JP5608546B2 - Antioxidant - Google Patents

Description

  The present invention relates to an antioxidant.

  In recent years, there has been a strong interest in the damage of biomolecules, membranes and tissues caused by free radicals and active oxygen, and various diseases derived therefrom. Examples of reactive oxygen species include superoxide, hydroxy radical, hydrogen peroxide, and singlet oxygen. Among them, superoxide and hydroxy radical are radical species, and hydroxy radical is particularly known as a highly reactive free radical. ing. It has been found that these reactive oxygen species are closely involved in various skin diseases such as inflammation, skin darkening, DNA damage, aging such as spots and wrinkles (Non-patent Document 1).

  As antioxidants that eliminate reactive oxygen species, for example, ascorbic acid, carotenoids, uric acid, vitamin E, flavonoids and the like are known. Among them, dimethyl dimethyl is a highly reactive antioxidant having a hydroxyl radical scavenging ability. Although sulfoxide (DMSO), thiourea, mannitol, sorbitol, xylitol and the like are known (Patent Documents 1 and 2 and Non-Patent Document 2), they cannot always be said to have sufficient effects.

  The present inventors have found that isosorbide has a wrinkle improving effect (Patent Document 3). However, no investigation has been made on the antioxidant action of other anhydrous sugar alcohols.

JP 61-502821 gazette JP 2008-266203 A International Publication No. 2006/115191 Pamphlet

Miyaki Yoshiki, “Fragrance Journal, Vol. 11,” published by Fragrance Journal, November 15, 1993, p. 12-17 Tetsuo Nagano, “Pharmacia Vol. 27, No. 3”, published by the Japanese Pharmaceutical Association, February 10, 1991, p. 231-233

  The subject of this invention is providing the more superior antioxidant.

  As a result of intensive studies in view of the above circumstances, the present inventors have found that an anhydride of a sugar alcohol having a carbon number of 4 has an excellent antioxidant ability and is useful as an antioxidant for external skin preparations or food and beverage compositions. As a result, the present invention has been completed.

  That is, this invention provides the antioxidant which uses the C4 anhydrous sugar alcohol represented by the following Formula (1) as an active ingredient.

  Moreover, this invention provides the skin external preparation and food-drinks composition containing the C4 anhydrous sugar alcohol represented by the said Formula (1).

  The anhydrous sugar alcohol of the present invention is an antioxidant having excellent hydroxyl radical scavenging ability and excellent safety and stability. Therefore, the skin external preparation and food / beverage product composition containing the same can be expected to have an effect of preventing / suppressing inflammation, skin darkening, DNA damage, aging such as spots and wrinkles.

  The active ingredient of the antioxidant of the present invention is an anhydrous sugar alcohol having 4 carbon atoms represented by the formula (1). Examples of the anhydrous sugar alcohol include anhydrous erythritol, anhydrous threitol and the like, which can be synthesized from sugar alcohol and the like by a known method, and are commercially available from Tokyo Chemical Industry Co., Ltd. or Finetech Industry Co., Ltd. Things can also be used.

  The anhydrous sugar alcohol represented by the formula (1) has excellent antioxidant ability, particularly excellent hydroxy radical scavenging ability, as shown in Examples below. The antioxidant capacity is significantly superior to erythritol. Therefore, the anhydrous sugar alcohol represented by Formula (1) can be mix | blended with a skin external preparation and food-drinks composition as an antioxidant.

  The anhydrous sugar alcohol of the present invention can be used as it is as an antioxidant. Furthermore, it can also be used in combination with known antioxidant components such as ascorbic acid, vitamin E, and polyphenol compounds within a range not impairing the effects of the present invention.

  In the present invention, the anhydrous sugar alcohol represented by the formula (1) can be used as an antioxidant added to skin external preparations such as pharmaceuticals, quasi drugs, and cosmetics. The cosmetic is not particularly limited, and examples thereof include skin cosmetics, foundations, makeup cosmetics such as lipsticks, and bathing agents. Moreover, it does not restrict | limit especially as a dosage form, For example, it can be set as an ointment, a lotion, an emulsion, a cream, a pack, a granule, a cataplasm etc.

  The content of the anhydrous sugar alcohol represented by the formula (1) in the external preparation for skin is preferably 0.001 to 10% by mass (hereinafter simply referred to as%) based on the total amount of the external preparation for skin, More preferably, it is 0.01-5%, More preferably, it is 0.1-4%. If it is in these ranges, anhydrosugar alcohol can be mix | blended stably and a high antioxidant effect can be exhibited.

  In addition, in addition to the above, coloring agents, perfumes, preservatives, surfactants, pigments, and the like can be appropriately added to the external preparation for skin of the present invention within a range in which the object of the present invention is achieved.

  In the present invention, the anhydrous sugar alcohol represented by the formula (1) can be used as an antioxidant added to ordinary food and beverage compositions including pharmaceuticals, quasi drugs and health foods. . The dosage form of the food / beverage composition is not particularly limited and can be various. Specifically, tablets, pills, sugar-coated tablets, powder, granules, fine granules, tea, tea packs, Hard capsules, soft capsules, drinks and the like can be used.

  The content of the anhydrous sugar alcohol represented by the formula (1) in the food or drink is preferably 0.001 to 10%, more preferably 0.01 to 5%, based on the total amount of the food or drink composition. More preferably, it is 0.1 to 4%. If it is in these ranges, the anhydrous sugar alcohol of this invention can be mix | blended stably and a high antioxidant effect can be exhibited.

  In addition to the above, excipients and the like are appropriately added to the food / beverage product composition of the present invention, and it can be made into dosage forms such as powder, fine granules and granules according to known techniques.

  EXAMPLES Hereinafter, although this invention is explained in full detail based on an Example and a comparative example, the technical scope of this invention is not restrict | limited by them.

Example 1 (Evaluation of antioxidant power)
According to the following method, the antioxidant power of anhydrous erythritol was measured as hydroxy radical scavenging ability. Anhydrous erythritol was manufactured by Tokyo Chemical Industry Co., Ltd. In addition, mannitol, erythritol, and threitol were used as comparative compounds.
(1) KH ₂ PO ₄ aqueous solution (50 mmol / L) 0.4 mL, test compound 0.1 mL, EDTA aqueous solution (1.04 mmol / L) 0.1 mL, iron chloride aqueous solution (1 mmol / L), ascorbic acid aqueous solution (1 mmol / L) 0.1 mL, deoxyribose aqueous solution (28 mmol / L) 0.1 mL, and hydrogen peroxide (10 mmol / L) 0.1 mL were mixed and kept at 37 ° C. for 1 hour.
(2) After 1 hour, 1 mL of a 20% trichloroacetic acid aqueous solution and 0.5 mL of a 0.67% thiobarbituric acid aqueous solution were added and held in a boiling water bath for 10 minutes.
(3) After 10 minutes, the mixture was allowed to cool, and the absorbance (532 nm) was measured. The measurement results are shown in Table 1.

Hydroxy radical scavenging rate (%) = [[(CD)-(AB)] / (CD)] × 100
A: Absorbance when test compound is added B: Absorbance when hydrogen peroxide is changed to water C: Absorbance when test compound is changed to water D: Absorbance when test compound and hydrogen peroxide are changed to water

  From Table 1, it can be seen that anhydrous erythritol according to the present invention has significantly superior hydroxy radical scavenging ability than mannitol, erythritol and threitol.

  A skin external preparation and a food / beverage product composition containing the antioxidant of the present invention having the following composition were produced by conventional methods (Examples 2 to 8). In any case, no problem was found in the blending characteristics. In addition, all compounding quantities are mass%.

Example 2 (milky lotion)
(Blending ingredients) (Blending amount)
Anhydrous erythritol (Tokyo Chemical Industry Co., Ltd.) 5.0
Bentonite 0.5
Glyceryl monostearate 1.0
Stearic acid 0.5
Behenyl alcohol 0.3
Cholesterol 0.3
Vaseline 0.5
Liquid paraffin 10.0
Methyl polysiloxane 1.0
Concentrated glycerin 10.0
Dipropylene glycol 10.0
N-stearoyl-sodium L-glutamate 0.2
Xanthan gum 0.3
Ascorbic acid 2-glucoside 2.0
Dipotassium glycyrrhizinate 0.2
Nicotinamide 1.0
N-acetylglucosamine 0.1
N-methyl-L-serine 0.1
Oat extract 0.2
Kyonin extract 0.1
Yeast extract 0.1
1,2-octanediol 0.2
Phenoxyethanol 0.1
Purified water residue

Example 3 (skin lotion)
(Blending ingredients) (Blending amount)
Anhydrous erythritol (Tokyo Chemical Industry Co., Ltd.) 0.5
Glycerin 10.0
1,3-butylene glycol 6.0
Ethanol 8.0
Polyoxyethylene hydrogenated castor oil (60 EO) 0.5
Ascorbic acid 1.0
Citric acid 0.1
Sodium citrate 0.3
Purified water residue

Example 4 (Cream)
(Blending ingredients) (Blending amount)
Anhydrous Threitol 0.2
(Finetech Industry)
Anhydrous erythritol (Tokyo Chemical Industry Co., Ltd.) 1.0
Stearic acid 5.0
Stearyl alcohol 5.0
Glyceryl tri-2-ethylhexanoate 10.0
Macadamia nut oil fatty acid cholesteryl 4.0
Dl-α-tocopherol acetate 0.2
Glyceryl monostearate 3.0
Dipropylene glycol 10.0
1,2-hexanediol 1.0
Potassium hydroxide 0.2
Phenoxyethanol 0.3
Methylparaben 0.1
Perfume Appropriate amount of purified water

Example 5 (cream)
(Blending ingredients) (Blending amount)
Anhydrous Threitol 2.0
(Finetech Industry)
Olive Squalane 10.0
Palmitic acid 2.0
Hydrogenated palm kernel oil 0.3
Macadamia nut oil 0.2
Medfoam oil 0.2
Jojoba oil 0.1
Apricot kernel oil 0.1
Hydrogenated soybean phospholipid 0.2
Cetanol 3.5
Glyceryl monopalmitate 2.0
Concentrated glycerin 10.0
Phenoxyethanol 0.1
Carboxyvinyl polymer 0.2
Potassium hydroxide 0.2
Purified water residue

Example 6 (Sunscreen)
(Blending ingredients) (Blending amount)
Anhydrous erythritol (Tokyo Chemical Industry Co., Ltd.) 0.5
Anhydrous Threitol 3.0
(Finetech Industry)
Methyl polysiloxane (1.5 mm ² / s) 1.0
Methyl polysiloxane (2.0 mm ² / s) 2.0
Methyl polysiloxane (6.0 mm ² / s) 1.0
Methylphenylpolysiloxane 2.0
Methylcyclopolysiloxane 4.0
Tris (trimethylsiloxy) methylsilane 4.0
Polyoxyethylene / methylpolysiloxane copolymer 2.0
Isododecane 1.0
Isohexadecane 2.0
Liquid isoparaffin 2.0
Isononyl isononanoate 5.0
Squalane 1.0
2-Ethylhexyl paramethoxycinnamate 5.0
Dimethyl distearyl ammonium hectorite 1.0
Zinc oxide 10.0
Titanium oxide 5.0
1,2-butanediol 1.0
Phenoxyethanol 0.3
Pure water residue

Example 7 (fruit juice drink)
(Blending ingredients) (Blending amount)
Anhydrous erythritol (manufactured by Tokyo Chemical Industry Co., Ltd.) 2.0
Anhydrous Threitol 1.0
(Finetech Industry)
Sorbitol 1.0
Xylitol 1.0
Fragrance 1.0
Apple juice remaining

Example 8 (tablet)
(Blending ingredients) (Blending amount)
Anhydrous erythritol (Tokyo Chemical Industry Co., Ltd.) 1.0
Vitamin C 20.0
Fragrance 1.2
Guam gum 0.06
Sucrose fatty acid ester 1.5
Crystalline cellulose 1.0
Powdered sugar residue

  The antioxidant comprising the C4 anhydrous sugar alcohol of the present invention as an active ingredient has an excellent hydroxy radical scavenging ability, is excellent in safety and stability, and is an external skin preparation for the purpose of antioxidant, food and drink It can be stably blended into the product composition.

Claims (4)

The antioxidant which uses the C4 anhydrous sugar alcohol represented by the following Formula (1) as an active ingredient.

  A skin external preparation containing the anhydrous sugar alcohol having 4 carbon atoms according to claim 1.   Cosmetics containing the C4 anhydrous sugar alcohol of Claim 1.   The food-drinks composition containing the C4 anhydrous sugar alcohol of Claim 1.