JP2016086690A - Flavor oil - Google Patents
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Description
本発明は、液状油と香味材を含む香味油に関する。 The present invention relates to a flavor oil containing a liquid oil and a flavor material.
香味油は香辛料やハーブなどの香味材を含む油脂からなるもので、塗布、噴霧、あるいは浸漬などして畜肉、水産物をコーティングし、香りの良い味付けを施すことができる。また、水分を多く含む調味料とは違い、ソテーする際のソースとして用いても焦げ付きにくく、油ハネが起こらずにしっとりと焼き上げることができるのが利点である。さらには冷蔵、冷凍流通時の食品の乾燥や鮮度低下を抑えることにも用いられている。 Flavored oils are made from fats and oils containing flavoring materials such as spices and herbs, and can be applied, sprayed, or dipped to coat livestock meat and marine products to give a fragrant flavor. Moreover, unlike seasonings containing a lot of moisture, it is advantageous that it can be burnt moistly without causing oil splashing even when used as a sauce for sauteing. Furthermore, it is also used to suppress food drying and freshness decline during refrigeration and frozen distribution.
香味油を食品にコーティングする場合、食品から流れ落ちないようにするために適度な粘度が必要である。例えば、液状油に対してエステル交換、水素添加などを行うことで、ラード、牛脂、バターのような半固体もしくは固体にすることができる。しかし、上記の方法で改質された油脂は、液状成分が染み出すことや健康に悪影響を与えるとされるトランス型の不飽和脂肪酸が増加すること、融点の上昇による口どけの悪化という問題を抱えている。また、香味油に用いた場合には食品に対する付着性が低く、冷蔵保存時には油脂表面の光沢が損なわれるという問題がある。 When a flavor oil is coated on a food, an appropriate viscosity is required so that it does not run off from the food. For example, transesterification, hydrogenation, and the like can be performed on a liquid oil to obtain a semi-solid or solid such as lard, beef tallow, and butter. However, the fats and oils modified by the above method have problems such as exudation of liquid components, increase of trans-type unsaturated fatty acids, which are said to have an adverse effect on health, and deterioration of mouthfeel due to an increase in melting point. I have it. In addition, when used as a flavor oil, there is a problem that the adhesion to food is low, and the gloss of the oil and fat surface is impaired during refrigerated storage.
また、油脂用の増粘固化剤を用いる方法もあり、例えば特許文献１には炭素数２０以上の脂肪酸のエステルと、ＨＬＢ３以下のポリグリセリン脂肪酸エステル及びＨＬＢ３以下のショ糖脂肪酸エステルからなる群より選ばれた少なくとも一種とを含有してなる油脂固化剤が開示されている。他方で、特許文献２にはベヘン酸を主要構成脂肪酸とし、エステル化度が５０％以上のポリグリセリン脂肪酸エステルを成分とする油脂用増粘剤が開示されている。また、特許文献３には炭素数２０以上の飽和脂肪酸のエステル化合物を用いた香味油ゾル状またはゲル状組成物が開示されている。 There is also a method using a thickening and solidifying agent for fats and oils. For example, Patent Document 1 includes a fatty acid ester having 20 or more carbon atoms, a polyglycerin fatty acid ester having an HLB of 3 or less, and a sucrose fatty acid ester having an HLB of 3 or less. An oil solidifying agent containing at least one selected one is disclosed. On the other hand, Patent Document 2 discloses a thickener for fats and oils containing behenic acid as a main constituent fatty acid and a polyglycerol fatty acid ester having a degree of esterification of 50% or more as a component. Patent Document 3 discloses a flavor oil sol or gel composition using an ester compound of a saturated fatty acid having 20 or more carbon atoms.
特許文献１に記載されている油脂固化剤は油脂の固化や硬さの調整を目的に用いられているものの、上記の固化剤を添加した油脂では食品に対する付着性が低く、冷蔵保存時には油脂表面の光沢も損なわれる。特許文献２に記載されている油脂増粘剤は固体脂と液状油からなる調合油の増粘技術であり、液状油のみでは食品にコーティングできる粘度が得られない。また、特許文献３は油脂の香味を保持するために増粘させる技術であって、この増粘剤では固体成分の分散や食品にコーティングできる粘度は得られない。 Although the fat and oil solidifying agent described in Patent Document 1 is used for the purpose of solidifying oil and adjusting the hardness, the oil and fat added with the above solidifying agent has low adhesion to food, and the surface of the fat and oil during refrigerated storage The gloss of is also impaired. The fat and oil thickener described in Patent Document 2 is a technique for thickening a blended oil composed of solid fat and liquid oil, and the liquid oil alone cannot provide a viscosity that can be coated on food. Moreover, patent document 3 is a technique to thicken in order to maintain the flavor of fats and oils, and with this thickener, it is not possible to obtain a dispersion of solid components or a viscosity that can be coated on food.
本発明は、上記事情に鑑み、食品に対する付着性を有し、冷蔵保存時も表面の光沢が保持される香味油を提供することを目的とするものである。 In view of the above circumstances, an object of the present invention is to provide a flavor oil that has adhesiveness to food and retains the gloss of the surface even during refrigerated storage.
本発明者が鋭意研究を重ねた結果、液状油に対し、ポリグリセリンと特定の脂肪酸から構成されるポリグリセリン脂肪酸エステルを配合することで、上記課題が達成されることを見出し、本発明を完成するに至った。 As a result of intensive studies by the inventor, the present inventors have found that the above problems can be achieved by blending a liquid oil with a polyglycerol fatty acid ester composed of polyglycerol and a specific fatty acid, thereby completing the present invention. It came to do.
即ち、本発明は、液状油と香味材とポリグリセリン脂肪酸エステルを含む香味油であって、前記ポリグリセリン脂肪酸エステルを構成する脂肪酸が（Ａ）炭素数が１６〜２２の飽和脂肪酸から選択される一種または二種以上と、（Ｂ）炭素数が８〜１４の飽和脂肪酸および炭素数が１６〜２２の不飽和脂肪酸から選択される一種または二種以上とを有し、前記構成脂肪酸ＡおよびＢの総モル量において、前記構成脂肪酸Ａのモル比率が０．３〜０．９、前記構成脂肪酸Ｂのモル比率が０．１〜０．７であることを特徴とする香味油である。 That is, this invention is a flavor oil containing liquid oil, a flavor material, and polyglycerin fatty acid ester, Comprising: The fatty acid which comprises the said polyglycerin fatty acid ester is selected from (A) C16-C22 saturated fatty acid. 1 type, or 2 or more types, and (B) 1 type, or 2 or more types selected from a saturated fatty acid having 8 to 14 carbon atoms and an unsaturated fatty acid having 16 to 22 carbon atoms, and the constituent fatty acids A and B The molar ratio of the constituent fatty acid A is 0.3 to 0.9, and the molar ratio of the constituent fatty acid B is 0.1 to 0.7.
本発明によれば、液状油に対し前記ポリグリセリン脂肪酸エステルを用いることで、食品に対する付着性を有し、冷蔵保存時も表面の光沢が保持される香味油を提供できる。 According to the present invention, by using the polyglycerin fatty acid ester for liquid oil, it is possible to provide a flavor oil that has adhesiveness to foods and retains the gloss of the surface even during refrigerated storage.
以下に本発明を詳細に説明する。
本発明の対象となる液状油は、限定されるものではないが、大豆油、ナタネ油、コーン油、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、綿実油、ぶどう種子油、マカデミアナッツ油、ヘーゼルナッツ油、かぼちゃ種子油、クルミ油、椿油、茶実油、エゴマ油、オリーブ油、カラシ油、米油、米糠油、小麦麦芽油、サフラワー油、ひまわり油およびこれらの分別油脂が例示される。また、ジグリセライドおよび／またはモノグリセライドが含有または調合されているものであっても良い。また、油脂にはステロールやステロールエステル等が任意に含有されていても良い。
The present invention is described in detail below.
Liquid oils subject to the present invention are not limited, but soybean oil, rapeseed oil, corn oil, sesame oil, perilla oil, linseed oil, peanut oil, safflower oil, safflower oil with high oleic acid, cottonseed oil, grape Seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, walnut oil, coconut oil, tea seed oil, egoma oil, olive oil, mustard oil, rice oil, rice bran oil, wheat germ oil, safflower oil, sunflower oil and fractionation thereof Oils and fats are exemplified. Further, diglyceride and / or monoglyceride may be contained or formulated. Moreover, sterol, sterol ester, etc. may contain arbitrarily in fats and oils.
本発明で使用されるポリグリセリン脂肪酸エステルは、所定の脂肪酸を構成脂肪酸としたものとなっている。ポリグリセリン脂肪酸エステルを構成する脂肪酸は、（Ａ）炭素数が１６〜２２の飽和脂肪酸から選択される一種または二種以上、（Ｂ）炭素数が８〜１４の飽和脂肪酸および炭素数が１６〜２２の不飽和脂肪酸から選択される一種または二種以上とを有している。また、好ましくは（Ａ）炭素数が１６〜２２の飽和脂肪酸から選択される二種以上、（Ｂ）炭素数１４の飽和脂肪酸および炭素数が１６〜２２の不飽和脂肪酸から選択される一種または二種以上とを有している。 The polyglycerol fatty acid ester used in the present invention has a predetermined fatty acid as a constituent fatty acid. The fatty acid constituting the polyglycerin fatty acid ester is (A) one or more selected from saturated fatty acids having 16 to 22 carbon atoms, and (B) saturated fatty acids having 8 to 14 carbon atoms and 16 to 16 carbon atoms. One or two or more selected from 22 unsaturated fatty acids. Preferably, (A) two or more kinds selected from saturated fatty acids having 16 to 22 carbon atoms, (B) one kind selected from saturated fatty acids having 14 carbon atoms and unsaturated fatty acids having 16 to 22 carbon atoms, or Have two or more.
炭素数が１６〜２２の飽和脂肪酸、炭素数が８〜１４の飽和脂肪酸、および炭素数が１６〜２２の不飽和脂肪酸は、この炭素数および飽和または不飽和の条件に当てはまるものであれば、特に限定されるものではないが、主として直鎖脂肪酸が選択される。炭素数が１６〜２２の飽和脂肪酸には、パルミチン酸、ステアリン酸、アラキン酸、ベヘン酸等が、炭素数が８〜１４の飽和脂肪酸には、カプリル酸、カプリン酸、ラウリン酸、ミリスチン酸が、炭素数１６〜２２の不飽和脂肪酸には、パルミトレイン酸、オレイン酸、エライジン酸、リノール酸、リノレン酸、アラキドン酸、エイコサペンタエン酸、エルカ酸、ドコサヘキサエン酸が例示される。 If the saturated fatty acid having 16 to 22 carbon atoms, the saturated fatty acid having 8 to 14 carbon atoms, and the unsaturated fatty acid having 16 to 22 carbon atoms are applicable to the conditions of the carbon number and saturated or unsaturated, Although not particularly limited, linear fatty acids are mainly selected. Saturated fatty acids having 16 to 22 carbon atoms include palmitic acid, stearic acid, arachidic acid, and behenic acid, and saturated fatty acids having 8 to 14 carbon atoms include caprylic acid, capric acid, lauric acid, and myristic acid. Examples of the unsaturated fatty acid having 16 to 22 carbon atoms include palmitoleic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, erucic acid, and docosahexaenoic acid.
本発明の構成脂肪酸のモル比率は、前記構成脂肪酸ＡおよびＢの総モル量において、Ａが０．３〜０．９、Ｂが０．１〜０．７となる必要がある。特に、Ａのモル比率が０．７〜０．９、Ｂのモル比率が０．１〜０．３であることが好ましい。 The molar ratio of the constituent fatty acids of the present invention is such that A is 0.3 to 0.9 and B is 0.1 to 0.7 in the total molar amount of the constituent fatty acids A and B. In particular, the molar ratio of A is preferably 0.7 to 0.9, and the molar ratio of B is preferably 0.1 to 0.3.
ポリグリセリン脂肪酸エステルを構成するポリグリセリンは、その平均重合度が限定されるものではないが、２〜２０が好ましく、４〜１０がより好ましい。ここで、平均重合度は、末端基分析法による水酸基価から算出されるポリグリセリンの平均重合度（ｎ）である。詳しくは、次式
（式１）および（式２）から平均重合度が算出される。
（式１）分子量＝７４ｎ＋１８
（式２）水酸基価＝５６１１０（ｎ＋２）／分子量
上記（式２）中の水酸基価とは、ポリグリセリンに含まれる水酸基数の大小の指標となる数値であり、１ｇのポリグリセリンに含まれる遊離ヒドロキシル基をアセチル化するために必要な酢酸を中和するのに要する水酸化カリウムのミリグラム数をいう。水酸化カリウムのミリグラム数は、社団法人日本油化学会編纂「日本油化学会制定、基準油脂分析試験法（Ｉ）、２００３年度版」に準じて算出される。
The average degree of polymerization of the polyglycerol constituting the polyglycerol fatty acid ester is not limited, but is preferably 2 to 20, and more preferably 4 to 10. Here, the average degree of polymerization is the average degree of polymerization (n) of polyglycerin calculated from the hydroxyl value by end group analysis. Specifically, the average degree of polymerization is calculated from the following formulas (Formula 1) and (Formula 2).
(Formula 1) Molecular weight = 74n + 18
(Formula 2) Hydroxyl value = 56110 (n + 2) / Molecular weight The hydroxyl value in the above (Formula 2) is a numerical value that serves as an index of the number of hydroxyl groups contained in polyglycerin, and is contained in 1 g of polyglycerin. The number of milligrams of potassium hydroxide required to neutralize the acetic acid required to acetylate the hydroxyl group. The number of milligrams of potassium hydroxide is calculated according to Japan Oil Chemists 'Society edited by “The Japan Oil Chemists' Society, Standard Oil Analysis Test Method (I), 2003 edition”.
ポリグリセリン脂肪酸エステルは、公知のエステル化反応により製造することができる。例えば、脂肪酸とポリグリセリンとを水酸化ナトリウム等のアルカリ触媒の存在下におけるエステル化反応により製造することができる。エステル化は、ポリグリセリン脂肪酸エステルのエステル化率が好ましくは６０％以上、より好ましくは８５％以上、さらに好ましくは９５％以上になるまで行われる。ここでエステル化率は、水酸基価から算出されるポリグリセリンの平均重合度（ｎ）、このポリグリセリンが有する水酸基数（ｎ＋２）、ポリグリセリンに付加している脂肪酸のモル数（Ｍ）としたとき、（Ｍ／（ｎ＋２））×１００＝エステル化率（％）で算出される値である。ここで水酸基価とは、上述の水酸基価と同様に算出される値である。 The polyglycerol fatty acid ester can be produced by a known esterification reaction. For example, a fatty acid and polyglycerin can be produced by an esterification reaction in the presence of an alkali catalyst such as sodium hydroxide. The esterification is performed until the esterification rate of the polyglycerol fatty acid ester is preferably 60% or more, more preferably 85% or more, and further preferably 95% or more. Here, the esterification rate is defined as the average degree of polymerization of polyglycerol (n) calculated from the hydroxyl value, the number of hydroxyl groups (n + 2) of the polyglycerol, and the number of moles of fatty acid added to the polyglycerol (M). In this case, (M / (n + 2)) × 100 = value calculated by esterification rate (%). Here, the hydroxyl value is a value calculated in the same manner as the hydroxyl value described above.
ポリグリセリン脂肪酸エステルを香味油に添加して含有させる量は、香味油の総重量におけるポリグリセリン脂肪酸エステルの重量濃度が０．３〜１０．０重量％、好ましくは１．５〜５．０重量％となる量であると良い。０．３重量％未満であると付着性が悪く食品から香味油が流れ落ち、１０．０重量％より多いと香味油としての風味を損なう可能性がある。また、上記配合を満たしている限り、他の食品添加物（例えば、その他のグリセリン脂肪酸エステル、ショ糖脂肪酸エステル、ソルビタン脂肪酸エステル、プロピレングリコール脂肪酸エステル、レシチン等）と併用しても構わない。 The amount of the polyglycerin fatty acid ester added to the flavor oil is 0.3 to 10.0% by weight, preferably 1.5 to 5.0% by weight, based on the total weight of the flavor oil. It is good that the amount is%. If it is less than 0.3% by weight, the adherence is poor and the flavor oil flows down from the food, and if it is more than 10.0% by weight, the flavor of the flavor oil may be impaired. Moreover, as long as the said mixing | blending is satisfy | filled, you may use together with another food additive (For example, other glycerol fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, a lecithin, etc.).
本発明における香味油に含まれる香味材としては、例えば、タマネギ、ネギ、ニンニク、ショウガ、ニラ、トウガラシ、トマト等の野菜類、ローズマリー、タイム、ローレル、バジル、オレガノ、タラゴン、ディル、フェンネル、サボリー、チャービル、ミント、レモングラス、マジョラム、アニス、オールスパイス、カホクザンショウ、カルダモン、クミン、グリーンペッパー、クローブ、コショウ、コリアンダー、サフラン、サンショウ、シソ、シナモン、スターアニス、セージ、ターメリック、タラゴン、ナツメグ、バニラ、パプリカ、フェンネル、ホースラディッシュ、ラディッシュ、ワサビ、マスタード、チンピなどのハーブ・香辛料類、しょうゆ、みそ、カレー、鰹節、鯖節といった調味料類加工食品類等が挙げられ、適宜使用することができる。 Examples of the flavoring material contained in the flavor oil in the present invention include, for example, vegetables such as onion, leek, garlic, ginger, leek, pepper, tomato, rosemary, thyme, laurel, basil, oregano, tarragon, dill, fennel, Savory, Chervil, Mint, Lemongrass, Marjoram, Anise, Allspice, Kahokuzansho, Cardamom, Cumin, Green Pepper, Clove, Pepper, Coriander, Saffron, Salamander, Perilla, Cinnamon, Star Anise, Sage, Turmeric, Tarragon , Nutmeg, vanilla, paprika, fennel, horseradish, radish, wasabi, mustard, chimpi and other herbs and spices, soy sauce, miso, curry, bonito, and bonito seasoning processed foods, etc. Rukoto can.
以下、本発明を実施例に基づき詳細に説明するが、本発明の範囲はこの実施例に限定されるものではなく、本発明の趣旨を損なわない範囲で、変更等が加えられた形態も本発明に属する。 Hereinafter, the present invention will be described in detail on the basis of examples. However, the scope of the present invention is not limited to these examples, and modifications and the like can be made without departing from the scope of the present invention. Belongs to the invention.
試験例で使用されたポリグリセリン脂肪酸エステルは、以下に示す方法により合成された。尚、実施例および比較例において平均重合度が１０のポリグリセリンに阪本薬品工業株式会社製「ポリグリセリン＃７５０」を、平均重合度が４のポリグリセリンに阪本薬品工業株式会社製「ポリグリセリン＃３１０」を、平均重合度が２のポリグリセリンに阪本薬品工業株式会社製「ジグリセリンＳ」を用いた。 The polyglycerol fatty acid ester used in the test examples was synthesized by the method shown below. In Examples and Comparative Examples, “polyglycerin # 750” manufactured by Sakamoto Yakuhin Kogyo Co., Ltd. was used for polyglycerin having an average degree of polymerization of 10, and “polyglycerin #” manufactured by Sakamoto Yakuhin Kogyo Co., Ltd. was used for polyglycerin having an average degree of polymerization of 4. “Diglycerin S” manufactured by Sakamoto Yakuhin Kogyo Co., Ltd. was used as polyglycerin having an average polymerization degree of 2.
＜実施例１＞
平均重合度が１０のポリグリセリン１００ｇとステアリン酸５９．８ｇ、オレイン酸５９．４ｇ、ベヘン酸３３４．２ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 1>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 59.8 g of stearic acid, 59.4 g of oleic acid, and 334.2 g of behenic acid was placed in a reaction vessel, and the mixture was alkalinized with sodium hydroxide and at 250 ° C. under a nitrogen stream. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例２＞
平均重合度が１０のポリグリセリン１００ｇとステアリン酸２３９．２ｇ、オレイン酸７９．２ｇ、ベヘン酸９５．５ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 2>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 239.2 g of stearic acid, 79.2 g of oleic acid, and 95.5 g of behenic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例３＞
平均重合度が１０のポリグリセリン１００ｇとミリスチン酸６４．０ｇ、ステアリン酸７９．７ｇ、ベヘン酸２８６．４ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 3>
A mixed fatty acid composed of 100 g of polyglycerin having an average degree of polymerization of 10 and 64.0 g of myristic acid, 79.7 g of stearic acid, and 286.4 g of behenic acid was placed in a reaction vessel, and the mixture was alkalinized with sodium hydroxide and at 250 ° C. under a nitrogen stream. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例４＞
平均重合度が１０のポリグリセリン１００ｇとミリスチン酸６４．０ｇ、パルミチン酸７１．９ｇ、ベヘン酸２８６．４ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 4>
A mixed fatty acid composed of 100 g of polyglycerin having an average degree of polymerization of 10 and 64.0 g of myristic acid, 71.9 g of palmitic acid, and 286.4 g of behenic acid was placed in a reaction vessel, and the mixture was alkalinized with sodium hydroxide and at 250 ° C. under a nitrogen stream. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例５＞
平均重合度が１０のポリグリセリン１００ｇとステアリン酸７９．７ｇ、ベヘン酸２８６．４ｇ、エルカ酸９４．９ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 5>
A mixed fatty acid composed of 100 g of polyglycerin having an average degree of polymerization of 10 and 79.7 g of stearic acid, 286.4 g of behenic acid and 94.9 g of erucic acid was placed in a reaction vessel, and the mixture was alkalinized with sodium hydroxide and at 250 ° C. under a nitrogen stream. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例６＞
平均重合度が１０のポリグリセリン１００ｇとパルミチン酸３５．９ｇ、ベヘン酸３８１．９ｇ、エルカ酸４７．５ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 6>
A mixed fatty acid composed of 100 g of polyglycerin having an average degree of polymerization of 10 and 35.9 g of palmitic acid, 381.9 g of behenic acid, and 47.5 g of erucic acid was placed in a reaction vessel, and the mixture was alkalinized with sodium hydroxide and at 250 ° C. under a nitrogen stream. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例７＞
平均重合度が１０のポリグリセリン１００ｇとステアリン酸１３６．３ｇ、オレイン酸１３５．４ｇ、ベヘン酸１６３．２ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 7>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 136.3 g of stearic acid, 135.4 g of oleic acid, and 163.2 g of behenic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例８＞
平均重合度が１０のポリグリセリン１００ｇとミリスチン酸１６０．１ｇ、ベヘン酸２３８．７ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 8>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 160.1 g of myristic acid and 238.7 g of behenic acid is placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide. An ester was obtained.
＜実施例９＞
平均重合度が１０のポリグリセリン１００ｇとカプリン酸４８．３ｇ、ステアリン酸７９．７ｇ、ベヘン酸２８６．４ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 9>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 48.3 g of capric acid, 79.7 g of stearic acid, and 286.4 g of behenic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例１０＞
平均重合度が１０のポリグリセリン１００ｇとラウリン酸７０．２ｇ、ステアリン酸９９．７ｇ、ベヘン酸２３８．７ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 10>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 70.2 g of lauric acid, 99.7 g of stearic acid, and 238.7 g of behenic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例１１＞
平均重合度が１０のポリグリセリン１００ｇとステアリン酸５２．１ｇ、オレイン酸５１．８ｇ、ベヘン酸２９１．３ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 11>
A mixed fatty acid composed of 100 g of polyglycerin having an average degree of polymerization of 10 and 52.1 g of stearic acid, 51.8 g of oleic acid, and 291.3 g of behenic acid was placed in a reaction vessel, and the mixture was alkalinized with sodium hydroxide and at 250 ° C. under a nitrogen stream. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例１２＞
平均重合度が１０のポリグリセリン１００ｇとステアリン酸３６．８ｇ、オレイン酸３６．５ｇ、ベヘン酸２０５．６ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 12>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 36.8 g of stearic acid, 36.5 g of oleic acid, and 205.6 g of behenic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例１３＞
平均重合度が４のポリグリセリン１００ｇとステアリン酸７６．８ｇ、オレイン酸７６．２ｇ、ベヘン酸４２８．９ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 13>
A mixed fatty acid composed of 100 g of polyglycerin having an average degree of polymerization of 4 and 76.8 g of stearic acid, 76.2 g of oleic acid, and 428.9 g of behenic acid was placed in a reaction vessel, and the mixture was alkalinized with sodium hydroxide and at 250 ° C. under a nitrogen stream. It was made to react and the polyglycerol fatty acid ester was obtained.
＜実施例１４＞
平均重合度が２のポリグリセリン１００ｇとステアリン酸１００．１ｇ、オレイン酸９９．４ｇ、ベヘン酸５５９．２ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Example 14>
A mixed fatty acid composed of 100 g of polyglycerin having an average degree of polymerization of 2, 100.1 g of stearic acid, 99.4 g of oleic acid, and 559.2 g of behenic acid was placed in a reaction vessel, and the mixture was alkalinized with sodium hydroxide and at 250 ° C. under a nitrogen stream. It was made to react and the polyglycerol fatty acid ester was obtained.
＜比較例１＞
平均重合度が１０のポリグリセリン１００ｇとステアリン酸３９．９ｇ、オレイン酸３１６．７ｇ、ベヘン酸４７．７ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Comparative Example 1>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 39.9 g of stearic acid, 316.7 g of oleic acid, and 47.7 g of behenic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. It was made to react and the polyglycerol fatty acid ester was obtained.
＜比較例２＞
平均重合度が１０のポリグリセリン１００ｇとラウリン酸１４．０ｇ、パルミチン酸１８．０ｇ、ベヘン酸４２９．６ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Comparative Example 2>
A mixed fatty acid composed of 100 g of polyglycerin having an average degree of polymerization of 10 and 14.0 g of lauric acid, 18.0 g of palmitic acid and 429.6 g of behenic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. It was made to react and the polyglycerol fatty acid ester was obtained.
＜比較例３＞
平均重合度が１０のポリグリセリン１００ｇとステアリン酸１９９．４ｇ、ベヘン酸２３８．７ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Comparative Example 3>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 199.4 g of stearic acid and 238.7 g of behenic acid is placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide. An ester was obtained.
＜比較例４＞
平均重合度が１０のポリグリセリン１００ｇとベヘン酸４７７．４ｇを反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Comparative example 4>
100 g of polyglycerin having an average degree of polymerization of 10 and 477.4 g of behenic acid were placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide to obtain a polyglycerin fatty acid ester.
＜比較例５＞
平均重合度が１０のポリグリセリン１００ｇとステアリン酸２７．６ｇ、オレイン酸２７．４ｇ、ベヘン酸１５４．２ｇから成る混合脂肪酸を反応容器に入れ、水酸化ナトリウムによるアルカリ性および窒素気流下、２５０℃で反応させ、ポリグリセリン脂肪酸エステルを得た。
<Comparative Example 5>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 27.6 g of stearic acid, 27.4 g of oleic acid, and 154.2 g of behenic acid is placed in a reaction vessel, and the mixture is alkalinized with sodium hydroxide and at 250 ° C. under a nitrogen stream. It was made to react and the polyglycerol fatty acid ester was obtained.
以上の実施例１〜１４、比較例１〜５のポリグリセリン脂肪酸エステルを用いて、以下に示す方法で香味油を調製した。また、食品添加物を加えずに以下の方法で調製した香味油を比較例６とした。 Using the above-described polyglycerin fatty acid esters of Examples 1 to 14 and Comparative Examples 1 to 5, flavor oils were prepared by the method shown below. Moreover, the flavor oil prepared by the following method, without adding a food additive, was made into the comparative example 6.
＜香味油の調製方法＞
表１に示す配合に従い、キャノーラ油、食塩、ローストガーリック、赤唐辛子、実施例１〜１４、比較例１〜５のポリグリセリン脂肪酸エステルをそれぞれ添加し、７０℃で均一に溶解させた後、これを撹拌しながら室温まで冷却し、香味油とした。
<Method for preparing flavor oil>
According to the formulation shown in Table 1, after adding canola oil, salt, roasted garlic, red pepper, Examples 1-14 and polyglycerin fatty acid esters of Comparative Examples 1-5 and uniformly dissolving at 70 ° C., this The mixture was cooled to room temperature with stirring to obtain a flavor oil.
調製した香味油について、試験例に基づき評価した。 The prepared flavor oil was evaluated based on test examples.
＜試験例１＞
鶏もも肉１００ｇを香味油に浸漬し、油切りをして冷蔵保存を行った。１日後の付着性を以下の基準で評価した。
＜付着性＞
◎：香味油が食品に均一に付着し、流れ落ちなかった。
○：香味油が食品に付着した際に厚さにムラが生じたものの、流れ落ちなかった。
△：香味油が食品から少し流れ落ちたが、食品の半分以上に付着していた。
×：香味油が食品から流れ落ち、ほとんど付着していなかった。
<Test Example 1>
100 g of chicken thighs were immersed in flavor oil, drained and stored refrigerated. The adhesion after 1 day was evaluated according to the following criteria.
<Adhesiveness>
(Double-circle): The flavor oil adhered to food uniformly and did not flow down.
○: When the flavor oil adhered to the food, the thickness was uneven, but did not flow down.
(Triangle | delta): Although flavor oil flowed a little from the foodstuff, it adhered to the half or more of foodstuff.
X: The flavor oil flowed down from the food and hardly adhered.
＜試験例２＞
シャーレに香味油５ｇを入れて、冷蔵保存を行なった。１日後の表面状態を以下の基準で評価した。
<Test Example 2>
Flavor oil 5g was put into a petri dish and refrigerated. The surface condition after 1 day was evaluated according to the following criteria.
＜表面状態＞
◎：表面の悪化が全く見られず、表面に光沢があった。
○：表面の一部にひび割れが見られたが、表面に光沢があった。
△：表面にひび割れや白化が見られたが、表面に光沢があった。
×：表面にひび割れや白化が見られ、表面に光沢がなかった。
付着性および表面状態の結果を表２に示した。
<Surface condition>
A: The surface was not deteriorated at all, and the surface was glossy.
○: Cracks were observed on part of the surface, but the surface was glossy.
Δ: Cracks and whitening were observed on the surface, but the surface was glossy.
X: The surface was cracked or whitened, and the surface was not glossy.
The results of adhesion and surface condition are shown in Table 2.
表２に示す通り、比較例１〜６では食品から香味油が流れ落ちる、もしくは表面の光沢が損なわれた。一方、実施例１〜１４のポリグリセリン脂肪酸エステルを添加した香味油では食品から流れ落ちず、表面の光沢が保持された。つまり、本発明の香味油のみが、コーティングの用途をなす粘度を有し、冷蔵保存時も表面の光沢が保持される香味油であることが確認できる。 As shown in Table 2, in Comparative Examples 1 to 6, the flavor oil flowed down from the food or the surface gloss was impaired. On the other hand, the flavor oil to which the polyglycerin fatty acid ester of Examples 1 to 14 was added did not flow down from the food, and the gloss of the surface was maintained. That is, it can be confirmed that only the flavor oil of the present invention is a flavor oil having a viscosity that is used as a coating and having a gloss on the surface even during refrigerated storage.
Claims (2)
前記ポリグリセリン脂肪酸エステルを構成する脂肪酸に、（Ａ）炭素数が１６〜２２の飽和脂肪酸から選択される一種または二種以上と、（Ｂ）炭素数が８〜１４の飽和脂肪酸および炭素数が１６〜２２の不飽和脂肪酸から選択される一種または二種以上とを有し、前記構成脂肪酸ＡおよびＢの総モル量において、前記構成脂肪酸Ａのモル比率が０．３〜０．９、前記構成脂肪酸Ｂのモル比率が０．１〜０．７であることを特徴とする香味油。 A flavor oil comprising a liquid oil, a flavoring material and a polyglycerin fatty acid ester,
The fatty acid constituting the polyglycerin fatty acid ester has (A) one or more selected from saturated fatty acids having 16 to 22 carbon atoms, and (B) saturated fatty acids and carbon atoms having 8 to 14 carbon atoms. 1 to 2 or more types selected from 16 to 22 unsaturated fatty acids, and in the total molar amount of the constituent fatty acids A and B, the molar ratio of the constituent fatty acids A is 0.3 to 0.9, A flavor oil, wherein the molar ratio of the constituent fatty acid B is 0.1 to 0.7.
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| JP2014222576A JP2016086690A (en) | 2014-10-31 | 2014-10-31 | Flavor oil |
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| JP2014222576A JP2016086690A (en) | 2014-10-31 | 2014-10-31 | Flavor oil |
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| WO2017199810A1 (en) * | 2016-05-19 | 2017-11-23 | 株式会社Ｊ－オイルミルズ | Method for manufacturing flavor oil, method for manufacturing flavor oil mixture, method for manufacturing flavor-enriched food, and method for flavoring fat or oil |
| JP2018042550A (en) * | 2016-09-07 | 2018-03-22 | 太陽化学株式会社 | Agent for thickening and solidifying oil-and-fat |
| JP2018057313A (en) * | 2016-10-04 | 2018-04-12 | キユーピー株式会社 | Garlic oil and method for producing the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2017199810A1 (en) * | 2016-05-19 | 2017-11-23 | 株式会社Ｊ－オイルミルズ | Method for manufacturing flavor oil, method for manufacturing flavor oil mixture, method for manufacturing flavor-enriched food, and method for flavoring fat or oil |
| JP2018042550A (en) * | 2016-09-07 | 2018-03-22 | 太陽化学株式会社 | Agent for thickening and solidifying oil-and-fat |
| JP7053186B2 (en) | 2016-09-07 | 2022-04-12 | 太陽化学株式会社 | Thickening or solidifying agent for fats and oils |
| JP2018057313A (en) * | 2016-10-04 | 2018-04-12 | キユーピー株式会社 | Garlic oil and method for producing the same |
| US20180175702A1 (en) * | 2016-12-16 | 2018-06-21 | Industrial Technology Research Institute | Motor shaft system with a cooling function |
| JP2018186724A (en) * | 2017-04-28 | 2018-11-29 | 日清オイリオグループ株式会社 | Oil and fat composition for manufacturing deep-fried food-like food, and manufacturing method therefor |
| JP2018186725A (en) * | 2017-04-28 | 2018-11-29 | 日清オイリオグループ株式会社 | Deep-fried food-like food, and manufacturing method of deep-fried food-like food |
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