GB2089785A - Isopropyltropolone derivatives and their use in skin bleaching cosmetic compositions - Google Patents
Isopropyltropolone derivatives and their use in skin bleaching cosmetic compositions Download PDFInfo
- Publication number
- GB2089785A GB2089785A GB8040983A GB8040983A GB2089785A GB 2089785 A GB2089785 A GB 2089785A GB 8040983 A GB8040983 A GB 8040983A GB 8040983 A GB8040983 A GB 8040983A GB 2089785 A GB2089785 A GB 2089785A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isopropyltropolone
- cosmetic composition
- composition according
- acid
- 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.)
- Granted
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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
4-Isopropyltropolone having the formula: <IMAGE> and/or the fatty acid esters thereof having the formula: <IMAGE> (wherein R is a hydrocarbon group having 1 to 18 carbon atoms) have the excellent skin-beautifying and anti-suntan effects and are usable as active ingredients for the skin-beautifying cosmetics. The fatty acid esters of 4-isopropyltropolone are novel substances.
Description
SPECIFICATION
Skin-beautifying cosmetic composition
BACKGROUND OF THE INVENTION
FIELD OF THE INVENTION
This invention relates to a skin beautifying cosmetic composition, more particularly a skin beautifying cosmetic composition containing 4-isopropyltrpolone 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 live up to such feminine desire. However, the peroxides such as mentioned above had the problems in keeping quality, physical or chemical stability and blending compatibility with the cosmetic compositions, and also their skin-beautifying effect was unsatisfactory. There have been developed and commonly used lately the cosmetics blended with vitamin C, cystine, colloidal sulfur and the like, but even these cosmetics can not still be deemed satisfactory in keeping quality, stability and beautifying effect.
SUMMARY OF THE INVENTION
An object 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 ingredient for the skin-beautifying and whitening cosmetic preparations.
As a result of extensive studies in search for a cosmetic agent which has no side effects unfavorable to the human body and yet can produce the excellent skin-beautifying and suntan preventive effects, this inventor found out the new facts that 4-isopropyltropolone having the formula:
and/or the fatty acid esters thereof having the formula::
(wherein R is a hydrocarbon group having 1 to 1 8 carbon atoms) can produce a marvelous skin-beautifying effect as well as a splended suntan preventive effect as they have an inhibitory action against activity of 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 excellent 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 damaging to the skin.
BRIEF DESCRIPTION OF THE DRAWINGS
Figure 1 is a graph showing the relation between degree of pigmentation and time for illustrating the tyrosinase activity inhibiting ability of the liniment obtained in Test 1.
Figure 2 is a graph showing the relation between degree of pigmentation and time for illustrating the tyrosinase activity inhibiting ability of 4-isopropyltropolone prepared by hydrolyzing the liniment obtained in Test 2 with Na2CO3.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The skin-beautifying cosmetic composition of this invention has as its active ingredients 4isopropyltropolone and/or a fatty acid ester thereof blended in a base, and these active ingredients are usually contained in an amount of about 0.0001 to 10% by weight, preferably about 0.001 to 5% by weight. A well satisfactory skin-beautifying effect and anti-suntan effect are provided from the said range of content of the active ingredients, but it should be noted that if said active ingredients are contained in excess of 10%, no corresponding merit is derived, while 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-isopropyltropolone, if its activity site is blocked by a metal, it loses its tyrosinase activity inhibitory action. In fact, in the presence of 1 pm 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-isopropyltropolone loses its tyrosinase activity inhibitory action. In order to eliminate obstruction by such metal ions against the tyrosinase activity inhibitory action, it is suggested to add to 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 esterification reaction with 4-isopropyltropolone in this invention, there are employed those having 2 to 1 9 carbon atoms, the typical examples thereof being butyric acid, caproic acid, caprylic acid, lauric acid, myristic acid, acetic acid, palmitic acid, stearic acid, and oletic acid.
The thus obtained fatty acids esters of 4-isopropyltropolone are the 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 finds optimal applications as a skin-beautifying agent and anti-suntan agent, and thus the skin-beautifying cosmetic composition of this invention containing said 4-isopropyltropolone or a fatty acid ester thereof as active ingredient has eliminated the inherent defects of the conventional cosmetic preparations of this type and is not subject 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 as stabilizer, pigment, aromatic, 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 all other considerable forms.
The skin-beautifying cosmetic preparations 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 70"C for 30 minutes and then allowed to cool by itself to 0 C 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 removed, 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 - 28"C IR (KBr): 1760 cm-' (C = 0); 1660 cm-1 (C=O) Elemental analysis:
Calculated: C, 77.61; H, 10.45
Found: C,77.12; H, 10.42
0.1 g of this product was dissolved in 10 ml of ethanol and this solution was tested by T. L.C.
(eluant: ether/benzene/ethanol/acetic acid = 40/50/2/0.2; colour producing reagent: ferric sulphide). One spot was detected at Rf = 0.924.
Synthesis Example 2 (2-butyrate of 4-isopropyltropolone) 1 6.4 g of 4-isopropyltropolone was dissolved in 300 ml of pyridine and the mixture, while cooled with ice, was added with 10.66 g of n-butyryl chloride under stirring, heated at room temperature for 30 minutes and then allowed to cool naturally to OoC for one hour. This mixture was then treated similarly to Synthesis Example 1 to obtain 17.57 g of white crystals (yield: 75%). This product is 2-butyrate of 4-isopropyltropolone.
IR (KBr): 1763 cm-l (C = 0); 1658 cm-' (C = 0)
Elemental analysis:
Calculated: C, 71.17%, H, 7.74%
Found: C, 71.10%; H, 7.71%
Synthesis Example 3 (2-caprylate of 4-isopropyltropolone) 1 6.4 g of 4-isopropyltropolone was dissolved in 300 ml of pyridine and then further added with 16.27 g of capryl chloride (octanoyl chloride) while cooling with ice and under stirring, 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 4isopropyltropolone.
IR (KBr): 1765 cm ' (C = 0); 1660 cm-' (C = 0)
Elemental analysis:
Calculated: C, 74.45%; H, 9.02%
Found: C, 74.25%; H, 9.26%
Synthesis Example 4 (2-acetate of 4-isopropyltropolone)
16.4 g of 4-isopropyltropolone was dissolved in 300 ml of pyridine, then added with 7.85 9 of acetyl chloride under ice cooling and stirring and subjected 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 if 4-isopropyltropolone)
16.4 g of 4-isopropyltropolone was dissolved in 300 ml of pyridine, added with 30.3 g of stearoyl chloride under stirring at room temperature and treated according to Synthesis Example 1 to obtain 35.0 g of white crystals (yield: 80.0%). This product is 2-stearate of 4isopropyltropolone.
Melting point: 39 - 40"C Elemental analysis:
Calculated: C, 78.08%; H, 10.77%
Found: C, 78.00%; H, 10.78%
Rf (measured in the same way as in the case 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 adjusting pH of the solution by using succinic acid and potassium carbonate, water was added thereto to make the total amount 100 parts. There 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 following 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 37"C 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 my 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 colchicine instead 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 Comparative Test Example 1.
Test Example 2
The compound obtained in Synthesis Example 1 was dissolved in ethanol and then pH of the solution was adjusted to 6.0 with succinic acid or potassium carbonate to obtain a liniment with a 1.0% concentration.
The tyrosinase activity 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 compound obtained in Synthesis Example 1 is far higher in tyrosinase activity inhibiting performance than the liniment using hydrogen peroxide.
The compounds obtained in Synthesis Examples 2 - 5 also had a 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 polyvinyl 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 the hair-shaven skin pieces and pancreas of the rats with the body weight of around 200 g and forming them into a solution.
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 37"C, the reaction was stopped with 5% metaphosphoric acid, and after 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 development (dark red) was observed. + indicates thin red, + + indicates thick red, + + + indicates dark red, indicates no color development, and j 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.
Degree of formation of 4
isopropyltropolone
Substrate Bacterial Honogenate (fatty acid lipase esters) (refined) Rat skin Rat pancreas
Acetylate + +++ +++
Palmitate + + + + +
Stearate + + + +
Test Example 4 (Effect of fatty acid esters of 4isopropyltropolone on melanin formation in human skin)
2-palmitate and 2-stearate of 4-isopropyltropolone were used as the representative examples of the fatty acid esters of 4-isopropyltropolone, and these esters were respectively blended in a pharmacopeial 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 hydrophilic 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.
Effect
Ointment tested Period of Number of
application subjects No Took Marvelous
effect effect effect
Pharmacopeial hydrophilic ointment 3 months 1 5 1 5 0 0 0.02% 4-isopropyltropolone-2-palmitate 3 months 10 3 3 4 blended ointment 0.05% 4-isopropyltropolone-2-palmitate 3 months 10 0 5 5 blended ointment 0.05% 4-isopropyltropolone-2-stearate blended 3 months 10 1 5 4 ointment
(Note) Took effect: Obvious fading of dark color
Marvelous effect:
Almost perfect disappearance of melanin.
Exemplified below are the possible prescriptions of the skin-beautifying cosmetic preparations (total amount 100 parts by weight) according to this invention. Needless to say, the invention is not limited to these prescriptions.
Prescription Example 1 (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 5.00
Refined water balance
Perfume and antiseptic small quantities
Prescription Example 2 (Pack) (Pasty cosmetic placed on or wrapped around face)
Components Parts by weight 4-isopropyltropolone 0.01
Stearic acid 4.00
Aminoacetic acid 0.20
EDTA proper quantity
Zinc phenolsulfonate 0.30
Propylene glycol 1 3.00
Carboxyvinyl polymer 1.20
Sodium hydroxide 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
EDTA proper quantity
Propylene glycol 6.00
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 0.50
EDTA proper quantity
Hydrous lanolin 2.00
Oleyl oleate 2.00
Squalane 3.00
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 5.00
Cetanol 3.00
Hydrous lanolin 2.00
Isopropyl myristate 6.00
Liquid paraffin 27.00
Olive oil 2.00
EDTA proper quantity
Emulsifier 5.50
Propylene glycol 3.00
Refined water balance
Perfume, antioxidant and antiseptic small quantities
Prescription Example 6 (Cold cream)
Components Parts by weight 4-isopropyltropolone 0.01
Beeswax 10.00
Ceresine 7.00
White vaseline 3.00
Hydrous lanolin 3.00
Isopropyl myristate 3.00
Squalane 4.00
Liquid paraffin 40.00
EDTA proper quantity
Polyoxyethylene cetyl ether 2.70
Emulsifier 2.30
Propylene glycol 2.00
Refined water 23.00
Perfume, antixoidant and antiseptic small quantities
Prescription Example 7 (Lotion)
Components Parts by weight 2-caprylate of 4-isopropyltropo- 0.01 lene
Aminoacetic acid 0.20
Pyridoxine hydrochloride 0.05
Zinc phenolsulfonate 0.30
Propylene glycol 8.00
Ethanol 5.00
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
Zinc phenolsulfonate 0.30
Propylene glycol 1 3.00
Carboxyvinyl polymer 1.20
Emulsifier 3.00
Ethanol 2.50
Titanium oxide 0.02
Refined water balance
Perfume and antiseptic small 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
Tween 20 2.00
Span 60 0.50
Propylene glycol 6.00
Ethanol 10.00
Refined water balance
Perfume and antiseptic small quantities
Prescription Example 10 (Milk lotion)
Components Parts by weight 2-caprylate of 4-isopropyltropolone 0.02
Stearic acid 2.00
Cetanol 0.50
Hydrous lanolin 2.00
Oleyl oleate 2.00
Squalane 3.00
Liquid paraffin 8.00
Emulsifier 2.60
Propylene glycol 4.00
Refined water balance
Perfume, antioxidant and antiseptic small quantities
Prescription Example ii (Vanishing cream)
Components Parts by weight 2-butyrate of 4-isopropyltropolone 0.01
MC stearic acid 8.00
Beeswax 5.00
Cetanol 3.00
Hydrous lanolin 2.00
Isopropyl myristate 6.00
Liquid paraffin 7.00
Olive oil 2.00
Emulsifier 5.50
Propylene glycol 3.00
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 7.00
White vaseline 3.00
Hydrous lanolin 3.00
Isopropyl myristate 3.00
Squalane 4.00
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
Effect Test Example 1
A panel test on the skin-beautifying effect was conducted by using a vanishing cream produced according to Prescription Example 5. Twenty woman volunteers all had facial pigmental abnormalities, and of them, 10 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 1 2 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 subjects. These results imply the possibility of furthered skinbeautifying effect by continuous use of said cream for a longer period of time.
In actual applications of the composition of this invention, in case it is used as cosmetics, it is desirable to reduce the concentration of 4-isopropyltropolone 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 (14)
1. A fatty acid ester of 4-isopropyltropolone represented by the general formula:
wherein R is a hydrocarbon group having 1 to 1 8 carbon atoms.
2. A fatty acid ester of 4-isopropyltropolone according to claim 1, wherein said fatty acid ester is the ester of acetic acid, butyric acid, caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid or oleric acid.
3. A skin-beautifying cosmetic composition comprising (i) as active ingredient, 4-isopropyltropolone having the formula:
and/or a fatty acid ester thereof having the formula:
(wherein R is a hydrocarbon group having 1 to 1 8 carbon atoms), and (ii) a suitable carrier.
4. A cosmetic composition according to claim 3, wherein the content of said active ingredient is 0.0001 to 10% by weight.
5. A cosmetic composition according to claim 4, wherein the content of said active ingredient is 0.001 to 5% by weight.
6. A cosmetic composition according to any one of claims 3 to 5, which contains 4isopropyltropolone and is substantially free of metal ions.
7. A cosmetic composition according to any one of claims 3 to 5, which contains 4isopropyltropolone and is substantially free of Fe(lll) and Cu(ll) ions.
8. A cosmetic composition according to any one of claims 3 to 5. which contains 4isopropyltropolone and a sequestering agent.
9. A cosmetic composition according to claim 8, which includes EDTA in an amount of from 0.01 to 0.05% by weight calculated on the total weight of the composition.
10. A cosmetic composition according to any one of claims 3 to 9, which includes an alcohol, animal or vegetable fat, surfactant, pectin, carboxymethyl cellulose, alginate, stabiliser, pigment or perfume or two or more such ingredients.
11. A cosmetic composition according to any one of claims 3 to 10, wherein the carrier comprises an oil.
1 2. A cosmetic composition according to any one of claims 3 to 11, which is in the form of a liquid, cream or powder.
1 3. A cosmetic composition according to any one of claims 3 to 12, wherein the fatty acid ester of 4-isopropyltropolone is the palmitic acid ester or stearic acid ester.
14. A cosmetic composition according to claim 3, having a composition substantially as described in any one of Prescription Examples 1 to 1 2 herein.
1 5. A process for the preparation or a compound according to claim 1, which comprises esterifying 4-isopropyltropolone.
1 6. A process according to claim 15, wherein 4-isopropyltropolone is esterified by means of a chloride of the general formula RCOC1, wherein R has the meaning given in claim 1, in the presence of pyridine.
1 7. A process according to claim 15, carried out substantially as described in any one of
Synthesis Examples 1 to 5 herein.
1 8. A compound according to claim 1, whenever prepared by a process according to any one of claims 15 to 17.
Priority Applications (6)
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 | |
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 (2)
Publication Number | Publication Date |
---|---|
GB2089785A true GB2089785A (en) | 1982-06-30 |
GB2089785B GB2089785B (en) | 1985-07-17 |
Family
ID=27560906
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB8040983A Expired GB2089785B (en) | 1979-08-10 | 1980-12-22 | Isopropyl tropolone derivatives and their use in skin bleaching cosmetic compositions |
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) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0583479A1 (en) * | 1992-02-03 | 1994-02-23 | Otsuka Pharmaceutical Co., Ltd. | Remedy for dermatopathy and metallothionein inducer |
EP1214926A1 (en) * | 2000-12-12 | 2002-06-19 | Kabushiki Kaisha Kishohin Kagaku Kaiho Kenkyujo | Topical composition |
CN114163322A (en) * | 2021-11-23 | 2022-03-11 | 中国农业科学院农业环境与可持续发展研究所 | Ultraviolet absorbent, preparation method and application |
CN114436909A (en) * | 2022-01-26 | 2022-05-06 | 河南科技大学 | Sulfonyl hinokitiol derivative and its prepn and application |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4202964A1 (en) * | 1992-02-01 | 1993-08-05 | Wella Ag | HAIR AND BODY TREATMENT |
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
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0583479A1 (en) * | 1992-02-03 | 1994-02-23 | Otsuka Pharmaceutical Co., Ltd. | Remedy for dermatopathy and metallothionein inducer |
EP0583479A4 (en) * | 1992-02-03 | 1996-10-16 | Otsuka Pharma Co Ltd | Remedy for dermatopathy and metallothionein inducer |
EP1214926A1 (en) * | 2000-12-12 | 2002-06-19 | Kabushiki Kaisha Kishohin Kagaku Kaiho Kenkyujo | Topical composition |
CN114163322A (en) * | 2021-11-23 | 2022-03-11 | 中国农业科学院农业环境与可持续发展研究所 | Ultraviolet absorbent, preparation method and application |
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 |
CN114436909A (en) * | 2022-01-26 | 2022-05-06 | 河南科技大学 | Sulfonyl hinokitiol derivative and its prepn and application |
Also Published As
Publication number | Publication date |
---|---|
FR2496642A1 (en) | 1982-06-25 |
GB2089785B (en) | 1985-07-17 |
DE3049123A1 (en) | 1982-07-15 |
FR2496642B1 (en) | 1985-11-08 |
JPS5626842A (en) | 1981-03-16 |
DE3049123C2 (en) | 1988-01-21 |
CA1162564A (en) | 1984-02-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR920003328B1 (en) | Whitening cosmetic composition | |
US4369174A (en) | Cosmetic composition containing kojic acid ester | |
US4767750A (en) | Topical compositions intended for skin treatment containing salicylic acid derivatives | |
US4278657A (en) | Creamy or milky skin cosmetic compositions containing natural materials as emulsifying agents | |
JP3660692B2 (en) | Tyrosinase biosynthesis inhibitor and whitening agent comprising the same | |
FR2577805A1 (en) | SKIN TREATMENT COMPOSITION BASED ON HYDROQUINONE GLUCOSIDE | |
EP0084341B1 (en) | Emulsion-type composition for external use | |
EP0977550B1 (en) | Use of at least one irvingia gabonensis extract in a cosmetic and/or pharmaceutical product | |
JPH0899820A (en) | Skin external agent | |
JPS609722B2 (en) | fair skin cosmetics | |
US4361581A (en) | Skin-beautifying cosmetic composition | |
GB2089785A (en) | Isopropyltropolone derivatives and their use in skin bleaching cosmetic compositions | |
US4545982A (en) | Pyranone compounds and skin-lightening cosmetic preparations or local demelanizing agents containing the same | |
JPH0545569B2 (en) | ||
KR100419527B1 (en) | Use of sulfites and metabisulfites for manufacturing cosmetic or pharmaceutical compositions, notably in dermatology, with melanogenesis-inhibiting effect or with depigmenting activity | |
JP2001163755A (en) | Preparation for external use for skin | |
JPS60246305A (en) | Cosmetic | |
CA1156152A (en) | Skin-beautifying cosmetic composition | |
EP0717985B1 (en) | Dermatologic preparation | |
JPS58131911A (en) | Cosmetic for fair-complexioned face containing fatty acid ester of quercetin | |
JP4073099B2 (en) | Depigmenting composition | |
JPS6023307A (en) | Skin beautifying cosmetic | |
JPH07149622A (en) | Beautifying and whitening preparation | |
JPS58128310A (en) | Skin conditioner | |
JPH0665043A (en) | Skin external preparation |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19971222 |