JPS58146252A - Butter flavor - Google Patents

Abstract

PURPOSE:Gamma- and delta- 12C saturated and unsaturated lactones are used as major components to provide a butter flavor. CONSTITUTION:Gamma-12C and delta-12C unsaturated and saturated lactones are used as major active ingredients for a butter flavor. These lactones are producted by dissolving pure or crude hydroxy-acid triglycerides in vegetable oil and heating the solution at about 100 deg.C for 15-90min to increase the amount of gamma- and delta-12C lactones or by collecting the part of hydroxy-acid triglyceride with a relatively high molecular weight and heating it at about 100 deg.C for 15-90min. The resultant butter flavor may be added as much to margarin or other food or may be dissolved in a food oil, then added to food.

Description

[Detailed description of the invention] It is.

Butter flavor refers to a substance that emits the aroma characteristic of butter, and because of this aroma, butter has a significantly better flavor than margarine and other fats and oils.

For this reason, research has been conducted to try to improve the quality of butter flavor by adding it to inexpensive oils and fats, but a satisfactory butter flavor has not yet been obtained.

Butter flavor has been expressed in many ways, and its main components are said to be lactones, methyl ketones, aldehydes, and free fatty acids, but the actual situation has not yet been confirmed.

Regarding the theory that it is a lactone, δ-tecalactone was confirmed in butter in 1956, and in 1962
In 2007, the existence of homologues of γ and δ lactones was reported. Further research has shown that lactone precursors exist in butter, and that the lactone precursors are γ and δ hydroxy acids bound to glycerol molecules, and the hydroxy acids have an ester bond at the α position of the glyceride. It is predicted that this is the case. However, no details are known about how hydroxy acid glycerides are related to butter flavor, and it is also unclear which lactones are most involved in butter flavor.

The present invention was made in response to the above circumstances, and as a result of many years of research to clarify the actual state of butter flavor and obtain a new butter flavor from hydroxy acid triglycerides, butter flavor can be obtained by ketonizing hydroxy acid triglycerides. The butter oil separated from butter contains hydroxy acids, which are γ and δ oxyacids, as flavor precursors, and these substances separate from triglycerides by heating and easily convert into intramolecular cyclic esters (lactones). ), and learned that differences in the production conditions have a significant effect on flavor. Therefore,
Hydroxy acid triglycerides are extracted from butter oil separated from butter, heated to produce lactones, and γ- and δ-C12 separated from the resulting lactones.
Lactone (however, C12 indicates the number of carbon atoms.Hereinafter, this representation will be used)
They discovered that - was strong and developed Butterfureno (-), which contains γ- and δ-C12 lactone as the main active ingredients.

The hydroxy acid triglyceride used in the present invention is an ester bond of a hydroxy acid and a fatty acid, and the hydroxy acid only needs to contain a straight chain with a carbon number of Cs-C1a, and the fatty acid can be a lipase. When decomposed, it mainly produces palmitic acid, stearic acid, and oleic acid, which can be produced using tar oil, saturated and unsaturated oxyacids, and various synthetic methods.

To explain an example of producing the hydroxy acid triglyceride of the present invention, butter such as salted butter or unsalted butter is first melted at the lowest possible temperature, and the supernatant liquid is filtered once to produce butter oil. Separation of the hydroxy acid triglyceride from the above-described filter oil can be carried out chromatographically. For example, a long and narrow silicic acid column is prepared, and two parts of the column are loaded with the dissolved binder oil. A bath agent such as a solution of diethyl ether petroleum ether is then added and adsorbed onto the silicic acid, and then a diethyl ether solution containing 1% methanol is added, and the hydroxy acid triglycerides are fractionated into the solution. It becomes eluted.

However, monoglycerides, diglycerides, and cholesterin are also included in this, so when purifying it, fill a long and narrow column with silicic acid for dry columns, and fill the column with the above-mentioned 1.
% methanol in diethyl ether, and dissolve and load the concentrate 111-11111 in diethyl ether, petroleum ether bath. When this column is developed with a mixed solution of equal amounts of diethyl ether and petroleum ether, the hydroxy acid triglyceride will develop at the top and the mono- and diglycerides will develop at the bottom, so if only the top is separated and extracted with diethyl ether, they will flow out. However, the resulting effluent still contains cholesterol, so the effluent was concentrated, and the concentrate 052 was dissolved in 1 ml of chloroform/methanol, loaded onto a Sephadex LH-60 (trade name) column, and chloroform By performing gel filtration with a mixture of equal amounts of and methanol, cholesterol can be separated and hydroxy acid triglyceride with a high purity of 95 to 100% can be obtained. However, although it is desirable that the hydroxy acid triglyceride used in the present invention has a high purity, any crude triglyceride having a purity of 30% or higher can be used.

In the production of lactone from hydroxy acid triglyceride, as mentioned above, since the hydroxy acid contains γ or δ, it is easily lactonized by heating and produces a fragrance. At this time, heating temperature and time are important. Now, dissolve the hydroxy acid triglyceride in corn (5) salad oil, heat it in a liquid paraffin bath at each temperature for 60 minutes, 80 minutes, 100 minutes, and 120 minutes. The production of lactone when the time is 0 to 120 minutes is determined from 1st to 4th.
As shown in the figure. However, the quantification of lactone was carried out according to the method of Wang.

From the results in Figures 1 to 4, it is clear that when heated at 60°C (Figure 1), all lactones produced are 15
The main lactones are δ-012 lactone, δ-014 lactone and γ-01z:1 unsaturated lactone, and heating at 80°C (Figure 2) results in a higher δ- Higher lactones such as 014 lactone and δ-C16 lactone increase. However, heating at 100°C (Fig. 3) is different from heating at 80°C or lower, and δ-C
12-16 lactones and γ-C12° unsaturated lactones increased with time and further increased to 120°C (Figure 4).
In this case, lactones of δ-C16 and δ-C14 increase,
The γ-012.1 unsaturated lactone is the one that decreases.

This indicates that lower lactones are lactonized at low temperatures, but are easily volatile and decomposed at high temperatures (6). Father, total production of lactone at each temperature i', f
As shown in FIG. 5, as can be seen from this figure, a large amount of lactone is produced by heating at 100°C.

From these results, Butterfrey (-) is strongest when heated at 100'C, and decreases before and after that, but comparing Figures 3 and 4, the total physiological amount of lactone is 1.OOoC
Since there is no significant difference between 120°C and 120°C, the amount of lactone produced itself does not control the bitter flavor, but the amount of lower lactones has a strong influence on the flavor, and γ- and δ-C12 It turns out that the higher the content of saturated and unsaturated lactones, the better.

In order to further clarify the above facts, hydroxy acid triglyceride was divided by gel filtration using Sephadex LH-60 (trade name), and as shown in Figure 6, A, H, and C were separated.
, IJ was divided into four fractions, each fraction was concentrated and heated at 100°C for 30 minutes, and a sensory test was conducted. Fraction A was found to have the strongest butter flavor.
Frac/yo/13 is followed by fractions C and 1]
I couldn't detect any bitter flavor.

Table 1 shows the amount of lactone produced for each fraction/fill.

Table 1 ◎1 time, δ8 is δ-C8 lactone, 1.2:1. li
The same applies to unsaturated.

◎The numerical value in the upper row indicates the amount of lactone (m9)'s per 17 hydroquinic acid triglycerides, and the numerical value in parentheses indicates the amount of lactone relative to the total amount of lactone.

As can be seen from the above table, the total of fraction B is 2.2
2 m9 and fraction 1)], 79 m? Although the difference is small and does not affect the butter flavor much, the results of sensory tests show that there is a large difference. This means that Fraction A and Fraction B with Nokturf contain γ-C10 lactones and δ-Ct compared to other fractions C11).

This is because there are many lower lactones such as lactone, γ-Cxz lactone, γ-C121 unsaturated lactone, and δ-C12 lactone, especially γ-0121 unsaturated lactone and δ-C12 lactone.

Furthermore, from the above solid line results, it is clear that during gel filtration of hydroxy acid triglycerides, those that elite quickly, that is, those that have a relatively large molecular weight, produce a large amount of lactone and have a strong butter flavor.

From the above, it can be concluded that the butter flakes of the present invention have γ-C
The main active ingredient is 121 unsaturated and saturated δ-C12 lactone. These lactones can be produced by dissolving refined or crude hydroxy acid triglycerides in vegetable oil, etc., and heating them at a temperature of around 100°C for 15 to 90 minutes to increase the amount of γ and δ-C12 lactones, or Triglyceride (9) It can be produced by collecting relatively large molecular weight portions of Lido and heating them at a temperature of around 100°C for 15 to 90 minutes.

Moreover, it may be manufactured by various synthetic methods.

The butter flavor produced in this way is
It may be added to margarine and other foods, or it may be dissolved in edible oil or the like and added deeply to the food, and by adding it, the food will have a butter flavor.

As described above, the present invention has discovered the existence of γ-C12:l unsaturated lactone, which was previously unknown as a main component of butter, and has found that γ- and δ-CL2 saturated and unsaturated lactones are the main active ingredients. It was completed by adding a butter flavor.

The butter flavor of the present invention can be produced from any kind of butter, and can be produced stably at low cost since it can be synthesized using defective butter that does not meet the specifications or by various synthesis methods.

Furthermore, since it is obtained from a natural product, it is safe and has an extremely strong aroma, so adding a small amount can significantly improve the flavor of foods.

This will be explained below using one example.

Example 1 Commercially available butter 2002 was melted in a water bath at 40-50°C, the top surface was filtered through a piece of dry paper, and butter oil 165% was melted. I got i'.

Next, 100 f'i of the above butter oil was placed in a column filled with Mallinckrodt Kei [1 (too mesh)].
1. From above, 5% and 8% dimethyl ether in petroleum ether were passed in that order, and then 1% methanol in diethyl ether.5. OOQmg was passed through.

Concentrate the 1% methanol diethyl ether that flowed out,
The concentrate 17 was dissolved in 1 ml of diethyl ether/petroleum ether solution, loaded with silicic acid for a 100 cm long dry column, and developed with a 1:L solution of diethyl ether:petroleum ether. Upper part after deployment 20~50 crn
Collect 1 portion of diethyl ether 1. ．． Extracted at 00 me. ” The extract of the second category is concentrated and its 500m!
Dissolve li' in 1ml of Kuro-Meta bath solution and make a total length of 110cm.
rrL Sephatex LH-60 (trade name) and gel filtration with a chloroform:methanol 1:1 solution to obtain hydroxy acid triglyceride 430 with a purity of 80%.
f'lir separated. Next, 200 m9 of hydroxy acid triglyceride was loaded onto a 180 cm0 column of Sephatex LH-60 (trade name), and a 1:1 chloroform:methanol solution was added to the fracunion Ai shown in Figure 6.
(8 m9 of hydroxy-branched triglycerides). This was heated at 100°C for 30 minutes to obtain 0.024ml of butter flavor containing δ-C12 lactone as the main active ingredient.

0.02 m9 of this butter flavor to 100 m of margarine
? It was possible to create margarine with a flavor similar to butter.

[Brief explanation of drawings]

Figure 1 shows the formation of lactones from hydroxy acid triglycerides upon heating at 60°C, Figure 2 shows the formation of lactone Ω upon heating at 800°C, Figure 3 shows the formation of lactones at 100'C, and Figure 4 shows the formation of lactones at 120'C. shows. FIG. 5 shows the total amount of lactone produced when a hydroxy acid is heated at valley temperature. Figure 6 shows Sephatex LH
Fig. 6 shows the flow pattern of hydroxy acid triglyceride by -60 (trade name). l-160120 m1n ○ 60
120in breeding 3 no 1 bee 47! I 1n

Claims (1)

[Claims] (1) Butter flavor containing γ- and δ-C12 saturated and unsaturated lactones as main active ingredients.