1-Isopropoxy-1-oxopropan-2-yl pivalate as a perfuming ingredient

Abstract

The invention relates to the use of 1-isopropoxy-1-oxopropyl-2-pivalate in the form of any one of its stereoisomers or a mixture of these stereoisomers as a perfuming component to impart floral and fruity odor notes.

Description

[0001] The present invention is a divisional application of the invention patent application No. 201480038946.5 filed on July 3, 2014, entitled “1-isopropoxy-1-oxopropan-2-yl neopentanoate as a flavoring ingredient”. Technical Field

[0002] The present invention relates to the field of perfumery. More specifically, it relates to the use of 1-isopropoxy-1-oxopropan-2-yl pivalate in the form of any one of its stereoisomers or in the form of a mixture of these stereoisomers as a perfuming ingredient. The present invention includes the compounds of the present invention as part of a perfuming composition or as part of a perfuming consumer product. Background Art

[0003] To the best of our knowledge, the compounds of the invention are novel per se.

[0004] WO 2009 / 147565, although not specifically disclosing the compounds of the present invention, reports perfuming compounds of a general formula comprising the compounds of the present invention; nevertheless, the prior art compounds are described as fruity, whereas the compounds of the present invention have an additional, unexpected floral note. Summary of the invention

[0005] We have now surprisingly found that 1-isopropoxy-1-oxopropan-2-yl pivalate of formula (I) in the form of any of its stereoisomers or mixtures of these stereoisomers can be used as perfuming ingredient, for example to impart floral and fruity odor notes.

[0006]

[0007] For the sake of clarity, the expression "any stereoisomer thereof" or similar expressions refers to the common meaning understood by those skilled in the art, that is, the compound of the present invention may be a pure enantiomer (eg, one of the configurations S or R).

[0008] As a specific example of the compounds of the present invention, one may cite as a non-limiting example (-)-(S)-1-isopropoxy-1-oxopropan-2-yl neopentanoate, which possesses an odor with floral, rose / geranium notes, with the characteristic aspects of linalool, citronellol, geranyl acetate, and a fruity, citrus note with the characteristic aspects of lemon and bergamot. The overall pleasant effect is an interesting rose / geranium and fruity impression.

[0009] As a further example, one may cite (+)-(R)-1-isopropoxy-1-oxopropan-2-yl pivalate, which possesses an odor similar to the S enantiomer, but is distinguished from it by a slightly more pronounced fruity note and less raising than the S enantiomer.

[0010] As a further example, one may cite 1-isopropoxy-1-oxopropan-2-yl pivalate, which possesses an odor similar to the S enantiomer, but is surprisingly distinguished from it by a slightly more pronounced floral / rosy note.

[0011] According to a specific embodiment of the present invention, the compound of formula (I) is (-)-(S)-1-isopropoxy-1-oxopropan-2-yl pivalate or 1-isopropoxy-1-oxopropan-2-yl pivalate.

[0012] When the odor of the compounds of the present invention is compared to the prior art compounds described in WO2009 / 147565, such as (S)-2-(isobutyryloxy)propionic acid propyl ester, (-)-(S)-1-isopropoxy-1-oxopropan-2-yl isobutyrate or (-)-(S)-1-ethoxy-1-oxopropan-2-yl pivalate, the compounds of the present invention are distinguished from them by having a floral (rose / geranium) note which is absent or not evident in the prior art compounds. The floral note is a distinguishing feature of the odor profile of the compounds of the present invention, and not just a characteristic aspect or shade, as shown in the examples.

[0013] When compared to prior art compounds, the compounds of the present invention are also distinguished by having different types of fruity notes (in this case citrus notes). Said distinction makes the compounds of the present invention and the prior art compounds each suitable for different uses, i.e., imparting different sensory impressions.

[0014] As mentioned above, the present invention relates to the use of compounds of formula (I) as perfuming ingredients. In other words, it relates to a method for imparting, enhancing, improving or modifying the odor characteristics of a perfuming composition or a perfumed article, which method comprises adding an effective amount of at least one compound of formula (I) to said composition or article. "The use of a compound of formula (I)" is also to be understood herein as the use of any composition containing compound (I) and which can be advantageously applied in the perfumery industry.

[0015] Said compositions which can in fact be advantageously used as perfuming ingredients are also an object of the present invention.

[0016] Therefore, another object of the present invention is a perfuming composition comprising:

[0017] i) at least one compound according to the invention as defined above as perfuming ingredient;

[0018] ii) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and

[0019] iii) optionally at least one flavor adjuvant.

[0020] By "perfume carrier" it is meant here a material which is virtually neutral from a perfumery point of view, ie a material which does not significantly alter the organoleptic properties of the perfuming ingredients. The carrier may be liquid or solid.

[0021] As liquid carrier, emulsifying systems, i.e. solvents and surfactant systems, or solvents commonly used in perfumery can be cited as non-limiting examples. The detailed description of the characteristics and types of solvents commonly used in perfumery cannot be exhaustive. However, solvents such as the most commonly used dipropylene glycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate can be cited as non-limiting examples. For compositions comprising both a perfume carrier and a perfume base, in addition to the above detailed description, other suitable perfume carriers can also be ethanol, a water / ethanol mixture, limonene or other terpenes, isoparaffins such as those sold under the trademark (Source: Exxon Chemical) Those known as glycol ethers and glycol ether esters such as those sold under the trademark (Source: Dow Chemical Company) those known to the public.

[0022] As solid carriers, absorbent gels or polymers or encapsulating materials may be cited as non-limiting examples. Examples of such materials may include wall-forming and plasticizing materials such as monosaccharides, disaccharides or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins or pectins, or references such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band2 der Schriftenreihe Lebensmittelchemie, Behr's Verlag GmbH & Co., Hamburg, 1996. Encapsulation is a method well known to those skilled in the art and may be implemented, for example, by techniques such as spray drying, coagulation or extrusion; or by coating encapsulation including coagulation and complex coagulation techniques.

[0023] By "perfume base" we mean here a composition comprising at least one perfuming co-ingredient.

[0024] Said perfuming co-ingredient does not conform to formula (I). In addition, by "perfuming co-ingredient" it is meant here a compound, which is used in a perfuming preparation or composition to give a pleasant effect. In other words, such a co-ingredient to be considered as a perfuming ingredient must be recognized by a person skilled in the art as being able to impart or modify the odor of a composition in a positive or pleasant manner, rather than merely possessing an odor.

[0025] The characteristics and types of the flavoring auxiliary components present in the base material do not guarantee a more detailed description here, which is in any case not exhaustive, and those skilled in the art can select them based on their common sense and according to the intended use or application and the required sensory effect. In general, these flavoring auxiliary components belong to different chemical classifications, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenes, nitrogen-containing or sulfur-containing heterocyclic compounds and essential oils, and the flavoring auxiliary components can be natural or synthetic. In short, many of these auxiliary components are listed in references such as S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or in other works of updated versions or similar properties, as well as in a large number of patent documents in the field of perfumery. It is also understood that the auxiliary components can also be compounds known to release various types of flavoring compounds in a controlled manner.

[0026] By "perfume adjuvant" we mean here an ingredient which imparts additional added benefits such as colour, specific light resistance, chemical stability etc. A detailed description of the nature and types of adjuvants commonly used in perfuming bases cannot be exhaustive but it must be mentioned that said ingredients are well known to the person skilled in the art.

[0027] Besides perfuming compositions comprising at least one compound of formula (I), at least one perfume carrier, at least one perfume base and optionally at least one perfume adjuvant, the compositions according to the invention consisting of at least one compound of formula (I) and at least one perfume carrier also represent a particular embodiment of the present invention.

[0028] It is useful to mention here that the possibility of including more than one compound of formula (I) in the above-mentioned compositions is important since it enables the perfumer to prepare compositions and perfumes having odor notes of different compounds of the invention, thus creating new tools for his work.

[0029] For the sake of clarity, it is also understood that any mixture resulting directly from a chemical synthesis in which the compounds of the invention may be involved as starting material, intermediate or end product, such as a reaction medium which has not been sufficiently purified, cannot be considered as a perfuming composition according to the invention, as long as said mixture does not provide the compounds of the invention in a form suitable for perfumery. Therefore, unpurified reaction mixtures are generally excluded from the present invention, unless otherwise stated.

[0030] Furthermore, the compounds of the invention can also be advantageously used in all areas of modern perfumery (i.e. fine perfumery or functional perfumery) to positively impart or modify the smell of a consumer product to which said compound (I) is added. Thus, another object of the present invention is represented by a perfumed consumer product comprising as perfumed ingredient at least one compound of formula (I) as defined above.

[0031] The compounds of the invention can be added as such or as part of a perfuming composition of the invention.

[0032] For the sake of clarity, it must be mentioned that a "perfuming consumer product" refers to a consumer product intended to deliver at least one perfuming effect, in other words, it is a perfumed consumer product. For the sake of clarity, it must be mentioned that a "perfuming consumer base" refers to a functional formulation corresponding to a consumer product, and optionally additional benefit agents, which is compatible with the perfuming ingredients and intended to deliver a pleasant odor to the surface to which it is applied (e.g., skin, hair, fabric or household surface). In other words, the perfuming consumer product of the present invention comprises a functional formulation corresponding to a desired consumer product (e.g., a deodorant or air freshener), and optionally additional benefit agents, and an olfactory effective amount of at least one compound of the present invention.

[0033] The nature and types of components of perfuming consumer products do not warrant a more detailed description here, which is in no way exhaustive, and a person skilled in the art will be able to choose them based on his general knowledge and according to the nature of the product in question and the desired effect.

[0034] Non-limiting examples of suitable perfumed consumer products may be perfumes, such as fine perfumes, colognes or aftershaves; fabric care products, such as liquid or solid detergents, fabric softeners, fabric refreshers, ironing water, paper, or bleaching agents; body care products, such as hair care products (such as shampoos, colorants or hair sprays), cosmetic preparations (such as vanishing creams or deodorants or antiperspirants), or skin care products (such as soaps, bath gels, bath oils or shower gels, or hygiene products); air care products, such as air fresheners or "ready-to-use" powdered air fresheners; or household care products, such as wipes, dishwashing detergents or hard surface detergents.

[0035] Some of the above-mentioned perfuming consumer products may be aggressive media for the compounds of the invention and it may be necessary to protect the compounds of the invention from premature decomposition, for example by encapsulation or by chemically combining them with another chemical substance suitable for releasing the ingredients of the invention under appropriate external stimuli (such as enzymes, light, heat or changes in pH).

[0036] The proportions in which the compounds of the invention can be incorporated into the various products or compositions mentioned above vary within a wide range of values. These values ​​depend on the nature of the product to be perfumed and on the desired organoleptic effect, and also on the nature of the co-ingredients in a given base when the compounds of the invention are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.

[0037] For example, in the case of perfuming compositions, typical concentrations of the compounds of the invention are about 1% to 50% by weight or even higher, based on the weight of the composition in which they are incorporated. When these compounds are incorporated into perfuming consumer products, their concentrations may be lower than the above values, for example about 0.05% to 20% by weight, the percentages being calculated relative to the weight of the product.

[0038] The compounds of the present invention can be prepared according to the methods described in the examples below. DETAILED DESCRIPTION

[0039] The present invention will now be further described in detail by way of the following examples, in which abbreviations have their usual meanings in the art, temperatures are in degrees Celsius (° C.); NMR spectral data are obtained by spectroscopy at 360 or 400 MHz in CDCl3 (unless otherwise specified). 1 H and 13 The chemical shift δ is based on TMS and the unit is ppm. The coupling constant J is expressed in Hz.

[0040] Example 1

[0041] Synthesis of compounds of formula (I)

[0042] Preparation of (-)-(S)-1-isopropoxy-1-oxopropan-2-yl pivalate:

[0043] To 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) was slowly added with 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 and water, and dried over Na2SO4. The dichloromethane was evaporated to give a residue (96.7 g), which was purified by Vigreux column (Bp 12mbars =80~85°) and then distilled rapidly using a Fischer column (Bp 12mbars =83-85°) to obtain 51.1 g (yield = 47%) of pure (-)-(S)-1-isopropoxy-1-oxopropan-2-yl pivalate.

[0044] [α] 20 D =-32.6°(3.1%,CHCl3).

[0045] 1 H-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).

[0046] 13 C-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).

[0047] The R enantiomer or the racemate can be obtained completely by the same method, except that the starting material used is R-(+)-isopropyl lactate or isopropyl lactate, respectively.

[0048] Example 2

[0049] Preparation of perfuming compositions

[0050] Prepare a perfumed composition for an "all-purpose cleaner" by mixing the following ingredients:

[0051]

[0052]

[0053] *In dipropylene glycol

[0054] 1) 4-Cyclohexyl-2-methyl-2-butanol; Source: Firmenich SA, Geneva, Switzerland

[0055] The effect obtained by adding 4000 parts by weight of the following compounds to the above composition is described as:

[0056] a) (-)-(S)-1-isopropoxy-1-oxopropan-2-yl neopentanoate brings fruity and floral-geranium characteristics to the aroma. The geranium characteristics obtained when adding the compound of the present invention are comparable to the addition of an 80 / 20 mixture of (S)-2-(1,1-dimethylpropoxy)propanoic acid propyl ester (see EP 1069176) and citronellol (3200 parts and 800 parts respectively);

[0057] b) (S)-2-(isobutyryloxy)propyl propionate (WO2009 / 147565) does not impart a floral note, but has a fruity aroma similar to (S)-2-(1,1-dimethylpropoxy)propyl propionate (see EP 1069176), but is less fragrant overall;

[0058] c) (-)-(S)-1-ethoxy-1-oxopropan-2-yl neopentanoate (WO2009 / 147565) does not impart a floral note, but has a butyric, fruity aroma reminiscent of apple and strawberry;

[0059] d) (S)-2-(propionyloxy)propionic acid ethyl ester (WO2009 / 147565) does not impart floral notes, but has fruity / grassy, ​​metallic, wine / rhubarb notes; or

[0060] e) (-)-(S)-1-isopropoxy-1-oxopropan-2-yl isobutyrate (WO 2009 / 147565) does not impart a floral note, but only a butyric fruity aroma reminiscent of apricots.

[0061] Example 3

[0062] Preparation of perfuming compositions

[0063] A perfuming composition of the "Eau de Cologne" type is prepared by mixing the following ingredients:

[0064]

[0065] 1) 3-Methyl-5-cyclopentadecen-1-one; Source: Firmenich SA, Geneva, Switzerland

[0066] The effect obtained by adding 2000 parts by weight of the following compounds to the above composition is described as:

[0067] a) (-)-(S)-1-isopropoxy-1-oxopropan-2-yl neopentanoate imparts a rounded citrus note and more fruity aroma, and adds a floral geranium / rose note. The same floral effect as that imparted by the compound of the present invention can be obtained by adding a mixture of approximately 75% of propyl (S)-2-(1,1-dimethylpropoxy)propionate (see EP 1069176) and 25% of citronellol (1500 parts and 500 parts respectively), but not by adding 2000 parts of propyl (S)-2-(1,1-dimethylpropoxy)propionate (see EP 1069176) alone;

[0068] b) Propyl (S)-2-(isobutyryloxy)propionate (WO2009 / 147565) does not impart floral notes, but bursts with aromatic notes and adds less fruitiness to the citrus notes than the compounds of the present invention;

[0069] c) (S)-2-(propionyloxy)propionic acid ethyl ester (WO2009 / 147565) does not impart a floral fragrance, but makes the composition have a bitter grassy and sour aroma; or

[0070] d) (-)-(S)-1-ethoxy-1-oxopropan-2-yl neopentanoate (WO2009 / 147565) does not impart a floral note, but adds a sweet butyric fruity note, which together with crystal moss creates a typical fruity Chypre effect.

Claims

1. Use of the compound (-)-(S)-1-isopropoxy-1-oxopropan-2-yl neopentanoate as a perfuming ingredient for imparting floral and fruity odor notes, wherein the floral note is a rose / geranium fragrance note.

2. A perfuming composition comprising i) the compound (-)-(S)-1-isopropoxy-1-oxopropan-2-yl neopentanoate, to impart a floral and fruity odor note, wherein the floral note is a rose / geranium note; ii) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and iii) optionally at least one flavor adjuvant.

3. A perfumed consumer product comprising the compound (-)-(S)-1-isopropoxy-1-oxopropan-2-yl neopentanoate to impart a floral and fruity odor note, wherein the floral note is a rose / geranium note.

4. The perfumed consumer product according to claim 3, characterized in that The perfumed consumer product is a perfume, a fabric care product, a body care product, an air care product or a home care product.

5. The flavored consumer product according to claim 3, characterized in that The perfumed consumer product is a fine perfume, aftershave, fabric softener, fabric refresher, ironing water, bleach, shampoo, colorant, hair spray, vanishing cream, deodorant, antiperspirant, soap, bath gel, bath oil or shower gel, air freshener, wipe or hard surface detergent.

6. The flavored consumer product according to claim 3, characterized in that The perfumed consumer product is a cologne or a hygiene product.

7. The flavored consumer product according to claim 3, characterized in that The perfumed consumer product is a liquid detergent, a solid detergent or a "ready-to-use" powdered air freshener.

8. The flavored consumer product according to claim 3, characterized in that The perfumed consumer product is paper or dishwashing detergent.

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