JP3935676B2 - Oil and fat crystallization inhibitor - Google Patents
Oil and fat crystallization inhibitor Download PDFInfo
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- JP3935676B2 JP3935676B2 JP2001009861A JP2001009861A JP3935676B2 JP 3935676 B2 JP3935676 B2 JP 3935676B2 JP 2001009861 A JP2001009861 A JP 2001009861A JP 2001009861 A JP2001009861 A JP 2001009861A JP 3935676 B2 JP3935676 B2 JP 3935676B2
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- fatty acid
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Description
【０００１】
【発明の属する技術分野】
本発明は油脂の結晶化抑制または固化抑制効果のあるポリグリセリン脂肪酸エステルに関する。更に詳しくは、本発明の油脂の結晶化抑制剤であるポリグリセリン脂肪酸エステルを添加することで、低温保存した場合であっても常温保存時と同等の外観を保持する油脂および油脂を含有する食品に関する。
【０００２】
【従来の技術】
室温で液体である食用液体油には、大豆油、菜種油、綿実油、コーン油、ごま油等があり、家庭用または業務用として、フライ、ドレッシングなど多くの用途に使用されている。しかし、食用液体油はその多用なトリグリセリド組成のため、低温に冷却、保存した場合には高融点のトリグリセライド結晶が析出する。通常、食用液体油の製造時にはウィンタリング操作を行い、固体脂部分を分別する操作を行っているが、それでも冬場などでは僅かに含まれている固体脂が析出するために、様々な問題を引き起こす。
【０００３】
例えば、フライ油の場合においては、低温貯蔵中に結晶の析出によって全体が白濁し、商品イメージを損ねる。また、固化のために流動性を失って容器から取り出せなくなる。ドレッシング等の乳化食品の場合、冷凍や冷蔵条件下におかれると油相が結晶化することで油滴の合一を引き起こし、乳化破壊の原因となる。
【０００４】
これらの問題を解決する方法として、乳化剤を添加し油脂の結晶化を抑制する技術が知られている。例えば、ポリグリセリン脂肪酸エステルを添加する方法（特開昭６３−６３３４３号公報、特開平９−２９９０２７号公報、特開平１０−２４５５８３号公報）や、ポリグリセリン脂肪酸エステルとソルビタン脂肪酸エステルの混合物を添加する方法（特開平９−３１００８８号公報）などであるが、特に０℃以下の低温条件における液体油の耐寒性及びエマルション等の乳化食品の冷凍耐性を向上させるには効果が充分でない面があった。
【０００５】
一方、油脂の結晶化を抑制するポリグリセリン脂肪酸エステルとして、構成脂肪酸にエルカ酸を含有するものとしては、特開平９−２９９０２７号公報に炭素数１６〜２２の不飽和脂肪酸を５〜１５重量％含有するポリグリセリン脂肪酸エステルが提案されているが、これも低温雰囲気下における効果としては充分なものではなかった。また、これまで構成脂肪酸としてエルカ酸を主成分とするポリグリセリン脂肪酸エステルが油脂の結晶化抑制効果を示すことについては全く知られていなかった。
【０００６】
【発明が解決しようとする課題】
本発明は、低温条件下における油脂の結晶化を抑制し、又は固化を防止する効果に優れたポリグリセリン脂肪酸エステルを提供することを目的とする。また本発明は、上記ポリグリセリン脂肪酸エステルを含むことにより、低温雰囲気下においても常温保存時と同等の外観を有する油脂食品を提供することを目的とする。
【０００７】
【課題を解決するための手段】
上述の課題を解決するために、本発明者が鋭意研究を重ねた結果、構成脂肪酸としてエルカ酸を主成分とするポリグリセリン脂肪酸エステルによって、上記の課題を解決することができるという知見が見出された。
【０００８】
本発明は、上記の知見に基づいてなされたものであって、その要旨は、上記ポリグリセリン脂肪酸エステルの構成脂肪酸がエルカ酸および炭素数８〜２２の飽和脂肪酸および不飽和脂肪酸より１種以上選ばれたものよりなることを特徴とするものである。
【０００９】
また上記ポリグリセリン脂肪酸エステルとしては、重合度２〜１５のポリグリセリンを用い、かつポリグリセリンと脂肪酸とのエステル化率が８０重量％以上であることを特徴とするものである。
【００１０】
また本発明の内容としては、上記油脂の結晶化抑制剤であるポリグリセリン脂肪酸エステルを使用した油脂およびこの油脂を含んでなる食品を対象としたものを含んでいる。
【００１１】
【発明の実施の形態】
以下、本発明を詳細に説明する。本発明におけるポリグリセリン脂肪酸エステルの構成脂肪酸は、エルカ酸を主成分としたものと、他に炭素数８〜２２の飽和脂肪酸および不飽和脂肪酸より１種以上から選ばれたものよりなっている。「エルカ酸を主成分としたもの」はエルカ酸が構成脂肪酸中に最も多く含まれていることを意味し、その含有量は４０重量％以上が好ましい。また、構成脂肪酸の組み合わせについては特に限定するものではなく、その配合割合についても特に限定するものではない。
【００１２】
本発明のポリグリセリン脂肪酸エステルに使用するポリグリセリンは、水酸基価から算出した平均重合度で２〜１５である。
【００１３】
本発明のポリグリセリン脂肪酸エステルのポリグリセリンに対する脂肪酸のエステル化率は８０重量％以上であることが好ましく、それ以下であると結晶化を抑制する効果が低下する。
【００１４】
本発明の油脂とは、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、米糠油、小麦胚芽油、パーム油、パーム核油、ヤシ油、カカオ脂、牛脂、ラード、鶏脂、乳脂、魚油、アザラシ油、藻類油、中鎖トリグリセライド、ジグリセライド、品質改良によって低飽和化されたこれらの油脂およびこれらの水素添加油脂、分別油脂などが挙げられるがこれに限定するものではない。
【００１５】
本発明の油脂を含有する食品としては、ドレッシング、マヨネーズ、マーガリン、菓子類、ケーキ、飲料等が挙げられるが油脂を含有する食品であればこれに限定するものではない。
【００１６】
【発明の効果】
本発明のポリグリセリン脂肪酸エステルである、エルカ酸を主成分とした脂肪酸組成を有するものを用いることによって、低温雰囲気でも常温保存時と同等の外観を保持する油脂を得ることができる。
【００１７】
また、上記ポリグリセリン脂肪酸エステルを含有した油脂を使用することによって、結晶が生じて外観を損ねることもなく、固化して作業性を悪化させることもない為、この油脂を食品に使用することによって、油脂の結晶化に起因する外観や食感の悪化を防止することができる。
【００１８】
【実施例】
次に、本発明を実施例及び比較例により詳細に説明するが、本発明はこれらの例によって何ら限定されるものではない。ポリグリセリン脂肪酸エステルは以下のように合成した。
【００１９】
実施例１
デカグリセリン１００ｇとエルカ酸２７０．４ｇ、ミリスチン酸１８２．４ｇから成る混合脂肪酸を反応容器に入れ、触媒及び窒素気流下、２５０℃で反応させ、エステル化率９５％のポリグリセリン脂肪酸エステルを得た。
【００２０】
実施例２
ヘキサグリセリン１００ｇとエルカ酸２７０．４ｇ、パルミチン酸１０２．４ｇ、ラウリン酸８０．０ｇから成る混合脂肪酸を反応容器に入れ、触媒及び窒素気流下、２５０℃で反応させ、エステル化率９１％のポリグリセリン脂肪酸エステルを得た。
【００２１】
比較例１
デカグリセリン１００ｇとオレイン酸２２５．６ｇ、ミリスチン酸１８２．４ｇから成る混合脂肪酸を反応容器に入れ、触媒及び窒素気流下、２５０℃で反応させ、エステル化率９４％のポリグリセリン脂肪酸エステルを得た。
【００２２】
比較例２
デカグリセリン１００ｇとエルカ酸１８０．３ｇ、ミリスチン酸２４３．２ｇから成る混合脂肪酸を反応容器に入れ、触媒及び窒素気流下、２５０℃で反応させ、エステル化率９６％のポリグリセリン脂肪酸エステルを得た。
【００２３】
比較例３
デカグリセリン１００ｇとエルカ酸５４０．８ｇを反応容器に入れ、触媒及び窒素気流下、２５０℃で反応させ、エステル化率９２％のポリグリセリン脂肪酸エステルを得た。
【００２４】
比較例４
ヘキサグリセリン１００ｇとパルミチン酸１３３．１ｇ、ラウリン酸１０４．０ｇから成る混合脂肪酸を反応容器に入れ、触媒及び窒素気流下、２５０℃で反応させ、エステル化率６３％のポリグリセリン脂肪酸エステルを得た。
【００２５】
比較例５
デカグリセリン１００ｇとエルカ酸１９７．４ｇ、ミリスチン酸７４．８ｇから成る混合脂肪酸を反応容器に入れ、触媒及び窒素気流下、２５０℃で反応させ、エステル化率７３％のポリグリセリン脂肪酸エステルを得た。
【００２６】
試験例１
実施例１〜２及び比較例１〜５で得られたポリグリセリン脂肪酸エステルをナタネ油に０．１重量％加え、８０℃で十分加温溶融した。その後、０℃の恒温槽中に放置して油脂の結晶が析出するまでの時間を測定した。試験例の結果を表１に示す。本発明のポリグリセリン脂肪酸エステルを添加した油脂は、無添加の場合に比べ４倍以上の時間まで効果を持続し、結晶化を起こしにくいものとなっていることが分かった。従って、本発明のポリグリセリン脂肪酸エステルを添加した油脂は、低温において十分に油脂の結晶化を抑制し、さらにこの油脂を食品に使用することで油脂の結晶化に起因する外観や食感の悪化を防止することができるのは明白である。
【００２７】
【表１】
BACKGROUND OF THE INVENTION
The present invention relates to a polyglycerol fatty acid ester having an effect of suppressing crystallization or solidification of fats and oils. More specifically, by adding the polyglycerin fatty acid ester which is the crystallization inhibitor of fats and oils of the present invention, even when stored at low temperatures, the fats and fats and fats and foods that retain the same appearance as when stored at room temperature About.
[0002]
[Prior art]
Edible liquid oils that are liquid at room temperature include soybean oil, rapeseed oil, cottonseed oil, corn oil, sesame oil, and the like, and are used for many purposes such as frying and dressing for home use or business use. However, because edible liquid oil has a versatile triglyceride composition, when it is cooled and stored at a low temperature, high melting point triglyceride crystals are precipitated. Usually, during the production of edible liquid oil, the wintering operation is performed to separate the solid fat portion. However, the solid fat that is slightly contained in winter still causes various problems. .
[0003]
For example, in the case of frying oil, the entire product becomes cloudy due to the precipitation of crystals during low-temperature storage, which impairs the product image. Moreover, it loses fluidity due to solidification and cannot be taken out from the container. In the case of emulsified foods such as dressing, if the oil phase is crystallized under freezing or refrigeration conditions, the oil phase is crystallized to cause coalescence of oil droplets, resulting in emulsion breakage.
[0004]
As a method for solving these problems, a technique of adding an emulsifier and suppressing crystallization of fats and oils is known. For example, a method of adding a polyglycerin fatty acid ester (JP-A 63-63343, JP-A 9-299027, JP-A 10-245583) or a mixture of polyglycerin fatty acid ester and sorbitan fatty acid ester is added. However, the effect is not sufficient for improving the cold resistance of liquid oil and the freezing resistance of emulsified foods such as emulsions under low temperature conditions of 0 ° C. or lower. It was.
[0005]
On the other hand, as a polyglycerin fatty acid ester that suppresses crystallization of fats and oils, as a component fatty acid containing erucic acid, JP-A-9-299027 discloses an unsaturated fatty acid having 16 to 22 carbon atoms in an amount of 5 to 15% by weight. The polyglycerol fatty acid ester to be contained has been proposed, but this is not sufficient as an effect in a low temperature atmosphere. In addition, it has not been known at all that polyglycerin fatty acid ester mainly composed of erucic acid as a constituent fatty acid has an effect of suppressing crystallization of fats and oils.
[0006]
[Problems to be solved by the invention]
An object of this invention is to provide the polyglycerol fatty acid ester excellent in the effect which suppresses the crystallization of fats and oils on low temperature conditions, or prevents solidification. Another object of the present invention is to provide an oily and fat food having an appearance equivalent to that at normal temperature storage even in a low temperature atmosphere by including the polyglycerin fatty acid ester.
[0007]
[Means for Solving the Problems]
In order to solve the above-mentioned problems, the present inventors have conducted intensive research, and as a result, have found that the above-mentioned problems can be solved by a polyglycerin fatty acid ester mainly composed of erucic acid as a constituent fatty acid. It was done.
[0008]
The present invention has been made on the basis of the above knowledge, and the gist thereof is that the constituent fatty acid of the polyglycerin fatty acid ester is selected from erucic acid and saturated fatty acids having 8 to 22 carbon atoms and unsaturated fatty acids. It is characterized by being made up of.
[0009]
Moreover, as said polyglyceryl fatty acid ester, polyglycerin with a polymerization degree of 2-15 is used, and the esterification rate of polyglycerin and a fatty acid is 80 weight% or more.
[0010]
The contents of the present invention include oils and fats using polyglycerin fatty acid esters which are the oil and fat crystallization inhibitors and foods containing these oils and fats.
[0011]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail. The constituent fatty acid of the polyglycerin fatty acid ester in the present invention is composed of erucic acid as a main component and one selected from one or more of saturated fatty acids and unsaturated fatty acids having 8 to 22 carbon atoms. “A substance mainly composed of erucic acid” means that erucic acid is contained most in the constituent fatty acid, and the content is preferably 40% by weight or more. Moreover, it does not specifically limit about the combination of a constituent fatty acid, and it does not specifically limit also about the mixture ratio.
[0012]
The polyglycerin used in the polyglycerin fatty acid ester of the present invention has an average degree of polymerization of 2 to 15 calculated from the hydroxyl value.
[0013]
The esterification rate of the fatty acid to the polyglycerol of the polyglycerol fatty acid ester of the present invention is preferably 80% by weight or more, and if it is less than that, the effect of suppressing crystallization is lowered.
[0014]
The fats and oils of the present invention are 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, straw oil, tea seed oil, sesame oil, olive oil, rice bran oil, wheat germ oil, palm oil, palm kernel oil, coconut oil, cacao butter, beef tallow, lard, chicken fat, milk fat, fish oil, seal oil, Examples include, but are not limited to, algal oil, medium chain triglyceride, diglyceride, these oils and fats that have been low-saturated by quality improvement, hydrogenated oils, and fractionated oils and fats.
[0015]
Examples of the food containing the fats and oils of the present invention include dressings, mayonnaise, margarines, confectionery, cakes, beverages and the like, but are not limited thereto as long as they contain fats and oils.
[0016]
【The invention's effect】
By using the polyglycerin fatty acid ester of the present invention having a fatty acid composition mainly composed of erucic acid, an oil and fat having the same appearance as when stored at room temperature can be obtained even in a low temperature atmosphere.
[0017]
In addition, by using the fats and oils containing the polyglycerin fatty acid ester, crystals are not generated and the appearance is not impaired, and the workability is not deteriorated by solidification. Moreover, the deterioration of the external appearance and food texture resulting from crystallization of fats and oils can be prevented.
[0018]
【Example】
Next, although an example and a comparative example explain the present invention in detail, the present invention is not limited at all by these examples. Polyglycerin fatty acid ester was synthesized as follows.
[0019]
Example 1
A mixed fatty acid consisting of 100 g of decaglycerin, 270.4 g of erucic acid and 182.4 g of myristic acid was put in a reaction vessel and reacted at 250 ° C. under a catalyst and a nitrogen stream to obtain a polyglycerin fatty acid ester having an esterification rate of 95%. .
[0020]
Example 2
A mixed fatty acid consisting of 100 g of hexaglycerine, 270.4 g of erucic acid, 102.4 g of palmitic acid, and 80.0 g of lauric acid is placed in a reaction vessel and reacted at 250 ° C. in a catalyst and nitrogen stream to obtain a polyester having an esterification rate of 91%. A glycerin fatty acid ester was obtained.
[0021]
Comparative Example 1
A mixed fatty acid consisting of 100 g of decaglycerin, 225.6 g of oleic acid and 182.4 g of myristic acid was put in a reaction vessel and reacted at 250 ° C. under a catalyst and nitrogen stream to obtain a polyglycerin fatty acid ester having an esterification rate of 94%. .
[0022]
Comparative Example 2
A mixed fatty acid consisting of 100 g of decaglycerin, 180.3 g of erucic acid, and 243.2 g of myristic acid was placed in a reaction vessel and reacted at 250 ° C. under a catalyst and a nitrogen stream to obtain a polyglycerin fatty acid ester having an esterification rate of 96%. .
[0023]
Comparative Example 3
100 g of decaglycerin and 540.8 g of erucic acid were put in a reaction vessel and reacted at 250 ° C. under a catalyst and a nitrogen stream to obtain a polyglycerin fatty acid ester having an esterification rate of 92%.
[0024]
Comparative Example 4
A mixed fatty acid consisting of 100 g of hexaglycerin, 133.1 g of palmitic acid and 104.0 g of lauric acid was put in a reaction vessel and reacted at 250 ° C. under a catalyst and nitrogen stream to obtain a polyglycerin fatty acid ester having an esterification rate of 63%. .
[0025]
Comparative Example 5
A mixed fatty acid consisting of 100 g of decaglycerin, 197.4 g of erucic acid, and 74.8 g of myristic acid was placed in a reaction vessel and reacted at 250 ° C. under a catalyst and nitrogen stream to obtain a polyglycerin fatty acid ester having an esterification rate of 73%. .
[0026]
Test example 1
The polyglycerin fatty acid ester obtained in Examples 1-2 and Comparative Examples 1-5 was added to rapeseed oil in an amount of 0.1% by weight and sufficiently heated and melted at 80 ° C. Then, it was left to stand in a 0 degreeC thermostat, and time until fats and oils crystals precipitated was measured. The results of the test examples are shown in Table 1. It was found that the fats and oils to which the polyglycerin fatty acid ester of the present invention was added sustained the effect up to four times or more as compared with the case where no addition was made, and hardly caused crystallization. Therefore, the fats and oils to which the polyglycerin fatty acid ester of the present invention is added sufficiently suppresses the crystallization of fats and oils at a low temperature, and further the use of the fats and oils in foods deteriorates the appearance and texture due to the crystallization of fats and oils. It is clear that this can be prevented.
[0027]
[Table 1]
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001009861A JP3935676B2 (en) | 2001-01-18 | 2001-01-18 | Oil and fat crystallization inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001009861A JP3935676B2 (en) | 2001-01-18 | 2001-01-18 | Oil and fat crystallization inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002212587A JP2002212587A (en) | 2002-07-31 |
| JP3935676B2 true JP3935676B2 (en) | 2007-06-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001009861A Expired - Lifetime JP3935676B2 (en) | 2001-01-18 | 2001-01-18 | Oil and fat crystallization inhibitor |
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| Country | Link |
|---|---|
| JP (1) | JP3935676B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4496125B2 (en) * | 2004-09-24 | 2010-07-07 | 花王株式会社 | Acid oil-in-water emulsified composition |
| TWI363600B (en) * | 2004-09-21 | 2012-05-11 | Kao Corp | Acidic oil-in-water emulsion composition |
| JP4601082B2 (en) * | 2004-09-24 | 2010-12-22 | 花王株式会社 | Acid oil-in-water emulsified composition |
| US9271512B2 (en) | 2008-07-24 | 2016-03-01 | Taiyo Kagaku Co., Ltd. | Crystal growth inhibitor for fats and oils |
| JP5872217B2 (en) | 2010-09-14 | 2016-03-01 | 花王株式会社 | Oil composition |
-
2001
- 2001-01-18 JP JP2001009861A patent/JP3935676B2/en not_active Expired - Lifetime
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| Publication number | Publication date |
|---|---|
| JP2002212587A (en) | 2002-07-31 |
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