Composition having a lily of the valley odor

Abstract

The present invention relates to a composition of matter comprising: a) at least one compound of formula (I), in the form of any one of its isomers or a mixture of these isomers; wherein R 1 represents a hydrogen atom or a C 1‑2 alkyl group; and R represents a group of formula -CH2C(Me)2OH; said R being a meta or para substituent of the aromatic ring with respect to position 1 or a mixture thereof; and b) at least one compound of formula (II), in the form of any one of its isomers or a mixture of these isomers; wherein R 1 and R have the same meaning as defined in formula (I); said R being an ortho, meta or para substituent of the aromatic ring with respect to position 1 or a mixture thereof; as well as their use as perfuming ingredient, as well as compositions and consumer products comprising such composition of matter and a process for the preparation thereof.

Description

[0001] This invention is a divisional application of patent application No. 201880006956.9, entitled "Composition with Lily of the Valley Scent", filed on January 17, 2018. Technical Field

[0002] This invention relates to the field of fragrances. More specifically, this invention relates to a composition comprising phenylpropanal derivatives of formulas (I) and (II) as a fragrance ingredient, as well as compositions and consumer products comprising such compositions. Methods for obtaining the compositions of this invention are also part of this invention. Background Technology

[0003] One of the key ingredients in the spice industry (4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde; Source: International Flavors & Fragrances, USA). This ingredient is appreciated for its floral, lily-of-the-valley scent, which is similar to... The fragrance notes imparted by (2-methyl-3-[4-(2-methyl-2-propyl)phenyl]propanal, a trademark of Givaudan-Roure SA, Vernier, and Suisse) are different; however, the use of this ingredient is restricted because it is listed as an allergen.

[0004] Therefore, it is necessary to develop something that can be used as... A novel fragrance ingredient as an alternative.

[0005] This invention provides a composition comprising at least one compound of formula (I) and at least one compound of formula (II), having the properties of... Very similar characteristic smells.

[0006] To the best of our knowledge, only one structural analogue closely related to compounds of formula (I) and (II) has been reported in the literature as a flavoring ingredient. In fact, 3-(4-(2-hydroxypropane-2-yl)phenyl)butanal has been reported in US 4491537 to have a green, woody, and peach-like aroma, which are sensory characteristics completely different from those of the compounds of this invention.

[0007] Another analogue, 3-(3-(3-hydroxy-3-methylbutyl)phenyl)-2-methylpropanal, is disclosed in WO2014207205, without specifying its sensory properties. This compound has been used as an intermediate in the flavoring ingredient 2-methyl-3-(3-(3-methylbut-3-en-1-yl)phenyl)propanal. Neither of these prior art documents reports or implies any sensory properties of compositions comprising compounds of formula (I) and (II), or any use of these compounds in the fragrance industry. Summary of the Invention

[0008] This invention relates to a composition comprising at least one compound of formula (I) and at least one compound of formula (II), which can be used as... Substitute.

[0009] Therefore, the first object of the present invention is a material composition comprising: a) at least one compound of formula (I),

[0010]

[0011] It takes the form of any one of its isomers or a mixture of these isomers; wherein R 1 Represents a hydrogen atom or C 1-2 Alkyl; and R represents a group of the formula –CH2C(Me)2OH; relative to position 1, said R is a meta- or para-substituent of an aromatic ring or a mixture thereof; and b) at least one compound of formula (II),

[0012]

[0013] It takes the form of any one of its isomers or a mixture of these isomers; wherein R and R 1 It has the same meaning as defined in formula (I); relative to position 1, R is an ortho, meta, para substituent of the aromatic ring or a mixture thereof.

[0014] A second object of the present invention is the use of a material composition as a flavoring ingredient, the material composition comprising at least one compound of formula (I) and at least one compound of formula (II) as defined above.

[0015] A third object of the present invention is a flavoring composition comprising:

[0016] i) at least one composition comprising at least one compound of formula (I) and at least one compound of formula (II) as defined above;

[0017] ii) at least one ingredient selected from the group consisting of a flavor carrier and a flavor base; and

[0018] iii) Optionally, at least one flavoring adjuvant.

[0019] Another object of the present invention is a scented consumer product comprising at least one substance composition comprising at least one compound of formula (I) and at least one compound of formula (II) as defined above, or a scented composition as defined above.

[0020] Another object of the present invention is a method for preparing a composition of substances as defined above, comprising a hydroformylation step of a compound of formula (V).

[0021]

[0022] Among them, R 1 R has the same meaning as defined above; relative to position 1, R is an ortho, meta, para substituent of the aromatic ring or a mixture thereof.

[0023] Another object of the present invention is the compound of formula (V).

[0024]

[0025] Among them, R 1 R has the same meaning as defined above; relative to position 1, R is an ortho- or meta-substituent of the aromatic ring or a mixture thereof.

[0026] A final object of the present invention is a method for imparting, enhancing, improving or altering the odor characteristics of a flavored composition or a flavored article, the method comprising adding an effective amount of at least one substance composition as defined above to the composition or article. Detailed Implementation

[0027] Unless otherwise stated, percentage (%) means weight percentage relative to the total weight of the composition.

[0028] Surprisingly, it has now been discovered that compositions of substances comprising at least one compound of formula (I) and at least one compound of formula (II) exhibit very interesting properties in areas of particular interest. It has a lily-of-the-valley twist scent. This composition has never been disclosed before.

[0029] The first object of the present invention is a material composition comprising:

[0030] a) at least one compound of formula (I),

[0031]

[0032] It takes the form of any one of its isomers or a mixture of these isomers; wherein R 1 Represents a hydrogen atom or C 1-2Alkyl; and R represents a group of the formula -CH2C(Me)2OH; relative to position 1, said R is a meta- or para-substituent of an aromatic ring, or a mixture thereof; and

[0033] b) at least one compound of formula (II),

[0034]

[0035] It takes the form of any one of its isomers or a mixture of these isomers;

[0036] Where R and R 1 It has the same meaning as defined in formula (I); relative to position 1, R is an ortho, meta, para substituent of the aromatic ring, or a mixture thereof. The composition can be used as a flavoring ingredient, for example, in... It imparts a lily-of-the-valley scent profile.

[0037] For clarity, let's use the expressions "R and R" 1 The term "having the same meaning as in formula (I)" or similar means the normal meaning understood by those skilled in the art, that is, the material composition of the present invention comprises compounds of formula (I) and formula (II), wherein the R group of the compound of formula (I) is the same as the R group of the compound of formula (II), and the R group of the compound of formula (I) is... 1 The group and the R of the compound of formula (II) 1 The substituents are the same. In other words, the substituents of compound (I) are the same as those of compound (II).

[0038] For clarity, the use of the term "material composition" or similar terms refers to the normal meaning understood by those skilled in the art, namely, the presence of at least two different compounds (not stereoisomers). According to any of the above embodiments, the material composition of the present invention may comprise at least one compound of formula (I) in an amount of 0.5% w / w to 60% w / w and at least one compound of formula (II) in an amount of at least 40% w / w, relative to the total weight of the material composition. Preferably, the material composition of the present invention may comprise at least one compound of formula (I) in an amount of 0.5% w / w to 49% w / w and at least one compound of formula (II) in an amount of at least 50% w / w, relative to the total weight of the material composition. Preferably, the material composition of the present invention may comprise at least one compound of formula (I) in an amount of 1% w / w to 30% w / w and at least one compound of formula (II) in an amount of at least 70% w / w, relative to the total weight of the material composition. Even more preferably, the material composition of the present invention may contain at least one compound of formula (I) in a content of 1% w / w to 15% w / w and at least one compound of formula (II) in a content of at least 85% w / w, relative to the total weight of the material composition.

[0039] For clarity, the use of the terms "any of its isomers or mixtures of such isomers" or similar terms means the normal meaning understood by those skilled in the art, that is, the compounds of the present invention can be pure enantiomers (if chiral) or mixtures of enantiomers; pure regio isomers or mixtures of regio isomers; or mixtures thereof.

[0040] For clarity, the use of terms such as "pure regioisomers or mixtures of regioisomers" or similar terms refers to the normal meaning understood by those skilled in the art, namely, that the R group of compound (I) relative to position 1 can be a meta-, para-, or a mixture thereof, and the R group of compound (II) relative to position 1 can be an ortho-, meta-, para-, or a mixture thereof. For example, the composition of the present invention may comprise a compound that is a pure regioisomer, for example, where R is a para-substituent of an aromatic ring relative to position 1; or, for example, a mixture of two regioisomers of a compound, wherein R is a para-substituent of an aromatic ring relative to position 1 and a meta-substituent of an aromatic ring relative to position 1. In other words, a compound of formula (I) can be of formula (I”) (i.e., R is a meta-substituent of the aromatic ring relative to position 1), or formula (I”’) (i.e., R is a para-substituent of the aromatic ring relative to position 1), or a mixture thereof, while a compound of formula (II) can be of formula (II’) (i.e., R is an ortho-substituent of the aromatic ring relative to position 1), formula (II”) (i.e., R is a meta-substituent of the aromatic ring relative to position 1), formula (II”’) (i.e., R is a para-substituent of the aromatic ring relative to position 1), or a mixture thereof. Each compound of formula (I”) or (I”’) represents a regioisomer of a compound of formula (I), and each compound of formula (II’), (II”) or (II”’) represents a regioisomer of a compound of formula (II). A compound of formula (II’) can also be called an ortho-regioisomer. Compounds of formula (I’) and (II’) can also be called ortho-regioisomers. Compounds of formula (I”) and (II”’) can also be called meta-regioisomers. Compounds of formulas (I”’) and (II”’) can also be called para-regioisomers.

[0041]

[0042] According to any of the above embodiments, the material composition of the present invention comprises at least one compound of formula (I) and at least one compound of formula (II), wherein the R group of the compound of formula (I) is a para- and / or meta-substituent relative to position 1, and the R group of the compound of formula (II) is a para- and / or meta-substituent relative to position 1. Preferably, the material composition of the present invention comprises at least one compound of formula (I) and at least one compound of formula (II) being the same regioisomer, for example, the material composition comprises at least a para-regioisomer of formula (I) (compound of formula (I”’)) and at least a para-regioisomer of formula (II) (compound of formula (II”’)).

[0043] According to any of the above embodiments, the material composition of the present invention comprises less than 5% w / w of a meta-regioisomer; that is, compounds of formula (II”) and (I”). Preferably, the material composition of the present invention comprises less than 2% w / w of a meta-regioisomer; that is, compounds of formula (II”) and (I”).

[0044] According to any of the above embodiments, the material composition of the present invention comprises:

[0045] - up to 20% w / w of compound (II');

[0046] - up to 45% w / w of formula (II”) compounds;

[0047] - Up to 25% w / w of compounds of formula (I”);

[0048] Compounds of formula (II”') with a concentration of -25% to 99% w / w;

[0049] Compounds of formula (I”') ranging from -0.5% to 49% w / w;

[0050] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0051] Preferably, the material composition of the present invention comprises:

[0052] - up to 20% w / w of compound (II');

[0053] - up to 10% w / w of compounds of formula (II”);

[0054] - Up to 15% w / w of compounds of formula (I”);

[0055] Compounds of formula (II”') with a concentration of -25% to 99% w / w;

[0056] Compounds of formula (I”') ranging from -0.5% to 49% w / w;

[0057] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0058] Preferably, the material composition of the present invention comprises:

[0059] - up to 20% w / w of compound (II');

[0060] - Up to 2% w / w of formula (II”) compounds;

[0061] - Up to 5% w / w of the (I”) compound;

[0062] Compounds of formula (II”') with a concentration of -25% to 99% w / w;

[0063] Compounds of formula (I”') ranging from -0.5% to 49% w / w;

[0064] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0065] Preferably, the material composition of the present invention comprises:

[0066] - up to 10% w / w of compound (II');

[0067] - Up to 2% w / w of formula (II”) compounds;

[0068] - up to 1% w / w of compounds of formula (I”);

[0069] Compounds of formula (II”') with a concentration of -25% to 99% w / w;

[0070] Compounds of formula (I”') ranging from -0.5% to 49% w / w;

[0071] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0072] Preferably, the material composition of the present invention comprises:

[0073] - up to 5% w / w of compound of formula (II');

[0074] - Up to 2% w / w of formula (II”) compounds;

[0075] - up to 1% w / w of compounds of formula (I”);

[0076] Compounds of formula (II”') with a concentration of -25% to 99% w / w;

[0077] Compounds of formula (I”') ranging from -0.5% to 49% w / w;

[0078] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0079] Preferably, the material composition of the present invention comprises:

[0080] - Up to 2% w / w of formula (II”) compounds;

[0081] Compounds of formula (II”') with a concentration of -25% to 99% w / w;

[0082] Compounds of formula (I”') ranging from -0.5% to 49% w / w;

[0083] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0084] Even more preferably, the mixture comprises:

[0085] Compounds of formula (II”') with a concentration of -50 to 99% w / w;

[0086] Compounds of formula (I”') with a concentration of -1 to 49% w / w;

[0087] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0088] Even more preferably, the mixture comprises:

[0089] Compounds of formula (II”') with a concentration of -70 to 99% w / w;

[0090] Compounds of formula (I”') with a concentration of -1 to 30% w / w;

[0091] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0092] Even more preferably, the mixture comprises:

[0093] Compounds of formula (II”') with a w / w ratio of -80 to 99%;

[0094] Compounds of formula (I”') with a concentration of -1 to 20% w / w;

[0095] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0096] Even more preferably, the mixture comprises:

[0097] Compounds of formula (II”') with a w / w ratio of -90 to 99%;

[0098] Compounds of formula (I”') with a concentration of -1 to 10% w / w;

[0099] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0100] According to a particular embodiment, the material composition of the present invention comprises:

[0101] Compounds of formula (II”') with a w / w ratio of -80 to 99%;

[0102] Compounds of formula (I”') and formula (II') with a concentration of -1 to 20% w / w;

[0103] The percentages relative to the total weight of the material composition are expressed as weight / weight.

[0104] According to any of the above embodiments, the material composition of the present invention may comprise only one regioisomer of formula (I) and only one regioisomer of formula (II), wherein the regioisomer of formula (I) is the same as the regioisomer of formula (II); that is, a composition comprising a compound wherein, relative to position 1, the R group is a meta-substituent (composition comprising compounds of formulas (I”) and (II”) or a composition comprising a compound wherein, relative to position 1, the R group is a para-substituent (composition comprising compounds of formulas (I”’) and (II”’). Preferably, the material composition of the present invention comprises a compound wherein, relative to position 1, the R group is a para-substituent.

[0105] According to any embodiment of the present invention, compound (I) conforms to compound (III).

[0106]

[0107] It takes the form of any one of its isomers or a mixture of these isomers, wherein R 1 It has the same meaning as the definition above.

[0108] According to any embodiment of the invention, compound (II) conforms to compound (IV).

[0109]

[0110] Where R 1 It has the same meaning as the definition above.

[0111] According to any embodiment of the invention, the compound of formula (I) or (II) is C 13 -C 15 , or even C 13 -C 14 Compounds.

[0112] According to any embodiment of the invention, the material composition of the invention comprises a compound wherein R 1 Represents a hydrogen atom or C 1-2 Alkyl group. Preferably, R 1 Represents a hydrogen atom or a methyl group. Most preferably, R 1 It represents a hydrogen atom.

[0113] To the best of our knowledge, the material composition reported above is novel, and is therefore the object of this invention.

[0114] According to any of the above embodiments of the present invention, the material composition of the present invention comprises 3-[4-(2-hydroxy-2-methylpropyl)phenyl]propanal and 2-[4-(2-hydroxy-2-methylpropyl)phenyl]propanal. Specifically, material compositions comprising 50% w / w to 99% w / w of 3-[4-(2-hydroxy-2-methylpropyl)phenyl]propanal and 0.5% w / w to 49% w / w of 2-[4-(2-hydroxy-2-methylpropyl)phenyl]propanal relative to the weight of the material composition can be cited. As a specific example, and as a non-limiting example, a composition comprising about 80.1% w / w of 3-[4-(2-hydroxy-2-methylpropyl)phenyl]propanal and 19.3% w / w of 2-[4-(2-hydroxy-2-methylpropyl)phenyl]propanal can be cited. The material composition is characterized by having very close... The overall olfactory characteristics of (4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde; source: International Flavors & Fragrances, USA); that is, the composition of the present invention has the olfactory characteristics of lily of the valley, hydroxycitronellol and A very typical "wetting" effect combined. The material composition of the present invention can be used to impart... The odor. In other words, the material composition of the present invention can be used as an olfactory substitute for this ingredient, which is highly sought after in the industry because... Its use is now restricted due to allergies. In fact, when the aforementioned substance composition is combined with... In comparison, the material compositions of the present invention differ by being more lingering and potent (thus allowing even lower dose levels compared to prior art compounds) and having improved radioactivity, while (compared to) Many alternatives (conversely) also provide A unique "moisturizing" effect.

[0115] Other examples of the material compositions of the present invention include compositions comprising about 75.2% w / w 3-[4-(2-hydroxy-2-methylpropyl)phenyl]propanal, 22.2% w / w 2-[4-(2-hydroxy-2-methylpropyl)phenyl]propanal, about 1.3% w / w 3-[3-(2-hydroxy-2-methylpropyl)phenyl]propanal, and about 0.4% w / w 2-[3-(2-hydroxy-2-methylpropyl)phenyl]propanal, which have a similar odor to those described above.

[0116] As described above, the present invention relates to the use of a composition comprising at least one compound of formula (I) and at least one compound of formula (II) as a flavoring ingredient. In other words, it relates to a method of imparting, enhancing, improving, or altering the odor properties of a flavored composition or flavored article, the method comprising adding an effective amount of at least the composition of the present invention to said composition or article. By "use of the composition," it must also be understood herein to mean the use of any composition containing at least one compound of formula (I) and at least one compound of formula (II), which can be advantageously used in the fragrance industry.

[0117] In particular, the method or use may involve replacing [the previous method] in a flavoring composition. Methods to impart, enhance, improve, or alter the floral, lily of the valley, or hydroxycitronellol aroma notes of a scented composition or product.

[0118] In fact, the composition can be advantageously used as a flavoring ingredient, which is also an object of the present invention.

[0119] Therefore, another object of the present invention is a flavoring composition comprising:

[0120] i) at least one of the material compositions of the present invention as a flavoring ingredient, said material composition comprising at least one compound of formula (I) and at least one compound of formula (II) as defined above;

[0121] ii) at least one ingredient selected from the group consisting of a flavor carrier and a flavor base; and

[0122] iii) Optionally, at least one flavoring adjuvant.

[0123] The term "fragrance carrier" refers to a material that is virtually neutral from a fragrance perspective, meaning it does not significantly alter the sensory properties of the flavoring ingredients. The carrier can be liquid or solid.

[0124] As liquid carriers, emulsion systems, i.e., solvent and surfactant systems, or solvents commonly used in fragrances, can be listed as non-limiting examples. A detailed description of the properties and types of solvents commonly used in fragrances is impossible to exhaust. However, solvents such as butanediol or propylene glycol, glycerol, dipropylene glycol and its monoethers, 1,2,3-propanetriyltriacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetoxypropyl-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, triethyl citrate, or mixtures thereof are the most commonly used. For compositions containing both fragrance carriers and fragrance bases, in addition to those detailed above, other suitable fragrance carriers may also be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins, such as those marketed under trademarks... Those known to the public (source: Exxon Chemical), or glycol ethers and glycol ether esters, such as those marketed under trademarks Those commonly known (source: Dow Chemical Company), or hydrogenated castor oil, such as those marketed as trademarks... RH 40, those that are well-known (Source: BASF).

[0125] A solid carrier is a material to which a flavoring composition or certain components of a flavoring composition can be chemically or physically bonded. Such solid carriers are typically used to stabilize the composition or control the evaporation rate of the composition or certain components. Solid carriers are currently used in the art, and those skilled in the art know how to achieve the desired effect. However, as non-limiting examples of solid carriers, examples include absorbent resins or polymers or inorganic materials such as porous polymers, cyclodextrins, wood-based materials, organic or inorganic gels, clay, gypsum, talc, or zeolite.

[0126] Other non-limiting examples of solid carriers include encapsulating materials. Examples of such materials may include wall-forming materials and plasticizers, such as monosaccharides, disaccharides or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins or pectins, or, as in references such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2der Schriftenreihe Lebensmittelchemie, The materials listed in Behr's Verlag GmbH & Co., Hamburg, 1996. Encapsulation is a method well known to those skilled in the art and can be carried out, for example, by using techniques such as spray drying, agglomeration, or extrusion; or by encapsulation of coatings including agglomeration and composite agglomeration techniques.

[0127] Other non-limiting examples of solid carriers include core-shell capsules that use resins of the type of amino plastics, polyamides, polyesters, polyureas, or polyurethanes, or mixtures thereof (all of which are well known to those skilled in the art), which are carried out by using polymerization-initiated phase separation methods, by interfacial polymerization, by techniques such as coagulation, or a combination of these techniques (all of which have been described in the prior art), and optionally in the presence of polymer stabilizers or cationic copolymers.

[0128] Resins can be produced by polycondensation of aldehydes (such as formaldehyde, 2,2-dimethoxyacetaldehyde, glyoxal, glyoxylic acid, or hydroxyacetaldehyde and mixtures thereof) with amines such as urea, benzoguanamine, glycoluryl, melamine, hydroxymethyl melamine, methylated hydroxymethyl melamine, guanidine, etc., and mixtures thereof. Alternatively, pre-formed resins can be used to alkylate polyamines, for example, under trademarks... (Source: Cytec Technology Corp.) (Source: CytecTechnology Corp.) or (Source: BASF) Those that are commercially available.

[0129] Other resins are produced by the formation of trimers of polyols such as glycerol with polyisocyanates such as hexamethylene diisocyanate, isophorone diisocyanate, or phenyl diisocyanate, or biuret of hexamethylene diisocyanate, or trimers of phenyl diisocyanate with trimethylolpropane (as trade name). It is known that the polycondensation of (source: Mitsui Chemicals) produces a trimer of phenyl diisocyanate with trimethylolpropane and a biuret of hexamethylene diisocyanate.

[0130] Some research literature relating to the encapsulation of fragrances via the condensation of melamine resins with aldehydes is represented by articles such as those by K. Dietrich et al., Acta Polymerica, 1989, vol. 40, pages 243, 325, and 683, and 1990, vol. 41, page 91. These articles have described various parameters influencing the preparation of such core-shell microcapsules according to existing methods, which are further detailed and illustrated in patent literature. US 4'396'670 of WigginsTeape Group Limited is a relevant early example of the latter. Since then, many other authors have enriched the literature in this field, and it is impossible to cover all published advancements here, but general knowledge of this type of encapsulation technology is crucial. More recent targeted publications also address suitable uses of such microcapsules, such as those by HYLee et al., Journal of Microencapsulation, 2002, vol. 19, pages 559-569, International Patent Publication WO 01 / 41915, or... The article by Chimia et al., 2011, vol. 65, pages 177-181, is representative.

[0131] The term "fragrance base" refers to a composition containing at least one flavoring ingredient.

[0132] The flavoring agent is not a compound of formulas (I) and (II). Furthermore, by "flavoring agent," it refers herein to a compound used in flavoring preparations or compositions to impart a pleasurable effect. In other words, for a flavoring agent to be considered a flavoring agent, it must be recognized by those skilled in the art as capable of actively or pleasantly imparting or altering the odor of a composition, and not merely possessing an odor.

[0133] The nature and type of flavoring agents present in the base material are not guaranteed to be described in greater detail here, and are inexhaustible in any case. Those skilled in the art can select them based on their common sense and according to the intended use or application and the desired sensory effect. Generally, these flavoring agents belong to different chemical classifications, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenes, nitrogen- or sulfur-containing heterocyclic compounds, and essential oils. The flavoring agents can be of natural or synthetic origin, or even precursor fragrances (i.e., compounds that release flavoring agents upon degradation). Examples of precursor fragrances have been described in the literature, such as A. Herrmann's article in Angewandte Chemie International Edition, 2007, vol. 46, pp. 5836-5863, or more recent similar work, as well as a large body of patent literature in this field.

[0134] In particular, examples of flavoring agents commonly used in fragrance preparations can be listed, such as:

[0135] - Aldehyde components: decanal, dodecanal, 2-methylundecaldehyde, 10-undecenal, octanal and / or nonenal;

[0136] -Aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, menthol and / or α-pinene;

[0137] - Balsam ingredients: coumarin, ethyl vanillin and / or vanillin;

[0138] - Citrus flavoring ingredients: dihydromyrcenol, citral, orange oil, linalool acetate, citronellol, orange terpene, limonene, 1-p-menthene-8-yl acetate and / or 1,4(8)-p-menthide.

[0139] - Floral fragrance components: Methyl dihydrojasmonate, linalool, citronellol, phenethyl alcohol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexylcinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, β-ionone, 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, tricyclodecenyl acetate, geraniol, p-menth-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate Mixtures of 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, methyl jasmonate, 3-methyl-5-phenyl-1-pentanol, tricyclodecenyl propionate, geraniol acetate, tetrahydrolinalool, cis-7-p-menthol, (S)-2-(1,1-dimethylpropoxy)propionate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, pentylcinnamaldehyde, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, tricyclodecenyl isobutyrate, and / or methyl ionone isomers;

[0140] -Fruit flavor components: γ-undecyl lactone, 4-decyl lactone, ethyl 2-methylvalerate, hexyl acetate, ethyl 2-methylbutyrate, γ-nonyl lactone, allyl heptaate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-ethyl acetate and / or diethyl 1,4-cyclohexanedicarboxylate.

[0141] - Green fragrance components: 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styrax acetate, (2-methylbutoxy) allyl acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-octen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one;

[0142] -Musk components: 1,4-dioxa-5,17-cycloheptadecanedione, pentadecenolide, 3-methyl-5-cyclopentadecane-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopentyl[G]isochromene, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl ester, and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl ester;

[0143] -Ingredients of costus root: 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethyl ketone, patchouli oil, terpene fraction 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-cyclopenten-1-yl)-2-buten-1-ol, methyl cypressone, 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-octahydronaphthyl)ethyl-1-ketone and / or isoborneol acetate;

[0144] - Other components (e.g., amber, powdery, spicy, or watery): dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan and any stereoisomers thereof, piperaldehyde, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxane-5-yl)-2-methylpropanal and / or 3-(3-isopropyl-1-phenyl)butanal.

[0145] Specifically, the following floral fragrance additives may be used: methyl dihydrojasmonate, linalool, 3-(4-tert-butylphenyl)-2-methylpropanal, hexylcinnamaldehyde, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, 4-cyclohexyl-2-methyl-2-butanol, high-cis dihydrojasmonate, and tetrahydrolinalool.

[0146] The fragrance base according to the invention may not be limited to the aforementioned flavoring auxiliary ingredients, and many other such auxiliary ingredients are listed in the references in any case, such as S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or later versions thereof, or other works of similar nature, as well as a large number of patent documents in the fragrance industry. It should also be understood that the auxiliary ingredients may also be compounds known to release various types of flavoring compounds in a controlled manner.

[0147] By "fragrance adjuvant," we mean an ingredient that can impart additional benefits such as color, specific lightfastness, chemical stability, etc. A detailed description of the properties and types of adjuvants commonly used in fragrance compositions is impossible to exhaust, but it must be mentioned that the ingredients are well known to those skilled in the art. Specific, non-limiting examples include: viscous agents (e.g., surfactants, thickeners, gelling agents, and / or rheology modifiers), stabilizers (e.g., preservatives, antioxidants, heat / light stabilizers, and / or buffers or chelating agents, such as BHT), colorants (e.g., dyes and / or pigments), preservatives (e.g., antibacterial or antimicrobial or antifungal or antiirritant agents), abrasives, skin coolants, fixatives, insect repellents, ointments, vitamins, and mixtures thereof.

[0148] It is understood that those skilled in the art, by applying standard knowledge in the field and by mixing the above-mentioned components of the fragrance composition through trial and error, are fully capable of designing the optimal formulation for the desired effect.

[0149] In addition to flavoring compositions comprising at least one compound of formula (I), at least one compound of formula (II), at least one flavor carrier, at least one flavor base and optionally at least one flavor adjuvant, compositions of the present invention comprising at least one compound of formula (I), at least one compound of formula (II) and at least one flavor carrier also constitute a specific embodiment of the present invention.

[0150] According to one specific embodiment, the above composition comprises one or more compounds of formula (I) and one or more compounds of formula (II), thereby enabling fragrance manufacturers to prepare blends or fragrances with different aroma notes of the compounds of the present invention, thus creating new tools for their work.

[0151] For clarity, it should also be understood that any mixture obtained directly from chemical synthesis (where the material compounds of the present invention serve as starting materials, intermediates, or end products), for example, without adequately purified reaction media, cannot be considered a flavoring composition according to the present invention, provided that the mixture does not provide the material compounds of the present invention in a suitable form for use in fragrances.

[0152] The material compositions of the present invention can also be advantageously used in all areas of modern fragrances (i.e., fine fragrances or functional fragrances) to actively impart or alter the odor of consumer products to which the material compositions of the present invention are added. Therefore, another object of the present invention is a scented consumer product comprising at least one material composition as a scenting ingredient, the material composition comprising at least one compound of formula (I) and at least one compound of formula (II) as defined above.

[0153] The material composition of the present invention may be added as is or as part of the flavoring composition of the present invention.

[0154] For clarity, "fragrant consumer product" refers to a consumer product intended to deliver at least one pleasant fragrance effect to the surface or space on which it is applied (e.g., skin, hair, fabric, or household surfaces). In other words, a fragrant consumer product according to the invention is a scented consumer product comprising a functional formulation and optional additional beneficial agents corresponding to the desired consumer product, and an olfactory-effective amount of at least one of the substances of the invention. For clarity, the fragrant consumer product is a non-edible product.

[0155] The nature and type of ingredients in flavored consumer products are not guaranteed to be described in more detail here, and in any case, they cannot be exhaustively described. Skilled personnel can select them based on their common sense and the characteristics of the product and the desired effect.

[0156] Non-restricted examples of suitable scented consumer products include perfumes, such as fine perfumes, sprays, or eau de perfumes, colognes, or shaving lotions or aftershaves; fabric care products, such as liquid or solid detergents, fabric softeners, liquid or solid scent enhancers, fabric fresheners, ironing solutions, paper products, bleach, carpet cleaners, and curtain care products; body care products, such as hair care products (e.g., shampoos, colorants or hairsprays, color-changing products, hair styling products, and dental care products), disinfectants, and feminine hygiene products; cosmetic preparations (e.g., skin creams or lotions, cold creams or deodorants or antiperspirants (e.g., sprays or roll-ons), depilatories, tanning agents, sunscreens or after-sun products, and nail products). Skin care products (such as soaps, bath mousses, bath oils or shower gels, or hygiene products or foot / hand care products); air care products, such as air fresheners or "ready-to-use" powder air fresheners, which can be used in home spaces (rooms, refrigerators, cabinets, shoes or cars) and / or public spaces (lobbies, hotels, shopping malls, etc.); or household care products, such as mold removers, furniture care products, wipes, dishwashing liquids or hard surface cleaners (such as floors, bathrooms, sanitary ware or windows); leather care products; car care products, such as polishes, waxes or plastic cleaners.

[0157] Some of the aforementioned scented consumer products may represent corrosive media of the material compositions of the present invention, and therefore may need to be protected from premature decomposition, for example by encapsulation or by chemically binding them to another chemical substance that is suitable for releasing the material compositions of the present invention when subjected to suitable external stimuli, such as enzymes, light, heat or pH changes.

[0158] The composition of the invention can be incorporated into various of the above-described articles or flavoring compositions in a wide range of numerical values. When the composition of the invention is mixed with flavoring agents, solvents or additives commonly used in the art, these values ​​depend on the nature of the article to be flavored and the desired sensory effect, as well as the nature of the auxiliary ingredients in the given base.

[0159] For example, in the case of flavored compositions, the typical concentration of the material composition of the present invention is 0.01 wt%, or even 1 wt%, 15 wt%, or even 25 wt%, or even more, based on the weight of the composition into which it is incorporated. In the case of flavored consumer products, the typical concentration of the material composition of the present invention is 0.01 wt% to 1 wt%, or even 2 wt%, or even more, based on the weight of the consumer product into which it is incorporated.

[0160] When this composition of substances is added to flavored consumer products, concentrations lower than these can be used, for example, 0.01% to 1% by weight, or even 2% by weight, relative to the weight of the product.

[0161] Another object of the present invention is a method for preparing a composition comprising at least one compound of formula (I) and at least one compound of formula (II) as defined above, which can be obtained by hydroformylation of a compound of formula (V). Therefore, another object of the present invention is a method for preparing said composition comprising a hydroformylation step of a compound of formula (V).

[0162]

[0163] It takes the form of any one of its regioisomers or a mixture of these regioisomers; and

[0164] Where R 1 R has the same meaning as described above; relative to position 1, R is an ortho, meta, para substituent of the aromatic ring or a mixture thereof;

[0165] For clarity, the use of the term "hydroformylation" or similar terms refers to the normal meaning understood by those skilled in the art, namely, a reaction carried out in the presence of a metal catalyst and optional ligands, such as rhodium, cobalt, or platinum complexes, preferably rhodium complexes, carbon monoxide, or hydrogen, and ligands such as those containing phosphorus atoms. The hydroformylation of styrene derivatives has been extensively reported in the prior art, particularly regarding the influence of the catalyst and ligands used on the ratio of branched to linear derivatives obtained. Therefore, those skilled in the art will be able to establish optimal conditions to obtain material compositions having the desired amounts of each compound; that is, compounds of formula (I) are branched derivatives, while compounds of formula (II) are linear derivatives. As a non-limiting example, hydroformylation can be carried out under the conditions reported in Applied Organometallic Chemistry 2013 474-478, wherein the method is carried out in the presence of a rhodium complex, particularly [Rh(acac)(CO)2], and a mono- or bidentate phosphite ligand, such as 2,2'-bis((bis(1H-pyrrolo-1-yl)phosphino)oxy)-1,1'-bidinaphthalene, 1,1'-((naphthyl-2-yloxy))phosphadinidyl)bis(1H-pyrrole) or 2,2'-bis((bis(1H-pyrrolo-1-yl)phosphino)oxy)-1,1'-biphenyl. Another non-limiting example of ligands includes (9,9-dimethyl-9H-xanthon-4,5-diyl)bis(diphenylphosphine), 2,2'-bis((di(1H-pyrrolo-1-yl)phosphino)oxy)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bidinaphthalene, 1,1',1”,1”'-(((2,7-di-tert-butyl-9,9-dimethyl-9H-xanthon-4,5-diyl)bis(oxy))bis(phosphinetriyl))tetra(1H-pyrrole), and 4,6-bis(diphenylphosphino)-10H-phenoxazine.

[0166] Phosphorus can be added to the reaction medium of the method of the present invention at a wide range of concentrations. As a non-limiting example, phosphorus concentrations can be listed as about 0.01 mol% to about 50 mol% relative to the substrate; preferably, 0.05 mol% to about 50 mol% relative to the substrate; and preferably, about 0.1 mol% to about 15 mol% relative to the substrate. As those skilled in the art will know, the optimal concentration of the ligand will depend on the properties of the ligand, the properties of the substrate, the properties of the metal complex, the reaction temperature, and the required reaction time.

[0167] Rhodium complexes that can be used in this invention include, but are not limited to, Rh(acac)(CO)2, rhodium trichloride, rhodium nitrate, rhodium acetate, [Rh(OAc)(COD)]2, and Rh4(CO). 12 Rh6(CO) 16The complexes are HRh(CO)(PPh3)3, Rh(C2H4)2(acac), [Rh(Cl)(COD)]2, [Rh(Cl)(COE)2]2, and [Rh(OAc)(CO)2]2, wherein acac represents acetylacetonate, Ac represents acetyl, COD represents 1,5-cyclooctadienyl, COE represents cyclooctenyl, and Ph represents phenyl. The complexes can be added to the reaction medium of the method of the present invention at a wide range of concentrations. As a non-limiting example, complex concentrations of about 0.005 mol% to about 5 mol% relative to the substrate can be listed, preferably 0.01 mol% to about 5 mol%. Preferably, the complex concentration is 0.05 mol% to 2 mol%. It goes without saying that, as those skilled in the art will know, the optimal concentration of the complex will depend on the properties of the latter, the properties of the substrate, the properties of the ligand, the reaction temperature, and the required reaction time.

[0168] According to any of the above embodiments, carbon monoxide and hydrogen can be generated in situ by methods known to those skilled in the art, for example, from methyl formate, formic acid, or formaldehyde. The volume ratio of CO / H2 gas is 2 / 1 to 1 / 5, preferably 1 / 1 to 1 / 5, or preferably 2 / 1 to 1 / 2, more preferably 1.5 / 1 to 1 / 1.5, and more preferably, the volume ratio is 1 / 1.

[0169] According to any of the above embodiments, relative to position 1, the R group of the compound of formula (V) can be an ortho, meta, or para substituent of the aromatic ring; that is, the compound of formula (V) can be formula (V'), (V”), or (V”'). Preferably, the compound of formula (V) conforms to compound (V”').

[0170]

[0171] According to any of the above embodiments, the compound of formula (V) can be in the form of a composition of substances comprising a mixture of regioisomers; that is, a mixture comprising a compound (compound of formula (V')) in which the R group is ortho-substituent relative to position 1, a compound (compound of formula (V')) in which the R group is meta-substituent relative to position 1, and a compound (compound of formula (V'')) in which the R group is para-substituent relative to position 1.

[0172] Preferably, the material composition comprises at least one compound relative to position 1, wherein the R group is a para-substituent.

[0173] Preferably, the mixture contains

[0174] - Up to 40 wt% of compound of formula (V');

[0175] - Up to 50 wt% of the compound of formula (V”); and

[0176] - At least 50 wt% of the compound of formula (V”').

[0177] Even more preferably, the mixture contains

[0178] - Up to 20 wt% of compound of formula (V');

[0179] - Up to 10 wt% of the compound of formula (V”); and

[0180] - At least 70 wt% of the compound of formula (V”').

[0181] Even more preferably, the mixture contains

[0182] - Up to 5 wt% of compound of formula (V');

[0183] - Up to 5 wt% of the compound of formula (V”); and

[0184] - At least 90 wt% of the compound of formula (V”').

[0185] Even more preferably, the mixture contains

[0186] - Up to 2 wt% of compound of formula (V');

[0187] - Up to 3 wt% of the compound of formula (V”); and

[0188] - At least 95 wt% of the compound of formula (V”').

[0189] According to a preferred embodiment, the R group of the compound of formula (V) relative to position 1 is a meta- and / or para-substituent of the aromatic ring; that is, the compound of formula (V) can be formula (V”) and / or (V”’). Preferably, the R group of the compound of formula (V) relative to position 1 is a para-substituent of the aromatic ring; that is, the compound of formula (V) conforms to formula (V”’).

[0190] According to any of the above embodiments, the compound of formula (V) conforms to the compound of formula (VI).

[0191]

[0192] Where R 1 It has the same meaning as above.

[0193] According to any of the above embodiments, the compound of formula (V) can be prepared according to methods reported in the literature or standard methods known in the art; for example, by adding a Grignard reagent obtained from commercially available chloromethylvinylbenzene to acetone.

[0194] The reaction can be carried out in the presence or absence of a solvent. Any solvent current of this type of reaction may be used for the purposes of this invention when a solvent is required or used for practical reasons. Non-limiting examples include C. 6-12 Aromatic solvents, such as toluene, 1,3-diisopropylbenzene, isopropylbenzene, or pseudocumene, or mixtures thereof; ethyl acetate or ether solvents, such as methyltetrahydrofuran, tetrahydrofuran, or mixtures thereof. The choice of solvent is a function of the substrate and / or catalyst properties, and those skilled in the art are able to select the most suitable solvent in each case to optimize the reaction.

[0195] The hydroformylation reaction can be carried out in a temperature range of 50°C to 150°C, more preferably in a temperature range of 80°C to 130°C, or even in a temperature range of 90°C to 110°C. Of course, those skilled in the art can also select the preferred temperature based on the melting and boiling points of the starting and final products and the required reaction or conversion time.

[0196] The reaction can be carried out at a CO / H2 pressure of 1 bar to 50 bar, preferably in the range of 5 bar to 20 bar, and more preferably in the range of 5 bar to 15 bar. Of course, those skilled in the art can adjust the pressure according to the catalyst loading and the dilution of the substrate in the solvent.

[0197] It should be understood that the material compositions of the present invention may contain various regioisomers, such as ortho, para, or meta products, depending on the quality of the starting material used; that is, depending on whether (V'), (V”), (V”’) or a mixture thereof are used.

[0198] Another aspect of the present invention relates to the intermediate product of formula (V).

[0199]

[0200] It takes the form of any one of its regioisomers or a mixture of these regioisomers; and

[0201] Where R 1 Represents a hydrogen atom or C 1-2 Alkyl; and R represents a group of the formula -CH2C(Me)2OH; relative to position 1, said R is an ortho, meta, para substituent of an aromatic ring or a mixture thereof.

[0202] Example

[0203] The invention will now be described in further detail through the following embodiments, wherein abbreviations have their usual meanings in the art, and temperature is expressed in degrees Celsius (°C); for 1 H and 13C. NMR spectral data were recorded in CDCl3 using a 400 or 500 MHz instrument (unless otherwise specified), with chemical shift δ expressed in ppm relative to TMS as the standard, and coupling constant J expressed in Hz.

[0204] Example 1

[0205] Synthetic composition of the present invention

[0206] a) Preparation of 2-methyl-1-(4-vinylphenyl)prop-2-ol

[0207] A solution of 1-(chloromethyl)-4-vinylbenzene (5.06 g, 33 mmol) in 2-methyltetrahydrofuran (47 g) was added at 40 °C to a solution of Mg (0.84 g, 34.6 mmol) in 2-methyltetrahydrofuran (3 g) to form a Grignard reagent. The reaction mixture was cooled to 0 °C and anhydrous acetone (2.88 g, 49.6 mmol) was added over 1 hour. The reaction mixture was quenched with NH4Cl (25 g, 30% aqueous solution), and the phases were separated. The organic phase was washed with water (3x) and evaporated to give crude 2-methyl-1-(4-vinylphenyl)prop-2-ol (5.38 g), which was purified by distillation (3.8 g, 65% yield).

[0208] 1 H NMR (500MHz, CDCl3): δ=7.37-7.33(m,2H),7.18-7.14(m,2H),6.69(dd,J=11,18Hz,1 H),5.74-5.70(m,1H),5.23-5.19(m,1H),2.74(s,2H),1.54(br,1H),1.21(s,6H)ppm. 13 C NMR (125MHz, CDCl3): δ=137.5(s), 136.6(d), 135.8(s), 130.6(d), 126(s), 113.4(t), 70.8(s), 49.5(t), 29.2(q)ppm.

[0209] b) Catalyzing the hydroformylation of 2-methyl-1-(4-vinylphenyl)prop-2-ol using an in-situ generated rhodium complex:

[0210] A typical experimental procedure is as follows:

[0211] Under argon atmosphere, 2-methyl-1-(4-vinylphenyl)prop-2-ol (1.76 g, 10 mmol), the ligand from Table 1 (13.8 mg, 0.024 mmol, 0.24 mol%), a toluene solution of Rh(CO)2 (acac) (1 ml, 0.01 M, 0.01 mmol, 0.1 mol%), and toluene (11 ml) were added sequentially to a 60 ml s / s autoclave. The autoclave was closed and purged with a mixed gas (H2 / CO, 1 / 1) at 10 bar and pressurized. The solution was stirred and heated at 100 °C for 16 hours to obtain a mixture of 3-(4-(2-hydroxy-2-methylpropyl)phenyl)propanal as a straight-chain aldehyde and 2-(4-(2-hydroxy-2-methylpropyl)phenyl)propanal as a branched-chain aldehyde.

[0212] Under these conditions, several phosphorus-containing ligands reported in Table 1 were tested. The results are reported in Table 2.

[0213] Table 1 The structure and name of the diphosphine used.

[0214]

[0215]

[0216] Table 2 Hydroformylation of 2-methyl-1-(4-vinylphenyl)prop-2-ol using in-situ generated complex Rh(H)(CO)2(L1-L6)

[0217] experiment ligands Conv. Lin. Bran. Sat. 1 L1 100 48.6 51.1 0.3 <![CDATA[2 [a] ]]> <![CDATA[L2 [b] ]]> 100 <![CDATA[68.8 [c] ]]> <![CDATA[29.4 [c] ]]> 0.3 3 L3 100 66.6 33 0.4 4 <![CDATA[L4 [d] ]]> 100 80.1 19.3 0.6 <![CDATA[5 [e] ]]> <![CDATA[L4 [d] ]]> <![CDATA[100 [f] ]]> <![CDATA[75.5 [g] ]]> <![CDATA[22.8 [g] ]]> 0.3 <![CDATA[6 [h] ]]> <![CDATA[L5 [b] ]]> 100 <![CDATA[81.5 [i] ]]> <![CDATA[16.2 [i] ]]> 0.4

[0218] Conv.: Conversion rate (in %) from styrene feedstock to the corresponding total aldehydes after 16 hours, analyzed by GC. Reaction conditions: H2 / CO (10 bar), 100 °C, toluene (1 M).

[0219] Lin.: Amount of 3-(4-(2-hydroxy-2-methylpropyl)phenyl)propanal (linear aldehyde) as measured by GC (DB-1), in percentage.

[0220] Bran.: Amount of 3-(4-(2-hydroxy-2-methylpropyl)phenyl)propanal (branched aldehyde) as measured by GC (DB-1), in percentage.

[0221] Sat.: The amount of 1-(4-ethylphenyl)-2-methylprop-2-ol (saturated feedstock) as measured by GC (DB-1), in percentage.

[0222] [a] The starting styrene material is a mixture of the para isomer (98.3%) and the meta isomer (1.7%).

[0223] [b] The ligand content is 0.5 mol%.

[0224] [c] Meta-linear and branched isomers were also present by GC: 1.1% and 0.4% respectively (i.e., 3-[3-(2-hydroxy-2-methylpropyl)phenyl]propanal and 2-[3-(2-hydroxy-2-methylpropyl)phenyl]propanal).

[0225] [d] Use R-enantiomers.

[0226] [e] The starting styrene material is a mixture of the para isomer (97.9%), meta isomer (1.6%), and ortho isomer (0.5%).

[0227] [f] The reaction was carried out at 20 bar under H2 / CO(1 / 1)20 bar.

[0228] [g] Meta-linear and branched isomers were also found via GC: 1.2% and 0.2%, respectively.

[0229] [h] The starting styrene material is a mixture of the para isomer (97.6%) and the meta isomer (2.1%).

[0230] [i] Meta-linear and branched isomers were also found via GC: 1.6% and 0.3%, respectively.

[0231] Example 2

[0232] Synthetic composition of the present invention

[0233] Under argon atmosphere, 2-methyl-1-(4-vinylphenyl)prop-2-ol (15.04 g, 85 mmol, 98.3% GC) containing the meta isomer (1.7% by GC), R-L4 (12.6 mg, 0.021 mmol, 0.024 mol%), a toluene solution of Rh(CO)2(acac) (1 ml, 0.0079 M, 0.0079 mmol, 0.0093 mol), and toluene (27 ml) were added sequentially to a 100 ml s / s autoclave. The synthesis gas (H2 / CO, 1 / 1) was sealed, purged, and pressurized in an autoclave at 20 bar. The solution was stirred and heated at 100°C for 16 hours to obtain a mixture of 3-(4-(2-hydroxy-2-methylpropyl)phenyl)propanal (74.5% by GC), 3-(3-(2-hydroxy-2-methylpropyl)phenyl)propanal (1.3% by GC), 2-(4-(2-hydroxy-2-methylpropyl)phenyl)propanal (21.4% by GC), 2-(3-(2-hydroxy-2-methylpropyl)phenyl)propanal (0.3% by GC), 2-methyl-1-(4-vinylphenyl)prop-2-ol (0.6% by GC), and 1-(4-ethylphenyl)-2-methylprop-2-ol (0.6% by GC). Vacuum concentration and short-path distillation (boiling point: 130 °C / 0.2 mbar) yielded a mixture of straight-chain and branched aldehydes (15.81 g, 77 mmol, 90% yield) having the following composition: (3-(4-(2-hydroxy-2-methylpropyl)phenyl)propanal (75.2% by GC), 3-(3-(2-hydroxy-2-methylpropyl)phenyl)propanal (1.3% by GC), 2-(4-(2-hydroxy-2-methylpropyl)phenyl)propanal (22.2% by GC), 2-(3-(2-hydroxy-2-methylpropyl)phenyl)propanal (0.4% by GC), 2-methyl-1-(4-vinylphenyl)prop-2-ol (0.4% by GC), and 1-(4-ethylphenyl)-2-methylprop-2-ol (0.5% by GC).

[0234] Example 3

[0235] Preparation of Fragrance Composition

[0236] Women's perfumes are made by mixing the following ingredients:

[0237]

[0238]

[0239] *In dipropylene glycol

[0240] Adding 800 parts by weight of the composition of the present invention obtained in Example 3 to the above composition, replacing 800 parts by weight of dipropylene glycol, imparts freshness and roundness to the composition, while also giving it a floral-lily-of-the-valley fragrance with a moistening effect. The composition of the present invention is particularly harmonious with the ozone, watery, and salicylic acid notes of the composition. The effect of adding the composition of the present invention to the above composition is very close to that of adding... Rather than the effects provided by the material composition of the present invention.

[0241] Example 4

[0242] Preparation of Fragrance Composition

[0243] Men's fragrances are made by mixing the following ingredients:

[0244]

[0245]

[0246] *In dipropylene glycol

[0247] Adding 800 parts by weight of the composition of the present invention obtained in Example 4 to the above composition, replacing 800 parts by weight of dipropylene glycol, imparts freshness and roundness to the composition, while also giving it a floral-lily-of-the-valley fragrance with a moist effect. The composition of the present invention is particularly harmonious with the ozone, water, salicylic acid, and oakmoss notes of the composition. The effect of adding the composition of the present invention to the above composition is very close to that of adding... Rather than the effects provided by the material composition of the present invention.

[0248] Example 5

[0249] Preparation of perfumes comprising the compositions of the present invention

[0250] A perfume is prepared by adding 5 to 15% by weight of the composition of the present invention from Example 3 or 4 relative to the total weight of the perfume to ethanol under gentle shaking.

Claims

1. A composition comprising a mixture of regioisomers of a compound of formula (V), Where R 1 Represents a hydrogen atom or C 1-2 Alkyl; and R represents a group with the formula -CH2C(Me)2OH; The mixture contains: Relative to position 1, R is a compound with a meta-substituent on an aromatic ring, and Relative to position 1, R is a compound with a para-substituent on an aromatic ring.

2. The composition of claim 1, wherein the mixture comprises a compound of formula (VI), Where R 1 It represents a hydrogen atom.

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