JPS61288A - Water-soluble antioxidant - Google Patents

Abstract

PURPOSE:To provide a water-soluble antioxidant having an excellent effect, consisting of a cyclodextrin inclusion compd. of a tocol derivative. CONSTITUTION:A tocol derivative (pref. tocol having no phytol, e.g. alpha-tocopherol) and cyclodextrin (e.g. alpha-cyclodextrin) are dissolved in a solvent (e.g. dimethyl sulfoxide or N-methyl-2-pyrrolidone) with stirring, and the solvent is then removed by evaporation, etc., thus obtaining a cyclodextrin inclusion compd. of a tocol derivative. The inclusion compd. is useful as a water-soluble antioxidant for preventing oxidation of foods, fading of dyes and deterioration of plastics.

Description

[Detailed description of the invention] [Technical field of invention] This invention relates to water-soluble antioxidants.

[Prior art]

Conventionally, antioxidants have been widely used to prevent the oxidation of oils and fats, to prevent the deterioration of plastics, and to prevent the fading of dyes. But most of them.

It is oil-soluble, and to prevent the fading of water-soluble dyes and the deterioration of water-soluble plastics, only those with low antioxidant ability such as ascorbic acid have been used.

[Summary of the invention]

This invention was made in order to eliminate the drawbacks of the conventional products mentioned above, and by using a product containing a cyclodextrin clathrate compound of tocol derivatives, it has excellent antioxidant ability. The purpose is to provide water-soluble antioxidants.

[Embodiments of the invention]

Two examples of tocol derivatives related to this invention are α
-Tocopherol, β-tocopherol.

γ-tocopherol, δ-tocopherol, 5゜1-dimethyltocol, T-methyltocol, 5-methyltocol, tocol, α-tocotrienol, β-tocotrienol, γ-tocotrienol and δ-tocotrienol, among others, phytol This is to use a tokor without.

This is preferable because the inclusion rate becomes high.

As the cyclodextrin related to this invention.

Examples include t-cyclodextrin, α-cyclodextrin, β-cyclodextrin and r-cyclodextrin.

In order to obtain the water-soluble antioxidant of the present invention using the above composition, for example, the above-mentioned tocol derivative and cifurobukis) are dissolved in a solvent that dissolves both, and then the solvent is removed. use Such solvents include, for example, dimethylsulun oxide,
Examples include N-methyl-2-pyrrolidone and dimethylformamide.

This invention will be described below with reference to Examples, but the invention is not limited thereto.

Example 1 1 part by weight of β-cyclodextrin and 1 part by weight of α
- Tocopherol was dissolved in 100 parts by weight of dimethyl sulfoxide and stirred for a while.

Evaporate the dimethyl sulfoxide on a rotary evaporator. Dissolve this in 100 parts by weight of water and
Centrifuge at 500 x g for 10 minutes at ℃, remove the supernatant, and use the water-soluble antioxidant of one embodiment of this invention: □
Yu1□6□1i, yoyo, 3゜e□. - shows the ultraviolet absorption spectrum of an aqueous solution of the water-soluble antioxidant. According to this, it can be seen that α-tocopherol is water-soluble based on its characteristic absorption.

Separately, methylene blue (5~) was dissolved in 100 mt of water to obtain a methylene blue aqueous solution. When 0.5 mA of the above methylene blue aqueous solution and 2.5 mt of the above α-tocopherol-β-cyclodextrin clathrate aqueous solution of an embodiment of the present invention are added to a 1-day spectroscopic measurement cell, the absorption maximum of methylene blue is 660nm
What is the absorbance at 1C?

It was 065.

Figure 2 is a photobleaching curve diagram of methylene blue, and (a) in Figure 2 shows the addition of the α-tocopherol-β-cyclotextrin clathrate compound to the methylene blue aqueous solution at an ultra-high pressure of 150+nw/α2. It is a photobleaching curve showing the change in absorbance at 660 nm Kb depending on the irradiation time (minutes) when irradiated with mercury lamp light. Although not shown in Figure 1, when the irradiation time was 180 minutes, the absorbance at 650 nm was #'io, ss.

Example 2 1 part by weight α-cyclodextrin and 0.5 part by weight β
- Dissolving tocopherol in 100 parts by weight of N-methyl-2-pyrrolidone and using a rotary evaporator,
Evaporate the N-methyl-2-pyrrolidone. Dissolve this material in 100 parts by weight of water, and add 1 soooxg at 10°C.
Centrifuge for 0 minutes and remove the supernatant to obtain a water-soluble antioxidant according to another example of the present invention. Next, 0.5 mA of the methylene blue aqueous solution used in Example 1 and 15 mA of the β-tocopherol-α-cyclodextrin clathrate aqueous solution of other examples of the present invention were placed in a 1 cm spectroscopic cell. The absorbance of this material at 660 nmK was 0.65. Furthermore, the methylene blue aqueous solution K to which the β-tocopherol-α-cyclodextrin clathrate compound was added.

When irradiated with ultra-high pressure mercury lamp light of 150 mvr/2 for 45 minutes, the absorbance reached 0.62.

Comparative Example The methylene blue aqueous solution used in Example 1 [1.5 mt and 2.5 mt of distilled water were added to ICII! When added to a spectroscopic measurement cell, the absorbance at 660 nm was 0.65. 150 mw/am to this methylene blue aqueous solution
A photobleaching curve showing the change in absorbance at seonm depending on the irradiation time (minutes) when irradiated with ultra-high pressure mercury lamp light of No. 2 is shown in curve color in FIG.

As shown in the above Examples and Comparative Examples, it was confirmed from FIG. 1 that the cyclodextrin clathrate compound of the tocol derivative of the Example of this invention is water-soluble. Moreover, as shown in Figure 2.

The photobleaching reaction rate constant obtained from the photobleaching curve (a) of the methylene blue aqueous solution to which the above-mentioned clathrate compound of one embodiment of the present invention was added is = 1.4 x 10-3 min-1, and the photobleaching curve of the methylene blue aqueous solution. (b), the reaction rate constant for photobleaching ==IIX10-3! olin
'Comparing with ', it is busy to add the clathrate compound of the embodiment of this invention, F! A: It is clear that it has an antioxidant effect.

Note that the photobleaching shown in the Examples is due to singlet oxygen produced by methylene blue with light, and it is thought that the tocol derivative prevents the discoloration by erasing this. Further, in the examples, the prevention of color fading of dyes, particularly methylene blue, was described, but other dyes have similar effects, and furthermore, they are also effective in preventing deterioration and oxidation of other materials.

〔Effect of the invention〕

As explained above, the present invention uses a tocol derivative containing a cyclodextrin clathrate compound, thereby making it possible to obtain a water-soluble antioxidant with excellent antioxidant ability. It is useful for preventing the deterioration of plastics and the oxidation of foods, etc.

[Brief explanation of the drawing]

FIG. 1 shows α-tocopherol in one embodiment of the present invention.
FIG. 2 is an ultraviolet absorption spectrum diagram of an aqueous solution of a β-cyclodextrin clathrate compound, and is a photobleaching curve diagram showing the effect of adding the clathrate compound in an example of the present invention. 1 In the figure, (a) is a photobleaching curve of a methylene blue aqueous solution when the clathrate compound of the example of this invention is added. (b) Photobleaching curve of H methylene flu aqueous solution. Figure 1 Mihide length (/nuriu)

Claims (2)

[Claims] (1) A water-soluble antioxidant containing a cyclodextrin clathrate compound of a tocol derivative. (2) The water-soluble antioxidant according to claim 1, wherein the tocol derivative is α-tocopherol.