Flavor composition

Abstract

( S, E ) -10-hydroxy-4,8-dimethyldec-4-enal and its use in perfumery.​

Description

[0001] Invention Field

[0002] This invention generally relates to novel compounds, fragrance compositions containing them, and their use in fragrances. Background of the Invention

[0004] Compounds with floral scents, especially those reminiscent of lily of the valley, are highly favored as fragrance ingredients. They are important in floral bases and can act as harmonizers in many types of fragrance creation. This type of compound is widely used in home care, laundry care, and personal care products, as well as in fine fragrances, to produce pleasant scents or mask unpleasant odors.

[0005] The literature describes 4,8-dimethyl-10-hydroxy-4-decenal (in the form of a racemic mixture) and its use in fragrance and flavor creation. Specifically, the racemic mixture is disclosed in JPS52-91815A, which is described as having a sweet, hazelnut-like odor. WO2021108472 also proposes that the racemic mixture can be used in combination with a buffer in fragrance compositions. WO2021 / 167054 discloses a fragrance formulation containing the racemic mixture. However, to the applicant's knowledge, the racemic mixture is not commercially available.

[0006] Despite the prior art disclosed as described above and the availability of many other iconic lily-of-the-valley scent molecules, consumer product manufacturers are constantly seeking new scent ingredients or new forms of scent ingredients that can create, improve or enhance the lily-of-the-valley scent character and can be easily incorporated into floral bases to serve as a blending agent in many types of fragrance creation in a more sustainable and cost-effective manner.

[0007] New ingredients or forms are favored not only for their own qualities, but also as milder, floral alternatives to iconic lily aldehydes (such as neolily aldehyde and lily aldehyde), or as alternatives to other valuable lily aldehydes that may not enjoy widespread use due to their lack of biodegradability or cost-effectiveness in application.

[0008] There is still a need for new flavoring ingredients or new forms of flavoring ingredients that can impart lily of the valley characteristics to consumer products and are biodegradable and cost-effective in use. Invention Overview

[0010] In addressing the deficiencies in the prior art, the applicant has surprisingly discovered that a particular enantiomer of 4,8-dimethyl-10-hydroxy-4-decenal is a particularly potent fragrance ingredient, exhibiting a strong lily-of-the-valley aroma without the oily odor sometimes associated with typical lily-of-the-valley flavorings. The applicant has further surprisingly discovered that this enantiomer not only exhibits a pleasant odor but is also both biodegradable and highly effective compared to other common lily-of-the-valley flavorings, and especially compared to its enantiomers.

[0011] In a first aspect of the invention, a method according to formula (I) is provided. S,E 10-Hydroxy-4,8-Dimethyldec-4-enal

[0012] .

[0013] In a second aspect of the invention, a method for preparing a compound according to formula (I) is provided.

[0014] In a third aspect of the invention, a fragrance composition is provided comprising a compound of formula (I) and at least one other fragrance ingredient.

[0015] In a fourth aspect of the invention, the use of compounds according to the first aspect of the invention is provided for imparting, enhancing or improving a pleasant odor impression, or for masking, reducing or eliminating an unpleasant odor impression.

[0016] In a fifth aspect of the invention, a consumer product is provided comprising a compound according to a first aspect of the invention.

[0017] Details, examples, and preferred embodiments provided with respect to any one or more of the aspects described herein will be further described herein and equally apply to all aspects of the invention. Unless otherwise stated herein or unless obviously contradicted by the context, the invention includes any combination of the embodiments, examples, and preferred embodiments described below with all possible variations thereof. Invention Details

[0019] The first aspect of the invention relates to enantiomers ( S,E 10-Hydroxy-4,8-dimethyldecyl-4-enal, also referred to herein as compound (I). To the best of the applicant's knowledge, the preparation and characterization of this enantiomer and its use in fragrances have not been described in the literature.

[0020] The compound of formula (I) was found to possess unpredictable and favorable odor properties. Sensory evaluation by a trained panel revealed that the enantiomer could be generally described as floral, lily-of-the-valley flavoring, with more distinct odor layers that could be described as very pleasant rose, aldehyde, and metallic notes. In this respect, the compound of formula (I) was assessed as having a more pleasant odor than its R,E enantiomers, which the panel described as having a hot iron odor, a sharpness, and only a faint floral note. The hot iron odor and sharpness were also found to be characteristic of racemic mixtures.

[0021] It has been found that the compound of formula (I) has the aroma notes of lily aldehyde and a pleasant aroma profile. It was unexpectedly discovered that the compound of formula (I) is much more potent than its (R,E)-10-hydroxy-4,8-dimethyldecyl-4-enal enantiomer.

[0022] Its odor potency compared to its R,E enantiomers was discovered by measuring its EC50 value using a novel olfactory receptor assay (related to human perception of lily of the valley-type flavoring agents). This test is described in more detail in the examples below.

[0023] The potency of the compounds of formula (I) compared to their R,E enantiomers is significant and of particular interest to perfumers for reasons related to sustainability and economy, especially considering that the compounds of formula (I) can be prepared by cost-effective synthesis as described in more detail below.

[0024] Furthermore, compounds of formula (I) were found to be biodegradable. Adding biodegradable components to perfumers' palettes (which have broad applicability in floral bases) is particularly important for the fragrance industry. Specifically, compounds of formula (I) exhibit potential for use as certain popular lily-of-the-valley aldehydes (e.g., 4-(octahydro-4,7-methylene-5Hinden-5-ylidene)butyraldehyde, available under the trade name Dobe Carr). ® Biodegradable alternatives.

[0025] In the context of this invention, a compound of formula (I) is considered biodegradable if it meets the pass criteria according to the OECD manotropic respiration method (especially the OECD 301F method, which is well known in the art). In this method, the pass level at which a compound is considered "easily biodegradable" or "easily biodegradable" is 60% of the pyrochemical oxygen demand (BOD) and / or chemical oxygen demand (COD). This pass value must be achieved within a 10-day window during a 28-day testing period. The 10-day window begins when the degree of biodegradation has reached 10% of the pyrochemical oxygen demand and / or COD and must end before day 28 of the test. Preferred methods for performing OECD method 301F are provided below.

[0026] If the test for biodegradability is positive, it can be assumed that the compound will undergo rapid and complete biodegradation in the environment (Introduction to the OECD 25 Guidelines for the Testing of Chemicals, Section 3, Part 1: Principles and Strategies Related to the Testing of Degradation of Organic Chemicals; Officially adopted: July 2003).

[0027] "Inherently biodegradable" can also be assessed using OECD Method 301F, although a different pass criterion is used. More specifically, the pass criterion is 60% of the theoretical oxygen demand and / or chemical oxygen demand. This pass value can be reached after a 28-day testing period, which is typically extended to 60 days. A 10-day window is not applied.

[0028] Due to their elegant floral scent, fresh and natural qualities, and high potency, compounds of formula (I) can be used in relatively high concentrations, especially in floral fragrance compositions, as harmonizers in many olfactory-oriented aspects of fragrance creation. Compounds of formula (I) are particularly useful for any perfumer intending to create fragrance compositions containing high levels of biodegradable ingredients.

[0029] A second aspect of the invention relates to a method for preparing a compound of formula (I).

[0030] In embodiments of the invention, compounds of formula (I) can be prepared according to a method similar to that described in WO2021 / 108472, which is incorporated herein by reference and shown as “Path A” in Figure 1. This synthetic route is also described in more detail in the examples below.

[0031] In another embodiment of the invention, the readily available starting material (S,E)-dihydrofarnesol (CAS 27745-36-4; Biocyclamol) can be used. TM Compounds of formula (I) were prepared by selective oxidative cleavage of the distal double bond of the compound. This route is shown as "Path B" in Figure 1.

[0032] The compound of formula (I) can be used as a flavoring ingredient in a flavoring composition that forms the third aspect of the invention.

[0033] The fragrance composition according to the invention comprises a compound of formula (I) and at least one other fragrance ingredient and / or an adjuvant commonly used in fragrances.

[0034] In a specific embodiment of the present invention, the fragrance composition comprises 4,8-dimethyl-10-hydroxy-4-decenal, which is enantiomerically enriched with compounds of formula (I).

[0035] In a more specific embodiment of the invention, when the fragrance composition contains 4,8-dimethyl-10-hydroxy-4-decenal, which is enantiomerically enriched with a compound of formula (I), the compound of formula (I) is present in an enantiomeric excess (ee) of at least 60%, more particularly at least 75%, still more particularly at least 90%, and even more particularly at least 95%.

[0036] In a specific embodiment of the invention, the fragrance composition comprises a compound of formula (I) in its enantiomeric pure form (i.e., 100% ee).

[0037] In relevant embodiments of the present invention, when the fragrance composition contains 4,8-dimethyl-10-hydroxy-4-decenal, which is an enantiomerically enriched mixture of compounds of formula (I), the mixture may be a product of enantioselective synthesis, the result of chiral separation, or it may be obtained by physically mixing a mixture of isomers of a compound of formula (I) with 4,8-dimethyl-10-hydroxy-4-decenal (e.g., racemic mixtures).

[0038] In a specific embodiment of the present invention, the flavoring composition may comprise a compound of formula (I) and its structural isomer ( S,Z A mixture of 10-hydroxy-4,8-dimethyldecyl-4-enal. In a more specific embodiment, the S,Z isomers are present in relatively small amounts, i.e., the weight ratio of S,E to S,Z is at least 90:10, and more particularly 99:1. In another specific or preferred embodiment, the ratio of S,E to S,Z is at least 70:30, more preferably 75:25.

[0039] The fragrance compositions according to the invention may contain one or more fragrance ingredients commonly used in fragrances. These fragrance ingredients may include any fragrance oils, alcohols, aldehydes, ketones, ethers, acetals, esters, lactones, macrocyclic compounds, and heterocyclic compounds commonly used in fragrances, as well as any excipients or auxiliaries commonly used in combination with such fragrance ingredients, such as solvents, diluents, and other auxiliaries commonly used in the art (e.g., preservatives, etc.). Such fragrance ingredients are described in standard fragrance textbooks and references, such as "Perfume and Flavour Chemicals," S. Arctander, Allured Publishing Corporation, 1994, IL, USA, and subsequent editions, which are incorporated herein by reference.

[0040] As an adjuvant or excipient that can be used in the fragrance compositions according to the invention, reference can be made to any of the conventional ingredients used in fragrance compositions for reasons other than or not particularly related to their odor characteristics. For example, an adjuvant or excipient can be an ingredient that acts as an aid in processing one or more fragrance components or a fragrance composition containing said one or more components, or that can improve the handling or storage of the fragrance components or a fragrance composition containing said fragrance components. It can also be an ingredient that provides additional benefits (e.g., imparting color or texture). It can also be an ingredient that imparts lightfastness or chemical stability to the fragrance components or one or more components contained in a fragrance composition containing said fragrance components. The nature and type of such materials that can be used in fragrance compositions containing them cannot be described exhaustively, but it must be mentioned that such ingredients are well known to those skilled in the art. Examples include solvents and co-solvents; surfactants and emulsifiers; viscosity and rheology modifiers; thickeners and gelling agents; preservatives; pigments, dyes, and coloring substances; extenders, fillers, and reinforcing agents; stabilizers, fillers, acidifiers, buffers, and antioxidants that resist the adverse effects of heat and light.

[0041] If a specific fragrance or functional effect is desired (e.g., altering the spatial-temporal odor characteristics of a fragrance composition), any one or more fragrance components, adjuvants, or excipients used in the fragrance compositions according to the invention can be formulated in a delivery carrier. The delivery carrier may comprise microcapsules or other solid supports to which one or more fragrance components or adjuvants may be chemically or physically bound. Furthermore, one or more fragrance components or adjuvants may be dissolved or dispersed in a matrix material for controlling the rate at which the one or more components are released. In another alternative embodiment, one or more components or adjuvants may be supported on a porous matrix, such as cyclodextrin or zeolite or other inorganic materials. In a further embodiment, one or more fragrance components may be provided in the form of a so-called pro-perfume or fragrance precursor, which may be activated under specific conditions (e.g., moisture, heat, or light) to release the fragrance components in a controlled manner. In view of the foregoing, it will be understood that fragrance compositions can be at least partially in solid, gel, foam, and / or liquid form. If present in solid form, it may be in granule, powder, or tablet form.

[0042] As stated herein, compounds according to formula (I) are particularly useful, at least in part, because of their biodegradability. They can be used in fragrance compositions for their pleasantness and to increase the percentage of biodegradable components in such compositions, or they can be used in combination with other biodegradable fragrance ingredients to form fully biodegradable fragrance compositions. Furthermore, consumer products containing compounds or fragrance compositions of the present invention can therefore be considered to be composed partly or entirely of biodegradable materials.

[0043] According to a fourth aspect of the invention, compounds of formula (I) and fragrance compositions containing them can be used in fragrances, and in particular for imparting, enhancing or improving pleasant odor impressions or masking, reducing or eliminating unpleasant odor impressions.

[0044] Unpleasant odors that need to be reduced or eliminated may emanate from consumer products in which compounds or fragrance compositions are incorporated, or from parts of consumer products intended to be applied thereto treat odors (e.g., human or animal bodies or inanimate surfaces).

[0045] The compounds of formula (I) can be used in fragrances and in fragrance compositions of the present invention in a wide range of amounts, depending on the specific olfactory effect desired by a skilled perfumer. Due to their high impact, they can be used in small amounts to achieve olfactory effects economically. Alternatively, due to their fresh, diffuse, transparent, and easily harmonized pleasantness, they can be used in relatively large quantities as a harmonizing agent in fragrance compositions in various olfactory orientations. Generally, the compounds of formula (I) can be used in a wide range of amounts, ranging from 0.0001 to 90 wt% of the fragrance composition, preferably from 0.001 to 50 wt%, more preferably from 0.01 to 20 wt%, and most preferably from 0.1 to 10 wt%.

[0046] Compounds of formula (I) exhibit similarity to other known lily aldehydes (e.g., neolily aldehyde). ® Or Dobby Carl ® Similar odor characteristics. Therefore, compounds of formula (I) can be used in fragrance compositions as substitutes for certain lily aldehydes (such as these compounds).

[0047] Therefore, compounds of formula (I) are used to impart a lily-of-the-valley scent to fragrance compositions, or to act as another lily-of-the-valley aldehyde fragrance component (e.g., neolily-of-the-valley aldehyde). ® Or Dobby Carl ® The use of alternatives to lily aldehydes, and the fact that they do not contain or are substantially free of the aforementioned lily aldehydes (e.g., neolily aldehyde). ® Or Dobby Carl ® The fragrance composition containing a compound of formula (I) represents another embodiment of the present invention.

[0048] As used herein, the term "substantially free of" means if the aforementioned lily aldehyde (e.g., neolily aldehyde) is present in the fragrance composition. ® Or Dobby Carl ® If present in trace amounts, it is below the levels consistent with its regular use in fragrances, as practiced by skilled perfumers. More specifically, it is present in less than 0.1 wt% based on the total weight of the fragrance composition.

[0049] Whether the compound of formula (I) is used in a fragrance composition as a substitute for another lily aldehyde, or whether it is used in its own way to produce a pleasant effect, a skilled perfumer may consider it appropriate to combine other complementary fragrance ingredients with the compound of formula (I) to balance or fine-tune its odor characteristics and the odor characteristics of the fragrance composition containing it.

[0050] Therefore, in a specific embodiment of the present invention, the fragrance composition comprises a fragrance composition containing a compound according to formula (I) and optionally mixed with one or more of the following ingredients: 2-cyclohexylene-2-phenylacetonitrile, such as paeononitrile. TM (9-Hydroxy-5,9-Dimethyl-4-decenal) MAHONIAL TM And 4-methyl-2-(2-methylpropyl)tetrahydro-2H-pyran-4-ol, such as lily of the valley pyran TM ; and methyl 2-(2-hexyl-3-oxocyclopentyl)acetate, such as methyl dihydrojasmonic acid. TM .

[0051] The flavoring compositions described herein are not necessarily limited to these selected ingredients. Flavoring compositions may contain one or more additional flavoring ingredients that are particularly harmonious when combined with compounds of formula (I).

[0052] Specific fragrance ingredients that can be used harmoniously with compounds of formula (I) include, but are not limited to:

[0053] Natural ingredients, such as those selected from iris, mimosa, ylang-ylang, bergamot, jasmine, and rose;

[0054] Synthetic lily of the valley fragrance components, such as citronellal (103-95-7), hydroxycitronellal (107-75-5), hydroxycitronellal diethyl acetal (7779-94-4), silver aldehyde (6658-48-6), berberine aldehyde (18127-01-0), anthocyanin (125109-85-5), and cyclolily of the valley aldehyde (7775-00-0); and Doubikal (30168-23-1).

[0055] Rose-type floral components, such as ethyl phenyl alcohol (60-12-8), dimethyl phenylethyl alcohol (103-05-9), citronellol (106-22-9), rose alcohol (106-22-9), Acet. DMBC (151-05-3), geraniol (106-24-1), nerol (106-25-2), nerol (7212-44-4), rose alcohol (55066-48-3), o-methylphenylethanol (19819-98-8), citronellol isobutyrate (97-89-2), and meropenemol (103694-68-4);

[0056] Freesia-type floral components, such as linalool (78-70-6), Rossitol (215231-33-7), and corollol (83926-73-2);

[0057] Lilac-type floral components, such as Ale. cinnamyl alcohol (104-54-1), propyl phenylalcohol (122-97-4), and terpineol (8000-41-7);

[0058] Jasmine-type floral components, such as benzyl acetate (140-11-4), methyl dihydrojasmonate (24851-98-7), hexylcinnamaldehyde (101-86-0) and pentylcinnamaldehyde (122-40-7);

[0059] Lily-of-the-valley floral fragrance components, such as Super Muguet (26330-65-4), hydroxycitronellol dimethyl acetate (141-92-4), and magnolol (92046-49-6).

[0060] Mugetanol (63767-86-2), Mugesia (56836-93-2), indole (120-72-9) and indoleene liquid (67860-00-8);

[0061] The aromatic components include, for example, cis-3-hexenol (928-96-1), phenylacetaldehyde (122-78-1), marsé aldehyde (67845-30-1), cis-3-hexenyl acetate (3681-71-8), acetal CD (29895-73-6), precarone (74499-58-4), mevlanal (55066-49-4), elintal (40910-49-4), gliclazide dioxane (68901-32-6), and arbutinol (83926-73-2);

[0062] Refreshing ingredients, such as C11 undecenal (112-45-8), C11 undecenal (112-44-7), C10 aldehyde (112-31-2), C12 MNA aldehyde (110-41-8), neojasmine aldehyde (1205-17-0), citral (5392-40-5), Oxyde de Limette (73018-51-6), anthocyanin (125109-85-5), fenestration aldehyde (67634-15-5), dihydrofarnesal (51513-58-7), dihydrofarnesol (51411-24-6), adolphin aldehyde (141-13-9), and citronellyl aldehyde. Oxyacetaldehyde (7492-67-3), Super Lily Aldehyde (71077-31-1), and Dodecenoaldehyde (4826-62-4);

[0063] Woody components, such as ionone (8013-90-9) and methyl ionone (1335-46-2);

[0064] Powdered fragrance components, such as tuna musk (21145-77-7), Tibetan musk (106-02-5), jasmine aldehyde (120-57-0) and vanillin (121-33-5);

[0065] Various harmonious floral components, such as hydroxycitronellol (Phixia) (107-75-5), farnesyl aldehyde (19317-11-4), farnesyle acetate (29548-30-9), rose acetate (141-11-7), cyclomethylene citronellol (15760-18-6), lily of the valley alcohol (5502-75-0), citric acid acetate (72403-67-9), and methoxydihydrocitronellol (Melonia) (3613-30-7), wherein the CAS numbers of the molecules are provided in parentheses; and any mixtures thereof.

[0066] The particularly preferred fragrance composition according to the invention contains a compound according to formula (I) and one or more fragrance ingredients selected from the following: methyl dihydrojasmonate, ambroxanone, linalool, ambroxan, galena, cis-3-hexenol, citronellol, vanillin, linalyl acetate, ethylene brassinate, neojasmaldehyde, coumarin, dihydromyrcenol, ethyl linalool, benzyl acetate, pyruvaldehyde, and phenethyl alcohol.

[0067] More particularly preferably, when the compound of formula (I) is used as lily aldehyde (e.g., neolily aldehyde) ® Or Dobby Carl ®When choosing a substitute for ), the preferred fragrance composition is one that is immediately described above and contains no or substantially no lily aldehyde to be substituted.

[0068] The fifth aspect of the invention relates to consumer products comprising compounds of formula (I) or fragrance compositions containing compounds of formula (I) as described herein.

[0069] Based on the total weight of the consumer product, the compound of formula (I) may be present in the consumer product in an amount from about 0.0001 wt% to about 30 wt%. However, these values ​​are given only as examples, as experienced perfumers may also use lower or higher concentrations to achieve the desired effect or create new fragrances.

[0070] Consumer products can be personal care products, such as fragrance extracts, perfumes, toilettes, aftershaves, colognes, pre-shaving products, spray colognes, scented cleansing wipes, body care products, soaps, liquid shower gels, hair care products (e.g., shampoos, conditioners), deodorants, antiperspirants, hand creams and lotions, foot creams and lotions, hair removal creams and lotions, aftershave creams and lotions, tanning creams and lotions, and decorative beauty products (e.g., cosmetics).

[0071] Consumer products can be cleaning products, such as acidic, alkaline and neutral detergents, fabric fresheners, ironing aids, liquid detergents, fabric softeners, laundry soaps, laundry sheets, disinfectants (e.g., surface disinfectants), air fresheners, aerosol sprays, waxes and polishes.

[0072] Consumer products can be household items, such as candles, lamp oil, incense, insecticides, repellents, and propellants.

[0073] Consumer products can be household care products, such as textile treatment products, ironing aids, cleaning cloths, laundry detergents, cleaning products (especially for hard and / or soft surfaces), household cleaners, care products, laundry care products, laundry care products, room fragrances and air fresheners, conditioning agents, colorants, fabric conditioning agents, conditioning bases, pharmaceuticals, crop protection products, polishing agents, food, beauty products, fertilizers, building materials, adhesives, bleaching agents, decalcifying agents, floor care products, cookware care products, leather care products or furniture care products, scrubbing agents, disinfectants, fragrances, mold removers and / or precursors of the above products.

[0074] Consumer products can be cleaning products, for example:

[0075] Toilet cleaners or washroom cleaners, in other words, products for cleaning washbasins and urinals, are preferably provided in the form of powder, blocks, tablets, or liquids, and preferably gels. In addition to other typical ingredients (e.g., surfactants), they typically include organic acids (e.g., citric acid and / or lactic acid) or sodium bisulfate, sulfamic acid, or phosphoric acid for removing limescale or urine stains;

[0076] Pipe cleaning products or sewer cleaners. These are typically strongly alkaline products, generally used to remove pipe blockages containing organic matter such as hair, grease, food residue, soap deposits, etc. Additives of Al or Zn powder can be used to generate H2 gas, which has a foaming effect. Permissible ingredients are typically alkalis, alkaline salts, oxidizing agents, and neutral salts. Powdered forms of supply preferably also include sodium nitrate and sodium chloride. Liquid pipe cleaning products may also preferably include hypochlorite. Enzyme-based sewer cleaners also exist. Acidic products are also possible.

[0077] Multi-purpose or general-purpose cleaners. These are cleaners that can be widely used in homes and businesses to clean all hard surfaces that can be wetted or dampened. Generally, they are neutral, slightly alkaline, or slightly acidic products, especially liquid products. Multi-purpose or general-purpose cleaners typically contain surfactants, builders, solvents and water-soluble promoters, dyes, preservatives, etc.; multi-purpose cleaners with special disinfecting properties. They also include active antibacterial ingredients (e.g., aldehydes, alcohols, quaternary ammonium compounds, amphoteric surfactants, triclosan);

[0078] Hygiene cleaners. These are products used for cleaning bathrooms and toilets. Alkaline hygiene cleaners are preferred for removing oily stains, while acidic hygiene cleaners are particularly effective at removing limescale. Hygiene cleaners also have a fairly strong disinfecting effect, especially chlorine-based strong alkaline hygiene cleaners;

[0079] Oven cleaners or grill cleaners are available in gel or foam spray form. They are typically used to remove scorched or carbonized food residue. Oven cleaners are preferably provided as strongly alkaline formulations, using, for example, sodium hydroxide, sodium metasilicate, or 2-aminoethanol. Furthermore, they typically contain anionic and / or nonionic surfactants, water-soluble solvents, and in some cases, thickeners (e.g., polycarboxylate and carboxymethyl cellulose).

[0080] Glass cleaners and window cleaners. These products are preferably used to remove dirt, especially grease, from glass surfaces. Preferably, they contain compounds such as: anionic and / or nonionic surfactants (especially up to 5% by weight), ammonia and / or ethanolamine (especially up to 1% by weight), ethanol and / or 2-propanol, ethylene glycol ethers (especially 10-30% by weight), water, preservatives, dyes, antifogging agents, etc.; and

[0081] Consumer products can be beauty products, such as (a) skin care products for beauty purposes, especially bath products, skin cleansing and cleaning products, skin care products, eye cosmetics, lip care products, nail care products, feminine care products, and foot care products; or (b) beauty products with specific functions, especially sunscreens, tanning products, depigmenting products, deodorants, antiperspirants, hair removal products, shaving products, and fragrances; (c) dental care products for beauty purposes, especially dental and oral care products, teeth care products, denture cleaners, and denture adhesives; or (d) hair care products for beauty purposes, especially shampoos, hair care products, hair styling products, hair shaping products, and hair coloring products.

[0082] The invention will now be further described with reference to the following non-limiting embodiments. Variations and modifications that will be readily apparent to those skilled in the art are intended to fall within the scope of the invention as defined in or by the appended claims.

[0083] Example 1: ( S,E 10-Hydroxy-4,8-Dimethyldec-4-enal

[0084]

[0085] Example 1a: (3 S 5-(3,3-dimethylethyleneoxy-2-yl)-3-methylpentan-1-ol:

[0086] At room temperature (rt), add to a flask under nitrogen atmosphere. (S)3,7-Dimethyloct-6-en-1-ol (15.627 g, 18.3 mL, 1 Eq, 100.00 mmol), sodium carbonate (3.71 g, 0.35 Eq, 35.000 mmol), and toluene (76 mL) were added, and the mixture was cooled to 15 °C (ice bath). The mixture was then treated dropwise over 3 h with a peracetic acid solution in acetic acid (26.41 g, 23.06 mL, 36 wt%, 1.25 Eq, 125.00 mmol) while maintaining the temperature below 25 °C. After addition, the mixture was stirred at rt for 1 h, then poured onto a saturated aqueous solution of Na₂CO₃ (100 mL), extracted with MTBE (methyl tert-butyl ether) (2 × 100 mL), washed with brine (100 mL), dried over MgSO₄, filtered, concentrated, and finally dried at rt and 0.18 mbar to give a colorless liquid (3... S )-5-(3,3-dimethylethyleneoxy-2-yl)-3-methylpent-1-ol (17.21 g, quantitative yield).

[0087] 1 ¹H NMR (400MHz, CDCl₃, 298K, mixture of diastereomers) δ (ppm) = 3.81 - 3.61 (m, 2H), 2.77 - 2.67 (m, 1H), 1.71 - 1.35 (m, 8H), 1.33 (s, 3H), 1.28 (s, 3H), 0.97 - 0.91 (3H).

[0088] 13 C NMR (101MHz, CDCl3, 298K, mixture of diastereomers) δ (ppm) = 64.7, 64.7, 61.0, 58.3, 39.8, 39.6, 33.8, 33.7, 29.4, 29.2, 26.4, 26.2, 24.9, 19.7, 19.5, 18.7, 18.7.

[0089] Example 1b:

[0090] (3 S 3,7-Dimethyloct-7-ene-1,6-diol: At room temperature (rt), add (3...) to a flask under nitrogen atmosphere. S5-(3,3-dimethylethyleneoxy-2-yl)-3-methylpentan-1-ol (17.21 g, 1 Eq, 99.90 mmol) and toluene (200 mL) were mixed. The mixture was then treated with aluminum triisopropoxy (40.81 g, 2 Eq, 199.8 mmol) under reflux and stirred for 22 h. The resulting mixture was poured onto 100 mL of 4 M NaOH aqueous solution, extracted with MTBE (methyl tert-butyl ether) (2 × 100 mL), washed with 100 mL of brine, dried over MgSO4, filtered and concentrated. The crude product was purified by bulb-to-bulb distillation in a Kugeljo apparatus (furnace at 175–190 °C, 0.065 mbar) to give a colorless liquid (3-) S 3,7-Dimethyloct-7-ene-1,6-diol (15.00 g, 80% yield, 92% GC purity).

[0091] 1 ¹H NMR (400MHz, CDCl₃, 298K, a mixture of diastereomers) δ (ppm) = 4.92 (tt, J =1.0, 1.8 Hz, 1H), 4.83 (s, 1H), 4.02 (br d, J = 5.1 Hz, 1H), 3.76 - 3.56 (m,2H), 2.31 - 2.20 (m, 1H), 2.16 (br d, J = 11.0 Hz, 1H), 1.72 (s, 3H), 1.67 -1.02 (m, 7H), 0.91 (dd, J = 1.5, 6.6 Hz, 3H).

[0092] 13 C NMR (101MHz, CDCl3, 298K, mixture of diastereomers) δ (ppm) = 147.6, 147.5, 111.1, 110.9, 76.3, 75.9, 60.8, 39.7, 39.7, 32.7, 32.5, 32.2, 32.1, 29.5, 29.2, 19.7, 19.7, 17.6, 17.4.

[0093] α D = -6.599°mL / (g·dm)(25℃, in EtOH)

[0094] Example 1c:

[0095] ( S,E )-10-hydroxy-4,8-dimethyldec-4-enal: At room temperature, add (3) to a flask under nitrogen atmosphere. S 3,7-Dimethyloctyl-7-ene-1,6-diol (7.00 g, 1 Eq, 40.6 mmol) and 3,6,9,12-tetraoxatetradec-1,13-diene (triethylene glycol divinyl ether) (19.7 g, 19.9 mL, 2.4 Eq, 97.5 mmol) were used. After 5 minutes, the mixture was treated with palladium acetate (1,10-phenanthroline) (164 mg, 0.01 Eq, 406 μmol) and then heated to an internal temperature of 68 °C (80 °C oil bath temperature) for 40 h. The reaction mixture was then heated to an internal temperature of 138 °C (160 °C oil bath temperature) for 40 min. The resulting mixture was then cooled to below 50 °C and treated sequentially with water (20.3 mL), acetone (13.2 mL), and 2N HCl aqueous solution (2.03 mL), and stirred at 25–50 °C for 30 min. Finally, the mixture was diluted with ethyl acetate (100 mL), filtered to remove solids, poured onto ice water (100 mL), extracted with ethyl acetate (2 × 100 mL), washed with brine (100 mL), dried over MgSO4, filtered, and concentrated. The crude product was purified by silica gel column chromatography to obtain a pale yellow liquid. S,E 10-Hydroxy-4,8-Dimethyldecyl-4-enal (3.80 g, 43% yield, 92% GC purity).

[0096] GC-MS

[0097] 1 H NMR (400MHz, CDCl3, 298K) δ (ppm) = 9.75 (t, J = 2.1 Hz, 1H), 5.19- 5.11 (m, 1H), 3.75 - 3.61 (m, 2H), 2.56 - 2.48 (m, 2H), 2.39 - 2.29 (m,2H), 2.10 - 1.92 (m, 2H), 1.67 - 1.11 (m, 8H), 0.91 (d, J = 6.6 Hz, 3H).

[0098] 13 C NMR (101MHz, CDCl3, 298K) δ (ppm) = 202.9, 132.8, 125.8, 61.0, 42.1, 39.8, 37.0, 31.9, 29.0, 25.3, 19.5, 16.1.

[0099] GC / MS (EI): m / z (%): 180 (2, [M-H2O]+ ), 162 (6), 136 (17), 121 (66), 93 (52), 81 (81), 67 (54), 55 (100), 41 (96).

[0100] α D = -5.833°mL / (g·dm)(25℃, in EtOH)

[0101] The fragrance notes were evaluated by a skilled panel of members using a 1% ethanol solution on scent paper. Scent description: floral, lily of the valley, rose, aldehydes, metallic.

[0102] Example 2: ( R,E 10-Hydroxy-4,8-Dimethyldec-4-enal

[0103] As described in Example 1, the corresponding ( S,E The )-isomer is prepared in the same way, but starting from ( R )-3,7-dimethyloct-6-en-1-ol, yielding a pale yellow liquid ( R,E )-10-hydroxy-4,8-dimethyldecyl-4-enal. All analytical data were identical to its enantiomer (from Example 1), except:

[0104] α D = 4.869°mL / (g·dm)(23℃, in EtOH)

[0105] The fragrance notes were evaluated by a skilled panel of members using a 1% ethanol solution on scent paper. Scent description: Aldehydic, hot iron, metallic, sharp, light floral, slightly lily-of-the-valley.

[0106] Example 3: OR10J5 was ( S,E Activated by (R,E)-10-hydroxy-4,8-dimethyldec-4-enal (from Example 1) or (R,E)-10-hydroxy-4,8-dimethyldec-4-enal (from Example 2).

[0107] To construct the expression plasmid for OR10J5, a human OR10J5 gene with an optimized C-terminus (DNA sequence SEQ ID NO: 1 and amino acid sequence SEQ ID NO: 2) was synthesized by a DNA synthesis service provider (BioCat GmbH, Germany) and inserted downstream of the CMV promoter sequence (SEQ ID NO: 3) and before the bgh terminator sequence (SEQ ID NO: 4) of pcDNA3.1(+) (Invitrogen, MA, USA). The synthesized OR10J5 nucleotide sequence further contains a nucleotide sequence encoding a signal peptide (mmLucy-FLAG-rho) (SEQ ID NOs 5 and 6) at its 5'-terminus. Therefore, this plasmid contains constitutively expressed OR genes.

[0108] OR10J5 gene expression was performed in HEK293T cells stably transfected with DNA sequences encoding functional variants of human RTP1S (V227I, SEQ ID NO: 7 and 8) and RTP2 (L220R, SEQ ID NO: 9 and 10). These cells were seeded at a density of 10,000 cells / well in polyethyleneimine-coated 96-well plates (100 μL / well) and grown at 37°C for 24 h in the presence of 5% CO2.

[0109] 0.625 μg of OR10J5 expression plasmid, 1 μg of empty pcDNA3.1(+) vector, and 1 μg of pGL4.29 (Promega) carrying CRE-inducible luciferase were diluted in 0.25 ml of OptiMEM medium (Gibco). TM In a parallel step, 15 μL of Lipofectamine 2000 (Invitrogen) was diluted in 0.25 mL of OptiMEM medium, and after a 5 min pre-incubation, the two mixtures were combined to prepare the transfection mixture, which was then incubated for another 25 min.

[0110] Replace 50 μL of growth medium with fresh DMEM containing 9% fetal bovine serum (FBS). Dilute the pre-incubated transfection mixture to 5.5 mL with OptiMEM medium and add 50 μL of the diluted mixture to each well (total volume 150 μL). Incubate the cells further at 37 °C for 24 h in the presence of 5% CO2 to allow DNA uptake and OR10J5 expression.

[0111] OR10J5 was measured by removing 100 μL of growth medium and adding 50 μL of DMEM containing 9% FBS, 1% DMSO, and different concentrations of two test substances. S,E Activation was performed using (R,E)-10-hydroxy-4,8-dimethyldecyl-4-enal (from Example 1) or (R,E)-10-hydroxy-4,8-dimethyldecyl-4-enal (from Example 2). After incubation for 4.5 h, cells were lysed using 20 μL of passive lysis buffer (Promega), and luciferase signaling was measured based on OR-dependent cAMP production induction.

[0112] The potency of the OR10J5 ligand in both tests is expressed as the EC20% value, which is the concentration that results in a 20% increase in luciferase activity relative to the positive control (100 μM, (4E)-9-hydroxy-5,9-dimethyldecyl-4-enal). S,E The EC20% value of (R,E)-10-hydroxy-4,8-dimethyldecyl-4-enal (from Example 1) was 10.1 μM, while that of (R,E)-10-hydroxy-4,8-dimethyldecyl-4-enal (from Example 1) was 24.4 μM. Due to the difference in EC20%, a much lower concentration of the (S,E)-isomer (Example 1) is required to activate the receptor compared to the concentration required for the (R,E)-isomer (Example 2). Figures 2 and 3 graphically illustrate the responses of the two test compounds.

[0113] OR10J5 (SEQ ID NO 1) with an optimized C-terminal DNA sequence:

[0114] ATGAAGAGAAAGAACTTCACAGAAGTGTCAGAATTCATTTTCTTGGGATTTTCTAGCTTTGGAAAGCATCAGATAACCCTCTTTGTGGTTTTCCTAACTGTCTACATTTTAACTCTGGTTGCTAACATCATCATTGTGACTATCATCTGCATTGACCATCATCTCCACACTCCCATGTATTTCTTCCTAAGCATGCTGGCTAGTTCAGAGACGGTGTACACACTGGTCATTGTGCCACGAATGCTTTTGAGCCTCATTTTTCATAACCAACCTATCTCCTTGGCAGGCTGTGCTACACAAATGTTCTTTTTTGTTATCTTGGCCACTAATAATTGCTTCCTGCTTACTGCAATGGGGTATGACCGCTATGTGGCCATCTGCAGACCCCTGAGATACACTGTCATCATGAGCAAGGGACTATGTGCCCAGCTGGTGTGTGGGTCCTTTGGCATTGGTCTGACTATGGCAGTTCTCCATGTGACAGCCATGTTCAATTTGCCGTTCTGTGGCACAGTGGTAGACCACTTCTTTTGTGACATTTACCCAGTCATGAAACTTTCTTGCATTGATACCACTATCAATGAGATAATAAATTATGGTGTAAGTTCATTTGTGATTTTTGTGCCCATAGGCCTGATATTTATCTCCTATGTCCTTGTCATCTCTTCCATCCTTCAAATTGCCTCAGCTGAGGGCCGGAAGAAGACCTTTGCCACCTGTGTCTCCCACCTCACTGTGGTTATTGTCCACTGTGGCTGTGCCTCCATTGCCTACCTCAAGCCGAAGTCAGAAAGTTCAATAGAAAAAGACCTTGTTCTCTCAGTGACGTACACCATCATCACTCCCTTGCTGAACCCTGTTGTTTACAGTCTGAGGAACAAAGAAGTTAAAGATGCCTTAAAGAGGTTGCTAAAGAGAAAGTGCTGCTGA

[0115] OR10J5 (SEQ ID NO 2) with an optimized C-terminal amino acid sequence:

[0116] MKRKNFTEVSEFIFLGFSSFGKHQITLFVVFLTVYILTLVANIIIVTIICIDHHLHTPMYFFLSMLASSETVYTLVIVPRMLLSLIFHNQPISLAGCATQMFFFVILATNNCFLLTAMGYDRYVAICRPLRYTVIMSKGLCAQLVCGSFGIGLTMAVLHVTAMFNLPFCGTVVDHFFCDIYPVMKLSCIDTTINEIINYGVSSFVIFVPIGLIFISYVLVISSILQIASAEGRKKTFATCVSHLTVVIVHCGCASIAYLKPKSESSIEKDLVLSVTYTIITPLLNPVVYSLRNKEVKDALKRLLKRKCC

[0117] CMV promoter DNA sequence (SEQ ID NO 3)

[0118] GTTGACATTGATTATTGACTAGTTATTAATAGTAATCAATTACGGGGTCATTAGTTCATAGCCCATATATGGAGTTCCGCGTTACATAACTTACGGTAAATGGCCCGCCTGGCTGACCGCCCAACGACCCCCGCCCATTGACGTCAATAATGACGTATGTTCCCATAGTAACGCCAATAGGGACTTTCCATTGACGTCAATGGGTGGAGTATTTACGGTAAACTGCCCACTTGGCAGTACATCAAGTGTATCATATGCCAAGTACGCCCCCTATTGACGTCAATGACGGTAAATGGCCCGCCTGGCATTATGCCCAGTACATGACCTTATGGGACTTTCCTACTTGGCAGTACATCTACGTATTAGTCATCGCTATTACCATGGTGATGCGGTTTTGGCAGTACATCAATGGGCGTGGATAGCGGTTTGACTCACGGGGATTTCCAAGTCTCCACCCCATTGACGTCAATGGGAGTTTGTTTTGGCACCAAAATCAACGGGACTTTCCAAAATGTCGTAACAACTCCGCCCCATTGACGCAAATGGGCGGTAGGCGTGTACGGTGGGAGGTCTATATAAGCAGAGCTC

[0119] bgh terminator DNA sequence (SEQ ID NO 4)

[0120] CTGTGCCTTCTAGTTGCCAGCCATCTGTTGTTTGCCCCTCCCCCGTGCCTTCCTTGACCCTGGAAGGTGCCACTCCCACTGTCCTTTCCTAATAAAATGAGGAAATTGCATCGCATTGTCTGAGTAGGTGTCATTCTATTCTGGGGGGTGGGGTGGGGCAGGACAGCAAGGGGGAGGATTGGGAAGACAATAGCAGGCATGCTGGGGATGCGGTGGGCTCTATGG

[0121] mmLucy-FLAG-rho DNA sequence (SEQ ID NO 5)

[0122] ATGAGCCACCAGATCCTGCTGCTCCTGGCCCTGCTGACCCTAGGCCTGGCTGATTACAAGGACGACGACGATAAGATCGAATTGATGAACGGGACCGAGGGCCCAAACTTCTACGTGCCTTTCTCCAACAAGACGGGCGTGGTGGAATTC

[0123] mmLucy-FLAG-rho amino acid sequence (SEQ ID NO 6)

[0124] MSHQILLLLALLTLGLAMDYKDDDDKMNGTEGPNFYVPFSNKTGVVEF

[0125] RTP1S(V227I) DNA sequence (SEQ ID NO 7)

[0126] ATGTGTAAAAGCGTGACCACAGATGAGTGGAAGAAAGTCTTCTATGAGAAGATGGAGGAGGCAAAGCCGGCTGACAGCTGGGACCTCATCATAGACCCCAACCTCAAGCACAATGTGCTGAGCCCTGGTTGGAAGCAGTACCTGGAATTGCATGCTTCAGGCAGGTTCCACTGCTCCTGGTGCTGGCACACCTGGCAGTCGCCCTACGTGGTCATCCTCTTCCACATGTTCCTGGACCGCGCCCAGCGGGCGGGCTCGGTGCGCATGCGCGTCTTCAAGCAGCTGTGCTATGAGTGCGGCACGGCGCGGCTGGACGAGTCCAGCATGCTGGAGGAGAACATCGAGGGCCTGGTGGACAACCTCATCACCAGCCTGCGCGAGCAGTGCTACGGCGAGCGTGGCGGCCAGTACCGCATCCACGTGGCCAGCCGCCAGGACAACCGGCGGCACCGCGGAGAGTTCTGCGAGGCCTGCCAGGAGGGCATCGTGCACTGGAAGCCCAGCGAGAAGCTGCTGGAGGAGGAGGCGACCACCTACACCTTCTCCCGGGCGCCCAGCCCCACCAAGTCGCAGGACCAGACGGGCTCAGGCTGGAACTTCTGCTCTATCCCCTGGTGCTTGTTTTGGGCCACGGTCCTGCTGCTGATCATCTACCTGCAGTTCTCTTTCCGTAGCTCCATCTAA

[0127] Amino acid sequence of RTP1S(V227I) (SEQ ID NO: 8)

[0128] MCKSVTTDEWKKVFYEKMEEAKPADSWDLIIDPNLKHNVLSPGWKQYLELHASGRFHCSWCWHTWQSPYVVILFHMFLDRAQRAGSVRMRVFKQLCYECGTARLDESSMLEENIEGLVDNLITSLREQCYGERGGQYRIHVASRQDNRRHRGEFCEACQEGIVHWKPSEKLLEEEATTYTFSRAPSPTKSQDQTGSGWNFCSIPWCLFWATVLLLIIYLQFSFRSSI

[0129] RTP2 (L220R) DNA sequence (SEQ ID NO 9)

[0130] ATGTGTACCAGCTTGACCACTTGTGAGTGGAAGAAAGTCTTCTATGAGAAGATGGAGGTGGCAAAGCCAGCGGACAGCTGGGAGCTCATCATAGACCCCAACCTCAAGCCCAGTGAGCTGGCCCCTGGCTGGAAGCAGTACCTGGAGCAGCACGCCTCAGGCAGGTTCCACTGCTCCTGGTGCTGGCACACCTGGCAGTCTGCCCATGTGGTCATCCTCTTCCACATGTTCCTGGACCGCGCCCAGCGGGCGGGCTCGGTGCGCATGCGCGTCTTCAAGCAGCTGTGCTATGAGTGCGGCACGGCGCGGCTGGACGAGTCCAGCATGCTGGAGGAGAACATCGAGGGCCTGGTGGACAACCTCATCACCAGCCTGCGCGAGCAGTGCTACGAGGAGGATGGTGGCCAGTACCGCATCCACGTGGCCAGCCGCCCGGACAGCGGGCCGCATCGTGCAGAGTTCTGTGAGGCCTGCCAGGAGGGCATCGTTCACTGGAAGCCCAGCGAGAAGCTGCTGGAGGAGGAGGTGACCACCTACACCTCTGAAGCCTCCAAGCCGAGGGCCCAGGCGGGATCCGGCTACAACTTCTTGTCTCTTCGCTGGTGCCTCTTCTGGGCCTCTCTCTGCCTGCTCGTTGTTTACCTGCAGTTCTCCTTCCGCAGTCCTGCCTTCTTTTAG

[0131] RTP2 (L220R) amino acid sequence (SEQ ID NO 10)

[0132] MCTSLTTCEWKKVFYEKMEVAKPADSWELIIDPNLKPSELAPGWKQYLEQHASGRFHCSWCWHTWQSAHVVILFHMFLDRAQRAGSVRMRVFKQLCYECGTARLDESSMLEE NIEGLVDNLITSLREQCYEEDGGQYRIHVASRPDSGPHRAEFCEACQEGIVHWKPSEKLLEEEVTTYTSEASKPRAQAGSGYNFLSLRWCLFWASLCLLVVYLQFSFRSPAFF

[0133] Example 4

[0134] A powdery floral cologne with a fresh fruity top note and a powdery amber base note. S,E Adding a transparent floral aroma to the dry base fragrance with (R,E)-10-hydroxy-4,8-dimethyldecyl-4-enal significantly improves the overall pleasantness of the fragrance and reduces its strong sillage. However, the addition of transparent floral aroma and a slightly metallic aldehyde layer with (R,E)-10-hydroxy-4,8-dimethyldecyl-4-enal negatively impacts the pleasant balance of the fragrance.

[0135]

Claims

1. According to equation (I), ( S,E 10-Hydroxy-4,8-Dimethyldec-4-enal 。 2. A flavoring composition comprising the compound according to claim 1 and at least one other flavoring ingredient.

3. The fragrance composition according to claim 2, wherein the compound of formula (I) is in enantiomeric form.

4. The fragrance composition according to claim 2, comprising (R,E) 10-hydroxy-4,8-dimethyldecyl-4-enal, wherein the compound according to claim 1 is in an enantiomeric enriched form.

5. The fragrance composition according to claim 4, wherein the compound according to formula (I) is present in an enantiomeric excess of at least 60%.

6. The spice composition according to any one of claims 2 to 5, comprising ( S,Z )-10-hydroxy-4,8-dimethyldec-4-enal.

7. The fragrance composition according to any one of claims 2 to 6, comprising at least one fragrance ingredient selected from: 2-cyclohexyl-2-phenylacetonitrile, such as paeononitrile™; 4-(octahydro-4,7-methylene-5H-inden-5-ylidene)butyraldehyde, such as Doubicarr™; and 4-methyl-2-(2-methylpropyl)tetrahydro-2H-pyran-4-ol, such as lily of the valley™; methyl 2-(2-hexyl-3-oxocyclopentyl)acetate, such as methyl dihydrojasmonate™; natural ingredients, such as those selected from iris, mimosa, ylang-ylang, bergamot, jasmine, and rose; and synthetic lily of the valley fragrance. The fragrance components include, for example, citronellal (103-95-7), hydroxycitronellal (107-75-5), hydroxycitronellal diethyl acetal (7779-94-4), silver aldehyde (6658-48-6), berberine aldehyde (18127-01-0), anthocyanin (125109-85-5), and lily of the valley aldehyde (7775-00-0); rose-type floral components include, for example, ethyl phenyl alcohol (60-12-8), dimethyl phenylethyl alcohol (103-05-9), citronellol (106-22-9), rose alcohol (106-22-9), and Acet.DMBC. (151-05-3), Geraniol (106-24-1), Nerol (106-25-2), Nerolidol (7212-44-4), Roseol (55066-48-3), o-methylphenylethanol (19819-98-8), Citronellol isobutyrate (97-89-2), and Mefenoxate (103694-68-4); Freesia-type floral components, such as Linalool (78-70-6), Rossitol (215231-33-7), and Corticoyl alcohol (83926-73-2); Lilac-type floral components, such as Ale.Cinnamyl alcohol (104-54-1), propylphenyl alcohol (122-97-4), and terpineol (8000-41-7); jasmine-type floral components, such as benzyl acetate (140-11-4), methyl dihydrojasmonate (24851-98-7), hexylcinnamaldehyde (101-86-0), and pentylcinnamaldehyde (122-40-7); lily-of-the-valley-type floral components, such as super lily-of-the-valley (26330-65-4), hydroxycitronellol dimethyl acetate (141-92-4), magnolol (92046-49-6), mugetanol (63767-86-2), and mugesia. (56836-93-2), indole (120-72-9) and indoleene liquid (67860-00-8); green aromatic components, such as cis-3-hexenol (928-96-1), phenylacetaldehyde (122-78-1), marsé aldehyde (67845-30-1), cis-3-hexenyl acetate (3681-71-8), acetal CD (29895-73-6), precarone (74499-58-4), Mevlanal (55066-49-4), Alintal (40910-49-4), Gliclazide dioxane (68901-32-6), and Corticosteroids (83926-73-2); refreshing ingredients, such as C11 undecenal (112-45-8), C11 undecenal (112-44-7), C10 aldehyde (112-31-2), C12 MNA aldehyde (110-41-8), Neo-jasmine aldehyde (1205-17-0), citral (5392-40-5), Oxydede Limette (73018-51-6), anthocyanin (125109-85-5), fenestration aldehyde (67634-15-5), dihydrofarnesal (51513-58-7), dihydrofarnesol (51411-24-6), adolphin (141-13-9), citronellol (7492-67-3), super lily of the valley aldehyde (71077-31-1), and dodecenal (4826-62-4); woody components, such as ionone (8013-90-9) and methyl ionone (1335-46-2); powdery components, such as musk (21145- 77-7), Tibetan musk (106-02-5), jasmine aldehyde (120-57-0), and vanillin (121-33-5); various harmonious floral components, such as hydroxycitronellol (107-75-5), farnesal (19317-11-4), farnesyl acetate (29548-30-9), rose acetate (141-11-7), cyclomethylene citronellol (15760-18-6), lily of the valley alcohol (5502-75-0), hesperidin acetate (72403-67-9), and methoxydihydrocitronellol (3613-30-7); and mixtures thereof.

8. The fragrance composition according to any one of claims 2 to 7, wherein it is free of or substantially free of lily aldehyde or doubicarbaldehyde.

9. A compound of formula (I) or a fragrance composition as defined in any one of claims 2 to 8, used to mask or reduce one or more unpleasant odor impressions of one or more substances having an unpleasant odor. And / or for use in enhancing one or more pleasant odor impressions of one or more substances having a pleasant odor.

10. The use according to claim 9, wherein the pleasant odor impression is the scent of lily of the valley.

11. A consumer product comprising a compound according to formula (I) or a fragrance composition according to any one of claims 2 to 8.

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