USE OF AMBROCENIDE® TO ENHANCE A LILY OF THE VALLEY NOTE

Description

[0001] The present invention primarily relates to the use of one or more stereoisomer(s) of the compound of formula (I) as described herein for modifying and / or enhancing the olfactory impression of one or more odorants having a lily of the valley note, wherein the odorant(s) is / are selected from the group consisting of 7-hydroxy-3,7-dimethyloctanal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, 2,2-dimethyl-3-(3-methylphenyl)propanol, cis-4-(1-methylethyl)cyclohexanemethanol, 1-(4-isopropylcyclohexyl)ethanol, 3-methyl-4-phenylbutan-2-ol, dimethylphenylpropanol, and compound of formula (II) as described herein.The invention further relates to a novel mixture comprising or consisting of one or more stereoisomer(s) of the compound of formula (I) as described herein and two or more stereoisomers of the compound of formula (II) as described herein with a weight ratio of the stereoisomers of the compounds of formula (II) as described herein, fragrance compositions comprising or consisting of a mixture as described herein, perfumed products containing mixtures or fragrance compositions as described herein and a process for modifying and / or enhancing the lily of the valley note of a compound of formula (II) as described herein or for producing a perfumed product as described herein.

[0002] Further aspects and preferred embodiments of the present invention will become apparent from the following explanations, the attached examples and in particular the attached patent claims.

[0003] Despite the multitude of existing fragrances, there is still a general need for new fragrances and fragrance compositions in the perfume industry. For example, there is a need for fragrances that are capable of creating additional interesting notes (in fragrance compositions) alongside a primary fragrance note, expanding the perfumer's options with their novel or original olfactory properties. There is particular interest in fragrances with notes that are capable of harmoniously combining with floral and / or fruity fragrances. The preferred approach is to layer the different olfactory aspects and notes to create an overall complex olfactory impression.

[0004] In this context, WO 2015 / 176833 A1 discloses a mixture containing or at least essentially consisting of (alpha,alpha-(4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole) and (beta,beta-(4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole), a process for producing such a mixture, novel fragrance and / or aroma compositions and the use of the mixture (a) for masking or reducing the or one or more unpleasant odor impressions of one or more unpleasant-smelling substances, and / or (b) for enhancing the or one or more pleasant olfactory impressions of one or more pleasant-smelling substances.

[0005] Furthermore, EP 0 857 723 A1 discloses cyclic cedrene acetals, their preparation and their use as fragrances or components of fragrance mixtures or perfume oils for perfuming cosmetic or technical consumer goods.

[0006] Panten et al., in "New woody and ambery notes from cedarwood and turpentine oil," Chemistry & Biodiversity, Helvetica Chimica Acta, Zurich (CH), Vol. 1, No. 12, December 1, 2004, pages 1936-1948 (DOI: 10.1002 / CBDV.200490148), disclose the applicability of longifolene and cedrene for the synthesis of woody and ambery notes and their structural and sensory aspects.

[0007] WO 2014 / 180945 A1 discloses 3-(4-isobutyl-2-methylphenyl)propanal as a perfume ingredient with the fragrance note lily of the valley, as well as mixtures thereof and their preparation.

[0008] US 8 754 028 B2 discloses a perfume which is free from p-tert.butyl-alpha-methyldihydrocinnamaldehyde and consumer products comprising said perfume.

[0009] Furthermore, WO 2012 / 062771 A1 discloses a fragrance composition comprising specific mixtures of diastereomers of 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol, their production processes and products comprising said fragrance composition.

[0010] Finally, WO 2011 / 147919 A1 discloses a process for preparing 2-substituted 4-hydroxy-4-methyltetrahydropyrans by reacting 3-methylbut-3-en-1-ol (isoprenol) with the corresponding alkene aldehydes in the presence of a strongly acidic ion exchanger, followed by hydrogenation. Specifically, the publication in question relates to a corresponding process for preparing 2-isobutyl-4-hydroxy-4-methyltetrahydropyran by reacting isoprenol with prenal, followed by hydrogenation.

[0011] For the creation of novel compositions, there is a constant need for fragrances with special sensory properties that are suitable to serve as a basis for the composition of novel perfumes with complex sensory character.

[0012] The primary task was to find fragrances that exhibit an interesting, preferably complex, and original sensory profile and are suitable for use in, for example, perfumery. Within the scope of the present invention, we were particularly looking for substances that can modify and / or enhance a lily-of-the-valley scent.

[0013] The sought-after substances should enable the creation of novel fragrance compositions with distinctive olfactory notes and aspects. Advantageous would be those substances that are particularly suitable for combination with other fragrances that contain the lily-of-the-valley note.

[0014] In addition, the fragrances fulfilling this primary task should preferably have additional positive secondary properties beyond their primary, namely olfactory, properties, such as high stability under certain application conditions, high efficiency, good adhesion, high substantivity or odor-enhancing properties (so-called booster or enhancer effect), and / or in combination with other fragrances round off their naturalness, freshness, fullness, (radiance) power and / or charisma, so that sensorially remarkable effects can be achieved.

[0015] According to the invention, the primary object is achieved by the use of one or more stereoisomer(s) of the compound of formula (I) for modifying and / or enhancing, preferably for enhancing, the olfactory impression of one or more odorous substances with a lily of the valley note, wherein the odorous substance(s) is / are selected from the group consisting of 7-hydroxy-3,7-dimethyloctanal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, 2,2-dimethyl-3-(3-methylphenyl)propanol, cis-4-(1-methylethyl)cyclohexanemethanol, 1-(4-isopropylcyclohexyl)ethanol, 3-methyl-4-phenylbutan-2-ol, dimethylphenylpropanol and compound of formula (II), preferably wherein the odorant is a compound of formula (II).

[0016] In the context of the study underlying the present invention, it has surprisingly been shown that the compound of formula (I) (Ambrocenide ®< , CAS No.: 211299-54-6) is excellently suited to modifying and / or intensifying, in particular to intensify, the lily of the valley note of various lily of the valley fragrances.

[0017] According to the present invention, one, two, three or all of the following diastereomers (Ia) to (Id) can be used as the compound of formula (I), ie the individual diastereomers (Ia) to (Id) can be used or any desired mixture of these diastereomers.

[0018] What has been said herein for a compound of formula (I), in particular the advantages described herein, also applies to the individual diastereomers (Ia) to (Id) and any mixture of these diastereomers (see above).

[0019] Particularly preferred is a use as described herein, wherein the odorant or one of the odorants comprises or consists of two or more stereoisomers of the compound of formula (II) wherein preferably the weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(-) between 65 : 35 and 95 : 5, preferably 70 : 30 and 90 : 10, particularly preferably 75 : 25 and 85 : 15.

[0020] The inventive use of the compound of formula (II) as described herein with an isomer ratio in the above-defined range is particularly preferred within the scope of the present invention. The compound of formula (II) as described herein with an isomer ratio in the above-defined range is known, for example, under the trade name Pyranol. Pyranol is relatively volatile and has a soft floral scent with a typical note of lily of the valley (lily of the valley, muguet), which, according to the present invention, surprisingly appears more natural and radiant through the addition of one or more stereoisomer(s) of the compound of formula (I). Furthermore, the lily of the valley scent of pyranol becomes more pronounced (boost effect) through the addition of one or more stereoisomer(s) of the compound of formula (I), and the substantivity is increased.

[0021] Some isomer mixtures of the compound of formula (II), for example Florol ® / Florosa ®, are sometimes perceived as too expensive. Other isomer mixtures, such as pyranol, are sometimes perceived as having less character, less radiance, and / or less fragrance stickiness compared to other isomer mixtures of the compound of formula (II) in terms of their olfactory properties. Surprisingly, the addition of one or more stereoisomers of the compound of formula (I) leads to a sensory enhancement (see examples below), i.e., more character, more radiance, and / or greater fragrance stickiness.

[0022] Another advantage of using compounds of formula (II) over other odorous substances with a lily of the valley note (such as those listed above) is that the compounds of formula (II) are less burdened by regulations (more harmless classification / labeling) and have a better cost-performance ratio.

[0023] According to one embodiment of the use according to the invention, it is preferred if the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) predominantly - ie more than 50% by weight based on the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) - comprises compound of the formula cis-(II)(-), preferably if it comprises 60, 70, 80 or 90% by weight of compound of the formula cis-(II)(-), or if it consists essentially, preferably 100% by weight based on the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-), of compound of the formula cis-(II)(-).

[0024] According to one embodiment of the use according to the invention, it is preferred if the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) predominantly - ie more than 50% by weight based on the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) - comprises compound of the formula cis-(II)(+), preferably if it comprises 60, 70, 80 or 90% by weight of compound of the formula cis-(II)(+), or if it consists essentially, preferably 100% by weight based on the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-), of compound of the formula cis-(II)(+).

[0025] According to a further aspect, the present invention therefore also relates to a mixture comprising or consisting of one or more stereoisomer(s) of the compound of formula (I) and two or more stereoisomers of the compound of formula (II) where the weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(-) between 65 : 35 and 95 : 5, preferably 70 : 30 and 90 : 10, particularly preferably 75 : 25 and 85 : 15.

[0026] Preference is given to a mixture as described herein, wherein the weight ratio of the total amount of stereoisomer(s) of the compound of formula (I) to the total amount of stereoisomers of the compound of formula (II) between 1:12000 and 1:0.5, preferably between 1:600 ​​and 1:0.7, particularly preferably between 1:100 and 1:1, and / or wherein the total amount of stereoisomer(s) of the compound of formula (I) is sufficient to modify and / or intensify, preferably to intensify, the olfactory impression of the two or more stereoisomers of the compound of formula (II).

[0027] According to a further aspect, the present invention also relates to a process for modifying and / or enhancing, preferably for enhancing, the lily of the valley note of a compound of formula (II), comprising or consisting of the following steps: i) Providing one or more stereoisomers of the compound of formula (I) ii) providing two or more stereoisomers of the compound of formula (II) where the weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(-) between 65:35 and 95:5, preferably 70:30 and 90:10, particularly preferably 75:25 and 85:15, iii) mixing the compounds provided in steps i) and ii), preferably wherein the amount of the one or more stereoisomers of the compound of formula (I) is sufficient to modify and / or enhance, preferably to enhance, the lily of the valley note of the compound of formula (II).

[0028] Preferred is a process according to the invention as described herein, wherein the weight ratio of the total amount of stereoisomer(s) of the compound of formula (I) to the total amount of stereoisomers of the compound of formula (II) between 1 : 12000 and 1 : 0.5, preferably between 1 : 600 and 1 : 0.7, particularly preferably between 1 : 10 and 1 : 1.

[0029] Also generally described herein is a mixture producible by a process comprising or consisting of the following steps: i) Providing one or more stereoisomers of the compound of formula (I) ii) providing two or more stereoisomers of the compound of formula (II) where the weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(-) between 65 : 35 and 95 : 5, preferably 70 : 30 and 90 : 10, particularly preferably 75 : 25 and 85 : 15, iii) mixing the compounds provided in steps i) and ii).

[0030] According to a further aspect, the present invention also relates to a fragrance composition, preferably perfume oil, comprising or consisting of a mixture as described herein and preferably also one or more additional fragrances,

[0031] preferably wherein the additional or one, several or all of the additional fragrances is or are selected from the group consisting of 3-(4-methyl-1-cyclohex-3-enyl)-butanal, 4-(4-hydroxyphenyl) butan-2-one, (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one, (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one, (E)-1-(2,6,6-trimethyl-cyclohexen-1-yl)pent-1-en-3-one, (E)-4-[(1S)-1,2,6,6-tetramethylcyclohex-2-en-1-yl]-but-3-en-2-one, 1-(2,6,6-Trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one, [(Z)-Hex-3-enyl] methyl carbonate, 3-[(Z)-Hex-3-enoxy]propane nitrile, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexa-hydronaphthalen-2-yl)ethanone, spiro[1,3-dioxolane-2,5'-(4',4',8',8'-tetramethyl-hexahydro-3',9'-methanonaphthalene)], [3R-(3α,3aβ,6β,7β,8aα)]-octa-hydro-6-methoxy-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene,[3R-(3α,3aβ,7β,8aα)] - 1-(2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methano-azulen-5-yl) ethan-1-one, 1-(2,2,6-trimethylcyclohexyl) hexan-3-ol, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, 2,6-dimethyloct-7-en-2-ol, 3,7-dimethylocta-1,6-dien-3-ol, (3,7-dimethylocta-1,6-dien-3-yl) acetate, (4-methyl-1-propan-2-yl-1-cyclohex-2-enyl) acetate, (8E)-Cyclohexadec-8-en-1-one, 16-oxacyclohexa-decan-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, ethoxymethoxy-cyclododecane, 1,1,2,3,3-pentamethyl-2,5,6,7-tetrahydroinden-4-one, 1-(2,3,8,8-Tetramethyl-1,3,4,5,6,7-hexa-hydronaphthalen-2-yl)ethanone.,

[0032] A fragrance composition as described herein is preferred, wherein the total amount of stereoisomer(s) of the compound of formula (I) sufficient to produce the olfactory impression of the two or more stereoisomers of the compound of formula (II) to modify and / or strengthen, preferably to strengthen.

[0033] Further preferred is a fragrance composition according to the invention as described herein, preferably perfume oil, wherein the total amount of stereoisomer(s) of the compound of formula (I) based on the total weight of the fragrance composition, is 0.0001 to 10 wt.%, preferably 0.001 to 5 wt.%, particularly preferably 0.01 to 1 wt.%.

[0034] A further aspect of the present invention relates to a perfumed product containing a mixture according to the invention as described herein, or preferably a fragrance composition according to the invention as described herein, preferably a perfume oil, in a sensorially effective amount, wherein the proportion of the mixture or fragrance composition based on the total weight of the product is preferably in the range from 0.01 to 100% by weight, preferably 0.02 to 50% by weight, particularly preferably 0.1 to 20% by weight.-%, preferably wherein the product is selected from the group consisting of perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing wipes, acidic, alkaline and neutral cleaning agents, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents, fabric softeners, laundry soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products, deodorants and antiperspirants, decorative cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents and propellants.

[0035] A further aspect of the present invention also relates to a process for producing a perfumed product, preferably a product according to the invention as described herein, comprising the following steps: i) Providing a mixture according to the invention as described herein or a fragrance composition according to the invention as described herein, ii) Providing one or more further components of the perfumed product to be produced, and iii) Contacting or mixing the further components provided in step ii) with a sensorially effective amount of the components provided in step i).

[0036] For the above-described aspects of the invention, the above statements in connection with a use according to the invention preferably apply accordingly, and the statements in connection with the above-described aspects of the invention also apply accordingly to the use according to the invention. Furthermore, the embodiments described herein can be combined with one another as desired, to the extent technically feasible.

[0037] The present invention is further illustrated by the following examples. Unless otherwise stated, all data are by weight. Examples: Preferred mixtures of pyranol with Ambrocenide ®< Mixture 1

[0038] PYRANOL 1.000,00 AMBROCENIDE ®< 0,1

[0039] Effect: The lily of the valley note of the pyranol is intensified and more pronounced, which is accompanied by a higher quality. Mixture 2

[0040] PYRANOL 1.000,00 AMBROCENIDE ®< 1

[0041] Effect: The lily of the valley note of the pyranol becomes more substantial and natural, which makes Blend 2 seem more valuable. Perfume oils 1

[0042] A (comparison example) B (comparison example) C D ALDEHYDE C14 SOG 3,00 3 3 3 AMBROXIDE 15 15 15 15 BENZOATE SIAM ABS. 30 30 30 30 BENZYL ACETATE FG 2 2 2 2 BHT JONOL 2 2 2 2 Cashmere 20 20 20 20 COUMARIN 7 7 7 7 DECALACTON GAMMA 4 4 4 4 DIPROPYLENE GLYCOL 69,5 69,5 69,5 69,5 EBANOL 15 15 15 15 ETHYLENE BRASSYLATE 150 150 150 150 ETHYLMALTOL 10 10 10 10 FLOROSA 120 PYRANOL 120 HEXENOL CIS-3 10% DPG 8 8 8 8 HEXENYL ACETATE CIS-3 1 1 1 1 INDOL FF 1% DPG 5 5 5 5 ISO E SUPER 320 320 320 320 ISOEUGENOL 10% DPG 1,5 1,5 1,5 1,5 JASMINE ABS. SAMBAC REFA 50% BB 1,5 1,5 1,5 1,5 JASMON CIS 1 1 1 1 METHYLANTHRANILATE 10% DPG 0,5 0,5 0,5 0,5 MUSCENONE 7 7 7 7 MUSCONE 7 7 7 7 NORLIMBANOL 15 15 15 15 POLYSANTOL (MYSANTOL) 30 30 30 30 Red Berry Extract 5 5 5 5 SANDRANOL ®< 150 150 150 150 Mixture 1 120 Mixture 2 120 TOTAL 1000 1000 1000 1000 Perfume Oil A (comparison example): Standard fragrance composition with Florosa ®< as the lily of the valley fragrance. Perfume Oil B (comparison example): Florosa ®< from Perfume Oil A is replaced with pyranol. The scent of Perfume Oil B is less floral, less radiant, and less complex than Perfume Oil A. Perfume Oil C: Florosa ®< from Perfume Oil A is replaced with Blend 1 (as described above). The scent of Perfume Oil C is brighter, more body-like, and more hedonic than Perfume Oil B. Perfume Oil D: Florosa ®< from Perfume Oil A is replaced with Blend 2 (as described above). The scent of Perfume Oil D is stronger and more substantive than Perfume Oil B. Furthermore, Perfume Oil D is also brighter and more complex, and overall performs better than Perfume Oil A. Perfume oils 2

[0043] E (comparison example) F G AMAROCIT ®< 10 10 10 AMBRETTOLIDE 1,5 1,5 1,5 AMBROXIDE 0,5 0,5 0,5 AMYRIS OIL 2,5 2,5 2,5 AURELIONE ®< 25 25 25 BENZYL SALICYLATE 9 9 9 BERGAMOT OIL BERGATEN-FREE 40 40 40 CITRAL FF 1,5 1,5 1,5 CITRONELLOL L 1,5 1,5 1,5 CLARITONE ®< 5 5 5 DIMETHYLBENZYLCARBINYLBUTYRATE 10% DPG 1 1 1 ETHYLENE BRASSYLATE 50 50 50 FLOROPAL 10% DPG 3 3 3 FLOROSA 90 GLOBALIDE ®< 50 50 50 HEDION HC / 30 400 400 400 HELIOTROPIN / PIPERONAL 20 20 20 HEXYLCINAL ALDEHYDE ALPHA 10% DPG 1 1 1 ISO E SUPER 200 200 200 ISOBORNYLCYCLOHEXANOL 10 10 10 ISORALDEIN 95 30 30 30 LINALOOL 12 12 12 MAGNOLAN 23 23 23 MANDARIN OIL REMOVED 6 6 6 SANDALWOOD OIL PURE AUSTRALIA 7,5 7,5 7,5 Mixture 1 90 Mixture 2 90 TOTAL 1000 1000 1000 Perfume Oil E (comparison example): Standard fragrance composition with Florosa ®< as the lily of the valley fragrance. Perfume Oil F: Florosa ®< is replaced with Blend 1 (as described above); the olfactory improvement of the fragrance is slight, however, raw material costs can be saved by replacing Florosa ®< with Blend 1. Perfume Oil G: Florosa ®< is replaced with Blend 2 (as described above); the fragrance of fragrance composition G is stronger, more substantive, and has a more floral character than that of compositions E and F. Perfumed products Washing powder:

[0044] AGRUMEXLC 150 AMBERWOOD ®< F 12 BENZYLACETONE 50 CITRONELLOL 950 2 CITRONITRILE 2 CYCLAMENALDEHYDE 1 DIHYDROMYRCENOL 200 DIPROPYLENE GLYCOL 3 GERANIOL SUPRA 1 HERBYL PROPIONATE 80 HEXYL ACETATE 45 IONONE ALPHA 2 IONON BETA 6 ISO E SUPER 250 ISODAMASCON ®< 1 LINALOOL 20 MACROLIDE ®< SUPRA 10 MAGNOLAN 2 MANZANATE 1 NEROLIONE 10% DPG 2 ORANGE OIL 15 PHENIRATION ®< 50 PHENYLACETALDEHYDE DIMETHYLACETAL 1 PYROPRUNATE 2 ROSE OXIDE 1 SANDRANOL ®< 20 UNDECAVERTOL 5 VERTOCITRAL 1 YSAMBER ®< K 5 Mixture 1 60

[0045] The perfume oil gives the washing powder the typical scent one expects from this product. It conveys the message of cleanliness and freshness. In this case, the fragrance begins with a combination of aldehydes and citrus, which convey freshness. This is followed by a floral heart, which represents the caring character. The base note consists of long-lasting components with a woody, amber, and musky character, ensuring that the impression of fresh laundry lasts even days after washing. Shampoo:

[0046] AGRUMEX HC 80 ALDEHYDE C14 SOG 50 ALDEHYDE C16 SOG. 1 AMBROXIDE 4 PURE ANISALDHEHYDE 16 APPLE GREEN AROMA BASE 15 APRIFLOREN ®< 1 BERGAMOT OIL REAL 20 CITRONELLOL 950 40 CITRONELLYL ACETATE EXTRA 10 DECALACTON GAMMA 5 DIHYDROMYRCENOL 100 DIPROPYLENE GLYCOL 8 ETHYL LVANOLIMIN 10% DPG 4 EUGENOL NAT. 3 FRAMBINONE ®< 10% DPG 6 GERANYL ACETATE 60 20 GERANYL TIGLINATE 5 GLOBALIDE ®< 25 HEDION 60 HEXENAL TRANS-2 10% DPG 6 HEXENYL ACETATE CIS-3 10% DPG 9 HEXYL ACETATE 50 HEXYL SALICYLATE 15 INDOFLOR ®< CRYSTAL 10% DPG 2 ISO E SUPER 20 ISORALDEIN 70 15 JASMIN 61 TYPE BASE 20 LINALOOL 60 LINALYL ACETATE 150 PHENIRATION ®< 50 ROSE DE MAI-BASE 30 ROSE OXIDE L 5 SANDRANOL ®< 15 VERTOCITRAL 10 Mixture 2 70

[0047] The perfume oil, as a fragrance, conveys the expectations one has of the product. In this case, a shampoo, one expects cleansing and care. This is conveyed through the scent. A clean apple / citrus combination reflects the cleansing aspect, while the heart of the fragrance (floral with fruity notes) represents the caring aspect. The fragrance experience is rounded out by warm, woody, and musky components.

Claims

1. Use of one or more stereoisomer(s) of the compound of formula (I) for modifying and / or enhancing, preferably for enhancing, the olfactory impression of one or more odorant / odorants with a lily-of-the-valley note, wherein the or one or several odorant(s) is or are selected from the group consisting of 7-hydroxy-3,7-dimethyloctanal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, 2,2-dimethyl-3-(3-methylphenyl)propanol, cis-4-(1-methylethyl)cyclohexanemethanol, 1-(4-isopropylcyclohexyl)ethanol, 3-methyl-4-phenylbutan-2-ol, dimethylphenyl propanol, and compound of formula (II), preferably wherein the odorant is a compound of formula (II).

2. Use according to claim 1, wherein the odorant or one of the odorants comprises or consists of two or more stereoisomers of the compound of formula (II) wherein preferably the weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(-) is between 65 : 35 and 95 : 5, preferably 70 : 30 and 90 : 10, particularly preferably 75 : 25 and 85 : 15.

3. Mixture comprising or consisting of one or more stereoisomer(s) of the compound of formula (I) and two or more stereoisomers of the compound of formula (II) wherein the weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(-) is between 65 : 35 and 95 : 5, preferably 70 : 30 and 90 : 10, particularly preferably 75 : 25 and 85 : 15.

4. Mixture according to claim 3, wherein the weight ratio of the total amount of stereoisomer(s) of the compound of formula (I) to the total amount of stereoisomers of the compound of formula (II) is between 1 : 12000 and 1 : 0.5, preferably between 1 : 600 and 1 : 0.7, particularly preferably between 1 : 100 and 1 : 1, and / or wherein the total amount of stereoisomer(s) of the compound of formula (I) is sufficient to modify and / or enhance, preferably enhance, the olfactory impression of the two or more stereoisomers of the compound of formula (II).

5. Method for modifying and / or enhancing, preferably for enhancing, the lily-of-the-valley note of a compound of formula (II), comprising or consisting of the following steps: i) Providing one or more stereoisomer(s) of the compound of formula (I) ii) Providing two or more stereoisomers of the compound of formula (II) wherein the weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(-) to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(-) is between 65 : 35 and 95 : 5, preferably 70 : 30 and 90 : 10, particularly preferably 75 : 25 and 85 : 15, iii) Mixing the compounds provided in steps i) and ii), preferably wherein the amount of the one or more stereoisomer / stereoisomers of the compound of formula (I) is sufficient to modify and / or enhance, preferably enhance, the lily-of-the-valley note of the compound of formula (II).

6. Method according to claim 5, wherein the weight ratio of the total amount of stereoisomer(s) of the compound of formula (I) to the total amount of stereoisomers of the compound of formula (II) is between 1 : 12000 and 1 : 0.5, preferably between 1 : 600 and 1 : 0.7, particularly preferably between 1 : 10 and 1 : 1.

7. Fragrance composition, preferably perfume oil, comprising or consisting of a mixture according to any one of claims 3 or 4 and preferably also one or more additional fragrances, preferably wherein the additional or one, several or all of the additional fragrances is or are selected from the group consisting of 3-(4-methyl-1-cyclohex-3-enyl)-butanal, 4-(4-hydroxyphenyl)butan-2-one, (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one, (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one, (E)-1-(2,6,6-trimethyl-cyclohexen-1-yl)pent-1-en-3-one, (E)-4-[(1S)-1,2,6,6-tetramethylcyclohex-2-en-1-yl]but-3-en-2-one, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one, [(Z)-hex-3-enyl] methyl carbonate, 3-[(Z)-hex-3-enoxy]propane nitrile, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexa-hydronaphthalen-2-yl)ethanone, spiro[1,3-dioxolan-2,5'-(4',4',8',8'-tetramethyl-hexahydro-3',9'-methanonaphthalene)], [3R-(3a,3aβ,6β,7β,8aα)]-octa-hydro-6-methoxy-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene, [3R-(3α,3aβ,7β,8aα)]-1-(2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methano-azulen-5-yl)ethan-1-one, 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, 2,6-dimethyloct-7-en-2-ol, 3,7-dimethylocta-1,6-dien-3-ol, (3,7-dimethylocta-1,6-dien-3-yl)acetate, (4-methyl-1-propan-2-yl-1-cyclohex-2-enyl) acetate, (8E)-Cyclohexadec-8-en-1-one, 16-Oxacyclohexa-decan-1-one, 1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyrane, ethoxymethoxy-cyclododecane, 1,1,2,3,3-pentamethyl-2,5,6,7-tetrahydroinden-4-one, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone.

8. Fragrance composition according to claim 7, wherein the total amount of stereoisomer(s) of the compound of formula (I) is sufficient to modify and / or enhance, preferably enhance, the olfactory impression of the two or more stereoisomers of the compound of formula (II) 9. Fragrance composition according to any one of claims 7 or 8, preferably perfume oil, wherein the total amount of stereoisomer(s) of the compound of formula (I) is from 0.0001 to 10% by weight, preferably from 0.001 to 5% by weight, particularly preferably from 0.01 to 1% by weight, based on the total weight of the fragrance composition.

10. Perfumed product comprising a mixture according to any one of claims 3 or 4, or preferably a fragrance composition according to any one of claims 7 to 9, preferably a perfume oil, in a sensorially effective amount, wherein the proportion of the mixture or fragrance composition based on the total weight of the product is preferably in the range of from 0.01 to 100% by weight, preferably from 0.02 to 50% by weight, particularly preferably from 0.1 to 20% by weight, preferably wherein the product is selected from the group consisting of perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing tissues, acidic, alkaline and neutral cleaning agents, fabric fresheners, ironing aids, liquid detergents, powder detergents, laundry pre-treatments, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products, deodorants and antiperspirants, decorative cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents, and fuels.

11. Method for manufacturing a perfumed product, preferably a product according to claim 10, comprising the following steps: i) Providing a mixture according to any one of claims 3 or 4 or a fragrance composition according to any one of claims 7 to 9, ii) Providing one or more further ingredients of the perfumed product to be manufactured, and iii) contacting or mixing the further ingredients provided in step (ii) with a sensorially effective amount of the ingredients provided in step (i).