JP3919973B2 - Degradation inhibitor during oil heating - Google Patents

Description

【０００５】
（式中、R¹、R²及びR³のうち２個は炭素数12〜22の飽和又は不飽和脂肪酸由来のアシル基を示し、残りの１個は糖残基を示す。）
【０００６】
【発明の実施の形態】
本発明で使用する一般式（１）で表される化合物は、小麦粉、ほうれん草、にんじん等の食材に含まれているもので、合成品でも上記食材から抽出したものでも良い。抽出法としては、ヘキサン、アセトン、クロロホルム、メタノール、エタノールあるいはこれらの混合溶剤で抽出する方法を用いることができる。
糖残基は、グルコース、ガラクトース、スクロース、ラクトース、マルトース、Ｏ−α−ガラクトピラノシル−（１→６）−β−ガラクトピラノース（以下、ジガラクト−スと略記）、グルコサミン、ガラクトサミン等の単糖、二糖、アミノ糖の１ヶの水酸基がグリセリンの水酸基と縮合してエーテル結合を構成した時の糖の残基である。通常は糖の一位の水酸基が結合するが、一位以外の水酸基が結合した構造のものでもよい。
糖残基は、その70％以上がガラクトース残基又はジガラクトース残基であるのが好ましい。また、アシル基は不飽和脂肪酸由来のものが好ましく、アシル基の70％以上がリノレオイル基のものが好ましい。
【０００７】
本発明に使用する油脂は、一般的に使用されている食用油であれば特に制限はないが、天然由来の油脂、例えばサフラワー油、オリーブ油、綿実油、ナタネ油、コーン油、大豆油、パーム油、ひまわり油、ごま油等の植物油が好ましい。これらの油脂はそれぞれ単独で用いてもよく、あるいは適宜混合してもよい。
【０００８】
本発明において、上記化合物の添加量は、油脂中に0.05ppm 以上、好ましくは0.5ppm以上、特に好ましくは１ppm 以上である。
本発明の化合物は、それ自身に匂いがなく、このものを油脂に添加すれば、例えば調理中でも油脂のＣＯＶが上昇し難い、劣化しにくい油脂を提供することができる。その作用機構の詳細は不明であるが、本物質は構造上、一分子中に疎水性部及び親水性部を有し、調理時に発生する油／空気（酸素）界面に存在することで、油脂／酸素の接触を抑えているものと推測される。
その添加量が多くなるほど効果も長期にわたり持続するが、風味の点から1000ppm 以下が望ましい。
【０００９】
本発明の劣化抑制剤には、抗酸化剤、乳化剤等を併用添加できる。抗酸化剤としては、Ｌ−アスコルビン酸パルミテート、トコフェロールの他、スパイス、茶、甘草、ローズマリー等の天然物からの抽出物等が挙げられる。乳化剤としては、ショ糖脂肪酸エステル、有機酸モノグリセリド、ポリグリセリン脂肪酸エステル、リン脂質等が挙げられる。また目的に応じては、各種の風味付与剤（フレーバー）、栄養強化剤、減粘剤等を添加できる。
本発明の劣化抑制剤が添加された油脂は、野菜炒め等の炒め物調理、天ぷら、唐揚げ等の揚げ物調理に好適に利用される。
【００１０】
【実施例】
表１に示す如くコーン油に各種添加剤を配合して、本発明による油脂組成物Ａ〜Ｆを調製した。
【００１１】
【表１】

【００１２】
*1 和光純薬製試薬（０４９−２４９１１）（ほうれん草由来）
*2 ＳＩＧＭＡ製試薬（Ｄ−４６５１）（whole wheat flour 由来）
*3 和光純薬製試薬（０７３−０３９５１）（ほうれん草由来）
*4 ＳＩＧＭＡ製試薬（Ｇ９５２３）（whole wheat flour 由来）
*5 三共（株）製キャロットオイル三共を、クロロホルム／メタノール（２／１）系シリカゲルクロマト、更にメタノール系ＯＤＳゲルクロマトを経て得られたジガラクトシルジグリセロール含有画分（約80％含有物）
*6 市販小麦粉（強力粉）を、ヘキサン／エタノール（２／１）系にて抽出したジガラクトシルジグリセロール含有画分（約30％含有物）
実施例１〜６、比較例１
上記の如く調製した油脂組成物Ａ〜Ｆ及びコーン油を用いて、繰り返して天ぷら調理を行い、調理時の匂いの評価を行った。結果を表２に示す。
天ぷら調理の方法と評価方法は以下の通りである。

調理後の油は金属製オイルポットにとり、室温で保存し、２日おきに調理評価を実施した。
（評価方法）
パネラー１０名
調理時の匂い及び揚げた天ぷらの風味を下記の基準で５段階評価し、平均点（四捨五入）を求めた。
５；良い
４；やや良い
３；どちらとも言えない
２；やや悪い
１；悪い
【００１３】
【表２】

【００１４】
実施例７〜９、比較例２
実施例１、３、５及び比較例１にて、繰り返して天ぷら調理を行った際の、油脂のＣＯＶ（カルボニル価）を測定した。結果を表３に示す。
【００１５】
【表３】

【００１６】
実施例１０、比較例３
上記の如く調製した油脂組成物Ｆ及びコーン油を用いて、繰り返して唐揚げ調理を行い、調理時の匂いと唐揚げの風味の評価を行った。結果を表４に示す。
唐揚げ調理の方法と評価方法は以下の通りである。

調理後の油は金属製オイルポットにとり、室温で保存し、２日おきに調理評価を実施した。
（評価方法）
調理時の匂い及び揚げた唐揚げの風味を実施例１と同じ評価方法で評価した。
【００１７】
【表４】

【００１８】
実施例１１、比較例４
上記の如く調製した油脂組成物Ｆ及びコーン油を用いて、繰り返してヒレカツ調理を行い、調理時の匂いとヒレカツの風味の評価を行った。結果を表５に示す。
ヒレカツ調理の方法と評価方法は以下の通りである。

調理後の油は金属製オイルポットにとり、室温で保存し、２日おきに調理評価を実施した。
（評価方法）
調理時の匂い及び揚げたヒレカツを実施例１と同じ評価方法で評価した。
【００１９】
【表５】

[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an additive that suppresses deterioration of fats and oils during cooking by adding to fats and oils used for fried foods and fried foods.
[0002]
[Prior art and problems to be solved by the invention]
When fats and oils are heated during cooking, reactions such as decomposition and polymerization occur, and as a result, volatile substances are volatilized and an unpleasant odor peculiar to oil is generated. Especially when oil is used repeatedly for deep-fried foods, the smell becomes strong.
In order to solve this problem, the addition of an antioxidant or the like has been studied. For example, in JP-A-4-96992, an antioxidant composition comprising an antioxidant in a phospholipid and / or diglyceride. An edible oil composition excellent in oxidation resistance and high temperature resistance has been proposed, and Japanese Patent Application Laid-Open No. 4-226588 discloses a metal containing ascorbyl palmitate, tocopherol concentrate, and rosemary extract mixture. An edible oil composition to which an effective antioxidant composition is added even in the presence of minerals has been proposed, but the effect is not sufficient.
[0003]
[Means for Solving the Problems]
The present inventor has found an agent that reduces the smell (oiliness) peculiar to oil during cooking, enables comfortable cooking, and suppresses deterioration due to heating of the oil itself, and has completed the present invention.
That is, this invention relates to the deterioration inhibitor at the time of fats and oils heating which uses the compound represented by General formula (1) as an active ingredient.
[0004]
[Chemical 1]

[0005]
(In the formula, ^{two of} R ¹ , R ² and R ³ represent acyl groups derived from saturated or unsaturated fatty acids having 12 to 22 carbon atoms, and the remaining one represents a sugar residue.)
[0006]
DETAILED DESCRIPTION OF THE INVENTION
The compound represented by the general formula (1) used in the present invention is contained in food materials such as wheat flour, spinach and carrot, and may be a synthetic product or one extracted from the above food materials. As the extraction method, a method of extracting with hexane, acetone, chloroform, methanol, ethanol or a mixed solvent thereof can be used.
The sugar residue is a simple substance such as glucose, galactose, sucrose, lactose, maltose, O-α-galactopyranosyl- (1 → 6) -β-galactopyranose (hereinafter abbreviated as digalactose), glucosamine, galactosamine and the like. It is the residue of a sugar when one hydroxyl group of a sugar, disaccharide, or amino sugar is condensed with the hydroxyl group of glycerin to form an ether bond. Usually, the hydroxyl group at the first position of the sugar is bonded, but it may have a structure in which a hydroxyl group other than the first position is bonded.
It is preferable that 70% or more of the sugar residues are galactose residues or digalactose residues. The acyl group is preferably derived from an unsaturated fatty acid, and more than 70% of the acyl group is preferably a linoleoyl group.
[0007]
The fats and oils used in the present invention are not particularly limited as long as they are generally used edible oils, but naturally derived fats and oils such as safflower oil, olive oil, cottonseed oil, rapeseed oil, corn oil, soybean oil, palm Vegetable oils such as oil, sunflower oil and sesame oil are preferred. These fats and oils may be used alone or may be mixed as appropriate.
[0008]
In the present invention, the amount of the above compound added is 0.05 ppm or more, preferably 0.5 ppm or more, particularly preferably 1 ppm or more in the fat.
The compound of the present invention does not have an odor itself, and if it is added to fats and oils, for example, it is possible to provide fats and oils in which the COV of the fats and oils hardly rises even during cooking and hardly deteriorates. Although the details of the mechanism of action are unknown, this substance has a hydrophobic part and a hydrophilic part in one molecule due to its structure, and is present at the oil / air (oxygen) interface generated during cooking. / Presumed to suppress oxygen contact.
The effect increases for a long time as the amount added increases, but 1000 ppm or less is desirable from the point of flavor.
[0009]
Antioxidants, emulsifiers and the like can be added to the deterioration inhibitor of the present invention. Antioxidants include L-ascorbic acid palmitate and tocopherol, as well as extracts from natural products such as spices, tea, licorice and rosemary. Examples of the emulsifier include sucrose fatty acid ester, organic acid monoglyceride, polyglycerin fatty acid ester, phospholipid and the like. Depending on the purpose, various flavoring agents (flavors), nutrient enhancers, thickeners and the like can be added.
The fats and oils to which the deterioration inhibitor of the present invention is added are suitably used for cooking fried foods such as stir-fried vegetables and fried foods such as tempura and fried chicken.
[0010]
【Example】
As shown in Table 1, corn oil was blended with various additives to prepare oil and fat compositions A to F according to the present invention.
[0011]
[Table 1]

[0012]
* 1 Wako Pure Chemical Reagent (049-24911) (from spinach)
* 2 SIGMA reagent (D-4651) (derived from whole wheat flour)
* 3 Wako Pure Chemical Reagent (073-03951) (from spinach)
* 4 SIGMA reagent (G9523) (from whole wheat flour)
* 5 Digalactosyldiglycerol-containing fraction obtained from Sankyo Co., Ltd. carrot oil Sankyo through chloroform / methanol (2/1) silica gel chromatography and methanol-based ODS gel chromatography (containing about 80%)
* 6 Fraction containing digalactosyl diglycerol extracted from commercially available wheat flour (strong flour) with hexane / ethanol (2/1) system (containing approximately 30%)
Examples 1-6, Comparative Example 1
Tempura cooking was repeated using the oil and fat compositions A to F and corn oil prepared as described above, and the odor during cooking was evaluated. The results are shown in Table 2.
The method of tempura cooking and the evaluation method are as follows.

The oil after cooking was put in a metal oil pot and stored at room temperature, and cooking evaluation was carried out every two days.
(Evaluation methods)
Ten panelists cooked the odor and fried tempura flavor on a five-point scale according to the following criteria, and the average score (rounded off) was determined.
5; Good 4; Slightly good 3; Neither can be said 2; Slightly bad 1;
[Table 2]

[0014]
Examples 7-9, Comparative Example 2
In Examples 1, 3, 5 and Comparative Example 1, the COV (carbonyl value) of fats and oils when tempura cooking was repeated was measured. The results are shown in Table 3.
[0015]
[Table 3]

[0016]
Example 10 and Comparative Example 3
Using the oil and fat composition F and corn oil prepared as described above, deep-fried cooking was repeated, and the odor during cooking and the flavor of the deep-fried food were evaluated. The results are shown in Table 4.
The method of fried cooking and the evaluation method are as follows.

The oil after cooking was put in a metal oil pot and stored at room temperature, and cooking evaluation was carried out every two days.
(Evaluation methods)
The smell during cooking and the flavor of fried chicken were evaluated by the same evaluation method as in Example 1.
[0017]
[Table 4]

[0018]
Example 11, Comparative Example 4
Using the oil and fat composition F and corn oil prepared as described above, cooking was carried out repeatedly, and the odor during cooking and the flavor of the fillet were evaluated. The results are shown in Table 5.
The method of the fillet cooking and the evaluation method are as follows.

The oil after cooking was put in a metal oil pot and stored at room temperature, and cooking evaluation was carried out every two days.
(Evaluation methods)
The smell at the time of cooking and the deep-fried fillet were evaluated by the same evaluation method as in Example 1.
[0019]
[Table 5]

Claims (1)

The deterioration inhibitor at the time of fats and oils heating which uses the compound represented by General formula (1) as an active ingredient.

(In the formula, ^{two of} R ¹ , R ² and R ³ represent acyl groups derived from saturated or unsaturated fatty acids having 12 to 22 carbon atoms, and the remaining one represents a sugar residue.)