JPS58131911A - Cosmetic for fair-complexioned face containing fatty acid ester of quercetin - Google Patents

Abstract

PURPOSE:A cosmetic for inhibiting the activity of tyrosinase existing in the human skin, suppressing the formation of melanin, absorbing ultraviolet rays, showing improved beautifying and anti-sunburn effect, having improved shelf stability, containing a fatty acid ester of quercetin as an active ingredient. CONSTITUTION:A cosmetic containing a fatty acid ester of quercetin shown by the formula (R is 3-18C alkyl) as an active ingredient. The amount of the compound added is in a range of usually about 0.01-10wt%, preferably about 1- 5wt%. It is properly mixed with various kinds of base cosmetic materials such as various kinds of alcohols, animal and plant fats and oils, pectin, etc., components such as a stabilizer, etc. to give the cosmetic. The fatty acid ester of quercetin, for example, is synthesized by dissolving quercetin in a solvent such as dioxane, etc., followed by adding a fatty acid chloride in the presence of pyridine to it.

Description

[Detailed description of the invention] This invention relates to a skin-lightening cosmetic containing an active ingredient.

It is common for women to want to have fair and beautiful skin, and traditionally, hydrogen peroxide, zinc peroxide, magnesium peroxide,
Sodium peroxide, zinc perborate, magnesium perborate! Cosmetics containing peroxides such as perborate or sodium perborate were widely used. However, the above-mentioned peroxides have problems in terms of storage stability, physical or chemical stability, or incorporation into cosmetics, and their whitening effect is also insufficient. In recent years, cosmetics containing vitamin 0, cysteine, colloidal sulfur, etc. have been developed and are gaining acclaim. It's hard to say.

However, as a result of repeated research in order to find a skin whitening agent that does not have any undesirable side effects on the human body and has excellent skin whitening and sun protection effects, the present inventor found that the general formula: OH (wherein R When a new fatty acid ester of ercetin, which has an alkyl group of 0. to .8, is used in cosmetics, it inhibits the activity of tyrosinase present in human skin and has a remarkable melanin production inhibiting effect. In addition, it exhibits ultraviolet absorbing action, and therefore has excellent whitening and sun protection effects.Furthermore, it has a pH of 1, is stable against light and heat, and has extremely good storage stability.Furthermore, the fatty acid ester of quercetin is We have discovered a new fact that 8 substances have excellent solubility, and when incorporated into creams, etc., they easily dissolve in the oil layer, resulting in extremely good skin absorption, and they do not irritate the skin. This led to the completion of the present invention.

Accordingly, the present invention provides a skin-lightening cosmetic composition containing a fatty acid ester of quercetin having the above general formula as a loading component.

The fatty acid ester of quercetin itself has a strong tyrosinase activity inhibiting ability, has an ultraviolet absorbing effect, has increased stability against light and pH, has extremely good storage stability, and is oil-soluble. When added to creams, etc., it easily dissolves in the oil layer and increases skin absorption, resulting in excellent whitening and sun protection effects; It doesn't give any stimulation.

The fatty acid ester of quercetin in the present invention is
For example, it is easily produced by dissolving quercetin in a solvent such as dioxane and adding a fatty acid chloride in the presence of pyridine at room temperature.

Examples of the fatty acids to be esterified with quercetin in the present invention include butyric acid, capronic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, and oleic acid.

The fatty acid ester in the present invention is contained in a suitable cosmetic base material, and the content of the fatty acid ester is usually about 0.01 to 10%, particularly about 1 to 5%. However, within this range, satisfactorily whitening and sun protection effects can be achieved.
This is because when it is contained in an amount greater than 10%, there is no commensurate practical benefit, and when it is contained in an amount less than -0.01%, some concerns remain regarding the whitening effect and sun protection effect.

As stated above, the fatty acid ester of the present invention is suitably used as a skin whitening agent and a sunscreen agent. It is a product that can overcome the drawbacks and is not limited in any way by the cosmetic base material used. Therefore, in the present invention, various base cosmetic base materials that have been widely used as cosmetic base materials,
For example, various alcohols, animal and vegetable fats, surfactants,
Pectin, carboxymethyl cellulose, alginine salt, stabilizers, pigments, fragrances and other ingredients are suitably blended, and if necessary, heat-melted or melt-stirred products can be used.

Next, the whitening cosmetic composition of the present invention containing fatty acid ester of quercetin as an active ingredient will be explained with reference to Examples, Test Examples, and Prescription Examples.

Actual) INl (3-palmitate of quercetin) Dissolve 100 liters of quercetin in 4 tnl of dioxane, and add 0.5 me of pyridine [and 0.0 ml of balmitoyl chloride] under stirring at room temperature.
．． 2! Added I+4'. After 2 hours, the completed reaction was poured into ice water at 50 ml.
yap, and the precipitated yellow powder was separated from each other and subjected to thin layer chromatography [Cow-Sergen 60Pv254 (manufactured by Merck & Co., Ltd.), developing solvent: toluene-ethyl formate #
(5:C1)), and fractions with an R1 value of 0.39 were collected. After extracting this with ethyl acetate and distilling off the solvent under reduced pressure, the remaining yellow powder i'F' was 31.8 my
(melting point 163-170°0). Recrystallization from aqueous ethanol yields yellow needle-like crystals with a melting point of 185-187°9. (lay (yield 5.0%)).

Engineering R (νNujol C, -1), 3200 (OH),
1765 (o = o included 1!l &
5 M 7.90 conducted @2C Quercetin 3-butyrate) n-chloride in place of palmityl chloride 0.2 mj'
The same procedure as in Example 1 was repeated except that 0.09 ml of butyryl was used, and the fractions with an R1 value of 0.40 in thin layer chromatography were collected, extracted with ethyl acetate, and the solvent was distilled off under reduced pressure to obtain a yellow powder 22. 6 my (melting point 179-1890Q
) was obtained. Recrystallization from aqueous ethanol gave 11.2 mg (yield: 8.9%) of yellow needle crystals with a melting point of 193-196°0.

Engineering R (νmA01”-1): 3300 (OH),
1763 (o=o included 1658 (0=O) Elemental analysis value: 0□, H. Calculated value as 08・H2O:
05B, 46 H4, 65 actual measurement value: o 59.0
2 M 4.34 Example S<3-cabrilate of quercetin) Rv of 8 was measured by thin layer chromatography in the same manner as in Example 1 except that 0.11 vml of caprylic chloride was used in place of palmityl chloride o, zml. Fractions with a value of 0.45 were collected, extracted with ethyl acetate, and the solvent was distilled off under reduced pressure to give 25.8 mg of a yellow powder (melting point 166-16900).
) was obtained. Recrystallized from aqueous ethanol, melting point 1
7.0% yellow needle crystals ranging from 77° to 180° (yield 5.0%)
) was obtained.

Engineering R (Nuj01CI11-1): 3250 (OH
), 1765 (0=O), mm
061.87 H5,87 actual value: 061.73
H5,'46 Test Example 1 (Tyrosinase activity inhibition ability) The compound obtained in Example 1 was dissolved in ethanol, the pH was adjusted to 6.0 with succinic acid or potassium carbonate, and concentrated f1
．． I got 0% adhesive agent.

The results of examining the tyrosinase activity inhibitory ability of this liniment agent will be explained below.

After pretreatment of hydrolyzing 10ml of liniment agent with lipase and guinea pig skin homogenate, the L-tyrosine solution (0.3way/v) was added to a test tube.
alI) to 11111, Matsuklhane buffer (p
After adding 1 ml of 1 ml of H6,8) and 0.9 ml of the above-mentioned IJ 2-ment agent and incubating for 10 minutes in a constant temperature water bath at 37°0, tyrosinase solution (1 ml of
ray/wag) was added thereto, stirred well, and immediately set on a spectrophotometer to measure the absorbance at 4751μ over time. - As a blank test, the same absorbance measurement was performed using water instead of the liniment agent.

A liniment agent for the north wall was prepared in the same manner as above using hydrogen peroxide 2 and pentaacetoxyquercetin, and its ability to inhibit tyrosinase activity was examined.

The results of each of these tests are shown in the attached drawings (graphs). This graph shows that the liniment agent made of the compound obtained in Example 1 has a more significant tyrosinase activity inhibiting ability than the liniment agent made of hydrogen peroxide or pentaacetoxyquercetin.

Furthermore, liniment agents were prepared using the compounds obtained in Examples 2: B and 3 in the same manner as the compounds obtained in Example 1, and their tyrosinase activity inhibitory powers were investigated. The results are shown in Figure 1.

Next, formulation examples of the fair skin cosmetic of the present invention will be listed, but the present invention is not limited to these formulation examples. \Formulation example 1 [Lotion] (Ingredients) (Il part 3-cabrilate of quercetin 0
．． 10 Aminoacetic acid 0.20 Pyridoxine hydrochloride 0.05 Phenolsulfonic acid subsalt 0, 30 Propylene glycol 8
．． 00 Ethanol 5.00 Purified water 86, 3t5 Fragrance and preservative Small amount Prescription example 2 [Pack] (Ingredients) (Parts by weight) 3-butyrate of quercetin 0゜10 Stearic acid 4.00 γ Bunnoacetic acid 0.207 Enol Sulfonic acid subsalt 0630 Propylene glycol 1!5.00 Carboxyvinyl polymer 1.
20 Emulsifier 3.00 Ethanol 2.50 Titanium oxide
0.02 Purified water 79
．． 68 Fragrance 8 and preservative Small amount Prescription example 3 [Pack] (Ingredients) (Parts by weight) 3-palmitate of quercetin 0.10 Polyvinyl alcohol 15.
00 polyvinylpyrrolidone
4.00 Stearic acid 2.00
Tween 20 2.00 span 60
0.50 Propylene glycol 6.00 Ethanol
10.00 Purified water
69.70 Flavorings and preservatives
Small amount formulation example 4 [Milk lotion] (Ingredients) (Parts by weight) 3-cabrilate of quercetin 0.20 Stearic acid 2.00 Cetol
0゜50 lanolin
2.00 oleyl oleay)
2.00 Squalane 3.00 Liquid paraffin 8.00 Emulsifier
2.60 propylene glycol
4.00 Purified water
75.90 Fragrances, antioxidants and preservatives
Small prescription f45 [vanishing cream] (Ingredients) (Parts by weight) Quercetin 3-butyrate 0.20M
0 stearic acid 8.00 demand
5.00 Cetanol
3,00 Lanolin 2.00
Myristic Shun Isopropyl 6.00
Liquid paraffin 7.00 Olive oil
2.00 emulsifier
5.50 propylene glycol
3゜00 purified water 58゜3
0 Fragrance, antioxidant and preservative Small amount Prescription example 6 [Cold cream] (Ingredients) (Parts by weight) 3-palmitate of quercetin 0.10 Beeswax 10.00 Ceresin
7.00 White petrolatum
3.00 Lanolin 3.0
0 Isopropyl myristate 3.0
0 Squalane 4.00 Liquid paraffin 401.00 Polyoxyethylene cetyl ether 2.70 Emulsifier
2.30 propylene glycol
2.00 Purified water
25.00 Fragrances, antioxidants and preservatives
small amount

[Brief explanation of drawings]

The figure is a graph showing the relationship between the degree of coloring and time to show the tyrosinase activity inhibiting power of each liniment agent obtained in Test Example 1.

Claims (1)

[Scope of Claims] 1. A skin-whitening cosmetic containing as an active ingredient a fatty acid ester of quercetin having the general formula t H (in the formula, R is an alkyl group of 03 to .8). 2. 1. The fair-skinned cosmetic according to claim 1, which contains 0.01 to 10% by weight.