WO2006051597A1 - 光学活性ムスコン組成物、およびそれを含有する香粧品 - Google Patents
光学活性ムスコン組成物、およびそれを含有する香粧品 Download PDFInfo
- Publication number
- WO2006051597A1 WO2006051597A1 PCT/JP2004/016825 JP2004016825W WO2006051597A1 WO 2006051597 A1 WO2006051597 A1 WO 2006051597A1 JP 2004016825 W JP2004016825 W JP 2004016825W WO 2006051597 A1 WO2006051597 A1 WO 2006051597A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- optically active
- composition
- muscone
- fragrance
- active muscone
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
Definitions
- the present invention relates to a novel optically active muscone composition, a fragrance composition containing the composition, a fragrance enhancer for cosmetics, and a cosmetic containing them. More specifically, the present invention relates to a novel optically active muscone composition that provides a musk fragrance excellent in diffusibility and volume feeling or powdery feeling, and a fragrance or fragrance of a cosmetic (hereinafter referred to as fragrance). ), A new musk-like fragrance composition and a perfume for cosmetics, and a musk-like fragrance composition that can obtain a high-performing and superior-perfumed cosmetic product.
- the present invention relates to a cosmetic product containing fragrances for fragrances, enno and nusaichi. Furthermore, the present invention relates to the use of the novel photoactive muscone composition.
- Muscon a representative example of musk-like fragrance, is a main scent component of natural scents and incense, and is naturally contained in the incense in an amount of about 0.5 to 2.0%. Muscon was discovered by Walbaum in 1906, and in 1926 by Ruzicka, its chemical structure was determined to be 3-methylcyclopentadecanone.
- the natural muscone is now (1) (R) -3-methylcyclopentadecanone, and the chemical synthesis method for muscone has been established. Therefore, it is easy to obtain, and the synthesized product is a racemic body that is a mixture of one unit of Muscone and d-body, and the strength of racemic body 1 Isomers and d-isomers, that is, (1) (R) -isomers and (+) (S) -isomers can be obtained, and optically active muscone can be synthesized using asymmetric synthesis methods.
- (R) Muscon has a superior fragrance, for example, (1) (R) Muscon has at least one selected from androstenol and 3-methyl-2-hexenoic acid.
- Patent Document 1 There has been a report on a perfume composition that has a long-lasting scent with excellent palatability.
- the Muscons that have been used in cosmetics in the past are (1)-(R) -muscone, or the racemic body, which is an equal mixture of (R)-and (S) -forms of Muscon. Met.
- Patent Document 1 Japanese Patent Laid-Open No. 7-324196
- Non-patent document 1 “Synthetic fragrances chemistry and product knowledge” 492-497, Motoichi Into, Chemical Industry Daily, published on March 6, 1996.
- Non-Patent Document 2 "Latest Technology of Synthetic Fragrance", 72-90, CMC Co., Ltd., published in 1982,
- An object of the present invention relates to the development of a new fragrance material having a higher palatability and a musk-like fragrance that is superior in fragrance quality, and is retained when added to cosmetics.
- a perfume composition and a cosmetic perfume fragrance that can improve the performance and develop a high-performance, highly musk-like fragrance with excellent spreadability, volume and powdery feeling. is there.
- Another object of the present invention is to provide a cosmetic fragrance composition containing the fragrance composition and the cosmetic fragrance.
- an object of the present invention is to provide cosmetics having an excellent musk-like fragrance with improved retentivity and excellent diffusibility, volume feeling or powdery feeling and high performance.
- Another object is to provide a composition that provides the perfume composition and cosmetic perfume. Means for solving the problem
- Optically active Musconca whose volume is in the range of 90: 10—95: 5 (mass ratio) in the mixing ratio of (R) -body Z (S) -body Highly palatability with excellent diffusivity and volume Optically active Musconca diffusion with a musk performance aroma and a steric methyl group in the range of (R) —Z (S) —Body ratio 75: 25—80: 20 (mass ratio) It has been found that it has a taste of musta performance that is particularly excellent in powdery feeling.
- the invention of claim 1 of the present invention is a mixture of the (R) -form of optically active muscone and the (S) -form of optically active muscone, the mixing ratio of which is 75 by mass.
- the invention of claim 2 is a mixture of (R) -form of optically active muscone and (S) -form of optically active muscone, and the mixing ratio is 75: 25-95: 5 as a mass ratio.
- the optically active muscone composition according to claim 1 which is effective as a fragrance composition within a ratio range, or a mixture of (R) -form of optically active muscone and (S) -form of optically active muscone.
- the optically active muscone composition according to claim 1 which is effective as a cosmetic perfume ensemble when the mixing ratio is 75:25 to 95: 5 as a mass ratio.
- the invention of claim 3 is claimed in claim 1 or 2.
- the ratio of the (R) -form of the optically active muscone to the (S) -form of the optically active muscone is 90: 10-95: 5 as a mass ratio
- the invention of claim 4 In the invention of claim 1 or 2, the ratio of the (R) -form of the optically active muscone to the (S) -form of the optically active muscone is 75: 25-80: 20 as a mass ratio. .
- the invention of claim 5 is a mixture of an (R) -form of an optically active muscone and an (S) -form of an optically active muscone, the mixing ratio of which is 90: 10-95: 5 It is a fragrance composition characterized by comprising an optically active muscone in a ratio range as an active ingredient,
- the invention of claim 6 is a mixture of an (R) -form of an optically active muscone and an (S) -form of an optically active muscone, wherein the mixing ratio is 90: 10-95: 5.
- a fragrance for cosmetics characterized by comprising an optically active muscone in the ratio range as an active ingredient, (R) -form of optically active muscone and (S) -form of optically active muscone
- a fragrance for cosmetics characterized in that the active ingredient is an optically active muscone whose mixing ratio is in the range of 75: 25-80: 20 as a mass ratio. is there.
- the invention of claim 7 is a cosmetic containing the fragrance composition of claim 5
- the invention of claim 8 is an invention of a cosmetic containing the perfume for cosmetics according to claim 6 and sensor.
- the invention of claim 9 is an invention relating to the use of the optically active muscone composition of claim 3 or the optically active muscon composition of claim 4 for imparting a musk-like fragrance to a cosmetic product.
- the present invention relates to the use of the optically active muscone composition according to claim 3 or the optically active muscone composition according to claim 4 as an enhancer for cosmetics. The present invention will be described in detail below.
- the optically active muscone composition referred to in the present invention is also composed of two types of optically active muscone, which are (1) (R) -3-methylcyclopentadecanone (hereinafter referred to as (R) muscone or (R) -isomer). ) And (+)-(S) -3-methylcyclopentadecanone (hereinafter sometimes referred to as (S) Muscon or (S) -form).
- these optically active muscons are adjusted so that the mixing ratio (mass ratio) of (R) -body Z (S) is in the range of 75: 25-95: 5, the fragrance of the composition becomes It has a fragrance superior to that of the Muscon fragrance that has been widely used.
- these optically active musks are adjusted so that the mixing ratio (mass ratio) of (R) -body Z (S) is 90: 10-95: 5 or 75: 25-80: 20.
- the composition obtained in this way has a fragrance far superior to that of the conventionally known Muscon fragrance.
- this fragrance composition is superior to the musculon fragrance, which has been widely used in the past, and is particularly superior in musk-like fragrance. It is an excellent perfume composition that is excellent in sensation and powdery and can give a positive effect as a whole.
- the use and application method of the fragrance composition is not particularly limited, and can be applied to all conventionally used fragrance use methods and can impart excellent fragrance. It is also a feature of the present invention that these optically active muscone mixtures are used as cosmetics perfumes.
- the term “enhansa” for perfume for cosmetics as used herein refers to a perfume that has a function of remarkably enhancing a musk-like fragrance when added to a cosmetic or perfume for cosmetics. Or a fragrance
- the starting material for preparing the (R) -form Z (S) -form mixture of the optically active muscone can be obtained by natural product extraction, or can be used in a chemical synthesis method. You can use what you get.
- (R) Muscon Since most of those obtained by extraction from natural products are (R) Muscon, they can be used as the (R) -form of the starting material. However, since the amount can be obtained only by force, it is preferable to use a material obtained by a chemical synthesis method in order to obtain a large amount of the starting material.
- a (R) -isomer Z (S) -isomer mixture of an optically active muscone is prepared by a known method and then optically resolved, and then the optically active muscone (R) — Body and (S) —You can get body.
- 3-methyl-2-cyclopentadecene 1-one is converted into (R)-or (S) -type lute.
- the (R)-and (S) -forms of optically active muskone can be prepared by asymmetric hydrogenation using a -um mono-active phosphine complex as a catalyst.
- the optically active muscone composition of the present invention can be obtained.
- the perfume composition and the perfume fragrance for cosmetics referred to in the present invention can be obtained. Since the natural product strength is (R) -muscone, (S) -muscone obtained by a chemical synthesis method. It is also effective to add and mix it with its naturally derived (R) -muscone in the desired ratio. Similarly, the (R) -muscon can be added and mixed so that the racemic muscone is in the desired ratio.
- the mixture of (R) -form and (S) -form of the optically active muscone of the present invention is extremely good in aroma performance and odor intensity.
- the (R) -body and (S) -body mixture of the optically active muscone of the present invention is highly musk-like and has a unique strength! It has a fragrance characteristic and has a remarkable fragrance sustaining characteristic. By blending this, it is possible to provide a perfume composition with high palatability. Further, by blending a mixture of the (R) -form and (S) -form of the optically active muscone of the present invention, the desired effect of maintaining fragrance and remaining fragrance can be particularly enhanced.
- the mixture of the (R) -form and the (S) -form of the optically active muscone of the present invention itself has a musk-like fragrance. Moreover, the mixture can also be used as an enhancer.
- the blending amount of the mixture into the fragrance or fragrance composition varies depending on the type of the fragrance or blended fragrance, but generally, for example, 0.0001-10 based on the fragrance or fragrance composition. A blending amount of mass%, particularly 0.001-5 mass%, more preferably 0.01-1 mass% is appropriate.
- the fragrance or fragrance composition to which the mixture of the present invention is added is not particularly limited.
- a perfume composition for cosmetics can be prepared by further adding a commonly used perfume component to the mixture of the (R) -form and the (S) -form of the optically active muscone.
- a commonly used perfume component to the mixture of the (R) -form and the (S) -form of the optically active muscone.
- other fragrances include various synthetic fragrances, natural essential oils, synthetic essential oils, citrus oils, and animal fragrances.
- perfume ingredients as described in the following documents can be used.
- fragrances include ⁇ -vinene, limonene, cis-3-hexanol, phenol ethyl alcohol, styryl acetate, eugenol, rose oxide, linalool, benzaldehyde, and dihydrodiasmonic acid. Methyl and Tesalon (Takasago International Corporation).
- fragrance flavor described in Arctander S. "Perfume and Flavor Chemicals" published By the author, Montclair, NJ (U.S.A.) 1969 can be mentioned.
- a mixture of the (R) -form and the (S) -form of the optically active muscone for example, a natural essential oil such as bergamot oil, galvanum oil, lemon oil, gera-um oil, lavender oil, mandarin oil, etc.
- a natural flavoring oil When added to the inside, a natural flavoring oil has a mild and rich aroma, fresh taste, a new fragrance composition for cosmetics that is highly diffusive, durable and durable. Can be prepared.
- the optically active muscone (R) -form and (S) -form mixture or one or two of other fragrance-retaining agents usually used in a fragrance composition for cosmetics.
- Examples of the above-mentioned Frederance products include perfume, eau de perfume, eau de toilette, eau de cologne, etc .
- examples of the basic cosmetics include facial cleansing cream, vanishing cream, cleansing cream, etc. Cream, cold cream, massage cream, milky lotion, lotion, cosmetic liquid, knock, makeup remover, etc .; Lip balm, scarlet, eyeliner, mascara, eye shadow, eyebrow, eye pack, nail enamel, enamel rim bar, etc .
- the hair cosmetics include pomade, brilantine, set lotion, hair tech, hair solid, hair One oil, hair treatment, hair cream, hair nick, hair liquid, hair, one spray, bandlin, hair nourishing agent, hair dye, etc .
- the sarcophagus examples of the body cleansing agent include body soap, body shampoo, hand soap, face cream, etc .; bath preparation, cosmetic stone bath, bath stone, perfume
- bath additives bath salts, bath tablets, bath liquids, etc.
- foam baths bubble baths, etc.
- bath oils baths, bath capsules, etc.
- milk baths bath jelly, bath cubes, etc.
- the detergents include heavy laundry detergents, light laundry detergents, liquid detergents, laundry sarcophagus, Such as softener, fur-chiacare, etc .; cleanser, house cleaner, toilet cleaner, bathroom cleaner, glass cleaner, etc.
- the aerosols include spray types, powder sprays, etc .;
- the agent include solid type, gel type, liquid type (aqueous, oily), and the like.
- the sundries include various forms such as tissue paper and toilet paper.
- the dosage form of the (R) -form / (S) integral mixture of the optically active optically active muscone is a force capable of taking the shape of the mixture itself.
- Other dosage forms include, for example, alcohols, propylene glycol , Polyhydric alcohols such as glycerin and dipropylene glycol, tri Liquid form dissolved in esters such as ethyl citrate, benzyl benzoate, and jetyl phthalate; natural gums such as gum arabic and tragacanth; emulsion emulsified with emulsifiers such as glycerin fatty acid ester and sucrose fatty acid ester; gum arabic Powders coated with excipients such as natural gums, gelatin, dextrin, etc .; surfactants such as nonionic surfactants, ionic surfactants, cationic surfactants, amphoteric surfactants Soluble or solubilized or dispersed using an agent, etc .;
- the perfume composition may be stabilized and sustained-released by inclusion in an inclusion agent such as cyclodextrin.
- an inclusion agent such as cyclodextrin.
- these are suitable for the final product, for example, liquid, solid, powder, gel, miscellaneous, aerosol, etc., and are appropriately selected and used.
- the optically active muscone composition having a specific ratio in the range of the (R) -form / (S) -form of the optically active muscone has an excellent aroma with high performance and has been known for its conventional strength. It can be said that it has properties superior to the musk fragrance.
- the (R) -form / (S) -form mixture of optically active muscone used in the present invention is effective even in a small amount, and can be scented to cosmetics that require perfume fragrance.
- the musk-specific fragrance that excels in diffusibility, volume and powdery can be spread in the blended fragrance containing it to increase its taste and strength. It can have a positive effect, and can give a fresh, tally-like musky feeling.
- (S) Muscon is chemical and unspread! Poor weak! Musk fragrance is preferred because it is musk fragrance and cannot be added. Also, even if the mixture of (R) Muscon and (S) Muscon, the ratio of 90: 10—95: 5 or 75: 25—80: 20 (mass) ratio) If the mixture is out of the limited range, the aroma performance and odor are inferior in strength and are not sufficiently effective.
- the optically active muscone composition in which the (R) -form / (S) -form of the present invention takes a specific range is far superior to the conventional musk-like fragrance and is an extremely practical invention.
- This concentrated oil was purified by silica gel column chromatography to obtain 2.7 g (11.4 mmol) of an aldol mixture of 3-methyl-cyclopentadecene 1-one, (E) — and (Z) -3-methyl-cyclopentadecene 1-one. It was.
- the aldol mixture was further purified by silica gel chromatography, to obtain 0.7 g (3.0 mmol) of (E) -3-methyl-cyclopentadecene 1-one.
- purification by column chromatography using silica gel coated with silver nitrate gave 0.5 g (2.1 mmol) of (Z) -3-methyl-cyclopentadecene 1-one.
- Table 1 shows the evaluation results.
- R means (R) -muscone
- S means (S) -muscone
- Musk-like fragrances are the most important constituents in blended fragrances, and the effect of the musk-like fragrances has a significant effect on the overall scent, such as the scents in blended fragrances, as well as the contribution of fragrances alone.
- Musk fragrances that excel in diffusibility, volume, or powdery can spread and unite in the blended fragrances containing them to increase palatability and strength, and give positive effects overall.
- musk fragrances that are simply clean or flat cannot give a positive effect to the whole, and cannot improve taste and strength.
- musk-like fragrances are not only clean and flat musk fragrances, but also have diffusibility and volume! It is necessary to demonstrate.
- the (R) -form Z (S) -form of the optically active muscone of the present invention had a particularly high palatability and musk-specific performance aroma in a limited range of ratios of 90: 10—95: 5 and 75: 25—80: 20.
- a shampoo fragrance composition was prepared by a conventional method based on the following formulation.
- Example 3 In the formulation of Example 2, instead of a mixture of (R) -form Z (S) -form (92.5: 7.5) of optically active muscone (R) ) -Body Z (S) -Body (77.5: 22.5) A shampoo fragrance composition was prepared according to the same formulation as Example 2. Made.
- Example 2 In the formulation of Example 2, instead of a mixture of (R) -form Z (S) -form (92.5: 7.5) of optically active muscone, (R) -muscon A shampoo perfume composition was prepared by the same formulation as in Example 2 except that (100%) was used.
- Example 3 Using the shampoo perfume composition prepared in Example 2, Example 3 and Comparative Example 1, the following ingredients were heated and stirred at 80 ° C until uniform, then cooled to 35 ° C to prepare a shampoo. .
- Example 3 Using shampoos containing the fragrance compositions of Example 2, Example 3 and Comparative Example 1, respectively, immerse a homogeneous bundle of human hair (20 g) in 50 ml of warm water at 40 ° C. Washed with shampoo (lg) after blending for a minute. A bundle of human hair was removed and dehydrated, then rinsed with 100 ml of warm water and dehydrated. The sensory evaluation was performed in the same manner as in Example 1 for the fragrance that also produced hair strength after 1 hour of drying.
- the fragrance composition and shampoo based on the formulation of Example 2 containing a mixture of (R) -form Z (S) -form (92. Excellent volume
- the fragrance composition and shampoo based on the formulation of Example 3 containing a mixture of (R) -form / (S) -form (77.5: 22.5) of optically active muscone has excellent nodality and whiteness. It was possible to give a tummy-my feeling of musky with a soft cleanliness leading to the same.
- the fragrance composition and the shampoo based on the formulation of Comparative Example 1 containing (R) -muscone (100%) are given a flat musky feeling with weak diffusivity, volume and powdery feeling. Stayed.
- Example 5 In the formulation of Example 4, (R) -form Z (S) -form (92 5: 7.5 According to the same formulation as in Example 4 except that a mixture of (R) -form Z (S) -form (77.5: 22.5) of optically active muscone was used instead of the mixture of 5) A fragrance composition for body shampoo was prepared.
- a shampoo composition for body shampoo was prepared in the same manner as in Example 4 except that (R) -muscon (100%) was used instead of the mixture of 5).
- Example 5 Using the perfume composition for body shampoo prepared in Example 4, Example 5 and Comparative Example 2
- a body shampoo was prepared.
- Example 5 Using the body shampoo containing the fragrance composition of Example 4, Example 5 and Comparative Example 2, the palm was washed with 50 ml of warm water at 40 ° C. and then washed with the body shampoo (lg). It was then rinsed with 100 ml warm water and wiped with a dry towel. At that time, the sensory evaluation was performed in the same manner as in Example 1 for the aroma that also generated palm force.
- the fragrance composition and body shampoo based on the formulation of Example 4 containing a mixture of (R) -form Z (S) -form (92. Volume It was able to give a fresh musky feeling even in the natural and rich nature found in natural scents and incense.
- the perfume composition and body shampoo based on the formulation of Example 5 containing a mixture of (R) -form Z (S) -form (77.5: 22.5) of optically active muscone has excellent powdery feeling. It was possible to give a tummy-like musky feeling with a soft cleanliness leading to whiteness.
- the fragrance composition and body shampoo based on the formulation of Comparative Example 2 containing (R) -muscone (100%) are only given a flat musky feeling with weak diffuseness, volume and powdery feeling. It was.
- a fragrance composition for perfume was prepared by a conventional method based on the following formulation.
- a cosmetic cream was prepared using the perfume composition for perfume prepared in Example 6, Example 7 and Comparative Example 3.
- the cosmetic cream of Comparative Example 3 was applied to the back of the left hand, and the same amount of the cosmetic cream of Example 6 or Example 7 was applied to the back of the right hand. Immediately after application, the fragrance remaining in the hand after 3 hours was subjected to sensory evaluation in the same manner as in Example 1.
- the fragrance composition and makeup cream based on the formulation of Example 6 are excellent in diffusibility and volume, and can give a fresh musky feeling even in the natural richness found in natural scents and incense. It was.
- a perfume composition and a cosmetic cream based on the formulation of Example 7 containing a mixture of (R) -form Z (S) -form (77.5: 22.5) of optically active muscone have excellent powdery feeling. As a result, it was possible to give a tummy-like musky feeling with a soft cleanliness leading to whiteness.
- the fragrance composition and cosmetic cream based on the formulation of Comparative Example 3 containing (R) -muscone (100%) are given a flat musky feeling that weakens diffusivity, volume and powdery feeling. Stayed.
- a perfume composition for detergent was prepared by information.
- Example 9 In the formulation of Example 8, instead of the mixture of (R) -form Z (S) -form (92.5: 7.5) of optically active muscone, A detergent fragrance composition was prepared according to the same formulation as in Example 8, except that a mixture of R) -form Z (S) -form (77.5: 22.5) was used.
- a powder detergent was prepared using the perfume composition for detergent prepared in Example 8, Example 9 and Comparative Example 4.
- Example 9 Using the powder detergent containing the fragrance composition of Example 8, Example 9 and Comparative Example 4, the towel was washed and dehydrated. At that time, the sensory evaluation was performed in the same manner as in Example 1 for the aroma emitted from Towelka.
- the fragrance composition and powder detergent based on the formulation of Example 8 containing a mixture of optically active muscone (R) -form Z (S) -form (92.5: 7.5) had diffusibility and volume. It was excellent in feeling and was able to give a refreshing musky feeling even in the natural richness found in natural and incense.
- Optically active Muscon (R) —body Z (S) body (77.
- Example 9 contains the mixture of 5
- the perfume composition and powder detergent based on the formulation of Example 9 containing the mixture of 5 can give a tally-like musky feeling that is excellent in powdery and has a soft cleanliness that leads to whiteness. It was.
- the fragrance composition and powder detergent based on the formulation of Comparative Example 4 containing (R) -body (100%) are only given a flat musky feeling that weakens diffusivity, volume and powdery feeling. It was.
- a perfume composition for detergent was prepared by information.
- Example 11 In the formulation of Example 10, instead of the mixture of (R) -form Z (S) -form (92.5: 7.5) of optically active muscone (92.5: 7.5) A fragrance composition for a softener was prepared according to the same formulation as in Example 10 except that a mixture of R) -body Z (S) -body (77.5: 22.5) was used.
- Example 5 In the formulation of Example 10, instead of a mixture of (R) -form Z (S) -form (92.5: 7.5) of optically active muscone, optically active muscone A perfume composition for softening was prepared according to the same formulation as in Example 10 except that (R) -muscon (100%) was used.
- Example 10 Using the fragrance composition for softeners prepared in Example 10, Example 11 and Comparative Example 5, A powder detergent was prepared.
- Example 10 and Example 11 are fragrance compositions of Comparative Example 5.
- Example 11 Using the softener for clothing containing the fragrance composition of Example 10, Example 11 and Comparative Example 5, it was dipped in a towel washed with an unscented detergent for 10 minutes and dehydrated. At that time, the sensory evaluation was performed in the same manner as in Example 1 for the aroma emitted from the towel.
- the fragrance composition and powder detergent based on the formulation of Example 10 containing a mixture of optically active muscone (R) -form Z (S) -form (92.5: 7.5) contained diffusivity and volume. It was excellent in feeling, and it was able to give a fresh musky feeling even in the natural and rich nature found in natural and incense.
- the fragrance composition and powder detergent based on the formulation of Example 11 containing a mixture of optically active muscone (R) -form Z (S) -form (77.5: 25.5) has an excellent powdery feeling, white powder It was possible to give a tummy-like musky feeling with a soft feeling of cleanliness leading to the same.
- the fragrance composition and the powder detergent based on the formulation of Comparative Example 5 containing (R) -body (100%) are only given a flat musky feeling that weakens the diffusive volume and powdery feeling. It was.
- Optically active muscone (R) -form and optically active muscone (S) -form mixture the mixing ratio of which is in the range of 90: 10-95: 5
- a perfume composition comprising active muscone as an active ingredient.
- a fragrance composition comprising the additive according to (5) or (6) added at a concentration of 0.001 to 20% by mass.
- the ratio of the (R) -form of the optically active muscone to the (S) -form of the optically active muscone is 90: 10-95: 5 to give a musk-like fragrance to the cosmetic product.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/JP2004/016825 WO2006051597A1 (ja) | 2004-11-12 | 2004-11-12 | 光学活性ムスコン組成物、およびそれを含有する香粧品 |
JP2006544702A JP4808633B2 (ja) | 2004-11-12 | 2004-11-12 | 光学活性ムスコン組成物、およびそれを含有する香粧品 |
EP04822394A EP1820842B1 (en) | 2004-11-12 | 2004-11-12 | Optically active muscone composition and perfume product containing the same |
US11/719,109 US8093203B2 (en) | 2004-11-12 | 2004-11-12 | Method of enhancing fragrance by adding optically active muscone composition |
CA2587666A CA2587666C (en) | 2004-11-12 | 2004-11-12 | Optically active muscone composition and fragrances or cosmetics containing the same |
US12/853,581 US20100305216A1 (en) | 2004-11-12 | 2010-08-10 | Optically active muscone composition and fragrances or cosmetics containing the same |
US13/219,005 US8227401B2 (en) | 2004-11-12 | 2011-08-26 | Optically active muscone composition and fragrances or cosmetics containing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/JP2004/016825 WO2006051597A1 (ja) | 2004-11-12 | 2004-11-12 | 光学活性ムスコン組成物、およびそれを含有する香粧品 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/719,109 A-371-Of-International US8093203B2 (en) | 2004-11-12 | 2004-11-12 | Method of enhancing fragrance by adding optically active muscone composition |
US12/853,581 Division US20100305216A1 (en) | 2004-11-12 | 2010-08-10 | Optically active muscone composition and fragrances or cosmetics containing the same |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006051597A1 true WO2006051597A1 (ja) | 2006-05-18 |
Family
ID=36336283
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2004/016825 WO2006051597A1 (ja) | 2004-11-12 | 2004-11-12 | 光学活性ムスコン組成物、およびそれを含有する香粧品 |
Country Status (5)
Country | Link |
---|---|
US (3) | US8093203B2 (ja) |
EP (1) | EP1820842B1 (ja) |
JP (1) | JP4808633B2 (ja) |
CA (1) | CA2587666C (ja) |
WO (1) | WO2006051597A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100247475A1 (en) * | 2007-09-20 | 2010-09-30 | Kao Corporation | Beta-glucuronidase inhibitor |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090312224A1 (en) * | 2008-06-13 | 2009-12-17 | Conopco, Inc., D/B/A Unilever | Method of Reducing Viscosity of Concentrated Liquid Cleansers by Selection of Perfume Components |
US20090312223A1 (en) * | 2008-06-13 | 2009-12-17 | Conopco, Inc., D/B/A Unilever | Method of Controlling Structure and Rheology of Low Active Liquid Cleansers by Selecting Perfume Components |
US20120245075A1 (en) * | 2011-03-24 | 2012-09-27 | Timothy Jay Young | High Performance Fragrance Formulation |
US9896644B2 (en) | 2014-01-14 | 2018-02-20 | Firmenich Sa | Powdery, musky odorant macrocycles |
US20160304806A1 (en) * | 2015-02-02 | 2016-10-20 | Johnson & Johnson Consumer Inc. | Perfume compositions |
MX2017009943A (es) * | 2015-02-02 | 2017-12-07 | Johnson & Johnson Consumer Inc | Composiciones de perfume. |
CN108076626A (zh) * | 2015-06-29 | 2018-05-25 | 高砂香料工业株式会社 | 麝香组合物和其使用方法 |
WO2017131818A1 (en) * | 2016-01-28 | 2017-08-03 | Johnson & Johnson Consumer Inc. | Perfume compositions |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07324196A (ja) | 1994-05-30 | 1995-12-12 | Kanebo Ltd | 香料組成物 |
CN1307296C (zh) * | 2000-06-20 | 2007-03-28 | 株式会社资生堂 | 缓和紧张香料及含该香料的缓和紧张香料组合物 |
-
2004
- 2004-11-12 CA CA2587666A patent/CA2587666C/en not_active Expired - Fee Related
- 2004-11-12 US US11/719,109 patent/US8093203B2/en not_active Expired - Fee Related
- 2004-11-12 EP EP04822394A patent/EP1820842B1/en active Active
- 2004-11-12 JP JP2006544702A patent/JP4808633B2/ja active Active
- 2004-11-12 WO PCT/JP2004/016825 patent/WO2006051597A1/ja active Application Filing
-
2010
- 2010-08-10 US US12/853,581 patent/US20100305216A1/en not_active Abandoned
-
2011
- 2011-08-26 US US13/219,005 patent/US8227401B2/en not_active Expired - Fee Related
Non-Patent Citations (11)
Title |
---|
ALEXAKIS A ET AL., SYNLETT, vol. 11, 1999, pages 1811 - 1813 |
IULIANO A ET AL: "Deoxycholic acid-based phosphates as chiral ligands in the enantioselective conjugate addition of dialkylzincs to cyclic enones: preparation of (-)-(R)-muscone.", TETRAHEDRON: ASYMMETRY., vol. 15, no. 16, 23 August 2004 (2004-08-23), pages 2533 - 2538, XP004533948 * |
KAZUHIKO TANAKA ET AL., J. CHEM. SOC., vol. 11, 1990, pages 795 - 797 |
LULIANO A ET AL.: "Tetrahedron Asymmetry", vol. 15, 2004, PERGAMON PRESS LTD., pages: 2533 - 2538 |
SCAFATO P ET AL.: "Tetrahedron", vol. 60, 2004, ELSEVIER SCIENCE PUBLISHERS, pages: 8801 - 8806 |
SCAFATO P ET AL: "Asymmetric activation of tropos catalysts in the stereoselective catalytic conjugate additions of R2Zn to alpha, beta-enones: an efficient synthesis of (-)-muscone.", TETRAHEDRON., vol. 60, no. 40, 27 September 2004 (2004-09-27), pages 8801 - 8806, XP004565029 * |
SCAFATO P ET AL: "Catalytic enantioselective conjugate addition of dialkyl zinc reagents to alpha, beta-unsaturated ketones mediated by new phosphite ligands containing binaphthalene/1,2-diphenylethane moieties: a practical synthesis of (R)-(-)-muscone.", TETRAHEDRON: ASYMMETRY., vol. 14, no. 24, 2003, pages 3873 - 3877, XP004476259 * |
See also references of EP1820842A4 |
TOMOYUKI OGAWA ET AL., J. CHEM. SOC., vol. 20, 1991, pages 1438 - 1439 |
YAMAMOTO T ET AL: "A novel synthetic method for (R)- and (S)-muscones by enantioselective hydrogenation of (E)- and (Z)-3-methyl-2-cyclopentadecen-1-ones catalyzed by p-tolyl-BINAP-Ru(II) complexes.", TETRAHEDRON., vol. 58, no. 45, 2002, pages 9209 - 9212, XP004390244 * |
YAMAMOTO T. ET AL.: "Tetrahedron", vol. 58, 2002, ELSEVIER SCIENCE PUBLISHERS, pages: 9209 - 9212 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100247475A1 (en) * | 2007-09-20 | 2010-09-30 | Kao Corporation | Beta-glucuronidase inhibitor |
US9200269B2 (en) * | 2007-09-20 | 2015-12-01 | Kao Corporation | β-glucuronidase inhibitor |
Also Published As
Publication number | Publication date |
---|---|
CA2587666A1 (en) | 2006-05-18 |
US8227401B2 (en) | 2012-07-24 |
US8093203B2 (en) | 2012-01-10 |
CA2587666C (en) | 2012-09-25 |
JPWO2006051597A1 (ja) | 2008-05-29 |
US20090143485A1 (en) | 2009-06-04 |
EP1820842A4 (en) | 2009-12-02 |
US20110313201A1 (en) | 2011-12-22 |
EP1820842B1 (en) | 2012-07-04 |
JP4808633B2 (ja) | 2011-11-02 |
EP1820842A1 (en) | 2007-08-22 |
US20100305216A1 (en) | 2010-12-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8227401B2 (en) | Optically active muscone composition and fragrances or cosmetics containing the same | |
JP7018025B2 (ja) | フレグランス物質 | |
JP5160002B2 (ja) | 香粧品用香料組成物及び香気を付与した香粧品 | |
JP2003238985A (ja) | 香料組成物 | |
JP5065608B2 (ja) | ミント組成物 | |
JP6498184B2 (ja) | 新規化合物及び該化合物を含有する香料組成物 | |
US9464257B2 (en) | Fragrance composition | |
JP6484877B2 (ja) | 香料組成物 | |
JP3649441B1 (ja) | 3級メルカプトケトンおよびそれを含有する香気・香味組成物 | |
JP5025955B2 (ja) | 香料組成物 | |
CN104066416A (zh) | 新颖的感官化合物 | |
CA2753315C (en) | Optically active muscone composition and fragrances or cosmetics containing the same | |
JP2004210958A (ja) | 香料組成物及び芳香製品の芳香性を改良又は増強する方法 | |
JP2010083831A (ja) | 低感作性香気化合物およびそれを含有する香料組成物 | |
WO2024096037A1 (ja) | 香料組成物および消費者製品 | |
JP2000034243A (ja) | 光学活性な1−(p−メンタ−3’−イル)エタノール及びそれを有効成分とする香料 | |
JP2013241570A (ja) | 組成物、及び、それを含有する製品、並びにその組成物で香料組成物の香気特性を改善する方法 | |
JP2006117585A (ja) | 新規香料物質及びその利用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2006544702 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004822394 Country of ref document: EP Ref document number: 2587666 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 11719109 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 2004822394 Country of ref document: EP |