US20180320105A1 - 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient - Google Patents
1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient Download PDFInfo
- Publication number
- US20180320105A1 US20180320105A1 US16/034,296 US201816034296A US2018320105A1 US 20180320105 A1 US20180320105 A1 US 20180320105A1 US 201816034296 A US201816034296 A US 201816034296A US 2018320105 A1 US2018320105 A1 US 2018320105A1
- Authority
- US
- United States
- Prior art keywords
- perfuming
- compound
- perfumery
- formula
- product
- 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.)
- Abandoned
Links
- JMLYELPJNSRZHS-UHFFFAOYSA-N CC(C)OC(=O)C(C)OC(=O)C(C)(C)C Chemical compound CC(C)OC(=O)C(C)OC(=O)C(C)(C)C JMLYELPJNSRZHS-UHFFFAOYSA-N 0.000 description 4
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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
-
- 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
- C07C69/67—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 saturated acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2093—Esters; Carbonates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
-
- 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
- A61K2800/10—General cosmetic use
-
- 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
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q9/00—Preparations for removing hair or for aiding hair removal
- A61Q9/02—Shaving preparations
Definitions
- the present invention relates to the field of perfumery. More particularly, it concerns the use of 1-isopropoxy-1-oxopropan-2-yl pivalate, in the form of any one of its stereoisomers or a mixture thereof, as perfuming ingredient.
- the present invention comprises the invention's compound as part of a perfuming composition or of a perfuming consumer product.
- perfuming ingredient for instance to impart odor notes of the floral and fruity type.
- any one of its stereoisomers or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that the invention's compound can be a pure enantiomer (e.g. the one of configuration S or R).
- (+)-(R)-1-isopropoxy-1-oxopropan-2-yl pivalate which possesses an odor similar to the one of the S enantiomer but distinguishing itself by a slightly more pronounced fruity note and being less raising than the S enantiomer.
- the compounds of formula (I) are ( ⁇ )-(S)-1-isopropoxy-1-oxopropan-2-yl pivalate or 1-isopropoxy-1-oxopropan-2-yl pivalate.
- the odor of the invention's compounds is compared with that of the prior art compounds described in WO2009/147565, such as propyl (S)-2-(isobutyryloxy)propanoate, ( ⁇ )-(S)-1-isopropoxy-1-oxopropan-2-yl isobutyrate or ( ⁇ )-(S)-1-ethoxy-1-oxopropan-2-yl pivalate, then the invention's compounds distinguish themselves by having a floral (rosy/geranium) note which is absent, or not significant, in the prior art compounds. Said floral note is a distinguishing character of the odor profile of the invention's compound and not a simple aspect or shade, as shown in the examples.
- the present invention's compounds do distinguish also by having a different type of fruity notes (in the present case of the citrusy type) when compared to the prior art compounds. Said differences lend the invention's compounds and the prior art compounds to be each suitable for different uses, i.e. to impart different organoleptic impressions.
- the invention concerns the use of a compound of formula (I) as perfuming ingredient.
- it concerns a method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I).
- use of a compound of formula (I) it has to be understood here also the use of any composition containing a compound (I) and which can be advantageously employed in the perfumery industry.
- compositions which in fact can be advantageously employed as perfuming ingredients, are also an object of the present invention.
- Another object of the present invention is a perfuming composition
- a perfuming composition comprising:
- perfumery carrier we mean here a material which is practically neutral from a perfumery point of view, i.e., that does not significantly alter the organoleptic properties of perfuming ingredients.
- Said carrier may be a liquid or a solid.
- liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery.
- a solvent and a surfactant system i.e. a solvent and a surfactant system
- a solvent commonly used in perfumery A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive.
- solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, which are the most commonly used.
- compositions which comprise both a perfumery carrier and a perfumery base can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company).
- Isopar® oil/ethanol mixtures
- glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company).
- absorbing gums or polymers may comprise wall-forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- and Gelierstoff in Strukturn, Band 2 der Strukturtechnisch Herbert Strukturchemie, claritat, Behr's Verlag GmbH & Co., Hamburg, 1996.
- the encapsulation is a well known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation technique.
- perfumery base we mean here a composition comprising at least one perfuming co-ingredient.
- perfuming co-ingredient is not of formula (I).
- perfuming co-ingredient it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect.
- co-ingredient to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
- perfuming co-ingredients present in the base do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to intended use or application and the desired organoleptic effect.
- these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S.
- perfumery adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming bases cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art.
- An invention's composition consisting of at least one compound of formula (I) and at least one perfumery carrier represents a particular embodiment of the invention as well as a perfuming composition comprising at least one compound of formula (I), at least one perfumery carrier, at least one perfumery base, and optionally at least one perfumery adjuvant.
- any mixture resulting directly from a chemical synthesis e.g. a reaction medium without an adequate purification, in which the compound of the invention would be involved as a starting, intermediate or end-product could not be considered as a perfuming composition according to the invention as far as said mixture does not provide the inventive compound in a suitable form for perfumery.
- unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.
- the invention's compound can also be advantageously used in all the fields of modern perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of a consumer product into which said compound (I) is added. Consequently, another object of the present invention is represented by a perfuming consumer product comprising, as a perfuming ingredient, at least one compound of formula (I), as defined above.
- the invention's compound can be added as such or as part of an invention's perfuming composition.
- perfuming consumer product it is meant a consumer product which is expected to deliver at least a perfuming effect, in other words it is a perfumed consumer product.
- perfumery consumer base we mean here the functional formulation, as well as optionally additional benefit agents, corresponding to a consumer product which is compatible with perfuming ingredients and is expected to deliver a pleasant odor to the surface to which it is applied (e.g. skin, hair, textile, or home surface).
- a perfuming consumer product according to the invention comprises the functional formulation, as well as optionally additional benefit agents, corresponding to the desired consumer product, e.g. a detergent or an air freshener, and an olfactive effective amount of at least one invention's compound.
- Non-limiting examples of suitable perfuming consumer product can be a perfume, such as a fine perfume, a cologne or an after-shave lotion; a fabric care product, such as a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, or a bleach; a body-care product, such as a hair care product (e.g. a shampoo, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream or a deodorant or antiperspirant), or a skin-care product (e.g.
- a hair care product e.g. a shampoo, a coloring preparation or a hair spray
- a cosmetic preparation e.g. a vanishing cream or a deodorant or antiperspirant
- a skin-care product e.g.
- a perfumed soap, shower or bath mousse, oil or gel, or a hygiene product a perfumed soap, shower or bath mousse, oil or gel, or a hygiene product
- an air care product such as an air freshener or a “ready to use” powdered air freshener
- a home care product such as a wipe, a dish detergent or hard-surface detergent.
- Some of the above-mentioned perfuming consumer products may represent an aggressive medium for the invention's compound, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation or by chemically bounding it to another chemical which is suitable to release the invention's ingredient upon a suitable external stimulus, such as an enzyme, light, heat or a change of pH.
- a suitable external stimulus such as an enzyme, light, heat or a change of pH.
- the proportions in which the compounds according to the invention can be incorporated into the various aforementioned products or compositions vary within a wide range of values. These values are dependent on the nature of the product to be perfumed and on the desired organoleptic effect as well as the nature of the co-ingredients in a given base when the compounds according to the invention are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.
- concentrations are in the order of 1% to 50% by weight, or even more, of the compounds of the invention based on the weight of the composition into which they are incorporated. Concentrations lower than these, such as in the order of 0.05% to 20% by weight, can be used when these compounds are incorporated into perfuming consumer product, percentage being relative to the weight of the article.
- the invention's compounds can be prepared according to a method as described in the examples herein below.
- the R enantiomer or the racemate can be obtained exactly by the same method except that the starting material used is R-(+)-isopropyl lactate or isopropyl lactate respectively.
- a perfuming composition for a “all purpose cleaner” was prepared by admixing the following ingredients:
- a perfuming composition for a “eau de cologne” type was prepared by admixing the following ingredients:
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Seasonings (AREA)
Abstract
Description
- This application is a division of U.S. application Ser. No. 14/904,328 filed Jan. 11, 2016, which is a 371 filing of International application no. PCT/EP2014/064138 filed Jul. 3, 2014, which claims the benefit of European application no. 13175628.0 filed Jul. 8, 2013, the entire contents of each application incorporated herein by reference thereto.
- The present invention relates to the field of perfumery. More particularly, it concerns the use of 1-isopropoxy-1-oxopropan-2-yl pivalate, in the form of any one of its stereoisomers or a mixture thereof, as perfuming ingredient. The present invention comprises the invention's compound as part of a perfuming composition or of a perfuming consumer product.
- To the best of our knowledge, the invention's compound as such is novel.
- WO2009/147565, although not disclosing specifically the invention's compound, reports perfuming compounds of a general formula encompassing the invention's compound; however said prior art compounds are described as being of the fruity type, while the present compound does have an additional and surprising floral note.
- We have now surprisingly discovered that 1-isopropoxy-1-oxopropan-2-yl pivalate, of formula
- in the form of any one of its stereoisomers or a mixture thereof;
- can be used as perfuming ingredient, for instance to impart odor notes of the floral and fruity type.
- For the sake of clarity, by the expression “any one of its stereoisomers”, or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that the invention's compound can be a pure enantiomer (e.g. the one of configuration S or R).
- As specific examples of the invention's compounds, one may cite, as non-limiting example, (−)-(S)-1-isopropoxy-1-oxopropan-2-yl pivalate which possesses an odor having a floral, rosy/geranium type note having also a linalool, citronellol, geranyl acetate aspect, as well as a fruity, citrusy type note having lemon, bergamot aspects. The overall hedonic effect is an interesting rosy/geranium and fruity impression.
- As other example, one may cite (+)-(R)-1-isopropoxy-1-oxopropan-2-yl pivalate, which possesses an odor similar to the one of the S enantiomer but distinguishing itself by a slightly more pronounced fruity note and being less raising than the S enantiomer.
- As other example, one may cite 1-isopropoxy-1-oxopropan-2-yl pivalate, which possesses an odor similar to the one of the S enantiomer but distinguishes itself surprisingly by a slightly more pronounced floral/rosy note.
- According to a particular embodiment of the invention, the compounds of formula (I) are (−)-(S)-1-isopropoxy-1-oxopropan-2-yl pivalate or 1-isopropoxy-1-oxopropan-2-yl pivalate.
- When the odor of the invention's compounds is compared with that of the prior art compounds described in WO2009/147565, such as propyl (S)-2-(isobutyryloxy)propanoate, (−)-(S)-1-isopropoxy-1-oxopropan-2-yl isobutyrate or (−)-(S)-1-ethoxy-1-oxopropan-2-yl pivalate, then the invention's compounds distinguish themselves by having a floral (rosy/geranium) note which is absent, or not significant, in the prior art compounds. Said floral note is a distinguishing character of the odor profile of the invention's compound and not a simple aspect or shade, as shown in the examples.
- The present invention's compounds do distinguish also by having a different type of fruity notes (in the present case of the citrusy type) when compared to the prior art compounds. Said differences lend the invention's compounds and the prior art compounds to be each suitable for different uses, i.e. to impart different organoleptic impressions.
- As mentioned above, the invention concerns the use of a compound of formula (I) as perfuming ingredient. In other words, it concerns a method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I). By “use of a compound of formula (I)” it has to be understood here also the use of any composition containing a compound (I) and which can be advantageously employed in the perfumery industry.
- Said compositions, which in fact can be advantageously employed as perfuming ingredients, are also an object of the present invention.
- Therefore, another object of the present invention is a perfuming composition comprising:
- i) as perfuming ingredient, at least one invention's compound as defined above;
- ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and
- iii) optionally at least one perfumery adjuvant.
- By “perfumery carrier” we mean here a material which is practically neutral from a perfumery point of view, i.e., that does not significantly alter the organoleptic properties of perfuming ingredients. Said carrier may be a liquid or a solid.
- As liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive. However, one can cite as non-limiting examples solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, which are the most commonly used. For the compositions which comprise both a perfumery carrier and a perfumery base, other suitable perfumery carriers than those previously specified, can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company).
- As solid carriers one may cite, as non-limiting examples, absorbing gums or polymers, or yet encapsulating materials. Examples of such materials may comprise wall-forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- and Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitat, Behr's Verlag GmbH & Co., Hamburg, 1996. The encapsulation is a well known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation technique.
- By “perfumery base” we mean here a composition comprising at least one perfuming co-ingredient.
- Said perfuming co-ingredient is not of formula (I). Moreover, by “perfuming co-ingredient” it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect. In other words such a co-ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
- The nature and type of the perfuming co-ingredients present in the base do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to intended use or application and the desired organoleptic effect. In general terms, these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.
- By “perfumery adjuvant” we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming bases cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art.
- An invention's composition consisting of at least one compound of formula (I) and at least one perfumery carrier represents a particular embodiment of the invention as well as a perfuming composition comprising at least one compound of formula (I), at least one perfumery carrier, at least one perfumery base, and optionally at least one perfumery adjuvant.
- It is useful to mention here that the possibility to have, in the compositions mentioned above, more than one compound of formula (I) is important as it enables the perfumer to prepare accords, perfumes, possessing the odor tonality of various compounds of the invention, creating thus new tools for his work.
- For the sake of clarity, it is also understood that any mixture resulting directly from a chemical synthesis, e.g. a reaction medium without an adequate purification, in which the compound of the invention would be involved as a starting, intermediate or end-product could not be considered as a perfuming composition according to the invention as far as said mixture does not provide the inventive compound in a suitable form for perfumery. Thus, unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.
- Furthermore, the invention's compound can also be advantageously used in all the fields of modern perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of a consumer product into which said compound (I) is added. Consequently, another object of the present invention is represented by a perfuming consumer product comprising, as a perfuming ingredient, at least one compound of formula (I), as defined above.
- The invention's compound can be added as such or as part of an invention's perfuming composition.
- For the sake of clarity, it has to be mentioned that, by “perfuming consumer product” it is meant a consumer product which is expected to deliver at least a perfuming effect, in other words it is a perfumed consumer product. For the sake of clarity, it has to be mentioned that, by “perfumery consumer base” we mean here the functional formulation, as well as optionally additional benefit agents, corresponding to a consumer product which is compatible with perfuming ingredients and is expected to deliver a pleasant odor to the surface to which it is applied (e.g. skin, hair, textile, or home surface). In other words, a perfuming consumer product according to the invention comprises the functional formulation, as well as optionally additional benefit agents, corresponding to the desired consumer product, e.g. a detergent or an air freshener, and an olfactive effective amount of at least one invention's compound.
- The nature and type of the constituents of the perfuming consumer product do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature and the desired effect of said product.
- Non-limiting examples of suitable perfuming consumer product can be a perfume, such as a fine perfume, a cologne or an after-shave lotion; a fabric care product, such as a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, or a bleach; a body-care product, such as a hair care product (e.g. a shampoo, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream or a deodorant or antiperspirant), or a skin-care product (e.g. a perfumed soap, shower or bath mousse, oil or gel, or a hygiene product); an air care product, such as an air freshener or a “ready to use” powdered air freshener; or a home care product, such as a wipe, a dish detergent or hard-surface detergent.
- Some of the above-mentioned perfuming consumer products may represent an aggressive medium for the invention's compound, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation or by chemically bounding it to another chemical which is suitable to release the invention's ingredient upon a suitable external stimulus, such as an enzyme, light, heat or a change of pH.
- The proportions in which the compounds according to the invention can be incorporated into the various aforementioned products or compositions vary within a wide range of values. These values are dependent on the nature of the product to be perfumed and on the desired organoleptic effect as well as the nature of the co-ingredients in a given base when the compounds according to the invention are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.
- For example, in the case of perfuming compositions, typical concentrations are in the order of 1% to 50% by weight, or even more, of the compounds of the invention based on the weight of the composition into which they are incorporated. Concentrations lower than these, such as in the order of 0.05% to 20% by weight, can be used when these compounds are incorporated into perfuming consumer product, percentage being relative to the weight of the article.
- The invention's compounds can be prepared according to a method as described in the examples herein below.
- The invention will now be described in further detail by way of the following examples, wherein the abbreviations have the usual meaning in the art, the temperatures are indicated in degrees centigrade (° C.); the NMR spectral data were recorded in CDCl3 (if not stated otherwise) with a 360 or 400 MHz machine for 1H and 13C, the chemical shifts δ are indicated in ppm with respect to TMS as standard, the coupling constants J are expressed in Hz.
- To a solution of S-(−)-isopropyl lactate (68.1 g, 0.5 mole, [α]20 D=−3.2°, 2.5%, CHCl3), triethylamine (61.3 g, 0.6 mole) in dichloromethane (800 ml) at 0° was slowly added pivaloyl chloride (67.0 g, 0.55 mole). After 24 hours at room temperature, the mixture was quenched with 10% HCl (200 ml) and crushed ice (100 g) and then the organic phase was washed with aqueous NaHCO3, water and dried over Na2SO4. Evaporation of dichloromethane provided a residue (96.7 g) which was rapidly distilled using a Vigreux column (B.p.12 mbars=80-85°) and then fractionated using a Fischer column (B.p.12 mbars=83-85°) to give 51.1 g (yield=47%) of pure (−)-(S)-1-isopropoxy-1-oxopropan-2-yl pivalate.
- [α]20D=−32.6° (3.1%, CHCl3).
- 1H-NMR: 1.23 (d: J=6, 3H); 1.24 (s, 9H); 1.26 (d: J=6, 3H); 1.47 (d: J=7, 3H); 4.99 (q: J=7, 1H); 5.05 (sept., J=6, 1H).
- 13C-NMR: 16.7 (q), 21.6 (q), 21.7 (q), 27.0 (3q), 38.5 (s), 68.6 (d), 68.8 (d), 170.5 (s), 177.8 (s).
- The R enantiomer or the racemate can be obtained exactly by the same method except that the starting material used is R-(+)-isopropyl lactate or isopropyl lactate respectively.
- A perfuming composition for a “all purpose cleaner” was prepared by admixing the following ingredients:
-
Parts by weight Ingredient 900 Isobornyl acetate 300 Benzyl acetate 200 Anisic aldehyde 50 Aldehyde mna 50 Methyl anthranilate 50 10%* 4-(4-Hydroxy-1-phenyl)-2-butanone 20 Borneol 30 Citronellyl nitrile 300 Coranol ™ 1) 100 Coumarine 200 (1′R,E)-2-Ethyl-4-(2′,2′,3′-trimethyl- 3′-cyclopenten-1′-yl)-2-buten-1-ol 100 Eugenol 100 1,3-Benzodioxole-5-carbaldehyde 350 Lavandin grosso 50 Menthone 20 Crystal moss 50 Rose oxide 150 Patchouli oil 150 Phenethylol 400 Orange essential oil 500 Amyl salicylate 700 Benzyl salicylate 450 Terpineol 250 Terpinolene 30 Yara yara 400 Lemon essential oil 100 Ylang oil 6000 *in dipropyleneglycol 1) 4-cyclohexyl-2-methyl-2-butanol; origin: Firmenich SA, Geneva, Switzerland - The effect obtained by the addition to the above composition of 4000 parts by weight of the following compounds was described as:
- a) (−)-(S)-1-isopropoxy-1-oxopropan-2-yl pivalate introduced a fruitiness and a floral-geranium aspect to the fragrance. The geranium aspect, obtained when adding the invention's compound was comparable to the addition of a 80/20 mixture of propyl (S)-2-(1,1-dimethylpropoxy)propanoate (see EP 1069176) and citronellol (3200 parts 800 parts resp.);
- b) propyl (S)-2-(isobutyryloxy)propanoate (WO2009/147565) imparted no floral notes but a similar fruitiness as propyl (S)-2-(1,1-dimethylpropoxy)propanoate (see EP 1069176) but less freshness overall;
- c) (−)-(S)-1-ethoxy-1-oxopropan-2-yl pivalate (WO2009/147565) imparted no floral notes but a butyric fruitiness, reminiscent of apple and strawberry;
- d) ethyl (S)-2-(propanoyloxy)propanoate (WO2009/147565) imparted no floral notes but a fruity/green, metallic, vinous/rhubarb note; or
- e) (−)-(S)-1-isopropoxy-1-oxopropan-2-yl isobutyrate (WO2009/147565) imparted no floral notes but only a butyric fruitiness reminiscent of apricot.
- A perfuming composition for a “eau de cologne” type, was prepared by admixing the following ingredients:
-
Parts by weight Ingredient 250 Wormwood oil 1500 Bergamot oil 2200 Lemon oil 300 Lavender oil 150 Mandarin oil 100 Crystal moss 100 Muscenone ™ Delta1) 700 Petitgrain 2000 Orange oil 300 Rosemary oil 100 Clary sage oil 300 Neroli oil 8000 1)3-methyl-5-cyclopentadecen-1-one; origin: Firmenich SA, Geneva, Switzerland - The effect obtained by the addition to the above composition of 2000 parts by weight of the following compounds was described as:
- a) (−)-(S)-1-isopropoxy-1-oxopropan-2-yl pivalate imparted a rounder citrus notes and fruitier and added a floral geranium/rose note. The same floral effect introduced by the invention's compound was obtained by adding a mixture of roughly 75% propyl (S)-2-(1,1-dimethylpropoxy)propanoate (see EP 1069176) and 25% Citronellol (1500 parts and 500 parts respectively), but not by adding 2000 parts of propyl (S)-2-(1,1-dimethylpropoxy)propanoate (see EP 1069176) alone;
- b) propyl (S)-2-(isobutyryloxy)propanoate (WO2009/147565) imparted no floral notes but pushed the aromatic notes, and added less fruitiness to the citrus notes than the invention compound;
- c) Ethyl (S)-2-(propanoyloxy)propanoate (WO2009/147565) imparted no floral notes but makes the composition bitter green and harsh; or
- d) (−)-(S)-1-ethoxy-1-oxopropan-2-yl pivalate (WO2009/147565) imparted no floral notes but added a sweet, butyrique fruitiness which, combined with the crystal moss, creates a typical fruity Chypre effect.
Claims (13)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US16/034,296 US20180320105A1 (en) | 2013-07-08 | 2018-07-12 | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13175628 | 2013-07-08 | ||
EP13175628.0 | 2013-07-08 | ||
PCT/EP2014/064138 WO2015003985A1 (en) | 2013-07-08 | 2014-07-03 | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient |
US201614904328A | 2016-01-11 | 2016-01-11 | |
US16/034,296 US20180320105A1 (en) | 2013-07-08 | 2018-07-12 | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2014/064138 Division WO2015003985A1 (en) | 2013-07-08 | 2014-07-03 | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient |
US14/904,328 Division US10047319B2 (en) | 2013-07-08 | 2014-07-03 | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient |
Publications (1)
Publication Number | Publication Date |
---|---|
US20180320105A1 true US20180320105A1 (en) | 2018-11-08 |
Family
ID=48745854
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US14/904,328 Active US10047319B2 (en) | 2013-07-08 | 2014-07-03 | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient |
US16/034,296 Abandoned US20180320105A1 (en) | 2013-07-08 | 2018-07-12 | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US14/904,328 Active US10047319B2 (en) | 2013-07-08 | 2014-07-03 | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient |
Country Status (9)
Country | Link |
---|---|
US (2) | US10047319B2 (en) |
EP (1) | EP3019584B1 (en) |
JP (1) | JP6377154B2 (en) |
CN (2) | CN113025426A (en) |
BR (1) | BR112015027807A2 (en) |
ES (1) | ES2638495T3 (en) |
IL (1) | IL243284B (en) |
MX (1) | MX2015015559A (en) |
WO (1) | WO2015003985A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10766850B2 (en) * | 2008-06-04 | 2020-09-08 | Firmenich Sa | Fruity odorant |
US11401483B2 (en) | 2018-06-26 | 2022-08-02 | Mitsubishi Gas Chemical Company, Inc. | Isobutyric ester compound having butyryloxy group or pivaloyloxy group at α-position and fragrance composition |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3816268A4 (en) * | 2018-06-26 | 2021-08-04 | Mitsubishi Gas Chemical Company, Inc. | Isobutyric ester compound having propanoyloxy group at ? position, perfume composition, and use as perfume |
US20220153681A1 (en) * | 2019-02-27 | 2022-05-19 | Mitsubishi Gas Chemical Company, Inc. | ISOBUTYRIC ACID ESTER COMPOUND HAVING N-BUTYRYLOXY AT a-POSITION, PERFUME COMPOSITION, AND USE AS PERFUME |
CN112778131B (en) * | 2021-01-04 | 2022-07-08 | 东莞波顿香料有限公司 | Compound with litchi aroma, preparation method thereof and daily essence |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110097291A1 (en) * | 2008-06-04 | 2011-04-28 | Firmenich Sa | Fruity odorant |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1069176B1 (en) | 1999-07-14 | 2004-09-08 | Firmenich Sa | Aliphatic esters and their use as perfume ingredients |
JP2005143465A (en) * | 2003-11-20 | 2005-06-09 | Kiyomitsu Kawasaki | Method for producing sea algae flavor |
JP2006020526A (en) * | 2004-07-06 | 2006-01-26 | Kiyomitsu Kawasaki | Coffee flavor composition, and food and drink containing the same |
JP2006124490A (en) * | 2004-10-28 | 2006-05-18 | Kiyomitsu Kawasaki | Fermented-milk-like perfume composition |
US7932305B2 (en) * | 2008-06-27 | 2011-04-26 | Ethicon, Inc. | Viscous α-cyanoacrylate compositions |
WO2011121469A1 (en) * | 2010-03-29 | 2011-10-06 | Firmenich Sa | 2,4-disubstituted pyridines as perfuming ingredients |
-
2014
- 2014-07-03 ES ES14736741.1T patent/ES2638495T3/en active Active
- 2014-07-03 JP JP2016524746A patent/JP6377154B2/en active Active
- 2014-07-03 WO PCT/EP2014/064138 patent/WO2015003985A1/en active Application Filing
- 2014-07-03 EP EP14736741.1A patent/EP3019584B1/en active Active
- 2014-07-03 CN CN202110243227.9A patent/CN113025426A/en active Pending
- 2014-07-03 CN CN201480038946.5A patent/CN105378045A/en active Pending
- 2014-07-03 MX MX2015015559A patent/MX2015015559A/en unknown
- 2014-07-03 US US14/904,328 patent/US10047319B2/en active Active
- 2014-07-03 BR BR112015027807A patent/BR112015027807A2/en not_active Application Discontinuation
-
2015
- 2015-12-22 IL IL243284A patent/IL243284B/en active IP Right Grant
-
2018
- 2018-07-12 US US16/034,296 patent/US20180320105A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110097291A1 (en) * | 2008-06-04 | 2011-04-28 | Firmenich Sa | Fruity odorant |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10766850B2 (en) * | 2008-06-04 | 2020-09-08 | Firmenich Sa | Fruity odorant |
US11401483B2 (en) | 2018-06-26 | 2022-08-02 | Mitsubishi Gas Chemical Company, Inc. | Isobutyric ester compound having butyryloxy group or pivaloyloxy group at α-position and fragrance composition |
Also Published As
Publication number | Publication date |
---|---|
JP2016528332A (en) | 2016-09-15 |
CN113025426A (en) | 2021-06-25 |
US10047319B2 (en) | 2018-08-14 |
ES2638495T3 (en) | 2017-10-23 |
BR112015027807A2 (en) | 2017-08-29 |
MX2015015559A (en) | 2016-02-05 |
EP3019584A1 (en) | 2016-05-18 |
US20160130526A1 (en) | 2016-05-12 |
EP3019584B1 (en) | 2017-05-31 |
CN105378045A (en) | 2016-03-02 |
JP6377154B2 (en) | 2018-08-22 |
WO2015003985A1 (en) | 2015-01-15 |
IL243284B (en) | 2018-03-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20180320105A1 (en) | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient | |
EP2561051B1 (en) | Organic carbonates with vanilla odor | |
US8222198B2 (en) | Perfuming nitriles | |
JP2012505284A (en) | Chemically stable ingredient for lemon flavoring | |
US9068140B2 (en) | Perfuming acetal | |
EP1784374B1 (en) | Unsaturated ethers as perfuming ingredients | |
US9243210B2 (en) | Violet leaves odorants | |
WO2012110281A1 (en) | Perfuming ingredient of the galbanum family | |
US7494968B2 (en) | Non-cyclic hindered ketones as perfuming ingredient | |
US9758744B2 (en) | Floral, green odorant | |
EP2417095B1 (en) | Carboxylic derivatives as violet and/or woody odorant | |
US10023514B2 (en) | Odorants of the violet type | |
WO2011033410A1 (en) | Nitrile compounds as perfuming ingredients | |
WO2012045697A1 (en) | Esters as perfuming ingredients |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: FIRMENICH SA, SWITZERLAND Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:VIAL, CHRISTIAN;REEL/FRAME:046338/0810 Effective date: 20151027 |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: FINAL REJECTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: RESPONSE AFTER FINAL ACTION FORWARDED TO EXAMINER |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: ADVISORY ACTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NON FINAL ACTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: FINAL REJECTION MAILED |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |