Method for manufacturing long chain polyunsaturated fatty acid-containing fat

Abstract

Oxidation stability is improved and a long chain polyunsaturated fatty acid-containing fat with a good flavor is obtained with a method for manufacturing a long chain polyunsaturated fatty acid-containing fat with a moisture content of 3 weight % or less, the method comprising a step for treatment by contact with rosemary. Consequently, it is possible to limit the generation of reversion flavor, unpleasant odors, and peroxides that have health-harming effects over long periods and to provide a highly healthy long chain polyunsaturated fatty acid-containing fat at less cost than in the past. By adding a relatively small amount of an antioxidant substance, oxidation stability can be further improved.

Claims

1. A process for producing a long-chain polyunsaturated fatty acid- containing fat, comprising: a step of contacting a fat with a rosemary, a step of subjecting the fat and rosemary to an adsorption treatment with activated carbon, then a step of removing the rosemary by a filtration, and a step of steam deodorization of the fat after the filtration under reducing pressure, wherein the fat comprises 3% by weight or less of water, wherein the rosemary is a rosemary powder obtained by drying a leaf of Lamiaceae, genus Rosmarinus and pulverizing the dried leaf, wherein the activated carbon is treated by chemical activation, and wherein the steam deodorization temperature is 170° C. or more and the deodorization temperature meets the following formula:
(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000=50 or less.

2. The process for producing a long-chain polyunsaturated fatty acid-containing fat according to claim 1, further comprising a step of bleaching before or at the same time as the step of contacting the fat with the rosemary, wherein the step of contacting is with stirring, and wherein the step of filtration is after the step of bleaching, followed by the step of steam deodorization under reducing pressure.

3. The process for producing a long-chain polyunsaturated fatty acid-containing fat according to claim 1, wherein the water content in the fat is maintained at 3% by weight or less from the step of contacting the fat with the rosemary to the step of steam deodorization under reducing pressure.

4. The process for producing a long-chain polyunsaturated fatty acid-containing fat according to claim 2, wherein the step of bleaching is performed by adding 0.5% by weight or more of the rosemary and 1% by weight or more of activated earth.

5. The process for producing a long-chain polyunsaturated fatty acid-containing fat according to claim 1, wherein the fat comprises 20% by weight or more of long-chain polyunsaturated fatty acid having 5 or more double bonds in a constituent fatty acid composition.

6. The process for producing a long-chain polyunsaturated fatty acid-containing fat according to claim 1, wherein the chemical activation is phosphoric acid activation.

7. The process for producing a long-chain polyunsaturated fatty acid- containing fat according to claim 2, wherein peroxide value of the long-chain polyunsaturated fatty acid-containing fat after the step of steam deodorization is 14 meq/kg or less measured by the following storage test for a long-chain polyunsaturated fatty acid-containing fat: (storage test for a long-chain polyunsaturated fatty acid-containing fat) pouring 50 g of uniformly mixed fat into 100 ml glass container and then sealing the container, storing the glass container at 40° C. for 14 days, and measuring peroxide value of the fat after 14 days storage.

8. The process for producing a long-chain polyunsaturated fatty acid-containing fat according to claim 1, further comprising: a step of bleaching before or at the same time as the step of contacting the fat with the rosemary, wherein the step of contacting is with stirring, wherein the step of filtration is after the step of bleaching, followed by the step of steam deodorization under reducing pressure, wherein the water content in the fat is maintained at 3% by weight or less from the step of contacting the fat with the rosemary to the step of steam deodorization, wherein the step of bleaching is performed by adding 0.5% by weight or more and 10% by weight or less of rosemary, 1% by weight or more and 5% by weight or less of activated earth, and 1% by weight or more and 4% by weight or less of activated carbon, wherein the fat comprises 20% by weight or more of long-chain polyunsaturated fatty acid having 5 or more double bonds in a constituent fatty acid composition.

9. The process for producing a long-chain polyunsaturated fatty acid-containing fat according to claim 8, wherein the chemical activation is phosphoric acid activation.

10. The process for producing a long-chain polyunsaturated fatty acid-containing fat according to claim 8, wherein the water content in the fat is maintained at 1% by weight or less from the step of contacting the fat with the rosemary to the step of steam deodorization, and wherein the step of bleaching is performed by adding 0.5% by weight or more and 5% by weight or less of rosemary, 1% by weight or more and 5% by weight or less of activated earth, and 1% by weight or more and 4% by weight or less of activated carbon.

11. The process for producing a long-chain polyunsaturated fatty acid-containing fat according to claim 6, further comprising a step of bleaching before or at the same time of the step of contacting with the rosemary with stirring, and wherein the step of filtration is after the step of bleaching, followed by the step of steam deodorization under reducing pressure.

12. The process for producing a long-chain polyunsaturated fatty acid- containing fat according to claim 8, further comprising a step of adding a tea extract to the long-chain polyunsaturated fatty acid-containing fat, wherein the chemical activation is phosphoric acid activation.

Description

EXAMPLES

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

(2) In the examples, rosemary powder obtained by grinding the dried leaves of an evergreen shrub of the Lamiaceae rosemary (Rosmarinus officinalis Linne) was used as rosemary.

(3) (Sensory Evaluation Method of Long-Chain Polyunsaturated Fatty Acid-Containing Fat)

(4) Long-chain polyunsaturated fatty acid-containing fat immediately after preparation was evaluated with 10-stages sensory evaluation by 10 panelists in the evaluation items for the flavor including oil odor, fish odor and rosemary odor.

(5) A fat showing evaluations as 4 or more in all items was determined as good.

(6) Oil odor: larger number indicates weaker degradation odor of oil, and smaller number indicates stronger degradation odor of oil.

(7) Fish odor: larger number indicates weaker fish odor, and smaller number indicates stronger fish odor.

(8) Rosemary odor: larger number indicates weaker rosemary odor, and smaller number indicates stronger rosemary odor.

(9) (Storage Test for a Long-Chain Polyunsaturated Fatty Acid-Containing Fat)

(10) The test is carried out by: pouring 50 g of uniformly mixed fat into 100 ml glass container and then sealing the container, storing the glass container at 40° C. for 14 days, and measuring peroxide value of the fat after 14 days storage.
(Sensory Evaluation Method of Long-Chain Polyunsaturated Fatty Acid-Containing Fat after Storage)

(11) Long-chain polyunsaturated fatty acid-containing fat degraded by the storage test was evaluated with 10-stages sensory evaluation by 10 panelists in the evaluation items for the flavor including oil odor, fish odor and reversion odor of rosemary (metal flavor).

(12) A fat showing evaluations as 4 or more in all items was determined as good.

(13) Oil odor: larger number indicates weaker degradation odor of oil, and smaller number indicates stronger degradation odor of oil.

(14) Fish odor: larger number indicates weaker fish odor, and smaller number indicates stronger fish odor.

(15) Reversion odor of rosemary: larger number indicates weaker metal flavor, and smaller number indicates stronger metal flavor.

Example 1

(16) To 100 parts of neutralized tuna oil (acid value=0.10, peroxide value=5.5, iodine value=184, EPA+DHA content=28.0%), 1 part of rosemary powder (trade name: Rosemary (powder), manufactured by S & B foods Inc.), and 3.0 parts of activated earth were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper (trade name: qualitative filter paper No. 2, manufactured by Toyo Roshi Kaisha, Ltd.). Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 160° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(17) Substances dissolved into the fat from rosemary powder were 0.2 part. POV of the fat immediately after preparation was 0.2.

(18) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(19) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed. The results are summarized in Table 1.

Example 2

(20) To 100 parts of neutralized tuna oil, 1 part of rosemary powder, and 3.0 parts of activated earth were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 220° C. for 90 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(21) Substances dissolved into the fat from rosemary powder were 0.2 part.

(22) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(23) The thermal history determined by the following formula was 225.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(24) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 1.

Comparative Example 1

(25) To 100 parts of neutralized tuna oil, 3.0 parts of activated earth was added. The mixture was subjected to a bleaching treatment under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(26) During the neutralized tuna oil, the step of bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(27) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(28) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 1.

Comparative Example 2

(29) To 100 parts of neutralized tuna oil, 0.2 part of rosemary extract (trade name: RM-21B base, manufactured by Mitsubishi-Chemical Foods Corporation), and 3.0 parts of activated earth were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(30) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(31) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(32) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 1.

Comparative Example 3

(33) To 100 parts of neutralized tuna oil, 0.6 part of rosemary extract (trade name: RM-21B base, manufactured by Mitsubishi-Chemical Foods Corporation), and 3.0 parts of activated earth were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(34) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(35) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(36) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 1.

Comparative Example 4

(37) To 100 parts of neutralized tuna oil, 0.6 part of rosemary extract (trade name: RM-21B base, manufactured by Mitsubishi-Chemical Foods Corporation), and 3.0 parts of activated earth were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 130° C. for 60 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat. POV of the fat immediately after preparation was 0.7.

(38) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(39) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 1.

Comparative Example 5

(40) To 100 parts of neutralized tuna oil, 3.0 parts of activated earth was added. The mixture was subjected to a bleaching treatment under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a purified fat. To 100 parts of the purified fat, 0.2 part of rosemary extract was added to obtain a long-chain polyunsaturated fatty acid-containing fat.

(41) During the neutralized tuna oil, the step of bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(42) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(43) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 1.

Comparative Example 6

(44) To 100 parts of neutralized tuna oil, 3.0 parts of activated earth was added. The mixture was subjected to a bleaching treatment under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a purified fat. To 100 parts of the purified fat, 0.6 part of rosemary extract was added to obtain a long-chain polyunsaturated fatty acid-containing fat.

(45) During the neutralized tuna oil, the step of bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(46) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(47) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1 The results are summarized in Table 1.

(48) TABLE-US-00001 TABLE 1 Compara- Compara- Compara- Compara- Compara- Compara- Example Example tive Ex- tive Ex- tive Ex- tive Ex- tive Ex- tive Ex- 1 2 ample 1 ample 2 ample 3 ample 4 ample 5 ample 6 Step of rosemary Rosemary powder (%) 1.0 1.0 treatment and Rosemary powder (in 0.2 0.2 bleaching terms of extract) (%) Rosemary extract (%) 0.2 0.6 0.6 Activated earth (%) 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 Step of Temperature (° C.) 160.0 220.0 180.0 180.0 180.0 130.0 180.0 180.0 deodorization Time (min) 180.0 90.0 180.0 180.0 180.0 60.0 180.0 180.0 Thermal history — 225.0 18.0 18.0 18.0 — 18.0 18.0 Step of adding Rosemary extract (%) 0.2 0.6 after blending Quality EPA + DHA content (%) 27.9 24.0 27.5 27.4 27.5 28.0 27.4 27.4 evaluation EPA + DHA residual ratio 99.6 85.7 98.2 97.9 98.2 100.0 97.9 97.9 in neutralized oil (%) Oil odor immediately 6 10 10 9 9 1 9 9 after preparation Fish odor immediately 6 10 10 9 9 1 9 9 after preparation Rosemary odor 6 10 10 9 8 5 3 1 immediately after preparation Degradation odor of oil 5 4 1 2 2 4 4 4 after storage Fish odor after storage 6 4 1 2 2 4 4 4 Reversion odor of 8 10 10 4 3 3 3 1 rosemary after storage POV after storage 13.4 16.6 20.0 18.2 17.6 14.9 15.7 15.0 (meq/kg) Favorable results were obtained in Examples using rosemary powder both immediately after preparation and after storage. Comparative Examples 2 to 4 using rosemary extract showed inferior results of flavor evaluation compared to Examples. Comparative Examples 2 and 3 showed remarkable deteriorated quality after storage. Comparative Example 4 showed remarkable poor flavor immediately after preparation. Comparative Examples 5 and 6 showed remarkable poor flavor due to rosemary odor immediately after preparation.

Example 3

(49) To 100 parts of neutralized tuna oil, 1 part of rosemary powder, and 3 parts of activated earth were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(50) Substances dissolved into the fat from rosemary powder were 0.2 part.

(51) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(52) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(53) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

Example 4

(54) To 100 parts of neutralized tuna oil, 3 parts of rosemary powder, and 3 parts of activated earth were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(55) Substances dissolved into the fat from rosemary powder were 0.6 part.

(56) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(57) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(58) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

Example 5

(59) To 100 parts of neutralized tuna oil, 5 parts of rosemary powder, and 3 parts of activated earth were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(60) Substances dissolved into the fat from rosemary powder were 1.0 part.

(61) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(62) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(63) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

Example 6

(64) To 100 parts of neutralized tuna oil, 1 part of rosemary powder, and 3 parts of activated earth were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 170° C. for 360 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(65) Substances dissolved into the fat from rosemary powder were 0.2 part.

(66) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(67) The thermal history determined by the following formula was 0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(68) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

Example 7

(69) To 100 parts of neutralized tuna oil, 1 part of rosemary powder, 1.5 parts of activated earth, and 1.5 parts of activated carbon (trade name: Ume-Hachi brand activated carbon SKE, manufactured by Taihei Chemical Industrial Co., Ltd.) were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(70) Substances dissolved into the fat from rosemary powder were 0.2 part.

(71) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(72) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(73) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

Example 8

(74) To 100 parts of neutralized tuna oil, 1 part of rosemary powder, 1.5 parts of activated earth, and 1.5 parts of wood activated carbon with zinc chloride activation (trade name: Ume-Hachi brand activated carbon ZM, manufactured by Taihei Chemical Industrial Co., Ltd.) were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(75) Substances dissolved into the fat from rosemary powder were 0.2 part.

(76) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(77) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(78) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

Example 9

(79) To 100 parts of neutralized tuna oil, 1 part of rosemary powder, 1.5 parts of activated earth, and 1.5 parts of wood activated carbon with phosphoric acid activation (trade name: Ume-Hachi brand activated carbon FN, manufactured by Taihei Chemical Industrial Co., Ltd.) were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(80) Substances dissolved into the fat from rosemary powder were 0.2 part.

(81) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(82) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(83) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

Example 10

(84) To 100 parts of neutralized tuna oil, 3 parts of rosemary powder, 1.5 parts of activated earth, and 1.5 parts of wood activated carbon with phosphoric acid activation were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(85) Substances dissolved into the fat from rosemary powder were 0.6 part.

(86) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(87) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(88) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

Example 11

(89) To 100 parts of neutralized tuna oil, 3 parts of rosemary powder, 1.5 parts of activated earth, and 1.5 parts of wood activated carbon with phosphoric acid activation were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 180° C. for 180 minutes with adding 3 parts of steam to obtain a deodorized fat.

(90) Substances dissolved into the fat from rosemary powder were 0.6 part.

(91) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(92) Then, 2.0% tea extract-containing aqueous solution was prepared by adding tea extract (trade name: Sunphenon 90S, manufactured by Taiyo Kagaku Co., Ltd.) to water. To 100 parts of the deodorized fat heated to 70° C., 0.02 part of emulsifier (POEM PR-100, manufactured by RIKEN VITAMIN CO., LTD.) was added and dissolved, and then 1.0 part of 2.0% tea extract-containing aqueous solution was added. The mixture was stirred with a Homomixer (TK ROBO MIX, manufactured by Tokushu Kika Kogyo Co., Ltd.) at 10000 rpm for 10 minutes. Then, the mixture was subjected to a dehydration treatment with stirring under vacuum of 10 torr at 50° C. for 30 minutes to obtain a long-chain polyunsaturated fatty acid-containing fat containing 200 ppm of tea extract.

(93) The thermal history determined by the following formula was 18.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(94) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

Example 12

(95) To 100 parts of neutralized tuna oil, 3 parts of rosemary powder, 1.5 parts of activated earth, and 1.5 parts of wood activated carbon with phosphoric acid activation were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 190° C. for 180 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(96) Substances dissolved into the fat from rosemary powder were 0.6 part.

(97) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(98) The thermal history determined by the following formula was 72.0:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(99) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

Example 13

(100) To 100 parts of neutralized tuna oil, 3 parts of rosemary powder, 1.5 parts of activated earth, and 1.5 parts of wood activated carbon with phosphoric acid activation were added. The mixture was subjected to a stirring contact treatment in a step of bleaching under vacuum of 1.6 kPa (12 torr) at 120° C. for 15 minutes. Then, the mixture was filtered with a filter paper. Then, 100 parts of the bleached fat was subjected to steam deodorization treatment under vacuum of 0.4 kPa (3 torr) or less at 215° C. for 30 minutes with adding 3 parts of steam to obtain a long-chain polyunsaturated fatty acid-containing fat.

(101) Substances dissolved into the fat from rosemary powder were 0.6 part.

(102) During the neutralized tuna oil, the step of rosemary treatment and bleaching, and the step of deodorization, water content in the fat was 0.01 to 0.10%.

(103) The thermal history determined by the following formula was 60.8:
Thermal history=(deodorization temperature−170° C.)×(deodorization temperature−170° C.)×deodorization time (minutes)/1000.
POV of the fat immediately after preparation was 0.

(104) The content of EPA and DHA in the long-chain polyunsaturated fatty acid-containing fat, evaluation of flavor immediately after preparation, and storage test were performed in a similar manner as Example 1. The results are summarized in Table 2.

(105) TABLE-US-00002 TABLE 2 Example 3 4 5 6 7 8 9 10 11 12 13 Step of rosemary Rosemary powder (%) 1.0 3.0 5.0 1.0 1.0 1.0 1.0 3.0 3.0 3.0 3.0 treatment and Rosemary powder (in 0.2 0.6 1.0 0.2 0.2 0.2 0.2 0.6 0.6 0.6 0.6 bleaching terms of extract) (%) Activated earth (%) 3.0 3.0 3.0 3.0 1.5 1.5 1.5 1.5 1.5 1.5 1.5 Activated carbon (%) 1.5 Wood activated carbon 1.5 with zinc chloride activation (%) Wood activated carbon 1.5 1.5 1.5 1.5 1.5 with phosphoric acid activation (%) Step of Temperature (° C.) 180 180 180 170 180 180 180 180 180 190 215 deodorization Time (min) 180 180 180 360 180 180 180 180 180 180 30 Thermal history 18.0 18.0 18.0 0.0 18.0 18.0 18.0 18.0 18.0 72.0 60.8 Tea extract (%) 0.02 Quality EPA + DHA content (%) 27.5 27.4 27.1 27.7 27.2 27.4 27.5 27.5 27.5 26.5 26.8 evaluation EPA + DHA residual ratio 98.2 97.9 96.8 98.9 97.1 97.9 98.2 98.2 98.2 94.6 95.7 in neutralized oil (%) Oil odor immediately 9 9 9 8 10 10 10 10 10 10 10 after preparation Fish odor immediately 9 9 9 8 10 10 10 10 10 10 10 after preparation Rosemary odor 9 9 8 9 9 9 10 10 10 10 10 immediately after preparation Degradation odor of oil 7 7 8 7 7 8 8 9 10 6 6 after storage Fish odor after storage 7 8 9 8 8 8 9 9 10 7 7 Reversion odor of 9 9 9 9 9 10 10 10 10 9 9 rosemary after storage POV after storage 10.5 10.1 9.5 10.1 10.0 9.6 9.3 8.5 4.2 12.2 11.8 (meq/kg) Examples 3 to 13 obtained by appropriately controlling the thermal history in the step of steam deodorization showed improved EPA+DHA residual ratio in bleached oil as 90% or more, and superior quality in both immediately after preparation and after storage than Examples 1 and 2. In Examples 3 to 11, by adjusting 170° C. or more of temperature and 50 or less of thermal history in the step of steam deodorization, EPA+DHA residual ratio in neutralized oil was improved and more favorable values in the flavor evaluation and peroxide value, which is an index of oxidative stability of fat, after storage were obtained. In Examples 7 to 11, by using activated carbon treated by chemical activation, especially activated carbon treated with phosphoric acid, further favorable values in the flavor evaluation and peroxide value, which is an index of oxidative stability of fat, after storage were obtained.

INDUSTRIAL APPLICABILITY

(106) According to the present invention, a long-chain polyunsaturated fatty acid-containing fat having 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.