WO2017033674A1 - Procédé de production d'huile de soja, procédé de production d'huile mixte, et procédé d'inhibition de l'odeur de l'huile de soja dans les endroits lumineux - Google Patents

Procédé de production d'huile de soja, procédé de production d'huile mixte, et procédé d'inhibition de l'odeur de l'huile de soja dans les endroits lumineux Download PDF

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Publication number
WO2017033674A1
WO2017033674A1 PCT/JP2016/072476 JP2016072476W WO2017033674A1 WO 2017033674 A1 WO2017033674 A1 WO 2017033674A1 JP 2016072476 W JP2016072476 W JP 2016072476W WO 2017033674 A1 WO2017033674 A1 WO 2017033674A1
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Prior art keywords
oil
soybean
amount
producing
mixed
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PCT/JP2016/072476
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English (en)
Japanese (ja)
Inventor
貴士 佐野
遼 岡部
舞子 岩橋
成人 牧田
潤 今義
俊郎 佐藤
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株式会社Ｊ－オイルミルズ
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Priority to JP2017536709A priority Critical patent/JP6714001B2/ja
Publication of WO2017033674A1 publication Critical patent/WO2017033674A1/fr

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    • 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

Definitions

  • the present invention relates to a method for producing soybean oil, and more particularly, to a method for producing soybean oil with reduced photopic odor, a method for producing a mixed oil blended with the soybean oil, and a method for suppressing the photopic odor of soybean oil. .
  • soybean oil becomes odorless after the refining process, a special odor called a return odor occurs during storage.
  • This return odor is said to be the largest cause of light during storage, and is also referred to as “lighthouse odor”. Traditionally, this light odor has limited the amount of soy oil blended into salad oil and mayonnaise.
  • Patent Document 1 has a step of subjecting soybean seeds to pressing without using an organic solvent, and the step before the treatment is performed at a temperature of 90 ° C. or lower.
  • a manufacturing method is disclosed.
  • the Example describes that the soybean oil obtained by the production method has a better flavor after exposure than the comparative example.
  • An object of the present invention is to provide a method for producing soybean oil with reduced photopic odor, a method for producing a mixed oil containing the soybean oil, and a method for suppressing the photopic odor of soybean oil.
  • oils and fats squeezed from soybeans have been subjected to 3,4-dimethyl-5-pentyl-2-furanonanoic acid (hereinafter referred to as “F3”). It was found that the photoodor of soybean oil can be reduced by irradiating ultraviolet rays of a specific wavelength or contacting lipoxygenase so as to reduce the amount, and the present invention has been completed.
  • F3 3,4-dimethyl-5-pentyl-2-furanonanoic acid
  • the first aspect of the present invention provides a method for producing soybean oil comprising a step of irradiating an oil and fat squeezed from soybean with ultraviolet rays having a wavelength of 200 to 280 nm so as to reduce the amount of F3 in the oil and fat. It is to provide.
  • the method for producing soybean oil according to the first aspect of the present invention preferably includes a step of deodorizing the fats and oils obtained in the above step.
  • the oil and fat squeezed from soybean is an oil and fat that has been degummed.
  • the 2nd aspect of this invention provides the manufacturing method of soybean oil including the process of making lipoxygenase contact the oil and fat squeezed from soybean so that the amount of F3 in the oil and fat may be reduced.
  • the lipoxygenase is preferably derived from soybean.
  • the oil / fat extracted from soybean is an oil / fat that has undergone degumming treatment.
  • the amount of F3 in the oil after irradiation with the ultraviolet light or after contact with the lipoxygenase is 180 ppm or less. More preferably, the amount of F3 is 60 ppm or less.
  • the fat and oil squeezed from soybean is irradiated with ultraviolet rays having a wavelength of 200 to 280 nm or brought into contact with lipoxygenase so as to reduce the amount of F3 in the fat and oil.
  • the manufacturing method of mixed oil including the process of mixing the soybean oil obtained by this with edible oils other than the said soybean oil is provided.
  • 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.
  • 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. It is preferable that
  • the value A calculated by the following formula (1) is preferably less than 40.
  • A the amount of F3 in the oil after exposure to the ultraviolet light or after contact with the lipoxygenase (ppm) ⁇ the blending ratio (mass%) of the soybean oil in the mixed oil ⁇ 100 (1)
  • the fat extracted from soybean is irradiated with ultraviolet rays having a wavelength of 200 to 280 nm or brought into contact with lipoxygenase so as to reduce the amount of F3 in the fat.
  • the present invention provides a method for reducing the photopic odor of soybean oil.
  • the present invention it is possible to provide a method for producing soybean oil with reduced photopic odor, a method for producing a mixed oil containing the soybean oil, and a method for suppressing the photopic odor of soybean oil.
  • edible oils are produced by obtaining crude oil by squeezing and / or solvent extraction from oil raw materials and then further refining the crude oil.
  • Compressed extraction is performed by applying high pressure to the raw material to squeeze out the oil in the cells.
  • Squeezed extraction is suitable for plant materials with relatively high oil content such as sesame.
  • Solvent extraction is performed by bringing oil seeds as raw materials into contact with the residue after pressing or squeezing and extracting the oil as a solvent solution, and distilling off the solvent from the resulting solution to obtain the oil. Is. Solvent extraction is suitable for raw materials with low oil content such as soybean. Hexane is used as the solvent.
  • 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 operations between them are “degumming treatment” and “deacidification”. In general, degumming treatment, deoxidation treatment, decolorization treatment, and deodorization treatment are adopted as the steps of “treatment”, “decolorization treatment”, and “deodorization treatment”.
  • the degumming treatment is, for example, a step of hydrating and removing the gums mainly composed of phospholipids contained in the oil.
  • the deoxidation treatment is a step of removing free fatty acids contained in the oil as soap, for example, by treatment with alkaline water.
  • the decolorization treatment is a step of removing the pigment contained in the oil by adsorbing it on the activated clay, for example.
  • the deodorization treatment is a step of removing volatile odorous components contained in the oil by, for example, steam distillation under reduced pressure.
  • the “fat and oil squeezed from soybean” includes fats and oils in the middle of the refining process of a general edible oil as described above, and also includes soybean oil after finishing them. Meaning.
  • fats and oils squeezed from soybeans are irradiated with ultraviolet rays having a wavelength of 200 to 280 nm so as to reduce the amount of F3 in the fats and oils.
  • F3 (3,4-dimethyl-5-pentyl-2-furanonanoic acid) is usually present in an ester-bonded state with glycerol in fats and oils. Therefore, in this specification, the amount of F3 in fats and oils mainly refers to the amount of F3 in an ester-bonded state with glycerol.
  • Ultraviolet rays are classified into three types according to wavelength length, and are classified into ultraviolet 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.
  • ultraviolet rays having a wavelength of 200 to 280 nm corresponding to ultraviolet C waves are used in the present invention.
  • ultraviolet rays having a wavelength of 220 to 270 nm are used.
  • ultraviolet light having a wavelength of 365 nm which is an ultraviolet A wave
  • visible light cannot reduce the photopic odor although the amount of F3 is reduced.
  • the amount of F3 and the light odor reduction effect do not necessarily correlate, it is an indicator of whether or not the irradiated ultraviolet rays have effectively affected the oil or fat, or the degree of the effect.
  • it is sufficient to use an ultraviolet ray having a wavelength of 200 to 280 nm corresponding to the ultraviolet C wave with an intensity effective for reducing the amount of F3, and includes ultraviolet rays other than the above wavelengths, visible light, and the like.
  • a light source may be irradiated.
  • Conditions such as temperature and time at the time of irradiation with the ultraviolet rays are not particularly limited, but irradiation is preferably performed so that the amount of F3 in the oil and fat after the ultraviolet irradiation is 180 ppm or less, and 80 ppm or less. Irradiation is more preferable, irradiation is more preferable to be 60 ppm or less, irradiation is particularly preferably performed to be 45 ppm or less, and irradiation is most preferably performed to be 35 ppm or less. If the amount of F3 exceeds 180 ppm, it may be difficult to obtain the effect of reducing the bright odor.
  • the irradiation is preferably performed in the presence of oxygen.
  • the intensity of the ultraviolet rays is not particularly limited, but is preferably 0.1 mW / cm 2 or more, and more preferably 0.3 mW / cm 2 or more.
  • the irradiation intensity is less than 0.1 mW / cm 2 , it may be difficult to obtain the effect of reducing the bright odor by ultraviolet irradiation.
  • a purification step including a step of deodorizing the obtained fat after irradiating the ultraviolet rays. According to this, in the case where an odorous component is generated in the oil during the treatment, the odorous component can be removed.
  • the refined state of the oil / fat extracted from soybean, which is irradiated with the ultraviolet rays is not particularly limited. preferable.
  • the photopic odor can be reduced more effectively. Can be reduced.
  • the mode of irradiating with ultraviolet rays is not particularly limited as long as the fats and oils squeezed from soybeans are exposed to the influence of the ultraviolet rays.
  • the ultraviolet rays are emitted from a predetermined ultraviolet irradiation device installed around the lower part, etc. to irradiate the fats and oils in the container, or when the fats and oils are transported by a lorry vehicle, the ultraviolet rays are emitted from the predetermined ultraviolet irradiation device.
  • To irradiate the oil and fat in the container to irradiate the oil and fat during the degumming process, during the deoxidation process, and during the decolorization process, or to feed the oil and fat And so on.
  • lipoxygenase is brought into contact with fat and oil squeezed from soybean so as to reduce the amount of F3 in the fat and oil.
  • soybean-derived lipoxygenase it is preferable to use soybean-derived lipoxygenase.
  • the soybean water extract extracted with water-type extraction solvents such as water, warm water, salt containing water, may be used, and what was further refine
  • the lipoxygenase may be in any form such as an aqueous solution, powder, or immobilized on a carrier, but is preferably immobilized on the carrier in terms of post-treatment.
  • Conditions such as temperature, pH, and time when contacting the lipoxygenase are not particularly limited, but preferably the amount of F3 in the fat after contact with the lipoxygenase is 180 ppm or less at the optimal temperature and pH of the lipoxygenase. It is preferable to contact so that it may become 80 ppm or less, it is more preferable to contact so that it may become 60 ppm or less, It is especially preferable to contact so that it may become 45 ppm or less, and 35 ppm or less It is most preferable to make contact. If the amount of F3 exceeds 180 ppm, it may be difficult to obtain the effect of reducing the bright odor.
  • a purification step including a step of deodorizing the obtained fat after contacting with the lipoxygenase. According to this, in the case where an odorous component is generated in the oil during the treatment, the odorous component can be removed.
  • the state of purification of the oil / fat extracted from soybean, which is brought into contact with the lipoxygenase is not particularly limited, but the oil / fat is preferably an oil / fat that has undergone a degumming treatment, and more preferably a fat / oil that has undergone a deoxidation treatment. preferable.
  • the photopic odor can be reduced more effectively. Can be reduced.
  • the aspect in which the lipoxygenase is brought into contact is not particularly limited as long as the fat and lipoxygenase squeezed from soybeans are present in the same reaction system.
  • the soybean oil obtained as described above is mixed with an edible oil other than the soybean oil.
  • edible oils are not particularly limited, and examples thereof include rapeseed oil, sunflower oil, corn oil, palm oil, and palm fractionated oil. Two or more of these may be used in combination.
  • 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. Preferably, 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 blending ratio of other edible oils 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. It is preferable that it is 40 mass% or less, it is preferable that it is 20 mass% or less, and it is more preferable that it is more than 0 mass% and 85 mass% or less. That is, by using the soybean oil with a reduced photopic odor in a blending ratio of a predetermined amount or more, it is possible to provide an inexpensive mixed oil at a reduced cost.
  • A F3 amount (ppm) in fats and oils after irradiation with ultraviolet rays or contact with lipoxygenase ⁇ mixing ratio of the soybean oil in the mixed oil (mass%) ⁇ 100
  • the value A calculated by the above formula may be 60 or less. Preferably, it is 35 or less, more preferably 28 or less, and preferably 50 or less, more preferably 45 or less, and even more preferably 25 or less when it is 50 to 70% by mass. More preferably, when it is 15% by mass or more and less than 50% by mass, it is preferably 50 or less, more preferably 35 or less, and even more preferably 20 or less. Moreover, it can be said that the value A calculated by the above formula is more preferably less than 40 and even more preferably 23 or less regardless of the blending ratio of the soybean oil in the mixed oil.
  • soybean oil with reduced odor can be obtained efficiently.
  • soybean oil with reduced photopic odor can be efficiently obtained by adopting a method in which lipoxygenase is brought into contact with oil and fat squeezed from soybean so as to reduce the amount of F3 in the oil and fat.
  • soybean degummed oil was prepared from soybean according to a conventional method.
  • the obtained soybean degummed oil was subjected to deoxidation treatment according to a conventional method to obtain soybean deoxidized oil.
  • soybean deoxidized oil was subjected to decolorization treatment and deodorization treatment according to a conventional method to obtain soybean deodorized oil.
  • soybean water extract (Preparation of soybean water extract) The soybean was pulverized, 6 parts by mass of water was added to 1 part by mass of the pulverized soybean, and the mixture was stirred and allowed to stand at room temperature for 4 hours. After standing, the soybean water extract was obtained by filtering. Similarly, a lipoxygenase-deficient soybean water extract was obtained from lipoxygenase-deficient soybean.
  • GC condition device 7890A manufactured by Agilent Column: HP-88, manufactured by Agilent, 60 m in length, 250 ⁇ m in inner diameter, 0.2 ⁇ m in film thickness
  • Inlet temperature 250 ° C
  • Injection method Splitless 1.5 minutes
  • Injection volume 1 ⁇ l
  • Mobile phase Helium oven conditions: 100 ° C held for 1 minute, heated to 240 ° C at 10 ° C / minute, held at 240 ° C for 3 minutes Transfer line: 230 ° C
  • MS condition device 5975C manufactured by Agilent Ion source: 230 ° C
  • Quadrupole 150 ° C
  • UVC Ultraviolet C-wave
  • 200 g of soybean deodorized oil was put in an 8.5 cm glass petri dish, and at 24 ° C., ultraviolet light of 254 nm (apparatus Handy UV Lamp SLUV-4, manufactured by AZ ONE, ultraviolet A wave (UVA) intensity: not detected, UVC intensity: 0.6 mW / cm 2 and illuminance 250 Lux) were irradiated for the time shown in Table 1. After irradiation, the amount of F3 in the fat was measured. After the soybean deodorized oil after ultraviolet irradiation was purified by deodorizing treatment, the photoodor was evaluated. The results are shown in Table 1.
  • 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 photoodor.
  • ⁇ Test Example 2> (Ultraviolet C wave (UVC) irradiation) 200 g of soybean degummed oil or soybean deoxidized oil was put 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 fat was measured. Soybean degummed oil after UV irradiation is refined by deoxidation, decolorization, and deodorization treatment. Soybean deoxidized oil after UV irradiation is refined by decolorization and deodorization treatment. We evaluated the light odor of soybean oil. The results are shown in Table 2.
  • UVA Ultraviolet A wave
  • 200 g of soybean deodorized oil was put in an 8.5 cm glass petri dish, and ultraviolet rays of 365 nm (device Handy UV Lamp SLUV-4, manufactured by AZ ONE, UVA intensity: 1.0 mW / cm 2 , UVC intensity: detected) Irradiance was 380 Lux) for 170 hours.
  • the amount of F3 in the fat was measured.
  • the soybean deodorized oil after ultraviolet irradiation was purified by deodorizing treatment the photoodor was evaluated. The results are shown in Table 3.
  • ⁇ Test Example 5> Contact with lipoxygenase 9 parts by mass of soybean water extract or lipoxygenase-deficient soybean water extract was mixed with 1 part by mass of soybean deodorized oil, stirred with a homomixer, and allowed to stand at 4 ° C. for 24 hours. After standing, the oil was collected by solvent extraction. After recovery, the amount of F3 in the fat was measured. The oil and fat after contact with lipoxygenase was purified by decolorization and deodorization, and then the photoodor was evaluated. The results are shown in Table 5.
  • ⁇ Test Example 6> (Preparation of mixed oil, part 1) Using the soybean oils obtained in Comparative Examples 1-1 to 1-3 and Examples 1-1 to 2 in Test Example 1 and mixed with rapeseed oil (manufactured by J-Oil Mills Co., Ltd.) in the proportions shown in Table 6. . About the obtained mixed oil, the photopic odor was evaluated. The results are shown in Table 6.
  • the photopic odor can be reduced when the F3 amount of soybean oil is 50 ppm or less (A value is 40 ppm or less). I understood.
  • ⁇ Test Example 7> (Preparation of mixed oil, part 2) Using the soybean oils obtained in Comparative Examples 1-1 to 1-3 and Examples 1-1 to 2 in Test Example 1, the ratio shown in Table 7 was mixed with rapeseed oil (manufactured by J-Oil Mills Co., Ltd.). . About the obtained mixed oil, the photopic odor was evaluated. The results are shown in Table 7.
  • the photopic odor can be reduced when the F3 amount of soybean oil is 118 ppm or less (A value is 71 ppm or less). I understood.
  • ⁇ Test Example 8> (Preparation of mixed oil, part 3) Using the soybean oil obtained in Comparative Examples 1-1 to 1-3 of Test Example 1 and Example 1-1, the oil was mixed with rapeseed oil (manufactured by J-Oil Mills Co., Ltd.) at the ratio shown in Table 8. About the obtained mixed oil, the photopic odor was evaluated. The results are shown in Table 8.
  • the photopic 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.
  • the photopic odor can be reduced when the F3 amount of soybean oil is 118 ppm or less (A value is 35 ppm or less). I understood.
  • the photopic odor can be reduced when the F3 amount of soybean oil is 118 ppm or less (A value is 24 ppm or less). I understood.

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  • General Chemical & Material Sciences (AREA)
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Abstract

La présente invention décrit : un procédé de production d'une huile de soja présentant une odeur réduite dans les endroits lumineux ; un procédé de production d'une huile mixte obtenue par mélange de ladite huile de soja ; et un procédé d'inhibition de l'odeur de l'huile de soja dans les endroits lumineux. Le procédé de production de l'huile de soja comprend une étape dans laquelle l'huile pressée obtenue à partir des fèves de soja est exposée à une lumière ultraviolette présentant une longueur d'onde de 200 à 280 nm afin de réduire la quantité (la quantité F3) de l'acide 3,4-diméthyl-5-pentyl-2-furan nonanoïque dans l'huile. Le procédé de production de l'huile de soja comprend également une étape dans laquelle de la lipoxygénase est portée au contact de l'huile obtenue par pression de fèves de soja, afin de réduire la quantité des F3 dans l'huile. Le procédé de production de l'huile mixte inclut une étape dans laquelle l'huile de soja obtenue en utilisant le procédé susmentionné est mélangée avec une autre huile comestible. Dans le procédé de réduction de l'odeur de l'huile de soja aux endroits lumineux, l'huile obtenue par pression des fèves de soja est irradiée de lumière ultraviolette présentant une longueur d'onde de 200 à 280 nm, ou est portée en contact avec de la lipoxygénase, afin de réduire la quantité des F3 dans l'huile.
PCT/JP2016/072476 2015-08-24 2016-08-01 Procédé de production d'huile de soja, procédé de production d'huile mixte, et procédé d'inhibition de l'odeur de l'huile de soja dans les endroits lumineux WO2017033674A1 (fr)

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JP2017536709A JP6714001B2 (ja) 2015-08-24 2016-08-01 大豆油の製造方法、混合油の製造方法、及び大豆油の明所臭を抑制する方法

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JP2019022467A (ja) * 2017-07-25 2019-02-14 株式会社Ｊ−オイルミルズ 油脂組成物の明所臭抑制方法
WO2019173292A1 (fr) * 2018-03-06 2019-09-12 Bunge Global Innovation, Llc Procédés de blanchiment de compositions de phospholipides
WO2022158583A1 (fr) * 2021-01-21 2022-07-28 国立大学法人佐賀大学 Soja ayant une faible teneur en acide furanique

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019022467A (ja) * 2017-07-25 2019-02-14 株式会社Ｊ−オイルミルズ 油脂組成物の明所臭抑制方法
WO2019173292A1 (fr) * 2018-03-06 2019-09-12 Bunge Global Innovation, Llc Procédés de blanchiment de compositions de phospholipides
CN111970932A (zh) * 2018-03-06 2020-11-20 邦吉全球创新有限责任公司 对磷脂组合物进行脱色的方法
US11466229B2 (en) 2018-03-06 2022-10-11 Bunge Global Innovation, Llc Methods for bleaching phospholipid compositions
WO2022158583A1 (fr) * 2021-01-21 2022-07-28 国立大学法人佐賀大学 Soja ayant une faible teneur en acide furanique

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