CA1162564A - Skin-beautifying cosmetic composition - Google Patents
Skin-beautifying cosmetic compositionInfo
- Publication number
- CA1162564A CA1162564A CA000427867A CA427867A CA1162564A CA 1162564 A CA1162564 A CA 1162564A CA 000427867 A CA000427867 A CA 000427867A CA 427867 A CA427867 A CA 427867A CA 1162564 A CA1162564 A CA 1162564A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- isopropyltropolone
- skin
- esters
- fatty acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
4-Isopropyltropolone having the formula:
and/or the fatty acid esters thereof having the formula:
4-Isopropyltropolone having the formula:
and/or the fatty acid esters thereof having the formula:
Description
~ I 62564 1 ~ACKGROUND OF THE INVENTION
FIELD OF THE INVENTION
Thls invention relates to a skin beautifylng cosmetic composltion, more particularly a skin beautify-ing cosmetic composition contalning 4-isopropyltropolone and/or fatty acid esters thereof as active ingredients.
DESCRIPTION OF THE PRIOR ART
It is an eternal wish common to womankind to have a fair and beautiful skin, and a variety of cosmetic preparations blended with the peroxides such as hydrogen peroxide, zinc peroxide, magnesium peroxide, sodium peroxide, zinc perborate, magnesium perborate, sodium perborate, etc., have been offered to llve up to such feminine desire. However, the peroxides such as mentioned above had the problems in keeping quality, physlcal or chemlcal stability and blending compatibility wlth the cosmetic composltlons, and also thelr skin-beautlfying effect was unsatlsfactory. There have been developed and commonly used lately the cosmetics blended with vitamln C, cystlne, colloldal sulfur and the llke, but even these cosmetics can not still be deemed satisfactory in keeping quality, stability and beautifying effect.
1 SU~ARY OF THE INVENTION
An ob;ect of this invention is to provide an improved skin-beautifying cosmetic composition.
- Another object of this invention is to provide the novel fatty acid esters of 4-isopropyltropolone which can be used as active lngredient for the skin-beautifying and whitening cosmetic preparations.
As a result of extensive studies in a search for a cosmetic agent which has no side effects unfavorable to the human body and yet can produce excellent skin-beautifying and suntan preventive effects, this inventor found out the new facts that 4-isopropyltropolone having the formula:
OH
and/or the ~atty acid esters thereof having the formula:
O
OCR
(wherein R is a hydrocarbon group having 1 to 18 carbon atoms) can produce a marvelous skin-beautifying effect as well as ~ ~ 8256,~
1 a splendid suntan preventive effect as they have an inhibitory action against activity o~ tyrosinase existing in the human skin to show a prominent suppressive action against growth of melanin as well as high ultraviolet absorptivity, and they also have high stability to pH, light and heat and excellen~ shelf stability, and that particularly the fatty acid esters of 4-isopropyltropolone have excellent oil solubility and, when blended in a cream or such, they are easily dissolved in the oil layer to show extremely high skin absorptivity, and further, they are not irritatmg to the skin.
BRIEF DESCRIPTION OF THE DRAWINGS
Fig. 1 is a graph showing the relation between degree of pigmentation and time for illustrating the tyrosinase activity inhlbiting ability of the liniment obtained in Test 1.
Fig. 2 is a graph showing the relation between degree of pigmentation and time for illustratlng the tyrosinase activity inhibiting ability of 4-isopropyl-tropolone prepared by hydrolyzing the liniment obtainedin Test 2 with Na2CO3.
DESCRIPTION OF THE PREFERRF.D EMBODIMENTS
The skin-beautifying cosmetic composition of this invention has as its active ingredients 4-isopropyl-tropolone and/or a fatty acid ester thereof blended ina base, and these active ingredients are usually contained ~ 1 625~4 1 in an amount of about 0.0001 to 10% by weight, preferably ab.out 0.001 to 5% by weight. A highly satisfactory skin-beautlfying effect and anti-suntan e~fect are provided from the said range of content of the active ingredients, but it should be noted that if said active ingredients are contalned in excess of 10%, no corresponding merit is derived, whlle if the content is less than 0.0001%, some suspicion arises over the intended effects of the composition.
In case the active ingredient is 4-isopropyl-tropolone, if its activity site is blocked by a metal, it loses its tyrosinase activity lnhibitory action.
In fact, in the presence of 1 ppm of Fe3 , 23.51 ppm of 4-isopropyltropolone is deprived of its tyrosinase activity inhibitory action, and likewise, in the presence of 1 ppm of copper Cu2+, 13.78 ppm of 4-isopropyl-tropolone loses its tyrosinase activity inhibitory actlon. In order to eliminate obstruction by such metal ions against the tyrosinase activity inhibitory action, it is suggested to add a sequestering agent (chelating agent) such as EDTA in an amount of approximately 0.01 to 0.05% (based on the total weight of the composition).
The fatty acid esters of 4-isopropyltropolone according to this invention can be produced, for example, by adding a chloride of a fatty acid to 4-isopropyltropolone in the presence of pyridine.
As for the fatty acids used for the esterifica-tion reaction with 4-isopropyltropolone in this invention, 56~
1 there are employed those having 2 to 19 carbon atoms, .~ typical examples thereof being butyric acid, caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid and oleic acid.
The thus obtained fatty acid esters of 4-isopropyltropolone are novel substances. Among these esters, stearic acid ester and palmitic acid ester are most preferred for use as active ingredient for the skin-beautifying cosmetics.
As described above, the present invention flnds optimal applications as a skin-beauti~ying agent and anti-suntan agent, and thus the skin-beautifying cosmetic composition of this invention containing said 4-isopropyltropolone or a ~atty acid ester thereof as active ingredlent has eliminated the inherent defects of the conventional cosmetic preparations of this type and is not sub~ect to any restrictions by the cosmetic base used and other factors. Therefore, in this invention, all sorts of heretofore used cosmetic base materials such as, for example, various kinds of alcohols, animal or vegetable fats, surfactants, pectin, carboxymethyl cellulose, alginates, etc., as well as other additives such ~s stabilizers, pigments, aromatics, etc., may be suitably blended, and if desired, the blend may be melted by heating or may be melted and stirred. The composition of this invention can be used in these and a wide variety of other forms.
The skin-beautifying cosmetic preparations 1 16~5~4 1 according to this invention are further described herein-below by citing their synthesis examples, test examples and prescriptions.
Synthesis Example 1 (2-palmitate of 4-isopropyltropolone) 16.4 g of 4-isopropyltropolone was dissolved in 300 ml of pyridine and the mixture was stirred at room temperature and further added with 27.5 g of palmitoyl chloride. After passage of 10 minutes, the mixture was heated to 70C for 30 minutes and then allowed to cool by itself to 0C for one hour.
The filtrate, from which the precipitated crystals of pyridine hydrochloride had been removed, was concentrated and evaporated to dryness under reduced pressure, and the residue was added with 300 ml of water and stirred at room temperature for 10 minutes to elute the pyridine hydrochloride. Then the insoluble matter was gathered, dried and recrystallized twice from ethanol, whereby there was obtained 32.2 g of white crystals (yield: 80.0%). This product is 2-palmitate of 4-isopropyltropolone.
Melting point: 27 - 28C
IR (KBr): 1760 cm 1 (C=O); 1660 cm 1 (C=0) Elemental analysis:
Calculated: C, 77.61; H, 10.45 25 ~ Found: C, 77.12; X, 10.42 0.1 g of this product was dissolved in 10 ml 1 1 62~64 1 of ethanol and this solutlon was probed by T.L.C.
(developer: ether/benze~e/ethanol/acetic acld =
40/50/2/0.2; color producing reagent: ferric sulfide).
One spot was detected at Rf = 0.924.
Synthesis Example 2 (2-butyrate of 4-isopropyltropolone) 16.4 g of 4-lsopropyltropolone was dissolved in 300 ml of pyrldine and the mixture, while cooled with ice, was added with 10.66 g of n-butyryl chloride under stlrring, heated at room temperature for 30 minutes and then allowed to cool naturally to 0C for one hour.
This mixture was then treated simllarly to Synthesis Example 1 to obtain 17.57 g of white crystals (yield:
75%). This product is 2-butyrate of 4-lsopropyltropolone.
IR (KBr): 1763 cm 1 (C=O); 1658 cm 1 (C=O) Elemental analysis:
Calculated: C, 71.17%, H, 7.74%
Found: C, 71.10%; H, 7.71%
Synthesis Example 3 (2-caprylate of 4-isopropyltropolone) 16.4 g of 4 isopropyltropolone was dissolved in 300 ml of pyridine and then further added with 16.27 g of capryl chloride while cooled with ice and under stirrlng, and the resulting mixture was treated after the manner of Synthesis Example 1 to obtain 21.78 g of white crystals (yield: 75~). This product is 2-caprylate of 4-isopropyltropolone.
~62564 1 IR (KBr): 1765 cm 1 (C=0); 1660 cm 1 (C=0) Elemental analysis:
Calculated: C, 74.44%; H~ 9.37%
Found: C, 74.25%; H~ 9.26%
Synthesis Example 4 (2-acetylate of 4~isopropyltropolone) 16.4 g of 4-isopropyltropolone was dissolved in 300 ml of pyridine, then added with 7. 85 g of acetyl chloride under iCe cooling and stirring and sub~ec~ed to the same treatment as in Synthesis Example 2 to obtain 16.5 g of white crystals (yield: 80%). This product is
FIELD OF THE INVENTION
Thls invention relates to a skin beautifylng cosmetic composltion, more particularly a skin beautify-ing cosmetic composition contalning 4-isopropyltropolone and/or fatty acid esters thereof as active ingredients.
DESCRIPTION OF THE PRIOR ART
It is an eternal wish common to womankind to have a fair and beautiful skin, and a variety of cosmetic preparations blended with the peroxides such as hydrogen peroxide, zinc peroxide, magnesium peroxide, sodium peroxide, zinc perborate, magnesium perborate, sodium perborate, etc., have been offered to llve up to such feminine desire. However, the peroxides such as mentioned above had the problems in keeping quality, physlcal or chemlcal stability and blending compatibility wlth the cosmetic composltlons, and also thelr skin-beautlfying effect was unsatlsfactory. There have been developed and commonly used lately the cosmetics blended with vitamln C, cystlne, colloldal sulfur and the llke, but even these cosmetics can not still be deemed satisfactory in keeping quality, stability and beautifying effect.
1 SU~ARY OF THE INVENTION
An ob;ect of this invention is to provide an improved skin-beautifying cosmetic composition.
- Another object of this invention is to provide the novel fatty acid esters of 4-isopropyltropolone which can be used as active lngredient for the skin-beautifying and whitening cosmetic preparations.
As a result of extensive studies in a search for a cosmetic agent which has no side effects unfavorable to the human body and yet can produce excellent skin-beautifying and suntan preventive effects, this inventor found out the new facts that 4-isopropyltropolone having the formula:
OH
and/or the ~atty acid esters thereof having the formula:
O
OCR
(wherein R is a hydrocarbon group having 1 to 18 carbon atoms) can produce a marvelous skin-beautifying effect as well as ~ ~ 8256,~
1 a splendid suntan preventive effect as they have an inhibitory action against activity o~ tyrosinase existing in the human skin to show a prominent suppressive action against growth of melanin as well as high ultraviolet absorptivity, and they also have high stability to pH, light and heat and excellen~ shelf stability, and that particularly the fatty acid esters of 4-isopropyltropolone have excellent oil solubility and, when blended in a cream or such, they are easily dissolved in the oil layer to show extremely high skin absorptivity, and further, they are not irritatmg to the skin.
BRIEF DESCRIPTION OF THE DRAWINGS
Fig. 1 is a graph showing the relation between degree of pigmentation and time for illustrating the tyrosinase activity inhlbiting ability of the liniment obtained in Test 1.
Fig. 2 is a graph showing the relation between degree of pigmentation and time for illustratlng the tyrosinase activity inhibiting ability of 4-isopropyl-tropolone prepared by hydrolyzing the liniment obtainedin Test 2 with Na2CO3.
DESCRIPTION OF THE PREFERRF.D EMBODIMENTS
The skin-beautifying cosmetic composition of this invention has as its active ingredients 4-isopropyl-tropolone and/or a fatty acid ester thereof blended ina base, and these active ingredients are usually contained ~ 1 625~4 1 in an amount of about 0.0001 to 10% by weight, preferably ab.out 0.001 to 5% by weight. A highly satisfactory skin-beautlfying effect and anti-suntan e~fect are provided from the said range of content of the active ingredients, but it should be noted that if said active ingredients are contalned in excess of 10%, no corresponding merit is derived, whlle if the content is less than 0.0001%, some suspicion arises over the intended effects of the composition.
In case the active ingredient is 4-isopropyl-tropolone, if its activity site is blocked by a metal, it loses its tyrosinase activity lnhibitory action.
In fact, in the presence of 1 ppm of Fe3 , 23.51 ppm of 4-isopropyltropolone is deprived of its tyrosinase activity inhibitory action, and likewise, in the presence of 1 ppm of copper Cu2+, 13.78 ppm of 4-isopropyl-tropolone loses its tyrosinase activity inhibitory actlon. In order to eliminate obstruction by such metal ions against the tyrosinase activity inhibitory action, it is suggested to add a sequestering agent (chelating agent) such as EDTA in an amount of approximately 0.01 to 0.05% (based on the total weight of the composition).
The fatty acid esters of 4-isopropyltropolone according to this invention can be produced, for example, by adding a chloride of a fatty acid to 4-isopropyltropolone in the presence of pyridine.
As for the fatty acids used for the esterifica-tion reaction with 4-isopropyltropolone in this invention, 56~
1 there are employed those having 2 to 19 carbon atoms, .~ typical examples thereof being butyric acid, caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid and oleic acid.
The thus obtained fatty acid esters of 4-isopropyltropolone are novel substances. Among these esters, stearic acid ester and palmitic acid ester are most preferred for use as active ingredient for the skin-beautifying cosmetics.
As described above, the present invention flnds optimal applications as a skin-beauti~ying agent and anti-suntan agent, and thus the skin-beautifying cosmetic composition of this invention containing said 4-isopropyltropolone or a ~atty acid ester thereof as active ingredlent has eliminated the inherent defects of the conventional cosmetic preparations of this type and is not sub~ect to any restrictions by the cosmetic base used and other factors. Therefore, in this invention, all sorts of heretofore used cosmetic base materials such as, for example, various kinds of alcohols, animal or vegetable fats, surfactants, pectin, carboxymethyl cellulose, alginates, etc., as well as other additives such ~s stabilizers, pigments, aromatics, etc., may be suitably blended, and if desired, the blend may be melted by heating or may be melted and stirred. The composition of this invention can be used in these and a wide variety of other forms.
The skin-beautifying cosmetic preparations 1 16~5~4 1 according to this invention are further described herein-below by citing their synthesis examples, test examples and prescriptions.
Synthesis Example 1 (2-palmitate of 4-isopropyltropolone) 16.4 g of 4-isopropyltropolone was dissolved in 300 ml of pyridine and the mixture was stirred at room temperature and further added with 27.5 g of palmitoyl chloride. After passage of 10 minutes, the mixture was heated to 70C for 30 minutes and then allowed to cool by itself to 0C for one hour.
The filtrate, from which the precipitated crystals of pyridine hydrochloride had been removed, was concentrated and evaporated to dryness under reduced pressure, and the residue was added with 300 ml of water and stirred at room temperature for 10 minutes to elute the pyridine hydrochloride. Then the insoluble matter was gathered, dried and recrystallized twice from ethanol, whereby there was obtained 32.2 g of white crystals (yield: 80.0%). This product is 2-palmitate of 4-isopropyltropolone.
Melting point: 27 - 28C
IR (KBr): 1760 cm 1 (C=O); 1660 cm 1 (C=0) Elemental analysis:
Calculated: C, 77.61; H, 10.45 25 ~ Found: C, 77.12; X, 10.42 0.1 g of this product was dissolved in 10 ml 1 1 62~64 1 of ethanol and this solutlon was probed by T.L.C.
(developer: ether/benze~e/ethanol/acetic acld =
40/50/2/0.2; color producing reagent: ferric sulfide).
One spot was detected at Rf = 0.924.
Synthesis Example 2 (2-butyrate of 4-isopropyltropolone) 16.4 g of 4-lsopropyltropolone was dissolved in 300 ml of pyrldine and the mixture, while cooled with ice, was added with 10.66 g of n-butyryl chloride under stlrring, heated at room temperature for 30 minutes and then allowed to cool naturally to 0C for one hour.
This mixture was then treated simllarly to Synthesis Example 1 to obtain 17.57 g of white crystals (yield:
75%). This product is 2-butyrate of 4-lsopropyltropolone.
IR (KBr): 1763 cm 1 (C=O); 1658 cm 1 (C=O) Elemental analysis:
Calculated: C, 71.17%, H, 7.74%
Found: C, 71.10%; H, 7.71%
Synthesis Example 3 (2-caprylate of 4-isopropyltropolone) 16.4 g of 4 isopropyltropolone was dissolved in 300 ml of pyridine and then further added with 16.27 g of capryl chloride while cooled with ice and under stirrlng, and the resulting mixture was treated after the manner of Synthesis Example 1 to obtain 21.78 g of white crystals (yield: 75~). This product is 2-caprylate of 4-isopropyltropolone.
~62564 1 IR (KBr): 1765 cm 1 (C=0); 1660 cm 1 (C=0) Elemental analysis:
Calculated: C, 74.44%; H~ 9.37%
Found: C, 74.25%; H~ 9.26%
Synthesis Example 4 (2-acetylate of 4~isopropyltropolone) 16.4 g of 4-isopropyltropolone was dissolved in 300 ml of pyridine, then added with 7. 85 g of acetyl chloride under iCe cooling and stirring and sub~ec~ed to the same treatment as in Synthesis Example 2 to obtain 16.5 g of white crystals (yield: 80%). This product is
2-acetylate of 4-isopropyltropolone.
Elemental analysis:
Calculated: C, 69.88%, H, 6.84%
Found: C, 69.48%; H, 6.82%
Synthesis Example 5 (2-stearate of 4-isopropyltropolone) 16.4 g of 4-isopropyltropolone was dissolved in 300 ml of pyridine, added with 30.3 g of stearoyl chlorlde under stlrrlng at room temperature and treated according to Synthesis ~xampie 1 to obtain 35.0 g o~
white crystals (yield: 80.0%). This product is 2-stearate o~ 4-isopropyltropolone.
Melting point: 39 - 40C
Elemental analysis:
Calculated C, 78.o8%~ H, 10.77%
Found: C, 78.00%; H, 10.78%
Rf (measured in the same way as in the case 1 of palmitate): 0.941.
~.
Test Example 1 0.05 g of 4 isopropyltropolone was dissolved in a 30% ethanol-water mixture, and then 0.03% of EDTA
was added and dissolved therein. After ad~usting the pH of the solution by using succinic acid and potassium carbonate, water was added thereto to make the total amount 100 parts. Ihere was obtained a liniment with a 4-isopropyltropolone concentration of 0.05%.
The tyrosinase activity inhibiting ability of the thus obtained liniment was examined in the follow-ing way.
1 ml of an L-tyrosine solution (0.3 mg/ml), 1 ml of Macllvaine's buffer (pH 6.8) and 0.9 ml of said liniment were added into a test tube and incubated in a 37C temperature-controlled water bath for 10 minutes. The mixture was then added with 0.1 ml of a tyrosinase solution (0.3 mg/ml) and stirred well, and then immediately a spectrophotometer was set and the absorbance at 475 m~ was measured with passage of time.
As control, a similar mixed solution was prepared by using a 30% ethanol solution instead of said liniment and its absorbance was measured in the same way.
Comparative Test Example 1 A 0.05~ concentration liniment was prepared in the same way as Test Example 1 except for use of 11 625~4 1 colchicine inste~d of 4-isopropyltropolone, and its tyrosinase activity inhibiting capacity was examined.
The test results of said Test Example 1 and Comparative Test Example 1 are shown in Fig. 1. It will be appreciated from Fig. 1 that the liniment obtained in Test Example 1 has far higher tyrosinase activity inhibiting ability than the liniment obtained in Com-parative Test Example 1.
Test Example 2 The compound obtained in Synthesis Example 1 was dissolved in ethanol and then the pH of the solution was ad~usted to 6.3 with succinic acid or potassium carbonate to obtain a liniment with a 1.0% concentration.
The tyrosinase activlty inhibiting performance of this liniment was determined according to the method of Test Example 1. As control, water was used instead of said liniment and absorbance was measured in the same way.
Comparative Test Example 2 A liniment was prepared in the same way as Test Example 2 except that hydrogen peroxide was used instead of the compound obtained in Synthesis Example 1, and its tyrosinase activity inhibiting capacity was examined.
The test results are shown in Fig. 2. It will be understood from Fig. 2 that the liniment using the -- 10 _ 1 compound obtained in Synthesis Example 1 ls far higher in tyrosinase activity inhibiting performance than the liniment using hydrogen peroxide.
The compounds obtained in Synthesis Examples 2 - 5 also had the same degree of tyrosinase activity inhibitory action as the compound obtained in Synthesis Example 1.
Test Example 3 (Enzymatic decomposition of fatty acid ester of 4-isopropyltropolone) 1) Substrate solution:
A solution was prepared by mixing 2% of poly-vinyl alcohol in an M/15 phosphate buffer (pH 7.0), and the fatty acid esters were added respectively in this solution to a concentration of 0.05M and each solution was made into an emulsion by a homogenizer.
2) Enzyme solution:
30 mg of refined bacterial lipase was dissolved in 10 ml of water. The organ crude enzyme solution was prepared by triturating hair-shaven skin pieces and pancreas of rats with body weight of around 200 g and forming them into a solution.
1 1 62Sf;4 1 3) Reaction solution composition:
.~ Composition (ml) A B
Substrate emulsion 5.0 1.0 Buffer 4.0 1.0 Refined lipase 1.0 - -Organ triturated solution - 2.0 4) Method of measurement:
After one-hour incubation at 37C, the reaction was stopped with 5% metaphosphoric acid, and a~ter centrifugal precipitation, the supernatant was added with 0.5 ml of a ferric chloride reagent (0.1% aqueous solution) or a ferric sulfide reagent and color develop-ment (dark red) was observed. + indicates thin red, ++ indicates thick red, +++ indicates dark red, - indicates no color development, and + indicates unconfirmed color development.
5) Test results:
The test results are shown in the following table, from which it is evident that the fatty acid esters undergo enzymatic decomposition.
_ 12 -t ~ 6~56~
.
Substrate Degree of formatlon of 4-isopropyltropolone (fatty acid esters) Bacterial Homogenate lipase -- -(ref in ed) Rat skin Rat pancreas _ Acetylate + +++ +++
Palmitate + ~+ ++
Stearate + ~+ +
_ 1 Test Example 4 (~ffect o~ fatty acid esters of 4-isopropyl-tropolone on melanin formation in human skin) 2-palmitate and 2-stearate of 4-isopropyl-tropolone were used as the representative examples of the fatty acld esters of 4-isopropyltropolone, and these esters were respectively blended in a pharmaco-peial hydrophilic ointment. The ointment was applied to the melasma on human face three times a day and its effect was observed with the unaided eye. The results are shown in the following table. As control, a hydro-philic ointment (prepared according to the Japanese Pharmacopeia) alone was applied to the melasma on the other side of the face in the same way as said above.
'~ . to o J~
F~ ~ o ~ Lr~ ~r C~ o ~ o ~
~ E~
~ ~o Z;~ ~ ~ ~ a~
h ~d C~ O
OU~ ~ ~
h c~
a~ ~ Lr~ o o o td ~ ~ ~ ~1 ,1 ,1 O C~
z~n bD
O
u~ n ~ u~
O ~ ~ ~ S .C C~ O
t~ ~ ~ J~ ~ Ei U~ ~1 O ~ ~ ~0 ` ~0 0~ O
S~ ~ ~ ~ ' ~ O
I I I ~
o o o a ~ ~ ~ C~
I O O O ~ ~ U~
O h ~ ~ ~) ~ :~
h ~ J~ ~ ~ C~ o ~1 ~1 ~1 ~ ~ ~ a~ , u~ ~ O ~ a~o ~ ~ o ~ o a~ ~1 ~ ~ ~ E3~ ~ E ~ ~ o td e ~ E~
o e ~o e ~o ~1 ~~ ~ ~~q ~ Q.~ ~ ~ O~ ~ O~ J~ a a~ o o I ~I ~I ~q ~ J~
e t~ 5 I'a =~ I'd 5 I S: O
~ N 0~N ~N a~ Z
~ ~ e ~
~r1 S.1 r--l N Q
o ~ ~ o s: ~ o ~:
s ~ o ,i. o ~.
O ~i ,QO ~ D O--~ O
~ ~ 62564 l Exemplifled below are the possible prescrip=
tions of the skin-beautifying cosmetic preparations (total amount lO0 parts by weight) according to thls invention. Needless to say, the invention is not limited to these prescriptions.
Prescription Example l (Lotion) Components_ Parts by weight 4-isopropyltropolone 0.01 Aminoacetic acid 0.20 Pyridoxine hydrochloride 0.05 EDTA proper quantity Zinc phenolsulfonate 0.30 Propylene glycol 8.00 Ethanol 5.0 Refined water balance Perfume and antiseptic small quantities Prescription Example 2 (Pack) Components Parts by weight 4-isopropyltropolone 0.01 Stearlc acid 4.00 Aminoacetic acid 0.20 EDTA proper quantity Zinc phenolsulfonate 0.30 Propylene glycol 13.00 Carboxyv~nyl polymer 1.20 - ? 1 62564 Sodium hydroxlde 0.14 .Ethanol 2.50 Titanium oxide 0.02 Refined water balance Perfume and antiseptic small quantities Prescription Example 3 (Pack) Components Parts by weight 4-isopropyltropolone 0.01 Polyvinyl alcohol 15.00 Polyvinyl pyrrolidone 4.00 Stearic acid 2.00 "Tween 20~ * 2.00 "Span 60~** 0.500 E~TA proper quantity Propylene glycol 6.oo Ethanol 10.00 Refined water balance Perfume and antiseptic small quantities Prescription Example 4 (Milk lotion) Components Parts by weight 4-isopropyltropolone 0.01 Stearic acid 2.00 Cetanol 0.5G
EDTA proper quantity Hydrous lanolin 2.00 Oleyl oleate 2.00 * Trademark for polyoxyethylene (20) sorbitan monolaurate;
it is a nonionic surfactant.
** Trademark for sorbitan monostearate- it is a nonionic surfactant and emulsifier~
1 ~ ~2564 Squalane 3-Liquid paraffin 8.00 Emulsifier 2.60 Propylene glycol 4.00 Refined water balance Perfume, antioxidant and antiseptic small quantities Prescription Example 5 (Vanishing cream) Components Parts by weight 4-isopropyltropolone 0.01 MC stearic acid 8.00 Beeswax 5 Cetanol 3.00 Hydrous lanolin 2.00 Isopropyl myristate 6.oo Liquid paraffin 27~00 Olive oil . 2.00 EDTA proper quantity Emulsifier 5-50 Propylene glycol 3.00 Re~ined water balance Perfume, antioxidant and antiseptic small quantities Prescription Example 6 (Cold cream) Comporents Parts by weight 4-isopropyltropolone 0.01 Beeswax 10.00 Ceresine 7-~ ~ 62564 White petroleum jelly ~petrolatum~ 3 Hydrous lanolln 3.00 Isopropyl myristate 3.00 Squalane 4-0 Liquid paraffin 40.00 EDTA proper quantity Polyoxyethylene cetyl ether 2.70 Emulsifier 2.30 Propylene glycol 2.00 Refined water 23.00 Perfume, antioxidant and antiseptic small quantities Prescription Example 7 (Lotion) Components Parts by weight 2-caprylate of 4-isopropyltropo- o 01 lone Aminoacetic acid 0.20 Pyridoxine hydrochloride 0.05 Zinc phenolsulfonate 0.30 Propylene glycol 8.00 Ethanol . 5 Refined water balance Perfume and antiseptic small quantities Prescription Example 8 (Pack) Components Parts by weight 2-butyrate of 4-isopropyltropolone 0.01 Stearic acid 4.00 Aminoacetic acid 0.20 ~ ~ 62564 Zinc phenolsulfonate 0.30 Propylene glycol -13.00 .
Carboxyvinyl polymer 1.20 Emulsifier 3.00 Ethanol 2.50 Titanium oxide 0.02 Refined water balance Perfume and antisepticsmall quantities Prescription Example 9 (Pack) Components Parts by weight 2-palmitate of 4-isopropyltropolone 0.01 Polyvinyl alcohol 15.00 Polyvinyl pyrrolidone 4.00 Stearic acid 2.00 'iTween 20 " (trademark) 2.00 "Span 60 " (trademark) O . 50 Propylene glycol 6.00 Ethanol 10.00 Refined water balance Perfume and antisepticsmall quantities Prescription Example 10 (Milk lotion) - Components Parts by weight_ 2-caprylate of 4-isopropyltropolone 0.02 Stearic acid 2.00 Cetanol 5 Hydrous lanolin 2.00 1 ~ 62S64 Oleyl oleate 2.00 Squalane 3.00 Liquid paraffir~ 8.00 Emulsifier 2.60 Propylene glycol 4.00 Refined water balance Perfume~ antioxidant and antiseptic small quantities Prescription Example 11 (Vanishing cream) Components Parts by weight 2-butyrate of 4-isopropyltropolone 0.01 MC stearic acid 8.00 Beeswax 5 Cetanol 3.00 Hydrous lanolin 2.00 Isopropyl myristate 6.oo Liquid paraffin 7.00 Olive oil 2.00 Emulsifier 5.50 Propylene glycol 3.O
Refined water balance Perfume, antioxidant and antiseptic small quantities Prescription Example 12 (Cold cream) Components Parts by weight 2-palmitate of 4-isopropyltropolone 0.01 Beeswax 10.00 Ceresine 7-~ ~625~4 White petroleum jelly (petrolatum) 3 Hydrous lanolln 3.00 Isopropyl myristate 3.00 Squalane 4 0 Liquid paraffin 40.00 Polyoxyethylene cetyl ether 2.70 Emulsifier 2.30 Propylene glycol 2.00 Refined water balance Perfume, antioxidant and antiseptic small quantities 1 Effect Test Example l A panel test on the skin-beautifying effect was conducted by using a vanishin~ cream produced accord-ing to Prescription Example 5. Twenty woman volunteers all had facial pigmental abnormalities, and of them, 18 had spots (malesma) and 2 had freckles on their faces. In the test, said vanishing cream was applied to the right half of the face of each subject and the cream same as said above but not containing 4-isopropyltropolone was applied to the left half of the face, both being applied twice a day (morning and evening) for a period of 12 weeks.
^ The results showed 1 case of "salient effect",
Elemental analysis:
Calculated: C, 69.88%, H, 6.84%
Found: C, 69.48%; H, 6.82%
Synthesis Example 5 (2-stearate of 4-isopropyltropolone) 16.4 g of 4-isopropyltropolone was dissolved in 300 ml of pyridine, added with 30.3 g of stearoyl chlorlde under stlrrlng at room temperature and treated according to Synthesis ~xampie 1 to obtain 35.0 g o~
white crystals (yield: 80.0%). This product is 2-stearate o~ 4-isopropyltropolone.
Melting point: 39 - 40C
Elemental analysis:
Calculated C, 78.o8%~ H, 10.77%
Found: C, 78.00%; H, 10.78%
Rf (measured in the same way as in the case 1 of palmitate): 0.941.
~.
Test Example 1 0.05 g of 4 isopropyltropolone was dissolved in a 30% ethanol-water mixture, and then 0.03% of EDTA
was added and dissolved therein. After ad~usting the pH of the solution by using succinic acid and potassium carbonate, water was added thereto to make the total amount 100 parts. Ihere was obtained a liniment with a 4-isopropyltropolone concentration of 0.05%.
The tyrosinase activity inhibiting ability of the thus obtained liniment was examined in the follow-ing way.
1 ml of an L-tyrosine solution (0.3 mg/ml), 1 ml of Macllvaine's buffer (pH 6.8) and 0.9 ml of said liniment were added into a test tube and incubated in a 37C temperature-controlled water bath for 10 minutes. The mixture was then added with 0.1 ml of a tyrosinase solution (0.3 mg/ml) and stirred well, and then immediately a spectrophotometer was set and the absorbance at 475 m~ was measured with passage of time.
As control, a similar mixed solution was prepared by using a 30% ethanol solution instead of said liniment and its absorbance was measured in the same way.
Comparative Test Example 1 A 0.05~ concentration liniment was prepared in the same way as Test Example 1 except for use of 11 625~4 1 colchicine inste~d of 4-isopropyltropolone, and its tyrosinase activity inhibiting capacity was examined.
The test results of said Test Example 1 and Comparative Test Example 1 are shown in Fig. 1. It will be appreciated from Fig. 1 that the liniment obtained in Test Example 1 has far higher tyrosinase activity inhibiting ability than the liniment obtained in Com-parative Test Example 1.
Test Example 2 The compound obtained in Synthesis Example 1 was dissolved in ethanol and then the pH of the solution was ad~usted to 6.3 with succinic acid or potassium carbonate to obtain a liniment with a 1.0% concentration.
The tyrosinase activlty inhibiting performance of this liniment was determined according to the method of Test Example 1. As control, water was used instead of said liniment and absorbance was measured in the same way.
Comparative Test Example 2 A liniment was prepared in the same way as Test Example 2 except that hydrogen peroxide was used instead of the compound obtained in Synthesis Example 1, and its tyrosinase activity inhibiting capacity was examined.
The test results are shown in Fig. 2. It will be understood from Fig. 2 that the liniment using the -- 10 _ 1 compound obtained in Synthesis Example 1 ls far higher in tyrosinase activity inhibiting performance than the liniment using hydrogen peroxide.
The compounds obtained in Synthesis Examples 2 - 5 also had the same degree of tyrosinase activity inhibitory action as the compound obtained in Synthesis Example 1.
Test Example 3 (Enzymatic decomposition of fatty acid ester of 4-isopropyltropolone) 1) Substrate solution:
A solution was prepared by mixing 2% of poly-vinyl alcohol in an M/15 phosphate buffer (pH 7.0), and the fatty acid esters were added respectively in this solution to a concentration of 0.05M and each solution was made into an emulsion by a homogenizer.
2) Enzyme solution:
30 mg of refined bacterial lipase was dissolved in 10 ml of water. The organ crude enzyme solution was prepared by triturating hair-shaven skin pieces and pancreas of rats with body weight of around 200 g and forming them into a solution.
1 1 62Sf;4 1 3) Reaction solution composition:
.~ Composition (ml) A B
Substrate emulsion 5.0 1.0 Buffer 4.0 1.0 Refined lipase 1.0 - -Organ triturated solution - 2.0 4) Method of measurement:
After one-hour incubation at 37C, the reaction was stopped with 5% metaphosphoric acid, and a~ter centrifugal precipitation, the supernatant was added with 0.5 ml of a ferric chloride reagent (0.1% aqueous solution) or a ferric sulfide reagent and color develop-ment (dark red) was observed. + indicates thin red, ++ indicates thick red, +++ indicates dark red, - indicates no color development, and + indicates unconfirmed color development.
5) Test results:
The test results are shown in the following table, from which it is evident that the fatty acid esters undergo enzymatic decomposition.
_ 12 -t ~ 6~56~
.
Substrate Degree of formatlon of 4-isopropyltropolone (fatty acid esters) Bacterial Homogenate lipase -- -(ref in ed) Rat skin Rat pancreas _ Acetylate + +++ +++
Palmitate + ~+ ++
Stearate + ~+ +
_ 1 Test Example 4 (~ffect o~ fatty acid esters of 4-isopropyl-tropolone on melanin formation in human skin) 2-palmitate and 2-stearate of 4-isopropyl-tropolone were used as the representative examples of the fatty acld esters of 4-isopropyltropolone, and these esters were respectively blended in a pharmaco-peial hydrophilic ointment. The ointment was applied to the melasma on human face three times a day and its effect was observed with the unaided eye. The results are shown in the following table. As control, a hydro-philic ointment (prepared according to the Japanese Pharmacopeia) alone was applied to the melasma on the other side of the face in the same way as said above.
'~ . to o J~
F~ ~ o ~ Lr~ ~r C~ o ~ o ~
~ E~
~ ~o Z;~ ~ ~ ~ a~
h ~d C~ O
OU~ ~ ~
h c~
a~ ~ Lr~ o o o td ~ ~ ~ ~1 ,1 ,1 O C~
z~n bD
O
u~ n ~ u~
O ~ ~ ~ S .C C~ O
t~ ~ ~ J~ ~ Ei U~ ~1 O ~ ~ ~0 ` ~0 0~ O
S~ ~ ~ ~ ' ~ O
I I I ~
o o o a ~ ~ ~ C~
I O O O ~ ~ U~
O h ~ ~ ~) ~ :~
h ~ J~ ~ ~ C~ o ~1 ~1 ~1 ~ ~ ~ a~ , u~ ~ O ~ a~o ~ ~ o ~ o a~ ~1 ~ ~ ~ E3~ ~ E ~ ~ o td e ~ E~
o e ~o e ~o ~1 ~~ ~ ~~q ~ Q.~ ~ ~ O~ ~ O~ J~ a a~ o o I ~I ~I ~q ~ J~
e t~ 5 I'a =~ I'd 5 I S: O
~ N 0~N ~N a~ Z
~ ~ e ~
~r1 S.1 r--l N Q
o ~ ~ o s: ~ o ~:
s ~ o ,i. o ~.
O ~i ,QO ~ D O--~ O
~ ~ 62564 l Exemplifled below are the possible prescrip=
tions of the skin-beautifying cosmetic preparations (total amount lO0 parts by weight) according to thls invention. Needless to say, the invention is not limited to these prescriptions.
Prescription Example l (Lotion) Components_ Parts by weight 4-isopropyltropolone 0.01 Aminoacetic acid 0.20 Pyridoxine hydrochloride 0.05 EDTA proper quantity Zinc phenolsulfonate 0.30 Propylene glycol 8.00 Ethanol 5.0 Refined water balance Perfume and antiseptic small quantities Prescription Example 2 (Pack) Components Parts by weight 4-isopropyltropolone 0.01 Stearlc acid 4.00 Aminoacetic acid 0.20 EDTA proper quantity Zinc phenolsulfonate 0.30 Propylene glycol 13.00 Carboxyv~nyl polymer 1.20 - ? 1 62564 Sodium hydroxlde 0.14 .Ethanol 2.50 Titanium oxide 0.02 Refined water balance Perfume and antiseptic small quantities Prescription Example 3 (Pack) Components Parts by weight 4-isopropyltropolone 0.01 Polyvinyl alcohol 15.00 Polyvinyl pyrrolidone 4.00 Stearic acid 2.00 "Tween 20~ * 2.00 "Span 60~** 0.500 E~TA proper quantity Propylene glycol 6.oo Ethanol 10.00 Refined water balance Perfume and antiseptic small quantities Prescription Example 4 (Milk lotion) Components Parts by weight 4-isopropyltropolone 0.01 Stearic acid 2.00 Cetanol 0.5G
EDTA proper quantity Hydrous lanolin 2.00 Oleyl oleate 2.00 * Trademark for polyoxyethylene (20) sorbitan monolaurate;
it is a nonionic surfactant.
** Trademark for sorbitan monostearate- it is a nonionic surfactant and emulsifier~
1 ~ ~2564 Squalane 3-Liquid paraffin 8.00 Emulsifier 2.60 Propylene glycol 4.00 Refined water balance Perfume, antioxidant and antiseptic small quantities Prescription Example 5 (Vanishing cream) Components Parts by weight 4-isopropyltropolone 0.01 MC stearic acid 8.00 Beeswax 5 Cetanol 3.00 Hydrous lanolin 2.00 Isopropyl myristate 6.oo Liquid paraffin 27~00 Olive oil . 2.00 EDTA proper quantity Emulsifier 5-50 Propylene glycol 3.00 Re~ined water balance Perfume, antioxidant and antiseptic small quantities Prescription Example 6 (Cold cream) Comporents Parts by weight 4-isopropyltropolone 0.01 Beeswax 10.00 Ceresine 7-~ ~ 62564 White petroleum jelly ~petrolatum~ 3 Hydrous lanolln 3.00 Isopropyl myristate 3.00 Squalane 4-0 Liquid paraffin 40.00 EDTA proper quantity Polyoxyethylene cetyl ether 2.70 Emulsifier 2.30 Propylene glycol 2.00 Refined water 23.00 Perfume, antioxidant and antiseptic small quantities Prescription Example 7 (Lotion) Components Parts by weight 2-caprylate of 4-isopropyltropo- o 01 lone Aminoacetic acid 0.20 Pyridoxine hydrochloride 0.05 Zinc phenolsulfonate 0.30 Propylene glycol 8.00 Ethanol . 5 Refined water balance Perfume and antiseptic small quantities Prescription Example 8 (Pack) Components Parts by weight 2-butyrate of 4-isopropyltropolone 0.01 Stearic acid 4.00 Aminoacetic acid 0.20 ~ ~ 62564 Zinc phenolsulfonate 0.30 Propylene glycol -13.00 .
Carboxyvinyl polymer 1.20 Emulsifier 3.00 Ethanol 2.50 Titanium oxide 0.02 Refined water balance Perfume and antisepticsmall quantities Prescription Example 9 (Pack) Components Parts by weight 2-palmitate of 4-isopropyltropolone 0.01 Polyvinyl alcohol 15.00 Polyvinyl pyrrolidone 4.00 Stearic acid 2.00 'iTween 20 " (trademark) 2.00 "Span 60 " (trademark) O . 50 Propylene glycol 6.00 Ethanol 10.00 Refined water balance Perfume and antisepticsmall quantities Prescription Example 10 (Milk lotion) - Components Parts by weight_ 2-caprylate of 4-isopropyltropolone 0.02 Stearic acid 2.00 Cetanol 5 Hydrous lanolin 2.00 1 ~ 62S64 Oleyl oleate 2.00 Squalane 3.00 Liquid paraffir~ 8.00 Emulsifier 2.60 Propylene glycol 4.00 Refined water balance Perfume~ antioxidant and antiseptic small quantities Prescription Example 11 (Vanishing cream) Components Parts by weight 2-butyrate of 4-isopropyltropolone 0.01 MC stearic acid 8.00 Beeswax 5 Cetanol 3.00 Hydrous lanolin 2.00 Isopropyl myristate 6.oo Liquid paraffin 7.00 Olive oil 2.00 Emulsifier 5.50 Propylene glycol 3.O
Refined water balance Perfume, antioxidant and antiseptic small quantities Prescription Example 12 (Cold cream) Components Parts by weight 2-palmitate of 4-isopropyltropolone 0.01 Beeswax 10.00 Ceresine 7-~ ~625~4 White petroleum jelly (petrolatum) 3 Hydrous lanolln 3.00 Isopropyl myristate 3.00 Squalane 4 0 Liquid paraffin 40.00 Polyoxyethylene cetyl ether 2.70 Emulsifier 2.30 Propylene glycol 2.00 Refined water balance Perfume, antioxidant and antiseptic small quantities 1 Effect Test Example l A panel test on the skin-beautifying effect was conducted by using a vanishin~ cream produced accord-ing to Prescription Example 5. Twenty woman volunteers all had facial pigmental abnormalities, and of them, 18 had spots (malesma) and 2 had freckles on their faces. In the test, said vanishing cream was applied to the right half of the face of each subject and the cream same as said above but not containing 4-isopropyltropolone was applied to the left half of the face, both being applied twice a day (morning and evening) for a period of 12 weeks.
^ The results showed 1 case of "salient effect",
3 cases of "noticeable effect", 10 cases of "slightly noticeable effect" and 6 cases of "little change". Thus, after all, effectiveness was confirmed on 70% of the sub~ects. These results imply the possibility of 1 furthered skin-beautifying effect by continuous use of s~id cream for a longer period of time.
In actual applications of the composition of thls lnvention, ln case it is used as cosmetics, lt is desirable to reduce the concentratlon of 4-isopropyl-tropolone or a fatty acid ester thereof, and in case it is used for the purpose of treatment of a skin disease, it is suggested to increase the concentration of said substance as far as no undesirable stimulus is given.
In actual applications of the composition of thls lnvention, ln case it is used as cosmetics, lt is desirable to reduce the concentratlon of 4-isopropyl-tropolone or a fatty acid ester thereof, and in case it is used for the purpose of treatment of a skin disease, it is suggested to increase the concentration of said substance as far as no undesirable stimulus is given.
Claims (6)
1. Fatty acid esters of 4-isopropyltropolone represented by the formula:
wherein R is a hydrocarbon group having 1 to 18 carbon atoms.
wherein R is a hydrocarbon group having 1 to 18 carbon atoms.
2. The fatty acid esters of 4-isopropyltropolone according to claim 1, wherein said fatty acid esters are the esters of acetic acid, butyric acid, caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid or oleic acid.
3. A skin-beautifying cosmetic composition containing as active ingredient a fatty acid ester of 4-isopropyltropolone represented by the formula wherein R is a hydrocarbon group having 1 to 18 carbon atoms, the balance of said composition comprising materials conventionally employed in cosmetic compositions.
4. A composition as in claim 3 wherein said fatty acid esters are the esters of acetic acid, butyric acid, caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid or oleic acid.
5. The composition of claim 3 wherein the content of said active ingredient is from 0.0001% to 10% by weight.
6. The composition of claim 3 wherein the fatty acid ester of 4-isopropyltropolone is a palmitic acid ester as stearic acid ester.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10128279A JPS5626842A (en) | 1979-08-10 | 1979-08-10 | Aliphatic acid ester of beta-thujaplicin and fair-skinning cosmetic having said ester as active component |
GB8040983A GB2089785B (en) | 1979-08-10 | 1980-12-22 | Isopropyl tropolone derivatives and their use in skin bleaching cosmetic compositions |
DE3049123A DE3049123C2 (en) | 1979-08-10 | 1980-12-24 | FATTY ACID ESTER OF 4-ISOPROPYLTROPOLON AND SKIN-BEAUTIFULING, COSMETIC AGENT |
FR8027559A FR2496642B1 (en) | 1979-08-10 | 1980-12-24 | |
CA000427867A CA1162564A (en) | 1979-08-10 | 1983-05-10 | Skin-beautifying cosmetic composition |
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10128279A JPS5626842A (en) | 1979-08-10 | 1979-08-10 | Aliphatic acid ester of beta-thujaplicin and fair-skinning cosmetic having said ester as active component |
GB8040983A GB2089785B (en) | 1979-08-10 | 1980-12-22 | Isopropyl tropolone derivatives and their use in skin bleaching cosmetic compositions |
CA000367441A CA1156152A (en) | 1979-08-10 | 1980-12-23 | Skin-beautifying cosmetic composition |
DE3049123A DE3049123C2 (en) | 1979-08-10 | 1980-12-24 | FATTY ACID ESTER OF 4-ISOPROPYLTROPOLON AND SKIN-BEAUTIFULING, COSMETIC AGENT |
FR8027559A FR2496642B1 (en) | 1979-08-10 | 1980-12-24 | |
US06/221,007 US4361581A (en) | 1979-08-10 | 1980-12-29 | Skin-beautifying cosmetic composition |
CA000427867A CA1162564A (en) | 1979-08-10 | 1983-05-10 | Skin-beautifying cosmetic composition |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1162564A true CA1162564A (en) | 1984-02-21 |
Family
ID=27560906
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA000427867A Expired CA1162564A (en) | 1979-08-10 | 1983-05-10 | Skin-beautifying cosmetic composition |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPS5626842A (en) |
CA (1) | CA1162564A (en) |
DE (1) | DE3049123C2 (en) |
FR (1) | FR2496642B1 (en) |
GB (1) | GB2089785B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4202964A1 (en) * | 1992-02-01 | 1993-08-05 | Wella Ag | HAIR AND BODY TREATMENT |
TW233264B (en) * | 1992-02-03 | 1994-11-01 | Otsuka Pharma Co Ltd | |
JP2002179549A (en) * | 2000-12-12 | 2002-06-26 | Kishohin Kagaku Kaiho Kenkyusho:Kk | Skin care preparation |
CN114163322B (en) * | 2021-11-23 | 2023-09-12 | 中国农业科学院农业环境与可持续发展研究所 | Ultraviolet absorber, preparation method and application |
CN114436909B (en) * | 2022-01-26 | 2023-05-30 | 河南科技大学 | Sulfonyl sabinol derivative and preparation method and application thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4994816A (en) * | 1973-01-27 | 1974-09-09 | ||
JPS50123814A (en) * | 1974-02-09 | 1975-09-29 | ||
JPS5129469A (en) * | 1974-09-03 | 1976-03-12 | Akira Kafuku | Hinokichiooruno kayokaho |
JPS568309A (en) * | 1979-06-29 | 1981-01-28 | Yasuaki Fukuda | White cosmetic |
-
1979
- 1979-08-10 JP JP10128279A patent/JPS5626842A/en active Pending
-
1980
- 1980-12-22 GB GB8040983A patent/GB2089785B/en not_active Expired
- 1980-12-24 DE DE3049123A patent/DE3049123C2/en not_active Expired
- 1980-12-24 FR FR8027559A patent/FR2496642B1/fr not_active Expired
-
1983
- 1983-05-10 CA CA000427867A patent/CA1162564A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR2496642A1 (en) | 1982-06-25 |
DE3049123A1 (en) | 1982-07-15 |
JPS5626842A (en) | 1981-03-16 |
DE3049123C2 (en) | 1988-01-21 |
GB2089785A (en) | 1982-06-30 |
FR2496642B1 (en) | 1985-11-08 |
GB2089785B (en) | 1985-07-17 |
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