JP6714001B2 - Method for producing soybean oil, method for producing mixed oil, and method for suppressing bright odor of soybean oil - Google Patents
Method for producing soybean oil, method for producing mixed oil, and method for suppressing bright odor of soybean oil Download PDFInfo
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- 239000003921 oil Substances 0.000 title claims description 180
- 235000019198 oils Nutrition 0.000 title claims description 174
- 239000003549 soybean oil Substances 0.000 title claims description 71
- 235000012424 soybean oil Nutrition 0.000 title claims description 71
- 238000004519 manufacturing process Methods 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 21
- 239000003925 fat Substances 0.000 claims description 80
- 235000010469 Glycine max Nutrition 0.000 claims description 64
- 244000068988 Glycine max Species 0.000 claims description 64
- 102000003820 Lipoxygenases Human genes 0.000 claims description 32
- 108090000128 Lipoxygenases Proteins 0.000 claims description 32
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 13
- 230000001877 deodorizing effect Effects 0.000 claims description 10
- 230000001678 irradiating effect Effects 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 239000010461 other edible oil Substances 0.000 claims description 6
- 235000019486 Sunflower oil Nutrition 0.000 claims description 5
- 239000008157 edible vegetable oil Substances 0.000 claims description 5
- 239000002600 sunflower oil Substances 0.000 claims description 5
- 235000019482 Palm oil Nutrition 0.000 claims description 3
- 235000005687 corn oil Nutrition 0.000 claims description 3
- 239000002285 corn oil Substances 0.000 claims description 3
- 235000014593 oils and fats Nutrition 0.000 claims description 3
- 239000002540 palm oil Substances 0.000 claims description 3
- GGNZKBPHAMNUOU-UHFFFAOYSA-N 9-(3,4-dimethyl-5-pentylfuran-2-yl)-nonanoic acid Chemical compound CCCCCC=1OC(CCCCCCCCC(O)=O)=C(C)C=1C GGNZKBPHAMNUOU-UHFFFAOYSA-N 0.000 claims 4
- 238000012360 testing method Methods 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000004042 decolorization Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000004332 deodorization Methods 0.000 description 6
- 238000007670 refining Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000011088 calibration curve Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 235000010746 mayonnaise Nutrition 0.000 description 4
- 239000008268 mayonnaise Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- QSQLTHHMFHEFIY-FNTGBJKTSA-N [2H]C(CCCCCCCCCCCCCCCCCCC)C([2H])([2H])C(=O)OC Chemical compound [2H]C(CCCCCCCCCCCCCCCCCCC)C([2H])([2H])C(=O)OC QSQLTHHMFHEFIY-FNTGBJKTSA-N 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 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
- 230000000887 hydrating effect Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000003904 phospholipids Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Description
本発明は、大豆油の製造方法に関し、詳しくは明所臭の低減された大豆油の製造方法、その大豆油を配合した混合油の製造方法、ならびに大豆油の明所臭を抑制する方法に関する。 The present invention relates to a method for producing soybean oil, and more particularly to a method for producing soybean oil having a reduced clear-smell odor, a method for producing a mixed oil containing the soybean oil, and a method for suppressing clear-smell odor of soybean oil. ..
大豆油は、精製工程を経て無臭となるにもかかわらず、保存中に戻り臭と呼ばれる特有の臭いが発生する。この戻り臭は、保存時の光が最大の発生要因であると言われており、「明所臭」とも呼ばれている。従来、この明所臭がサラダ油やマヨネーズなどへの大豆油の配合量を制限していた。 Although soybean oil becomes odorless after undergoing a refining process, a unique odor called a returning odor is generated during storage. This return odor is said to be caused most by light during storage, and is also called a "bright place odor". Conventionally, this bright-smelling odor has limited the amount of soybean oil blended in salad oil, mayonnaise, and the like.
大豆油の製造方法に関しては、例えば特許文献１には、有機溶剤を用いることなく大豆種子の圧搾処理を施す工程を有し、前記処理前の工程を９０℃以下の温度でおこなうことを特徴とする製造方法が開示されている。そしてその実施例には、当該製造方法で得られた大豆油は曝光後の風味が比較例に比して良好であることが記載されている。 Regarding the method for producing soybean oil, for example, Patent Document 1 has a step of subjecting soybean seeds to compression treatment without using an organic solvent, and the step before the treatment is performed at a temperature of 90° C. or lower. A method of manufacturing is disclosed. Then, it is described in the examples that the soybean oil obtained by the production method has a better flavor after exposure to light than the comparative examples.
しかしながら、上記特許文献1に記載の方法では、大豆種子からの搾油率が低く、明所臭の低減効果も充分ではなかった。 However, with the method described in Patent Document 1, the oil extraction rate from soybean seeds was low, and the effect of reducing bright odor was not sufficient.
本発明の目的は、明所臭の低減された大豆油の製造方法、その大豆油を配合した混合油の製造方法、ならびに大豆油の明所臭を抑制する方法を提供することにある。 An object of the present invention is to provide a method for producing soybean oil having a reduced clear odor, a method for producing a mixed oil containing the soybean oil, and a method for suppressing the clear odor of soybean oil.
本発明者らは、上記課題を解決するために鋭意検討した結果、大豆から搾油された油脂に、その油脂中の３，４−ジメチル−５−ペンチル−２−フランノナン酸（以下、「Ｆ３」と略す。）量を低減させるように、特定波長の紫外線を照射することにより、または、リポキシゲナーゼを接触させることにより、大豆油の明所臭を低減できることを見出し、本発明を完成した。 MEANS TO SOLVE THE PROBLEM As a result of earnestly studying in order to solve the said subject, the present inventors have found that the oil and fat extracted from soybeans contained 3,4-dimethyl-5-pentyl-2-furanononanoic acid (hereinafter, "F3"). It was found that the bright odor of soybean oil can be reduced by irradiating it with ultraviolet rays having a specific wavelength or by bringing it into contact with lipoxygenase so as to reduce the amount thereof.
すなわち、本発明の第１の態様は、大豆から搾油された油脂に、その油脂中のＦ３量を低減させるように、波長２００〜２８０ｎｍの紫外線を照射する工程を含む、大豆油の製造方法を提供するものである。 That is, the first aspect of the present invention is a method for producing soybean oil, which comprises a step of irradiating oil and fat extracted from soybeans with ultraviolet rays having a wavelength of 200 to 280 nm so as to reduce the amount of F3 in the oil and fat. Is provided.
本発明の第１の態様の大豆油の製造方法においては、前記工程で得られた油脂を脱臭処理する工程を含むことが好ましい。 The method for producing soybean oil according to the first aspect of the present invention preferably includes a step of deodorizing the oil/fat obtained in the above step.
本発明の第１の態様の大豆油の製造方法においては、大豆から搾油された前記油脂が脱ガム処理を経た油脂であることが好ましい。 In the method for producing soybean oil according to the first aspect of the present invention, it is preferable that the oil or fat extracted from soybeans is an oil or fat that has been degummed.
また、本発明の第２の態様は、大豆から搾油された油脂に、その油脂中のＦ３量を低減させるように、リポキシゲナーゼを接触させる工程を含む、大豆油の製造方法を提供するものである。 A second aspect of the present invention provides a method for producing soybean oil, which comprises a step of contacting oil and fat extracted from soybeans with lipoxygenase so as to reduce the amount of F3 in the oil and fat. ..
本発明の第２の態様の大豆油の製造方法においては、前記リポキシゲナーゼが大豆由来であることが好ましい。 In the method for producing soybean oil according to the second aspect of the present invention, it is preferable that the lipoxygenase is derived from soybean.
本発明の第２の態様の大豆油の製造方法においては、前記工程で得られた油脂を脱臭処理する工程を含むことが好ましい。 The method for producing soybean oil according to the second aspect of the present invention preferably includes a step of deodorizing the oil/fat obtained in the above step.
本発明の第２の態様の大豆油の製造方法においては、大豆から搾油された前記油脂が脱ガム処理を経た油脂であることが好ましい。 In the method for producing soybean oil according to the second aspect of the present invention, it is preferable that the oil or fat extracted from soybeans is an oil or fat that has been degummed.
本発明の第１又は第２の態様の大豆油の製造方法においては、前記紫外線の照射後又は前記リポキシゲナーゼとの接触後の該油脂中の前記Ｆ３量が１８０ｐｐｍ以下であることが好ましい。また、前記Ｆ３量が６０ｐｐｍ以下であることがより好ましい。 In the method for producing soybean oil according to the first or second aspect of the present invention, it is preferable that the amount of F3 in the fat or oil after irradiation with the ultraviolet rays or after contact with the lipoxygenase is 180 ppm or less. Further, the amount of F3 is more preferably 60 ppm or less.
一方、本発明の第３の態様は、大豆から搾油された油脂に、その油脂中のＦ３量を低減させるように、波長２００〜２８０ｎｍの紫外線を照射することにより、又は、リポキシゲナーゼを接触させることにより得られた大豆油を、前記大豆油以外の他の食用油と混合する工程を含む、混合油の製造方法を提供するものである。 On the other hand, a third aspect of the present invention is to irradiate oil and fat extracted from soybeans with ultraviolet rays having a wavelength of 200 to 280 nm or to contact lipoxygenase so as to reduce the amount of F3 in the oil and fat. It is intended to provide a method for producing a mixed oil, which comprises a step of mixing the soybean oil obtained by the above with an edible oil other than the soybean oil.
本発明の第３の態様の混合油の製造方法においては、前記混合油中の前記大豆油の配合割合が、１５質量％以上となるように、前記大豆油を前記他の食用油と混合することが好ましい。 In the method for producing a mixed oil according to the third aspect of the present invention, the soybean oil is mixed with the other edible oil so that the blending ratio of the soybean oil in the mixed oil is 15% by mass or more. It is preferable.
本発明の第３の態様の混合油の製造方法においては、前記他の食用油が、菜種油、ひまわり油、コーン油、パーム油、パーム分別油からなる群から選ばれた１種又は２種以上であることが好ましい。 In the method for producing a mixed oil according to the third aspect of the present invention, the other edible oil is one or more selected from the group consisting of rapeseed oil, sunflower oil, corn oil, palm oil and palm fractionated oil. Is preferred.
本発明の第３の態様の混合油の製造方法においては、下記式（１）で算出される値Ａが４０未満であることが好ましい。 In the method for producing a mixed oil according to the third aspect of the present invention, the value A calculated by the following formula (1) is preferably less than 40.
Ａ＝前記紫外線の照射後又は前記リポキシゲナーゼとの接触後の該油脂中の前記Ｆ３量（ｐｐｍ）×前記混合油中の前記大豆油の配合割合（質量％）÷１００ …（１） A=the amount of F3 (ppm) in the oil/fat after irradiation with the ultraviolet rays or after contact with the lipoxygenase×mixing ratio of the soybean oil in the mixed oil (mass %)÷100 (1)
他方、本発明の第４の態様は、大豆から搾油された油脂に、その油脂中のＦ３量を低減させるように、波長２００〜２８０ｎｍの紫外線を照射するか、又は、リポキシゲナーゼを接触させる、大豆油の明所臭を低減する方法を提供するものである。 On the other hand, the fourth aspect of the present invention, to the oil and fat extracted from soybeans, so as to reduce the amount of F3 in the oil and fat, to irradiate ultraviolet rays having a wavelength of 200 to 280 nm, or to contact with lipoxygenase, large It is intended to provide a method for reducing the bright odor of soybean oil.
本発明によれば、明所臭の低減された大豆油の製造方法、その大豆油を配合した混合油の製造方法、ならびに大豆油の明所臭を抑制する方法を提供するすることができる。 ADVANTAGE OF THE INVENTION According to this invention, the manufacturing method of the soybean oil with which the clear odor was reduced, the manufacturing method of the mixed oil which mixed the soybean oil, and the method of suppressing the clear odor of soybean oil can be provided.
一般的に、食用油は、油糧原料から圧搾抽出および／または溶剤抽出により搾油して原油を得た後、その原油をさらに精製することにより製造されている。 In general, edible oil is produced by squeezing oil raw materials by pressing and/or solvent extraction to obtain crude oil, and then further refining the crude oil.
圧搾抽出とは、原料に高圧を加えて細胞中の油分を搾り取ることにより行うものである。圧搾抽出は、ゴマのような比較的油分の高い植物原料に向いている。 Press extraction is performed by applying high pressure to the raw material and squeezing out the oil content in the cells. Press extraction is suitable for plant materials with a relatively high oil content such as sesame.
溶剤抽出とは、原料となる油糧種子を圧扁もしくは圧搾抽出後の残渣に溶剤を接触させ、油分を溶剤溶液として抽出し、得られる溶液から溶剤を留去して油分を得ることにより行うものである。溶剤抽出は、大豆のような含油量の少ない原料に向いている。溶剤にはヘキサンなどを使用する。 Solvent extraction is performed by contacting a solvent with the residue after pressing or pressing the oil seeds as a raw material, extracting the oil as a solvent solution, and distilling the solvent from the resulting solution to obtain the oil. It is a thing. Solvent extraction is suitable for raw materials with low oil content such as soybeans. Hexane is used as the solvent.
原油を精製する手段としては、植物油の一般的な精製工程が適用されている。すなわち、一般に、（抽出油）原油→脱ガム油→脱酸油→脱色油→脱臭油（精製油）の順に不純物が除かれ、それぞれの間の操作である「脱ガム処理」、「脱酸処理」、「脱色処理」、「脱臭処理」の工程は、それ自体としては一般的な、脱ガム処理、脱酸処理、脱色処理、脱臭処理が採用される。 As a means for refining crude oil, a general refining process for vegetable oil is applied. That is, in general, impurities are removed in the order of (extracted oil) crude oil → degummed oil → deoxidized oil → decolorized oil → deodorized oil (refined oil), and the operations between them are "degumming" and "deoxidized". For the steps of "treatment", "decolorization treatment", and "deodorization treatment", degumming treatment, deoxidation treatment, decolorization treatment, and deodorization treatment which are generally used as such are adopted.
ここで、脱ガム処理は、例えば、油分中に含まれるリン脂質を主成分とするガム質を水和除去する工程である。 Here, the degumming treatment is, for example, a step of hydrating and removing a gum substance whose main component is phospholipid contained in oil.
また、脱酸処理は、例えば、アルカリ水で処理することにより、油分中に含まれる遊離脂肪酸をセッケン分として除去する工程である。 Further, the deoxidation treatment is a step of removing free fatty acids contained in oil as soap components by treating with alkaline water, for example.
また、脱色処理は、例えば、油分中に含まれる色素を活性白土に吸着させて除去する工程である。 The decolorization treatment is, for example, a step of adsorbing and removing the pigment contained in the oil from the activated clay.
また、脱臭処理は、例えば、減圧下で水蒸気蒸留することによって油分中に含まれる揮発性有臭成分を除去する工程である。 In addition, the deodorizing process is a process of removing volatile odorous components contained in the oil by steam distillation under reduced pressure, for example.
本明細書において、「大豆から搾油された油脂」とは、以上に説明したような一般的な食用油の精製工程の途中段階の油脂も含み、また、それらを終えた大豆油をも包含する意味である。 In the present specification, the term “oil and fat extracted from soybean” includes fats and oils in the middle stage of the general edible oil refining process as described above, and also includes soybean oil after finishing them. Is the meaning.
本発明の一態様においては、大豆から搾油された油脂に、その油脂中のＦ３量を低減させるように、波長２００〜２８０ｎｍの紫外線を照射する。なお、Ｆ３（３，４−ジメチル−５−ペンチル−２−フランノナン酸）は、通常、油脂中のグリセロールとエステル結合した状態で存在する。よって、本明細書において、油脂中のＦ３量とは、主にグリセロールとエステル結合した状態のＦ３量を指す。 In one aspect of the present invention, oil and fat extracted from soybeans is irradiated with ultraviolet rays having a wavelength of 200 to 280 nm so as to reduce the amount of F3 in the oil and fat. In addition, F3 (3,4-dimethyl-5-pentyl-2-furanononanoic acid) usually exists in a state of being ester-bonded with glycerol in the fat or oil. Therefore, in the present specification, the amount of F3 in fats and oils mainly refers to the amount of F3 in the state of being ester-bonded with glycerol.
紫外線は波長の長さで３つに分類され、紫外線Ａ波、Ｂ波、Ｃ波に分類される。紫外線Ａ波、Ｂ波、およびＣ波の波長は、それぞれ、３１５〜４００ｎｍ、２８０〜３１５ｎｍ、および２００〜２８０ｎｍである。本発明ではこのうち、紫外線Ｃ波に相当する波長２００〜２８０ｎｍの紫外線を用いる。好ましくは、波長２２０〜２７０ｎｍの紫外線を用いる。後述する比較例で示したように、紫外線Ａ波である波長３６５ｎｍの紫外線や可視光では、Ｆ３量は減少するものの明所臭を低減することはできない。よって、Ｆ３量と明所臭の低減効果が必ずしも相関するものではないが、照射した紫外線が有効に油脂に影響を与えたかどうか、あるいはその影響の程度の指標となる。なお、本発明においては、紫外線Ｃ波に相当する波長２００〜２８０ｎｍの紫外線を、Ｆ３量を低減するのに有効な強度で含む紫外線を用いればよく、上記波長以外の紫外線や可視光線等を含む光源を照射してもよい。 Ultraviolet rays are classified into three types according to wavelength length, and are classified into ultraviolet rays A wave, B wave, and C wave. The wavelengths of the ultraviolet A wave, B wave, and C wave are 315 to 400 nm, 280 to 315 nm, and 200 to 280 nm, respectively. In the present invention, among these, ultraviolet rays having a wavelength of 200 to 280 nm corresponding to ultraviolet C waves are used. Preferably, ultraviolet rays having a wavelength of 220 to 270 nm are used. As shown in a comparative example to be described later, in the case of ultraviolet light having a wavelength of 365 nm, which is an ultraviolet A wave, or visible light, the amount of F3 is reduced, but the bright odor cannot be reduced. Therefore, although the F3 amount and the effect of reducing the bright odor do not necessarily correlate with each other, they serve as an index of whether or not the irradiated ultraviolet rays effectively affect fats and oils, or the degree of the influence. In the present invention, ultraviolet rays having a wavelength of 200 to 280 nm corresponding to ultraviolet C waves with an intensity effective for reducing the amount of F3 may be used, and include ultraviolet rays and visible rays having wavelengths other than the above wavelengths. You may irradiate a light source.
前記紫外線を照射する際の温度や時間等の条件は、特に問わないが、前記紫外線の照射後の油脂中のＦ３量が１８０ｐｐｍ以下となるように照射することが好ましく、８０ｐｐｍ以下となるように照射することがより好ましく、６０ｐｐｍ以下となるように照射することがさらに好ましく、４５ｐｐｍ以下となるように照射することが特に好ましく、３５ｐｐｍ以下となるように照射することが最も好ましい。Ｆ３量が１８０ｐｐｍを超えると明所臭の低減の効果が得にくい場合がある。また、当該照射は酸素存在下でおこなうことが好ましい。 Conditions such as temperature and time for irradiating the ultraviolet rays are not particularly limited, but it is preferable to irradiate so that the amount of F3 in the oil or fat after the irradiation of the ultraviolet rays is 180 ppm or less, and 80 ppm or less. Irradiation is more preferable, irradiation to 60 ppm or less is further preferable, irradiation to 45 ppm or less is particularly preferable, and irradiation to 35 ppm or less is most preferable. If the amount of F3 exceeds 180 ppm, it may be difficult to obtain the effect of reducing the bright odor. Further, the irradiation is preferably performed in the presence of oxygen.
また、前記紫外線の強度は、特に問わないが、０．１ｍＷ／ｃｍ２以上が好ましく、０．３ｍＷ／ｃｍ２以上がより好ましい。照射強度が０．１ｍＷ／ｃｍ２未満となると、紫外線照射による明所臭の低減の効果が得にくい場合がある。The intensity of the ultraviolet light is not particularly limited, but is preferably 0.1 mW/cm 2 or more, more preferably 0.3 mW/cm 2 or more. If the irradiation intensity is less than 0.1 mW/cm 2 , it may be difficult to obtain the effect of reducing the bright odor due to ultraviolet irradiation.
また、前記紫外線を照射した後、得られた油脂を脱臭処理する工程を含む精製工程をおこなうことが好ましい。これによれば、その処理の際に油分に有臭成分が生じた場合などにおいて、その有臭成分を除去することができる。 Moreover, it is preferable to perform a refining step including a step of deodorizing the resulting oil or fat after irradiating with the ultraviolet rays. According to this, when an odorous component is generated in the oil during the treatment, the odorous component can be removed.
また、前記紫外線を照射する、大豆から搾油された前記油脂の精製状態は特に問わないが、前記油脂が脱ガム処理を経た油脂であることが好ましく、脱酸処理を経た油脂であることがさらに好ましい。脱ガム処理を経た油脂に対して前記紫外線の照射を行うことで、より効果的に明所臭を低減でき、脱酸処理を経た油脂に対して行うことで、さらに効果的に明所臭を低減することができる。 Further, irradiation with the ultraviolet rays, the refined state of the oil and fat extracted from soybean is not particularly limited, but it is preferable that the oil and fat is a fat and oil that has been degummed, and further it is a fat and oil that has been deoxidized. preferable. By irradiating the fats and oils that have been degummed with the above-mentioned ultraviolet rays, the clear odor can be reduced more effectively, and by performing the degreasing and processing on the fats and oils, the clear odor can be more effectively produced. It can be reduced.
前記紫外線を照射する態様は、大豆から搾油された前記油脂が前記紫外線の影響下に曝されるようにすればよく、特に問わないが、例えば、油脂を容器に収容して、その容器の上方、下方等の周囲に設置された所定の紫外線照射装置から前記紫外線を射出して、容器内の油脂に照射したり、油脂をローリー車等で輸送する際に、所定の紫外線照射装置から前記紫外線を射出して、容器内の油脂に照射したり、脱ガム処理工程中・脱酸処理工程中・脱色処理工程中など油脂の精製工程中に照射したり、または油脂を送液する際の配管内で照射したりすることなどが挙げられる。 The aspect of irradiating with the ultraviolet rays may be such that the oil or fat extracted from soybeans is exposed to the influence of the ultraviolet light, and is not particularly limited, but for example, the oil or fat is housed in a container, and the container is placed above the container. , When the ultraviolet rays are emitted from a predetermined ultraviolet irradiation device installed around the lower part or the like to irradiate the oil or fat in the container or when the oil or fat is transported by a lorry car or the like, the ultraviolet light is emitted from the predetermined ultraviolet irradiation device. Piping to inject oil and oil into the container, to irradiate oil and fat in the degumming process, deoxidation process, decolorization process, and other oil purification processes, or to send oil and fat. Illumination and the like can be mentioned.
本発明の他の態様においては、大豆から搾油された油脂に、その油脂中のＦ３量を低減させるように、リポキシゲナーゼを接触させる。 In another embodiment of the present invention, fat and oil extracted from soybean is contacted with lipoxygenase so as to reduce the amount of F3 in the fat and oil.
そのリポキシゲナーゼとしては、大豆由来のものを用いることが好ましい。その場合、水や温水、塩含有水等の水系抽出溶媒で抽出した大豆水抽出物でもよく、あるいはその大豆水抽出物からさらに精製したものであってもよい。また、リポキシゲナーゼは、水溶液、粉体、担体に固定化したもの等のいずれの形態のものを用いてもよいが、後処理等の点で担体に固定化したものが好ましい。 As the lipoxygenase, one derived from soybean is preferably used. In that case, it may be a soybean water extract extracted with an aqueous extraction solvent such as water, warm water, or salt-containing water, or may be one further purified from the soybean water extract. The lipoxygenase may be used in any form such as an aqueous solution, powder, or one immobilized on a carrier, but one immobilized on the carrier is preferable in terms of post-treatment and the like.
前記リポキシゲナーゼを接触させる際の温度やｐＨや時間等の条件は、特に問わないが、好ましくはリポキシゲナーゼの至適温度及び至適ｐＨで前記リポキシゲナーゼと接触後の油脂中のＦ３量が１８０ｐｐｍ以下となるように接触させることが好ましく、８０ｐｐｍ以下となるように接触させることがより好ましく、６０ｐｐｍ以下となるように接触することがさらに好ましく、４５ｐｐｍ以下となるように接触することが特に好ましく、３５ｐｐｍ以下となるように接触することが最も好ましい。Ｆ３量が１８０ｐｐｍを超えると明所臭の低減の効果が得にくい場合がある。 Conditions such as temperature, pH and time for contacting the lipoxygenase are not particularly limited, but preferably the F3 amount in the oil or fat after contact with the lipoxygenase is 180 ppm or less at the optimum temperature and the optimum pH of the lipoxygenase. It is preferable that the contact be performed so as to be 80 ppm or less, more preferable that the contact be 60 ppm or less, and it is further preferable that the contact be 45 ppm or less, and it is particularly preferable that the contact be 35 ppm or less. Most preferably, the contact is such that If the amount of F3 exceeds 180 ppm, it may be difficult to obtain the effect of reducing bright odor.
また、前記リポキシゲナーゼと接触させた後、得られた油脂を脱臭処理する工程を含む精製工程をおこなうことが好ましい。これによれば、その処理の際に油分に有臭成分が生じた場合などにおいて、その有臭成分を除去することができる。 Further, it is preferable to carry out a purification step including a step of deodorizing the resulting oil or fat after contacting with the lipoxygenase. According to this, when an odorous component is generated in the oil during the treatment, the odorous component can be removed.
また、前記リポキシゲナーゼと接触させる、大豆から搾油された前記油脂の精製状態は特に問わないが、前記油脂が脱ガム処理を経た油脂であることが好ましく、脱酸処理を経た油脂であることがさらに好ましい。脱ガム処理を経た油脂に対して前記リポキシゲナーゼの接触を行うことで、より効果的に明所臭を低減でき、脱酸処理を経た油脂に対して行うことで、さらに効果的に明所臭を低減することができる。 Further, the refined state of the oil and fat extracted from soybean, which is brought into contact with the lipoxygenase, is not particularly limited, but it is preferable that the oil and fat is a fat and oil that has been degummed, and further it is a fat and oil that has been deoxidized. preferable. By contacting the lipoxygenase with the oil and fat that has been degummed, it is possible to more effectively reduce the bright odor, and by performing the deoxidized oil and fat, it is possible to more effectively produce the bright odor. It can be reduced.
前記リポキシゲナーゼを接触させる態様は、大豆から搾油された前記油脂とリポキシゲナーゼとを同一の反応系に存在させればよく、特に問わないが、例えば、油脂を収容した容器にリポキシゲナーゼを添加したり、リポキシゲナーゼを収容した容器に油脂を添加したり、またはリポキジゲナーゼを固定化した担体に油脂を通液したりすることなどが挙げられる。 The aspect in which the lipoxygenase is contacted may be such that the oil and fat squeezed from soybeans and lipoxygenase are present in the same reaction system, and there is no particular limitation. Examples of the method include adding oil or fat to a container accommodating oil, or passing oil or fat through a carrier on which lipoxydigenase is immobilized.
一方、本発明のさらに他の態様においては、上記のようにして得られた大豆油を、前記大豆油以外の他の食用油と混合する。 On the other hand, in yet another aspect of the present invention, the soybean oil obtained as described above is mixed with another edible oil other than the soybean oil.
他の食用油としては、特に限定されず、例えば、菜種油、ひまわり油、コーン油、パーム油、パーム分別油などが挙げられる。これらは２種類以上を併用してもよい。 Other edible oils are not particularly limited, and examples thereof include rapeseed oil, sunflower oil, corn oil, palm oil, palm fractionated oil, and the like. These may be used in combination of two or more.
混合油中の前記大豆油の配合割合は、１５質量％以上とすることが好ましく、２０質量％以上とすることが好ましく、３０質量％以上とすることが好ましく、４０質量％以上とすることが好ましく、６０質量％以上とすることが好ましく、８０質量％以上とすることが好ましく、１５質量％以上１００質量％未満とすることがさらにより好ましい。また、混合油中の他の食用油の合計の配合割合は８５質量％以下であることが好ましく、８０質量％以下であることが好ましく、７０質量％以下であることが好ましく、６０質量％以下であることが好ましく、４０質量％以下であることが好ましく、２０質量％以下であることが好ましく、０質量％超８５質量％以下であることがさらに好ましい。すなわち、明所臭の低減された前記大豆油を所定量以上の配合割合で利用することにより、コストを抑えて安価な混合油を提供することができる。 The blending ratio of the soybean oil in the mixed oil is preferably 15% by mass or more, preferably 20% by mass or more, preferably 30% by mass or more, and 40% by mass or more. It is preferably 60% by mass or more, more preferably 80% by mass or more, and even more preferably 15% by mass or more and less than 100% by mass. Further, the total mixing ratio of the other edible oil in the mixed oil is preferably 85% by mass or less, preferably 80% by mass or less, preferably 70% by mass or less, and 60% by mass or less. Is preferable, 40% by mass or less is preferable, 20% by mass or less is preferable, and more than 0% by mass and 85% by mass or less is more preferable. That is, by using the soybean oil having a reduced bright odor at a blending ratio of a predetermined amount or more, it is possible to provide a low-cost mixed oil with a reduced cost.
なお、混合油の場合、前記紫外線の照射や前記リポキシゲナーゼとの接触が有効に油脂に影響を与えたかどうか、あるいはその影響の程度を評価するには、下記式によることが好ましい。 In the case of a mixed oil, it is preferable to use the following formula to evaluate whether or not the irradiation of the ultraviolet rays and the contact with the lipoxygenase effectively affect the fats and oils, or the degree of the influence.
Ａ＝前記紫外線の照射後又はリポキシゲナーゼとの接触後の油脂中のＦ３量（ｐｐｍ）×前記混合油中の前記大豆油の配合割合（質量％）÷１００ A=amount of F3 in fats and oils after irradiation with the ultraviolet rays or after contact with lipoxygenase (ppm)×mixing ratio of the soybean oil in the mixed oil (mass %)÷100
すなわち、例えば後述の実施例の結果を参考にすると、前記混合油中の前記大豆油の配合割合が７０質量％以上であるときには、上記式にて算出される値Ａが６０以下であることが好ましく、３５以下であることがより好ましく、２８以下であることがさらに好ましく、５０質量％以上７０質量％未満であるときには７５以下であることが好ましく、４５以下であることがより好ましく、２５以下であることがさらに好ましく、１５質量％以上５０質量％未満であるときは５０以下であることが好ましく、３５以下であることがより好ましく、２０以下であることがさらに好ましいと言える。また、前記混合油中の前記大豆油の配合割合がいずれの場合でも、上記式にて算出される値Ａが４０未満であることがより好ましく、２３以下であることがさらに好ましいと言える。 That is, for example, referring to the results of Examples described later, when the blending ratio of the soybean oil in the mixed oil is 70% by mass or more, the value A calculated by the above formula may be 60 or less. Preferably, it is 35 or less, more preferably 28 or less, more preferably 75 or less when 50% by mass or more and less than 70% by mass, more preferably 45 or less, and 25 or less. It is more preferable that when the amount is 15% by mass or more and less than 50% by mass, the amount is preferably 50 or less, more preferably 35 or less, and further preferably 20 or less. Further, it can be said that the value A calculated by the above formula is preferably less than 40, and more preferably 23 or less, regardless of the mixing ratio of the soybean oil in the mixed oil.
他方、本発明のさらに別の態様においては、大豆から搾油された油脂に、その油脂中のＦ３量を低減させるように、波長２００〜２８０ｎｍの紫外線を照射する方法を採用することにより、明所臭の低減された大豆油を効率よく得ることができる。また、大豆から搾油された油脂に、その油脂中のＦ３量を低減させるように、リポキシゲナーゼを接触させる方法を採用することにより、明所臭の低減された大豆油を効率よく得ることができる。 On the other hand, in still another aspect of the present invention, by applying a method of irradiating oil and fat extracted from soybeans with ultraviolet rays having a wavelength of 200 to 280 nm so as to reduce the amount of F3 in the oil and fat, Soybean oil with reduced odor can be efficiently obtained. Further, by adopting a method in which the fat or oil extracted from soybeans is contacted with lipoxygenase so as to reduce the amount of F3 in the fat or oil, soybean oil with reduced bright odor can be efficiently obtained.
以下、実施例および比較例を挙げて、本発明をさらに詳細に説明する。しかし、以下の実施例は、本発明を限定するものではない。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. However, the following examples do not limit the present invention.
（大豆脱ガム油、大豆脱酸油、大豆脱臭油の調製）
大豆脱ガム油は、大豆から常法に従って調製した。得られた大豆脱ガム油を常法に従って、脱酸処理をおこない、大豆脱酸油を得た。さらに、大豆脱酸油を常法に従って、脱色処理、脱臭処理をおこない、大豆脱臭油を得た。(Preparation of soybean degummed oil, soybean deoxidized oil, soybean deodorized oil)
Soybean degummed oil was prepared from soybean according to a conventional method. The soybean degummed oil thus obtained was subjected to a deoxidizing treatment according to a conventional method to obtain a soybean deoxidized oil. Further, the soybean deodorized oil was subjected to decolorization treatment and deodorization treatment according to a conventional method to obtain a soybean deodorized oil.
（大豆水抽出物の調製）
大豆を粉砕し、大豆粉砕物１質量部に対し水を６質量部添加し撹拌後、４時間室温にて静置した。静置後、ろ過することで大豆水抽出物を得た。また、リポキシゲナーゼ欠損大豆から同様にリポキシゲナーゼ欠損大豆水抽出物を得た。(Preparation of soybean water extract)
Soybean was crushed, 6 parts by mass of water was added to 1 part by mass of crushed soybean, and the mixture was stirred and allowed to stand at room temperature for 4 hours. After standing, it was filtered to obtain a soybean water extract. In addition, a lipoxygenase-deficient soybean water extract was similarly obtained from the lipoxygenase-deficient soybean.
（油脂中のＦ３量の測定方法）
１．前処理等
試料約８ｍｇを試験管に秤量し、１ｍｌのヘキサンを加えて溶解させた。２Ｍ水酸化カリウム−メタノール溶液を０．１ｍｌ加え、３０秒間撹拌することで、メチルエステル化を行った。遠心分離を行い、上層０．５ｍｌを別の試験管に移した。水０．５ｍｌを加え撹拌後、静置した。上層０．１ｍｌをバイアルに採取し、内部標準物質である重水素にてラベルされたベヘン酸メチル−ｄ３標準品溶液（和光純薬製、２μｇ／ｍｌヘキサン溶液）を０．１ｍｌ加え、撹拌後、ガスクロマトグラフ／質量分析計（ＧＣ／ＭＳ）に供した。(Method of measuring F3 amount in fats and oils)
1. Pretreatment etc. About 8 mg of sample was weighed into a test tube, and 1 ml of hexane was added and dissolved. Methyl esterification was carried out by adding 0.1 ml of 2M potassium hydroxide-methanol solution and stirring for 30 seconds. Centrifugation was performed and 0.5 ml of the upper layer was transferred to another test tube. After adding 0.5 ml of water and stirring, the mixture was left standing. 0.1 ml of the upper layer was collected in a vial, and 0.1 ml of a methyl behenate-d3 standard solution (Wako Pure Chemical Industries, Ltd., 2 μg/ml hexane solution) labeled with deuterium as an internal standard was added and stirred. , Gas chromatograph/mass spectrometer (GC/MS).
２．ＧＣ条件
装置：アジレント社製７８９０Ａ
カラム：アジレント社製 ＨＰ−８８ 長さ６０ｍ、内径２５０μｍ、膜厚０．２μｍ
注入口温度：２５０℃
注入方式：スプリットレス １．５分間
注入量：１μｌ
カラム流量：１ｍｌ／分
移動相：ヘリウム
オーブン条件：１００℃ １分間保持、１０℃／分にて２４０℃まで昇温、２４０℃にて３分間保持
トランスファーライン：２３０℃2. GC conditioner: Agilent 7890A
Column: Agilent HP-88 length 60 m, inner diameter 250 μm, film thickness 0.2 μm
Inlet temperature: 250℃
Injection method: Splitless 1.5 minutes Injection volume: 1 μl
Column flow rate: 1 ml/min Mobile phase: Helium Oven condition: 100°C, hold for 1 minute, temperature rises to 240°C at 10°C/minute, hold at 240°C for 3 minutes Transfer line: 230°C
３．ＭＳ条件
装置：アジレント社製５９７５Ｃ
イオン源：２３０℃
四重極：１５０℃
測定モード：SIM
Ｆ３：定量イオン ｍ／ｚ＝１７９
内部標準物質：定量イオン ｍ／ｚ＝３５７．４3. MS condition device: Agilent 5975C
Ion source: 230 ℃
Quadrupole: 150℃
Measurement mode: SIM
F3: Quantitative ion m/z=179
Internal standard substance: Quantitative ion m/z=357.4
４．定量計算
標品のＦ３（トロントケミカルリサーチ社製）を０、５０、１００、２００、５００ｐｐｍとなるよう菜種油に添加し、検量線サンプルを調製した。各検量線サンプル約４ｍｇを試験管に秤量し、脂肪酸メチル化キット（ナカライテスク社製）を用いて、メチルエステル化を行った。その後、ヘキサン０．５ｍｌを添加、撹拌することで、メチルエステル化物を抽出した。静置後、上層０．１ｍｌをバイアルに採取し、内部標準物質である重水素にてラベルされたベヘン酸メチル−ｄ３標準品溶液（和光純薬製、２μｇ／ｍｌヘキサン溶液）を０．１ｍｌ加え、撹拌後、ガスクロマトグラフ／質量分析計（ＧＣ／ＭＳ）に供した。得られたＦ３の面積値（ｍ／ｚ＝１７９）ならびに内部標準物質の面積値（ｍ／ｚ＝３５７．４）の比より検量線を作成した。作成した検量線を用いて、試料中のＦ３量（ｐｐｍ）を算出した。4. Quantitative Calculation F3 (manufactured by Toronto Chemical Research Co.) was added to rapeseed oil so as to have a concentration of 0, 50, 100, 200, 500 ppm to prepare a calibration curve sample. About 4 mg of each calibration curve sample was weighed in a test tube, and methyl esterification was performed using a fatty acid methylation kit (manufactured by Nacalai Tesque, Inc.). Then, 0.5 ml of hexane was added and the mixture was stirred to extract the methyl esterified product. After standing, 0.1 ml of the upper layer was collected in a vial, and 0.1 ml of methyl behenate-d3 standard solution (2 μg/ml hexane solution manufactured by Wako Pure Chemical Industries) labeled with deuterium as an internal standard substance. In addition, after stirring, it was subjected to a gas chromatograph/mass spectrometer (GC/MS). A calibration curve was prepared from the ratio of the obtained area value of F3 (m/z=179) and the area value of the internal standard substance (m/z=357.4). The F3 amount (ppm) in the sample was calculated using the prepared calibration curve.
（明所臭の評価）
２０ｍｌ容ガラスバイアル瓶に試料１０ｇを入れ、密栓し、蛍光灯下（２４℃、１０００ルクス（Ｌｕｘ））で１週間保存後、１００℃に加熱した際の明所臭の有無を評価した。評価は、３名のパネラーにより、以下の評価基準で行い、全パネラーの平均的な評価によって表示した。
Ａ 明所臭がない
Ｂ 明所臭がほとんどない
Ｃ 明所臭がわずかにある
Ｄ 明所臭がある
(Evaluation of bright odor)
10 g of the sample was placed in a 20 ml glass vial, sealed, and stored under a fluorescent lamp (24° C., 1000 lux (Lux)) for 1 week, and then the presence or absence of a bright odor when heated to 100° C. was evaluated. The evaluation was performed by the three panelists according to the following evaluation criteria, and the average evaluation of all panelists was shown.
A There is no bright spot odor B There is almost no bright spot smell C There is a slight bright spot smell D There is a bright spot smell
以下、紫外線を照射することによる明所臭の低減の効果を確認した。 Hereinafter, the effect of reducing bright odor by irradiating ultraviolet rays was confirmed.
＜試験例１＞（紫外線Ｃ波（UVC）の照射）
大豆脱臭油２００ｇを８．５ｃｍガラスシャーレに入れ、２４℃にて、２５４ｎｍの紫外線（装置Handy UV Lamp SLUV-4、AZ ONE社製、紫外線Ａ波（UVA）強度：検出されず、UVC強度：０．６ｍＷ／ｃｍ２、照度２５０Lux）を表１に示す時間照射した。照射した後、油脂中のＦ３量を測定した。紫外線照射後の大豆脱臭油を脱臭処理にて精製した後、明所臭の評価をおこなった。結果を表１に示す。<Test Example 1> (UV C wave (UVC) irradiation)
200 g of soybean deodorized oil was put into an 8.5 cm glass petri dish, and ultraviolet rays of 254 nm (apparatus Handy UV Lamp SLUV-4, manufactured by AZ ONE, ultraviolet A wave (UVA) intensity: not detected, UVC intensity: 24° C.) Irradiation with 0.6 mW/cm 2 and illuminance of 250 Lux) for the time shown in Table 1. After irradiation, the amount of F3 in the oil/fat was measured. The soybean deodorized oil after ultraviolet irradiation was refined by deodorizing treatment, and then the light odor was evaluated. The results are shown in Table 1.
その結果、表１に示したように、大豆脱臭油に２５４ｎｍの紫外線Ｃ波をＦ３量が５０ｐｐｍ以下となるように照射することで、明所臭の低減された大豆油を得ることができた。また、３９ｐｐｍ以下とすることで、さらに明所臭を低減させることができ、３１ｐｐｍ以下とすることでその効果は顕著であった。 As a result, as shown in Table 1, soybean deodorized oil was irradiated with ultraviolet C waves of 254 nm so that the F3 content was 50 ppm or less, soybean oil with a reduced bright odor could be obtained. .. Further, by setting the content to 39 ppm or less, the bright odor can be further reduced, and by setting it to 31 ppm or less, the effect was remarkable.
［調製例１］（マヨネーズの調製）
試験例１の実施例１−４で得られた大豆油を用いて、常法によりマヨネーズ（当該大豆油７８質量％）を調製したところ、明所臭の低減したマヨネーズを得ることができた。[Preparation Example 1] (Preparation of mayonnaise)
Using the soybean oil obtained in Example 1-4 of Test Example 1 to prepare mayonnaise (78% by mass of the soybean oil) by a conventional method, it was possible to obtain mayonnaise with reduced bright odor.
＜試験例２＞（紫外線Ｃ波（UVC）の照射）
大豆脱ガム油または大豆脱酸油２００ｇを８．５ｃｍガラスシャーレに入れ、２４℃にて、２５４ｎｍの紫外線（試験例１と同じ条件の紫外線Ｃ波（UVC））を１４０時間照射した。照射した後、油脂中のＦ３量を測定した。紫外線照射後の大豆脱ガム油は、脱酸・脱色・脱臭処理にて精製をし、また、紫外線照射後の大豆脱酸油は、脱色・脱臭処理にて精製をし、それぞれ精製後の大豆油の明所臭の評価をおこなった。結果を表２に示す。<Test Example 2> (UV C wave (UVC) irradiation)
200 g of soybean degummed oil or soybean deoxidized oil was placed in an 8.5 cm glass petri dish and irradiated with ultraviolet rays of 254 nm (ultraviolet C wave (UVC) under the same conditions as in Test Example 1) at 24° C. for 140 hours. After irradiation, the amount of F3 in the oil/fat was measured. Soybean degummed oil after UV irradiation is refined by deoxidation/decolorization/deodorization treatment, and soybean deoxidized oil after UV irradiation is refined by decolorization/deodorization treatment. The light odor of soybean oil was evaluated. The results are shown in Table 2.
その結果、表２に示したように、大豆脱ガム油や大豆脱酸油に対し、それらの油脂中のＦ３量を低減させるように紫外線Ｃ波を照射することで、明所臭の低減された大豆油を得ることができた。なかでも脱酸処理の工程を経た大豆脱酸油に紫外線Ｃ波を照射することで、より効果的に明所臭を低減できることがわかった。 As a result, as shown in Table 2, soybean-degummed oil and soybean-deoxidized oil were irradiated with ultraviolet C waves so as to reduce the amount of F3 in the oils and fats, thereby reducing the bright odor. Soybean oil could be obtained. It has been found that, by irradiating soybean deoxidized oil that has undergone the deoxidation treatment step with ultraviolet C waves, the odor in the clear can be reduced more effectively.
＜試験例３＞（紫外線Ａ波（UVA）の照射）
大豆脱臭油２００ｇを８．５ｃｍガラスシャーレに入れ、２４℃にて、３６５ｎｍの紫外線（装置 Handy UV Lamp SLUV-4、AZ ONE社製、UVA強度：１．０ｍＷ／ｃｍ２、UVC強度：検出されず、照度３８０Lux）を１７０時間照射した。照射した後、油脂中のＦ３量を測定した。紫外線照射後の大豆脱臭油を脱臭処理にて精製した後、明所臭の評価をおこなった。結果を表３に示す。<Test Example 3> (UV A wave (UVA) irradiation)
200 g of soybean deodorized oil was placed in an 8.5 cm glass petri dish, and ultraviolet rays of 365 nm (apparatus Handy UV Lamp SLUV-4, manufactured by AZ ONE, UVA intensity: 1.0 mW/cm 2 , UVC intensity: detected at 24° C.) No, the illuminance was 380 Lux) for 170 hours. After irradiation, the amount of F3 in the oil/fat was measured. The soybean deodorized oil after ultraviolet irradiation was refined by deodorizing treatment, and then the light odor was evaluated. The results are shown in Table 3.
その結果、表３に示したように、大豆脱臭油に３６５ｎｍの紫外線Ａ波を照射した場合、その照射により、その油脂中のＦ３量が低減したにもかかわらず、明所臭は低減できなかった。 As a result, as shown in Table 3, when the soybean deodorized oil was irradiated with 365 nm UV A wave, the irradiation did not reduce the bright-smelling odor, although the F3 amount in the oil and fat was reduced. It was
＜試験例４＞（可視光の照射）
大豆脱臭油２００ｇを８．５ｃｍガラスシャーレに入れ、２４℃にて、可視光（装置 蛍光灯スタンド BT K-7567、小泉産業社製、UVA強度：検出されず、UVC強度：検出されず、照度１０００Lux）を１週間照射した。照射した後、油脂中のＦ３量を測定した。紫外線照射後の大豆脱臭油は脱臭処理により精製した後、明所臭の評価をおこなった。結果を表４に示す。<Test Example 4> (irradiation with visible light)
200 g of soybean deodorized oil was placed in an 8.5 cm glass petri dish, and at 24°C, visible light (apparatus fluorescent lamp stand BTK-7567, Koizumi Sangyo Co., Ltd., UVA intensity: not detected, UVC intensity: not detected, illuminance 1000 Lux) was irradiated for 1 week. After irradiation, the amount of F3 in the oil/fat was measured. The soybean deodorized oil after ultraviolet irradiation was refined by deodorizing treatment and then evaluated for bright odor. The results are shown in Table 4.
その結果、表４に示したように、大豆脱臭油に可視光を照射した場合、その照射により、その油脂中のＦ３量が低減したにもかかわらず、明所臭は低減できなかった。 As a result, as shown in Table 4, when the soybean deodorized oil was irradiated with visible light, the bright odor could not be reduced although the amount of F3 in the oil and fat was reduced by the irradiation.
＜試験例５＞（リポキシゲナーゼとの接触）
大豆脱臭油１質量部に対し、大豆水抽出物あるいはリポキシゲナーゼ欠損大豆水抽出物を９質量部配合し、ホモミキサーにて撹拌の後、４℃にて２４時間静置した。静置後、溶剤抽出にて油脂を回収した。回収後、油脂中のＦ３量を測定した。リポキシゲナーゼとの接触後の油脂を脱色処理ならびに脱臭処理にて精製した後、明所臭の評価をおこなった。結果を表５に示す。<Test Example 5> (contact with lipoxygenase)
To 1 part by mass of soybean deodorized oil, 9 parts by mass of a soybean water extract or a lipoxygenase-deficient soybean water extract was blended, stirred with a homomixer, and allowed to stand at 4° C. for 24 hours. After standing, the oil and fat was recovered by solvent extraction. After the collection, the amount of F3 in the oil/fat was measured. After the oil and fat after contact with lipoxygenase were purified by decolorization and deodorization, the light odor was evaluated. The results are shown in Table 5.
その結果、表５に示したように、大豆水抽出物と大豆脱臭油を混合することにより、その油脂中のＦ３量が低下し、明所臭の低減した大豆油を得ることができた。一方、リポキシゲナーゼの欠損した大豆水抽出物では、同様の処理をおこなっても、Ｆ３量が低下せず、明所臭を低減させることはできなかった。 As a result, as shown in Table 5, by mixing the soybean water extract and the soybean deodorized oil, the amount of F3 in the oil and fat was decreased, and soybean oil with a reduced bright odor could be obtained. On the other hand, with the soybean water extract deficient in lipoxygenase, even when the same treatment was performed, the amount of F3 did not decrease, and the bright odor could not be reduced.
＜試験例６＞（混合油の調製 その１）
試験例１の比較例１−１〜３、実施例１−１〜２で得られた大豆油を用いて、表６に示す割合で、菜種油（株式会社Ｊ−オイルミルズ社製）と混合した。得られた混合油について、明所臭の評価をおこなった。結果を表６に示す。
The soybean oils obtained in Comparative Examples 1-1 to 1-3 and Examples 1-1 to 1-2 of Test Example 1 were mixed with rapeseed oil (manufactured by J-Oil Mills Co., Ltd.) at a ratio shown in Table 6. .. The obtained mixed oil was evaluated for bright odor. The results are shown in Table 6.
その結果、表６で示したように、大豆油８０質量％と菜種油２０質量％との混合油では、大豆油のＦ３量が５０ｐｐｍ以下（Ａ値としては４０ｐｐｍ以下）で明所臭を低減できることがわかった。 As a result, as shown in Table 6, in the mixed oil of soybean oil 80% by mass and rapeseed oil 20% by mass, the clear odor can be reduced when the soybean oil F3 content is 50 ppm or less (A value is 40 ppm or less). I understood.
＜試験例７＞（混合油の調製 その２）
試験例１の比較例１−１〜３、実施例１−１〜２で得られた大豆油を用いて、表７に示す割合で、菜種油（株式会社Ｊ−オイルミルズ社製）と混合した。得られた混合油について、明所臭の評価をおこなった。結果を表７に示す。<Test Example 7> (Preparation of mixed oil 2)
The soybean oils obtained in Comparative Examples 1-1 to 1-3 and Examples 1-1 to 1-2 of Test Example 1 were mixed with rapeseed oil (manufactured by J-Oil Mills Co., Ltd.) in the proportions shown in Table 7. .. The obtained mixed oil was evaluated for bright odor. The results are shown in Table 7.
その結果、表７で示したように、大豆油６０質量％と菜種油４０質量％との混合油では、大豆油のＦ３量が１１８ｐｐｍ以下（Ａ値としては７１ｐｐｍ以下）で明所臭を低減できることがわかった。 As a result, as shown in Table 7, in the mixed oil of 60% by mass of soybean oil and 40% by mass of rapeseed oil, the F3 amount of soybean oil can be 118 ppm or less (71 ppm or less as the A value) to reduce the clear odor. I understood.
＜試験例８＞（混合油の調製 その３）
試験例１の比較例１−１〜３、実施例１−１で得られた大豆油を用いて、表８に示す割合で、菜種油（株式会社Ｊ−オイルミルズ社製）と混合した。得られた混合油について、明所臭の評価をおこなった。結果を表８に示す。<Test Example 8> (Preparation of mixed oil 3)
The soybean oils obtained in Comparative Examples 1-1 to 1-3 and Example 1-1 of Test Example 1 were mixed with rapeseed oil (manufactured by J-Oil Mills Co., Ltd.) in the proportions shown in Table 8. The obtained mixed oil was evaluated for bright odor. The results are shown in Table 8.
その結果、表８で示したように、大豆油４０質量％と菜種油６０質量％との混合油では、大豆油のＦ３量が１１８ｐｐｍ以下（Ａ値としては４７ｐｐｍ以下）で明所臭を低減できることがわかった。 As a result, as shown in Table 8, in the mixed oil of 40% by mass of soybean oil and 60% by mass of rapeseed oil, the clear odor can be reduced when the F3 amount of soybean oil is 118 ppm or less (A value is 47 ppm or less). I understood.
＜試験例９＞（混合油の調製 その４）
試験例１の比較例１−１〜３、実施例１−１で得られた大豆油を用いて、表９に示す割合で、菜種油（株式会社Ｊ−オイルミルズ社製）と混合した。得られた混合油について、明所臭の評価をおこなった。結果を表９に示す。<Test Example 9> (Preparation of mixed oil Part 4)
The soybean oils obtained in Comparative Examples 1-1 to 1-3 and Example 1-1 of Test Example 1 were mixed with rapeseed oil (manufactured by J-Oil Mills Co., Ltd.) in the proportions shown in Table 9. The obtained mixed oil was evaluated for bright odor. The results are shown in Table 9.
その結果、表９で示したように、大豆油３０質量％と菜種油７０質量％との混合油では、大豆油のＦ３量が１１８ｐｐｍ以下（Ａ値としては３５ｐｐｍ以下）で明所臭を低減できることがわかった。 As a result, as shown in Table 9, in the mixed oil of 30% by mass of soybean oil and 70% by mass of rapeseed oil, the F3 amount of soybean oil can be 118 ppm or less (35 ppm or less as the A value) to reduce bright odor. I understood.
＜試験例１０＞（混合油の調製 その５）
試験例１の比較例１−１〜３で得られた大豆油を用いて、表１０に示す割合で、菜種油（株式会社Ｊ−オイルミルズ社製）と混合した。得られた混合油について、明所臭の評価をおこなった。結果を表１０に示す。<Test Example 10> (Preparation of mixed oil 5)
The soybean oils obtained in Comparative Examples 1-1 to 1-3 of Test Example 1 were mixed with rapeseed oil (manufactured by J-Oil Mills Co., Ltd.) at a ratio shown in Table 10. The obtained mixed oil was evaluated for bright odor. The results are shown in Table 10.
その結果、表１０で示したように、大豆油２０質量％と菜種油８０質量％との混合油では、大豆油のＦ３量が１１８ｐｐｍ以下（Ａ値としては２４ｐｐｍ以下）で明所臭を低減できることがわかった。 As a result, as shown in Table 10, in the mixed oil of 20% by mass of soybean oil and 80% by mass of rapeseed oil, the F3 amount of soybean oil can be 118 ppm or less (24 ppm or less as the A value) to reduce the clear odor. I understood.
＜試験例１１＞（混合油の調製 その６）
試験例１の比較例１−１、実施例１−２で得られた大豆油を用いて、表１１に示す割合で、ハイオレイックひまわり油（株式会社Ｊ−オイルミルズ社製）と混合した。得られた混合油について、明所臭の評価をおこなった。結果を表１１に示す。<Test Example 11> (Preparation of mixed oil 6)
The soybean oils obtained in Comparative Example 1-1 and Example 1-2 of Test Example 1 were mixed with high oleic sunflower oil (manufactured by J-Oil Mills Co., Ltd.) in the proportions shown in Table 11. The obtained mixed oil was evaluated for bright odor. The results are shown in Table 11.
その結果、表１１で示したように、菜種油に代えて、ハイオレイックひまわり油４０質量％を大豆油６０質量％と混合しても、Ｆ３量が３９ｐｐｍ以下（Ａ値としては２３ｐｐｍ以下）で、同様に明所臭を低減できることがわかった。 As a result, as shown in Table 11, even if 40% by mass of high oleic sunflower oil was mixed with 60% by mass of soybean oil instead of rapeseed oil, the F3 content was 39 ppm or less (A value was 23 ppm or less), and the same. It was found that the bright odor can be reduced.
Claims (13)
Ａ＝前記紫外線の照射後又は前記リポキシゲナーゼとの接触後の該油脂中の前記３，４−ジメチル−５−ペンチル−２−フランノナン酸量（ｐｐｍ）×前記混合油中の前記大豆油の配合割合（質量％）÷１００ …（１）
The method for producing a mixed oil according to any one of claims 10 to 12, wherein a value A calculated by the following formula (1) is less than 40.
A = the amount of 3,4-dimethyl-5-pentyl-2-furanonanoic acid (ppm) in the oil/fat after the irradiation with the ultraviolet rays or the contact with the lipoxygenase×the mixing ratio of the soybean oil in the mixed oil (Mass %)/100... (1)
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| WO2019173292A1 (en) * | 2018-03-06 | 2019-09-12 | Bunge Global Innovation, Llc | Methods for bleaching phospholipid compositions |
| JPWO2022158583A1 (en) * | 2021-01-21 | 2022-07-28 |
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| JPH01138298A (en) * | 1987-07-24 | 1989-05-31 | Fuji Oil Co Ltd | Production of refined soybean oil |
| FR2696192B1 (en) * | 1992-09-28 | 1994-12-02 | Bfa Lab | Process for the enzymatic preparation of ionones and volatile aldehydes. |
| JP3427490B2 (en) * | 1994-05-31 | 2003-07-14 | 味の素株式会社 | Edible fats and oils products with low light odor |
| JPH10191885A (en) * | 1997-01-14 | 1998-07-28 | Nisshin Oil Mills Ltd:The | Soybean/rapeseed blended oil |
| JP3768497B2 (en) * | 2003-08-29 | 2006-04-19 | ピースビーンズ株式会社 | Method for producing mayonnaise-style sauce using soybean and mayonnaise-style sauce using soybean |
| CN102746943B (en) * | 2012-07-20 | 2013-06-05 | 嘉祥县嘉冠油脂化工有限公司 | Cold pressing preparation process of non-transgenic soybean oil |
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