DE202017107872U1 - cooling composition - Google Patents

Abstract

in Form eines ihrer Stereoisomere; und wobei R¹ eine Phenylgruppe wahlweise substituiert durch eine oder zwei C_1-3 Alkyl- oder Alkoxygruppen oder durch eine oder zwei Halogenidgruppen darstellt; R² und R³ unabhängig voneinander eine heterozyklische Gruppe mit 1 bis 3 Heteroatomen ausgewählt aus Stickstoff, Sauerstoff und Schwefel, wahlweise durch eine oder zwei C_1-3 Alkylgruppen substituiert, darstellt; und
ii) mindestens einem linearen oder verzweigten C_1-6 Alkyllactat.

Fabric composition with
i) at least one compound of the formula (I)

in the form of one of its stereoisomers; and wherein R ^{1 represents} a phenyl group optionally substituted by one or two C _1-3 alkyl or alkoxy groups or by one or two halide groups; R ² and R ³ independently represent a heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur optionally substituted by one or two C _1-3 alkyl groups; and
ii) at least one linear or branched C _1-6 alkyl lactate.

Description

Technical area

The present invention relates to the field of flavors or fragrances. In particular, it relates to a composition of matter comprising at least one compound of formula (I) and at least one linear or branched C _1-6 alkyl lactate and the use of this composition of matter in a flavor or fragrance composition. Thus, the present invention, as set forth herein, includes the composition of matter of the invention as part of an aromatizing or perfuming composition or an aromatizing or perfuming consumer product. A product obtained by the process for preparing the composition of matter according to the invention and the polymorph of the compound of formula (I), in particular N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-Tolyloxy) acetamide, also represent an object of the invention.

State of the art

The most desirable ingredients in the field of fragrances and flavors are those that provide cooling or cooling action that provides the consumer product with a freshness and cleanliness that is used in a variety of perfumed and flavored consumer products. For decades, many efforts have been made to obtain compounds having this effect.

In this regard, in the writings WO 2012/061698 and WO 2017/058594 very effective novel refrigerants have been described, which are modulators of TRPM8 (Transient Receptor Potential Channel Melastin Member 8), a channel involved in particular in the sensation of cold. These compounds are particularly effective and provide a very low concentration cooling effect. In fact, the cooling effect is observed only with traces of this powder. However, these compounds are in the form of a very fine powder at room temperature and under atmospheric pressure. Due to the strength of these compounds, they should be diluted in a solvent, especially in a solvent approved in flavored consumer products. However, these compounds have low solubility in the most common flavoring solvents.

Therefore, there is a need to dissolve these compounds to provide these compounds in dilute form. The present invention provides a solution to the above problem by the use of alkyl lactates.

Summary of the invention

The invention relates to a novel composition comprising at least one compound of the formula (I) and at least one linear or branched C _1-6 alkyl lactate, with which the use and handling of the compound of the formula (I) can be simplified.

1. (i) mindestens einer Verbindung der Formel (I)
   
   in Form eines ihrer Stereoisomere; und wobei R¹ eine wahlweise durch eine oder zwei C_1-3 Alkyl- oder Alkoxygruppen oder durch eine oder zwei Halogenidgruppen substituierte Phenylgruppe darstellt; R² und R³ unabhängig voneinander eine heterozyklische Gruppe mit 1 bis 3 Heteroatomen ausgewählt aus Stickstoff, Sauerstoff und Schwefel, wahlweise durch eine oder zwei C_1-3 Alkylgruppen substituiert, darstellen; und
2. (ii) mindestens einem linearen oder verzweigten C_1-6 Alkyllactat.

Thus, a first object of the present invention in a composition with

1. (i) at least one compound of the formula (I)
   
   in the form of one of its stereoisomers; and wherein R ^{1 represents} a phenyl group optionally substituted by one or two C _1-3 alkyl or alkoxy groups or by one or two halide groups; R ² and R ³ independently represent a heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur optionally substituted by one or two C _1-3 alkyl groups; and
2. (ii) at least one linear or branched C _1-6 alkyl lactate.

1. i) mindestens einer Stoffzusammensetzung, die mindestens eine Verbindung der Formel (I) und mindestens ein lineares oder verzweigte C_1-6 Alkyllactat umfasst;
2. ii) mindestens einem Bestandteil ausgewählt aus der Gruppe bestehend aus einem Aromaträger, einem aromatisierenden Nebenbestandteil und einer Mischung aus diesen; und
3. iii) wahlweise mindestens einem Aromazusatz.

A second object of the present invention is a flavoring composition comprising:

1. i) at least one composition of matter comprising at least one compound of formula (I) and at least one linear or branched C _1-6 alkyl lactate;
2. ii) at least one member selected from the group consisting of an aroma carrier, a flavoring minor ingredient and a mixture thereof; and
3. iii) optionally at least one flavor additive.

A third object of the present invention is a flavored consumer product having a composition of matter as defined above or an aromatizing composition as defined above.

1. i) mindestens einer Stoffzusammensetzung, die mindestens eine Verbindung der Formel (I) und mindestens ein lineares oder verzweigtes C_1-6 Alkyllactat umfasst;
2. ii) mindestens einem Bestandteil ausgewählt aus der Gruppe bestehend aus einem Duftträger, einem parfümierenden Nebenbestandteil und einer Mischung aus diesen; sowie
3. iii) wahlweise mindestens einem Duftzusatz.

Another object of the invention is a perfuming composition comprising:

1. i) at least one composition of matter comprising at least one compound of formula (I) and at least one linear or branched C _1-6 alkyl lactate;
2. ii) at least one ingredient selected from the group consisting of a fragrance carrier, a perfuming minor ingredient and a mixture of these; such as
3. iii) optionally at least one fragrance additive.

Another object of the invention is a perfumed consumer product having a composition of matter as defined above or a perfuming composition as defined above.

Another object of the invention is a method of transferring, enhancing, enhancing or modifying the flavor characteristics of a flavor composition or flavored article or surface, which process comprises adding thereto, for example, an effective amount of the composition of matter of the invention to the composition or article to give it its typical note.

1. a) Herstellen der Verbindung der Formel (I) wie in Anspruch 1 definiert durch die Reaktion einer Verbindung der Formel
   
   wobei R¹ eine wahlweise durch eine oder zwei C_1-3 Alkyl- oder Alkoxygruppen oder durch eine oder zwei Halogenidgruppen substituierte Phenylgruppe darstellt; und X eine Hydroxylgruppe, eine C_1-10 Alkoxygruppe oder ein Chloridatom darstellt, mit einer Verbindung der Formel
   
   wobei R² und R³ unabhängig voneinander eine heterozyklische Gruppe mit 1 bis 3 Heteroatomen ausgewählt aus Stickstoff, Sauerstoff und Schwefel, wahlweise durch eine oder zwei C_1-3 Alkylgruppen substituiert, darstellen;
2. b) Kristallisieren des in Schritt a) erhaltenen Reaktionsgemisches;
3. c) Filtern der Lösung des in Schritt b) erhaltenen kristallisierten Produktes;
4. d) Trocknen des in Schritt c) erhaltenen kristallisierten Produktes; und
5. e) Auflösen des in Schritt d) erhaltenen, getrockneten kristallisierten

Another object of the invention is a product obtainable by a process for producing the composition of matter as defined above, comprising the steps of:

1. a) Preparation of the compound of formula (I) as defined in claim 1 by the reaction of a compound of formula
   
   wherein R ^{1 represents} a phenyl group optionally substituted by one or two C _1-3 alkyl or alkoxy groups or by one or two halide groups; and X represents a hydroxyl group, a C _1-10 alkoxy group or a chloride atom, with a compound of the formula
   
   wherein R ² and R ³ independently represent a heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur optionally substituted by one or two C _1-3 alkyl groups;
2. b) crystallizing the reaction mixture obtained in step a);
3. c) filtering the solution of the crystallized product obtained in step b);
4. d) drying the crystallized product obtained in step c); and
5. e) dissolving the dried crystallized obtained in step d)

Product in a linear or branched C _1-6 alkyl lactate.

A final object of the invention is a crystalline form of N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide characterized by major peaks in its powder X-ray diffraction image obtained using copper K-alpha, radiation at 6.86, 12.46, 15.87, 17.38, 17.70, 17.93, 18.43, 19.46, 20.61, 22.08, 23.03, 23.43, 24.36, 26.11, 27.59, 34.68.

list of figures

• 1 represents the 13C solid state NMR spectrum obtained as mentioned in Example 3.
• 2 represents the powdery X-ray diffraction spectrum obtained as mentioned in Example 3.

Description of the invention

Surprisingly, it has now been discovered that compounds of formula (I) could be readily dissolved in linear or branched C _1-6 alkyl lactate, allowing the use of these compounds at a very low level, thereby facilitating the handling of these compounds in their solid form is.

1. i) mindestens einer Verbindung der Formel (I)
   
   in der Form eines ihrer Stereoisomere; und wobei R¹ eine wahlweise durch eine oder zwei C_1-3 Alkyl- oder Alkoxygruppen oder durch eine oder zwei Halogenidgruppen substituierte Phenylgruppe darstellt; R² und R³ unabhängig voneinander eine heterozyklische Gruppe mit 1 bis 3 Heteroatomen ausgewählt aus Stickstoff, Sauerstoff und Schwefel, wahlweise durch eine oder zwei C_1-3Alkylgruppen substituiert, darstellen; und
2. ii) mindestens einem linearen oder verzweigten C_1-6 Alkyllactat.

Therefore, a first object of the invention in a composition with

1. i) at least one compound of the formula (I)
   
   in the form of one of its stereoisomers; and wherein R ^{1 represents} a phenyl group optionally substituted by one or two C _1-3 alkyl or alkoxy groups or by one or two halide groups; R ² and R ³ independently represent a heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur optionally substituted by one or two C _1-3 alkyl groups; and
2. ii) at least one linear or branched C _1-6 alkyl lactate.

For the sake of clarity, the term "one of its stereoisomers", or the like, means the normal meaning understood by one skilled in the art, i. the compound of the formula (I) is in the form of any diastereomer, enantiomer or a mixture of these. In other words, the compound of the formula (I) has an amide functional group which may be cis or trans or a mixture of these. Furthermore, the compound of the formula (I) may additionally have at least one stereogenic center which may have a different stereochemistry (i.e., when a stereogenic center is present, the compound (I) may have an (R) or (S) configuration). Each of the stereogenic centers may be in a relative configuration R or S or a mixture of these. The compound of formula (I) may be in the form of pure enantiomer or diastereoisomer or in the form of a mixture of stereoisomers.

According to one of the preceding embodiments, R ^{1 represents} a phenyl group optionally substituted with one or two C _1-3 alkyl or alkoxy groups or with one or two halide groups. Preferably, R ^{1 represents} one with one or two C _1-3 alkyl or alkoxy groups Preferably, R ^{1 represents} a phenyl group substituted by one or two C _1-2 alkyl or alkoxy groups or by one or two fluoro groups. More preferably, R ^{1 represents} a group containing one or two methyl, The substituents for the phenyl group may be in the ortho and / or meta and / or para position with respect to the bond between the oxygen atom and the R ¹ group. Preferably, R ¹ may be selected from the group consisting of para-tolyl, 4-ethylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 3,4-dimethylphenyl and meta-tolyl. Still more preferably, R ¹ may be para-tolyl or 4-ethylphenyl. Still more preferably, R ¹ may be para-tolyl.

By the term "ortho", "meta" and "para" is meant the normal meaning in the prior art; ie the ortho position corresponds to two substituents of the phenyl group occupying positions next to each other; the metaposition corresponds to two substituents of the phenyl group representing the positions 1 and 3 take and the paraposition corresponds to two substituents of the phenyl group, which positions 1 and take 4.

In one of the above embodiments, R ² and R ³ independently represent a heterocyclic group of 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur optionally substituted with one or two C _1-3 alkyl groups. Preferably, R ² and R ^{3 3} independently represent a heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur. More preferably, R ² and R ³ independently represent a heterocyclic group having 1 to 3 heteroatoms selected from nitrogen and sulfur.

According to one of the preceding embodiments, R ^{2 represents} a heterocyclic group having one or two nitrogen atoms. Preferably, R ^{2 represents} a pyrazolyl group.

According to one of the preceding embodiments, R ³ is a heterocyclic group having one or two sulfur atoms. Preferably, R ³ represents a thiophenyl.

According to one of the preceding embodiments, the compound of the formula (I) may be selected from the group consisting of N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide, 2- (4-fluorophenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) acetamide, 2- (4-ethylphenoxy) -N- (1H-pyrazole-3-) yl) -N- (thiophen-2-ylmethyl) acetamide, 2- (4-methoxyphenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) acetamide, N- (1 H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (m-tolyloxy) -acetamide and 2- (3,4-dimethylphenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) acetamide. These compounds have a pyrazolyl group. It is known that this group consists of two tautomeric forms; i.e. 1H-pyrazol-3-yl and 1H-pyrazol-5-yl. These two forms come very quickly into balance. In other words, if the composition of matter of the invention comprises N (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide, then the composition will necessarily also comprise N- (1H-) pyrazol-5-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide. This also applies to the other compounds listed above; i.e. 2- (4-fluorophenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -acetamide is in equilibrium with 2- (4-fluorophenoxy) -N- (1H-pyrazole) 5-yl) -N- (thiophen-2-ylmethyl) acetamide, 2- (4-ethylphenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -acetamide is in equilibrium with 2- (4-ethylphenoxy-N- (1H-pyrazol-5-yl) -N- (thiophen-2-ylmethyl) acetamide, 2- (4-methoxyphenoxy) -N- (1H-pyrazole-3-) yl) - N - (Thiophen-2-ylmethyl) acetamide is in equilibrium with 2- (4-methoxyphenoxy) -N- (1H-pyrazol-5-yl) -N- (thiophen-2-ylmethyl) acetamide, N - (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (m-tolyloxy) -acetamide is in equilibrium with N- (1H-pyrazol-5-yl) -N- ( Thiophen-2-ylmethyl) -2- (m-tolyloxy) acetamide and 2- (3,4-dimethylphenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -acetamide is in the Equilibrium with 2- (3,4-dimethylphenoxy) -N- (1H-pyrazol-5-yl) -N- (thiophen-2-ylmethyl) -N- (thiophen-2-ylmethyl) -acetamide Formula (I) of N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide ,

According to one of the preceding embodiments, the composition comprises a linear or branched C _1-6 alkyl lactate. Preferably, the composition of matter comprises a linear or branched C _1-4 alkyl lactate. More preferably, the composition of matter comprises a linear C _1-4 alkyl lactate. More preferably, the composition comprises ethyl lactate.

According to one of the preceding embodiments, the composition of matter comprises from 0.1% to 20% by weight of at least one compound of formula (I) relative to the total weight of the composition and from 80% to 99.9% by weight of at least one linear or branched C _1-6 Alkyl lactate relative to the total weight of the composition. Preferably, the composition of matter comprises from 0.5% to 15% by weight of at least one compound of formula (I) relative to the total weight of the composition and from 85% by weight to 99.5% by weight of at least one linear or branched C _1-6 alkyl lactate relative to the total weight of the composition. Still more preferably, the composition of matter comprises from 1% to 10% by weight of at least one compound of formula (I) relative to the total weight of the composition and from 90% to 99% by weight of at least one linear or branched C _{1. 6} alkyl lactate relative to the total weight of the composition.

The composition of matter of the invention may be used as the flavoring ingredient. The invention relates to the use of a composition of matter with at least one compound of formula (I) and at least one linear or branched C _1-6 alkyl lactate as an aromatizing component. In other words, it relates to a method or process for transferring, enhancing, enhancing or modifying the flavor characteristics of an aromatizing composition or flavored article or surface, which process comprises adding an effective amount of the composition of matter of the invention to the composition or article eg to give this / this his / her typical note.

"Use of a composition of matter" must also be understood here as the use of any composition which contains at least one compound of the formula (I) and at least one linear or branched C _1-6 alkyl lactate and which can be used advantageously in the flavoring industry.

By "taste" is meant the designation of taste perception and taste sensation.

These compositions, which can actually be used to advantage as flavoring ingredients, are also an object of the present invention.

1. i) mindestens einer Stoffzusammensetzung mit mindestens einer Verbindung der Formel (I) und mindestens einem linearen oder verzweigten C_1-6 Alkyllactat, wie vorstehend definiert;
2. ii) mindestens einem Bestandteil ausgewählt aus der Gruppe bestehend aus einem Aromaträger, einem aromatisierenden Nebenbestandteil und einer Mischung aus diesen; sowie
3. iii) wahlweise mindestens einem Aromazusatz.

Therefore, another object of the present invention is an aromatizing composition comprising:

1. i) at least one composition of matter with at least one compound of formula (I) and at least one linear or branched C _1-6 alkyl lactate as defined above;
2. ii) at least one member selected from the group consisting of an aroma carrier, a flavoring minor ingredient and a mixture thereof; such as
3. iii) optionally at least one flavor additive.

By "aroma carrier" is meant a substance that is substantially neutral from an aroma point of view insofar as it does not substantially alter the organoleptic properties of flavoring ingredients. The carrier can be a liquid or a solid.

Suitable liquid carriers include, for example, an emulsifying system, i. a solvent and a surfactant system, or a solvent commonly used in flavoring agents. A detailed description of the nature and type of solvents commonly used in flavoring agents may not be exhaustive. Suitable solvents include, for example, propylene glycol, triacetin, Neobee, triethyl citrate, benzyl alcohol, ethanol, vegetable oil, e.g. Linseed oil, sunflower oil or coconut oil or terpene.

Suitable solid carriers include, for example, absorbent gums or polymers, or even encapsulants. Examples of such substances may be wall-forming and plasticizing substances such as mono-, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinyl alcohols, proteins or pectins, or else the reference texts such as H. Scherz, Hydrocolloids: Stabilizers, Thickening and gelling agent in food, tape 2 the series of publications food chemistry, food quality, Behr's Verlag GmbH & Co., Hamburg, 1996, substances mentioned. Encapsulation is a process known to a person skilled in the art and can be carried out, for example, using methods such as spray drying, agglomeration, extrusion, coacervation and the like.

By "flavoring minor ingredient" herein is meant a compound which is used in flavoring compositions or compositions for imparting a hedonic effect. In other words, such an ingredient, which is to be regarded as flavoring, must be recognized by a person skilled in the art in such a way that it is able to change the taste of a composition to positive and a pleasant way to convey or modify, and not just that he has a taste. The flavoring ingredient is not a compound of formula (I).

The nature and nature of the flavoring minor constituents present in the flavoring composition do not warrant a more detailed description herein, and those skilled in the art will be able to select based on their general knowledge and purpose or application and desired organoleptic effect. Generally speaking, the flavoring minor ingredients are of such diverse classes as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfur containing heterocyclic compounds, and essential oils, and the perfuming minor ingredients can be of natural or synthetic origin. Many of these minor components are in any case in reference texts such as e.g. in the book of S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of similar type, as well as in the numerous patent literature in the field of flavorings. It will also be understood that these minor components may also be compounds known for the controlled release of various types of flavoring compounds.

In particular, the following may be mentioned as flavoring minor ingredients commonly used in flavor formulations: peppermint oil and other extracts (absolute, fatty resin, washed oil), green mint oil and other extracts (absolute, fatty resin, washed oil), cornmint oil and other extracts (absolute , Fat resin, washed oil), Mentha cardiaca oil and other extracts (absolute, fat resin, washed oil), oil of all marten varieties obtainable by cultivation, eucalyptus globulus oil and other extracts (absolute, fat resin, washed oil), eucalyptol, anethole (natural and synthetic), star anise oil, fennel oil, basil oil, all types of clove oil (flower, stem, leaves), eugenol, cinnamon aldehyde, cassia oil, cinnamon bark oil, cinnamon leaf oil, cinnamon blossom oil, menthol (all grades: L and DL (racemic), pine oil ( all kinds and sources), sage oil and other extracts (absolute, fat resin, washed oil), chamomile and other extracts (absolute, fetthar z, washed oil), vanillin (natural and synthetic) and other extracts (absolute, fat resin, washed oil), all kinds of citrus oil, orange oil and other extracts (absolute, fat resin, washed oil), lime oil and other extracts (absolute, fat resin , washed oil), tangerine oil, tangerine oil, maltol, ethyl maltol, furaneol, benzophenone, all lactones, ethyl butyrate, licorice extracts (Z) -3-hexenyl acetate, (Z) -3-hexene-1-ol, (E) -2-hexene -1-ol or methyl salicylate. The skilled artisan is well aware that natural oil could be replaced by synthetic and artificial mixtures that mimic the sensory profile of natural oil. These mixtures could also be used as an aroma side ingredient.

By "flavor addition" is meant herein an ingredient that can provide additional benefits such as color, light resistance, chemical stability and so on. A detailed description of the nature and nature of the additive generally used in flavoring compositions may not be exhaustive. Nevertheless, such additives are known to a person skilled in the art who can select them on the basis of his general knowledge and according to the application or intended use.

A composition consisting of at least one compound of the formula (I), at least one linear or branched C _1-6 alkyl lactate and at least one aroma carrier constitutes a specific embodiment of the invention and an aromatizing composition comprising at least one compound of the formula (I), at least one linear or branched C _1-6 alkyl lactate, at least one flavor carrier, at least one aroma component and optionally at least one flavor additive.

According to any of the above embodiments, the inventive composition may additionally contain at least one coolant. Non-limiting examples of a suitable coolant include menthol, menthol methyl ether, menthone glycerol acetal (FEMA GRAS 3807 ), Menthone glycerol ketal (FEMA GRAS 3808 ), Menthyl lactate (FEMA GRAS 3748 ), Menthyl acetate, menthol ethylene glycol carbonate (FEMA GRAS 3805 ), Mentholpropylene glycol carbonate (FEMA GRAS 3806 ), Menthyl-N-ethyloxamate, monomethyl succinate (FEMA GRAS 3810 ), Monomenthyl glutamate (FEMA GRAS 4006 ), Menthoxy-1,2-propanediol (FEMA GRAS 3784 ), Menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849), ( 1R , 2S, 5R) -N- (4- (cyanomethyl) phenyl) menthylcarboxamide (FEMA GRAS 4496), ( 1R , 2S, 5R) -N- (2- (pyridin-2-yl) ethyl) menthylcarboxamide (FEMA GRAS 4549 ), the menthane carboxylic acid esters and amides WS- 3 , WS- 4 , WS- 5 , WS- 12 , WS- 14 and WS- 30 , as well as mixtures of these.

According to any of the above embodiments, the invention composition may contain sweeteners. Non-limiting examples of suitable sweeteners include common saccharide sweeteners, e.g. Sucrose, fructose (e.g., D-fructose), glucose (e.g., D-glucose); Sweetener compositions with natural sugar, e.g. Stevia (all types and grades), corn syrup (including high fructose corn syrup) or other types of syrup or sweetener concentrates derived from natural fruit and vegetable sources; semi-synthetic "sugar alcohol" sweeteners such as erythritol, isomalt, lactitol, mannitol, sorbitol, xylitol, maltodextrin, glycerin, threitol, arabitol, ribitol and dulcitol; artificial sweeteners such as miraculin, aspartame, superaspartame, saccharin, saccharin sodium salt, acesulfame-K, cyclamate, sodium cyclamate and alitame; other sweeteners, e.g. Trehalose, melizitose, melibiose, raffinose, palatinose, lactulose, cyclamic acid, mogroside, tagatose (eg D-tagatose), maltose, galactose (eg D-galactose), L-rhamnose, D-sorbose, maunose (eg D-maunose), Lactose, L-arabinose, D-ribose, D-glyceraldehyde, curculin, brazzein, mogroside, neohesperidin dihydrochalcone (NHDC), neotame and other aspartame derivatives, D-tryptophan, D-leucine, D-threonine, glycine, D-asparagine, D-phenylalanine, L-proline, maltitol, hydrogenated glucose syrup (HGS), magap, sucralose, lugdunam, sucrononate, sucrose, monatin, phyllodulcine, hydrogenated starch hydrolyzate (HSH), stevioside, rebaudioside A, rebaudioside D, rebaudioside M and other glycosides Stevia base, lo han guo, thaumatin, monellin, carrelam and other guanidine based sweeteners.

According to one of the preceding embodiments, the flavored composition may further contain a constituent imparting a warming, a tingling, a saliva-forming, a cleansing or an alcohol-intensifying effect, such as e.g. Paprika extract, spice extract (e.g., ginger, grains of paradise, all types of pepper including Szechwan pepper, piperine, capsaicin, jambú extract, spilanthol).

Further, the composition of matter of the invention may also be used to advantage in all fields of flavoring to positively influence or alter the taste of a consumable product to which the composition of matter is added. Thus, another object of the present invention is formed by a flavored consumer product having the above-defined composition of the invention.

The composition of matter of the invention may be added as such or as part of an aromatizing composition of the invention.

For the sake of clarity, "flavored consumer product" shall mean an edible product which may be a food or drink and which is fried or not fried and frozen or not frozen, low in fat or low in fat, marinated, baked, chilled, dried, instant, canned , reprocessed, sterilized or preserved. Thus, a flavored article of the invention contains the invention composition as well as optional positive agents according to the flavor and flavor profile of the desired edible product, e.g. spicy cubes.

The nature and nature of the ingredients of the food or drink does not warrant a more detailed description at this point, as one skilled in the art will be able to select it on the basis of its general knowledge and the nature of the product.

• • Würze oder Würzmittel, wie z.B. eine Brühe, einen pikanten Würfel, eine Pulvermischung, ein aromatisiertes Öl, eine Soße (z.B. Relish, Barbecue-Soße, Dressing, Bratensoße oder eine süße und/oder eine saure Soße), ein Salatdressing oder eine Mayonnaise;
• • Produkt auf Fleischbasis wie z.B. ein Produkt auf Geflügel-, Rindfleisch- oder Schweinefleischbasis, Meeresfrüchte, Surimi oder eine Fischwurst;
• • Suppe wie z.B. klare Suppe, Cremesuppe, Hühner- oder Rinderbrühe oder eine Tomaten- oder Spargelsuppe;
• • Produkt auf Kohlenhydratbasis wie z.B. Instantnudeln, Reis, Pasta, Kartoffelflocken oder Bratkartoffeln, Nudeln, Pizza, Tortillas, Wraps;
• • Milch- oder Fettprodukt wie z.B. Aufstrich, Käse oder normale oder fettarme Margarine, eine Butter-Margarinemischung, Butter, Erdnussbutter, Schmalz, Schmelzkäse oder aromatisierten Käse;
• • Pikantes Produkt wie z.B. Snack, Keks (z.B. Pommes oder Chips) oder ein Eiprodukt, Kartoffel-/Tortillachips, Mikrowellen-Popcorn, Nüsse, Brezeln, Reiskuchen, Reiskräcker etc.;
• • Süßwaren wie z.B. Feinbackwaren (z.B. süßes Gebäck oder Kuchen), Zuckersüßwaren (z.B. Süßigkeiten, Bonbons, kandierte Nüsse, Schokolade, Kaugummi und Bubblegum, Zuckerbrot, Pastillage, zuckerfreie Süßwaren) oder Schokoladenkonfekt;
• • Mundpflegeprodukt wie z.B. Zahnpasta, Mundspülung, Zahnpflegeprodukt (z.B. Haftcreme), Zahnspülung, Mundspray, Dentalpulver, Dentalgel oder Zahnseide;
• • Imitierte Produkte wie z.B. ein Milchprodukt (z.B. Reformkäse aus Ölen, Fetten und Verdickungsmitteln) oder Meeresfrüchte oder Fleisch (z.B. vegetarischer Fleischersatz, ein Veggie-Burger) oder Analogprodukte;
• • Haustier- oder Tiernahrung; oder
• • Getränke wie z.B. ein Heißgetränk (z.B. Tee), ein Softdrink einschließlich kohlensäurehaltigem Drink, ein alkoholisches Getränk, ein Fertiggetränk oder ein Getränkepulver.

Typical examples of the flavoring consumable product include:

• • seasoning or condiments, such as a broth, a savory cube, a powder mixture, an aromatized oil, a sauce (eg relish, barbecue sauce, dressing, gravy or a sweet and / or an acid sauce), a salad dressing or a mayonnaise ;
• • meat-based product such as a poultry, beef or pork based product, seafood, surimi or fish sausage;
• • soup such as clear soup, cream soup, chicken or beef broth or a tomato or asparagus soup;
• • carbohydrate-based product such as instant noodles, rice, pasta, potato flakes or fried potatoes, pasta, pizza, tortillas, wraps;
• • Milk or fat product such as spread, cheese or normal or low-fat margarine, a butter-margarine blend, butter, peanut butter, lard, processed cheese or flavored cheese;
• • Savory product such as snack, biscuit (eg French fries or chips) or egg product, potato / tortilla chips, microwave popcorn, nuts, pretzels, rice cakes, rice crackers, etc .;
• • confectionery such as pastries (eg sweet pastries or cakes), sugar confectionery (eg sweets, candies, candied nuts, chocolate, chewing gum and bubble gum, carrots, pastilles, sugar free confectionery) or chocolate confectionery;
• • oral care product such as toothpaste, mouthwash, dental care product (eg adhesive cream), dental rinse, oral spray, dental powder, dental gel or dental floss;
• • imitation products such as a dairy product (eg reformed cheese made from oils, fats and thickeners) or seafood or meat (eg vegetarian meat substitutes, a veggie burger) or analogue products;
• Pet or pet food; or
• • Beverages such as a hot drink (eg tea), a soft drink including a carbonated drink, an alcoholic beverage, a ready-to-drink beverage or a beverage powder.

Particularly preferred flavored consumer products in which the invention composition is used include sweets and oral care, preferably an oral care product.

Some of the aforementioned flavored consumer products may be an aggressive medium for the composition of matter of the invention, such that it may be necessary to protect them from premature decomposition, for example by encapsulation or by chemical bonding thereof to another chemical substance containing the composition of matter of the invention after a suitable incentive from the outside, such as an enzyme, light, heat or a change in pH, can release.

The proportions in which the composition of matter of the invention can be incorporated in the various products mentioned above vary within a wide range of values. These values are dependent upon the nature of the article to be flavored and the desired organoleptic effect, as well as the nature of the minor ingredients in a given base, when the composition of the invention is blended with generally art-recognized, perfuming or flavoring ingredients, solvents or additives.

For example, in the case of flavoring compositions, typical concentrations of the composition of matter of the invention are on the order of 0.001 wtppm to 1000 wtppm, based on the weight of the composition into which they are incorporated. In the case of a flavored consumable, typical concentrations are of the order of 0.001 wtppm to 1000 wtppm, more preferably from 0.5 ppm to 500ppm, most preferably from 1 to 350ppm, of the composition of matter of the invention by weight Consumable product, in which they are introduced.

The composition of matter of the invention may also be used as a perfuming ingredient. The invention relates to the use of a composition with at least one compound of the formula (I) and at least one linear or branched C _1-6 alkyl lactate as a perfuming ingredient. In other words, it relates to a method or process for transmitting, enhancing, ameliorating or modifying the odor properties of a perfuming composition or perfumed article or surface, which process comprises adding an effective amount of the composition of matter of the invention to the composition or article to give this / this, for example, his / her typical note.

By "use of a composition of matter" is also meant the use of any composition which contains at least one compound of formula (I) and at least one linear or branched C _1-6 alkyl lactate and which can be advantageously used in the perfume industry.

These compositions, which in fact can be used to advantage as perfuming ingredients, are also an object of the present invention.

1. i) mindestens einer Stoffzusammensetzung mit mindestens einer Verbindung der Formel (I) und mindestens einem linearen oder verzweigten C_1-6 Alkyllactat, wie vorstehend definiert;
2. ii) mindestens einem aus der Gruppe bestehend aus einem Duftstoffträger, einem parfümierenden Nebenbestandteil oder einer Mischung aus diesen ausgewählten Bestandteil; und
3. iii) wahlweise mindestens einem Duftzusatz.

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

1. i) at least one composition of matter with at least one compound of formula (I) and at least one linear or branched C _1-6 alkyl lactate as defined above;
2. ii) at least one selected from the group consisting of a perfume carrier, a perfuming minor ingredient or a mixture of these selected ingredient; and
3. iii) optionally at least one fragrance additive.

By "fragrance additive" is meant herein a substance that is practically neutral under a fragrance aspect; i.e. which does not substantially alter the organoleptic properties of perfuming ingredients. This carrier can be a liquid or a solid.

As the liquid carrier one may cite, as non-limiting examples, an emulsifying system, ie a solvent and a surfactant system, or a solvent generally used in the perfume field. A detailed description of the nature and type of solvents commonly used in the perfume field may not be exhaustive. However, as non-limiting examples, solvents such as butylene or propylene glycol, glycerin, dipropylene glycol and its monoethers, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol , 2- (2-ethoxyethoxy) -1-ethano, tri-ethyl citrate or mixtures thereof, which are the most common. For the compositions containing both a fragrance carrier and perfuming minor ingredients other suitable fragrance carriers than those previously described may also be selected from ethanol, water / ethanol blends, limonene or other terpenes, isoparaffins such as those sold 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), or hydrogenated castor oils, such as those sold under the trademark Cremophor® RH 40 known (origin: BASF) exist.

Solid support is intended to mean a substance to which the perfuming composition or an element of the perfuming composition can be chemically or physically bound. In general, such solid carriers are used either to stabilize the composition or to control the rate of evaporation of the compositions or some constituents. The use of a solid carrier is well known in the art and one skilled in the art knows how to achieve the desired effect. However, by way of non-limiting examples of solid carriers, one may use absorbent gums or polymers or inorganic materials such as e.g. call porous polymers, cyclodextrins, wood-based substances, organic or inorganic gels, clay, Gipstalkum or zeolites.

As other non-limiting examples of solid carriers, encapsulants may be mentioned. Examples of such substances may include wall-forming and plasticizing substances, such as mono-, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinyl alcohols, proteins or pectins or also substances which are mentioned in reference texts, such as H. Joke, hydrocolloids: stabilizers, thickening and gelling agents in food, tape 2 the series of publications food chemistry, food quality, Behr's Verlag GmbH & Co., Hamburg, 1996. The encapsulation is a process known to the expert and can be carried out for example by the use of methods such as spray drying, agglomeration or extrusion; or it consists of a coating encapsulation including coacervation and complex coacervation method.

Non-limiting examples of solid carriers may be mentioned, in particular, the core shell capsules with resins of the aminoplast, polyamide, polyester, polyurea or polyurethane type or a mixture of these (all of these resins are known to a person skilled in the art), using methods such as phase separation process, which is induced by polymerization, interfacial polymerization, coacervation or all together (all of these methods have been described in the prior art), optionally in the presence of a polymeric stabilizer or a cationic copolymer.

Resins can be prepared by the polycondensation of an aldehyde (eg formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with an amine such as urea, benzoguanamine, glycoluryl, melamine, methylolmelamine, methylated methylolmelamine, guanazole and the like and mixtures of these are manufactured. Alternatively, with preformed resins, alkylated polyamines, e.g. commercially available under the trademarks Urac® (origin: Cytec Technology Corp.), Cymel® (origin: Cytec Technology Corp.), Urecoll® or Luracoll® (origin: BASF).

Other resins are those obtained by the polycondensation of a polyol such as glycerin and a polyisocyanate such as a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate or a biuret of hexamethylene diisocyanate or a trimer of xylylene diisocyanate with trimethylolpropane (under the tradename Takenate®, origin: Mitsui Chemicals, known), a trimer of xylylene diisocyanate with trimethylolpropane and a biuret of hexamethylene diisocyanate.

Part of the trend-setting literature relating to the encapsulation of perfumes by polycondensation of amino resins, namely melamine-based resins with aldehydes, includes articles such as K. Dietrich et al. Acta Polymerica, 1989, Vol. 40, pp. 243, 325 and 683, and 1990, Vol. 41, p. 91 , These articles already describe the various parameters which influence the production of such core shell microcapsules by prior art methods, which are also described in further detail and by way of example in the patent literature. US 4,396,670 to Wiggins Teape Group Limited is a related early example thereof. Since then, many other authors have enriched the literature in this field, and it would be impossible to cover all published developments at this point, but the general knowledge in encapsulation technology is very significant. Recent related publications disclosing suitable uses of such microcapsules are disclosed, for example, in the article by HY Lee et al. Journal of Microencapsulation, 2002, Vol. 19, pp. 559-569 in the International Patent Publication WO 01/41915 or also the article by S. Bône et al, Chimia, 2011, Vol 65 , Pages 177 - 181 shown.

By "perfuming minor ingredient" herein is meant a compound used in a perfuming formulation or composition to provide a hedonic effect. In other words, such a minor ingredient, which is to be considered perfuming, must be recognized by a person skilled in the art as being capable of mediating or altering the odor of a composition in a positive or pleasant manner, and not merely as one who which has a smell. The perfuming minor ingredient does not have the formula (I).

The nature and nature of the perfuming minor constituents present in the perfuming composition do not justify a more detailed description at this point, which would in any case not be complete, the skilled person being able to do so on the basis of his general knowledge and intended use or application and to select the desired organoleptic effect. Generally speaking, these perfuming minor ingredients are of such diverse classes as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfur containing heterocyclic compounds, and essential oils, and these perfuming minor ingredients can be of natural or synthetic origin.

• - Aldehydbestandteile: Decanal, Dodecanal, 2-Methyl-Undecanal, 10-Undecanal, Octanal und/oder Nonenal;
• - Aromatische Kräuterbestandteile: Eukalyptusöl, Campher, Eukalyptol, Menthol und/oder alpha-Pinen;
• - Balsambestandteile: Kumarin, Ethylvanillin und/oder Vanillin;
• - Zitrusbestandteile: Dihydromyrcenol, Citral, Orangenöl, Linalylacetat, Citronellylnitril, Orangenterpene, Limonen, 1-P-Menthen-8-yl Acetat und/oder 1,4(8)-P-Menthadien;
• - Blumige Bestandteile: Methyldihydrojasmonat, Linalool, Citronellol, Phenylethanol, 3-(4-tert-Butylphenyl)-2-Methylpropanal, Hexylzimtaldehyd,

In particular, as perfuming minor ingredients which are commonly used in perfume formulations, the following may be mentioned:

• Aldehyde constituents: decanal, dodecanal, 2-methyl-undecanal, 10-undecanal, octanal and / or nonenal;
• - Aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, menthol and / or alpha-pinene;
• - Balsam components: coumarin, ethyl vanillin and / or vanillin;
• Citrus ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-P-menthen-8-yl acetate and / or 1,4 (8) -P-menthadiene;
• Flowery constituents: methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3- (4-tert-butylphenyl) -2-methylpropanal, hexyl cinnamic aldehyde,

• - Fruchtige Bestandteile: gamma-Undecalacton, 4-Decanolid, Ethyl 2-Methyl-Pentanoat, Hexylacetat, Ethyl 2-Methylbutanoat, gamma-Nonalacton, Allylheptanoat, 2-Phenoxyethylisobutyrat, Ethyl 2-Methyl-1,3-Dioxolan-2-Acetat und/oder Diethyl 1,4-Cyclohexandicarboxylat;
• - Grünbestandteile: 2,4-Dimethyl-3-Cyclohexen-1-Carbaldehyd, 2-tert-Butyl-1-Cyclohexylacetat, Styrallylacetat, Allyl (2-Methylbutoxy)acetat, 3-Methyl-3-decen-5-ol, Diphenylether, (Z)-3-Hexen-1-ol und/oder 1-(5,5-Dimethyl-1-Cyclohexen-1-yl)-4-Penten-1-on;
• - Moschusbestandteile: 1,4-dioxa-5,17-Cycloheptadecandion, Pentadecenolid, 3-Methyl-5-Cyclopentadecen-1-on, 1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8,-Hexamethyl-Cyclopenta-g-2-Benopyran, (1S,1'R)-2-[1-(3',3'-Dimethyl-1'-Cydohexyl)ethoxy]-2-Methylpropylpropanoat, Pentadecanolid und/oder (1S,1'R)-[1-(3',3'-Dimethyl-1'-Cyclohexyl)Ethoxycarbonyl]Methylpropanoat;
• - Holzartige Bestandteile: 1-(Octahydro-2,3,8,8-Tetramethyl-2-Naphtalenyl)-1-Ethanon, Patschuliöl, Terpenfraktionen von Patschuliöl, (1'R,E)-2-Ethyl-4-(2',2',3'-Trimethyl-3'-Cyclopenten-1'-yl)-2-Buten-1-ol, 2-Ethyl-4-(2,2,3-Trimethyl-3-Cyclopenten-1-yl)-2-Buten-1-ol, Methylcedrylketon, 5-(2,2,3-Trimethyl-3-Cyclopentenyl)-3-Methylpentan-2-ol, 1-(2,3,8,8,-Tetramethyl-1,2,3,4,6,7,8,8a-Octahydronaphthalen-2-yl)Ethan-1-on und/oder Isobornylacetat;
• - Andere Bestandteile (z.B. Bernstein, pulverförmig, würzig oder wässrig): Dodecahydro-3a,6,6,9a-Tetramethyl-Naphtho[2,1-b]Furan und beliebige seiner Stereoisomere, Heliotropin, Anisaldehyd, Eugenol, Zimtaldehyd, Nelkenöl, 3-(1,3-Benzodioxol-5-yl)-2-Methylpropanal und/oder 3-(3-lsopropyl-1-Phenyl)Butanal.

Benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4 (2H) -pyranol, betalonone, methyl 2 (Methylamino) benzoate, (E) -3-methyl-4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one, hexyl salicylate, 3,7-dimethyl- 1,6-nonadien-3-ol, 3- (4-isopropylphenyl) -2-methylpropanal, verdyl acetate, geraniol, p-menth-1-en-8-ol, 4- (1,1-dimethylethyl) -1 - Cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, high cis methyl dihydrojasmonate, 3-methyl-5-phenyl-1-pentanol, propyl propionate, geranyl acetate, tetrahydrolinalool , cis-7-P-menthanol, propyl (S) -2- (1,1-dimethylpropoxy) propanoate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4/3 (4-hydroxy) 4-methylpentyl) -3-cyclohexene-1-carbaldehyde, amylcinnamaldehyde, 4-phenyl-2-butanone, isononylacetate, 4- (1,1-dimethylethyl) -1-cyclohexylacetate, diisobutyrate and / or mixture of methylionone isomers;

• - Fruity Ingredients: gamma undecalactone, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allylheptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate and or diethyl 1,4-cyclohexanedicarboxylate;
• Green components: 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy) acetate, 3-methyl-3-decen-5-ol, diphenyl ether , (Z) -3-hexen-1-ol and / or 1- (5,5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one;
• Musk constituents: 1,4-dioxa-5,17-cycloheptadecanedione, pentadecenolide, 3-methyl-5-cyclopentadecene-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7 , 8,8, -hexamethyl-cyclopenta-g-2-benzopyran, ( 1S , 1'R) -2- [1- (3 ', 3'-dimethyl-1'-cyclohexyl) ethoxy] -2-methylpropylpropanoate, pentadecanolide and / or ( 1S , 1'R) - [1- (3 ', 3'-dimethyl-1'-cyclohexyl) ethoxycarbonyl] methyl propanoate;
• Woody constituents: 1- (octahydro-2,3,8,8-tetramethyl-2-naphthalenyl) -1-ethanone, patchouli oil, terpene fractions of patchouli oil, (1'R, E) -2-ethyl-4- (2 ', 2', 3'-trimethyl-3'-cyclopenten-1'-yl) -2-buten-1-ol, 2-ethyl-4- (2,2,3-trimethyl-3-cyclopentene-1 yl) -2-buten-1-ol, methyl cedryl ketone, 5- (2,2,3-trimethyl-3-cyclopentenyl) -3-methylpentan-2-ol, 1- (2,3,8,8, tetramethyl -1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl) ethan-1-one and / or isobornyl acetate;
• - Other ingredients (eg amber, powdery, spicy or aqueous): dodecahydro- 3a , 6,6,9a-tetramethyl-naphtho [2,1-b] furan and any of its stereoisomers, heliotropin, anisaldehyde, eugenol, cinnamic aldehyde, clove oil, 3- (1,3-benzodioxol-5-yl) -2-methylpropanal and / or 3- (3-isopropyl-1-phenyl) butanal.

Perfuming minor ingredients of the present invention need not be limited to those mentioned above, and numerous other of these minor ingredients are in any case included in reference texts such as e.g. in the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other similarly stored works, as well as in the abundant patent literature in the field of perfumes. It will also be understood that the minor ingredients may also be compounds known to release various types of perfuming compounds in a controlled manner.

By "perfume additive" is meant herein an ingredient that provides additional benefits such as e.g. a color, a specific light resistance, chemical stability, etc. can give. A detailed description of the nature and type of additives commonly used in perfuming compositions may not be exhaustive, but it should be understood that these ingredients are well known to one skilled in the art. Specific, non-limiting examples include viscosity agents (eg surfactants, thickeners, gelling agents and / or rheology modifiers), stabilizers (eg preservatives, antioxidants, heat / light and / or buffers or complexing agents such as BHT), colorants (eg and / or pigments), preservatives (eg antibacterial or antimicrobial or antifungal or anti-irritant agents), abrasives, skin coolants, fixatives, insect repellents, ointments, vitamins and mixtures thereof.

It will be understood that one skilled in the art is fully capable of providing optimal formulations for the desired effect by admixing the above-mentioned components of a perfuming composition, simply by applying the standard knowledge of the prior art as well as by trial and error methodology.

An inventive composition consisting of at least one compound of formula (I), at least one linear or branched C _1-6 alkyl lactate and at least one fragrance carrier consists of a specific embodiment of the invention and a perfuming composition with at least one compound of formula (I), at least one linear or branched C _1-6 alkyl lactate, at least one fragrance carrier, at least one perfuming minor ingredient and optionally at least one perfume additive.

Furthermore, the composition of matter of the invention may also be used to advantage in all fields of modern fragrances, i. fine or functional fragrances used to positively mediate or alter the odor of a consumable product to which the compound (I) is added. Thus, another object of the present invention is formed by a perfumed consumer product with the composition of matter of the invention as defined above.

The composition of matter of the invention may be added as such or as part of a perfuming composition of the invention.

For the sake of clarity, a "perfumed consumer product" shall refer to a consumer product that provides at least a pleasant perfuming effect on the surface or space to which it is applied (eg, skin, hair, fabrics, or domestic surface). In other words, a perfumed consumer product according to the present invention is a perfumed consumer product having a functional formulation as well as optionally additional beneficial agents corresponding to the desired consumable product and an effective olfactory amount of at least one invention compound. For the sake of clarity, this perfumed consumer product is a non-edible product.

The nature and nature of the constituents of the perfumed consumer product do not justify a more detailed description which would in any case not be complete, the skilled person being able to select them on the basis of his general knowledge and the nature and desired effect of the product.

Non-limiting examples of a suitable perfumed consumer product include a perfume such as e.g. a fine perfume, a spray perfume or Eau de Perfume, a cologne or aftershave lotion or an aftershave lotion; a fabric care product such as a liquid or solid detergent, a fabric softener, a liquid or solid fragrance enhancer, a replenisher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain care product; a personal care product such as e.g. A hair care product (e.g., a shampoo, a coloring preparation or a hairspray, a color care product, a hair product, a dental care product), a disinfectant, an intimate care product; a cosmetic preparation (e.g., a skin cream or lotion, a masking cream or a deodorant or antiperspirant (e.g., a spray or roller), depilatory, tanning or sun or aftersun product, nail product, skin cleanser, makeup); or a skin care product (e.g., a soap, shower or bath mousse, oil or gel, or a hygiene product or a foot / hand care product); an air care product, e.g. an air freshener or a "ready to use" powdered air freshener that can be used indoors (in rooms, refrigerators, cabinets, shoes or in the car) and / or in a public space (halls, hotels, shopping malls etc.); or a home care product such as a mold remover, a furniture care product, a wipe, a dishwashing detergent or a hard surface cleaner (e.g., floor, bathroom, sanitary area or window); a leather care product; a car care product such as e.g. a polish, a wax or a plastic cleaner.

Some of the aforementioned perfumed consumer products may constitute an aggressive medium for the composition of matter of the invention, such that it may be necessary to protect them against premature decomposition, for example by encapsulation or chemical bonding thereof to another chemical suitable for use Invention component after a suitable external incentive, such as an enzyme, light, heat or a change in pH.

The proportions in which the composition of matter of the invention can be incorporated into the various of the aforementioned products vary in a wide range of values. These values are dependent on the nature of the article to be perfumed and the desired organoleptic effect and the nature of the minor ingredients in a given base when the composition of matter of the present invention is blended with perfuming ingredients, solvents or additives generally used in the art.

For example, in the case of perfuming compositions, typical concentrations are of the order of 0.001 wtppm to 1000 wtppm or even more of the composition of matter of the invention, based on the weight of the composition into which they are incorporated. In the case of a perfumed consumer product, typical concentrations will be of the order of 0.01 wppm to 500 wppm or even more of the composition of matter of the invention, based on the weight of the consumable into which they are incorporated.

1. a) Herstellen der Verbindung der Formel (I) wie in Anspruch 1 definiert durch die Reaktion einer Verbindung der Formel
   
   wobei R¹ eine Phenylgruppe, wahlweise durch eine oder zwei C_1-3 Alkyl- oder Alkoxygruppen oder durch eine oder zwei Halogenidgruppen substituiert, darstellt; und X eine Hydroxylgruppe, eine C_1-10 Alkoxygruppe oder ein Chloridatom darstellt; mit einer Verbindung der Formel
   
   wobei R² und R³ unabhängig voneinander eine heterozyklische Gruppe mit 1 bis 3 Heteroatomen darstellen, die aus Stickstoff, Sauerstoff und Schwefel, wahlweise durch eine oder zwei C_1-3 Alkylgruppen substituiert, ausgewählt sind;
2. b) Kristallisieren des in Schritt a) erhaltenen Reaktionsgemisches;
3. c) Filtern der Lösung des in Schritt b) erhaltenen, kristallisierten Produktes;
4. d) Trocknen des in Schritt c) erhaltenen kristallisierten Produktes; und
5. e) Auflösen des in Schritt d) erhaltenen, getrockneten kristallisierten Produktes in einem linearen oder verzweigten C_1-6 Alkyllactat.

Another object of the present invention is a product obtainable by a process for producing the above-defined composition of matter, comprising the following step:

1. a) Preparation of the compound of formula (I) as in claim 1 defined by the reaction of a compound of the formula
   
   wherein R ^{1 represents} a phenyl group optionally substituted by one or two C _1-3 alkyl or alkoxy groups or by one or two halide groups; and X represents a hydroxyl group, a C _1-10 alkoxy group or a chloride atom; with a compound of the formula
   
   wherein R ² and R ³ independently represent a heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur optionally substituted by one or two C _1-3 alkyl groups;
2. b) crystallizing the reaction mixture obtained in step a);
3. c) filtering the solution of the crystallized product obtained in step b);
4. d) drying the crystallized product obtained in step c); and
5. e) dissolving the dried crystallized product obtained in step d) in a linear or branched C _1-6 alkyl lactate.

For the sake of clarity, the term "crystallizing" means the normal meaning in the prior art; i.e. the reaction mixture is exposed to conditions to promote the growth of the crystals.

According to one of the preceding embodiments, R ¹ , R ² and R ^{3 have the} same meaning as defined above.

According to one of the preceding embodiments, step a) is an amidation reaction. The person skilled in the art knows the conditions to be used in order to obtain the desired product. Non-limiting examples of suitable reagents / conditions for performing step a) include thermal conditions, the presence of a base, or a Lewis acid. The choice of reaction conditions depends on the nature of the substrate, and one skilled in the art will be able to select the most appropriate conditions to optimize the reaction. Preferably, step a) is carried out in the presence of a base or under heating conditions by heating the reaction mixture at a temperature above 150 ° C. More preferably, step a) is carried out in the presence of a base. Non-limiting examples of suitable bases include amine bases such as e.g. Pyridine, trimethylamine, lutidine, N, N-diisopropylethylamine or 1,8-diazabicyclo [5.4.0] undec-7-ene or alkali metal alkoxide, carbonate or hydroxide. Preferably, the base may be an alkali metal alkoxide, carbonate or hydroxide. More preferably, the base may be an alkali metal alkoxide. Still more preferably, the base may be sodium or potassium methoxide ethoxide, propoxide, butoxide or tert-butoxide. More preferably, the base may consist of sodium or potassium methoxide.

In one of the above embodiments, X represents a C _1-10 alkoxy group. Preferably X may represent a C _1-5 alkoxy group. More preferably, X may represent a C _1-3 alkoxy group. Even more preferably, X may represent a methoxy, an ethoxy or a propoxy group, even more an ethoxy group.

The compound of the formula (II) and (III) may be prepared according to one known in the art or in the art WO 2012/061698 be prepared described methods.

Step a) can be carried out in the presence or absence of a solvent. If a solvent is required or used for practical reasons, then any solvent common in such a type of reaction may be used for the purposes of the invention. Non-limiting examples include methanol, ethanol, cyclohexane, THF, Me-THF, MTBE, DME, Et ₂ O, toluene, butanone, dichloromethane, dodecane. The choice of solvent depends on the nature of the compound of formula (II) and (III) and / or base, and one skilled in the art will be able to select the most appropriate solvent to optimize the reaction.

According to one embodiment of the invention, the inventive process is carried out at a temperature between 20 ° C and 250 ° C. In particular, the temperature is in the range between 30 ° C and 150 ° C. Of course, one skilled in the art will also be able to select the preferred temperature depending on the melting and boiling point of the starting and final products as well as the desired reaction or conversion time.

According to a preceding embodiment, the crystallization from step b) is carried out by slowly cooling the reaction mixture at room temperature for a period of more than 5 hours, preferably more than 10 hours.

According to a preceding embodiment, steps c) to e) of the invention process are carried out in one and the same plant, i. an Agitated Filter Dryer, also known as Nucha Vacuum Filter Dryer, Filter Dryer or Agitated Nutsche Filter Dryer. Filtering, drying and dissolving in one and the same equipment makes it possible to reduce the handling of the compound of formula (I) obtained.

The compound of the formula (I) obtainable by carrying out the steps a) to d) is in the form of a crystal. Surprisingly, it has been discovered that the compound of formula (I) can crystallize in more than one type of three-dimensional crystal structure. In other words, several polymorphs of the compound of formula (I), and in particular N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide, have been obtained. It is known that polymorphs of a particular organic compound may have different physical properties due to their pronounced three-dimensional crystal structures, e.g. Solubility and hygroscopicity. However, it is generally not possible to predict whether a particular organic compound will form different crystalline forms, let alone predict the structure and properties of the crystalline forms. The discovery of a novel crystalline or polymorphic form of a useful compound can provide a means of improving the overall properties of a final product, such as e.g. of a flavored or perfumed consumer product. It extends the repertoire of substances that are available to a formulation scientist for execution. It may be advantageous to extend this repertoire by discovering new polymorphs of a useful compound. The most stable polymorph of the compound N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide has been obtained in the sequence of the invention process. Thus, another object of the invention is a crystalline form of N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide characterized by major peaks in its powder X-ray diffraction image obtained using copper K-alpha, radiation at 6.86, 12.46, 15.87, 17.38, 17.70, 17.93, 18.43, 19.46, 20.61, 22.08, 23.03, 23.43, 24.36, 26.11, 27.59, 34.68. The composition of matter of the invention can be prepared according to a method described below.

Examples

The invention will now be described in more detail by way of the following examples, wherein the abbreviations have the normal meaning in the prior art, the temperatures in degrees Celsius (° C) are given; the NMR spectral in CDCl ₃ (unless otherwise indicated) were recorded with a 360 or 400 MHz machine for 1 H and ¹³ C chemical shifts δ in ppm relative to TMS as standard are given, the coupling constants J are expressed in Hz.

example 1

Synthesis of the composition of matter of the invention

A 1.5 L five-necked flask equipped with a temperature probe, a reflux condenser with a nitrogen inlet, a septum, a mechanical stirrer, and a plug was charged with N- (thiophen-2-ylmethyl) -1H-pyrazol-5-amine (58 g, 0.324 Mole), 51 g of absolute ethanol and ethyl 2 - (p-Tolyloxy) acetate (72.5 g, 0.373 mol) loaded. Sodium methoxide (67 g of a 30% solution in methanol, 0.372 mol) added and the reaction mixture was heated at 55 ° C for 7 h. The reaction mixture was diluted with ethanol (297 g) and the temperature brought to 50 ° C. The pH was adjusted to 11.7 by the addition of aqueous solution containing 25% citric acid (60.7 g). Water (487 g) was added for 15 min and the resulting suspension was heated to 68 ° C. Slow cooling of the crude solution to 15 ° C was followed by filtration and washing the solids twice with 131 g of a solution containing 1 part of ethanol and 2 parts of water. The solids were then washed with demineralised water (176 g) and dried under reduced pressure to give N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) -acetamide colorless solid (74.19 g, 0.227 mol). This solid is then diluted in ethyl lactate (456 g) to give a composition containing 14% N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide and 86 To provide% ethyl lactate.

Example 2

Solubility of the compound of the formula (I)

An exact amount of the powder was weighed into a transparent 8 ml tube, 3 g of solvent was added and the tube was capped with a cap equipped with an integrated overhead stirrer. The tube was immediately transferred to a Crystalline PV Instrument (Technobis Crystallization Systems, The Netherlands) and placed in a pre-cooled reactor at 3 ° C. The sample was placed in the reactor at a rate of 0.1 ° C / min. heated to 60 ° C and stirred. Each reactor of the Crystalline PV instrument is equipped with an LED sensor and a digital camera, and data is received as a real-time transmission to detect turbidity, or as video images for visualization. The solubility temperature is reached when all the particles have dissolved. To generate a temperature-solubility curve, at least 4 samples with different concentrations are measured. The data are plotted on a Hoffmann model exponential curve, and solubility as a function of temperature can be calculated by extrapolation. This method measured the solubility of N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide in various solvents which could be used in flavor applications. The results are shown in Table 1. Table 1: Measurement of the solubility of N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide in different solvents solubility 22 ° C peppermint 2.1% Ethanol abs. 3.3% PG 0.4% triacetin 1.2% ethyl lactate 8.6% triethylcitrate 3.1% Dowanol TPM 05.04% Augeo Clean Multi 5.7%

Example 3

Analysis of polymorph of N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) -acetamide. which is obtained after the experimental part of Example 1

a) 13C solid state NMR spectroscopy

The pattern was finely ground and filled into a 4 mm ZrO2 rotor. One 13C Solid state NMR spectrum was recorded on a Bruker ABII 400 MHz spectrometer equipped with a CPMAS probe head. The sample was spun at 4000 Hz at room temperature. A total sideband suppression (CPTOSS) pulse train with a cross-polarization ramp of 2 ms was run and 10k scans were accumulated. The spectrum was converted using a 20 Hz line broadening function.

Tips: (δ in ppm vs. outer normal adamantane): 170.33, 156.04, 147.10, 143.55, 131.18, 129.04, 126.57, 125.31, 98.34, 66.48, 48.91, 21.75.

X-ray powder diffraction

The powder sample was finely ground and filled into a wafer sample holder. Diffractograms were obtained on a PANalytical Empirical Powder Diffractometer with Kα1 monochromator in reflection mode. Of the 2 Theta scan range was between 3 and 80 °.

Crystalline form of the compound characterized by major peaks in its powdery X-ray diffraction pattern (grade 2 theta): 6.86, 12.46, 15.87, 17.38, 17.70, 17.93, 18.43, 19.46, 20.61, 22.08, 23.03, 23.43, 24.36, 26.11, 27.59, 34.68. The molecules are arranged in a P21 / c space group with one molecule per unit cell.

Example 4

Preparation of a flavoring composition with a composition of matter of the invention

An aromatizing composition giving a green floral note was prepared by admixing the following ingredients: component parts by weight Ackerminze terpenfrei 520 anethole 911 4-decanolide 20 Eukapyptol 155 Eucalyptus Globulus 250 2-methoxy-4- (2-propen-1-yl) phenol 84 10% * N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide 148 allyl heptanoate 30 Peppermint oil Brazil 808 Teton mint 95 Menthol melted 4738 Hybrid peppermint oil 1420 Hedione®1) 10 4-octanolide 48 Peppermint oil Cascade USA 625 (+ -) - (3E) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-butene-2-one 38 (1R, 2S, 5R) -N-ethyl-2-isopropyl-5-methylcyclohexanecarboxamide 100 total 10000 * in ethyl lactate 1) methyl 2 - ((1RS, 2RS) -3-oxo-2-pentylcyclopentyl) acetate; Origin: Firmenich SA, Geneva, Switzerland

This flavoring composition can be applied to an oral care product or confectionery such as, e.g. Chewing gum can be added.

Example 5

Preparation of a flavoring composition with a composition of matter of the invention

An aromatizing composition imparting a spearmint note was prepared by admixing the following ingredients: component parts by weight anethole 930 (-) - 2-methyl-5- (1-propen-2-yl) -2-cyclohexen-1-one 880 10% * N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide 90 Green mint 1040 Ackerminze terpenfrei 650 Menthol melted 3280 Hybrid peppermint oil 250 linseed oil 1190 Peppermint strengthens India 680 Green mint oil 910 (1R, 2S, 5R) -N-ethyl-2-isopropyl-5-methylcyclohexanecarboxamide 100 total 10000 * in ethyl lactate

This flavoring composition can be applied to an oral care product or confectionery such as, e.g. Chewing gum can be added.

QUOTES INCLUDE IN THE DESCRIPTION

This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Cited patent literature

• WO 2012/061698 [0003, 0084]
• WO 2017/058594 [0003]
• WO 01/41915 [0062]

Cited non-patent literature

• K. Dietrich et al. Acta Polymerica, 1989, Volume 40, pages 243, 325 and 683, and 1990, Volume 41, page 91 [0062]
• H.Y. Lee et al. Journal of Microencapsulation, 2002, Vol. 19, pp. 559-569 [0062]

Claims (29)

Composition of the substance with i) at least one compound of the formula (I)

in the form of one of its stereoisomers; and wherein R ^{1 represents} a phenyl group optionally substituted by one or two C _1-3 alkyl or alkoxy groups or by one or two halide groups; R ² and R ³ independently represent a heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur optionally substituted by one or two C _1-3 alkyl groups; and ii) at least one linear or branched C _1-6 alkyl lactate. Composition after Claim 1 characterized in that R ^{1 represents} a phenyl group substituted by one or two C _1-3 alkyl or alkoxy groups or by one or two halide groups. Composition according to one of Claims 1 to 2 characterized in that R ^{1 represents} a phenyl group substituted by one or two C _1-2 alkyl or alkoxy groups or by one or two fluoro groups. Composition according to one of Claims 1 to 3 characterized in that R ^{1 represents} a phenyl group substituted by one or two methyl, ethyl, methoxy or by a fluoro group. Composition according to one of Claims 1 to 4 , characterized in that R ² and R ³ independently represent a heterocyclic group having 1 to 3 hetero atoms selected from nitrogen and sulfur. Composition according to one of Claims 1 to 5 , characterized in that R ^{2 represents} a heterocyclic group having one or two nitrogen atoms. Composition according to one of Claims 1 to 6 , characterized in that R ^{2 represents} a pyrazolyl group. Composition according to one of Claims 1 to 7 , characterized in that R ^{3 represents} a heterocyclic group having one or two sulfur atoms. Composition according to one of Claims 1 to 8th , characterized in that R ^{3 represents} a thiophenyl group. Composition according to one of Claims 1 to 9 , characterized in that the compound of formula (I) is prepared from N- (1H-pyrazol-5-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide, N- (1H-pyrazole 3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide, 2- (4-ethylphenoxy) -N- (1H-pyrazol-5-yl) -N- (thiophene) 2-ylmethyl) acetamide or 2- (4-ethylphenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) acetamide. Composition according to one of Claims 1 to 10 , characterized in that the linear or branched C _1-6 alkyl lactate consists of ethyl lactate. Composition according to one of Claims 1 to 11 , characterized in that the composition contains between 0.1% by weight and 20% by weight of at least one compound of the formula (I) as in Claim 1 to 9 defined, based on the total weight of the composition, and between 80% by weight and 99.1% by weight of at least one linear or branched C _1-6 alkyl lactate, based on the total weight of the composition. A flavoring composition comprising: i) at least one composition of matter comprising at least one compound of formula (I) and at least one linear or branched C _1-6 alkyl lactate, as in Claim 1 to 12 Are defined; ii) at least one member selected from the group consisting of an aroma carrier, a flavoring minor ingredient and a mixture thereof; and iii) optionally at least one flavor additive. Aroma composition after Claim 13 , characterized in that the composition contains at least one coolant. Flavoring composition according to Claim 14 Characterized in that the coolant from the group consisting of menthol, Mentholmethylether, Menthonglycerylacetal (FEMA GRAS 3807), Menthonglycerylketal (FEMA GRAS 3808), menthyl lactate (FEMA GRAS 3748), Metholethylenglykolcarbonat (FEMA GRAS 3805), Metholpropylenglykolcarbonat (FEMA GRAS 3806) , Menthyl-N-ethyloxamate, monomethyl succinate (FEMA GRAS 3810), monomenthyl glutamate (FEMA GRAS 4006) menthoxy-1,2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849), (1R, 2S, 5R) -N- (4- (cyanomethyl) phenyl) methylcarboxamide (FEMA GRAS 4496), (1R, 2S, 5R) -N- (2- (pyridin-2-yl) ethyl) menthylcarboxamide (FEMA GRAS 4549), the menthane carboxylic acid esters and amides WS-3, WS-4, WS-5, WS-12, WS-14, WS-30, and mixtures thereof. Flavored consumer product with a composition of matter as in one of Claims 1 to 12 defined or an aromatizing composition as defined in claims 13 to 15. Flavored consumption product after Claim 16 characterized in that the flavored consumable product is confectionery such as chewing gum, bubble gum, pastille, sugarless confectionery or an oral care product such as toothpaste, mouthwash, dentifrice, denture adhesive, dental rinse, oral spray or dental floss. Perfuming composition comprising: i) at least one composition of matter with at least one compound of formula (I) and at least one linear or branched C _1-6 alkyl lactate as in Claim 1 to 12 Are defined; ii) at least one ingredient selected from the group consisting of a fragrance carrier, a perfuming minor ingredient and a mixture of these; and iii) optionally at least one fragrance additive. Perfumed consumer product with a composition of matter as in one of Claims 1 to 12 defined or a perfuming composition as in Claim 18 Are defined. Perfumed consumption product after Claim 19 , characterized in that the perfumed consumer product is a personal care product, a cosmetic preparation, a skin care product, an air care product or a home care product. Perfumed consumption product after Claim 20 characterized in that the perfumed consumer product is a shampoo, a coloring preparation, a hair spray, a color care product, a hair product, a dental care product, a disinfectant, an intimate care product, a skin cream or lotion, a masking cream, a deodorant or antiperspirant, a depilatory agent Tanning or sun product, nail product, skin cleanser, makeup, perfumed soap, shower or bath mousse, oil or gel, foot / hand care product, hygiene product, air freshener, "ready to use" powdered air freshener, mold remover , Furniture care product, a wipe, a dishwashing detergent or a hard surface cleaner, a leather care product. Flavoring composition or flavored article or surface which is modified, enhanced, improved or modified in taste properties and by adding an effective amount of the composition of matter as in any of Claims 1 to 12 defined to this is available. A perfuming composition or perfumed article or surface which changes, strengthens, improves or modifies the odor properties and by adding an effective amount of the composition of matter as in any of Claims 1 to 12 defined to this is available. A composition obtainable by a process comprising the steps of: a) preparing a compound of formula (I) as in Claim 1 defined by the reaction of a compound of the formula

wherein R ^{1 represents} a phenyl group optionally substituted by one or two C _1-3 alkyl or alkoxy groups or one or two halide groups; and X represents a hydroxyl group, a C _1-10 alkoxy group or a chloride atom; with a compound of the formula

wherein R ² and R ³ independently represent a heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur optionally substituted by one or two C _1-3 alkyl groups; b) crystallizing the reaction mixture obtained in step a); c) filtering the solution of the crystallized product obtained in step b); d) drying the crystallized product obtained in step c); and e) dissolving the dried crystallized product obtained in step d) in a linear or branched C _1-6 alkyl lactate. Composition according to Claim 24 , characterized in that X represents a C _1-5 alkoxy group, preferably a C _1-3 alkoxy group. Fabric composition according to one of Claims 24 to 25 , characterized in that step a) is carried out in the presence of a base. Composition according to Claim 26 , characterized in that the base consists of an alkali metal alkoxide, carbonate or hydroxide. Fabric composition according to one of Claims 24 to 27 , characterized in that the steps c) to e) of the process are carried out in the same plant. A crystalline form of N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide characterized by major peaks in its X-ray powder diffraction image using copper K-alpha , Radiation at 6.86, 12.46, 15.87, 17.38, 17.70, 17.93, 18.43, 19.46, 20.61, 22.08, 23.03, 23.43, 24.36, 26.11, 27.59, 34.68.

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