JPH0616531A - Cosmetic - Google Patents

Abstract

PURPOSE:To obtain a cosmetic having both beautifying and whitening and anti-inflammatory actions with high safety. CONSTITUTION:The cosmetic is characterized by including a pterocarpane-based compound which is a flavanone of formula I (R1 to R4 and R1 to R5, are H, OH, methoxy, linear, branched or cyclic <=10C alkyl), a flavanol of formula II (R5 is OH or methoxy), an isoflavone of formula III and an isoflavanone derivative of formula IV as an active ingredient and having both beautifying and whitening and anti-inflammatory actions.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel cosmetic having a highly stable whitening effect and an anti-inflammatory effect. More specifically, the present invention relates to a large cosmetic having a whitening effect and an anti-inflammatory effect, which contain a pterocarpan compound that is a flavanone, a flavanonol, an isoflavone and an isoflavanone derivative as an active ingredient.

[0002]

BACKGROUND OF THE INVENTION Although there are some unclear points regarding the mechanism of skin spots, freckles, etc., melanin pigments are generally formed due to hormonal abnormalities and ultraviolet rays from the sun, and this is due to the fact that the It is thought that it will be abnormally deposited. Melanin is produced in the skin by the enzyme tyrosinase using tyrosine as a substrate through L-dopa and dopaquinone, and then secreted to the surrounding keratinocytes. Therefore, conventionally, for the treatment of spots and freckles, a substance that inhibits the tyrosinase activity present in the skin and suppresses melanin production, for example, a method of administering a large amount of vitamin C, glutathione ointment,
As a topical whitening agent such as a method of locally applying it in the form of cream, lotion or the like, it has been practiced to incorporate these melanin production inhibiting substances into its composition. In Europe and America, hydroquinone preparations are used as medicines.

Further, when the water content in the stratum corneum of the skin decreases, it may cause rough skin. Glycerin, 1,3-butylene glycol, propylene glycol, hyaluronic acid and the like are used as a moisturizing agent in order to give an appropriate water content to the stratum corneum, thereby preventing rough skin.

On the other hand, of the ultraviolet rays, the wavelength 2 outside the medium wavelength ultraviolet
Light in the vicinity of 80 to 320 nm (hereinafter abbreviated as UV-B) causes erythema on the skin and causes blisters similar to severe burns. In addition, the wavelength of long wavelength ultraviolet is 320 to 400n.
It is recognized that the light of m (hereinafter abbreviated as UV-A) causes blackening of the skin and aging of the skin when it is applied for a long period of time. As described above, various ultraviolet absorbers against harmful ultraviolet rays, such as p-aminobenzoic acid ester and urocanic acid, can be mentioned, but they have maximum absorption in the UV-B region and cause inflammation such as erythema of the skin. The purpose is to prevent. It has been proposed to use phenyl salicylate derivatives, benzotriazole derivatives, etc. as cosmetics as UV absorbers having maximum absorption in the UV-A region that causes skin darkening and aging, but they are all phototoxic. , There is a safety problem due to light allergies.

Flavonoid compounds are abundant in nature, especially in leaves, flowers, fruits and roots of plants. Its physiological actions include antioxidation, strengthening of capillaries, prevention of bleeding, participation in redox processes in the body, and the like. It has also been known as a yellow pigment for a long time and has been used in foods, pharmaceuticals and the like. Among the flavonoid derivatives, quercetin, quercitrin, and rutin, which are flavone derivatives,
Its use is especially under consideration. Regarding rutin and the like, it is involved in the physiological activity of vitamin C as vitamin P, for example, in the hydroxylation reaction of proline and lysine necessary for the synthesis of collagen, which is the main component of biological connective tissue, to maintain the health of the body,
It plays an important role in promotion.

However, flavone derivatives such as quercetin and rutin, and furanobonol derivatives have a strong yellow color tone,
This is one of the problems in using it as a raw material for cosmetics.

[0007]

[Problems to be Solved by the Invention] Vitamin C contains heat,
It has poor stability over time with respect to light, and causes discoloration and odor particularly in systems containing water. On the other hand, the use of hydroquinone type is limited because of its safety problems such as skin irritation and allergenicity. Further, there is a problem in terms of stability because it is easily oxidized by air. Thiol-based compounds such as glutathione and cysteine have a strong offensive odor and are easily oxidized and their effects are slow. In addition, 2-mercaptoethylamine salt, N- (2-mercaptoethyl) dimethylamine salt and the like are known to decolorize the skin of black guinea pigs, but since white spots easily occur after decolorization, they are generally used. Absent.

On the other hand, although there are various components having ultraviolet absorption for the purpose of protecting the skin from harmful ultraviolet rays, there are various components as described above, but they have uniform absorption performance over a wide absorption region of UV-B and UV-A. There is nothing, UV-
The phenyl salicylate derivative and the benzotriazole derivative, which are ultraviolet absorbers having maximum absorption in the A region, have problems in safety and stability such as phototoxicity and photoallergenicity, and are difficult to apply to cosmetics in practice. is there. Therefore, at present, together with preventing skin inflammation due to ultraviolet rays,
There is a demand for a highly stable cosmetic composition that blocks not only UV-B but also UV-A to prevent skin erythema and blackening.

As described above, whitening cosmetics containing a melanin production-inhibiting substance as an active ingredient, and external preparations for skin and ultraviolet absorbers prepared by applying the same to the skin have been known. There is a demand for a highly safe cosmetic product which has an excellent production suppressing effect, protects the skin from harmful ultraviolet rays, and has an anti-inflammatory effect.

[0010]

DISCLOSURE OF THE INVENTION In view of such a situation, the present inventors previously filed a patent application (JP-A-63-208506) for a cosmetic containing dihydromyricetin belonging to flavanonol as an active ingredient, The compound has a large UV protection effect, and also exhibits oxidative stability.
It was revealed that it is excellent in stability against H, light, heat, etc. and has good storage stability, and is excellent as a raw material for cosmetics.
However, as a result of further intensive studies, cosmetics containing a pterocarpan compound, which is a flavanone, flavanonol, isoflavone and isoflavanone derivative, as an active ingredient showed good absorption performance over a wide wavelength range of ultraviolet rays, and thereby sunburn. It has been found that not only the preventive action, but also having a high stability and good whitening action and preventing skin irritation. In addition, flavanone, flavanonol, isoflavone and isoflavanone have high anti-inflammatory activity as compared with flavone and flavonol, and are colorless or light-colored compounds in the flavonoid compound group, and have a wide range of use as raw materials for cosmetics, thus completing the present invention. Came to do.

That is, the present invention is characterized by containing a pterocarpan compound, which is a flavanone, a flavanonol, an isoflavone or an isoflavanone derivative represented by the formulas 1 to 4 as an active ingredient, and has a highly stable whitening effect. And a cosmetic having an anti-inflammatory effect.

The structural characteristics of the flavanone, flavanonol, isoflavone and isoflavanone compounds in the present invention are that flavanone and flavanonol are flavonoid skeletons as compared with general flavones and flavonols including apigenin, luteolin, quercetin and rutin. In the isoflavone and isoflavanone compounds, the phenyl group is substituted in the 3-position of the chromone ring, and both are characterized in the 2- and 3-positions. The mechanism by which the above compounds are highly safe and have a whitening effect, etc. is at an unconfirmed stage, but probably the 4-position carboxy group and the 2- and 3-positions are sterically. It is considered that they influence each other extremely complicatedly, and this is a characteristic for the compound group to exert the effect of the present invention.

The flavanone, flavanonol, isoflavone and isoflavanone derivatives of the present invention, even if they are synthetic products, are extracted from nature,
You may refine. Further, when the flavanone, flavanonol, isoflavone and isoflavanone compounds of the present invention are obtained by extraction from nature, a mixture containing the compounds may be used. Further, it may be a case where two or more kinds of the compound are contained.

As shown in Tables 1 to 3 below, many examples of pterocarpan compounds which are flavanone, flavanonol, isoflavone and isoflavanone derivatives of the present invention can be found in nature.

[0015]

[Table 1]

[Chemical 5]

[Chemical 6]

[0016]

[Table 2]

[0017]

[Table 3]

The cosmetic composition of the present invention having a highly stable whitening action and anti-inflammatory action is effective against any one or more of the flavanone, flavanonol, isoflavone and isoflavanone derivatives of the pterocarpan compound of the present invention. It is contained as an ingredient. The content of the compound is suitably 0.01 to 10% by weight, preferably 0.1 to 5% by weight. If it is less than 0.01% by weight, no sufficient effect can be expected, and 10
It is uneconomical even if it is blended in excess of wt.

Within such a range, it is completely harmless to the human body, has a good absorption performance over a wide wavelength range of ultraviolet rays, and at the same time, has a sufficiently satisfactory effect of whitening and preventing skin irritation.

For example, in the case of lotion, moisturizing agents such as glycerin and propylene glycol, skin nutrients and the like are dissolved in purified water, perfumes and the like are dissolved in alcohol, and both are mixed and dissolved at room temperature. In the production of this general lotion, one or more flavanones, flavanonol, isoflavones and isoflavanone compounds of the present invention are added to the alcohol part in an amount of 0.01 to 10% by weight to make a lotion.

[0021] In the cream, purified water is used as a moisturizing agent such as glycerin, propylene glycol, sorbit, etc. in purified water, and in the case of saponified emulsification, an alkali is added and heated to about 70 ° C to form an aqueous phase portion. And On the other hand, as an oil phase, beeswax, paraffin, ceresin, hard oils and other solid oils, petrolatum, lanolin, semisolid oils such as glycerides, squalane, liquid paraffin, various ester oils and other liquid oils, preservatives, surfactants, etc. Add the oily component of
Dissolve by heating. While gently stirring the above oil phase portion, the heated water phase portion is gradually added to emulsify. In the production of this general cream, one or more of the flavanone, flavanonol, isoflavone and isoflavanone compounds of the present invention are added to the water phase part in an amount of 0.1 to 5% by weight to give a cream.

In the emulsion, as in the case of the above-mentioned cream production, a moisturizing agent such as glycerin is added to purified water, and an alkali is added in the case of saponification and emulsification. To do. As an oil phase, beeswax, paraffin, ceresin, solid oil components such as hardened oil, semi-solid oil components such as petrolatum, lanolin, glycerides, liquid oil components such as squalane, liquid paraffin, various ester oils, preservatives, surfactants, etc. An oily component is added, heated and dissolved to form an oil phase part, and an aqueous phase part is gradually added to the oil phase part to emulsify. Further, in order to adjust the viscosity, a thickener such as carboxymethyl cellulose or carboxyvinyl polymer is added and uniformly emulsified. In the production of this general emulsion, one or more of the flavanone, flavanonol, isoflavone and isoflavanone compounds of the present invention are added to the water phase part in an amount of 0.1 to 5% by weight to form an emulsion.

Regarding the method of addition, it may be added in advance or may be added during the production, and may be appropriately selected in consideration of workability.

[0024]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto. The parts shown in the examples are parts by weight, and% is% by weight.

Example-1: Synthesis of 7,3 ', 4'-trihydroxyflavanone 65 g of powdered zinc chloride was placed in 1 liter of Kolben, 160 ml of glacial acetic acid was added, and the mixture was heated to dissolve 110 g.
Resorcinol (resorcinol) was added and boiled. After boiling, stop heating and leave for about 20 minutes.
It was diluted with 500 ml of N hydrochloric acid and cooled in ice water. The precipitated crystals were collected, washed well again with 200 ml of 3N hydrochloric acid, and dried in air.

Obtained Crystal (Resacetophenone) 10
0 g and 100 g of 3,4-dihydroxybenzaldehyde
Was taken in 1 l of a triangular Kolben and dissolved by adding 500 ml of acetone, 70 ml of 50% NaOH solution was slowly added, and the container was sealed and left overnight. When the reaction solution was acidified with hydrochloric acid, crystals were precipitated. The crystals were collected by filtration, washed with water and then recrystallized from methanol to obtain a mixture (80 g) of 2,4,3 ′, 4′-tetrahydroxychalcone and 7,3′4′-trihydroxyflavanone. , This was fractionated by column chromatography (silica gel), 7, 3 ′,
4'-trihydroxyflavanone (30 g) could be obtained.

Example-2: Isolation of alpinone (5-hydroxy-7-methoxyflavanonol) Commercially available compressed sand was crushed well and repeatedly leached with diethyl ether using an Asahina circulation extractor. The immersion liquid was evaporated to dryness, and about 10-fold amount of diethyl ether was added to the residue to dissolve the dark green resin-like substance, and then a slightly yellow-green crystalline powder was obtained. (Yield: 0.4%) This was dissolved in 30 times the amount of hot toluene, decolorized with activated carbon, and the filtrate was allowed to cool,
Alpinone (5-hydroxy-7-methoxyflavanonol) is obtained at 35 ° C. or higher. (Yield: 0.2%)

Example-3: Synthesis of 5,7,4'-trihydroxyisoflavone 2,4,6-trihydroxyphenyl-4'-hydroxybenzyl ketone 1 g, benzyl chloride 2 g, anhydrous potassium carbonate 2 g in acetone 10 ml. Dissolved. This solution was reacted on a water bath for 8 hours. After the reaction, the reaction product was poured into water. After standing overnight, the generated crystals were collected by filtration and recrystallized with methanol to obtain 0.8 g of benzyl ether having a hydroxyl group benzylated. 1.1 g of this benzyl ether
It was dissolved in 00 ml of ethyl formate. This solution was slowly added dropwise to 5 g of sodium. After leaving this overnight, a paste-like lump was obtained, so ethyl formate was distilled off, and the mixture was extracted with ether. The extract was washed with an aqueous sodium hydroxide solution while cooling, and then washed with water. The ether layer was dried over magnesium sulfate, the ether was distilled off, and the distillate was crystallized with methanol. The crude crystals were recrystallized from ethanol to obtain 0.7 g of benzylated isoflavone,
It was boiled in concentrated hydrochloric acid and debenzylated to obtain 0.6 g of 5,7,4′-trihydroxyisoflavone.

Example-4: Isolation of Markiain (7,4'-dihydroxypterocarpan) 500 g of Enju root was extracted with 10 volumes of methanol under reflux for 2 hours and concentrated (yield as a dry extract). About 20
%). Further, this concentrated extract was subjected to column chromatography (silica gel) with a mixed solvent of benzene: acetone, and an elution fraction having a solvent ratio of benzene: acetone 3: 1 was concentrated. By recrystallizing this with methanol,
Marquiain was obtained (yield: 1.0%).

Example 5: Extraction of Marhahaghi 100 g of dried Marhahaghi leaves were crushed to 50% (V
/ V) It was heated and extracted with 1 liter of an aqueous solution of ethanol for 5 hours and further concentrated to obtain 15 g of an extract.

Example 6 1 kg of dried Ononis root was crushed to obtain 1 l of ethanol.
And leave for 1 month at room temperature. Further concentration gave 23 g of extract (containing 99% or more solids).

Example-7 Lotion (1) 7, 3 ', 4'-trihydroxyflavanone 1.0 part (2) Glycerin 2.0 (3) Ethyl alcohol 7.0 (4) Methyl paraoxybenzoate 0.05 (5) Polyoxyethylene (20) Sorbitan monooleate 0.5 (6) Citric acid 0.01 (7) Sodium citrate 0.1 (8) Perfume 0.1 (9) With purified water The total amount is 100. Components (1) to (4) and (8) are mixed and dissolved. Separately, the components (5) to (7) and (9) are mixed and dissolved. Then, both are mixed and filtered with a Tetoron cloth (300 mesh) to obtain a product.

Example-8 Cream (1) 50% (V / V) ethanolic aqueous solution of Marhahagi Extract 2.0 parts (2) Squalane 10.0 (3) Olive oil 3.0 (4) Stearic acid 2 0.0 (5) Beeswax 2.0 (6) Octyldodecyl myristate 3.5 (7) Polyoxyethylene (20) Cetyl ether 3.0 (8) Behenyl alcohol 1.5 (9) Glycerin monostearate 2.5 (10) 1,3-Butylene glycol 8.5 (11) Methyl paraoxybenzoate 0.2 (12) Ethyl paraoxybenzoate 0.05 (13) Perfume 0.1 (14) Total amount to 100 with purified water. The components (2) to (9) are dissolved by heating and mixed, and the mixture is kept at 70 ° C. to obtain an oil phase. The components (1) and (10) to (12) are dissolved in the component (14) by heating and mixed, and the mixture is kept at 75 ° C. to form an aqueous phase. The aqueous phase is added to the oil phase to emulsify, component (13) is added, and the mixture is stirred and cooled to 30 ° C. to obtain a product.

Example-9 Emulsion (1) 5,7,4'-Trihydroxyisoflavone 1.0 part (2) Squalane 2.0 (3) Olive oil 2.0 (4) Jojoba oil 5.0 (5) Cetyl alcohol 1.5 (6) Glycerin monostearate 2.0 (7) Polyoxyethylene (20) Cetyl ether 3.0 (8) Polyoxyethylene (20) Sorbitan monooleate 2.0 (9) Dipropylene Glycol 1.0 (10) Glycerin 2.0 (11) Perfume 0.1 (12) Methyl paraoxybenzoate 0.2 (13) Make the total amount 100 with purified water Components (1) to (8) are heated Dissolve and mix, keep at 70 ° C. to make an oil phase. The components (9), (10) and (12) are dissolved in the component (13) by heating and mixed, and the mixture is kept at 75 ° C. to form an aqueous phase. The aqueous phase is added to the oil phase to emulsify and disperse, and the component (11) is added and stirred to cool to 30 ° C. to obtain a product.

Example-10 Pack (1) 5-hydroxy, 7-methoxyflavanonol 3.0 parts (2) Polyvinyl alcohol 11.5 (3) 1,3-butylene glycol 2.5 (4) Polyoxy Ethylene (40) hydrogenated castor oil 1.0 (5) ethyl alcohol 7.0 (6) methyl paraoxybenzoate 0.2 (7) fragrance 0.05 (8) Purified water to make the total amount 100 Component (1 ) To (8) are dissolved by heating at 75 ℃, 30 ℃
Cool down to product. (Below margin)

[0036]

The flavanone, flavanonol of the present invention,
A cosmetic containing isoflavones and isoflavanone compounds as active ingredients has a highly stable whitening action and anti-inflammatory action, and is also preferable in terms of safety. Hereinafter, the effects of the present invention will be described with reference to experimental examples.

[Experimental Example] Efficacy Test Example 1 Whitening action To investigate the inhibitory action on tyrosinase activity, 0.0
Incubate the 5% aqueous solution at 37 ℃ for 2 weeks,
The tyrosinase activity inhibitory ability before and after that was measured. As a comparative example, ascorbic acid, loofah water, and hot water extract of loofah fruits, which have been conventionally used as cosmetics, were similarly tested. The flavonoids obtained in Examples 1, 2 and 3 were used as samples. As a method for preparing a hot water extract of loofah (comparative example), 10 g of the dried product was extracted with hot water (95 ° C., 3 hours, 300 ml), and the filtrate was freeze-dried to obtain a sample.

Measurement of thyrodinase activity inhibitory action: 1 ml of L-tyrosine solution (0.3 mg / ml), 1 ml of Max Bain's buffer (pH 6.8), and 0.15% aqueous solution of the sample in a test tube. Add 0.9 ml to 37
Incubated for 10 minutes in a constant temperature water bath at ℃. 0.1 ml of an aqueous solution of tyrosinase (1 mg / ml) was added thereto, well stirred, incubated at 37 ° C. for 12 minutes, set in a spectrophotometer, and the absorbance at 475 nm was measured. On the other hand, the same absorbance measurement was performed using distilled water instead of the above sample as a blank, and the tyrosinase activity inhibition rate of each sample was calculated from the following formula. In the formula, A means the absorbance when each sample was added, and B means the absorbance of the blank. Inhibition rate (%) = (1−A / B) × 100

The results of these tests are shown in Table 4. As is clear from Table 4, the flavonoid compounds obtained in Examples 1, 2 and 3 have a more remarkable thyrodinase activity inhibitory activity than loofah water and a hot water extract of loofah. It was confirmed that the stability was good, and that it had a stronger tyrosinase activity inhibitory effect than vitamin C after being left at 37 ° C. for 2 weeks. Further, according to these stability tests, these flavonoid compounds did not show any odor or discoloration. Furthermore, when the flavonoid compounds obtained in Examples-4 to 6 or the extracts containing the flavonoid compound of the present invention were tested in the same manner, it was found that the flavonoid compounds exhibited an equally good thyrodinase activity inhibitory activity. (Below margin)

[0040]

[Table 4] Tyrosinase activity inhibition ────────────────────────── Sample concentration Activity inhibition rate (%) (%) ───── ────── Before warming After warming ────────────────────────── Example-1 0.15 80 78 78 Example- 2 0.15 61 61 Example-3 0.15 63 61 Vitamin C 0.15 94 25 Loofah water 0.15 9 9 Loofah 0.15 31 31 Hot water extract ─────────── ────────────────

Efficacy test example 2 Anti-inflammatory effect In order to investigate the anti-inflammatory effect, a sample of 0.01%, 0.1
%, 1.0%, each aqueous solution was tested for suppressing histamine release. As a comparative example, hot water extracts of loofah water and Kitia aloe, which have been conventionally used in cosmetics, were similarly tested. The flavonoid compounds obtained in Examples-1, 2 and 3 were used as samples. The loofah water is the same as that used in Experimental Example 1. Further, as a method for preparing a hot water extract of Kidachi aloe (comparative example), 10 g of the dried product is heated and extracted with 300 ml of water for 3 hours,
A lyophilized product was used (containing 99% or more solid matter).

Histamine release inhibition test; Male Spraqu according to the report of Hirai et al. (Biopharmaceutical Journal, 37 , 374, 1983.).
The histamine release inhibitory effect on mast cells collected from the abdominal cavity of e-Dawley rats (200 to 450 g) was measured. Ie 4 ppm compound 48/80
The inhibitory effect on histamine release by A. was determined as the release inhibition rate (%).

The results are shown in Table 5. From these results, the flavonoid compounds obtained in Examples-1, 2 and 3 have a remarkable histamine release inhibitory action and are excellent in anti-inflammatory action as compared with the hot water extract of loofah water and Kitia aloe. I found that. Further, the flavonoid compounds obtained in Examples 4 to 6 or the extracts containing the flavonoid compounds of the present invention were tested in the same manner, and it was found that they exhibited a good anti-inflammatory action. (Below margin)

[0044]

[Table 5] Histamine release inhibitory effect ────────────────────────── Sample concentration Histamine (%) Release inhibitory rate (%) ──── ────────────────────── Example-1 1.0 100 0.1 99 0.01 70 Example-2 1.0 100 0.1 0.1 100 0.01 71 Example-3 1.0 100 0.1 100 0.01 81 Loofah water 1.0 65 0.1 23 0.01 13 Kitta aloe 1.0 80 Hot water extract 0.1 61 0.01 35 ────────────────────────── (Margins below)

Efficacy Test Example 3 Usage Test A usage test was carried out using 30 healthy subjects. As the samples, the cosmetics of Examples 7 and 9 were used, and only the weight% of the flavonoid compound was changed. A UV-B lamp (TOSHIBA FL-20SE) was used to irradiate a 2 cm square site on the inner side of the forearm of the subject with ultraviolet rays having an intensity of ³ mw / cm ² for 1 minute. After applying the above samples to each site twice in the morning and evening every day for 3 days, the inflammation suppression effect was applied.
The survey was conducted and evaluated. The effect of suppressing pigmentation after 1 month of use was also evaluated by conducting an questionnaire survey. Incidentally, one of the sites irradiated with ultraviolet rays was a control in which nothing was applied. The evaluation criteria of the questionnaire were based on the following, and evaluated in comparison with the control. (Judgment Criteria) Valid ◎ Slightly Valid ○ Almost Invalid △ Invalid × (Margins below)

[0046]

[Table 6-1] Questionnaire results of inflammation suppression effect (Below margin)

[0047]

[Table 6-2] Results of suppression effect of pigmentation

From the results shown in Table 6, it is understood that the cosmetics used in the present invention exhibit a remarkable effect of suppressing inflammation and pigmentation after sunburn.

Efficacy Test Example 4 Safety Test In order to clarify the safety of the flavonoid compound of the present invention, a primary irritation test for humans was conducted by an occlusive patch test. That is, using Fin Chamber (manufactured by EPITEST Co., Ltd.), 30 healthy people were occluded on the flexed side of the forearm for 48 hours, and after the patch test plaster was removed, 1 hour, 24 hours, and 48 hours later. It judged using the average value of the judgment of. The flavonoid compounds obtained in Examples 1 and 2 and 3 were used as samples, and the coating concentration was 10% (W / W).
An aqueous solution was used, and distilled water was used as a control. judgment result,
No erythema was observed in the flavonoid compound of the present invention, while a slight erythema was observed in 5 of the distilled water as a control. From these results, it was confirmed that flavanone, flavanonol and isoflavone compounds have extremely low primary irritation and are highly safe to the skin. In addition, Example-4 to
The flavonoid compound obtained in 6 or the water-soluble extract containing the flavonoid compound was tested in the same manner, and was found to be similarly highly safe to the skin.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Akio Monobe 2-130, Torimi-cho, Nishi-ku, Nagoya, Aichi Prefecture, Central Research Institute, Japan Menard Cosmetics Co., Ltd. (72) Iwa Fukunaga 2 Torimi-cho, Nishi-ku, Nagoya, Aichi Prefecture 130-chome, Central Research Institute of Japan Menard Cosmetics Co., Ltd.

Claims (4)

[Claims] 1. A cosmetic having a highly stable whitening effect and an anti-inflammatory effect, which comprises blending at least one kind of flavanone represented by Formula 1 as an active ingredient. [Chemical 1] (In the formula 1, R1, R2, R3, R4 and R1 ′, R
2 ′, R3 ′, R4 ′, and R5 ′ represent a hydrogen atom, a hydroxyl group, a methoxy group, or a linear, branched, or cyclic alkyl group (provided that the number of carbon atoms is 1 to 10). ) 2. A cosmetic having a highly stable whitening action and an anti-inflammatory action, which comprises blending at least one kind of flavanonol represented by the formula 2 as an active ingredient. [Chemical 2] (In the formula 2, R1, R2, R3, R4 and R1 ′, R
2 ′, R3 ′, R4 ′, and R5 ′ are hydrogen atoms, a hydroxyl group, a methoxy group, or a linear, branched, or cyclic alkyl group (provided that the number of carbon atoms is 4 to 10), and R5 is Represents a hydroxyl group or a methoxy group. ) 3. A cosmetic having a highly stable whitening action and an anti-inflammatory action, which comprises at least one isoflavone represented by the formula 3 as an active ingredient. [Chemical 3] (In the formula 3, R1, R2, R3, R4 and R1 ′, R
2 ', R3', R4 ', and R5' represent a hydrogen atom, a hydroxyl group, a methoxy group, or a linear, branched, or cyclic alkyl group (provided that the number of carbon atoms is 4 to 10). ) 4. A cosmetic having a highly stable whitening action and an anti-inflammatory action, which comprises at least one of pterocarpan, which is an isoflavanone derivative represented by the formula 4, as an active ingredient. [Chemical 4] (In Formula 4, R1, R2, R3, R4 and R1 ′, R
2 ', R3', and R4 'represent a hydrogen atom, a hydroxyl group, a methoxy group, or a linear, branched, or cyclic alkyl group (provided that the number of carbon atoms is 4 to 10). )