JP2010235483A - Singlet oxygen eliminator, skin care preparation containing the same and cosmetic - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a singlet oxygen eliminator that maintains excellent singlet oxygen eliminating ability for a long term and suppresses various reactions caused by singlet oxygen. <P>SOLUTION: The singlet oxygen eliminator contains lyoniresinol as an active ingredient. The skin care preparation and the cosmetic each comprises the singlet oxygen eliminator. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to a novel singlet oxygen scavenger and a skin external preparation and cosmetic containing the same.

  Conventionally, superoxide, hydroxy radical, hydrogen peroxide, and singlet oxygen are known as active oxygen species in a broad sense, and reaction products of these with metals and lipids are known. However, some reactive oxygen species have different numbers of electrons from, for example, ground state oxygen, such as superoxide, hydrogen peroxide, and hydroxy radicals. However, there are also singlet oxygens that are excited molecular species that are in an excited state, and each has unique characteristics that cannot be captured by the framework of reactive oxygen species based on the difference in the electronic state.

  Conventionally, electron spin resonance (ESR) has been widely used for detection of reactive oxygen species (for example, Patent Document 1), but ESR is effective for detection of radical species such as superoxide and hydroxy radicals. Even so, singlet oxygen that is not a radical species cannot be detected. Furthermore, the lifetime of singlet oxygen in water is as short as about 4 μs, and detection methods having both sensitivity and specificity are limited (for example, Patent Document 2). Therefore, in the past, those that have been reported as reactions involving active oxygen species in a broad sense and those that have been reported as effective agents for capturing active oxygen species are considered singlet when their detection methods are examined. Most of the oxygen is not clear.

  In recent years, the reactivity of each reactive oxygen species has been studied, and it has been found that each of the reactive oxygen species exhibits a specific reactivity. For example, superoxide and hydroxy radicals react with proteins and easily cause fragmentation, whereas singlet oxygen forms crosslinks to proteins and polymerizes proteins. It has been reported to show a high reactivity (for example, Non-Patent Document 1). It has also been clarified that singlet oxygen is generated on the surface of healthy skin by irradiation with ultraviolet rays and causes peroxidation of sebum that causes various skin troubles (for example, Non-Patent Document 2). ).

  Against this backdrop, the role of specific individual reactive oxygen species is becoming more important for diseases and aging that have been said to be simply involved in reactive oxygen species. The same applies to singlet oxygen. Therefore, if there is an agent capable of selectively or specifically eliminating singlet oxygen, it is effective in preventing diseases and aging involving singlet oxygen.

  Conventionally, some compounds have been known as singlet oxygen scavengers (for example, Patent Document 4). However, many of them are poor in chemical stability per se and deteriorate over time during storage. The fact is that there are many cases where the oxygen scavenging ability is low, and there are few singlet oxygen scavengers excellent in the sustainability of the effect.

Japanese Patent Laid-Open No. 2001-10954 (page 5, Example 9) JP 7-159325 A WO2005 / 072756 JP 2001-288035 A JP 2001-288035 A WO2006 / 068254

"J.Soc.Cosmet.Chem.Japan." Vol.28, No.2 1994, p.163-171 “The Journal of the Japan Cosmetic Science Society”, Vol. 19, No. 1 (1995), pp. 1-6 INDIAN J. CHEM., VOL.14B, FEBRUARY, (1976), p.128 J.Jpn.Cosmet.Sci.Soc.Vol.26, 2002, p.79-85

  Accordingly, an object of the present invention is to provide a singlet oxygen scavenger that can maintain good singlet oxygen scavenging ability for a long period of time and can suppress various reactions caused by singlet oxygen.

  Another object of the present invention is to apply to the skin, which can prevent skin aging, skin blackening, skin damage, and the like caused by a reaction involving singlet oxygen. Is to provide an agent.

  Still another object of the present invention is to provide a composition in which deterioration due to singlet oxygen, which are active ingredients such as lipids, proteins and vitamins, is suppressed and these are stably blended.

  Yet another object of the present invention is to provide a cosmetic for the purpose of preventing skin aging, whitening or skin, and preventing or improving acne.

  In order to solve the above-mentioned problems, the present inventors have searched for a singlet oxygen scavenging ability and stability of many substances, and reported application as a whitening agent (see Patent Document 3). ) Rioniresinol was found to have excellent singlet oxygen scavenging ability and stability and completed the present invention.

  That is, the present invention is a singlet oxygen scavenger containing lionilesinol as an active ingredient.

  Moreover, this invention is the skin external preparation and cosmetics containing the said singlet oxygen scavenger.

  ADVANTAGE OF THE INVENTION According to this invention, the singlet oxygen scavenger which maintains a favorable singlet oxygen scavenging ability for a long term is provided, and the various reaction caused by singlet oxygen can be suppressed.

  Then, by applying a skin external preparation or cosmetic using the singlet oxygen scavenger of the present invention to the skin, the reaction involving singlet oxygen is caused by one cause, skin aging, skin blackening Acne, skin damage and the like can be prevented.

  In addition, skin that prevents deterioration of these active ingredients in the topical skin preparations and cosmetics by blending the above singlet oxygen scavenger into the topical skin preparations and cosmetics containing lipids, proteins and vitamins as active ingredients. It can be used as an external preparation or cosmetic.

  The active ingredient of the singlet oxygen scavenger of the present invention is rioniresinol. Since this riolesinol has three asymmetric carbons, the presence of stereoisomers represented by the following formulas (A) to (H) is assumed.

（式中、Ｍｅはメチル基を示す）

(In the formula, Me represents a methyl group)

  The rioniresinol used in the present invention may be any of the above formulas (A) to (H), and these may be obtained from natural products or obtained by chemical synthesis. Even if it exists, it can be used without trouble in the present invention.

  In the above formula, the compound represented by (A) is known as (+)-Lyoniresinol ((+)-Lyoniresinol), and the compound represented by (E) is known as (-)-Lyoniresinol ((-)-Lyoniresinol). These are preferably used as the rioniresinol of the present invention.

  Furthermore, when using a natural product as lionilesinol, it is not limited to purified lionilesinol, but an extract of raw material containing rioniresinol and a crude product can also be used as a singlet oxygen scavenger of the present invention. (Fagaceae) Quercus plant lower alcohol aqueous solution extract or its refined product can be used. In addition, ume vinegar, an extract thereof, or a purified product from the ume vinegar extract can be used in the production of umeshu and umeboshi.

The Quercus plants as a raw material for the Rionireshinoru, for example, oak (Quercus mongolica Fisch.), Oak (Quercus dentate Thunb), oak (Quercus serrata Thunb), oak (Quercus acutissima Carruth), evergreen oak (Quercus myrsinaefolia Bl.) , White oak ( Quercus alba L.), common oak ( Quercus robur L .; also called Limousin oak, French oak or Spanish oak), cecil oak ( Quercus oetraea L.), cork oak ( Quercus suber L.), etc. be able to.

  Depending on the plant's production area, harvest time, extraction conditions, etc., among the above Quercus genus plants, a group of plants (plants called oaks) used as raw materials for barrels for production and storage of whiskey and brandy, It is preferable because it contains lionilesinol at a high concentration. In particular, common oak and mizunara can be suitably used because they contain lionilesinol at a high concentration.

  As an extraction solvent used for manufacture of the lower alcohol aqueous solution extract of the said Quercus genus plant, the C1-C4 lower alcohol (for example, methanol, ethanol, propanol, butanol etc.) aqueous solution etc. can be mentioned, for example. It is important that the concentration of the lower alcohol in the aqueous solution be a concentration at which rioniresinol can be efficiently extracted. Specifically, the lower alcohol concentration in the lower alcohol aqueous solution is about 10 to 100% by volume, preferably about 30 to 70% by volume, more preferably about 40 to 60% by volume. Considering that the lower alcohol can be finally blended in foods and drinks, it is preferable to use an aqueous ethanol solution as the extraction solvent from the viewpoint of safety. In addition to the lower alcohol, the extraction solvent referred to herein includes other components within a range that does not greatly impair the extraction efficiency, for example, water-soluble components such as sugars, salts, acids, alkalis or amino acids, ethyl acetate, acetone, etc. Various other solvents may be contained. In addition, what is necessary is just to set extraction time suitably, but generally more lyoniresinol can be extracted, so that extraction time is long.

  There is no particular limitation on the method of purifying lionilesinol from the above Quercus genus plant extract or ume vinegar extract, but it is preferably purified by column chromatography, particularly preferably by gel filtration chromatography. As a resin carrier used for purification, a widely used resin such as Sephadex (registered trademark) or polyacrylamide gel (Bio-Gel) manufactured by Pharmacia can be selected and used according to the target purity. . When purifying using these resins, it is preferable to use a solvent such as acetonitrile, ethanol, methanol, acetone or benzene and an aqueous solution thereof as a developing solution.

  Furthermore, rioniresinol used in the present invention can also be produced by chemical synthesis, and the synthesis is generally as follows. That is, it can be produced following the methods described in Non-Patent Document 3, Patent Document 6 and the like using 4-hydroxy-3,5-dimethoxyphenylpropionic acid as a raw material. In addition, resolution of each optical isomer of rioniresinol can also be carried out according to a known method.

  The singlet oxygen scavenger of the present invention can be prepared by combining the above rioniresinol or optical isomers thereof as they are or with an appropriate carrier. Examples of carriers that can be used include various liquid or solid excipients or extenders such as titanium oxide, calcium carbonate, distilled water, lactose, starch, and various liquid or solid excipients as shown in the specific examples described in Examples below. Is mentioned.

  The singlet oxygen scavenger of the present invention preferably has a singlet oxygen scavenging rate of 10% or more at 0.5 mg / mL, more preferably 20% or more. Furthermore, what is 20% or more at 1.0 mg / mL is preferable, and what is 30% or more is particularly preferable. In this specification, “singlet oxygen elimination rate” refers to the rate of decrease in the intensity of light emission accompanying the transition of singlet oxygen.

Specifically, the singlet oxygen scavenging rate (E) is obtained by adding singlet oxygen scavengers at various concentrations to a system in which singlet oxygen is arbitrarily generated and light emission associated with singlet oxygen transition is observed. The emission intensity (I) and the emission intensity (I ₀ ) when not added are measured, and the calculated values are calculated from the following formula using these measured values.

E = (I ₀ −I) / I ₀ × 100

  The singlet oxygen scavenger of the present invention can be used for applications that suppress reactions caused or promoted by the presence of singlet oxygen. For example, singlet oxygen is known to crosslink collagen, which is a constituent component of the dermis (Non-patent Document 1), and cross-linking of collagen reduces the elasticity and flexibility of the skin, which is one of the aging of the skin. It becomes a cause. Therefore, by applying the singlet oxygen scavenger of the present invention to the skin, it is possible to suppress the formation of cross-linking of collagen, prevent skin aging, and maintain a youthful skin. . That is, the singlet oxygen scavenger of the present invention can be used as a collagen crosslinking inhibitor.

  In addition, for example, singlet oxygen is frequently generated on the skin surface by UV-A irradiation, and is involved in immediate darkening that occurs non-enzymatically due to oxidation of dopa, and is involved in peroxidation of skin surface lipids. It is known (Non-patent Document 2). Therefore, by applying the singlet oxygen scavenger of the present invention to the skin, immediate darkening of the skin and peroxidation of the skin surface lipid can be suppressed. Furthermore, it can be used for the prevention or improvement of acne (Patent Document 5).

  In the case where the singlet oxygen scavenger of the present invention is used as an immediate blackening inhibitor, it is more preferable to use a singlet oxygen scavenger having a singlet oxygen scavenging rate larger than that of dopa. In addition, for example, singlet oxygen is known to cause or promote inactivation of many enzymes responsible for in vivo reactions. Therefore, the singlet oxygen scavenger of the present invention can be used as an enzyme deactivation inhibitor. When the singlet oxygen scavenger of the present invention is used as an enzyme deactivation inhibitor, the singlet oxygen scavenging rate of the singlet oxygen scavenger is more than the singlet oxygen scavenging rate of the enzyme. preferable.

  On the other hand, we have reported that singlet oxygen is involved in cell aging using a cell aging evaluation system in order to capture the aging phenomenon of living bodies (Non-patent Document 4). In other words, when cells were exposed to singlet oxygen, a characteristic aging phenomenon was observed that shortened cell life. This phenomenon was suppressed by applying histidine, a singlet oxygen scavenging substance, to the cells. That is, since the singlet oxygen scavenging substance has the effect of suppressing cell aging and consequently delaying aging of the living body, the singlet oxygen scavenger of the present invention should also be used as a cell aging inhibitor. Can do.

  In addition, singlet oxygen is known to cause or promote fading and discoloration of pigments such as plant extracts blended in cosmetics and foods. Even when there is no discoloration or discoloration, the presence of singlet oxygen causes the decomposition of medicinal agents incorporated into skin cosmetics, such as lipids, proteins and vitamins as active ingredients. May be promoted. When the singlet oxygen scavenger of the present invention is blended, not only the singlet oxygen scavenging ability and the effects associated therewith can be obtained, but also the effect of suppressing the decomposition of other agents blended together can be obtained. That is, the singlet oxygen scavenger of the present invention can be used as an anti-fading agent, and can also be used as a preservative for other medicinal agents such as lipids, proteins, and vitamins.

  Since the singlet oxygen scavenger of the present invention has the above-described actions and effects, it can be used for various purposes such as pharmaceuticals, quasi drugs, cosmetics, foods and the like. That is, since singlet oxygen is always present on the skin surface that is always in contact with oxygen and exposed to ultraviolet rays, the composition containing the singlet oxygen scavenger of the present invention is more useful as a skin external preparation. is there. In addition, since the reaction suppressed by the elimination of singlet oxygen is a reaction that contributes to skin aging, skin blackening, acne, and skin damage, the singlet of the present invention that can suppress such a reaction. A composition containing an oxygen scavenger as an active ingredient is particularly useful as a skin cosmetic for the purpose of preventing skin aging, whitening, acne, and beautiful skin.

  A skin external preparation or cosmetic is prepared by blending the singlet oxygen scavenger of the present invention alone or with one or more known external pharmaceutical additives or skin cosmetic additives according to a conventional method. be able to. The blending amount of the singlet oxygen scavenger of the present invention in the external preparation for skin or cosmetics differs depending on the singlet oxygen scavenging ability of the singlet oxygen scavenger in addition to the dosage form of the external preparation or cosmetic, the intended purpose, etc. In general, however, rioniresinol in the final composition is preferably 0.00001 to 10% by mass (hereinafter simply referred to as “%”) in terms of dry solids, preferably 0.001 to 5%, More preferably, it is 0.1 to 3%. If it is in this range, rioniresinol can be blended more stably and an excellent medicinal effect can be exhibited.

  The singlet oxygen scavenger of the present invention can be used alone as a skin external preparation, or a skin external preparation or cosmetic can be prepared by mixing with one or more additives. Additives added as necessary include water (purified water, hot spring water, deep sea water, etc.), alcohol, oils, surfactants, etc. that are commonly used in skin cosmetics and pharmaceutical preparations for external use. Metal soap, gelling agent, powder, alcohol, water-soluble polymer, film forming agent, resin, UV protection agent, inclusion compound, antibacterial agent, fragrance, deodorant, salt, pH adjuster, refreshing agent, Animal / microbe-derived extracts, plant extracts, blood circulation promoters, astringents, antiseborrheic agents, whitening agents, anti-inflammatory agents, active oxygen scavengers other than the singlet oxygen scavenger of the present invention, cell activators, moisturizing agents Agents, chelating agents, keratolytic agents, enzymes, hormones, vitamins and the like. The external preparation for skin can be prepared according to a conventional method, and the blending amount of the additive can also be determined according to a conventional method as long as the effects of the present invention are not impaired.

  The form of the external preparation for skin or cosmetic is not limited, and forms belonging to skin cosmetics such as emulsions, creams, skin lotions, cosmetics, packs, face wash, makeup cosmetics, shampoos, hair treatments, hair It may be in any form relating to hair cosmetics such as a styling agent, hair nourishing agent, hair restorer, etc .; and in the form of external medicines such as dispersions, ointments, aerosols, patches, poultices, liniments and the like.

  EXAMPLES Hereinafter, although an Example and a manufacture example demonstrate this invention further more concretely, this invention is not restrict | limited at all by these lower Examples.

Manufacturing example 1
Purification of (+)-Lionilesinol and (−)-Lionilesinol:
Separation of rioniresinol (racemate) synthesized in Example 6 of WO2006 / 068254 (Patent Document 6) by high performance liquid chromatography (HPLC) was performed using a chiral column. The analysis conditions of HPLC are as follows.

Column: CHIRALCEL AD-H
Column size: 0.46I. D x 25cm
Mobile phase: methanol / ethanol / acetic acid = 50/50 / 0.1 (v / v / v),
Flow rate: 1.0 mL / min Measurement wavelength: 254 nm

The optical purity of the obtained fractions (+)-Lionilesinol and (−)-Lionilesinol was 98% ee or higher, respectively. Moreover, the ratio of the obtained (+)-Lionilesinol and (−)-Lionilesinol was about 1: 1 (w / w).

Example 1
Measurement of singlet oxygen elimination constant:
The singlet oxygen scavenging rate of (+)-Lionilesinol and (−)-Lionilesinol prepared in Production Example 1 was measured as follows. Singlet oxygen was detected using an apparatus described in Japanese Patent No. 3356517 (details are in the [0026] column). A 50 μM 50% ethanol solution of Rose Bengal was circulated in the flow cell of the apparatus at a rate of 20 ml / min. When this cell was irradiated with a laser having a wavelength of 514.5 nm, which is the absorption wavelength of rose bengal, light emission accompanying the transition of singlet oxygen was observed, and the emission peak was 1268 nm. First, the emission intensity (I ₀ ) at a wavelength of 1268 nm of only the solvent was measured, and then the emission intensity (I) at a wavelength of 1268 nm when oak extract or whiskey was added at the concentration shown in Table 1 was measured. Based on these measured values, the singlet oxygen elimination rate (E) was calculated from the following formula. For comparison, 10 L of water was added to 100 g of root moth roots, extracted at room temperature, and then a root stalk extract (having active oxygen scavenging ability) which was a filtrate obtained by filtering the extract was used. The results are shown in Table 1.
E = (I ₀ −I) / I ₀ × 100

  From this result, it was demonstrated that rioniresinol exhibits an excellent singlet oxygen scavenging ability. On the other hand, it has been clarified that the singlet oxygen scavenging ability is low even though the root extract has active oxygen scavenging ability.

Example 2
Cosmetic lotion:
A lotion was prepared according to the following ingredients and production method.

(Ingredient) (mass%)
1 Glycerin 5.0
2 1,3-butylene glycol 5.0
3 Lactic acid 0.05
4 Sodium lactate 0.1
5 Polyoxyethylene (20E.O.) sorbitan monooleate 1.2
6 Ethanol 8.0
7 Methyl paraoxybenzoate 0.1
8 Fragrance 0.05
9 Rioniresinol 0.05
10 Remaining amount of purified water

( Production method )
A: 7/8 of components (5), (7), (8) and (6) are mixed and dissolved.
B: Components (1) to (4), (9) to (10) and the remaining (6) are mixed and dissolved.
C: A was added to B and mixed to obtain a skin lotion.

Example 3
Milk liquid:
An emulsion was prepared by the following ingredients and production method.

(Ingredient) (mass%)
1 Polyoxyethylene monostearate (20E.O.) sorbitan 1.0
2 Polyoxyethylene trioleate (20E.O.) sorbitan 0.5
3 Glyceryl monostearate 1.0
4 Stearic acid 0.5
5 Behenyl alcohol 0.5
6 Squalane 8.0
7 Carboxyvinyl polymer 0.1
8 Methyl paraoxybenzoate 0.1
9 Sodium hydroxide 0.05
10 Ethanol 5.0
11 Rioniresinol 0.1
12 Purified water balance 13 Fragrance 0.05
14 Purified water 5.0

( Production method )
A: Components (7) to (9) are added to component (12) and mixed uniformly at 70 ° C. B: Components (1) to (6) are mixed uniformly at 70 ° C.
C: B is added to A to emulsify, and cooled to room temperature.
D: (10), (11), (13) and (14) were added and mixed uniformly to obtain an emulsion.
.

Example 4
Liquid foundation (oil-in-water cream):
A liquid foundation was prepared by the following components and production method.

(Ingredient) (mass%)
1 Acrylic acid / alkyl methacrylate copolymer (Note 1) 0.5
2 Triethanolamine 1.5
3 Residual amount of purified water 4 Glycerin 5
5 Ethyl paraoxybenzoate 0.1
6 1,3-butylene glycol 5
7 Hydrogenated soybean phospholipid 0.5
8 Titanium oxide 5
9 Bengala 0.1
10 Yellow iron oxide 1
11 Black iron oxide 0.05
12 Stearic acid 0.9
13 Glycerol monostearate 0.3
14 cetostearyl alcohol 0.4
15 Polyoxyethylene (20E.O.) sorbitan monooleate 0.2
16 Polyoxyethylene trioleate (20E.O.) sorbitan 0.2
17 2-methoxyhexyl paramethoxycinnamate 5
18 Rioniresinol 0.5
19 Perfume 0.02
(Note 1) Pemulen TR-2 (manufactured by NOVEON)

( Production method )
A: Disperse components (6) to (11).
B: Components (12) to (17) are added to A and mixed uniformly at 70 ° C.
C: Components (1) to (5) are uniformly mixed at 70 ° C.
D: B is added to C to emulsify, and cooled to room temperature.
E: Ingredients (18) to (19) are added to D and mixed uniformly to give an oil-in-water cream
A kid foundation was obtained.

Example 5
Sunscreen cosmetics (water-in-oil cream):
A sunscreen cosmetic was prepared by the following ingredients and production method.

(Ingredient) (mass%)
1 Polyoxyethylene (20E.O.) sorbitan monolaurate 0.2
2 POE (60) hydrogenated castor oil 0.1
3 Remaining amount of purified water 4 Dipropylene glycol 10
5 Magnesium sulfate 0.5
6 Magnesium ascorbyl phosphate 3
7 Silicone compound (Note 2) 3
8 Decamethylcyclopentasiloxane 20
9 Isotridecyl isononanoate 5
10 2-Ethylhexyl paramethoxycinnamate 8
11 Rioniresinol 0.3
12 Dimethylstearyl ammonium hectorite 1.2
(Note 2) KF-6028 (manufactured by Shin-Etsu Chemical Co., Ltd.)

( Production method )
A: Components (1) to (6) are uniformly dispersed.
B: Components (7) to (12) are uniformly dispersed.
C: While stirring B, gradually add A and emulsify to form a water-in-oil cream sunscreen.
A cosmetic was obtained.

Example 6
Ointment:
An ointment was prepared according to the following ingredients and production method.

(Ingredient) (mass%)
1 Stearic acid 18.0
2 Cetanol 4.0
3 Triethanolamine 2.0
4 Glycerin 5.0
5 Dipotassium glycyrrhizinate (Note 3) 0.5
6 Rioniresinol 0.5
7 dl-α-Tocopherol acetate (Note 4) 0.2
8 Methyl paraoxybenzoate 0.1
9 Purified water balance (Note 3) Wako Pure Chemical Industries, Ltd. (Note 4) Eisai

( Production method )
A: A part of components (3), (4) and (9) is heated and mixed and kept at 75 ° C.
B: Components (1), (2) and (6) to (8) are heated and mixed, and kept at 75 ° C.
C: B was gradually added to A and dissolved in the remainder of component (9) while cooling.
(5) was added to obtain an ointment.

Example 7
Lotion agent:
A lotion preparation was prepared according to the following ingredients and production method.

(Ingredient) (mass%)
1 Glycerin 5.0
2 1,3-butylene glycol 6.5
3 Polyoxyethylene (20E.O.) sorbitan monolauric acid 1.2
Ester 4 Ethanol 8.0
5 Rioniresinol 0.05
6 Methyl paraoxybenzoate 0.2
7 Purified water balance

( Production method )
A: Components (3) to (6) are mixed and dissolved.
B: Components (1), (2) and (7) are mixed and dissolved.
C: A and B were mixed and homogenized to obtain a lotion agent.

  The lotions, emulsions, liquid foundations, sunscreen cosmetics, ointments, and lotions prepared in each of the above examples were stable and applicable to the skin without any discoloration, odor, or precipitate. It was. These cosmetics can be used to suppress various reactions involving singlet oxygen by eliminating singlet oxygen, and suppress collagen cross-linking formation, immediate skin darkening, enzyme deactivation It is useful for inhibiting lipid peroxidation, inhibiting cell aging, and anti-acne.

  Since the singlet oxygen scavenger of the present invention has an excellent singlet oxygen scavenging action, the singlet oxygen scavenger can be used for suppressing reactions caused or promoted by the presence of singlet oxygen.

  Therefore, by applying a topical skin preparation or cosmetic containing this to the skin, the reaction involving singlet oxygen may contribute to skin aging, skin blackening, skin damage, etc. It becomes possible to prevent.

In addition, if the singlet oxygen scavenger of the present invention is blended in a composition containing lipids, proteins, vitamins, etc. as active ingredients, deterioration due to singlet oxygen of these active ingredients is suppressed, and these are blended stably. Composition.

Claims (14)

  A singlet oxygen scavenger containing lionilesinol as an active ingredient.   The singlet oxygen scavenger according to claim 1, wherein the rioniresinol is (+)-rioniresinol or (-)-rioniresinol.   The singlet oxygen scavenger according to claim 1 or 2, wherein the rioniresinol is obtained from a lower alcohol aqueous solution extract of a Quercus genus plant, ume vinegar or an extract thereof.   The singlet oxygen scavenger according to any one of claims 1 to 3, wherein a singlet oxygen scavenging rate is 10% or more at 0.5 mg / mL.   An external preparation for skin comprising the singlet oxygen scavenger according to any one of claims 1 to 4.   The skin external preparation according to claim 5, which is an immediate skin darkening inhibitor or a skin surface lipid peroxidation inhibitor.   The skin external preparation according to claim 5 or 6, which is an immediate skin darkening preventive and has a singlet oxygen scavenging rate higher than that of dopa.   The external preparation for skin according to any one of claims 5 to 7, wherein the final composition contains 0.00001 to 10% by mass of rioniresinol as a dry solid content.    An external preparation for skin comprising the singlet oxygen scavenger according to any one of claims 1 to 4 and lipids, proteins or vitamins as active ingredients.   A cosmetic comprising the singlet oxygen scavenger according to any one of claims 1 to 4.   The cosmetic according to claim 10, which is a skin cosmetic for the purpose of preventing skin aging, whitening or skin.   The cosmetic according to claim 10, wherein the cosmetic is intended to prevent or improve acne.   The cosmetic according to any one of claims 10 to 12, wherein lyoniresinol is contained in the final composition in a dry solid content of 0.00001 to 10% by mass.    A cosmetic comprising the singlet oxygen scavenger according to any one of claims 1 to 4 and lipids, proteins or vitamins as active ingredients.