JP2016136909A - Method for producing edible oils and fats - Google Patents
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Abstract
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本発明は、機能性素材として近年注目されているアルキルレゾルシノールを含有する食用油脂の製造方法に関する。 The present invention relates to a method for producing edible fats and oils containing alkylresorcinol which has recently attracted attention as a functional material.
近年、健康意識の高まりから、食物繊維、ビタミン、ミネラル等の栄養素に富む小麦ふすまの需要が増してきており、それに伴い、小麦ふすまの有効利用に関する技術が種々提案されている。例えば特許文献１及び２には、食用油脂が保存中に酸化して過酸化物価（ＰＯＶ）が上昇する不都合を防止し得るＰＯＶ上昇抑制剤として、小麦ふすまの各種溶媒による抽出物を有効成分とする組成物が記載されている。特許文献１及び２には、この抽出物の抽出方法として、ｎ−ヘキサン、オリーブ油等の抽出溶媒の沸騰下で窒素気流中３０分〜５時間程度抽出する方法、あるいは、オリーブ油等の食用油脂中に小麦ふすまを浸漬し、その状態で室温から２００℃で窒素気流中数時間から１０日間程度抽出する方法が記載されている。 In recent years, the demand for wheat bran rich in nutrients such as dietary fiber, vitamins, and minerals has increased due to an increase in health consciousness, and various techniques relating to the effective use of wheat bran have been proposed accordingly. For example, Patent Documents 1 and 2 disclose, as an active ingredient, an extract of wheat bran as an active ingredient as a POV increase inhibitor that can prevent the inconvenience that edible fats and oils are oxidized during storage and the peroxide value (POV) increases. A composition is described. In Patent Documents 1 and 2, as an extraction method of this extract, a method of extracting for about 30 minutes to 5 hours in a nitrogen stream under the boiling of an extraction solvent such as n-hexane or olive oil, or in an edible fat or oil such as olive oil Describes a method in which wheat bran is soaked and extracted from room temperature to 200 ° C. in a nitrogen stream for several hours to about 10 days.
また、合成されたアルキルレゾルシノール及びその誘導体や、小麦、ライ麦等の穀類の種皮やカシューナッツ等のナッツ類の種皮から抽出されたアルキルレゾルシノール含有抽出物が、抗肥満作用、抗酸化作用、抗免疫作用等を有することが知られている。特許文献１及び２にはアルキルレゾルシノールについては記載されていない。 In addition, the synthesized alkylresorcinol and its derivatives, and the extract containing alkylresorcinol extracted from the seed coat of cereals such as wheat and rye and the seed coat of nuts such as cashew nuts have anti-obesity action, antioxidant action and anti-immunity action. Etc. are known to have. Patent Documents 1 and 2 do not describe alkylresorcinol.
本発明の課題は、アルキルレゾルシノールを効率的に吸収し得る食品素材として有用な食用油脂の製造方法に関する。 The subject of this invention is related with the manufacturing method of edible fats and oils useful as a foodstuff material which can absorb alkyl resorcinol efficiently.
本発明は、小麦ふすまと原料油脂とを混合し、その混合物を、該混合物の品温０〜４０℃で０．５〜３時間振盪又は撹拌した後に遠心分離し、その遠心分離後の上清を回収する工程を有する、食用油脂の製造方法である。 In the present invention, wheat bran and raw oil and fat are mixed, the mixture is shaken or stirred at an article temperature of 0 to 40 ° C. for 0.5 to 3 hours, and then centrifuged, and the supernatant after centrifugation is mixed. It is a manufacturing method of edible oil and fat which has the process of collect | recovering.
本発明の食用油脂の製造方法によれば、アルキルレゾルシノールを効率的に吸収し得る食品素材として有用な食用油脂が提供される。この食用油脂に含まれるアルキルレゾルシノールは、食経験が豊富な小麦ふすま由来のものであるため、この食用油脂は、安全性が高くて副作用のおそれが少なく、食品素材として安心して使用できる。 According to the method for producing edible fats and oils of the present invention, edible fats and oils useful as food materials capable of efficiently absorbing alkylresorcinol are provided. Since the alkylresorcinol contained in this edible oil and fat is derived from wheat bran with abundant food experience, this edible oil and fat is safe and less likely to cause side effects, and can be used with confidence as a food material.
本発明で用いる小麦ふすまは、小麦粒の外皮部を主体とするものである。小麦ふすまとしては、一般的な小麦粉の製造過程で生じる、小麦粒から胚乳を除去した残部、あるいはこの残部からさらに胚芽を除去したもの等を用いることができ、基本的に組成や製造過程を問わない。また、小麦ふすまの原料となる小麦の種類は特に制限されない。 The wheat bran used in the present invention is mainly composed of the outer skin of wheat grains. As wheat bran, it is possible to use a residue obtained by removing the endosperm from a wheat grain, which is produced in a general wheat flour production process, or a product obtained by further removing the germ from the remainder. Absent. Moreover, the kind of wheat used as the raw material of wheat bran is not particularly limited.
本発明で用いる原料油脂としては、一般に食品に使用される食用油脂を特に制限なく用いることができる。また、本発明で用いる原料油脂は、室温（１０〜４０℃）で液状であることが望ましいが、常温で固型でも融解して使用することは可能である。原料油脂としては例えば、大豆油、菜種油、高オレイン酸菜種油、コーン油、ゴマ油、ゴマサラダ油、太白ゴマ油、シソ油、亜麻仁油、落花生油、紅花油、高オレイン酸紅花油、ひまわり油、高オレイン酸ひまわり油、綿実油、ブドウ種子油、マカデミアナッツ油、ヘーゼルナッツ油、カボチャ種子油、クルミ油、椿油、茶実油、エゴマ油、ボラージ油、オリーブ油、米油、米糠油、小麦胚芽油、パーム油、パームオレイン、パームステアリン、パーム核油、ヤシ油、カカオ脂、牛脂、ラード、鶏脂、乳脂、魚油等が挙げられ、これらの１種を単独で又は２種以上を組み合わせて用いることができる。本発明で用いる原料油脂は、炭素数２〜４個の短鎖脂肪酸（低級脂肪酸）、炭素数５〜１２個の中鎖脂肪酸、炭素数が１２個を超える長鎖脂肪酸（高級脂肪酸）の何れであっても良く、また、これら各種脂肪酸とグリセリンとを常法によりエステル化反応に付して得られる、トリグリセリドであっても良い。脂肪酸トリグリセリドの一例として、ＭＣＴ（Medium Chain Triglycerides）とも呼ばれる中鎖脂肪酸トリグリセリドが挙げられる。ＭＣＴは、ヤシ油分解脂肪酸等の炭素数が８〜１０の飽和脂肪酸から構成される単酸基もしくは混酸基トリグリセリドであり、例えばカプリル酸／カプリン酸＝６０／４０〜７５／２５（質量比）のトリグリセリドである。本発明で用いる原料油脂として特に好ましいものは、中鎖脂肪酸トリグリセリド（ＭＣＴ）、大豆油、菜種油であり、これらは常温で液状であり且つ食用として広く使用されているため、本発明で好ましく用いられる。 As raw material fats and oils used in the present invention, edible fats and oils generally used for foods can be used without particular limitation. Moreover, although it is desirable for the raw material fats and oils used by this invention to be liquid at room temperature (10-40 degreeC), it can melt | dissolve and use even if it is a solid form at normal temperature. Examples of the raw oil and fat include soybean oil, rapeseed oil, oleic rapeseed oil, corn oil, sesame oil, sesame salad oil, white sesame oil, perilla oil, linseed oil, peanut oil, safflower oil, safflower oil, sunflower oil, high olein Acid sunflower oil, cottonseed oil, grape seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, walnut oil, straw oil, tea seed oil, sesame oil, borage oil, olive oil, rice oil, rice bran oil, wheat germ oil, palm oil, Palm olein, palm stearin, palm kernel oil, coconut oil, cacao butter, beef tallow, lard, chicken fat, milk fat, fish oil and the like can be mentioned, and these can be used alone or in combination of two or more. The raw fats and oils used in the present invention are any of short chain fatty acids having 2 to 4 carbon atoms (lower fatty acids), medium chain fatty acids having 5 to 12 carbon atoms, and long chain fatty acids having higher than 12 carbon atoms (higher fatty acids). It may also be a triglyceride obtained by subjecting these various fatty acids and glycerin to an esterification reaction by a conventional method. As an example of the fatty acid triglyceride, there is a medium chain triglyceride called MCT (Medium Chain Triglycerides). MCT is a monoacid group or mixed acid group triglyceride composed of a saturated fatty acid having 8 to 10 carbon atoms such as coconut oil-decomposed fatty acid. For example, caprylic acid / capric acid = 60/40 to 75/25 (mass ratio) Of triglycerides. Particularly preferred as raw material fats and oils for use in the present invention are medium chain fatty acid triglycerides (MCT), soybean oil, and rapeseed oil, which are liquid at room temperature and are widely used for food, and are therefore preferably used in the present invention. .
本発明の食用油脂の製造方法においては、先ず、小麦ふすまと原料油脂とを混合し、その混合物を、該混合物の品温０〜４０℃で０．５〜３時間振盪又は撹拌する。振盪・撹拌時の混合物の品温が０℃未満又は振盪・撹拌時間が０．５時間未満では、アルキルレゾルシノールを効率良く抽出することができず、該混合物の品温が４０℃を超える又は振盪・撹拌時間が３時間を超えると、油脂の酸化に起因する過酸化物価（ＰＯＶ）が上昇し、食用油脂の変色、異臭等の不都合を招くおそれがある。振盪・撹拌時の混合物の品温は好ましくは１５〜２５℃、振盪時間は好ましくは０．５〜１時間である。尚、振盪及び撹拌の両方を実施しても良く、その場合、実施順序は特に制限されず、また、両操作の合計実施時間が０．５〜３時間となるようにする。 In the method for producing edible fats and oils of the present invention, first, wheat bran and raw oils and fats are mixed, and the mixture is shaken or stirred at an article temperature of 0 to 40 ° C. for 0.5 to 3 hours. When the product temperature of the mixture at the time of shaking / stirring is less than 0 ° C. or the time of shaking / stirring is less than 0.5 hour, alkylresorcinol cannot be efficiently extracted, and the product temperature of the mixture exceeds 40 ° C. or shakes. -When stirring time exceeds 3 hours, the peroxide value (POV) resulting from the oxidation of fats and oils will rise, and there exists a possibility of causing inconveniences, such as discoloration of edible fats and oils, and a bad smell. The product temperature of the mixture during shaking and stirring is preferably 15 to 25 ° C., and the shaking time is preferably 0.5 to 1 hour. In addition, you may implement both shaking and stirring, in that case, an implementation order in particular is not restrict | limited, Moreover, the total implementation time of both operation shall be 0.5 to 3 hours.
振盪は例えば、回転振盪方式、往復振盪方式、８の字振盪方式等の、公知の振盪装置を用いて実施することができる。撹拌は例えば、攪拌羽根が取り付けられた撹拌軸をモーターで回転させる方式等の、公知の撹拌装置を用いて実施することができる。振盪又は撹拌の際に使用する原料油脂の量は、特に制限されないが、小麦ふすま１００質量部に対して、好ましくは１００〜２０００質量部、さらに好ましくは３００〜１０００質量部である。 The shaking can be performed using a known shaking device such as a rotary shaking method, a reciprocating shaking method, or an 8-shaped shaking method. Stirring can be performed using a known stirring device such as a method of rotating a stirring shaft to which a stirring blade is attached by a motor. Although the quantity of the raw material fat used in the case of shaking or stirring is not restrict | limited, Preferably it is 100-2000 mass parts with respect to 100 mass parts of wheat bran, More preferably, it is 300-1000 mass parts.
小麦ふすまと原料油脂との混合物を振盪又は撹拌した後は、該混合物を遠心分離し、その遠心分離後の上清を回収する。この回収した上清が、製造目的物である食用油脂である。混合物の遠心分離は公知の遠心分離器を用いて実施することができる。遠心分離の条件に特に制限はないが、遠心分離をより確実に実施する観点から、遠心力は好ましくは１５０〜１５０００Ｇ、さらに好ましくは５００〜４０００Ｇ、遠心分離時間は好ましくは０．５〜６０分間、さらに好ましくは３〜２０分間である。 After the mixture of wheat bran and raw oil and fat is shaken or stirred, the mixture is centrifuged, and the supernatant after the centrifugation is collected. The collected supernatant is an edible oil / fat which is a production object. Centrifugation of the mixture can be carried out using a known centrifuge. Centrifugation conditions are not particularly limited, but from the viewpoint of more reliably performing the centrifugation, the centrifugal force is preferably 150 to 15000 G, more preferably 500 to 4000 G, and the centrifugation time is preferably 0.5 to 60 minutes. More preferably, it is 3 to 20 minutes.
遠心分離後の上清、即ち、本発明の製造方法の実施によって得られた食用油脂には、下記一般式（Ｉ）で表されるアルキルレゾルシノールが含有されている。下記一般式（Ｉ）で表されるアルキルレゾルシノールは、抗肥満作用、抗酸化作用、抗免疫作用等を有しており、これを含む食用油脂は機能性食材として有用である。 The supernatant after centrifugation, that is, the edible fat obtained by carrying out the production method of the present invention contains alkylresorcinol represented by the following general formula (I). Alkylresorcinol represented by the following general formula (I) has an anti-obesity action, an antioxidant action, an anti-immunity action, and the like, and edible fats and oils containing them are useful as functional foods.
前記一般式（Ｉ）におけるＲ1に関し、炭素原子数１５〜２５の飽和アルキル基としては、代表例として、ｎ−ペンタデシル、ｎ−ヘプタデシル、ｎ−ノナデシル、ｎ−ヘンイコシル、ｎ−トリコシル、ｎ−ペンタコシル、ｎ−ヘプタコシル等の直鎖状のものが挙げられ、これらの他に、分岐状又は環状のものでも良い。これらの中でも、炭素原子数１５〜２３の飽和アルキル基が好ましい。 Regarding R 1 in the general formula (I), examples of the saturated alkyl group having 15 to 25 carbon atoms include n-pentadecyl, n-heptadecyl, n-nonadecyl, n-henicosyl, n-tricosyl, n- Examples include linear ones such as pentacosyl and n-heptacosyl, and besides these, branched or cyclic ones may be used. Among these, a saturated alkyl group having 15 to 23 carbon atoms is preferable.
また、前記一般式（Ｉ）におけるＲ1に関し、炭素原子数１５〜２５の不飽和アルキル基としては、前記の炭素原子数１５〜２５の飽和アルキル基に対応するものが挙げられる。不飽和アルキル基に含まれる不飽和結合の数及び位置に特に制限はない。 Moreover, regarding R 1 in the general formula (I), examples of the unsaturated alkyl group having 15 to 25 carbon atoms include those corresponding to the saturated alkyl group having 15 to 25 carbon atoms. There is no restriction | limiting in particular in the number and position of the unsaturated bond contained in an unsaturated alkyl group.
また、前記一般式（Ｉ）におけるＲ2は水素原子であることが好ましく、また、Ｒ1はＲ2に対してパラ位に結合していることが好ましい。 In the general formula (I), R 2 is preferably a hydrogen atom, and R 1 is preferably bonded to R 2 at the para position.
前記一般式（Ｉ）で表されるアルキルレゾルシノールの具体例としては、以下のものが挙げられる。
１，３−ジヒドロキシ−５−ｎ−ペンタデシルベンゼン（Ｃ１５：０）
１，３−ジヒドロキシ−５−ｎ−ヘプタデシルベンゼン（Ｃ１７：０）
１，３−ジヒドロキシ−５−ｎ−ノナデシルベンゼン（Ｃ１９：０）
１，３−ジヒドロキシ−５−ｎ−ヘンイコシルベンゼン（Ｃ２１：０）
１，３−ジヒドロキシ−５−ｎ−トリコシルベンゼン（Ｃ２３：０）
１，３−ジヒドロキシ−５−ｎ−ペンタコシルベンゼン（Ｃ２５：０）
Specific examples of the alkylresorcinol represented by the general formula (I) include the following.
1,3-dihydroxy-5-n-pentadecylbenzene (C15: 0)
1,3-dihydroxy-5-n-heptadecylbenzene (C17: 0)
1,3-dihydroxy-5-n-nonadecylbenzene (C19: 0)
1,3-dihydroxy-5-n-henicosylbenzene (C21: 0)
1,3-dihydroxy-5-n-tricosylbenzene (C23: 0)
1,3-dihydroxy-5-n-pentacosylbenzene (C25: 0)
前記一般式（Ｉ）で表されるアルキルレゾルシノールの好ましい一例として、下記６種類のアルキルレゾルシノールを含有するものが挙げられる。
１）前記一般式（Ｉ）におけるＲ1が炭素原子数１５の飽和又は不飽和のアルキル基であるアルキルレゾルシノール（以下、ＡＲ１５ともいう）。
２）前記一般式（Ｉ）におけるＲ1が炭素原子数１７の飽和又は不飽和のアルキル基であるアルキルレゾルシノール（以下、ＡＲ１７ともいう）。
３）前記一般式（Ｉ）におけるＲ1が炭素原子数１９の飽和又は不飽和のアルキル基であるアルキルレゾルシノール（以下、ＡＲ１９ともいう）。
４）前記一般式（Ｉ）におけるＲ1が炭素原子数２１の飽和又は不飽和のアルキル基であるアルキルレゾルシノール（以下、ＡＲ２１ともいう）。
５）前記一般式（Ｉ）におけるＲ1が炭素原子数２３の飽和又は不飽和のアルキル基であるアルキルレゾルシノール（以下、ＡＲ２３ともいう）。
６）前記一般式（Ｉ）におけるＲ1が炭素原子数２５の飽和又は不飽和のアルキル基であるアルキルレゾルシノール（以下、ＡＲ２５ともいう）。
Preferred examples of the alkylresorcinol represented by the general formula (I) include those containing the following six types of alkylresorcinol.
1) Alkyl resorcinol (hereinafter, also referred to as AR15) in which R 1 in the general formula (I) is a saturated or unsaturated alkyl group having 15 carbon atoms.
2) Alkyl resorcinol (hereinafter, also referred to as AR17) in which R 1 in the general formula (I) is a saturated or unsaturated alkyl group having 17 carbon atoms.
3) Alkyl resorcinol (hereinafter, also referred to as AR19) in which R 1 in the general formula (I) is a saturated or unsaturated alkyl group having 19 carbon atoms.
4) Alkyl resorcinol (hereinafter, also referred to as AR21) in which R 1 in the general formula (I) is a saturated or unsaturated alkyl group having 21 carbon atoms.
5) Alkyl resorcinol (hereinafter also referred to as AR23) in which R 1 in the general formula (I) is a saturated or unsaturated alkyl group having 23 carbon atoms.
6) Alkyl resorcinol (hereinafter also referred to as AR25) in which R 1 in the general formula (I) is a saturated or unsaturated alkyl group having 25 carbon atoms.
ＡＲ１５として特に好ましいものは、Ｒ1が炭素原子数１５の飽和アルキル基、Ｒ2が水素原子であるものであり、具体的には、１，３−ジヒドロキシ−５−ｎ−ペンタデシルベンゼン（Ｃ１５：０）が挙げられる。
ＡＲ１７として特に好ましいものは、Ｒ1が炭素原子数１７の飽和アルキル基、Ｒ2が水素原子であるものであり、具体的には、１，３−ジヒドロキシ−５−ｎ−ヘプタデシルベンゼン（Ｃ１７：０）が挙げられる。
ＡＲ１９として特に好ましいものは、Ｒ1が炭素原子数１９の飽和アルキル基、Ｒ2が水素原子であるものであり、具体的には、１，３−ジヒドロキシ−５−ｎ−ノナデシルベンゼン（Ｃ１９：０）が挙げられる。
ＡＲ２１として特に好ましいものは、Ｒ1が炭素原子数２１の飽和アルキル基、Ｒ2が水素原子であるものであり、具体的には、１，３−ジヒドロキシ−５−ｎ−ヘンイコシルベンゼン（Ｃ２１：０）が挙げられる。
ＡＲ２３として特に好ましいものは、Ｒ1が炭素原子数２３の飽和アルキル基、Ｒ2が水素原子であるものであり、具体的には、１，３−ジヒドロキシ−５−ｎ−トリコシルベンゼン（Ｃ２３：０）が挙げられる。
ＡＲ２５として特に好ましいものは、Ｒ1が炭素原子数２５飽和アルキル基、Ｒ2が水素原子であるものであり、具体的には、１，３−ジヒドロキシ−５−ｎ−ペンタコシルベンゼン（Ｃ２５：０）が挙げられる。
Particularly preferred as AR15 is one in which R 1 is a saturated alkyl group having 15 carbon atoms and R 2 is a hydrogen atom. Specifically, 1,3-dihydroxy-5-n-pentadecylbenzene (C15 : 0).
Particularly preferred as AR17 is one in which R 1 is a saturated alkyl group having 17 carbon atoms and R 2 is a hydrogen atom. Specifically, 1,3-dihydroxy-5-n-heptadecylbenzene (C17 : 0).
Particularly preferred as AR19 is one in which R 1 is a saturated alkyl group having 19 carbon atoms and R 2 is a hydrogen atom. Specifically, 1,3-dihydroxy-5-n-nonadecylbenzene (C19 : 0).
Particularly preferred as AR21 is one in which R 1 is a saturated alkyl group having 21 carbon atoms and R 2 is a hydrogen atom. Specifically, 1,3-dihydroxy-5-n-henecosylbenzene ( C21: 0).
Particularly preferred as AR23 is one in which R 1 is a saturated alkyl group having 23 carbon atoms and R 2 is a hydrogen atom. Specifically, 1,3-dihydroxy-5-n-tricosylbenzene (C23 : 0).
Particularly preferred as AR25 is one in which R 1 is a saturated alkyl group having 25 carbon atoms and R 2 is a hydrogen atom. Specifically, 1,3-dihydroxy-5-n-pentacosylbenzene (C25 : 0).
本発明の製造方法の実施によって得られた食用油脂、即ち前記混合物の遠心分離後の上清には、前記一般式（Ｉ）で表されるアルキルレゾルシノールが高含有されている。この上清中におけるこの特定アルキルレゾルシノールの含有量は、抽出に用いる原料油脂の種類等にもよるが、通常７０ｐｐｍ以上である。従って、本発明の製造方法の実施によって得られた食用油脂は、この特定アルキルレゾルシノールを効率的に吸収し得る食品素材として有用である。本発明の製造方法の実施によって得られた食用油脂は、幅広い食品用途に用いることができ、例えば、フライ食品、クリーム、ドレッシング、パン、ケーキ、菓子類等に好適である。 The edible oil and fat obtained by carrying out the production method of the present invention, that is, the supernatant after centrifugation of the mixture, contains a high content of alkylresorcinol represented by the general formula (I). The content of the specific alkyl resorcinol in the supernatant is usually 70 ppm or more, although it depends on the type of raw material fat used for extraction. Therefore, the edible fat obtained by carrying out the production method of the present invention is useful as a food material capable of efficiently absorbing this specific alkylresorcinol. Edible fats and oils obtained by carrying out the production method of the present invention can be used for a wide range of food applications, and are suitable for, for example, fried foods, creams, dressings, breads, cakes, confectionery, and the like.
以下、実施例を挙げて、本発明を更に詳細に説明するが、本発明は実施例により制限されるものではない。 EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further in detail, this invention is not restrict | limited by an Example.
〔実施例１〜６、比較例１〜１２及び参考例１〜６〕
容量５０ｍｌのガラス管に小麦ふすま（商品名：ウィートブランＭ、日清製粉株式会社製）を秤量し、さらに該ガラス管に該小麦ふすまの質量の５倍量の抽出溶媒を添加して混合物を調製した。抽出溶媒として、ＭＣＴ（ココナードＭＴ、花王株式会社製）、大豆油若しくは菜種油（以上、原料油脂）又はエタノールを用いた。そして、品温２２±５℃の混合物が入ったガラス管を、万能シェーカー（ＡＳ−１Ｎ、アズワン株式会社製）を用いて、室温２２±５℃の環境下で上下方向又は水平方向に２１８回（往復回数）／分の速度で所定時間振盪させた後、遠心分離器（Allegra X-30R centrifuge、Beckman coulter製）を用いて１２００Ｇで１０分間遠心分離し、その遠心分離後の上清を回収した。
[Examples 1-6, Comparative Examples 1-12 and Reference Examples 1-6]
A wheat bran (trade name: Wheat Blanc M, manufactured by Nisshin Flour Milling Co., Ltd.) is weighed into a glass tube with a capacity of 50 ml, and an extraction solvent having an amount 5 times the mass of the wheat bran is added to the glass tube to obtain a mixture. Prepared. As the extraction solvent, MCT (Coconard MT, manufactured by Kao Corporation), soybean oil or rapeseed oil (above, raw oil and fat) or ethanol was used. Then, the glass tube containing the mixture having a product temperature of 22 ± 5 ° C. is used 218 times in the vertical direction or the horizontal direction in a room temperature of 22 ± 5 ° C. using a universal shaker (AS-1N, manufactured by AS ONE Corporation). After shaking for a predetermined time at a speed of (number of reciprocations) / min, centrifuge at 1200 G for 10 minutes using a centrifuge (Allegra X-30R centrifuge, manufactured by Beckman coulter), and collect the supernatant after the centrifugation did.
〔評価試験〕
前記各実施例、比較例及び参考例の遠心分離後の上清（食用油脂）について、下記方法によりアルキルレゾルシノール濃度を測定すると共に、基準油脂分析試験法（酢酸-イソオクタン法）に準じて過酸化物価（ＰＯＶ）を測定した。それらの結果を下記表１に示す。
〔Evaluation test〕
For the supernatants (edible fats and oils) after centrifugation of the above Examples, Comparative Examples and Reference Examples, the alkylresorcinol concentration was measured by the following method and peroxidized according to the standard fat analysis method (acetic acid-isooctane method) The price (POV) was measured. The results are shown in Table 1 below.
＜アルキルレゾルシノール含有量の測定方法＞
比色法により食用油脂中のアルキルレゾルシノール濃度を測定した。標準物質として、アルキル基（前記一般式（Ｉ）におけるＲ1）の炭素原子数が２１である5-n-heneicosylresorcinolを用いた。小麦には複数種のアルキルレゾルシノールが含まれているが、その中でもアルキル基の炭素原子数が２１のものが最も含有量が多いとされている。また、Fast Blue B salt（Sigma Aldrich,D-9805, Dye content 〜95％）を１％酢酸で 溶解して０．０５％溶液を調製し、これをメタノールで６倍希釈したものをFast Blue B working solutionとした。
メタノールで濃度１ｍｇ／１ｍＬに調製した標準物質を試験管に１〜１０μｌ採取し、さらにその試験管にFast Blue B working Solutionを２ｍＬ加えてVortexでよく撹拌した後、暗所で１時間放置した。その後、波長５２０ｎｍで試験管の内容物の吸光度を測定して検量線を作成した。
そして、測定対象物（食用油脂）を試験管に１０μｌ採取し、さらにその試験管にFast Blue B working Solutionを２ｍＬ加えてVortexでよく撹拌した後、暗所で１時間放置した。その後、波長５２０ｎｍで試験管の内容物の吸光度を測定し、その測定値に基づき前記検量線を用いて、測定対象物中のアルキルレゾルシノール濃度を算出した。
<Measurement method of alkylresorcinol content>
The alkyl resorcinol concentration in edible fats and oils was measured by a colorimetric method. As a standard substance, 5-n-heneicosylresorcinol in which the alkyl group (R 1 in the general formula (I)) has 21 carbon atoms was used. Wheat contains a plurality of types of alkylresorcinol. Among them, those having 21 carbon atoms in the alkyl group are said to have the highest content. Also, Fast Blue B salt (Sigma Aldrich, D-9805, Dye content ~ 95%) was dissolved in 1% acetic acid to prepare a 0.05% solution, which was diluted 6-fold with methanol to produce Fast Blue B salt. Working solution.
1 to 10 μl of a standard substance adjusted to a concentration of 1 mg / 1 mL with methanol was collected in a test tube, 2 mL of Fast Blue B working Solution was added to the test tube, and the mixture was stirred well with Vortex, and then left in the dark for 1 hour. Thereafter, the absorbance of the contents of the test tube was measured at a wavelength of 520 nm to prepare a calibration curve.
Then, 10 μl of the measurement object (edible oil / fat) was collected in a test tube, and 2 mL of Fast Blue B working Solution was further added to the test tube and stirred well with Vortex, and then left in the dark for 1 hour. Thereafter, the absorbance of the contents of the test tube was measured at a wavelength of 520 nm, and the concentration of alkylresorcinol in the measurement object was calculated using the calibration curve based on the measured value.
表１に示す通り、実施例１〜６の製造方法によれば、アルキルレゾルシノール濃度の高い食用油脂が得られる。比較例２の製造方法は、アルキルレゾルシノール濃度の高い食用油脂が得られるものの、該食用油脂はＰＯＶ濃度も高いため、好ましくない。即ち、ＭＣＴを抽出溶媒（原料油脂）として用いた場合、振盪時間を１５時間とするのは、ＰＯＶ濃度が高くなるため好ましくない。表１に示す結果から、アルキルレゾルシノール濃度が高く且つＰＯＶ濃度が低い食用油脂を得るためには、小麦ふすまと原料油脂との混合物を室温下で０．５〜３時間程度振盪させるのが良いことがわかる。 As shown in Table 1, according to the production methods of Examples 1 to 6, edible fats and oils having a high alkylresorcinol concentration can be obtained. The production method of Comparative Example 2 is not preferable because an edible oil / fat having a high alkylresorcinol concentration is obtained, but the edible oil / fat also has a high POV concentration. That is, when MCT is used as the extraction solvent (raw material fat), it is not preferable to set the shaking time to 15 hours because the POV concentration becomes high. From the results shown in Table 1, in order to obtain an edible oil / fat having a high alkylresorcinol concentration and a low POV concentration, the mixture of wheat bran and raw oil / fat should be shaken at room temperature for about 0.5 to 3 hours. I understand.
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