JP6301080B2 - Partially hydrogenated oil and fat, oil and fat composition containing the same, and method for producing the same - Google Patents
Partially hydrogenated oil and fat, oil and fat composition containing the same, and method for producing the same Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 239000003921 oil Substances 0.000 claims description 209
- 239000003925 fat Substances 0.000 claims description 118
- 239000000796 flavoring agent Substances 0.000 claims description 82
- 235000019634 flavors Nutrition 0.000 claims description 82
- 239000000194 fatty acid Substances 0.000 claims description 34
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 33
- 229930195729 fatty acid Natural products 0.000 claims description 33
- 150000004665 fatty acids Chemical class 0.000 claims description 33
- 150000002978 peroxides Chemical class 0.000 claims description 21
- 238000001256 steam distillation Methods 0.000 claims description 18
- 230000002708 enhancing effect Effects 0.000 claims description 14
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 238000007664 blowing Methods 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 239000008157 edible vegetable oil Substances 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 4
- 230000002787 reinforcement Effects 0.000 claims description 4
- 238000005728 strengthening Methods 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 3
- 235000019198 oils Nutrition 0.000 description 191
- 235000019197 fats Nutrition 0.000 description 105
- 238000000034 method Methods 0.000 description 27
- 235000019482 Palm oil Nutrition 0.000 description 15
- 239000002540 palm oil Substances 0.000 description 15
- 238000007254 oxidation reaction Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 13
- 230000003647 oxidation Effects 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 238000005984 hydrogenation reaction Methods 0.000 description 12
- 239000000523 sample Substances 0.000 description 12
- 235000013305 food Nutrition 0.000 description 11
- 238000012360 testing method Methods 0.000 description 9
- 238000002835 absorbance Methods 0.000 description 7
- 235000014593 oils and fats Nutrition 0.000 description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 7
- 239000012488 sample solution Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003549 soybean oil Substances 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- 239000012086 standard solution Substances 0.000 description 6
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 5
- 235000019860 lauric fat Nutrition 0.000 description 5
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002285 corn oil Substances 0.000 description 4
- 235000005687 corn oil Nutrition 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 235000010692 trans-unsaturated fatty acids Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- -1 aldehyde compound Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000015228 chicken nuggets Nutrition 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 239000008162 cooking oil Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical group CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- 235000019635 fat flavor Nutrition 0.000 description 2
- 235000019869 fractionated palm oil Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BXZFRAKKWTXCSD-UHFFFAOYSA-N 3-(4-aminophenoxy)propanoic acid Chemical compound NC1=CC=C(OCCC(O)=O)C=C1 BXZFRAKKWTXCSD-UHFFFAOYSA-N 0.000 description 1
- BNIDBPBBKOFHJO-UHFFFAOYSA-N 4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1.COC1=CC=C(N)C=C1 BNIDBPBBKOFHJO-UHFFFAOYSA-N 0.000 description 1
- 241001137251 Corvidae Species 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 235000014510 cooky Nutrition 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 235000012489 doughnuts Nutrition 0.000 description 1
- 229940073505 ethyl vanillin Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 235000012020 french fries Nutrition 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- JBXYCUKPDAAYAS-UHFFFAOYSA-N methanol;trifluoroborane Chemical compound OC.FB(F)F JBXYCUKPDAAYAS-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 235000015108 pies Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008256 whipped cream Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Landscapes
- Edible Oils And Fats (AREA)
- Meat, Egg Or Seafood Products (AREA)
Description
本発明は、食品に用いられる油脂組成物及びその製造方法に関する。より詳細には、水素添加油脂由来の好ましい風味を持つ食品を製造することができる油脂組成物に用いられる部分水素添加油脂及びその製造方法、並びに前記部分水素添加油脂を含む油脂組成物に関する。 The present invention relates to an oil and fat composition used for foods and a method for producing the same. More specifically, the present invention relates to a partially hydrogenated fat and oil used in an oil and fat composition capable of producing a food having a preferred flavor derived from hydrogenated fat and oil, a method for producing the same, and an oil and fat composition containing the partially hydrogenated fat and oil.
従来、油脂の可塑性や融点の調整、酸化安定性の向上などの目的で、油脂を水素添加(硬化)することにより、不飽和脂肪酸を減じた硬化油が使用されてきた。近年、水素添加によって副次的に生成されるトランス脂肪酸の摂取と心疾患のリスクとの関連が明らかとなり、トランス脂肪酸含量を出来るだけ低減した油脂が求められている。
しかしながら、硬化油には硬化油風味と呼ばれる独特の甘さ、コク味といった風味があり、その食品の味の一部となっている。トランス脂肪酸低減のために硬化油の使用量を減らすと、甘さ、コク味と言った硬化油風味が減り、その食品のおいしさも落ちるという問題がある。
一方、水素添加油脂由来の風味(あるいは硬化油風味)を添加する方法は様々な方法が試みられている。例えば、バニリン、エチルバニリン等の添加による硬化油風味付与が報告されている(特許文献1参照)。しかしながら、風味の質が本来の硬化油風味とは異なる。また、パーム油の分別硬質油を50質量%以上用いることにより、トランス脂肪酸含有量を低減しながら水素添加油脂由来の風味を出す方法が報告されている(特許文献2参照)が、トランス脂肪酸の低減量が不十分である。
パーム油にラードあるいは硬化油を添加して用いることにより、トランス脂肪酸含有量を低減しながら水素添加油脂風味を出す方法も報告されている(特許文献3参照)が、風味の質が本来の硬化油風味とは異なる。
過酸化物価0.4〜7の部分水素添加油脂を用いることにより、低トランス脂肪酸油脂の水素添加油脂風味を強くする方法(特許文献4参照)があるが、酸化劣化した風味が問題となる。
蒸留精製したパーム油を用いることにより、トランス脂肪酸含有量を低減しながら水素添加油脂風味を出す方法(特許文献5参照)があるが硬化油風味の強度が不十分である。
ヨウ素価54〜70のパーム分別軟質油を25〜65質量%、及びヨウ素価10〜55のパーム分別硬質油を17質量%以上50質量%未満含有する油脂組成物を加熱調理用の油脂に用いることにより、トランス脂肪酸含量を低減した場合でも、水素添加臭の風味を有する加熱調理用油脂組成物も報告されているが(特許文献6参照)、硬化油風味の強度が依然として不十分である。
動植物油脂と水との混合物を、酸素の存在下、100〜130℃の加熱条件化に還流しながらフレーバーを生成させ、排気される酸素に伝播されて揮散するフレーバー混合物を脂肪酸トリグリセリド溶液中に収集することを特徴とするフレーバー付与剤の製造法(特許文献7参照)が報告されているが、酸化劣化した風味が問題である。また、加熱使用時の風味の持続性がないという問題もある。
Conventionally, hardened oils in which unsaturated fatty acids are reduced by hydrogenating (hardening) fats and oils have been used for the purpose of adjusting the plasticity and melting point of the fats and oils and improving the oxidation stability. In recent years, the relationship between the intake of trans-fatty acids produced by hydrogenation and the risk of heart disease has been clarified, and there has been a demand for fats and oils with the trans-fatty acid content reduced as much as possible.
However, the hardened oil has a unique sweetness and a rich taste called hardened oil flavor, and is a part of the taste of the food. If the amount of hardened oil used is reduced to reduce trans fatty acids, there is a problem that the hardened oil flavor such as sweetness and richness is reduced and the taste of the food is also reduced.
On the other hand, various methods have been tried to add a flavor derived from hydrogenated fats (or hardened oil flavor). For example, imparting a hardened oil flavor by adding vanillin, ethyl vanillin or the like has been reported (see Patent Document 1). However, the flavor quality is different from the original hardened oil flavor. In addition, a method for producing a flavor derived from hydrogenated fat while reducing the content of trans fatty acid by using 50% by mass or more of the fractionated hard oil of palm oil has been reported (see Patent Document 2). The amount of reduction is insufficient.
A method of producing a hydrogenated fat flavor while reducing the trans fatty acid content by adding lard or hardened oil to palm oil has been reported (see Patent Document 3), but the quality of the flavor is inherently hardened. It is different from oil flavor.
There is a method for enhancing the hydrogenated fat and oil flavor of low trans fatty acid fats and oils by using partially hydrogenated fats and oils having a peroxide value of 0.4 to 7 (see Patent Document 4), but the oxidatively deteriorated flavor becomes a problem.
There is a method (see Patent Document 5) for producing a hydrogenated fat flavor while reducing the trans fatty acid content by using distilled and refined palm oil, but the strength of the hardened oil flavor is insufficient.
An oil / fat composition containing 25 to 65% by mass of a palm fractionated soft oil having an iodine value of 54 to 70 and 17% by mass or more and less than 50% by mass of a palm fractionated hard oil having an iodine value of 10 to 55 is used as an oil for cooking. Thus, even when the trans fatty acid content is reduced, a cooking oil / fat composition having a flavor of hydrogenation odor has also been reported (see Patent Document 6), but the strength of the cured oil flavor is still insufficient.
Flavor is produced by refluxing a mixture of animal and vegetable oils and water under heating conditions of 100 to 130 ° C. in the presence of oxygen, and the flavor mixture propagating to the exhausted oxygen and volatilizing is collected in a fatty acid triglyceride solution. Although a method for producing a flavor imparting agent characterized by the above has been reported (see Patent Document 7), the flavor deteriorated by oxidation is a problem. There is also a problem that there is no sustainability of flavor during heating.
本発明の課題は、食品において硬化油(水素添加油脂)由来の好ましい風味(硬化油風味ともいう)を強く生じさせる、トランス脂肪酸含有量が低下した油脂組成物に用いる硬化油風味強化用油脂及びその製造方法を提供することである。 An object of the present invention is to provide a hardened oil flavor-enhancing oil and fat used in an oil and fat composition having a reduced trans fatty acid content, which strongly causes a preferred flavor (also referred to as a hardened oil flavor) derived from hardened oil (hydrogenated fat and oil) in food The manufacturing method is provided.
本発明者らは、上記目的を達成するため、鋭意検討を行った結果、部分水素添加油脂を、100℃〜240℃の温度で空気を吹き込みながら加熱酸化した後、220℃以下で真空水蒸気蒸留して得られる油脂の硬化油風味が特に強化されていることを見いだし、本発明を完成した。
また、本発明者らは、上記製造方法により得られる硬化油風味が特に強化されている部分水素添加油脂が、いわゆるTotox値が所定の値より高く、過酸化物価が所定の値よりも低いことを見いだし、本発明を完成した。
As a result of intensive studies to achieve the above object, the present inventors have conducted heat oxidation of partially hydrogenated oil and fat while blowing air at a temperature of 100 ° C. to 240 ° C., and then vacuum steam distillation at 220 ° C. or lower. The hardened oil flavor of the fats and oils obtained in this way was found to be particularly enhanced, and the present invention was completed.
In addition, the inventors of the present invention have a partially hydrogenated oil and fat with a particularly enhanced hardened oil flavor obtained by the above-described production method, having a so-called Totox value higher than a predetermined value and a peroxide value lower than a predetermined value. And the present invention was completed.
すなわち、部分水素添加油脂を100℃〜240℃の温度で空気を吹き込みながら加熱酸化した後、220℃以下で真空水蒸気蒸留して残った油脂は硬化油風味が特に増強されていることが見いだされた。
また、以下の式(1)で表されるTotox値が24.5以上であり、かつ過酸化物価が8以下の部分水素添加油脂である、硬化油風味強化用油脂:(POV×2+AnV)(1)(式中、POVは過酸化物価を表し、AnVはアニシジン価を表す。)の硬化油風味が特に増強されていることが見いだされた。
この強化された硬化油風味は、本来の硬化油風味を全般的に強化するものであるが、特に硬化油特有の甘さ、コクを付与する効果がある。加えて、前記油脂をフライなどの加熱用途に用いた場合には、硬化油風味の強さが経時的に変化しにくく、持続性があり優れた効果を奏する。
That is, it has been found that the hydrogenated fats and oils are heated and oxidized while blowing air at a temperature of 100 ° C. to 240 ° C., and then the oils and fats left by vacuum steam distillation at 220 ° C. or less have a particularly enhanced hardened oil flavor. It was.
Moreover, the oil for fat-hardened oil flavor enhancement oil which is Tox value represented by the following formula | equation (1) is 24.5 or more, and a peroxide value is 8 or less: (POV * 2 + AnV) ( 1) It was found that the hydrogenated oil flavor of POV (wherein POV represents the peroxide value and AnV represents the anisidine value) was particularly enhanced.
This enhanced hardened oil flavor generally enhances the original hardened oil flavor, and in particular has an effect of imparting sweetness and richness peculiar to the hardened oil. In addition, when the fats and oils are used for heating applications such as frying, the strength of the hardened oil flavor hardly changes over time, and it has a long-lasting and excellent effect.
本発明は下記1〜7を提供する。
<1> 部分水素添加油脂を、100℃〜240℃の温度で空気を吹き込みながら加熱酸化する工程(1)、
工程(1)で得られた加熱酸化された部分水素添加油脂を、220℃以下で真空水蒸気蒸留する工程(2)、
を含む、硬化油風味強化用油脂の製造方法。
<2> 工程(1)を少なくとも1時間行うことを特徴とする、上記<1>記載の硬化油風味強化用油脂の製造方法。
<3> 部分水素添加油脂のヨウ素価が50〜100である、上記<1>または<2>記載の硬化油風味強化用油脂の製造方法。
<4> 以下の式(1)で表されるTotox値が24.5以上でありかつ過酸化物価(POV)が8以下の部分水素添加油脂である、硬化油風味強化用油脂:
(POV×2+AnV)(1)
式中、POVは過酸化物価を表し、AnVはアニシジン価を表す。
<5> 酸価が0.1以上である、上記<4>記載の硬化風味強化用油脂。
<6> 上記<4>または<5>に記載の油脂を0.1〜10質量%含み、かつ全構成脂肪酸中のトランス脂肪酸含量が3質量%以下である、硬化油風味を有する食用油脂組成物。
<7> 上記<6>記載の硬化油風味を有する食用油脂組成物を用いて製造される硬化油風味が強化された食品。
The present invention provides the following items 1 to 7.
<1> Step (1) of partially oxidizing hydrogenated oil by heating and oxidizing air at a temperature of 100 ° C. to 240 ° C.,
A step (2) of subjecting the heat-oxidized partially hydrogenated oil obtained in the step (1) to vacuum steam distillation at 220 ° C. or lower;
The manufacturing method of fats and oils for hardening oil flavor reinforcement | strengthening containing.
<2> The method for producing a hardened oil flavor-enhancing fat according to <1>, wherein the step (1) is performed for at least 1 hour.
<3> The method for producing a fat for enhancing a cured oil flavor according to the above <1> or <2>, wherein the iodine value of the partially hydrogenated fat is 50 to 100.
<4> Fats and oils for enhancing hardened oil flavor, wherein the Totox value represented by the following formula (1) is 24.5 or more and the peroxide value (POV) is a partially hydrogenated oil or fat:
(POV × 2 + AnV) (1)
In the formula, POV represents a peroxide value, and AnV represents an anisidine value.
<5> The fat and oil for hardening flavor enhancement according to the above <4>, wherein the acid value is 0.1 or more.
<6> Edible oil composition having a hardened oil flavor, containing 0.1 to 10% by mass of the oil and fat according to <4> or <5>, and having a trans fatty acid content of 3% by mass or less in all constituent fatty acids. object.
<7> A food with an enhanced cured oil flavor produced using the edible oil / fat composition having the cured oil flavor described in <6> above.
本発明の硬化油風味強化用油脂を用いることにより、水素添加油脂由来の好ましい風味が強く、かつ酸化安定性があり、更にトランス脂肪酸含有量が低下した食用油脂組成物及び食品を提供することができる。 By using the oil and fat for hardening oil flavor enhancement of the present invention, it is possible to provide an edible oil and fat composition and food having a strong flavor derived from hydrogenated oil and fat, strong oxidation stability, and further reduced trans fatty acid content. it can.
(硬化油風味強化用油脂)
本発明の硬化油風味強化用油脂は、以下の式(1)で表されるTotox値が24.5以上でかつ過酸化物価(POV)が8以下の部分水素添加油脂である:
POV×2+AnV (1)
式中、POVは過酸化物価を表し、AnVはアニシジン価を表す。
Totox値(Totox Value,TVともいう)は、油脂の酸化により生成する過酸化物とその分解で生じる二次生成物である特定のアルデヒド化合物の存在を考慮して作製された評価方法である(Journal of the American Oil Chemistry Society, Vol 51, pp17-21 (1974))。従来、油脂の劣化などの品質判定に使用されることが多いが、本発明者らは、部分水素添加油脂における硬化油風味がTotox値と過酸化物価と一定の関係にあることを実験的に見いだし、本願発明を完成した。
本願発明において、Totox値は24.5以上である。より好ましくは27以上80以下であり、更に好ましくは29以上55以下である。
(Hard oil for enhancing flavor of hardened oil)
The oil and fat for hardening oil flavor enhancement of the present invention is a partially hydrogenated oil and fat having a Totox value represented by the following formula (1) of 24.5 or more and a peroxide value (POV) of 8 or less:
POV × 2 + AnV (1)
In the formula, POV represents a peroxide value, and AnV represents an anisidine value.
The Totox value (also referred to as Totox Value, TV) is an evaluation method created in consideration of the presence of a specific aldehyde compound, which is a secondary product generated by decomposition of a peroxide generated by oxidation of fats and oils ( Journal of the American Oil Chemistry Society, Vol 51, pp17-21 (1974)). Conventionally, it is often used for quality judgment such as fat and oil degradation, but the present inventors experimentally confirmed that the hydrogenated oil flavor in partially hydrogenated fats and oils has a certain relationship between the Totox value and the peroxide value. As a result, the present invention has been completed.
In the present invention, the Totox value is 24.5 or more. More preferably, it is 27 or more and 80 or less, More preferably, it is 29 or more and 55 or less.
「過酸化物価」とは、油脂の自動酸化の初期に生じる一次生成物である過酸化物の量を表す。ヨウ化カリウムを試料と反応させ、油脂中のヒドロペルオキシドによってヨウ化カリウムから遊離するヨウ素を滴定することにより測定することができる。より詳細には、日本油化学会編「基準油脂試験分析法」(1996年)の「2.5.2.1」(暫4-2000)に記載の方法に従って測定することができる。本発明において過酸化物価は、式(1)を満たす範囲内で、8以下である。6以下であることがより好ましく、4以下であることが更に好ましい。 The “peroxide value” represents the amount of peroxide, which is a primary product generated in the early stage of fat auto-oxidation. It can be measured by reacting potassium iodide with a sample and titrating iodine liberated from potassium iodide with hydroperoxide in the oil. In more detail, it can be measured according to the method described in “2.5.2.1” (provisional 4-2000) of “Reference Oil and Fat Test Analysis Method” (1996) edited by Japan Oil Chemists' Society. In the present invention, the peroxide value is 8 or less within a range satisfying the formula (1). It is more preferably 6 or less, and still more preferably 4 or less.
「アニシジン価」とは、酢酸の存在下でp−メトキシアニリン(p−アニシジン)と反応して生じる黄色の色素を比色してその吸光度により表される値である。特定のアルデヒド化合物の存在を示している。測定方法は、日本油化学会編「基準油脂試験分析法」(1996年)の「2.5.3アニシジン価」に記載の方法で測定することができる。本発明において、アニシジン価は、上記式(1)を満たす範囲内で、10以上であることが好ましく、20以上であることがより好ましく、24.5以上60以下であることが更に好ましく、28以上53以下であることが最も好ましい。 The “anisidine value” is a value represented by the absorbance of a yellow dye produced by reaction with p-methoxyaniline (p-anisidine) in the presence of acetic acid. The presence of a specific aldehyde compound is indicated. The measuring method can be measured by the method described in “2.5.3 Anisidine value” of “Standard oil and fat test analysis method” (1996) edited by Japan Oil Chemists' Society. In the present invention, the anisidine value is preferably 10 or more, more preferably 20 or more, still more preferably 24.5 or more and 60 or less, within the range satisfying the above formula (1). Most preferably, it is 53 or less.
「酸価」とは、試料1g中に含まれている遊離脂肪酸を中和するのに要する水酸化カリウムのmg数をいう。酸価は、日本油化学会編「基準油脂試験分析法」(1996年)の「2.3.1酸価」に記載の方法に従って測定することができる。本発明において酸価は、0.1以上であることが好ましい。0.1以上0.6以下であることがより好ましい。 “Acid value” refers to the number of mg of potassium hydroxide required to neutralize free fatty acids contained in 1 g of a sample. The acid value can be measured according to the method described in “2.3.1 Acid value” of “Standard oil and fat test analysis method” (1996) edited by Japan Oil Chemists' Society. In the present invention, the acid value is preferably 0.1 or more. More preferably, it is 0.1 or more and 0.6 or less.
本発明の硬化油風味強化用油脂のC18−1(トランス体+シス体)脂肪酸の量は、全脂肪酸量に対し、45質量%以上であることが好ましく、50〜78質量%であることがより好ましい。また、C18−2(トランス体+シス体)脂肪酸の量は、全脂肪酸量に対し、10質量%未満であることが好ましく、7質量%以下であることが更に好ましい。 The amount of C18-1 (trans isomer + cis isomer) fatty acid in the oil for enhancing a cured oil flavor of the present invention is preferably 45% by mass or more, and preferably 50 to 78% by mass with respect to the total fatty acid amount. More preferred. The amount of C18-2 (trans isomer + cis isomer) fatty acid is preferably less than 10% by mass and more preferably 7% by mass or less based on the total amount of fatty acids.
本発明の硬化油風味強化用油脂を得るための原料である部分水素添加油脂を製造するための食用油脂は、例えば、コーン油、大豆油、ナタネ油、サフラワー油、米油、綿実油、サンフラワー油、魚油、パーム油、パーム油分別軟質油またはこれらの2種以上の混合物が挙げられる。 Edible fats and oils for producing partially hydrogenated fats and oils that are raw materials for obtaining the fats and oils for enhancing the hardened oil flavor of the present invention include, for example, corn oil, soybean oil, rapeseed oil, safflower oil, rice oil, cottonseed oil, sunflower oil Examples thereof include flower oil, fish oil, palm oil, palm oil fractionated soft oil, or a mixture of two or more thereof.
なお、これらの原料油脂は、脱色油、精製油を用いることができる。脱色油とは搾油後、脱ガム・脱酸・脱色の工程を経た油脂、精製油とは脱色後脱臭工程まで経た油脂である。これらの工程は例えば、「食用油脂製造の実際」(幸書房、昭和63年7月5日発行)の“3精製工程の実際”に記載されている方法等、当業者が通常行う方法を適用してもよい。 In addition, decoloring oil and refined oil can be used for these raw material fats and oils. Decolorized oil is oil that has been subjected to degumming, deoxidation, and decolorization processes after oil extraction, and refined oil is oil that has been subjected to deodorization process after decolorization. For these steps, for example, methods commonly used by those skilled in the art are applied, such as the method described in “3 Practice of purification steps” in “Actual production of edible fats and oils” (issued on July 5, 1988). May be.
本明細書において硬化油風味強化用油脂の原料油脂として用いられる「部分水素添加油脂」とは、食用油脂あるいは二種以上のその混合油脂を「部分水素添加処理」を行った油脂を意味する。
「部分水素添加処理」は、本分野において公知の方法で行うことができるが、水素圧力0.05〜2.0MPa、触媒中のニッケル含量0.005〜0.3%、反応開始温度が120〜200℃という条件下で行うことができる。例えば、水素圧力0.5MPa、触媒中のニッケル含量0.04%、反応開始温度150℃で行うことができる。なお、本明細書において、「部分水素添加処理」とは、完全水素添加処理ではない水素添加処理、あるいは不飽和結合が残存するように行う水素添加処理を意味する。
本発明では、食用油脂あるいは二種以上のその混合油脂を好ましくはヨウ素化50〜100、更に好ましくは65〜80の範囲になるまで部分水素添加処理を行った部分水素添加油脂を使用することが好ましい。
In the present specification, the “partially hydrogenated fats and oils” used as the raw material fats and oils for enhancing the hardened oil flavor means fats and oils obtained by performing “partial hydrogenation treatment” on edible fats and oils or two or more of the mixed fats and oils.
The “partial hydrogenation treatment” can be performed by a method known in the art, but the hydrogen pressure is 0.05 to 2.0 MPa, the nickel content in the catalyst is 0.005 to 0.3%, and the reaction start temperature is 120. It can carry out on the conditions of -200 degreeC. For example, it can be carried out at a hydrogen pressure of 0.5 MPa, a nickel content in the catalyst of 0.04%, and a reaction start temperature of 150 ° C. In the present specification, the “partial hydrogenation treatment” means a hydrogenation treatment that is not a complete hydrogenation treatment or a hydrogenation treatment that is performed so that unsaturated bonds remain.
In the present invention, it is possible to use a partially hydrogenated oil or fat obtained by subjecting an edible oil or fat or a mixture of two or more thereof to a partial hydrogenation treatment until preferably in the range of 50 to 100, more preferably 65 to 80. preferable.
部分水素添加油脂のトランス脂肪酸含量が、部分水素添加油脂の構成脂肪酸の全質量に対して好ましくは10〜60質量%、より好ましくは20〜55質量%となるように、部分水素添加処理を行うことが好ましい。トランス脂肪酸含量が一定量となった部分水素添加油脂は、ヨウ素価50〜100、好ましくは65〜80となるように水素添加処理を行ってから、トランス脂肪酸含量を測定して、トランス脂肪酸含量が一定量となっている油脂を選択することにより得ることができる。
トランス脂肪酸含量は、例えば、日本油化学会編「基準油脂試験分析法」(2007年)に記載の「トランス脂肪酸含量(キャピラリーガスクロマトグラフ法)」により決定することができる。
The partial hydrogenation treatment is performed so that the trans fatty acid content of the partially hydrogenated fat / oil is preferably 10 to 60% by mass, more preferably 20 to 55% by mass with respect to the total mass of the constituent fatty acids of the partially hydrogenated fat / oil. It is preferable. Partially hydrogenated fats and oils having a constant trans fatty acid content are subjected to hydrogenation treatment so that the iodine value is 50 to 100, preferably 65 to 80, and the trans fatty acid content is measured. It can be obtained by selecting a certain amount of fats and oils.
The trans fatty acid content can be determined by, for example, “trans fatty acid content (capillary gas chromatograph method)” described in “Oil and Fat Test Analysis Method” (2007) edited by Japan Oil Chemists' Society.
(硬化油風味強化用油脂の製造方法)
本発明の硬化油風味強化用油脂は、上述した部分水素添加油脂に対し、100℃〜240℃の温度で空気を吹き込みながら加熱酸化した後、220℃以下で真空水蒸気蒸留して得ることができる。
加熱酸化は、100℃〜240℃の温度で行うことが好ましい。より好ましくは150℃〜200℃で加熱し、更に好ましくは170℃〜190℃で加熱する。
上記の温度で加熱しながら、空気を100〜1000ml/分の吹き込み量で、少なくとも1時間加熱酸化を行うことが好ましい。加熱酸化時間は、より好ましくは1〜15時間、更に好ましくは2〜12時間、最も好ましくは2〜10時間である。
空気の吹き込み方法は、従来公知の方法が挙げられるが、例えば油脂を攪拌しながらエアーポンプを用いて一定量の空気を油脂中に吐出する方法が挙げられる。
(Method for producing fats and oils for enhancing hardened oil flavor)
The oil for enhancing the flavor of hydrogenated oil according to the present invention can be obtained by subjecting the above-mentioned partially hydrogenated oil and fat to heat oxidation while blowing air at a temperature of 100 ° C to 240 ° C, followed by vacuum steam distillation at 220 ° C or lower. .
The thermal oxidation is preferably performed at a temperature of 100 ° C to 240 ° C. More preferably, it heats at 150 to 200 degreeC, More preferably, it heats at 170 to 190 degreeC.
While heating at the above temperature, it is preferable to carry out heat oxidation at a rate of blowing air of 100 to 1000 ml / min for at least 1 hour. The heating oxidation time is more preferably 1 to 15 hours, further preferably 2 to 12 hours, and most preferably 2 to 10 hours.
The air blowing method may be a conventionally known method, and for example, a method of discharging a certain amount of air into the oil or fat using an air pump while stirring the oil or fat.
真空水蒸気蒸留とは、食用油脂の分野で通常行われる「脱臭工程」として、高真空下、高温に加熱された油脂中にスチームを吹き込み、有臭成分や、脂肪酸、不けん化物などの揮発成分を蒸留する方法である。
真空水蒸気蒸留装置には、バッチ式、半連続式、連続式などがあるが、いずれの装置を用いてもよい。
Vacuum steam distillation is a “deodorization process” normally performed in the field of edible fats and oils. Steam is blown into fats and oils heated to high temperature under high vacuum, and volatile components such as odorous components, fatty acids, and unsaponifiable substances. Is a method of distilling.
The vacuum steam distillation apparatus includes a batch type, a semi-continuous type, and a continuous type, and any apparatus may be used.
真空水蒸気蒸留の温度は220℃以下で行うことが好ましい。より好ましくは120℃〜220℃であり、更に好ましくは150〜210℃である。真空度は、好ましくは800Pa以下、より好ましくは600Pa以下であり、更に好ましくは133〜600Paある。使用する機器によっては500Pa以下で行ってもよい。真空水蒸気蒸留の時間は、好ましくは0.5〜2時間であり、より好ましくは1時間である。 The temperature of the vacuum steam distillation is preferably performed at 220 ° C. or lower. More preferably, it is 120 degreeC-220 degreeC, More preferably, it is 150-210 degreeC. The degree of vacuum is preferably 800 Pa or less, more preferably 600 Pa or less, and still more preferably 133 to 600 Pa. Depending on the equipment used, it may be performed at 500 Pa or less. The time for vacuum steam distillation is preferably 0.5 to 2 hours, more preferably 1 hour.
本発明において、硬化油風味強化用油脂を製造するには、上記部分水素添加した後、水蒸気蒸留処理の前または後に、好ましくは水蒸気蒸留処理の前に、更に脱色処理を行うことが好ましい。
脱色処理とは通常、油脂中の色素を吸着等により脱色する処理のことをいう。公知の方法を使用することができるが、例えば、油脂に、油脂全質量に対して0.1〜4質量%程度の活性白土を添加して、常圧または減圧下で、油脂を60〜120℃で、5〜60分程度加熱することにより行うことができる。その後、ろ過により活性白土を除去する。
In the present invention, in order to produce a hardened oil flavor-enhancing fat, it is preferable to further perform a decolorization treatment after the partial hydrogenation and before or after the steam distillation treatment, preferably before the steam distillation treatment.
The decoloring process generally means a process of decolorizing the pigment in the oil by adsorption or the like. Although a well-known method can be used, for example, about 0.1-4 mass% activated clay is added to fats and oils with respect to fats and oils total weight, and fats and oils are 60-120 under normal pressure or pressure reduction. It can carry out by heating at 5 degreeC for about 5 to 60 minutes. Thereafter, the activated clay is removed by filtration.
(硬化油風味強化用油脂を添加した油脂組成物)
硬化油風味強化用油脂は、他の油脂と混合して、硬化油風味が増強された食用油脂組成物を製造することができる。
例えば、硬化油風味強化用油脂をトランス脂肪酸の少ない油脂(例えばパーム油系油脂)に対し、油脂全質量に対して好ましくは0.1〜10質量%、好ましくは0.5〜7質量%、更に好ましくは1〜5質量%の量で添加することにより、トランス脂肪酸量を増やすことなく、硬化油風味を付与することができる。
硬化油風味の付与は、硬化油風味全体を付与するものであるが、特に硬化油特有の甘さ、コクを付与する効果がある。加えてフライなどの用途として加熱された場合の持続性がある。
(Oil composition to which oil for enhancing hardened oil flavor is added)
The hardened oil flavor-enhancing fats and oils can be mixed with other fats and oils to produce an edible fat composition with enhanced hardened oil flavor.
For example, the fat and oil for enhancing the hardened oil flavor is preferably 0.1 to 10% by mass, preferably 0.5 to 7% by mass, based on the total mass of the oil and fat, with respect to the oil and fat having low trans fatty acid (for example, palm oil-based oil and fat) More preferably, by adding in an amount of 1 to 5% by mass, a hardened oil flavor can be imparted without increasing the amount of trans fatty acid.
The imparting of the hardened oil flavor imparts the entire hardened oil flavor, and is particularly effective in imparting the sweetness and richness peculiar to the hardened oil. In addition, there is persistence when heated for applications such as frying.
硬化油風味強化用油脂と混合する他の油脂中の「ポリ不飽和脂肪酸」は、20質量%以下であることが好ましい。ポリ不飽和脂肪酸が、20質量%を越えると、水素添加油脂由来の風味が弱まる場合がある。ポリ不飽和脂肪酸が20質量%以下の油脂としては、(i)パーム系油脂、(ii)ラウリン系油脂または(iii)パーム系油脂及びラウリン系油脂の組み合わせ、(v)ラウリン系油脂のエステル交換油脂、及び(vi)パーム系油脂とラウリン系油脂の混合物のエステル交換油脂から選択される少なくとも一つを含む油脂であることが好ましい。 The “polyunsaturated fatty acid” in other oils and fats to be mixed with the oil for enhancing hardened oil flavor is preferably 20% by mass or less. When polyunsaturated fatty acid exceeds 20 mass%, the flavor derived from hydrogenated fats and oils may become weak. Examples of fats and oils having a polyunsaturated fatty acid of 20% by mass or less include (i) palm-based fats and oils, (ii) lauric fats and oils or (iii) a combination of palm-based fats and lauric fats and oils, and (v) transesterification of lauric fats and oils. It is preferable that it is fat and oil containing at least one selected from fats and oils and (vi) the transesterified fats and oils of the mixture of palm fats and lauric fats and oils.
パーム系油脂としては、パーム油、分別パーム油およびこれら1種以上をエステル交換した油脂が挙げられる。
また、ラウリン系油脂としては、パーム核油、やし油、パーム核分別油およびこれらの完全水素添加油及びこれら1種以上をエステル交換した油脂が挙げられる。
また、パーム系油脂とラウリン系油脂を混合したもの、あるいは混合物をエステル交換した油脂を用いることも可能である。
分別パーム油とは、パーム油を分別処理し、得られた高融点画分、中融点画分もしくは低融点画分の油脂を意味する。また、得られた画分をさらに分別したものを使用することもできる。
Examples of palm oils and fats include palm oil, fractionated palm oil, and oils and fats obtained by transesterifying one or more of these.
In addition, examples of lauric fats and oils include palm kernel oil, palm oil, palm kernel fractionated oil, and these completely hydrogenated oils, and fats and oils obtained by transesterifying one or more of these.
Moreover, it is also possible to use what mixed palm-type fats and oils and lauric-type fats, or the fats and oils which transesterified the mixture.
Fractionated palm oil means oils and fats obtained by fractionating palm oil and obtained, a high melting point fraction, a middle melting point fraction or a low melting point fraction. Moreover, what further fractionated the obtained fraction can also be used.
本発明の硬化油風味強化用油脂を添加して得られる本発明の油脂組成物のトランス脂肪酸含量は、3質量%以下であることが好ましい。 It is preferable that the trans fatty acid content of the oil / fat composition of the present invention obtained by adding the oil / fat for enhancing the hardened oil flavor of the present invention is 3% by mass or less.
本発明の油脂組成物は、例えば、フライドポテト、ドーナツなどの油ちょう食品、あるいは、パン、クッキー、ビスケット、パイなどの加熱調理食品、あるいは、ホイップクリーム、コーヒークリーム、アイスクリームなどのクリーム類等の油脂を含む食品への利用が挙げられる。その他、チョコレート及び上記食品を用いたプリンやケーキ類などのチルドデザートなどにも利用できる。 The oil and fat composition of the present invention includes, for example, oily foods such as French fries and donuts, cooked foods such as bread, cookies, biscuits and pies, or creams such as whipped cream, coffee cream and ice cream Use for foods containing oils and fats. In addition, it can also be used for chilled desserts such as puddings and cakes using chocolate and the above foods.
〈実施例1〜12および比較例1〜7〉
部分水素添加油脂(コーン油70質量%+大豆油30質量%)(ヨウ素化:75、トランス脂肪酸(C18−1+18−2)34質量%、C18−1(トランス体+シス体):71質量%、C18−2(トランス体+シス体):6質量%)に空気を500ml/分で吹き込みながら表1〜3に記載の所定の温度で各時間加熱したものをさらに所定の温度で真空水蒸気蒸留し、実施例1〜12及び比較例1〜4の油脂組成物を得た。この時、真空度は500〜600Paであった。
実施例3と同様に空気を500ml/分で吹き込みながら加熱し、真空水蒸気蒸留を行わなかったものを比較例6とした。
大豆油に空気を500ml/分で吹き込みながら134℃で1.5時間加熱し、真空水蒸気蒸留を行わなかったものを比較例5とした。
<Examples 1-12 and Comparative Examples 1-7>
Partially hydrogenated fat (corn oil 70% by mass + soybean oil 30% by mass) (iodination: 75, trans fatty acid (C18-1 + 18-2) 34% by mass, C18-1 (trans isomer + cis isomer): 71% by mass , C18-2 (trans isomer + cis isomer): 6% by mass), heated at a predetermined temperature shown in Tables 1 to 3 while blowing air at 500 ml / min, and further subjected to vacuum steam distillation at a predetermined temperature. And the oil-fat composition of Examples 1-12 and Comparative Examples 1-4 was obtained. At this time, the degree of vacuum was 500 to 600 Pa.
In the same manner as in Example 3, heating was performed while blowing air at 500 ml / min, and vacuum steam distillation was not performed.
Comparative Example 5 was obtained by heating at 134 ° C. for 1.5 hours while blowing air into soybean oil at 500 ml / min and not performing vacuum steam distillation.
得られた各油脂について、下記の方法により、過酸化物価(POV)、酸価(AV)、アニシジン価(AnV)、及びトランス脂肪酸量を測定した。
<過酸化物価(POV)の測定>
試料0.5〜5gを共栓付き三角フラスコに正しくはかり取る。酢酸:2,2,4‐トリメチルペンタン(イソオクタン=3:2(vol%)に混合した溶剤50mlを加え、静かに振り混ぜて試料を溶解する。窒素ガスでフラスコ内の空気を穏やかに置換する。さらに窒素ガスを通しながら飽和ヨウ化カリウム溶液0.1mlを加える。ただちに栓をし、1分連続して円を描くように振りませる。水30mlを加え、栓をして5〜10秒激しく振り混ぜる。0.01mol/Lチオ硫酸ナトリウム標準液で1ml容量ビューレットを使い滴定する。測定液が微黄色を呈したら、でんぷん溶液約0.5mlを加えて滴定を続け、滴定液の青色が消失するときを終点する。あらかじめ空試験を行い、でんぷん溶液を加えて発色しないことを確認する。下記の式により計算し過酸化物価を求める。
過酸化物価(meq/kg)=(0.01mol/Lチオ硫酸ナトリウム標準液使用量(ml)×0.01mol/Lチオ硫酸ナトリウム標準液のファクター×10)/試料採取量(g)
About each obtained fats and oils, the peroxide value (POV), the acid value (AV), the anisidine value (AnV), and the amount of trans fatty acids were measured by the following method.
<Measurement of peroxide value (POV)>
Weigh correctly 0.5-5 g of sample into Erlenmeyer flask with stopper. Add 50 ml of solvent mixed with acetic acid: 2,2,4-trimethylpentane (isooctane = 3: 2 (vol%), and gently shake to dissolve the sample.Air in the flask is gently replaced with nitrogen gas Add 0.1 ml of saturated potassium iodide solution while passing nitrogen gas, immediately plug and shake for 1 minute in a circle, add 30 ml of water, plug and vigorously for 5-10 seconds. Titrate with 1 mol volume burette with 0.01 mol / L sodium thiosulfate standard solution.If the measuring solution shows a slight yellow color, add about 0.5 ml of starch solution and continue titration. When the disappearance ends, perform a blank test in advance, add starch solution to confirm that no color develops, and calculate the peroxide value by the following formula.
Peroxide value (meq / kg) = (0.01 mol / L sodium thiosulfate standard solution usage (ml) × 0.01 mol / L sodium thiosulfate standard solution factor × 10) / sample amount (g)
<酸価(AV)の測定>
試料0.1〜20.0gを三角フラスコに正しくはかり取る。イソプロピルアルコール:ジエチルエーテル=1:1に混合し中性に調製した中性溶剤100mlを加え試料を溶解する。0.1mol/L水酸化カリウム標準液で10ml容量ビューレットを使い滴定し、フェノールフタレイン指示薬が微紅色を呈して30秒続いたときを中和の終点として測定する。下記の式により計算し酸価を求める。
酸価=(5.611×0.1mol/L水酸化カリウム標準液の使用量(ml)×0.1mol/L水酸化カリウム標準液のファクター)/試料採取量(g)
<Measurement of acid value (AV)>
Weigh correctly 0.1-20.0 g of sample into Erlenmeyer flask. Add 100 ml of neutral solvent mixed in isopropyl alcohol: diethyl ether = 1: 1 and neutralize to dissolve the sample. Titrate with a 0.1 mol / L potassium hydroxide standard solution using a 10 ml volume burette, and measure when the phenolphthalein indicator shows a slight red color and lasts for 30 seconds as the end point of neutralization. Calculate the acid value by the following formula.
Acid value = (5.611 × 0.1 mol / L potassium hydroxide standard solution used (ml) × 0.1 mol / L potassium hydroxide standard solution factor) / sample amount (g)
<アニシジン価(AnV)の測定>
試料0.1〜4.0gを25mlのメスフラスコに精秤し、2,2,4−トリメチルペンタン(イソオクタン)で完全に溶解してから標線まで希釈し、よく振り混ぜ試料溶液とする。先ず試料溶液の吸光度を測定する。試料溶液を吸収セルに取り、イソオクタンを対照として波長350nmの吸光度を測定する(B)(吸光度の測定には島津製作所吸光度計UV‐160を使用)。次にp‐アニシジンと反応後の吸光度を測定する。試料溶液5mlを正しく10ml試験管に取り、別の試験管に空試験用としてイソオクタン5mlを正しく取る。0.25g/100mlp‐アニシジン−酢酸溶液1mlを正しく取り、各試験管に加え振り混ぜる。正確に10分後、空試験溶液を対照として、波長350nmの吸光度を測定する(A)。下記の式により計算しアニシジン価を求める。
アニシジン価=25×(1.2×A−B)/試料溶液25ml中の試料量(g)
<Measurement of anisidine value (AnV)>
Weigh accurately 0.1 to 4.0 g of sample into a 25 ml volumetric flask, dissolve completely with 2,2,4-trimethylpentane (isooctane), dilute to the marked line, and shake well to obtain a sample solution. First, the absorbance of the sample solution is measured. The sample solution is taken in an absorption cell, and the absorbance at a wavelength of 350 nm is measured using isooctane as a control (B) (Shimadzu Corporation Absorbance Meter UV-160 is used for measuring the absorbance). Next, the absorbance after reaction with p-anisidine is measured. Correctly take 5 ml of the sample solution in a 10 ml test tube, and correctly take 5 ml of isooctane for the blank test in another test tube. Correctly take 1 ml of 0.25 g / 100 ml p-anisidine-acetic acid solution, add to each tube and shake. Exactly 10 minutes later, the absorbance at a wavelength of 350 nm is measured using the blank test solution as a control (A). Calculate the anisidine value by the following formula.
Anisidine value = 25 × (1.2 × A−B) / sample amount in 25 ml of sample solution (g)
<トランス脂肪酸量の測定>
試料20〜50mgをねじ口試験に精秤する。0.5mol/L水酸化ナトリウム−メタノール溶液1mlを加える。密栓し、油滴が消失して均一な溶液になるまで100℃で5〜10分加熱する。放冷後、三フッ化ホウ素−メタノール試薬1mlを加え、密栓して100℃で5分間加熱する。放冷後、ヘキサン2〜5ml加え(試料濃度約1%)、さらに飽和食塩水約7mlを加え、密栓して良く振とうする。ヘキサン層を採取し、少量の無水硫酸ナトリウムで脱水し、試料溶液とする。試料溶液を島津製作所製ガスクロマトグラフGC‐2010を使用し、下記の条件で測定する。
カラム:SUPELCO社製 SP‐2560 内径0.25mm、長さ100m、膜厚0.2μm
注入方式:スプリット方式
検出器:FID
キャリアガス:ヘリウム
スプリット比:100:1
注入口温度:250℃
検出器温度:250℃
注入量:1μl
カラム流量:1ml/min
カラム温度:180℃一定
検出された各ピークはデータ処理システムを使用して積分処理し、面積を求めて面積%を求め、さらに0.95を乗じてg/100gの質量%に換算して含有量とした。
表1〜3における「トランス脂肪酸量」は、18−1トランス脂肪酸と18−2トランス脂肪酸の合計量を意味する。
<Measurement of trans fatty acid content>
20-50 mg of sample is precisely weighed for screw mouth test. Add 1 ml of 0.5 mol / L sodium hydroxide-methanol solution. Seal and heat at 100 ° C. for 5-10 minutes until the oil droplets disappear and become a homogeneous solution. After allowing to cool, 1 ml of boron trifluoride-methanol reagent is added, sealed and heated at 100 ° C. for 5 minutes. After standing to cool, add 2 to 5 ml of hexane (sample concentration about 1%), add about 7 ml of saturated saline, seal tightly and shake well. The hexane layer is collected and dehydrated with a small amount of anhydrous sodium sulfate to obtain a sample solution. The sample solution is measured using a gas chromatograph GC-2010 manufactured by Shimadzu Corporation under the following conditions.
Column: SP-2560 manufactured by SUPELCO, Inner diameter 0.25 mm, Length 100 m, Film thickness 0.2 μm
Injection method: Split method Detector: FID
Carrier gas: helium Split ratio: 100: 1
Inlet temperature: 250 ° C
Detector temperature: 250 ° C
Injection volume: 1 μl
Column flow rate: 1 ml / min
Column temperature: constant 180 ° C. Each detected peak is integrated using a data processing system, the area is obtained to obtain area%, and further multiplied by 0.95 to be converted to g / 100 g mass%. The amount.
The “trans fatty acid amount” in Tables 1 to 3 means the total amount of 18-1 trans fatty acid and 18-2 trans fatty acid.
実施例1〜12及び比較例1〜5の油脂組成物をそれぞれ1質量%(トランス脂肪酸(C18−1+18−2)量は約0.3質量%)、パーム油を99質量%混合して加熱調理用油脂組成物を作製した。また、比較例6として、部分水素添加していない大豆油を加熱処理し、真空水蒸気蒸留処理していないものを1質量%配合したパーム油を用いた。また、比較例7は、コントロールとして、コーン油:大豆油=70:30配合油の部分水素添加油(ヨウ素化75)(加熱酸化処理をせず、通常の250℃で水蒸気蒸留をしたもの)を1質量%配合したパーム油を用いた。パーム油は精製パーム油を使用した。また、硬化油風味標準品として、コーン油:大豆油=70:30配合油の部分水素添加油(ヨウ素化75)100%(トランス脂肪酸(C18−1+18−2)34質量%)を用いた。 1% by mass of each of the oil and fat compositions of Examples 1 to 12 and Comparative Examples 1 to 5 (the amount of trans fatty acid (C18-1 + 18-2) is about 0.3% by mass) and 99% by mass of palm oil are mixed and heated. A cooking oil / fat composition was prepared. Further, as Comparative Example 6, palm oil was used in which soybean oil that had not been partially hydrogenated was heat-treated and 1% by mass of what was not vacuum steam distilled. In Comparative Example 7, as a control, a partially hydrogenated oil of corn oil: soybean oil = 70: 30 blended oil (iodinated 75) (no steam oxidation treatment and steam distillation at normal 250 ° C.) Used was 1% by mass of palm oil. The palm oil used refined palm oil. Moreover, 100% of partially hydrogenated oil (iodinated 75) of corn oil: soybean oil = 70: 30 blended oil (trans fatty acid (C18-1 + 18-2) 34% by mass) was used as a hardened oil flavor standard product.
実施例1〜12及び比較例1〜7並びに硬化風味標準品から上述のとおり作製した加熱調理用油脂組成物を用いて市販のプレフライ済み冷凍チキンナゲットを180℃で3.5分間フライ調理し、風味標準品の硬化油風味を標準として、官能評価を行った。官能評価は、良く訓練された5人のパネラーにより行われ、以下の基準で点数化し、その平均値を評価値とした。3点以上を合格点とする。結果は表1〜3の「官能評価」欄に示した。
また、以下の式によりTotox値を求めた。
(POV×2+AnV)(1)(式中、POVは過酸化物価を表し、AnVはアニシジン価を表す。)
Commercially cooked pre-fried frozen chicken nuggets were cooked at 180 ° C. for 3.5 minutes using Examples 1-12 and Comparative Examples 1-7 and the oil and fat composition for cooking prepared as described above from the cured flavor standard, and flavored. Sensory evaluation was carried out using the standard hardened oil flavor as a standard. The sensory evaluation was performed by five well-trained panelists, scored according to the following criteria, and the average value was used as the evaluation value. A score of 3 or more is considered a passing score. The results are shown in the “sensory evaluation” column of Tables 1 to 3.
Moreover, the Totox value was calculated | required with the following formula | equation.
(POV × 2 + AnV) (1) (wherein POV represents a peroxide value and AnV represents an anisidine value)
標準品と同等の硬化油風味を有する 5点
標準品よりわずかに弱いが、充分な硬化油風味を有する 4点
標準品より少し硬化油風味が弱い 3点
標準品より硬化油風味が弱い 2点
標準品より明らかに硬化油風味が弱い 1点
5 points with a hardened oil flavor equivalent to the standard product Slightly weaker than the standard product, but 4 points with sufficient hardened oil flavor 3 points A little hardened oil flavor than the standard product 3 points A hardened oil flavor is weaker than the standard product 2 points 1 point that the oil flavor is weaker than the standard product
表3から明らかなとおり、本発明の製造方法により製造された硬化油風味強化用油脂あるいは本発明の所定のパラメータを満たす硬化油風味強化用油脂を含む油脂組成物から製造したプレフライ済み冷凍チキンナゲットを調理した場合、標準品と同等の硬化油風味評価が得られた(実施例1〜12)。特にTotox値が24.5以上でかつ過酸化物価が8以下のものの風味評価が良かった。
一方、本発明の製造方法の条件を満たさない方法で得られた油脂では風味評価が低くなった(比較例1〜6)。特に、部分水素添加油脂を、100℃〜240℃の温度で空気を吹き込みながら加熱酸化する工程(1)を行わない場合(比較例4)、POV値及びアニシジン価共に低く、その結果Totox値が低くなり、風味評価が低くくなった。また、加熱酸化された部分水素添加油脂を、220℃以下で真空水蒸気蒸留する工程(2)を行わない場合には、加熱酸化温度に関わらずPOV値が増加し、劣化臭により風味評価が低くなった(比較例5)。部分水素添加していない加熱された油脂を220℃以下で真空水蒸気蒸留する工程(2)を行なわない油脂も加熱酸化温度に関わらずPOV値が増加し、劣化臭により風味評価が低くなった(比較例6)。また、加熱酸化工程の温度が低い場合にはTotox値が低くなり、風味評価が低くくなった(比較例1)。真空水蒸気蒸留を220℃を超える温度で行うと、Totox値が低くなり、風味評価が低くくなった(比較例2〜3)。
As is clear from Table 3, a pre-fried frozen chicken nugget produced from an oil / fat composition containing the oil / fat for hardening oil flavor enhancement produced by the production method of the invention or the oil / fat for hardening oil flavor enhancement satisfying the predetermined parameters of the invention is used. When cooked, hardened oil flavor evaluation equivalent to a standard product was obtained (Examples 1 to 12). In particular, the flavor evaluation was good when the Totox value was 24.5 or more and the peroxide value was 8 or less.
On the other hand, in the fats and oils obtained by the method not satisfying the conditions of the production method of the present invention, the taste evaluation was low (Comparative Examples 1 to 6). In particular, when the step (1) in which the partially hydrogenated fat is heated and oxidized while blowing air at a temperature of 100 ° C. to 240 ° C. (Comparative Example 4), both the POV value and the anisidine value are low, and as a result, the Totox value is low. It became low and the flavor evaluation became low. In addition, in the case where the step (2) of vacuum steam distillation at 220 ° C. or less is not performed on the partially oxidized hydrogenated oil that has been heated and oxidized, the POV value increases regardless of the heating oxidation temperature, and the flavor evaluation is low due to a deteriorated odor. (Comparative Example 5). Oils and fats that are not subjected to the step (2) of vacuum steam distillation of heated oils and fats that have not been partially hydrogenated at 220 ° C. or less have increased POV values regardless of the heating oxidation temperature, and the flavor evaluation has been lowered due to deteriorated odors ( Comparative Example 6). Moreover, when the temperature of the heating oxidation process was low, the Totox value was low, and the flavor evaluation was low (Comparative Example 1). When vacuum steam distillation was performed at a temperature exceeding 220 ° C., the Totox value was lowered and the flavor evaluation was lowered (Comparative Examples 2 to 3).
Claims (8)
工程(1)で得られた加熱酸化された部分水素添加油脂を、150〜220℃で真空水蒸気蒸留する工程(2)、
を含む、硬化油風味強化用油脂の製造方法。 A step (1) in which the partially hydrogenated fat is heated and oxidized while blowing air at a temperature of 150 ° C. to 210 ° C .;
A step (2) of subjecting the partially oxidized hydrogenated oil obtained by the step (1) to vacuum steam distillation at 150 to 220 ° C .;
The manufacturing method of fats and oils for hardening oil flavor reinforcement | strengthening containing.
(POV×2+AnV)(1)
式中、POVは過酸化物価を表し、AnVはアニシジン価を表す。 Fats and oils for enhancing hardened oil flavor, wherein the Totox value represented by the following formula (1) is 24.5 or more and the peroxide value (POV) is a partially hydrogenated oil or fat:
(POV × 2 + AnV) (1)
In the formula, POV represents a peroxide value, and AnV represents an anisidine value.
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| JP5506146B2 (en) * | 2007-10-11 | 2014-05-28 | 日清オイリオグループ株式会社 | Low trans fatty acid oil composition |
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| SG194063A1 (en) * | 2011-05-23 | 2013-11-29 | J Oil Mills Inc | Oil or fat composition |
| CN103748200B (en) * | 2011-08-24 | 2015-07-01 | J-制油株式会社 | Oxidized partially hydrogenated oil |
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| US20230139404A1 (en) * | 2020-03-06 | 2023-05-04 | The Protein Brewery B.V. | Improved single-cell protein production using antioxidants |
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