JPS58201948A - Powdery egg yolk oil and powdery egg yolk lecithin and their preparation - Google Patents

Abstract

PURPOSE:To prepare powdery egg yolk oil and powdery egg yolk lecithin having improved stability and handleability, by selectively hydrogenating the phospholipid fraction of egg yolk oil and egg yolk lecithin. CONSTITUTION:Powdery egg yolk oil and powdery egg yolk lecithin having an iodine value of <=30 can be prepared by (1) dissolving 10-60wt% of egg yolk oil having a phospholipid content of <50% and egg yolk lecithin having a phospholipid content of >=50% and free from oxidation and browning in a >=3C alcohol solvent (e.g. isopropyl alcohol), (2) hydrogenating the solute under a hydrogen pressure of >=2kg/cm<2>G at 50-95 deg.C in the presence of anhydrous platinum group-metal catalyst to reduce the iodine value of the phospholipid fraction to <=10, (3) filtering the reaction product to remove the catalyst, (4) concentrating under reduced pressure to remove the solvent, and (5) crushing and drying the residue.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides powdered egg yolk oil and powdered egg yolk lecithin, which are characterized by containing a phospholipid class with an iodine value (hereinafter abbreviated as 1, V) of 10 or less, and their powdered egg yolk lecithin. Regarding the manufacturing method.

Egg yolk oil and egg yolk lecithin as used in the present invention refer to a mixture of neutral fat derived from egg yolk, phospholipids, and other complex lipids. Furthermore, in the present invention, egg yolk oil refers to an oil with a phospholipid content of less than 50 t, and primary egg yolk lecithin refers to an oil containing 50 t or more.

Egg yolk oil and egg yolk lecithin (hereinafter collectively referred to as egg yolk oil) have long been used as naturally-derived emulsifying humectants that have various beneficial effects, including surfactant effects, due to the action of the phospholipids and cholesterol they contain. It has been used since. For example, pharmaceuticals include skin dermatitis treatments, topical hemorrhoid medications,
It is used as a cardiotonic medicine, and in cosmetics as a cream additive and a lip spread improver, and as a moisturizer and lubricant that gives a moist and supple feeling. In food products, it is used as an anti-splatter agent for margarine and to improve the physical properties of ice cream.

However, the actual amount of egg yolk oil used in these products is about 0.1 to 0.3%, and it is rare for more than 1 yolk oil to be used. The reason for this is, as is well known, that phospholipids, which are the main components of egg yolk oil, are easily oxidized and are extremely unstable and prone to browning. For example, when used as a raw material for cosmetics, it is disadvantageous in that it undergoes oxidative browning over time and begins to emit an amber odor.

This oxidation occurs when unsaturations in the fatty acid side chains of phospholipids, such as phosphatidylcholine and phosphatidylethanolamine, especially conjugated double bond sites, are damaged by heat, light, etc.
Under the influence of metal and pH, it is peroxidized and a carbonyl group is generated. Furthermore, it is believed that this carbonyl group causes a complicated condensation polymerization with the primary amino group of phosphatidylethanolamine, gradually causing polymerization and decomposition, resulting in coloration and odor generation.

From this background, in order to prevent the deterioration of egg yolk oil and to utilize the surfactant effect of phospholipids, it is considered to be a good idea to minimize the number of unsaturated sites, which are the starters for deterioration, among various improvements. .

Elimination of this unsaturated portion, ie, hydrogen reduction, is the solution. When this reduction reaction is carried out, the product is a naturally occurring product and there is no risk of creating a completely synthetic product.

There were a few attempts to hydrogenate egg yolk lecithin in the early part of this century.

However, this is made by dissolving only reddish-brown phospholipids that do not contain neutral lipids in ethanol and then hydrogenating the solution. This method has been used to identify phospholipids. However, since the lecithin is already reddish-brown in color, the obtained lecithin is considered to be browned, and it does not necessarily provide a clear industrial method.

In addition, with the mixture of phospholipids and neutral lipids that is the object of the present invention, hydrogenation has not yet been carried out, and when ethanol is used as described later, the neutral elastic segment cannot be dissolved. It is impossible to do so.

As a result of intensive research in order to improve the disadvantages such as easy browning as mentioned above, the present inventors applied conventional hydrogenation to egg yolk oil and improved it, thereby increasing the phospholipid class, which is an active ingredient. By selectively hydrogenating and reducing I and V to 30 or less, we succeeded in producing an extremely stable and white powdered egg yolk oil, leading to the completion of the present invention.

The method of the present invention will be described below.

As mentioned above, the egg yolk oil used in the present invention is a mixture of neutral lipids and phospholipids derived from egg yolks, and in order to obtain the desired white powdered egg yolk oil, it is necessary to use an egg yolk oil that does not undergo oxidative browning. It is preferable to obtain oil that is browner and smells better than browned egg yolk oil.

Next, the solvent used when hydrogenating this egg yolk oil is preferably an alcohol, but if methanol or ethanol is used, especially when the phospholipid concentration in the egg yolk oil is less than 40 moss, the solvent is neutral because the amount of phospholipids is small. Lipids cannot be solubilized in alcohol, so if an alcohol with C3 or higher, such as isopropyl alcohol, is used, neutral lipids can be easily dissolved due to their ability to dissolve neutral lipids at high temperatures (4). This advantage is also exhibited in the filtration process excluding the catalyst, and it is desirable to use an alcohol of C1 or higher such as isopropyl alcohol.

Further, the dissolved concentration is 10 to 60 Chi w/w, preferably 20 to 50 Chi.

Hydrogenation is carried out at 50~ to suppress phospholipid deterioration during the reaction.
The temperature is preferably 95°C, preferably 65 to 85°C, and the hydrogen pressure Fi is 2 Yu/c! IG or higher, preferably 7 Yu/dG
The catalyst may be an anhydrous platinum metal catalyst to prevent water absorption into the phospholipid, but a nickel-based catalyst is poisonous and serves no purpose.

Following catalytic filtration, vacuum concentration is performed to recover alcohol from the hydrogenated solution. At this time, in order to make the powdered egg yolk oil more white, it is preferable to recover the solvent at a temperature of 75°C or lower, preferably 65°C or lower.

The obtained hydrogenated egg yolk oil is pulverized in a state containing several thiols, and then dried at 40° C. or lower, whereby the solvent can be completely removed without damaging the quality.

The powdered egg yolk oil obtained in the above manner is used in the following experimental example VCM.
Amazingly, despite the simultaneous hydrogenation of neutral lipids and phospholipids, the phospholipid segment is selectively hydrogenated, dramatically improving stability and usability compared to conventional egg yolk oil. I understand that.

Experimental example Egg yolk oil that has not been oxidized or browned (moisture 0.5%, +7 lipids 27.0%, peroxide value Omeq/9) 5
Add and dissolve 700 ml of isopropyl alcohol to 00V. Then 1Q% Pd-Charcoal 9
f was added and transferred to a hydrogenation apparatus. Hydrogen pressure 7 to 9/
cdG.

Under the condition that the liquid temperature was 65° C., cumulative addition of tap water was carried out, and the reactants were sampled at 20, 40°, 60, 80, and 100 minutes.

The ramped reactants, excluding the p-filter catalyst, are -
The solvent was removed using an evaporator.

Each of the obtained powdered egg yolk oils was fractionated into neutral lipids and phospholipids using silica gel.

The results of measuring I and V of each component were as follows.

Table 1 Iodine value (I, V,) measurement results for each reaction product Next, the powdered egg yolk oil for each reaction time was placed in a ventilation dryer at 75°C and a rapid accelerated deterioration test was conducted.The results are shown in Table 2. I got it.

□ Table 2 Results of rapid accelerated deterioration test * Unhydrogenated * * Dissolve powdered egg yolk oil 11 in chloroform and 25fn
Measure the absorbance as t.

As described above, the effects of adding the powdered egg yolk oil of the present invention to foods, cosmetics, medicines, etc. are as follows. Conventionally, only 0.1 to 0.2 g could be added due to lack of oxidation stability, but the present invention Therefore, it is possible to add a sufficient amount to be effective as a surfactant, and in this case, there is no fear of quality deterioration. - It is clearly shown in the above experimental examples that this objective can also be achieved by partial hydrogenation, since the phospholipid fraction, which is particularly susceptible to damage, is selectively hydrogenated.

Secondly, since the color changed from yellow to white, the color of the base does not change due to addition, and the most desirable color can be selected.

Thirdly, since eggs do not have a beef odor, they do not affect the flavor or fragrance of foods or cosmetics.

Finally, 1. Since the phospholipid is in a powder form, the weighing and dissolving process has been greatly improved compared to waxy phospholipids.

Examples of the present invention will be shown below.

Example 1 Add 1200 m of isopropyl alcohol to 500 f of egg yolk oil that has not been oxidized or browned (moisture 0.7%, phospholipid 26.2%, iodine value 77 (f/1009), peroxide value omeQ/M), Keep at 50°C for 20 minutes to dissolve. Next, 152 of 1096 Pd-Charcoal (dry product) was added, and the mixture was placed in a 5-volume hydrogenation autoclave. Hydrogenation was performed at a hydrogen pressure of ykg/aia and a liquid temperature of 65°C. The reaction time was 60 minutes, and stirring was performed using a turbine blade at 70 rpm. After the reaction was completed, residual hydrogen gas was discharged into the atmosphere, N and a pressure of 1 kg/dG were applied to the reaction solution, and the catalyst was removed by pressure filtration. The resulting clean solution was then concentrated under reduced pressure to recover the solvent. At this time,
Collection was completed at a liquid temperature of 65° C. (reduced pressure of 150,111 g).

The dissolved hydrogenate was poured into a tray and cooled to room temperature. The product in the tray was further crushed into 6 mesh baths, and the solvent was completely removed by drying with hot air at 40°C to obtain a white powdered egg yolk oil. Yield 475f, moisture 0.8%,
Phospholipid 26.5t, iodine value 20 (f/100f)
Atatsu nine.

Example 2 Egg yolk oil that is not oxidized or browned (same as Example 1) 3
Add 700 g of isopropyl alcohol to 00f and make 50
Next, keep at ℃ for 20 minutes to dissolve. Then 10% Pd-
Charcoal 15 f was added and placed in a 2-volume hydrogenation autoclave. Hydrogenation was carried out for 2 hours at a hydrogen pressure of 80 ky/cda and a liquid temperature of 65 to 90°C.

Stirring was performed at 800 rpm. After the reaction was completed, it was treated in exactly the same manner as in Example 1 to obtain a 282f tube of powdered egg yolk oil. Moisture 0.6%, phospholipid 26.4%, iodine value 2.0
(f/100 f).

Example 3 750 d of isopropyl alcohol was added to 200 f of egg yolk lecithin (moisture 1.0 t, phospholipid 68.0 t, peroxide value Omeq/Yu, iodine value 72 (r/100f)) that was not oxidized or browned, and 50 g of isopropyl alcohol was added. Dissolve at ℃ 20 minutes. −
Next, 50% Pd-Charcoal 12f was added and placed in a 5% hydrogenation autoclave. Hydrogenation was carried out for 45 minutes at a hydrogen pressure of 7 to 9/cl1G and a liquid temperature of 65° C. (700 rpm). Powdered egg yolk lecithin 189f was obtained by the same treatment as in Example 1. Moisture 1.
1%, phospholipid 68.29G, iodine value 23.0
(f/100).

Example 4 Highly purified egg yolk lecithin that is not oxidized or browned (moisture 1.2
H, phospholipid 92.0 H, peroxide value o meq/9
, iodine value 71 (f/100f )) 250 flf
c Add isopropyl alcohol 500- and heat at 5Q℃ for 2
Stir and dissolve for 0 minutes. 10% Pd-Charcoa
7.5 t was added and 2 t was placed in the autoclave.

At hydrogen pressure bokg/dtG, liquid temperature 70-90℃, 12
Hydrogenation was carried out for 0 minutes (1000 rpm).

Powdered egg yolk lecithin 229? was processed in the same manner as in Example 1.
I got it. Water content is 1.5%, phospholipid content is 91.8%, and iodine value is 1.7 (f/1009).

Claims (4)

[Claims] (1) Powdered egg yolk oil and powdered egg yolk lecithin with an iodine value of 30 or less, which are characterized by containing a phospholipid segment with an iodine value of 10 or less. (2) Iodine value 3, characterized by selectively hydrogenating the purine lipid fraction of egg yolk oil and egg yolk lecithin that have not been oxidized or browned to bring the phospholipid fraction to an iodine value of 10 or less.
0 or less powdered egg yolk oil and powdered egg yolk lecithin. (3) The method for producing powdered egg yolk oil and powdered egg yolk lecithin according to claim 2, wherein an alcohol of Cs or higher is used as a solvent for egg yolk oil and egg yolk lecithin that are not oxidized or browned. (4) The method for producing powdered egg yolk oil and powdered egg yolk lecithin according to claim 2, wherein the hydrogenation is carried out at 95°C or lower, and the alcohol at the hydrogenation edge is recovered at 75°C or lower.