Perfume ingredients and compositions containing them

Abstract

The compound (−)-(E)-1-((1S,2R)-2,6,6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one, and its use in perfumery.

Description

[0001] PERFUME INGREDIENTS AND COMPOSITIONS CONTAINING THEM

[0002] The present invention is concerned with novel perfume ingredients, their methods of preparation and compositions containing them.

[0003] Background of the invention

[0004] The damascone family comprises four isomers, namely alpha-damascone, beta-damascone, delta- damascone and gamma damascone. Delta-damascone is by far the most widely used of the three isomers in perfumery because of its highly sought-after unique fruity tonality and its low cost.

[0005] Delta damascone is the trivial name of the perfume ingredient (E)-1-(2,6,6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one. Although the molecule has two chiral centers, the commercial grade of delta damascone consists mainly of the racemic mixture of the trans isomer

[0006] Despite its highly desirable hedonics and low cost in use, delta damascone, is the only one of the four damascone isomers that is not biodegradable. This can create issues in modern perfumery because customers and consumers alike are increasingly looking for their perfume suppliers to produce ingredients that not only deliver delightful hedonics, but to also deliver on other metrics, such as sustainability and biodegradability.

[0007] Novel ingredients or novel forms of ingredients are sought after that can serve as replacers or alternatives for the fruity tonalities of delta damascone that are more impactful than the commercial grade delta damascone and therefore both sustainable and cost-effective in application as such, as well as being biodegradable. of the invention

[0008] The applicant has addressed the deficiencies in the prior art and provides in a first aspect the compound (-)-(E)-1-((1S,2R)-2,6,6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one, as represented by and referred to herein after as the compound of formula (I) The invention provides in a second aspect a method of making the compound of formula (I).

[0009] The invention provides in a third aspect a perfume mixture comprising the compound of formula (I).

[0010] The invention provides in a fourth aspect the use of a compound of formula (I) and perfume mixtures containing same in perfumery, in particular to impart, enhance or improve a pleasant odour impression or to mask, reduce or eliminate an unpleasant odour impression.

[0011] The invention provides in a fifth aspect a consumer product containing the compound of formula (I) or a perfume mixture containing same.

[0012] The details, examples and preferences provided in relation to any one or more of the stated aspects of the present invention will be further described herein and apply equally to all aspects of the present invention. Any combination of embodiments, examples and preferences described herein below in all possible variations thereof are encompassed by the present invention unless otherwise indicated herein, or otherwise clearly contradicted by context.

[0013] Detailed description of the invention

[0014] The first aspect of the invention relates to the compound of formula (I), as well as its use as a perfume ingredient in all manner of perfumery applications from fine perfumery to perfumery in consumer products. The invention is based, in part, on the surprising discovery that the compound of formula (I) is biodegradable. This is particularly surprising considering that the enantiomer of the compound of formula (I), that is (+)-(E)-1-((1R,2S)-2,6,6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one, (hereafter also referred to as the compound of formula (II), shown below), and also the racemic mixture of the trans isomer of delta damascone, are not biodegradable.

[0015] In the context of the present invention, a material is considered to be biodegradable if it meets the pass criteria in accordance with OECD manometric respirometry methods, and in particular the OECD 301 F method, which methods are well known in the art. In the 301 F test method the pass level for a material to be considered as having “ready biodegradability” or being “readily biodegradable” is to reach 60 % of theoretical oxygen demand and / or chemical oxygen demand. This pass value has to be reached in a 10-day window within the 28-day period of the test. The 10-day window begins when the degree of biodegradation has reached 10% of theoretical oxygen demand and / or chemical oxygen demand and must end before day 28 of the test. A preferred way of conducting OECD Method 301 F is provided herein below.

[0016] Given a positive result in a test of ready biodegradability, it may be assumed that a material will undergo rapid and ultimate 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; Adopted: July 2003).

[0017] An assessment of “inherently biodegradable” can also be made using the OECD Method 301 F, although with a different pass criterion. More specifically, the pass criterion is 60 % of theoretical oxygen demand and / or chemical oxygen demand. This pass value can be reached after the 28-day period of the test, which is usually extended to 60 days. No 10-day window applies.

[0018] An additional advantage of the compound of formula (I) resides in the discovery of its surprising sensorial properties. More specifically, the compound of formula (I) was discovered to have a very pleasant fruity tonality that was practically the same as, or even more pleasant than its racemic mixture, and could be used as a drop-in replacement for the racemic mixture, as such. However, despite the similarities in tonality, it was unexpectedly discovered that the compound of formula (I) was far more impactful than the compound of formula (II) and at least as impactful as the racemic mixture. The compound of formula (I) thereby affords the perfumer the opportunity to access essentially the same tonality as the racemic mixture but use less material, thereby allowing the perfumer to create more sustainably and cost-effectively.

[0019] The unusual intensity of the compound of formula (I) compared to the compound of formula (II) or the racemic mixture was discovered by threshold measurements carried out on GC and corroborated by comparing measured EC 50 values obtained by means of an in-vitro assay employing a novel olfactory receptor discovered by the applicant to be implicated in the human sensing of the damascone isomers. This test and the novel olfactory receptors are more fully described in the Examples, below.

[0020] The potency of the compound of formula (I) compared to its enantiomer, the compound of formula (II), is significant and of particular interest to perfumers for reasons related to sustainability and economy.

[0021] These surprising discoveries provide perfumers with a novel perfumery ingredient that can provide all of the hedonic performance of the commercially available delta damascone comprising the racemic mixture, but in a sustainable, cost-effective and biodegradable format.

[0022] Methods of preparing the compound of formula (I) represent a second aspect of the invention. In particular embodiments of the invention, the compound of formula (I) may be prepared by the chiral separation of the racemic mixture or a scalemic mixture of the compound of formula (I) and the compound of formula (II). The aforementioned mixtures as such may be separated, or the racemic mixture or scalemic mixture can be part of a more complex mixture, such as for instance the commercial grade delta damascone.

[0023] The racemic mixture is present in the commercially available grade of delta damascone, and can be prepared according to methods known in the art. A suitable method for preparing the racemic mixture is described in WO2010 / 80504 or US4460792, which methods disclosed in said references are hereby incorporated by reference.

[0024] Chiral resolution of a racemic mixture or a scalemic mixture can be carried out according to various methods including but not limited to 1 ,4-conjugated addition of N, O, C and S-containing nucleophiles to (E)-1-(2,6,6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one; asymmetric chemical or enzymatic reduction (which may be, but is not limited to, the reduction of an olefin including an enone or of a carbonyl group) or oxidation (which may be, but is not limited to, epoxidation of an olefin or Bayer- Villiger oxidation) of (E)-1-(2,6,6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one, or 1 -(2,6,6- trimethylcyclohex-3-en-1-yl)ethan-1-one, or asymmetric chemical or enzymatic aldol condensation of 1-(2,6,6-trimethylcyclohex-3-en-1-yl)ethan-1-one; or asymmetric allylic oxidation of (E)-1 -(2,6,6- trimethylcyclohex-3-en-1-yl) but-2-en-1-one or 1-(2,6,6-trimethylcyclohex-3-en-1-yl) ethan-1-one.

[0025] In all cases where the enantiomer-determining reaction described above is performed on 1 -(2,6,6- trimethylcyclohex-3-en-1-yl) ethan-1-one, the resulting enantiomerically enriched 1-((1S,2R)-2,6,6- trimethylcyclohex-3-en-1-yl) ethan-1-one is converted to the compound of formula (I) according to the process described for the synthesis of the racemic delta damascone described in WO2010 / 80504 or US4460792.

[0026] In a particular embodiment of this aspect of the present invention, the chiral resolution of the racemic or scalemic mixture is carried out according to the addition of chiral amine or amino acid esters to (E)- 1-(2,6,6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one, as for example described for other enones in Tetrahedron Letters, 2013, 2669.

[0027] In another particular embodiment of this aspect of the present invention, the chiral resolution of the racemic or scalemic mixture is carried out according to a process of addition of organometallic reagents e.g., organo-zinc, -magnesium, -aluminum, or -cuprate to (E)-1-(2,6,6-trimethylcyclohex-3-en- 1-yl) but-2-en-1-one, as described in the literature (e.g. Chem. Commun. 2005, 2843-2845, J. Am. Chem. Soc. 2004, 12784, Chem. Rev. 2008, 2824), resulting in the preferential addition of the organometallic reagent to the compound of formula (II), and isolating the desired, unreacted compound of formula(l) in scalemic form. In another particular embodiment, the compound of formula (I) may be prepared according to a method of hydrogenation of (E)-1-(2,6,6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one by means of a metal catalyst in combination with a chiral ligand and a hydrogen source (e.g. molecular hydrogen, silanes, alcohols, formic acid / base). A particular example of this chemical synthesis is set out in Examples herein below.

[0028] In the syntheses described above, reference is made to reactants containing the (E)-geometry, However, the syntheses apply equally to reactants having (Z) geometry and the resultant compound isomerized to the (E)-geometry.

[0029] The third aspect of the invention relates to a perfume mixture comprising a compound of formula (I).

[0030] A perfume mixture according to the invention comprises the compound of formula (I) and at least one other perfume ingredient and / or adjuvant that may be typically employed in perfumery, wherein the compound of formula (I) is either in enantiopure form or is in a scalemic mixture, in which it is the enriched enantiomer.

[0031] In a particular embodiment of the invention, the perfume mixture comprises the compound of formula (I) and is free of the compound of formula (II), that is, the compound of formula (I) is present in the perfume mixture in enantiopure form.

[0032] In another particular embodiment of the invention, the perfume mixture comprises or consists of a scalemic mixture of the compound of formula (I) and the compound of formula (II), in which the scalemic mixture is enriched in the compound of formula (I).

[0033] In more particular embodiments of the invention, the perfume mixture comprises or consists of a scalemic mixture of the compound of formula (I) and the compound of formula (II) in which the compound of formula (I) is present in an enantiomeric excess of 10 % or greater, 20 % or greater, 30 % or greater, 40 % or greater, 50 % or greater, 60 % or greater, 70 % or greater, 80 % or greater, or 90 % or greater.

[0034] Particularly preferred are scalemic mixtures in which the compound of formula (I) is in an enantiomeric excess of about 70 % or greater, and more particularly about 80 % or greater. The applicant found that such mixtures are solid at a temperature of about 20 °C or below, and as such during preparation and purification of the scalemic mixture, it can be more easily recovered from a reaction mixture.

[0035] In another particular embodiment of the invention the perfume mixture comprises the compound of formula (I) in enantiopure form, or in a scalemic mixture as describe above, and the compound 1- ((1 R,2S)-2,6,6-trimethylcyclohex-3-en-1-yl) butan-1-one. In another particular embodiment of the invention the perfume mixture comprises the compound of formula (I) in enantiopure form, or in a scalemic mixture as describe above, and racemic or scalemic dihydro damascone, that is 1-(2,6,6-trimethylcyclohex-3-en-1-yl) butan-1-one.

[0036] Perfume mixtures according to the invention may contain one or more additional perfumery ingredients useful in all manner of perfumery applications. These perfume ingredients may include any of the perfumery essential oils, alcohols, aldehydes, ketones, ethers, acetals, esters, lactones, macrocycles and heterocycles commonly used in perfumery, as well as any excipients or adjuvants conventionally used in conjunction with such perfumery ingredients for example, solvents, diluents and other auxiliary agents commonly used in the art such as preservatives and the like. Such perfume ingredients are described in standard perfumery text books and references such as "Perfume and Flavour Chemicals", S. Arctander, Allured Publishing Corporation, 1994, IL, USA, and later editions thereof, which are incorporated herein by reference.

[0037] Having regard for the tonality and intensity of the compound of formula (I), the skilled perfumer may find it desirable to employ particular complementary perfume ingredients in combination with the compound of formula (I) in order to balance or fine tune its odour characteristics and that of perfume mixtures containing it.

[0038] Particular perfume ingredients that can be employed harmoniously with the compound of formula (I) include but are not limited to:

[0039] Natural ingredients, such as those selected from Iris, Mimosa, Ylang, Bergamot, jasmine and rose;

[0040] Synthetic muguet fragrance ingredients such as Cyclamen aldehyde (103-95-7), Hydroxycitronellal (107-75-5), Hydroxy Citronellal diethyl acetal (7779-94-4), Silvial (6658-48-6), Bourgeonal (18127-01- 0), Florhydral (125109-85-5), and Cyclemax (7775-00-0); and Dupical (30168-23-1).

[0041] Floral ingredients of the rose type such as ethyl phenyl alcohol (60-12-8), Dimethyl phenyl ethyl carbinol (103-05-9), Citronellol (106-22-9), Rhodinol (106- 22-9), Acet. DMBC (151-05-3), Geraniol (106-24-1), Nerol (106-25-2), Nerolidol (7212-44-4), Mefrosol (55066-48-3), Peomosa (19819-98-8), citronellyl iso butyrate (97-89-2), and Majantol (103694-68-4);

[0042] Floral ingredients of the freesia type such as Linalool (78-70-6), Rossitol (215231-33-7), and Coranol (83926-73-2);

[0043] Floral ingredients of the lilac type such as Ale. Cinnamic alcohol (104-54- 1), propyl phenyl alcohol (122-97-4) and Terpineol (8000-41-7); Floral ingredients of the jasmine type such as benzyl acetate (140-11-4), Hedione (24851-98-7), Hexyl Cinnamic aldehyde (101-86-0), and Amyl Cinnamic aldehyde (122-40-7);

[0044] Floral ingredients of the muguet type such as Super Muguet (26330-65- 4), Hydroxycitronellal dimethyl acetate (141-92-4), Magnol (92046-49-6),

[0045] Mugetanol (63767-86-2), Mugesia (56836-93-2), Indole (120-72-9), and Indolene (67860-00-8);

[0046] Green ingredients such as cis 3 Hexenol (928-96-1), phenyl acetic aldehyde (122-78-1), Maceal (67845-30-1), cis 3 hexenyl acetate (3681-71-8), Acetal CD (29895-73-6), Precarone (74499-58-4), Mefranal (55066-49-4), Elintaal (40910-49-4), Glycolierral (68901-32-6), and Coranol (83926-73-2);

[0047] Fresh ingredients such as C11 undecelenic aldehyde (112-45-8), C11 undecylic aldehyde (112-44-7), C 10 aldehyde (112-31-2), C 12 MNA aldehyde (110-41-8), Tropional (1205-17-0), Citral (5392-40-5), Oxyde de Limette (73018- 51-6), Florhydral (125109-85-5), Floralozone (67634-15-5), Dihydro Farnesal (51513-58-7), Dihydrofarnesol (51411-24-6), Adoxal (141-13-9), Citronellyl Oxyacetaldehyde (7492-67-3), Floral super (71077-31-1) and Dodecenal (4826-62-4);

[0048] Woody ingredients such as Irisone (8013-90-9) and methyl Ionone (1335-46-2);

[0049] Powdery ingredients such as Fixolide (21145-77-7), Thibetolide (106-02-5) , Heliotropine (120-57-0) and Vanilline (121-33-5);

[0050] Diverse harmonic floral ingredients such as Phixia (107-75-5), Farnesal (19317-11- 4), Farnesyle acetate (29548-30-9), Rhodinyl acetate (141-11-7), Cydomethylene Citronellol (15760-18-6), Mayol (5502-75-0), Myraldyl acetate (72403-67-9), and Melonia (3613-30-7), wherein the CAS numbers of the molecules are provided in parentheses; and any mixtures thereof.

[0051] Particularly preferred perfume mixtures according to the invention contain the contain a compound according to the formula (I) in enantiopure form or in the form of the scalemic mixture referred to herein above, and one or more perfume ingredients selected from the group consisting of:

[0052] - essential oils and extracts, e.g. agarwood oil (white and / or authentic), castoreum, costus root oil, oak moss absolute, geranium oil, tree moss absolute, basil oil, fruit oils, such as bergamot oil and mandarine oil, myrtle oil, palmarose oil, patchouli oil, petitgrain oil, jasmine oil, rose oil, sandalwood oil, wormwood oil, lavender oil or ylang-ylang oil;

[0053] - alcohols, e.g. cinnamic alcohol, c / s-3-hexenol, citronellol, Ebanol™, (1-methyl-2-((1 ,2,2- trimethylbicyclo [3.1.0] hexan-3-yl)methyl)cyclopropyl)methanol, (E)-3,3-dimethyl-5-(2,2,3- trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol, eugenol, farnesol, geraniol, Super Muguet™, linalool, menthol, nerol, phenylethyl alcohol, rhodinol, Sandalore™, terpineol orTimberol™, (S,E)-3,7- dimethylnon-6-en-1-ol, (1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropyl)methanol, 2,4,7-trimethyloct-6- en-1-ol;

[0054] - aldehydes and ketones, e.g. Azurone® [7-(3-methylbutyl)-1 ,5-benzodioxepin-3-one], anisaldehyde, a-amylcinnamaldehyde, Cashmeran®, Georgywood™, Hedione®, hydroxycitronellal, Iso E Super®, Isoraldeine®, Kephalis™, Lilial®, maltol, methyl cedryl ketone, methylionone, verbenone, or vanillin, 3- (4-isobutyl-2-methylphenyl)propanal, ethyl (Z)-2-acetyl-4-methyltridec-2-enoate, (E)-1 -(2,6,6- trimethylcyclohexa-1 ,3-dien-1-yl)but-2-en-1-one (beta damascone), ethyl 2,6,6-trimethylcyclohexa-1 ,3- diene-1 -carboxylate (ethyl safranate), (2E)-5,6,7-trimethylocta-2,5-dien-4-one (pomarose), (E)-1 - (2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one(alpha damascone), (E)-1-(2,6,6-trimethylcyclohex-1- en-1-yl)but-2-en-1-one (beta damascone);

[0055] - ether and acetals, e.g. Ambrox®, geranyl methyl ether, rose oxide, or Spirambrene®;

[0056] - esters and lactones, e.g. benzyl acetate, cedryl acetate, y-decalactone, Helvetolide®, y- undecalactone or vetivenyl acetate; 6 - macrocycles, e.g. Ambrettolide, ethylene brassylate or Exaltolide®, 2-(1-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropyl cyclopropanecarboxylate (Serenolide), (E)-2-((3,5-dimethylhex-3-en-2-yl)oxy)-2-methylpropyl cyclopropanecarboxylate (Sylkolide), ethyl 2-ethyl-6,6-dimethylcyclohex-2-ene-1-carboxylate(ethyl safranate), methyl 2,2- dimethyl-6-methylenecyclohexane-1 -carboxylate (Romascone), methyl 2,6,6-trimethylcyclohex-3-ene- 1-carboxylate (Firascone);

[0057] - heterocycles, e.g. isobutylchinoline; and

[0058] -macrocycles: 3-methylcyclopentadec-5-en-1-one (Muscenone), 3-methylcyclopentadecan-1-one (Muscone), (Z)-13-methyloxacyclopentadec-10-en-2-one (Nirvanolide), (Z)-cyclohexadec-5-en-1-one (Velvione).

[0059] As adjuvants or excipients that can be employed in perfume mixtures according to the invention, there can be mentioned any of those conventional ingredients, which are employed in perfumery for reasons other than, or not specifically related to, their odour characteristics. For example, an adjuvant or excipient may be an ingredient that acts as an aid to processing a perfume ingredient or ingredients, or a perfume mixture containing said ingredient(s), or it may improve handling or storage of a perfume ingredient or perfume mixture containing same. It might also be an ingredient that provides additional benefits such as imparting colour or texture. It might also be an ingredient that imparts light resistance or chemical stability to one or more ingredients contained in a perfume ingredient or perfume mixture containing same. A detailed description of the nature and type of such materials that can be employed in perfume mixtures containing same cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art. Examples include solvents and co-solvents; surfactants and emulsifiers; viscosity and rheology modifiers; thickening and gelling agents; preservative materials; pigments, dyestuffs and colouring matters; extenders, fillers and reinforcing agents; stabilisers against the detrimental effects of heat and light, bulking agents, acidulants, buffering agents and antioxidants.

[0060] Any one or more of the perfume ingredients or adjuvants or excipients employed in a perfume mixture according to the present invention can be formulated in a delivery vehicle if desired to provide a particular perfumery or functional effect, such as alteration of the spatio-temporal odour profile of the perfume mixture. Delivery vehicles may include microcapsules, or other solid support onto which one or more perfume ingredients or adjuvants may be chemically or physically bound. Still further, one or more perfume ingredients or adjuvants may be dissolved or dispersed in a matrix material, which serves to control the rate at which said ingredient or ingredients emanates therefrom. In yet an alternative embodiment, one or more ingredients or adjuvants may be supported on a porous substrate, such as a cyclodextrin or a zeolite or other inorganic material. In still further embodiments, one or more perfume ingredients may be provided in the form of a so-called pro-perfume or perfume precursor, which can be activated under certain conditions such as moisture, heat or light to release the perfume ingredient in a controlled manner. Having regard to the foregoing, it will be appreciated that a perfume mixture may be at least partly in solid form, in gel form, in foam form and / or liquid form. If it is present in solid form, it then it may take the form of granules, powders or tablets.

[0061] As stated already herein, the compound according to formula (I) is particularly useful at least in part because it is biodegradable as well as being sensorially very impactful. It may be used in perfumery, and in particular in perfume mixtures for its hedonic properties as well as to increase the percentage of biodegradable ingredients contained in such mixtures, or it may be used in combination with other biodegradable perfume ingredients to form entirely biodegradable perfume mixtures. Still further, consumer products comprising the compound of formula (I) or perfume mixtures of the invention therefore may also be considered to be comprised partially or totally of biodegradable materials.

[0062] The fourth aspect of the invention is related to the use of the compound of formula (I) and perfume mixtures containing same as a perfume ingredient in all manner of perfumery applications.

[0063] In particular embodiments of the invention, the compound of formula (I) and perfume mixtures containing same can be used as perfume ingredients in perfumery applications to impart, enhance or improve a pleasant odour impression or to mask, reduce or eliminate an unpleasant odour impression.

[0064] The unpleasant odour that is required to be reduced or eliminated may emanate from a consumer product into which the compound or perfume mixture is incorporated, or the unpleasant odour may emanate from a situs, such as the human or animal body, or an inanimate surface, onto which the consumer product is intended to be applied in order to treat an odour. The compound of formula (I) may be used as a perfume ingredient in widely varying amounts in perfumery applications depending upon the particular olfactive effect a skilled perfumer wants to achieve, as well as the type of application, it being understood by a skilled perfumer that usage levels may vary depending upon whether its use is in fine perfumery or in consumer products, and in which particular category of consumer product. Typical usage levels of the compound of formula (I) in perfume mixtures can vary can range widely, for example from 0.0001 to 100 wt%, more particularly 0.001 to 50 wt%, more particularly still 0.01 to 20 wt% and still more particularly 0.02 to 10 wt%, based on the total weight of the perfume mixture.

[0065] The compound of formula (I) exhibits odour characteristics that are substantially similar in tonality to the commercially available racemic mixture and can be used in perfumery as a replacer for the racemic mixture, as such. However, owing to its impactfulness, it could be used by perfumers in lower dosage.

[0066] The fifth aspect of the invention is concerned with consumer products containing the compound of formula (I) or perfume mixtures as defined herein.

[0067] The compound of formula (I) may be present in the consumer product in an amount ranging from about 0.0001 wt% to about 30 wt% based on the total weight of the consumer product. However, these values are given only by way of example, since the experienced perfumer may also achieve effects or may create novel accords with lower or higher concentrations.

[0068] The consumer product may be a personal care product, for example perfume extracts, eau de perfumes, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed freshening wipes, body care products, soap, liquid body wash, 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 cosmetic products (e.g. make-up).

[0069] The consumer product may be a cleaning product, for example, acidic, alkaline, and neutral cleaners, fabric fresheners, ironing aids, liquid detergents, fabric softeners, washing soaps, washing tablets, disinfectants (e.g. surface disinfectants), air fresheners, aerosol sprays, waxes and polishes.

[0070] The consumer product may be a homeware product, for example, candles, lamp oils, incense sticks, insecticides, repellents, and propellants.

[0071] The consumer product may be a household care product, for example a textile treatment product, an ironing aid, a cleaning cloth, a laundry detergent, a cleaning product, in particular, for hard and / or soft surfaces, a household cleaner, a care product, a wash care product, a laundry care product, a room fragrancer, and air freshener, a conditioner, a colorant, a fabric conditioner, a conditioning substrate, a pharmaceutical, a crop protection product, a polish, a food, a cosmetic product, a fertilizer, a building material, an adhesive, a bleach, a decalcifier, floorcare product, cookercare product, leathercare product or furniture care product, a scourer, a disinfectant, a fragrancer, a mould remover and / or a precursor of the aforementioned products.

[0072] The consumer product may be a cleaning product, such as:

[0073] Toilet cleaners or lavatory cleaners, in other words, products for cleaning lavatory bowls and urinals, these products being supplied preferably in the form of powders, blocks, tablets or liquids, preferably gels. Besides other typical ingredients such as surfactants, they generally include organic acids e.g., citric acid and / or lactic acid) or sodium hydrogen sulfate, amidosulfuric acid or phosphoric acid for removing limescale or urine scale;

[0074] Pipe-cleaning products or drain cleaners. These are typically strongly alkaline products which serve in general to remove pipe blockages comprising organic materials-such as hair, fat, food residues, soap deposits, and the like. Additions of Al powder or Zn powder may serve for the formation of H2 gas with an effervescence effect. Possible ingredients are commonly alkalis, alkaline salts, oxidizing agents, and neutral salts. Supply forms in powder form preferably also include sodium nitrate and sodium chloride. Pipe-cleaning products in liquid form may preferably also include hypochlorite. There are also enzyme-based drain cleaners as well. Acidic products are likewise possible;

[0075] Universal or all-purpose or general-purpose cleaners. These are cleaners which can be used universally for all hard surfaces in the household and in commerce that can be wiped down wet or damp. Generally speaking, they are neutral or slightly alkaline or slightly acidic products, especially liquid products. All-purpose or general-purpose cleaners generally contain surfactants, builders, solvents and hydrotropes, dyes, preservatives, and the like; All-purpose cleaners with special disinfectant properties. They additionally include active antimicrobial ingredients (e.g., aldehydes, alcohols, quaternary ammonium compounds, amphoteric surfactants, triclosan);

[0076] Sanitary cleaners. These are products for cleaning in bath and toilet. The alkaline sanitary cleaners are used preferably for removing fatty soiling, whereas the acidic sanitary cleaners are employed in particular, for removing limescale. Sanitary cleaners advantageously also have a considerable disinfectant action, particularly the strongly alkaline sanitary cleaners that contain chlorine;

[0077] Oven cleaners or grill cleaners which may be supplied in the form of gels or foam sprays. They generally serve for removing burnt-on or carbonized food residues. Oven cleaners are preferably given a strongly alkaline formulation using, for example, sodium hydroxide, sodium metasilicate, 2- aminoethanol. In addition, they generally contain anionic and / or nonionic surfactants, water-soluble solvents, and, in some cases, thickeners such as polycarboxylates and carboxymethylcellulose; Glass cleaners and window cleaners. These products serve preferably to remove dirt, especially greasy dirt, from glass surfaces. Preferably they contain compounds such as anionic and / or nonionic surfactants (in particular, up to 5% by weight), ammonia and / or ethanolamine (in particular, up to 1 % by weight), ethanol and / or 2-propanol, glycol ethers (in particular, 10-30% by weight), water, preservatives, dyes, anti-misting agents and the like; and

[0078] The consumer product may be a cosmetic product, for example (a) cosmetic skincare products, especially bath products, skin washing and cleansing products, skincare products, eye makeup, lip care products, nail care products, intimate care products, foot care products; or (b) cosmetic products with specific effects, especially sunscreens, tanning products, de-pigmenting products, deodorants, antiperspirants, hair removers, shaving products, perfumes; (c) cosmetic dental-care products, especially dental and oral care products, tooth care products, cleaners for dental prostheses, adhesives for dental prostheses; or (c) cosmetic hair care products, especially hair shampoos, hair care products, hair setting products, hair-shaping products, and hair colouring products.

[0079] The invention is now further described with reference to the following non-limiting examples. Variations and modifications as will be readily apparent to those skilled in the art are intended to be within the scope of the present invention as defined in and by the appended claims.

[0080] The invention will be further illustrated by reference to the following examples.

[0081] Kinetic Resolution for the Preparation of (□)-(E)-1-((1 S,2R)-2,6,6-Trimethylcyclohex-3-en-1-yl) but-2- en-1-one (compound of formula (I))

[0082] A three neck round bottom flask under inert atmosphere was charged with cupric chloride dihydrate (144 mg, 0.05 Eq, 845 pmol), (S)-DTBM-SEGPHOS (997 mg, 0.05 Eq, 845 pmol) and sodium te / Y-butoxide (325 mg, 0.20 Eq, 3.38 mmol). PMHS (8.57 g, 8.52 mL, 2.00 Eq, 33.8 mmol) and toluene (14.0 mL) were added via syringe and the mixture stirred for 30 minutes at room temperature. Pentane (28 mL) was added and the mixture cooled to around -15 °C. Then, a solution of racemic (E)-1 -(2,6,6- trimethylcyclohex-3-en-1-yl) but-2-en-1-one (3.25 g, 1 .00 Eq, 16.9 mmol) dissolved in toluene (14.0 mL) was added, followed by tert-pentyl alcohol (2.98 g, 3.70 mL, 2.00 Eq, 33.8 mmol). The mixture was stirred for 15 minutes at -15 °C, then poured onto a 2 M aq. HCI solution and stirred until the green colour changed to a bright violet (ca. 1.5 min). The aqueous phase was extracted with MTBE (3 x 20 mL). The combined organic phase washed with water (150 mL), and brine (150 mL), dried over anhydrous sodium sulfate and suction filtered. The filtrate was concentrated under reduced pressure to afford the crude product, which was first purified by flash column chromatography using 3% MTBE in heptane as eluent, then distilled to afford (-)-(E)-1-((1S,2R)-2,6,6-Trimethylcyclohex-3-en-1-yl) but-2- en-1-one as colourless crystals (500 mg, 2.60 mmol, 78% ee, 15.4% yield).

[0083] If the enantiomeric excess was not in the range of 80% or above, a recrystallization step was carried out as follows:

[0084] The main fraction collected by bulb to bulb distillation was carefully set aside to slowly reach room temperature. A good quality seeding crystal of enantiopure Delta-Damascone was added to the liquid product to initiate crystallisation. After two hours, the bulb was carefully turned so that the crystals were hanging upside down and the supernatant was able to slowly rinse to the bottom of the bulb. If no further crystal formation was observed, the supernatant was pipetted out of the bulb.

[0085] The tonality of the odour was assessed by a skilled panelist in a 1% ethanolic solution on a paper blotter. Odour description: fruity, sweet, apple, delta damascone like, diffusive, fresh, minty.

[0086] Example 2

[0087] Kinetic Resolution for the Preparation of (□)-(E)-1-((1S,2R)-2,6,6-Trimethylcyclohex-3-en-1-yl) but-2- en-1-one and 1-((1 R,2S)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one mixtures (mixture of compound of formula (I) and (III))

[0088] A three neck round bottom flask under inert atmosphere was charged with cupric chloride dihydrate (144 mg, 0.05 Eq, 845 pmol), (S)-DTBM-SEGPHOS (997 mg, 0.05 Eq, 845 pmol) and sodium tert- butoxide (325 mg, 0.20 Eq, 3.38 mmol). PMHS (8.57 g, 8.52 mL, 2.00 Eq, 33.8 mmol) and toluene (14.0 mL) were added via syringe and the mixture was stirred for 30 minutes at room temperature. Pentane (28 mL) was added, and the mixture was cooled to around -15 °C. Then, a solution of racemic E)-1-(2,6,6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one (3.25 g, 1.00 Eq, 16.9 mmol) in toluene (14.0 mL) was added, followed by tert-pentyl alcohol (2.98 g, 3.70 mL, 2.00 Eq, 33.8 mmol). The mixture stirred for 3.5 minutes at -15 °C. The mixture was then directly poured onto a 2 M aq. HCI solution and stirred until the green colour changed to a bright violet (ca. 1 .5 min). The aqueous phase was extracted with MTBE (3 x 25 mL). The combined organic phase was washed with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate and suction filtered. The filtrate was concentrated under reduced pressure to afford the crude (-)-(E)-1-((1S,2R)-2,6,6-Trimethylcyclohex- 3-en-1-yl) but-2-en-1-one as a violet oil which still contained PMHS. The crude product was distilled through a vigreux distillation apparatus to give a mixture of (-)-(E)-1-((1S,2R)-2,6,6-Trimethylcyclohex- 3-en-1 -yl) but-2-en-1-one (46%, 65%ee) and 1-((1 R,2S)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one (54%, 23% ee) in 17% yield (2.7 g).

[0089] The tonality of the odour of the mixture was assessed by a skilled panelist in a 1 % ethanolic solution on a paper blotter. Odour description: fruity, sweet, delta damascone like, diffusive, fresh, minty.

[0090] Example 3

[0091] Biodegradation Study

[0092] The method is based on No. 301 F in the OECD Guidelines for Testing of Chemicals.

[0093] A measured volume of inoculated mineral medium, containing a known concentration of test substance as the nominal sole source of organic carbon, is stirred in a closed flask at a constant temperature for up to 60 days. Evolved carbon dioxide is absorbed in sodium hydroxide pellets. The consumption of oxygen is determined by measuring the pressure drop in the respirometer flask. The Biological Oxygen Demand (BOD), amount of oxygen taken up by the microbial population during biodegradation of the test chemical (corrected for uptake by blank inoculum, run in parallel) is expressed as a percentage of ThOD (Theoretical Oxygen Demand, calculated from the elemental composition, assuming that carbon is oxidized to carbon dioxide, hydrogen to water and nitrogen to ammonium, nitrite or nitrate).

[0094] Fresh activated sludge from a biological waste water treatment plant treating predominantly domestic sewage (Bois-de-Bay, Satigny, Switzerland) was used. The sludge was collected in the morning, washed three times in the mineral medium (by centrifuging at 1000 g for 10 minutes, discarding the supernatant and re-suspending it in mineral medium) and kept aerobic until being used on the same day. The dry weight of suspended solids is determined by taking two 50 mL samples of the homogenised sludge, evaporating water on a steam bath, drying in an oven at 105 - 110°C for two hours and weighing the residue. The respirometer used during this study is an Oxitop Control System, made by Wissenschaftlich-Technische Werkstatten (WTW), Weilheim, Germany. Test flasks are filled with 250 mL of mineral medium. Test substance samples (7.6 mg, corresponding to 30.0 mg / L in 255 mL of test medium) are weighed in small aluminium boats and added directly to the test flasks of the Oxitop system. Then 5.00 ml of suspended sludge diluted to a concentration of 1 .53 g / l dry matter is added. Two sodium hydroxide pellets are placed in the quivers on top of the bottle, and the flasks are closed tightly with the Oxitop measuring heads. The flasks are allowed to equilibrate to the test temperature (22 ± 1 °C). The measurement is started by programming the measuring unit of the Oxitop test flasks, and the test flasks are placed in the temperature controlled cupboard of the Oxitop system. After temperature equilibration, the controller of the instrument starts the data acquisition (time zero of the experiment). Every day the oxygen consumption of each flask is recorded and correct temperature and stirring are checked. Results are shown in Figure 1 , clearly demonstrating that whereas the compound of formula (I) is biodegradable, both the racemic mixture and the enantiomer of the compound of formula (I) are not.

[0095] A library of all human class II olfactory receptors was screened for activation by b-damascone. OR8K3, previously described as a receptor for menthol, was the only OR found to be strongly activated by b-damascone. Dose response assays showed that b-damascone, p-damascone and damascenone were at least a 100-fold more potent ligands for OR8K3 than menthol suggesting that this OR plays a crucial role in the perception of the typical odor of b-damascone.

[0096] To create the expression plasmid for human OR8K3, the gene coding for OR8K3 with an optimized C- terminus (DNA sequence SEQ ID NO: 1 DNA and amino acid sequence SEQ ID NO: 2) was synthesized by a DNA synthesis service provider (BioCat GmbH, Germany) and inserted into pcDNA3.1 (+) using BamHI and Notl restriction sites (Invitrogen, MA, USA) downstream of the CMV promoter sequence (SEQ ID NO: 3) and before the bgh terminator sequence (SEQ ID NO: 4). The synthetic OR8K3 nucleotide sequence further contained at its 3’-end a nucleotide sequence encoding a signal peptide (mmLucy-FLAG-rho) (SEQ ID NO: 5 and 6). This plasmid thus contains a constitutively expressed OR gene.

[0097] Expression of the OR8K3 genes was performed in HEK293T cells that had been stably transfected with a DNA sequence coding for functional variants of the human RTP1 S (V227I, SEQ ID NO: 7 and 8) and RTP2 (L220R, SEQ ID NO: 9 and 10). These cells were seeded into polyethyleneimine coated 96-well plates (1 OOpl / well) at a density of 10,000 cells / well and grown at 37°C in presence of 5% CO2 for 24 h .

[0098] 0.625 pg of the OR8K3 expression plasmid, 1 pg of the empty pcDNA3.1 (+) vector and 1 pg of pGL4.29 (Promega) harbouring the CRE-inducible luciferase were diluted in 0.25 ml OptiMEM medium (GibcoTM, ThermoFisher Scientific, MA, USA). In parallel 15 pl Lipofectamine 2000 (Invitrogen) were diluted in 0.25 ml OptiMEM medium and after 5 min pre-incubation, the two mixtures were combined to prepare the transfection mixture, which was incubated for an additional 25 min.

[0099] 50 pl of growth medium was replaced with fresh DMEM containing 9% foetal bovine serum (FBS). The pre-incubated transfection mixture was diluted to 5.5 ml in OptiMEM medium and 50 pl of the diluted mixture was added per well (final total volume is 150 pl). Cells were further incubated for 24 h at 37°C in presence of 5% CO2 to allow for DNA uptake and expression of OR8K3.

[0100] Activation of OR8K3 by racemic b-Damascone, compound of formula (I) and (II), p-Damascone and menthol was measured by removal of 100 pl growth medium and addition of 50 pl DMEM containing 9% FBS, 1 % DMSO, and different concentrations of the test substances. After incubation for 4.5 h, the cells were lysed using 20 pl passive lysis buffer (Promega) and the luciferase signal, which is induced based on OR-dependent cAMP production, was measured.

[0101] Potency of the tested OR8K3 ligands is expressed as the EC20% and the EC50% value, which is the concentration that leads to a 20 % or 50% increase of the luciferase activity relative to the maximal activation of the positive control. Racemic 6-damascone has an EC20% value of 0.33 pM while compound of formula (I) has an EC20% value of 0.16 pM. The compound of formula (II) on the other hand has an EC20% value of 7.62 pM, and its potency on OR8K3 therefore is 48-fold lower as compared to the compound of formula (I). Similarly, racemic 6-damascone has an EC50% value of 1.14 pM while compound of formula (I) has an EC50% value of 0.58 pM. The compound of formula (II) on the other hand has an EC50% value of 41 .05 pM, and its potency on OR8K3 expressed by the EC50% value therefore is 71 -fold lower as compared to compound of formula (I). Because of these differences, a much lower concentration of compound of formula (I) is needed to activate the receptor compared to the concentration needed of for the compound of formula (II).

[0102] Also, because compound of formula (I) is twice as active as compared to the racemate, one can conclude that all the effect of the racemic mixture on OR8K3 is due to its content of compound of formula (I).

[0103] Figure 2 show the response of these test compounds graphically.

[0104] Sequences:

[0105] OR8K3 DNA sequence with an optimized C-terminus DNA sequence (SEQ ID NO 1):

[0106] ATGGAACAACACAATCTAACAACGGTGAATGAATTCATTCTTACGGGAATCACAGATATCGCTGAG

[0107] CTGCAGGCACCATTATTTGCATTGTTCCTCATGATCTATGTGATCTCAGTGATGGGCAATTTGGGC ATGATT

[0108] GTCCTCACCAAGTTGGACTCCAGGTTGCAAACCCCTATGTACTTTTTTCTCAGACATCTG

[0109] GCTTTCATGGATCTTGGTTATTCAACAACTGTGGGACCCAAAATGTTAGTAAATTTTGTT

[0110] GTGGATAAGAATATAATTTCTTATTATTTTTGTGCAACACAGCTAGCTTTCTTTCTTGTG

[0111] TTCATTGGTAGTGAACTTTTTATTCTCTCAGCCATGTCCTACGACCGCTATGTGGCCATC

[0112] TGTAACCCTCTGCTATACACAGTAATCATGTCACGAAGGGTATGTCAGGTGCTGGTAGCA

[0113] ATCCCTTACCTCTATTGCACATTCATTTCTCTTCTAGTCACCATAAAGATTTTTACTTTA

[0114] TCCTTCTGTGGCTACAACGTCATTAGTCATTTCTACTGTGACAGTCTCCCTTTGTTACCT

[0115] TTGCTTTGTTCAAATACACATGAAATTGAATTGATAATTCTGATCTTTGCAGCTATTGAT

[0116] TTGATTTCATCTCTTCTGATAGTTCTTTTATCTTACCTGCTCATCCTTGTAGCCATTCTC

[0117] AGGATGAATTCTGCTGGCAGACAAAAGGCTTTTTCTACCTGTGGAGCCCACCTGACAGTG

[0118] GTCATAGTGTTCTATGGGACTTTGCTTTTCATGTACGTGCAGCCCAAGTCCAGTCATTCC

[0119] TTTGACACTGATAAAGTGGCTTCCATATTTTACACCCTGGTTATCCCCATGTTGAATCCC

[0120] TTGATCTATAGTTTAAGGAACAAAGAAGTTAAAAAGGCCATAAAGAGGTTGTTCAAGAGA

[0121] AAGTGCTGCAGGAGAAGGTGAGCGGCCGC

[0122] OR8K3 amino acid sequence with an optimized C-terminus amino acid sequence (SEQ ID NO 2):

[0123] MEQHNLTTVNEFILTGITDIAELQAPLFALFLMIYVISVMGNLGMIVLTKLDSRLQTPMYFFLRHLAFMD LGYSTTVGPKMLVNFWDKNIISYYFCATQLAFFLVFIGSELFILSAMSYDRYVAICNPL LYTVIMSRRVCQVLVAIPYLYCTFISLLVTIKIFTLSFCGYNVISHFYCDSLPLLPLLCS

[0124] NTHEIELIILIFAAIDLISSLLIVLLSYLLILVAILRMNSAGRQKAFSTCGAHLTVVIVF

[0125] YGTLLFMYVQPKSSHSFDTDKVASIFYTLVIPMLNPLIYSLRNKEVKKAIKRLFKRKCCRRR CMV Promoter DNA sequence (SEQ ID NO 3)

[0126] GTTGACATTGATTATTGACTAGTTATTAATAGTAATCAATTACGGGGTCATTAGTTCATA

[0127] GCCCATATATGGAGTTCCGCGTTACATAACTTACGGTAAATGGCCCGCCTGGCTGACCGCCCAA

[0128] CGACCCCCGCCCATTGACGTCAATAATGACGTATGTTCCCATAGTAACGCCAATAGGGACTTTCC

[0129] ATTGACGTCAATGGGTGGAGTATTTACGGTAAACTGCCCACTTGGCAGTACATCAAGTGTATCAT

[0130] ATGCCAAGTACGCCCCCTATTGACGTCAATGACGGTAAATGGCCCGCCTGGCATTATGCCCAGTA

[0131] CATGACCTTATGGGACTTTCCTACTTGGCAGTACATCTACGTATTAGTCATCGCTATTACCATGGT

[0132] GATGCGGTTTTGGCAGTACATCAATGGGCGTGGATAGCGGTTTGACTCACGGGGATTTCCAAGT

[0133] CTCCACCCCATTGACGTCAATGGGAGTTTGTTTTGGCACCAAAATCAACGGGACTTTCCAAAATG

[0134] TCGTAACAACTCCGCCCCATTGACGCAAATGGGCGGTAGGCGTGTACGGTGGGAGGTCTATATA AGCAGAGCTC bgh terminator DNA sequence (SEQ ID NO 4)

[0135] CTGTGCCTTCTAGTTGCCAGCCATCTGTTGTTTGCCCCTCCCCCGTGCCTTCCTTGACCCTGGAA

[0136] GGTGCCACTCCCACTGTCCTTTCCTAATAAAATGAGGAAATTGCATCGCATTGTCTGAGTAGGTG

[0137] TCATTCTATTCTGGGGGGTGGGGTGGGGCAGGACAGCAAGGGGGAGGATTGGGAAGACAATAG CAGGCATGCTGGGGATGCGGTGGGCTCTATGG mmLucy-FLAG-rho DNA sequence (SEQ ID NO 5)

[0138] ATGAGCCACCAGATCCTGCTGCTCCTGGCCCTGCTGACCCTAGGCCTGGCTGATTACAAGGACG ACGACGATAAGATCGAATTGATGAACGGGACCGAGGGCCCAAACTTCTACGTGCCTTTCTCCAAC AAGACGGGCGTGGTGGAATTC mmLucy-FLAG-rho amino acid sequence (SEQ ID NO 6)

[0139] MSHQILLLLALLTLGLAMDYKDDDDKMNGTEGPNFYVPFSNKTGWEF

[0140] RTP1 S(V227I) DNA sequence (SEQ ID NO 7)

[0141] ATGTGTAAAAGCGTGACCACAGATGAGTGGAAGAAAGTCTTCTATGAGAAGATGGAGGAGGCAA AGCCGGCTGACAGCTGGGACCTCATCATAGACCCCAACCTCAAGCACAATGTGCTGAGCCCTGG TTGGAAGCAGTACCTGGAATTGCATGCTTCAGGCAGGTTCCACTGCTCCTGGTGCTGGCACACC TGGCAGTCGCCCTACGTGGTCATCCTCTTCCACATGTTCCTGGACCGCGCCCAGCGGGCGGGCT CGGTGCGCATGCGCGTCTTCAAGCAGCTGTGCTATGAGTGCGGCACGGCGCGGCTGGACGAGT CCAG CATG CTG GAG G AG AAC ATCG AG GG CCTG GTG G ACAACCTCATCACCAGCCTGCG CG AGO AGTGCTACGGCGAGCGTGGCGGCCAGTACCGCATCCACGTGGCCAGCCGCCAGGACAACCGG

[0142] CGGCACCGCGGAGAGTTCTGCGAGGCCTGCCAGGAGGGCATCGTGCACTGGAAGCCCAGCGA GAAGCTGCTGGAGGAGGAGGCGACCACCTACACCTTCTCCCGGGCGCCCAGCCCCACCAAGTC GCAGGACCAGACGGGCTCAGGCTGGAACTTCTGCTCTATCCCCTGGTGCTTGTTTTGGGCCACG GTCCTG CTG CTG ATCATCTACCTG CAGTTCTCTTTCCGTAG CTCCATCTAA RTP1S(V227I) amino acid sequence (SEQ ID NO 8)

[0143] MCKSVTTDEWKKVFYEKMEEAKPADSWDLIIDPNLKHNVLSPGWKQYLELHASGRFHCSW

[0144] CWHTWQSPYVVILFHMFLDRAQRAGSVRMRVFKQLCYECGTARLDESSMLEENIEGLVDN

[0145] LITSLREQCYGERGGQYRIHVASRQDNRRHRGEFCEACQEGIVHWKPSEKLLEEEATTYT

[0146] FSRAPSPTKSQDQTGSGWNFCSIPWCLFWATVLLLIIYLQFSFRSSI

[0147] RTP2(L220R) DNA sequence (SEQ ID NO 9)

[0148] ATGTGTACCAGCTTGACCACTTGTGAGTGGAAGAAAGTCTTCTATGAGAAGATGGAGGTGGCAAA

[0149] GCCAGCGGACAGCTGGGAGCTCATCATAGACCCCAACCTCAAGCCCAGTGAGCTGGCCCCTGG

[0150] CTGGAAGCAGTACCTGGAGCAGCACGCCTCAGGCAGGTTCCACTGCTCCTGGTGCTGGCACAC

[0151] CTGGCAGTCTGCCCATGTGGTCATCCTCTTCCACATGTTCCTGGACCGCGCCCAGCGGGCGGGC

[0152] TCGGTGCGCATGCGCGTCTTCAAGCAGCTGTGCTATGAGTGCGGCACGGCGCGGCTGGACGAG

[0153] TCCAGCATGCTGGAGGAGAACATCGAGGGCCTGGTGGACAACCTCATCACCAGCCTGCGCGAG

[0154] CAGTGCTACGAGGAGGATGGTGGCCAGTACCGCATCCACGTGGCCAGCCGCCCGGACAGCGG

[0155] GCCGCATCGTGCAGAGTTCTGTGAGGCCTGCCAGGAGGGCATCGTTCACTGGAAGCCCAGCGA

[0156] GAAGCTGCTGGAGGAGGAGGTGACCACCTACACCTCTGAAGCCTCCAAGCCGAGGGCCCAGGC

[0157] GGGATCCGGCTACAACTTCTTGTCTCTTCGCTGGTGCCTCTTCTGGGCCTCTCTCTGCCTGCTCG

[0158] TTGTTTACCTGCAGTTCTCCTTCCGCAGTCCTGCCTTCTTTTAG

[0159] RTP2(L220R) amino acid sequence (SEQ ID NO 10)

[0160] MCTSLTTCEWKKVFYEKMEVAKPADSWELIIDPNLKPSELAPGWKQYLEQHASGRFHCSW

[0161] CWHTWQSAHWILFHMFLDRAQRAGSVRMRVFKQLCYECGTARLDESSMLEENIEGLVDN

[0162] LITSLREQCYEEDGGQYRIHVASRPDSGPHRAEFCEACQEGIVHWKPSEKLLEEEVTTYT

[0163] SEASKPRAQAGSGYNFLSLRWCLFWASLCLLWYLQFSFRSPAFF

Claims

Claims:

1. (-)-(E)-1-((1S,2R)-2,6,6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one, according to the formula(I)2. A perfume mixture comprising the compound according to formula (I).

3. A perfume mixture according to claim 2, comprising a scalemic mixture of the compound of formula (I) and the compound of formula (II), wherein the compound of formula (I) is present in an enantiomeric excess.

4. A perfume mixture according to claim 2 or claim 3, wherein the enantiomeric excess is 20 % ee or greater.

5. A perfume mixture according to any of the claims 2 to 4, wherein the enantiomeric excess is 70 % or greater.

6. A perfume mixture according to any of the claim 2, wherein the compound of formula (I) is in enantiopure form.

7. A perfume mixture according to any of the claims 2 to 6, comprising the compound 1-((1 R,2S)- 2,6,6-trimethylcyclohex-3-en-1-yl) butan-1-one according to formula (III) in enantiopure form, or in scalemic or racemic mixture.

8. A perfume mixture according to any of the claims 2 to 7 comprising at least one additional perfume ingredient.

9. A consumer product comprising a compound according to claim 1 or a perfume mixture according to any of the claims 2 to 8.

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