetic, pet food, quasi drug and the like, by using the long-chain polyunsaturated fatty acid-containing fat of the present invention.