JP4297604B2 - seasoning - Google Patents

Description

【００４０】
〔実施例７〕
＜高度不飽和脂肪酸含有グリセリドの製造方法＞
マグロ油１ｋｇ、イオン交換水１ｋｇ、リパーゼ粉末３ｇ（商品名；リパーゼＯＦ、名糖産業製）を四つ口フラスコに入れ、窒素雰囲気下、４０℃にて８時間加水分解反応を行った。反応物から水層を静置分離後、油層を分子蒸留に供し、遊離脂肪酸を除去して加水分解油を得た。この加水分解油はＤＨＡ４３重量％、ＥＰＡ８重量％を含有する高度不飽和脂肪酸のトリグリセリドとジグリセリドの（８０：２０重量比）混合物であった。
【００４１】
＜調味料製造方法＞
実施例１記載の原料Ａを加熱し、８５℃まで達したら、実施例１記載の原料Ｂを溶解し、溶解後３０℃まで冷却しＤ液とする。Ｄ液１００ｍｌに、上記製造方法で得たＤＨＡ４３重量％、ＥＰＡ８重量％を含有する高度不飽和脂肪酸のトリグリセリドとジグリセリドの（８０：２０重量比）混合物を１０重量％添加した後、ホモジナイザーを用いて乳化した。次いで実施例１記載の原料Ｃを添加混合し、高度不飽和脂肪酸グリセリド含有調味料ｇ（以下、単に調味料ｇ）を得た。
【００４２】
＜原料＞
（調味料原料Ｈ）
砂糖 １０部
醤油 １００部
昆布 ７部
食塩 ４０部
【００４３】
原料Ｈに、上記製造方法で得たＤＨＡ４３重量％、ＥＰＡ８重量％を含有する高度不飽和脂肪酸のトリグリセリドとジグリセリドの（８０：２０重量比）混合物を１０重量％添加した後、ホモジナイザーを用いて乳化した。次いで実施例１記載の原料Ｃを添加混合し、高度不飽和脂肪酸グリセリド含有調味料ｈ（以下、単に調味料ｈ）を得た。
【００４４】
実施例１記載の原料Ａを加熱し、８５℃まで達したら、実施例１記載の原料Ｂを溶解し、溶解後３０℃まで冷却しＤ液とする。Ｄ液１００ｍｌに、上記製造方法で得たＤＨＡ４３重量％、ＥＰＡ８重量％を含有する高度不飽和脂肪酸のトリグリセリドとジグリセリドの（８０：２０重量比）混合物を１０重量％添加した後、ホモジナイザーを用いて乳化し、高度不飽和脂肪酸グリセリド含有調味料ｉ（以下、単に調味料ｉ）を得た。
【００４５】
実施例４記載の方法に従い、液体ｈを得た。液体ｈ１００ｍｌに、上記製造方法で得たＤＨＡ４３重量％、ＥＰＡ８重量％を含有する高度不飽和脂肪酸のトリグリセリドとジグリセリドの（８０：２０重量比）混合物を１０重量％添加した後、ホモジナイザーを用いて乳化し、高度不飽和脂肪酸グリセリド含有調味料ｊ（以下、単に調味料ｊ）を得た。
【００４６】
＜酸化安定性試験＞
上記調味料ｇ〜ｊについて酸化安定性試験を行った。酸化安定性は、各調味料を室温で１ヶ月放置後の過酸化物価（ＰＶ）を測定し評価した。結果を表２に示す。コントロールｃは調味料ｇから、醤油、味噌及びトマトピューレの代わりに水としたもの、コントロールｄは、水に、上記製造方法で得たＤＨＡ４３重量％、ＥＰＡ８重量％を含有する高度不飽和脂肪酸のトリグリセリドとジグリセリドの（８０：２０重量比）混合物を１０重量％添加した後、ホモジナイザーを用いて乳化したものとした。
【００４７】
【表２】

【００４８】
【発明の効果】
本発明により、広くどのような食品とも一緒に食卓で高度不飽和脂肪酸を摂取することができ、且つ酸化安定性及び風味の良好な高度不飽和脂肪酸を含む調味料を提供することができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a seasoning containing a highly unsaturated fatty acid component that can make a highly unsaturated fatty acid having various physiological functions widely and stably in any food.
[0002]
[Prior art and problems to be solved by the invention]
Polyunsaturated fatty acids such as docosahexaenoic acid (DHA), icosapentaenoic acid (EPA), conjugated linoleic acid (CLA) and the like are useful in the living body and have various physiological functions, and thus have been attracting attention and being actively consumed in recent years. However, since it is a highly unsaturated acid, there are drawbacks such as being easily oxidized and degrading and easily generating a return odor. For this reason, it has been used after various devices such as combined use of various antioxidants, coating agents, masking agents, etc., or encapsulation (JP 59-82070 A, JP 6-133707 A). etc).
[0003]
Unlike drugs, foods are in good balance with other foods and are preferably taken as meals if possible. However, the amount or range of use of conventional products containing highly unsaturated fatty acids is limited, and it has been difficult to take them on a table together with general foods.
[0004]
In particular, in the case of a meal that consumes a large amount of livestock meat, poultry meat or processed products thereof, it is considered that it is meaningful for health to take unsaturated fatty acids in a balanced manner. There was no suitable product containing.
[0005]
Therefore, an object of the present invention is to provide a seasoning containing a highly unsaturated fatty acid that can be taken with a wide variety of foods at the table and that has good oxidative stability and flavor. It is in.
[Means for Solving the Problems]
As a result of intensive studies to achieve the above object, the present inventors have found that one or more seasonings mainly composed of fermented processed foods of soybeans, fermented processed foods of seafood or tomato ingredients widely used on the table. Or, it has been found that by adding highly unsaturated fatty acid glycerides to the combination of these and a spice, a food having a high oxidative stability and good flavor can be obtained and used for a wide range of foods, and the present invention has been completed. .
[0006]
That is, the present invention contains a highly unsaturated fatty acid glyceride in the form of 1,3-diacyl glyceride, 1-monoacyl glyceride or 3-monoacyl glyceride, and contains the above highly unsaturated fatty acid glyceride. In contrast, components obtained by fermenting soybeans using isolated or partially concentrated diglycerides and monoglycerides from the reaction products obtained by performing hydrolysis, transesterification or esterification reactions alone or in combination. The present invention provides a seasoning characterized by containing any one or more of fermented seafood and tomato ingredients .
[0007]
Moreover, this invention provides the said seasoning containing any 1 type, or 2 or more types of the component which fermented soybean, the component which fermented seafood, or the tomato component.
[0008]
Furthermore, this invention provides the said seasoning whose component which fermented soybean is soy sauce or miso.
[0009]
Moreover, this invention provides the said seasoning whose tomato component is Worcester sauce.
[0010]
Moreover, this invention provides the said seasoning containing a spice.
[0011]
Furthermore, this invention provides the said seasoning used for meat dishes.
[0012]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the seasoning of the present invention will be described in detail.
[0013]
Polyunsaturated fatty acid glycerides used in the seasoning of the present invention include, for example, arachidonic acid (AA), docosahexaenoic acid (DHA), icosapentaenoic acid (EPA), conjugated linoleic acid (CLA), conjugated docosahexaenoic acid (CDHA), and conjugated icosapentaene. A fatty acid having an unsaturation degree of 2 or more such as acid (CEPA) is bonded to one molecule or two molecules per molecule of glycerin. The polyunsaturated fatty acid glyceride may be a diglyceride or a monoglyceride, or a combination of two or more. In particular 1,3-diacyl glyceride or 1-mono-acyl glyceride, 3-monoacyl glyceride types Irare for Ri by the present invention, especially 1,3-diacyl glyceride type of the fatty acid is preferably used.
Polyunsaturated fatty acids can be considered in combination depending on the purpose.
[0014]
Of the total fatty acid content, the highly unsaturated fatty acid content is 3 to 100% by weight, preferably 10 to 100% by weight. When the content is less than 3% by weight, the intake of unintended fatty acids increases when blended with a seasoning, and the amount added is limited. Examples of the raw material of the highly unsaturated fatty acid-containing glyceride used in the present invention include sardine oil, tuna oil and other fish oil, perilla oil, sesame oil, soybean oil, rapeseed oil, safflower oil, and the like. Or it can be used in combination. Also, those obtained by alkali conjugating these oils and fats by a conventional method can be used.
[0015]
The highly unsaturated fatty acid-containing glyceride can be obtained by subjecting the above raw materials to reactions such as hydrolysis, transesterification and esterification alone or in appropriate combination. The molecular distillation, using a column chromatography, liquid-liquid extraction method or the like, in either radio glycerides of these reactions, to use those monoglyceride was concentrated isolated or partially.
[0016]
The component fermented with soybean used in the present invention is, for example, a product in which soybean is essential, and barley, rice, etc. as a raw material and fermented with koji, yeast, and other microorganisms, such as soy sauce, miso, natto, Tempe etc. are mentioned. It is particularly preferable to use soy sauce and miso as a general-purpose seasoning. Hereinafter, these are collectively referred to as soybean fermented seasoning.
[0017]
The component obtained by fermenting the seafood used in the present invention is a component fermented with salmon, yeast, and other microorganisms using fish as raw materials, and examples include fish sauce such as squid soy sauce, sardine soy sauce, salt juice, and nanpura. Hereinafter, these are collectively referred to as fish soy seasonings.
[0018]
The seasoning containing the tomato component used in the present invention contains tomato components such as tomato juice and tomato pulp, and is a seasoning that does not ferment or ferment them, tomato juice, tomato paste, tomato puree, tomato ketchup, Examples include chili sauce, tomato sauce, and Worcester sauce. Although these may be directly used as beverages, they are collectively referred to as tomato seasonings hereinafter. It is particularly preferable to use Worcester sauce as a general-purpose seasoning.
[0019]
In addition, in these fermented soybean seasonings, fish sauce seasonings and tomato seasonings, spices such as celery, parsley, clove, chimpi, nutmeg, cinnamon, sage, thyme, pepper, laurel, garlic, ginger, etc. 1 The use of seeds or a combination of two or more thereof is more consistent with the object of the present invention. In particular, pepper, garlic, ginger and the like are suitable for improving the flavor and stability of the seasoning of the present invention.
[0020]
The content of highly unsaturated fatty acid glyceride added to the seasoning of the present invention is preferably 0.1 to 30% by weight, more preferably 5 to 15% by weight. If it is less than 0.1% by weight, it is too small to exhibit the physiologically active effect of the highly unsaturated fatty acid glyceride, and if it is more than 30% by weight, the texture becomes oily.
[0021]
The method of adding the highly unsaturated fatty acid glyceride is emulsified, dispersed or solubilized as it is or in combination with an emulsifier, paste or the like. A separation type that stirs and disperses at the time of use while being separated is also possible. For emulsification or solubilization, a homogenizer or homomixer may be used, and solids such as spices may be added after emulsification.
[0022]
Although the use of the seasoning of this invention is not specifically limited, For example, it can be used for meat dishes, fish dishes, vegetable dishes, etc. In particular, the use of highly unsaturated fatty acids in a well-balanced manner is preferred, so use in meat dishes such as yakiniku and steak is preferred.
[0023]
In the seasoning of the present invention, components that are usually used in seasonings can be blended within a range that does not impair the effects of the present invention. For example, vegetables such as onions, carrots, celery, lettuce, cabbage, fruits such as apples and tangerines, processed vegetables, processed fruits, sugars such as sugar, liquid sugar, fructose and caramel, polysaccharides such as starch, wine And alcohols such as sake and mirin, sweeteners such as sorbitol, pastes, food emulsifiers, antioxidants, vitamins, proteins, amino acids, edible fats and oils, vinegar, salt, water, and the like.
[0024]
【Example】
EXAMPLES Hereinafter, although an Example demonstrates this invention in more detail, this invention is not limited by these. In the following examples, all “parts” are based on weight.
Of the following Examples 1 to 7, Examples 2, 3, and 5 to 7 are examples of the present invention, and Examples 1 and 4 are reference examples.
[0025]
[Example 1]
<Raw material>
(Condiment raw material A)
Deep mouth soy sauce 30 parts Red miso 2 parts (seasoning ingredient B)
Sugar 8 parts Mirin 5 parts Sorbitol 5 parts (Condiment ingredient C)
Black pepper 0.05 parts Pepper powder 0.05 parts Sesame oil 2 parts Apple vinegar 1 part Apple pulp 10 parts Onion paste 7 parts Tomato puree 5 parts Garlic paste 4 parts Ginger paste 2 parts Sodium glutamate 2 parts Fried sesame 2 parts Water 15 parts [0026]
<Condiment manufacturing method>
The raw material A is heated, and when the temperature reaches 85 ° C., the raw material B is dissolved. 10 ml of highly unsaturated fatty acid triglyceride (sardine oil) containing 10% by weight of docosahexaenoic acid (DHA) and 15% by weight of icosapentaenoic acid (EPA) was added to 100 ml of Liquid D, and the mixture was stirred and emulsified with a homomixer at 1500 rpm. Subsequently, the raw material C was added and mixed to obtain a highly unsaturated fatty acid glyceride-containing seasoning a (hereinafter simply referred to as seasoning a).
[0027]
[Example 2]
1 kg of tuna oil, 100 g of glycerin and 0.5 g of potassium carbonate were placed in a four-necked flask and stirred at 200 mmHg and 200 ° C. for 2 hours in a nitrogen gas stream. After removing glycerin from the reaction product, the oil layer was subjected to molecular distillation, and a diglyceride fraction (DHA 22 wt%, EPA 7 wt%) was collected.
[0028]
100 ml of the raw material D liquid described in Example 1 was added to 10 ml of the highly unsaturated fatty acid diglyceride containing 22% by weight of DHA and 7% by weight of EPA, and the mixture was stirred and emulsified with a homomixer at 1500 rpm. Next, the raw material C was added and mixed to obtain a highly unsaturated fatty acid glyceride-containing seasoning b (hereinafter simply referred to as seasoning b).
[0029]
Example 3
500 g of sardine oil, 1 kg of glycerin and 5 g of potassium carbonate were placed in a four-necked flask and stirred at 200 mmHg and 200 ° C. for 2 hours in a nitrogen gas stream. After removing glycerin from the reaction product, the oil layer was subjected to molecular distillation, and a monoglyceride fraction (DHA 12 wt%, EPA 18 wt%) was collected.
[0030]
100 ml of the raw material D solution described in Example 1 was added to 10 ml of the highly unsaturated fatty acid monoglyceride containing 12% by weight of DHA and 18% by weight of EPA, and stirred and emulsified with a homomixer at 1500 rpm. Subsequently, the raw material C was added and mixed to obtain a highly unsaturated fatty acid glyceride-containing seasoning c (hereinafter simply referred to as seasoning c).
[0031]
Example 4
<Raw material>
(Condiment raw material E)
Onion 55 parts carrot 22 parts garlic 7 parts (seasoning ingredient F)
Tomato paste 66 parts Vinegar 100 parts (Condiment ingredient G)
Pepper 5 parts Himeyuki 4 parts Chinpi 4 parts Laurel 3 parts Sage 3 parts Nicke 3 parts Time 3 parts Scratch 3 parts Pepper 1 part [0032]
<Condiment manufacturing method>
The following seasonings were produced according to a conventional method for producing Worcester sauce.
The raw material E was cut into an appropriate size, 200 parts of water was added and the mixture was boiled in an open flame for 3 hours, cooled to room temperature, and solid-liquid separated with a centrifuge to obtain liquid e.
The raw material F was steamed until it became paste-like and allowed to cool to obtain a paste f.
The raw material G was immersed for a whole day and night in 342 parts of boiling water and filtered through a filter cloth to obtain liquid g.
Liquid e was heated to 50 ° C., paste f was added and stirred, 15 parts of caramel and 7 parts of starch were added and dissolved well, and then vinegar was added to obtain liquid h.
[0033]
10 ml of highly unsaturated fatty acid triglyceride (tuna oil) containing 22% by weight of DHA and 7% by weight of EPA is added to 100 ml of liquid h, and the mixture is stirred and emulsified with a homomixer at 1500 rpm, and a highly unsaturated fatty acid glyceride-containing seasoning d (hereinafter simply referred to as seasoning d). )
[0034]
Example 5
300 g of ethylene glycol and 100 g of potassium hydroxide were placed in a 2 L four-necked flask and heated to 100 ° C. while blowing nitrogen. Next, 200 g of ethyl linoleate was added to the flask and heated at 180 ° C. for 2.5 hours under a nitrogen stream. After cooling the reaction solution to room temperature, hydrochloric acid was added to adjust the pH of the reaction solution to 3, and 50 mL of distilled water was further added and stirred for 5 minutes. Subsequently, hexane extraction was performed three times, and then the hexane solution was washed successively with 5% NaCl and distilled water. After adding anhydrous sodium sulfate to the hexane solution and dehydrating and filtering, hexane was distilled off using a rotary evaporator to obtain conjugated linoleic acid (CLA).
[0035]
Fatty acid 800 g, CLA 200 g, and glycerin 100 g obtained by saponifying and decomposing DHA tuna oil (see Japan Oil Chemistry Association, Standard Oil Analysis Test Method 2.4.8) were placed in an Erlenmeyer flask, and immobilized lipase ( Novo, IM-20) (60 g) was added, and the atmosphere in the flask was replaced with nitrogen, followed by shaking at 40 ° C. for 24 hours. After separating the immobilized lipase, the reaction oil was subjected to molecular distillation, and a diglyceride fraction (DHA 20 wt%, CLA 20 wt%) was collected.
[0036]
To 10 ml of the highly unsaturated fatty acid diglyceride containing 20% by weight of DHA and 20% by weight of CLA, 100 ml of the liquid h described in Example 4 was added and stirred and emulsified with a homomixer at 1500 rpm. Subsequently, the raw material F was added and mixed to obtain a highly unsaturated fatty acid glyceride-containing seasoning e (hereinafter simply referred to as seasoning e).
[0037]
Example 6
Similarly, 10 ml of highly unsaturated fatty acid monoglyceride containing 12% of DHA and 18% by weight of EPA obtained in Example 3 was added to 100 ml of liquid h, followed by stirring and emulsification with a homomixer at 1500 rpm. Subsequently, the raw material F was added and mixed to obtain a highly unsaturated fatty acid glyceride-containing seasoning f (hereinafter simply referred to as seasoning f).
[0038]
<Flavor test>
About the said seasoning, the flavor after 3 months and 6 months leaving at room temperature was evaluated. The evaluation results are shown in Table 1. However, the control a was water from Example 1 instead of soy sauce, miso and tomato puree, and the control b was water from Example 4 instead of tomato paste.
[0039]
[Table 1]

[0040]
Example 7
<Method for producing highly unsaturated fatty acid-containing glyceride>
1 kg of tuna oil, 1 kg of ion-exchanged water, and 3 g of lipase powder (trade name; Lipase OF, manufactured by Meika Sangyo Co., Ltd.) were placed in a four-necked flask and subjected to a hydrolysis reaction at 40 ° C. for 8 hours in a nitrogen atmosphere. After the aqueous layer was left and separated from the reaction product, the oil layer was subjected to molecular distillation to remove free fatty acids to obtain hydrolyzed oil. This hydrolyzed oil was a mixture of triglycerides and diglycerides (80:20 weight ratio) of highly unsaturated fatty acids containing 43% by weight of DHA and 8% by weight of EPA.
[0041]
<Condiment manufacturing method>
When the raw material A described in Example 1 is heated and reaches 85 ° C., the raw material B described in Example 1 is dissolved, and after dissolution, cooled to 30 ° C. to obtain a liquid D. After adding 10% by weight of a highly unsaturated fatty acid triglyceride and diglyceride (80:20 weight ratio) mixture containing 43% by weight of DHA and 8% by weight of EPA obtained by the above production method to 100 ml of solution D, using a homogenizer Emulsified. Subsequently, the raw material C described in Example 1 was added and mixed to obtain a highly unsaturated fatty acid glyceride-containing seasoning g (hereinafter simply referred to as seasoning g).
[0042]
<Raw material>
(Seasoning material H)
Sugar 10 parts Soy sauce 100 parts Kelp 7 parts Salt 40 parts [0043]
10% by weight of a highly unsaturated fatty acid triglyceride and diglyceride (80:20 weight ratio) mixture containing 43% by weight of DHA and 8% by weight of EPA obtained by the above production method was added to the raw material H, followed by emulsification using a homogenizer. did. Subsequently, the raw material C described in Example 1 was added and mixed to obtain a highly unsaturated fatty acid glyceride-containing seasoning h (hereinafter simply referred to as seasoning h).
[0044]
When the raw material A described in Example 1 is heated and reaches 85 ° C., the raw material B described in Example 1 is dissolved, and after dissolution, cooled to 30 ° C. to obtain a liquid D. After adding 10% by weight of a highly unsaturated fatty acid triglyceride and diglyceride (80:20 weight ratio) mixture containing 43% by weight of DHA and 8% by weight of EPA obtained by the above production method to 100 ml of solution D, using a homogenizer Emulsified to obtain a highly unsaturated fatty acid glyceride-containing seasoning i (hereinafter simply referred to as seasoning i).
[0045]
According to the method described in Example 4, liquid h was obtained. 10% by weight of a polyunsaturated fatty acid triglyceride and diglyceride (80:20 weight ratio) mixture containing 43% by weight of DHA and 8% by weight of EPA obtained by the above production method was added to 100 ml of liquid h, followed by emulsification using a homogenizer. Thus, a highly unsaturated fatty acid glyceride-containing seasoning j (hereinafter simply referred to as seasoning j) was obtained.
[0046]
<Oxidation stability test>
An oxidation stability test was performed on the seasonings g to j. The oxidation stability was evaluated by measuring the peroxide value (PV) after leaving each seasoning for 1 month at room temperature. The results are shown in Table 2. Control c is water from the seasoning g instead of soy sauce, miso and tomato puree, and control d is a highly unsaturated fatty acid containing 43% by weight of DHA and 8% by weight of EPA obtained by the above production method in water. After adding 10% by weight of a mixture of triglyceride and diglyceride (80:20 weight ratio), the mixture was emulsified using a homogenizer.
[0047]
[Table 2]

[0048]
【The invention's effect】
INDUSTRIAL APPLICABILITY According to the present invention, a highly unsaturated fatty acid can be ingested on a table together with a wide variety of foods, and a seasoning containing a highly unsaturated fatty acid having good oxidation stability and flavor can be provided.

Claims (5)

Containing highly unsaturated fatty acid glycerides in the form of 1,3-diacylglycerides, 1-monoacylglycerides or 3-monoacylglycerides ,
In order to contain the above highly unsaturated fatty acid glyceride, diglyceride and monoglyceride are isolated or isolated from the reaction product obtained by performing hydrolysis, transesterification or esterification reaction alone or in combination with oils and fats. Using a concentrated part,
The seasoning characterized by including any 1 type, or 2 or more types of the component which fermented soybean, the component which fermented seafood, or the tomato component . Seasoning according to claim 1, wherein component fermented the soybeans are soy sauce or miso. Seasoning according to claim 1, wherein said tomato component is Worcestershire sauce. The seasoning of Claim 1, 2 or 3 containing a spice. The seasoning according to any one of claims 1 to 4 , which is used for meat dishes.