JPH06327403A - Flavor-added hardened food oil with reduced hydrogenation back small and production process thereof - Google Patents
Flavor-added hardened food oil with reduced hydrogenation back small and production process thereofInfo
- Publication number
- JPH06327403A JPH06327403A JP5140136A JP14013693A JPH06327403A JP H06327403 A JPH06327403 A JP H06327403A JP 5140136 A JP5140136 A JP 5140136A JP 14013693 A JP14013693 A JP 14013693A JP H06327403 A JPH06327403 A JP H06327403A
- Authority
- JP
- Japan
- Prior art keywords
- oil
- hardened
- hydrogenated
- flavor
- odor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000005984 hydrogenation reaction Methods 0.000 title abstract description 22
- 235000013305 food Nutrition 0.000 title abstract description 15
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000796 flavoring agent Substances 0.000 claims abstract description 31
- 235000019634 flavors Nutrition 0.000 claims abstract description 31
- 239000002245 particle Substances 0.000 claims abstract description 7
- 239000003921 oil Substances 0.000 claims description 87
- 239000008157 edible vegetable oil Substances 0.000 claims description 46
- 238000001816 cooling Methods 0.000 claims description 23
- 239000007921 spray Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- 238000005507 spraying Methods 0.000 abstract description 4
- 235000009508 confectionery Nutrition 0.000 abstract description 3
- 235000019640 taste Nutrition 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 description 86
- 239000003925 fat Substances 0.000 description 46
- 235000019197 fats Nutrition 0.000 description 45
- 239000012530 fluid Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 8
- 230000001953 sensory effect Effects 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 7
- 244000068988 Glycine max Species 0.000 description 7
- 239000002285 corn oil Substances 0.000 description 6
- 235000005687 corn oil Nutrition 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 235000014593 oils and fats Nutrition 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000008371 vanilla flavor Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 244000299461 Theobroma cacao Species 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 235000013310 margarine Nutrition 0.000 description 2
- 239000003264 margarine Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000007968 orange flavor Substances 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DVVATNQISMINCX-YTXTXJHMSA-N (E,E)-2,4-Octadienal Chemical compound CCC\C=C\C=C\C=O DVVATNQISMINCX-YTXTXJHMSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 240000003889 Piper guineense Species 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000040738 Sesamum orientale Species 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 235000008693 Triphasia trifolia Nutrition 0.000 description 1
- 244000093965 Triphasia trifolia Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
- 235000019519 canola oil Nutrition 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 239000008370 chocolate flavor Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- -1 for example Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000008369 fruit flavor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229940069445 licorice extract Drugs 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 239000001683 mentha spicata herb oil Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 230000036306 sensory inhibition Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019721 spearmint oil Nutrition 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical group 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
Landscapes
- Edible Oils And Fats (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、微粒化することにより
水添戻り臭を低減したフレーバー添加食用硬化油に関す
る。また、本発明は、微粒化することによって水添戻り
臭を低減したフレーバー添加食用硬化油の製造法に関す
る。本発明の水添戻り臭を低減したフレーバー添加食用
硬化油は、油脂食品、菓子、揚げ油などの原料として有
用である。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a flavored edible hardened oil in which hydrogenated return odor is reduced by atomizing. The present invention also relates to a method for producing a flavor-added hydrogenated edible oil in which hydrogenated return odor is reduced by atomizing. The flavor-added hydrogenated edible oil of the present invention, which has reduced odor from hydrogenation, is useful as a raw material for fat and oil foods, confectionery, frying oil and the like.
【0002】[0002]
【従来の技術】食品精製加工油脂は、油脂食品を製造す
る上で重要な役割を果たしており、その中でも硬化油は
分別油と共に有用であって、マーガリンやショートニン
グなどの油脂食品を製造する際に欠くことができない原
料素材である。この食用硬化油は、液状油脂を水素添加
(以下、水添と略記する)して油脂を構成する脂肪酸の
炭素−炭素二重結合を水素化することにより得られる。
一般的な水添は、反応温度120〜200℃、水素雰囲
気下及び触媒存在下で、液状油脂を撹拌して行われる。
水素圧力は、常圧から5kg/cm2 程度であり、触媒
として、還元ニッケル、ギ酸ニッケル、ラネーニッケ
ル、ホウ化ニッケルなどのニッケル触媒が用いられる。
このようにして得られる食用硬化油は、融点が上昇する
ので、可塑性油脂として用いることができる。また、油
脂を構成する脂肪酸の炭素−炭素二重結合(不飽和結
合)が減少するので、油脂の酸化安定性が向上する。さ
らには、選択的水添により固体脂含量(SFC)の対温
度曲線がシャープな縦型になるので、他の油脂との混合
や分別により、チョコレート、マーガリン、ショートニ
ングなどの食品への適性が良好な油脂となるなどの特性
を示す。BACKGROUND OF THE INVENTION Food refined processed fats and oils play an important role in producing fat and oil foods. Among them, hydrogenated oils are useful together with fractionated oils, and when producing fat and oil foods such as margarine and shortening. It is an indispensable raw material. This hardened edible oil is obtained by hydrogenating a liquid oil (hereinafter abbreviated as hydrogenation) to hydrogenate the carbon-carbon double bond of the fatty acid that constitutes the oil.
General hydrogenation is performed by stirring liquid oil and fat at a reaction temperature of 120 to 200 ° C. under a hydrogen atmosphere and in the presence of a catalyst.
The hydrogen pressure is from normal pressure to about 5 kg / cm 2 , and a nickel catalyst such as reduced nickel, nickel formate, Raney nickel, nickel boride is used as a catalyst.
The hardened edible oil thus obtained has a higher melting point and can be used as a plastic fat. Moreover, since the carbon-carbon double bond (unsaturated bond) of the fatty acid that constitutes the oil and fat is reduced, the oxidative stability of the oil and fat is improved. Furthermore, the selective hydrogenation makes the solid fat content (SFC) temperature curve sharp and vertical, so it is suitable for foods such as chocolate, margarine and shortening by mixing with other fats and oils. It has characteristics such as becoming a fat and oil.
【0003】ところが、食用硬化油を食品素材として用
いる場合、硬化油に特有の水添戻り臭が風味の上で問題
となっている。この水添戻り臭の構成する代表的な成分
としては、不飽和脂肪酸の分解により生成するC9(炭
素数9)−アルデヒドやケトンだとされている(“Hy
drogenation of Fats andOi
ls”,H.B.W.Patterson,p.28
4,AppliedScience Publishe
rs,London,1983)。また、トランス二重
結合を持つオクタヂエナールが、水添戻り臭の重要な成
分であるという報告もなされている(Yasuda e
t.al.,The Journalof Ameri
can Oil Chemists’Society,
Vol.52,p.307,1975)。そして、これ
らの臭気物質として知られているアルデヒドやケトン
は、水添により生成するトランス酸からも比較的簡単に
生成するといわれている(J.G.Keppler e
t.al.,TheJournal of Ameri
can Oil Chemists’Society,
Vol.42,p.246,1965)。However, when hydrogenated edible oil is used as a food material, the hydrogenated odor peculiar to hydrogenated oil causes a problem in flavor. It is said that C9 (C9) -aldehydes and ketones produced by the decomposition of unsaturated fatty acids are typical components constituting the hydrogenated return odor (“Hy”).
diffusion of Fats and Oi
Is ”, H. B. W. Patterson, p. 28.
4, Applied Science Publicize
rs, London, 1983). It has also been reported that octadienal having a trans double bond is an important component of hydrogenated return odor (Yasuda e).
t. al. , The Journal of Ameri
can Oil Chemist's Society,
Vol. 52, p. 307, 1975). Aldehydes and ketones known as these odorants are said to be relatively easily produced from the trans acid produced by hydrogenation (JG Keppler e).
t. al. , The Journal of Ameri
can Oil Chemist's Society,
Vol. 42, p. 246, 1965).
【0004】食用硬化油の水添戻り臭の発生を防止する
方法として、新鮮なニッケル触媒を用いて比較的低い反
応温度(150℃以下)で水添を行う方法、水添後に空
気との接触を極力避けて乾燥した暗所に10℃以下で保
存する方法、あるいは、残留金属による酸化促進を抑制
するためにクエン酸を添加する方法などが一般的に行わ
れている。しかし、これらの方法では、食用硬化油の水
添戻り臭を大幅に低減するに至っていない。また、食用
硬化油にフレーバーを添加することにより水添戻り臭を
マスキングする方法が提案されているが、添加するフレ
ーバーの選定や添加量の決定が難しく、水添戻り臭が低
減されないばかりでなく、添加したフレーバーとの相互
作用でワックス様の臭気が強調されたり、口中での残存
時間が長い不快臭や不快味を残すなどの問題がある。さ
らには、食品硬化油とゴマなどの呈味性油脂とを混合し
て風味安定性を向上させたり(特開平4−11838号
公報)、甘草抽出物を抗酸化剤として食用硬化油に配合
して水添戻り臭の発生を遅延させる(特開昭63−11
0290号公報)などの方法も提案されているが、呈味
性油脂や抗酸化性物質の風味や呈味が食用硬化油混合油
脂の風味を支配し、この油脂を用いるに好ましい油脂食
品はおのずと限定される現状にある。As a method for preventing the generation of hydrogenation odor of hydrogenated edible oil, a method of hydrogenating at a relatively low reaction temperature (150 ° C. or lower) using a fresh nickel catalyst, and a method of contacting with air after hydrogenation In general, a method of avoiding as much as possible and storing at 10 ° C. or lower in a dry dark place, a method of adding citric acid in order to suppress acceleration of oxidation due to residual metal, and the like are generally performed. However, these methods have not significantly reduced the hydrogenated odor of hydrogenated edible oil. Further, a method of masking the hydrogenated return odor by adding a flavor to the hardened edible oil has been proposed, but it is difficult to select the flavor to be added and the amount to be added, and not only the hydrogenated return odor is not reduced. There is a problem that the wax-like odor is emphasized due to the interaction with the added flavor, and an unpleasant odor or unpleasant taste is left in the mouth for a long time. Furthermore, the hardened food oil is mixed with a flavoring oil such as sesame to improve the flavor stability (Japanese Patent Laid-Open No. 4-118838), or the licorice extract is added to the hardened edible oil as an antioxidant. To delay the generation of hydrogenated return odor (JP-A-63-11).
No. 0290 gazette) has been proposed, but the flavors and tastes of tasty fats and oils and antioxidants dominate the flavor of edible hydrogenated oil-mixed fats, and naturally fats and oils foods that are preferable to use these fats and oils are naturally. The situation is limited.
【0005】[0005]
【発明が解決しようとする課題】本発明者らは、上述の
このような問題を鑑み、水添戻り臭を低減した食用硬化
油について鋭意検討を行ったところ、溶解した食用硬化
油にフレーバーを添加した後、噴霧冷却して微粒化する
ことにより、水添戻り臭を低減することができることを
見出し、本発明を成すに至った。したがって、本発明
は、微粒化することによって水添戻り臭を低減したフレ
ーバー添加食用硬化油を提供することを課題とする。ま
た、本発明は、フレーバーを添加した食用硬化油を噴霧
冷却して微粒化する水添戻り臭を低減したフレーバー添
加食用硬化油の製造法を提供することを課題とする。In view of the above-mentioned problems, the present inventors have made earnest studies on a hardened edible oil having a reduced hydrogenation return odor. It was found that the hydrogenated odor can be reduced by spray cooling and atomizing after addition, and the present invention has been completed. Therefore, it is an object of the present invention to provide a flavor-added edible hardened oil in which hydrogenated return odor is reduced by atomizing. Another object of the present invention is to provide a method for producing a flavor-added hardened edible oil that reduces the hydrogenation-reducing odor of atomizing the hardened edible hardened oil by spray cooling.
【0006】[0006]
【課題を解決するための手段】本発明では、食用硬化油
を融点以上の温度に保持して溶解させた後、フレーバー
を添加し、このフレーバー添加食用硬化油をスプレーノ
ズルで微粒状に噴霧して冷風に接触させることにより、
食用硬化油の水添戻り臭を低減する。そして、このよう
にして得られる水添戻り臭を低減したフレーバー添加食
用硬化油は、官能的に悪影響を及ぼす水添戻り臭が極め
て少なく、官能的に優れた風味の良好な食用硬化油とな
る。また、本発明の水添戻り臭を低減したフレーバー添
加食用硬化油と抗酸化剤を併用したり、あるいは他の精
製食用油脂と配合したりすることにより、さらに水添戻
り臭を低減する効果を増強せしめることが可能となり、
風味が良好で安定な食用油脂としてさらに有用なものと
なる。In the present invention, a hardened edible oil is held at a temperature equal to or higher than the melting point and dissolved, and then a flavor is added, and the flavored edible hardened oil is sprayed into fine particles with a spray nozzle. By contacting it with cold air,
Reduces the hydrogenation odor of hydrogenated edible oil. The flavor-added hydrogenated edible oil with reduced hydrogenation return odor thus obtained has very little hydrogenation-returned odor that has a sensory adverse effect, and becomes a edible hydrogenated oil with a sensory excellent flavor. . Further, by using a flavor-added hydrogenated hardened oil having reduced hydrogenated odor of the present invention in combination with an antioxidant, or by blending with other refined edible oils and fats, it is possible to further reduce the hydrogenated odor. It is possible to increase,
It becomes more useful as a stable edible oil and fat having a good flavor.
【0007】本発明で用いる水添された食用硬化油は、
通常、植物油脂もしくは動物油脂を水添して得られる。
その原料となる植物油脂としては、大豆油、カノーラ油
(菜種油)、コーン油、パーム油、あまに油、オリブ
油、ゴマ油、ひまわり油、綿実油などやこれらの分別油
脂を挙げることができる。また、動物油脂としては、魚
油、タロー脂(牛脂)、ラード(豚脂)などやこれらの
分別油脂を挙げることができるが、これらに限定される
ものではない。さらに、本発明では、これらの植物油脂
もしくは動物油脂の微水添油、軽度水添油、中程度水添
油、高度水添油、極度水添油のいずれの食用硬化油も対
象となる。なお、微水添油では水添戻り臭が微弱であっ
て、本発明の効果が顕著に現れないが、ヨウ素価の減少
率として表される水添度が10%以上の油脂では、本発
明の効果が顕著である。The hydrogenated edible hydrogenated oil used in the present invention is
Usually, it is obtained by hydrogenating vegetable oil or animal oil.
Examples of the vegetable oils and fats as the raw material thereof include soybean oil, canola oil (rapeseed oil), corn oil, palm oil, linseed oil, olive oil, sesame oil, sunflower oil, cottonseed oil and the like, and fractionated oils and fats thereof. Examples of animal fats and oils include, but are not limited to, fish oil, tallow fat (beef fat), lard (pork fat), and the like, and fats and oils fractionated from these. Further, in the present invention, edible hydrogenated oils of any of these vegetable oils or animal oils, such as slightly hydrogenated oils, lightly hydrogenated oils, moderately hydrogenated oils, highly hydrogenated oils, and extremely hydrogenated oils are applicable. It should be noted that the slightly hydrogenated oil has a weak hydrogenation return odor, and the effect of the present invention does not appear remarkably. However, when the degree of hydrogenation expressed as a reduction rate of iodine value is 10% or more, The effect of is remarkable.
【0008】本発明では、食用硬化油を溶解する場合、
用いる食用硬化油の融点以上の温度に保持すればよい
が、その融点より10乃至30℃高い温度に保持するこ
とが好ましい。融点乃至融点より10℃未満の高い温度
では、溶解するのに時間がかかり、また、融点より30
℃を越える高い温度では、食用硬化油の酸化劣化が進行
したり、水添戻り臭が増加したりするので好ましくな
い。なお、油脂の溶解に際しては、食用硬化油を粉砕し
たものやフレーク状のものを用いたり、さらには、撹拌
することにより溶解時間を短縮させることが可能であ
り、食用硬化油の酸化劣化を抑制し得るという点で効果
的である。In the present invention, when dissolving hardened edible oil,
It may be maintained at a temperature equal to or higher than the melting point of the hardened edible oil used, but it is preferably maintained at a temperature 10 to 30 ° C. higher than the melting point. At a melting point or a temperature higher than 10 ° C. higher than the melting point, it takes time to dissolve, and the melting point is higher than 30 ° C.
At a high temperature exceeding 0 ° C, oxidative deterioration of the hardened edible oil progresses and the odor returned by hydrogenation increases, which is not preferable. In addition, when dissolving fats and oils, it is possible to shorten the dissolution time by using crushed edible oil or flake-like ones, and further by stirring, and suppress oxidative deterioration of hardened edible oil. It is effective in that it can be done.
【0009】このようにして溶解した食用硬化油にフレ
ーバーを添加する。本発明では、フレーバーとして、油
溶性のフレーバーもしくはフレーバー油を一種もしくは
二種以上組み合わせて用いる。これらのフレーバーとし
て、例えば、バニラフレーバー、クリームフレーバー、
オレンジ、グレープ、グレープフルーツ、レモン、ライ
ム、ストロベリーなどの果実フレーバー、ペパーミント
油、スペアミント油、ペパー油、チョコレートフレーバ
ー、ココアフレーバーなどを挙げることができるが、こ
れらに限定されるものではない。なお、フレーバーは、
目的に応じて対象油脂食品に適するものを選択する。A flavor is added to the hardened edible oil thus dissolved. In the present invention, one or a combination of two or more oil-soluble flavors or flavor oils is used as the flavor. As these flavors, for example, vanilla flavor, cream flavor,
Examples include, but are not limited to, fruit flavors such as orange, grape, grapefruit, lemon, lime and strawberry, peppermint oil, spearmint oil, pepper oil, chocolate flavor, cocoa flavor and the like. The flavor is
Select the one suitable for the target oil and fat food according to the purpose.
【0010】次に、フレーバーを添加した食用硬化油を
圧力ノズルや二流体ノズルなどのアトマイザーを用いて
微粒化し、噴霧冷却する。この噴霧冷却に用いる装置
は、食用硬化油を噴霧するための加熱可能なノズル、噴
霧により微粒化された食用硬化油を流動させるチャンバ
ー、それに続くサイクロン及びバッグフィルターからな
る。なお、噴霧ノズルとして、二流体ノズル形式のアト
マイザーを用いることにより、微細な食用硬化油の液滴
を生成させることができ、食用硬化油単位重量当たりの
冷却風との接触面積を増大させることができるので、水
添戻り臭を低減するという本発明の目的を達成する上
で、二流体ノズルを用いることが好ましい。また、二流
体ノズルを用いる場合、食用硬化油を微粒化するための
加圧気体として、通常、空気を用いるが、本発明では窒
素ガスなどを用いることもできる。これらの加圧気体
は、噴霧する食用硬化油の融点よりも僅かに高い温度に
調整して用いることが好ましい。また、加圧気体の圧力
は、食用硬化油の微粒化を制御する上で非常に重要であ
り、加圧気体の圧力を高めることで食用硬化油液滴の粒
径を小さくすることができる。Next, the flavored edible hardened oil is atomized using an atomizer such as a pressure nozzle or a two-fluid nozzle and spray-cooled. The apparatus used for spray cooling comprises a heatable nozzle for spraying hardened edible oil, a chamber for flowing hardened edible oil that has been atomized by spraying, followed by a cyclone and a bag filter. By using a two-fluid nozzle type atomizer as the spray nozzle, it is possible to generate fine droplets of hardened edible oil and increase the contact area with the cooling air per unit weight of hardened edible oil. Therefore, it is preferable to use the two-fluid nozzle in order to achieve the object of the present invention to reduce the odor returned by hydrogenation. Further, when the two-fluid nozzle is used, air is usually used as the pressurized gas for atomizing the hardened edible oil, but nitrogen gas or the like can be used in the present invention. These pressurized gases are preferably adjusted to a temperature slightly higher than the melting point of the hardened edible oil to be sprayed before use. Further, the pressure of the pressurized gas is very important for controlling the atomization of the hardened edible oil, and increasing the pressure of the pressurized gas can reduce the particle size of the hardened edible oil droplets.
【0011】噴霧により微細な液滴となった食用硬化油
は、チャンバー内を流れる冷却風により冷却される。冷
却風の流れは、食用硬化油の噴霧方向に対して対流であ
っても構わないし、また、向流であっても構わない。冷
却風の温度は、食用硬化油の融点よりも低くなければな
らないが、融点よりも10℃以上低い温度が特に好まし
い。冷却風の温度と流量は、食用硬化油の水添戻り臭を
低減する上で非常に重要である。冷却風の温度が高けれ
ば高い程、あるいは、冷却風の流量が大きければ大きい
程、食用硬化油の水添戻り臭は低減されるが、チャンバ
ー内での食用硬化油の付着量が増加し、したがって、食
用硬化油の回収量が低減する。なお、大容量のチャンバ
ーを用いることにより、この弊害をある程度避けること
が可能である。このチャンバー内での冷却過程で、食用
硬化油は多量の冷却風に曝され、食用硬化油の水添戻り
臭は、添加したフレーバーの一部を伴って食用硬化油の
液滴表面から除去され、食用硬化油の水添戻り臭は低減
される。The hardened edible oil, which has been formed into fine droplets by spraying, is cooled by cooling air flowing in the chamber. The flow of the cooling air may be convection or countercurrent with respect to the spray direction of the hardened edible oil. The temperature of the cooling air must be lower than the melting point of the hardened edible oil, but a temperature of 10 ° C. or more lower than the melting point is particularly preferable. The temperature and flow rate of the cooling air are very important in reducing the hydrogenated odor of hydrogenated edible oil. The higher the temperature of the cooling air, or the larger the flow rate of the cooling air, the more the hydrogenation odor of hydrogenated edible oil is reduced, but the amount of hardened edible oil adhered in the chamber increases, Therefore, the amount of hardened edible oil recovered is reduced. By using a large-capacity chamber, this adverse effect can be avoided to some extent. During the cooling process in this chamber, the hardened edible oil is exposed to a large amount of cooling air, and the hydrogenated odor of the hardened edible oil is removed from the surface of the liquid droplets of the hardened edible oil along with some of the added flavors. The hydrogenated odor of hydrogenated edible oil is reduced.
【0012】このように噴霧冷却処理を付した食用硬化
油は、微粒化された粉末状となる。そして、この食用硬
化油の微粒化粉末をチャンバーに続くサイクロン及びバ
ッグフィルターにより回収する。このようにして得られ
た食用硬化油は、水添戻り臭が著しく低減されており、
かつ添加したフレーバーが残存しているので、水添戻り
臭による官能的な阻害が無く風味の良好なものとなる。
この水添戻り臭を低減したフレーバー添加食用硬化油
は、微粒化粉末の状態でそのまま用いることができる
し、加熱溶解して液状で用いることもできる。次に本発
明の実施例を挙げて具体的に説明する。The hardened edible oil thus spray-cooled is in the form of finely divided powder. Then, this atomized powder of hardened edible oil is collected by a cyclone and a bag filter following the chamber. The edible hydrogenated oil thus obtained has a significantly reduced hydrogenation return odor,
Moreover, since the added flavor remains, there is no sensory inhibition due to the hydrogenated return odor and the flavor is good.
This flavor-added hardened oil with reduced hydrogenated odor can be used as it is in the form of atomized powder, or it can be heated and dissolved to be used in liquid form. Next, an example of the present invention will be specifically described.
【0013】[0013]
【実施例1】常法により、精製大豆白絞油を完全に水添
して得られた市販の大豆極度硬化油(ヨウ素価0.2、
融点67℃、ステアリン酸88%、パルミチン酸11
%、ベヘン酸1%)を原料として、水添戻り臭を低減し
たフレーバー添加食用硬化油を製造した。大豆極度硬化
油を85℃に保持し、緩やかに撹拌して溶解した後、市
販のバニラフレーバーを油脂重量に対して0.5%添加
した。次に、この硬化油を1,800ml/分の流量で
二流体ノズルの内管から、また、90℃に加熱した加圧
空気(5.5kg/cm2 )を5,400ml/分の流
量で二流体ノズルの外管から、それぞれジェット流とし
てチャンバー内に噴霧した。チャンバー内では、20℃
に冷却した空気を二流体ノズルの方向に向流に8,00
0ml/分の流量でチャンバー内に流入して流動させ
た。二流体ノズルにより微細な液滴になった硬化油は、
冷却風に曝されて冷却固化した。この微粒化大豆極度硬
化油を10℃に冷却した空気でサイクロンに搬送し、回
収した。このようにして得られた大豆極度硬化油粉末の
平均粒径は15μmであり、水添戻り臭のないバニラ風
味の食用硬化油が得られた。Example 1 A commercially available soybean extremely hardened oil (iodine value 0.2, obtained by completely hydrogenating refined soybean white squeezing oil by a conventional method)
Melting point 67 ° C, stearic acid 88%, palmitic acid 11
%, Behenic acid 1%) was used as a raw material to produce flavored edible hardened oil with reduced hydrogenated odor. The soybean extremely hardened oil was kept at 85 ° C., gently stirred and dissolved, and then a commercially available vanilla flavor was added at 0.5% based on the weight of the fat and oil. Next, this hardened oil was supplied from the inner tube of the two-fluid nozzle at a flow rate of 1,800 ml / min, and pressurized air (5.5 kg / cm 2 ) heated to 90 ° C. was supplied at a flow rate of 5,400 ml / min. From the outer tube of the two-fluid nozzle, they were sprayed into the chamber as jet streams. 20 ° C in the chamber
The cooled air is countercurrent to the two-fluid nozzle by 8,000
It was flowed into the chamber at a flow rate of 0 ml / min. Hardened oil that has become fine droplets by the two-fluid nozzle,
It was exposed to cooling air and solidified by cooling. This atomized soybean extremely hardened oil was conveyed to a cyclone with air cooled to 10 ° C. and collected. The soybean extremely hardened oil powder thus obtained had an average particle size of 15 μm, and a vanilla-flavored edible hardened oil having no hydrogenated reversion odor was obtained.
【0014】[0014]
【実施例2】常法により、精製コーン油を中程度に水添
して得られた市販のコーン硬化油(ヨウ素価66.5、
融点38℃、ステアリン酸12%、オレイン酸77%、
パルミチン酸11%)を原料として、水添戻り臭を低減
したフレーバー添加食用硬化油を製造した。コーン硬化
油を60℃に保持し、緩やかに撹拌して溶解した後、市
販のオレンジ油を油脂重量に対して0.3%添加した。
次に、この硬化油を1,800ml/分の流量で二流体
ノズルの内管から、また、70℃に加熱した加圧空気
(5.5kg/cm2 )を5,400ml/分の流量で
二流体ノズルの外管から、それぞれジェット流としてチ
ャンバー内に噴霧した。チャンバー内では、5℃に冷却
した空気を二流体ノズルの方向に向流に8,000ml
/分の流量でチャンバー内に流入して流動させた。二流
体ノズルにより微細な液滴になった硬化油は、冷却風に
曝されて冷却固化した。この微粒化コーン硬化油を5℃
に冷却した空気でサイクロンに搬送し、回収した。この
ようにして得られたコーン硬化油粉末の平均粒径は23
μmであり、水添戻り臭のないオレンジ風味の食用硬化
油脂が得られた。Example 2 A commercially available corn hydrogenated oil (iodine number: 66.5, obtained by hydrogenating a refined corn oil to an intermediate degree by a conventional method).
Melting point 38 ° C, stearic acid 12%, oleic acid 77%,
Palmitic acid (11%) was used as a raw material to produce a flavor-added edible hydrogenated oil with reduced hydrogenated odor. The hardened corn oil was kept at 60 ° C., and was gently stirred to dissolve it. Then, 0.3% of a commercially available orange oil was added to the weight of the fat and oil.
Next, this hardened oil was supplied from the inner tube of the two-fluid nozzle at a flow rate of 1,800 ml / min, and pressurized air (5.5 kg / cm 2 ) heated to 70 ° C. was supplied at a flow rate of 5,400 ml / min. From the outer tube of the two-fluid nozzle, they were sprayed into the chamber as jet streams. In the chamber, the air cooled to 5 ° C was counter-currently directed toward the two-fluid nozzle to 8,000 ml.
Flowed into the chamber at a flow rate of / min. The hardened oil formed into fine droplets by the two-fluid nozzle was exposed to cooling air and solidified by cooling. This atomized corn hydrogenated oil is 5 ℃
It was transported to a cyclone with air cooled to and collected. The corn hydrogenated oil powder thus obtained has an average particle size of 23.
An edible hydrogenated edible oil / fat having a thickness of μm and no odor of hydrogenation was obtained.
【0015】[0015]
【試験例1】訓練を受けた専門パネラー10人により、
70℃に保持して液状とした以下の油脂群について、官
能評価を実施した。 油脂群1:大豆硬化油 油脂群2:バニラフレーバーを0.5%添加した大豆硬
化油 油脂群3:噴霧冷却処理して微粒化した大豆硬化油 油脂群4:バニラフレーバーを0.5%添加し、噴霧冷
却処理して微粒化した大豆硬化油[Test Example 1] By 10 trained professional panelists,
Sensory evaluation was performed on the following oils and fats that were kept liquid at 70 ° C. Fats and oils group 1: Hardened soybean oils Fats and oils group 2: Hardened soybean oils containing 0.5% vanilla flavor Oils and fats group 3: Hardened soybean oils atomized by spray cooling treatment Fats and oils group 4: 0.5% vanilla flavors added Soybean hydrogenated oil that has been atomized by spray cooling treatment
【0016】官能評価は、フレーバー臭の強度、水添戻
り臭の強度及び好ましさについて、表1に示す基準によ
って行った。The sensory evaluation was carried out according to the criteria shown in Table 1 for the intensity of flavor odor, the intensity of hydrogenated return odor and the preference.
【表1】 ──────────────────────────────────── 評価点 フレーバー臭の強度 水添戻り臭の強度 好ましさ ──────────────────────────────────── 1 2 弱い 弱い 悪い 3 4 やや弱い やや弱い やや悪い 5 6 普通 普通 どちらでもない 7 8 やや強い やや強い 良好 9 10 強い 強い 極めて良好 ────────────────────────────────────[Table 1] ──────────────────────────────────── Evaluation score Flavor odor intensity Hydrogenated return odor Strength of ──────────────────────────────────── 1 2 Weak Weak Poor 3 4 Weak Moderately weak Moderate 5 6 Normal Moderate Neither 7 8 Moderately strong Good 9 10 Strong strong Very good ─────────────────────────── ──────────
【0017】そして、パネラー全員の評価点の平均値を
官能評価点とした。その結果を表2に示す。The average value of the evaluation scores of all the panelists was used as the sensory evaluation score. The results are shown in Table 2.
【表2】 ──────────────────────────────────── フレーバー臭の強度 水添戻り臭の強度 好ましさ ──────────────────────────────────── 油脂群1 0.3 7.2 3.2 油脂群2 7.3 6.1 4.0 油脂群3 0.3 5.6 5.3 油脂群4 5.5 3.3 7.2 ──────────────────────────────────── バニラフレーバーを添加し、噴霧冷却処理して微粒化し
た大豆硬化油は、他の油脂群と比較して、水添戻り臭の
強度が弱く、好ましさの評価が高かった。[Table 2] ──────────────────────────────────── Strength of flavor odor Strength of hydrogenated odor Preferability ──────────────────────────────────── Fat and oil group 1 0.3 7.2 3. 2 Oil / fat group 2 7.3 6.1 4.0 Oil / fat group 3 0.3 5.6 5.3 Oil / fat group 4 5.5 3.3 3.3 7.2 ────────────── ─────────────────────── The soybean hydrogenated oil that was added with vanilla flavor and atomized by spray cooling was compared with other fats and oils. However, the strength of the hydrogenated return odor was weak, and the favorable evaluation was high.
【0018】[0018]
【試験例2】以下の油脂群について、試験例1と同様に
官能評価を実施した。 油脂群1:コーン硬化油 油脂群2:オレンジフレーバーを0.5%添加したコー
ン硬化油 油脂群3:噴霧冷却処理して微粒化したコーン硬化油 油脂群4:オレンジフレーバーを0.5%添加し、噴霧
冷却処理して微粒化したコーン硬化油[Test Example 2] Sensory evaluations were performed on the following groups of fats and oils in the same manner as in Test Example 1. Fats and oils group 1: Hardened corn oils Fats group 2: Hardened corn oils with 0.5% orange flavor Oils and fats group 3: Hardened corn oil spray-cooled corn fats and oils group 4: Add 0.5% orange flavors Corn hardened oil that has been atomized by spray cooling treatment
【0019】その結果を表3に示す。The results are shown in Table 3.
【表3】 ──────────────────────────────────── フレーバー臭の強度 水添戻り臭の強度 好ましさ ──────────────────────────────────── 油脂群1 0.2 5.2 4.2 油脂群2 7.5 4.7 5.5 油脂群3 0.2 3.5 6.8 油脂群4 5.1 3.0 7.3 ──────────────────────────────────── オレンジフレーバーを添加し、噴霧冷却処理して微粒化
したコーン硬化油は、他の油脂群と比較して、水添戻り
臭の強度が弱く、好ましさの評価が高かった。[Table 3] ──────────────────────────────────── Flavor odor intensity Hydrogenated return odor intensity Preferability ──────────────────────────────────── Fat and oil group 1 0.2 5.2 5.2. 2 Oil / fat group 2 7.5 4.7 4.7 5.5 Oil / fat group 3 0.2 3.5 6.8 Oil / fat group 4 5.1 3.0 3.0 7.3 ────────────── ─────────────────────── Cone hydrogenated oil that has been refined by spray cooling and atomized is compared to other fats and oils. However, the strength of the hydrogenated return odor was weak, and the favorable evaluation was high.
【0020】[0020]
【発明の効果】本発明では、フレーバーを添加し、噴霧
冷却して微粒化することにより、水添戻り臭を低減した
フレーバー添加食用硬化油を提供することを可能とし
た。この水添戻り臭を低減したフレーバー添加食用硬化
油は、官能的に悪影響を及ぼす水添戻り臭が極めて少な
く、官能的に優れた風味の油脂であり、油脂食品、菓
子、揚げ油などの原料として有用である。INDUSTRIAL APPLICABILITY In the present invention, it is possible to provide a flavor-added edible hardened oil in which the flavor returned from hydrogenation is reduced by adding a flavor, spray cooling and atomizing. This flavored edible hardened oil with reduced hydrogenation odor has very little hydrogenation odor that has a sensory adverse effect, and is a fat and oil with a sensory excellent flavor, and is used as a raw material for fat foods, confectionery, frying oil, etc. It is useful.
Claims (2)
とを特徴とする水添戻り臭を低減したフレーバー添加食
用硬化油。1. A flavored edible hardened oil having a reduced hydrogenation-reducing odor, characterized by having a particle size of 100 μm or less.
した後、噴霧冷却して粒子径を100μm以下に微粒化
することを特徴とする水添戻り臭を低減したフレーバー
添加食用硬化油の製造法。2. A process for producing a flavored hardened edible oil with reduced hydrogenated odor, which comprises adding a flavor to a dissolved hardened edible oil and then spray cooling to atomize the particle size to 100 μm or less. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5140136A JPH06327403A (en) | 1993-05-19 | 1993-05-19 | Flavor-added hardened food oil with reduced hydrogenation back small and production process thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5140136A JPH06327403A (en) | 1993-05-19 | 1993-05-19 | Flavor-added hardened food oil with reduced hydrogenation back small and production process thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06327403A true JPH06327403A (en) | 1994-11-29 |
Family
ID=15261723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5140136A Pending JPH06327403A (en) | 1993-05-19 | 1993-05-19 | Flavor-added hardened food oil with reduced hydrogenation back small and production process thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06327403A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1726215A1 (en) | 2005-05-09 | 2006-11-29 | Compagnie Gervais-Danone | Method for the manufacturing of soy and milk protein-based preparations having a high total protein content |
| JPWO2008032852A1 (en) * | 2006-09-14 | 2010-01-28 | 長谷川香料株式会社 | Hardened oil flavoring agent |
| JP2018115282A (en) * | 2017-01-20 | 2018-07-26 | 日清オイリオグループ株式会社 | Flavor enhancer of citrus flavor and improved flavor |
| JP2019187383A (en) * | 2018-04-27 | 2019-10-31 | 日清オイリオグループ株式会社 | Powder oil and fat composition for topping |
-
1993
- 1993-05-19 JP JP5140136A patent/JPH06327403A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1726215A1 (en) | 2005-05-09 | 2006-11-29 | Compagnie Gervais-Danone | Method for the manufacturing of soy and milk protein-based preparations having a high total protein content |
| JPWO2008032852A1 (en) * | 2006-09-14 | 2010-01-28 | 長谷川香料株式会社 | Hardened oil flavoring agent |
| JP5249767B2 (en) * | 2006-09-14 | 2013-07-31 | 長谷川香料株式会社 | Hardened oil flavoring agent |
| JP2018115282A (en) * | 2017-01-20 | 2018-07-26 | 日清オイリオグループ株式会社 | Flavor enhancer of citrus flavor and improved flavor |
| JP2019187383A (en) * | 2018-04-27 | 2019-10-31 | 日清オイリオグループ株式会社 | Powder oil and fat composition for topping |
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