2,4-Dimethyloct-2,7-dien-4-ol as a fragrance

Abstract

The use of compounds of formula (I) as flavorings is proposed.

Description

Field of the invention

[0001] The present invention relates to the use of the compound 2,4-dimethyloct-2,7-dien-4-ol of the formula (I) as a fragrance. The invention also relates to fragrance compositions, their use and to a method for imparting, modifying and / or enhancing certain odor notes. BACKGROUND

[0003] The perfume industry is constantly in need of new fragrance creations. However, the creation of a new fragrance or perfume is faced with many challenges. For example, it is necessary to select a specific composition of a small number of fragrances from the almost infinite number of possible structures known from the prior art in order to meet the specific demands of the market and to provide a product that meets the specific needs of the customer. Although suitable fragrances exhibit quite advantageous properties, their combination with other fragrances can result in unpleasant and thus disadvantageous odor aspects, which makes their use for a specific purpose difficult, if not impossible.

[0004] A second important problem relates to the need to provide fragrance substance compositions which not only meet specific odor characteristics, but also have so-called secondary advantageous properties. In fact, many fragrance compositions known on the market have considerable disadvantages in their application, for example poor solubility and poor storage stability, but also errors in subjective properties such as roundness, charisma, etc. In addition, many known fragrance compositions require high dosages to achieve the desired odor result. Today, further requirements for fragrances are high biodegradability as well as dermatological and toxicological safety. Thus, a particularly high demand is to provide a fragrance which intensifies other fragrances and / or positively modifies quite unpleasant odor impressions and / or enhances pleasant odor impressions with small dosages.

[0005] Therefore, the task on which the present invention is based is to provide a new fragrance which is able to improve the positive and advantageous odor aspects of other fragrances and / or (at the same time) to reduce, inhibit and / or mask any undesirable, unpleasant odor aspects. In particular, the new fragrance should also have the following features: it improves the stability, solubility and overall performance of other fragrances and reduces the required dosage. Finally, the fragrance composition itself should exhibit excellent biodegradability and be safe for humans and the environment. SUMMARY

[0006] According to the invention, the present main task is solved by using the compound of the formula (I) (2,4-dimethyloct-2,7-dien-4-ol, CAS No. 120792-35-0) as a fragrance.

[0007]

[0008] The compound of formula (I) used according to the present invention may exist in any stereoisomer form or in any mixture of stereoisomers.

[0009] The contents described herein with respect to compounds of formula (I), and in particular the advantages described herein, should be compared with those applicable to mixtures of stereoisomers of compounds of formula (I) used or employed according to the present invention (see above).

[0010] In the event of any unintentional difference between the chemical name and the structural formula shown within the scope of this document, the structural formula shown shall prevail.

[0011] Compounds of formula (I) possess the most distinctive olfactory properties, clearly standing out from and even surpassing those of known fragrances. To date, the suitability of compounds of formula (I) as fragrances remains unclear. Therefore, it is particularly surprising to find fragrances with valuable, interesting, and complex olfactory properties within this well-studied field.

[0012] Compound (I) is known in the fragrance industry as an intermediate in the production of linalool from pinene, under the name isolinalool (2,4-dimethyloct-2,7-dien-4-ol). Furthermore, there is no precise fragrance description; however, according to perfumers, compound (I) smells like juniper berries, terroir, and carrots, and is therefore quite unpleasant.

[0013] Therefore, the inventors were surprised to find that the compound of formula (I) is suitable as a flavoring agent, and can be combined with other flavoring agents, especially flavoring agents having one or more flavoring notes selected from fruity, floral, juicy, fresh, sweet, green, technical, earthy, fatty and metallic flavoring notes, to induce specific effects in small doses: preferably one or more flavoring notes selected from fruity, floral, juicy, fresh, sweet and green flavoring notes, especially one or more flavoring notes selected from fruity and floral flavoring notes.

[0014] Preferably, the use according to the invention relates to the use of imparting, modifying, and / or enhancing one or more odor notes selected from fruity, floral, juicy, fresh, sweet, green, technical, earthy, fatty, and metallic odor notes, preferably one or more selected from fruity, floral, juicy, fresh, sweet, and green odor notes, and more preferably one or more selected from fruity and floral odor notes. Preferred embodiments relate to the use of compounds of formula (I) described herein for imparting one, two, or more odor notes selected from fruity and floral odor notes.

[0015] In fact, the compounds of formula (I) used according to the present invention can impart very complex and varied overall sensory impressions, which in most cases can only be obtained by a mixture of several components (e.g., essential oils or fragrance mixtures), which is particularly surprising.

[0016] In addition to its primary property, namely odor, the compound of formula (I) also has positive secondary properties, particularly high substantiality compared to fragrances with similar odor properties, high stability in specific media and compositions, high abundance, and biodegradability.

[0017] The preferred uses for imparting, modifying and / or enhancing odor notes also include the discovery that compounds of formula (I) can serve as excellent so-called enhancers (reinforcing agents).

[0018] The compounds of formula (I) used according to the present invention can also enhance the strength of the fragrance mixture (fragrance composition) and can provide the mixture with a final olfactory touch. Therefore, the compounds described herein can be used to impart more body, freshness, (radiant) power, radiance, lustre, roundness, harmony and / or naturalness to the fragrance composition.

[0019] In addition, compounds of formula (I) are suitable as a means of increasing the affinity and / or retention of flavor blends.

[0020] The preparation of the compound of formula (I) used according to the present invention can be carried out by reactions and methods known per se. As is known to those skilled in the art, the compound of formula (I) is an intermediate product in the production of linalool from pinene. Figure 1 below shows a schematic diagram of the linalool production process (the precipitate used for this purpose is commercially available).

[0021]

[0022] Figure 1: Method for producing linalool from pinene, wherein compound (I) is the intermediate product.

[0023] The compound of formula (I) used according to the invention is generally used in a sensorily effective amount within the scope of its use according to the invention, i.e., the total amount used to exhibit the sensory effect. Preferably, the compound of formula (I) used according to the invention is used in conjunction with other flavorings. Such flavoring compositions can be produced in a conventional manner, for example, by simply mixing or homogenizing the components. These other flavorings can be any other flavorings.

[0024] In a preferred embodiment of the invention, the fruity aroma is selected from pineapple, apple, and / or plum. In another preferred embodiment of the invention, the floral aroma is selected from jasmine, magnolia, peony, lily of the valley, lily, clove, and / or rose.

[0025] Furthermore, the present invention relates to a fragrance composition comprising or consisting of the following components: compounds of formula (I)

[0026]

[0027] And at least one other spice.

[0028] Preferably, the flavoring composition comprises or consists of a compound of formula (I) and one, two, three, four, five, six, seven, eight, nine, ten or more other flavorings.

[0029] Preferably, the total amount of the compound of formula (I) is in a weight ratio of 1:1000 to 1:0.1 to the total amount of other flavorings, more preferably 1:1000 to 1:0.5.

[0030] In this document, the total amount of the preferred formula (I) compound is 0.0001 to 99.9% by weight, preferably 0.001 to 99.5% by weight, particularly preferably 0.01 to 99% by weight, 0.01 to 90% by weight, 0.01 to 50% by weight, 0.01 to 20% by weight, and particularly preferably 0.01 to 1.5% by weight, especially 0.05 to 1.5% by weight, each based on the total weight of the flavor composition.

[0031] Advantageously, the total amount of the compound of formula (I) in the fragrance composition is selected such that it is contained in a sensory effective amount, which is sufficient to impart and / or enhance and / or modify one or more aroma notes selected from fruity, floral, juicy, fresh, sweet, green, technical, earthy, fatty and metallic aroma notes, preferably one or more aroma notes selected from fruity, floral, juicy, fresh, sweet and green aroma notes.

[0032] Particularly preferred is that one or more or all other flavorings are also imparted, modified and / or enhanced, however particularly imparted one or more aroma notes selected from fruity, floral, juicy, fresh, sweet, green, technical, earthy, fatty and metallic aroma notes, preferably one or more aroma notes selected from fruity, floral, juicy, fresh, sweet and green aroma notes.

[0033] Examples of fragrances that can be advantageously combined with compounds of formula (I) within the scope of this invention can be found, for example, in S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, NJ 1969, self-published, or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001.

[0034] Specifically, the following substances are mentioned: extracts from natural raw materials, such as essential oils, extracts, absolutes, resins, resin-like substances, balsams, and tinctures, such as ambra tincture; amyris balsamifera oil; angelica seed oil; angelica root oil; anise oil; and valerian essential oil.

[0035] Basil essential oil; tree moss essential oil; laurel oil; wormwood oil; benzoin; bergamot oil;

[0036] Beeswax oil; birch tar; bitter almond oil; savory oil; broom leaf oil;

[0037] Brazilian sandalwood oil (cabreuva oil); juniper oil (caden oil); calmus oil (calmus oil); camphor oil; cananga oil (cananga oil); cardamom oil (cardamom oil); cascarilla oil (cascarilla oil); cassia oil (cassia oil); cassie absolue (cassie absolue); castor oil (castoreum absolue); cedar leaf oil; cedarwood oil; rockrose oil; lemongrass oil; lemongrass oil; copaiba balsam; copaiba balsam oil; coriander oil; costus root oil;

[0038] Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Eau de brouts absolue; Oak moss absolue; Elemi oil; Tarragon oil; Eucalyptus citriodora oil; Eucalyptus oil;

[0039] Fennel oil; Spruce needle oil; Galbanum oil; Galbanum resin; Bay leaf oil; Grapefruit oil; Guaiac oil; Gurunella balsam; Gurunella oil; Helichrysum absolute; Helichrysum oil; Ginger oil; Orris root absolute; Orris root oil; Jasmine absolute; Sweet flag oil; Chamomile oil blue;

[0040] Roman chamomile oil; carrot seed oil; cascarilla oil; pine needle oil; spearmint oil; caraway oil; labdanum oil; labdanum absolue; labdanum resin; lavandin absolue; lavandin oil; lavender absolue; lavandin oil; lavender oil; lemongrass oil; lovage oil; distilled lime oil; pressed lime oil; lina oil; litsea cubeba oil; bay leaf oil; macis oil; marjoram oil; citrus oil; massoi rind oil; mimosa absolue; musk seed oil;

[0041] Musk tincture; Muscat sage oil; nutmeg oil; myrrh puree oil; myrrh oil;

[0042] Myrtle oil; clove leaf oil; clove flower oil; neroli flower oil; frankincense absolute (olibanum absolue); frankincense oil (olibanum oil); opopanax oil; neroli absolute; orange oil; oregano oil; palmarosa oil; patchouli oil;

[0043] Perilla oil; Peruvian balsam oil; Parsley leaf oil; Parsley seed oil; Petit grain oil; Peppermint oil; Pepper oil; Pimento oil; Pine oil; Poley oil; Rose absolute; Rosewood oil; Rose oil;

[0044] Rosemary oil; Dalmatian sage oil; Spanish sage oil; sandalwood oil; celery seed oil; spiked lavender oil; star anise oil; styrax oil; marigold oil; fir needle oil; tea tree oil; turpentine oil; thyme oil; tolu balsam; tonka absolue; tuberose absolue; vanilla extract; violet leaf absolue; verbena oil; vetiver oil; juniper berry oil; wine yeast oil; artemisia oil; wintergreen oil; ylang-ylang oil; hyssop oil; civet absolue; cinnamon leaf oil; cinnamon bark oil and its fractions, or inclusions isolated therefrom;

[0045] Single fragrance compounds derived from hydrocarbons, such as 3-caren; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymol; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longleafene; myrcene; ocimene; valence; (E,Z)-1,3,5-undecanetriene; styrene; diphenylmethane;

[0046] Aliphatic alcohols, such as hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E)-2-hexenol; 1-octen-3-ol; a mixture of 3,4,5,6,6-pentamethyl-3,4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methylenehepten-2-ol; (E,Z)-2,6-nonadienol; 3,7-dimethyl-7-methoxyoct-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;

[0047] Aliphatic aldehydes and their acetals, such as hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; 2-methyloctanal; 2-methylnonanal; (E)-2-hexenal; (Z)-4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (E)-4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10-trimethyl-5,9-undecadienal; heptanal divinyl alcohol; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronelloloxyacetaldehyde; 1-(1-methoxy-propoxy)-(E / Z)-3-hexene;

[0048] Aliphatic ketones and their oximes, such as 2-heptanone; 2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;

[0049] Aliphatic sulfur-containing compounds, such as 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthol-8-thiol;

[0050] Aliphatic nitrile, such as 2-nonenoic acid nitrile; 2-undecenoic acid nitrile; 2-tetratecenoic acid nitrile; 3,12-tetratecadienoic acid nitrile; 3,7-dimethyl-2,6-octadienoic acid nitrile; 3,7-dimethyl-6-octenoic acid nitrile;

[0051] Esters of aliphatic carboxylic acids, such as (E)- and (Z)-3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E)-2-hexenyl acetate; (E)- and (Z)-3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; (E)- and (Z)-3-hexenyl isobutyrate; crotonic acid. Hexyl ester; Ethyl isovalerate; Ethyl 2-methylvalerate; Ethyl hexanoate; Allyl hexanoate; Ethyl heptaate; Allyl heptaate; Ethyl octanoate; (E,Z)-2,4-decadienoate; Methyl 2-octinate; Methyl 2-noninate; Allyl 2-isopentoxyacetate; Methyl 3,7-dimethyl-2,6-octadienate; 4-methyl-2-pentyl crotonate;

[0052] Noncyclic terpene alcohols, such as geraniol; nerol; lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloct-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-1,5,7-octtrien-3-ol; 2,6-dimethyl-2,5,7-octtrien-1-ol; and their formate, acetate, propionate, isobutyrate, butyrate, isovalerate, valerate, hexanoate, crotonate, tiglinate, and 3-methyl-2-butenoate;

[0053] Noncyclic terpenoid aldehydes and ketones, such as citronellol; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geraniol acetone; and dimethyl and diethyl acetals of geraniol and neraldehyde;

[0054] Cyclic terpenoid alcohols, such as menthol; isomenthol; α-terpineol; terpineol-4; menthane-8-ol; menthane-1-ol; menthane-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambrinol; vetiverol; guaiaol; and their formate, acetate, propionate, isobutyrate, butyrate, isovalerate, valerate, hexanoate, crotonate, tiglinate, and 3-methyl-2-butenoate;

[0055] Cyclic terpenoid aldehydes and ketones, such as menthone; isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; frankinc; α-ionone; β-ionone; α-methylionone; β-methylionone; α-isomethylionone; β-isomethylionone; α-iridinone; β-damasconone; 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-bridged methylene-naphthyl-8(5H)-one; 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; nocacolone; dihydronocacolone; 4,6,8-megastigmatrien-3-one; α-sweet orange aldehyde; β-sweet orange aldehyde; acetylated cedar oil (methyl cedar ketone);

[0056] Cyclohydric alcohols, such as 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isoborneolcyclohexanol; 2,6,9-trimethyl-Z2,Z5,E9-cyclododecanetrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

[0057] Alicyclic alcohols, such as α,3,3-trimethylcyclohexylethanol; 1-(4-isopropylcyclohexyl)ethanol; 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol; 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl) -Pentan-2-ol; 3-Methyl-5-(2,2,3-trimethyl-3-cyclopentan-1-yl)-4-penten-2-ol; 3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopentan-1-yl)-4-penten-2-ol; 1-(2,2,6-trimethylcyclohexyl)pentan-3-ol; 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol;

[0058] Cyclic and alicyclic ethers, for example, cineol; methyl cedarwood ether; cyclododecyl methyl ether; 1,1-dimethoxycyclododecane; (ethoxymethoxy)cyclododecane; α-cedrene epoxide; 3a,6,6,9a-tetramethyldodecano-naphtho[2,1-B]furan; 3a-ethyl 6,6,9a-trimethyldodecano-naphtho[2,1b]furan; 1,5,9-trimethyl-13-oxabicyclo[10.1.0]tetane-4,8-diene; rose oxide; 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane;

[0059] Cyclic and macrocyclic ketones, such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone ; 3-Methyl-5-cyclopentadecanone; 3-Methylcyclopentadecanone; 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone; 4-tert-amylcyclohexanone; 5-cyclohexadecene-1-one; 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone; 8-cyclohexadecene-1-one; 9-cycloheptadecene-1-one; cyclopentadecanone; cyclohexadecenecanone;

[0060] Alicyclic aldehydes, such as 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenal; 4-(4-methyl-3-penten-1-yl)-3-cyclohexenal;

[0061] Alicyclic ketones, such as 1-(3,3-dimethylcyclohexyl)-4-penten-1-one; 2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone; 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthylmethyl ketone; methyl-2,6,10-trimethyl-2,5,9-cyclododecanetrienyl ketone; tert-butyl-(2,4-dimethyl-3-cyclohexen-1-yl)one;

[0062] Esters of cyclic alcohols, such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-ester of acetate; decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate. ; 4,7-bridged methylene-3a,4,5,6,7,7a-hexahydro-5 or 6-indanyl acetate; 4,7-bridged methylene-3a,4,5,6,7,7a-hexahydro-5 or 6-indanylpropionate; 4,7-bridged methylene-3a,4,5,6,7,7a-hexahydro-5 or 6-indanyl isobutyrate; 4,7-bridged methylene octahydro-5 or 6-indanyl acetate;

[0063] Esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate;

[0064] Esters of alicyclic carboxylic acids, such as allyl 3-cyclohexylpropionate; allyl cyclohexyloxyacetate; methyl cis and trans-dihydrojasmonic acid; methyl cis and trans-jasmonic acid; methyl 2-hexyl-3-oxocyclopentanecarboxylate; ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; ethyl 2-methyl-1,3-dioxolane-2-ethyl acetate;

[0065] Aromatic aliphatic alcohols, such as benzyl alcohol; 1-phenylethanol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3-(3-methylphenyl)propanol; 1,1-dimethyl-2-phenylethanol; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1-(4-isopropylphenyl)ethanol;

[0066] Esters of aliphatic alcohols and aliphatic carboxylic acids, such as benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; α-trichloromethyl benzyl acetate; α,α-dimethylphenylethyl acetate; α,α-dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;

[0067] Aromatic aliphatic ethers, such as 2-phenylethyl methyl ether; 2-phenylethyl isopentyl ether; 2-phenylethyl-1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; β-phenylpropanal dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a,5,9b-tetrahydroindo[1,2-d]-m-dioxin; 4,4a,5,9b-tetrahydro-2,4-dimethylindo[1,2-d]-m-dioxin;

[0068] Aromatic and arylita-alkyl aldehydes, such as benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; solanal (hydratropicaldehyde); 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3-(4-ethylphenyl)-2,2-dimethylpropanal; 2-methyl-3-(4-isopropylphenyl)propanal; 2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert-butylphenyl)propanal; cinnamaldehyde; α-butylcinnamaldehyde; α-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3-(4-methoxyphenyl)propanal; 2-methyl-3-(4-methylenedioxyphenyl)propanal;

[0069] Aromatic and arylita-ketones, such as acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4-(4-hydroxyphenyl)-2-butanone; 1-(2-naphthyl-enyl)acetone; 2-benzofuranylacetone; (3-methyl-2-benzofuranyl)acetone; benzophenone; 1,1,2,3,3,6-hexamethyl-5-indenemethyl ketone; 6-tert-butyl-1,1-dimethyl-4-indenemethyl ketone; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indene]acetone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2-acetyl-naphthone;

[0070] Aromatic and aryl aliphatic carboxylic acids and their esters, such as benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geraniol phenylacetate; phenylethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamate; allyl phenoxyacetate; methyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenylethyl salicylate; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; ethyl 3-phenylglycidate; ethyl 3-methyl-3-phenylglycidate;

[0071] Nitrogen-containing aromatic compounds, such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamic acid nitrile; 3-methyl-5-phenyl-2-pentenic acid nitrile; 3-methyl-5-phenylpentanic acid nitrile; methyl anthranilate; methyl anthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert-butyl-phenyl)propanal or 2,4-dimethyl-3-cyclohexenecarboxaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2-(3-phenylpropyl)pyridine; indole; skatol; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;

[0072] Phenols, phenyl ethers, and phenyl esters, such as estragol; anethole; eugenol methyl ether; isoeugenol; isoeugenol methyl ether; thymol; carvacrol; diphenyl ether; β-naphthyl methyl ether; β-naphthyl ethyl ether; β-naphthyl isobutyl ether; 1,4-dimethoxybenzene; eugenol acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5-(1-propenyl)phenol; p-tolylphenylacetic acid ester;

[0073] Heterocyclic compounds, such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;

[0074] Lactones, such as 1,4-octanolactone; 3-methyl-1,4-octanolactone; 1,4-nonanolactone; 1,4-decanolactone; 8-decen-1,4-lactone; 1,4-undecanolactone; 1,4-dodecanolactone; 1,5-decanolactone; 1,5-dodecanolactone; 4-methyl-1,4-decanolactone; 1,15-pentadecanolactone; 1,16-hexadecanolactone; 9-hexadecene-1,16-lactone; 10-oxa-1,16-hexadecanolactone; 11-oxa-1,16-hexadecanolactone; 12-oxa-1,16-hexadecanolactone; ethylene-1,12-dodecanoic acid ester; ethylene-1,13-tridecanoic acid ester; 2,3-dihydrocoumarin; octahydrocoumarin.

[0075] In a preferred embodiment of the invention, at least one other fragrance is selected from terpenes, aldehydes, nitriles, esters, lactones, alcohols and mixtures thereof.

[0076] In another preferred embodiment of the fragrance composition of the present invention, the compound of formula (I) used according to the present invention is preferably combined with one or more, particularly preferably two, three, four, five or more other fragrances having floral and / or fruity aroma notes.

[0077] Therefore, the present invention also relates to a fragrance composition comprising one, two, three, four, five or more other fragrances that impart floral and / or fruity aroma notes.

[0078] In this case, the compound of formula (I) used according to the invention advantageously enhances the aroma of floral fragrances (at least partially).

[0079] Floral fragrances that can be particularly advantageously combined with compounds of formula (I) used according to the invention (especially in fragrance compositions according to the invention) are preferably selected from:

[0080] Hydroxycitronellal, methoxycitronellal, bacitronellal, [2-methyl-3-(4-isopropylphenyl)propanal], 1-(4-isopropyl-cyclohexyl)ethanol 4-tert-butyl-α-methyldihydrocinnamaldehyde cis-hexahydrocuminol 3-[4-(1,1-dimethylethyl)phenyl]propionaldehyde 2,2-Dimethyl-3-(3-methylphenyl)propanol 3-Methyl-3-(3-methylbenzyl)-but-2-ol, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde 4-(octahydro-4,7-methyl-5H-inden-5-ylidene-butyraldehyde) Vernaldehyd, ethyl 2-methylbutyrate, 4-(4-methyl-3-penten-1-yl)-3-cyclohexenylformaldehyde Octahydro-5-(4-methoxybutylene)-4,7-methylene-1H-indene 2,6-Dimethyl-2-heptanol 1-Ethyl-1-methyl-3-phenylpropanol 2,2-Dimethyl-3-phenyl-1-propanol (Muguet alcohol), Profarnesol, dihydrofarnesol, farnesol, nerolidol, hydroxycitronellol, hexyl benzoate, geraniol, nerol, linalool, tetrahydrogeraniol, tetrahydrolinalool, ethyllinalool, Geranyltiglinat, phenylethanol (2-phenylethanol), 3,7-dimethyloct-6-en-1-ol (citronellol), rose oxide, 2-methyl-5-phenylpentanol (Rosaphen), 3-methyl-5-phenylpentanol (Phenoxanol), methyl dihydrojasmonate ( High cis), 2-heptacyclopentanone (Projasmon P), cis jasmone, dihydrojasmone, cinnamyl alcohol (3-phenyl-2-propen-1-ol), dihydrocinnamyl alcohol (3-phenylpropanol), 2-methyl-4-phenyl-1,3-dioxolane Benzyl acetate, benzyl salicylate, and dihydromyrcenol (2,6-dimethyl-7-octen-2-ol).

[0081] Furthermore, the compound of formula (I) used according to the present invention is advantageously suited for enhancing the aroma, particularly that of fruit flavorings.

[0082] Fruity flavorings that can be advantageously combined with compounds of formula (I) used according to the invention, and therefore are particularly preferred (other) flavorings for flavoring compositions according to the invention, preferably selected from:

[0083] Benzyl acetate, (2,4-dimethyl-1,3-dioxolane)ethyl acetate, 2-cyclopentenyl ethyl acetate, (E)-but-2-enoic acid 1-cyclohexyl ethyl ester, 2-methylbutyrate, 4-(p-hydroxyphenyl)-2-butanone, 3-methyl-3-phenyl glycidyl ethyl acetate, isoamyl butyrate, isoamyl acetate, n-butyl acetate, ethyl butyrate, 3-methylbutyrate, ethyl hexanoate, allyl hexanoate, 2-trans-4-ethylhexanoate - Ethyl cis-decadienoate, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-aldehyde, γ-undecylactone, γ-nonadecanolactone, hexanal, 3Z-hexenal, n-decanal, n-dodecanoal, citral, vanillin, ethyl vanillin, maltol, ethyl maltol, (E)-but-2-enoic acid 4-methylpentan-2-ester (Frutinat), (E)-but-2-enoic acid (2-cyclopentylcyclopentyl ester) (Pyroprunat), γ-undecylactone and mixtures thereof.

[0084] In a preferred embodiment of the invention, the at least one other fragrance is selected from ethyl 2-cyclopentenyl acetate, ethyl (E)-but-2-enoic acid 1-cyclohexyl ethyl ester, ethyl 2-methylbutyrate, ethyl 2,4-dimethyl-1,3-dioxolane-2-yl)ethyl acetate, 4-methylpentan-2-ester (E)-but-2-enoic acid (2-cyclopentylcyclopentyl ester), phenethyl alcohol, 5-(3-methylphenyl)pentan-1-ol, benzyl acetate, methyl 3-oxo-2-pentylcyclopentanacetate, 1-(4-prop-2-ylcyclohexyl)ethanol, 3,7-dimethyloct-6-en-1-ol, γ-undecyl lactone, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol and / or mixtures thereof.

[0085] The fragrance compositions of the present invention containing a compound of formula (I) can be used advantageously for flavoring in liquid form, undiluted or diluted with a solvent. Preferred solvents for this purpose include ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butanediol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetate, and diacetate.

[0086] Furthermore, the fragrance composition according to the invention can be adsorbed onto a carrier material that provides fine distribution of the fragrance in the product and controlled release during application. Suitable carriers can be porous inorganic materials, such as light sulfates, silica gels, zeolites, gypsum, clay, clay particles, aerated concrete, etc., or organic materials, such as wood, cellulose-based materials, sugars, dextrins (e.g., maltodextrin), or plastics, such as PVC, polyvinyl acetate, or polyurethane. The resulting combination of the composition and carrier material according to the invention should also be understood as a fragrance composition according to the invention or as an article according to the invention (as described below).

[0087] The fragrance composition according to the invention can also be microencapsulated, spray-dried, or exist as an inclusion complex or as an extruded product, and in the case of the fragrance composition, can be added to, for example, a product to be fragranced.

[0088] Optionally, the properties of such modified compositions or articles can be further optimized for more targeted fragrance release by "coating" with a suitable material, preferably a waxy plastic such as polyvinyl alcohol. The resulting product represents an article according to the invention.

[0089] Another aspect of the invention relates to the use of a fragrance composition for imparting, modifying, and / or enhancing one or more aroma notes selected from fruity, floral, juicy, fresh, sweet, green, technical, earthy, fatty, and metallic aroma notes, preferably one or more selected from fruity, floral, juicy, fresh, sweet, and green aroma notes. In a particularly preferred form, the aroma notes are selected from fruity and floral aromas. For preferred embodiments, the above-mentioned content relating to the use according to the invention or the fragrance composition according to the invention should be applied mutatis mutandis.

[0090] Advantageously, the fragrance compositions according to the invention can be prepared in concentrated form, solution form, or modified form as described above to prepare scented articles of the invention, such as perfume extracts; perfumes; eau de toilette; shaving lotions; eau de colognes; preshave products; cologne pats and scented tissues; and scented acidic, alkaline, and neutral detergents such as floor cleaners, window cleaners, dishwashing liquids, bathroom and sanitary cleaners, and scouring pads. Milk); solid and liquid toilet cleaners; powder and foam carpet cleaners; textile fresheners; ironing aids; liquid detergents; laundry powder; laundry pretreatment agents such as bleach, soaking agents, and stain removers; fabric softeners; laundry soaps; laundry sheets; disinfectants; surface disinfectants; and air fresheners in liquid, gel, or applied to a solid carrier form; aerosol sprays; waxes and polishes such as furniture polish, floor wax, shoe polish, and body care products such as solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, oil-in-water, oil-in-water, and water-in-oil-in-water cosmetics. Emulsions such as skin creams and lotions, face creams and lotions, sunscreens and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, hair removal creams and lotions, aftershave creams and lotions, tanning creams and lotions; hair care products such as hair sprays, hair gels, hair hardening lotions, conditioners, permanent and semi-permanent hair dyes; hair transformation agents such as cold waves and straighteners, hair growth tonics, hair creams and lotions; deodorants and antiperspirants such as underarm sprays, rollers, deodorant sticks, deodorant creams; decorative cosmetics such as eyeshadow, nail polish, makeup cosmetics, lipsticks, mascaras, and candles; lamp oil; incense sticks; insecticides; insect repellents and fuels.

[0091] Of course, the fragrance composition according to the invention can also be part of the most diverse range of cosmetic compositions or household chemical compositions.

[0092] Another aspect of the present invention relates to a method of imparting, enhancing, and / or modifying one or more aroma notes, said aroma notes being selected from fruity, floral, juicy, fresh, sweet, green, technical, earthy, fatty, and metallic aroma notes, preferably one or more aroma notes selected from fruity, floral, juicy, fresh, sweet, and green aroma notes, particularly preferably one or more fruity and floral aroma notes, comprising or consisting of the following steps:

[0093] (a) Provides compound of formula (I)

[0094]

[0095] (b) Provide at least one other spice.

[0096] (c) The compound of formula (I) is added to the at least one other flavoring agent in a sensory effective amount sufficient to impart and / or enhance and / or modify one or more aroma notes selected from fruity, floral, juicy, fresh, sweet, green, technical, earthy, fatty and metallic aroma notes, preferably one or more aroma notes selected from fruity, floral, juicy, fresh, sweet and green aroma notes.

[0097] In a preferred embodiment of the invention, at least one other fragrance has one or more aroma notes selected from fruity, floral, juicy, fresh, sweet, green, technical, earthy, fatty, and metallic scents.

[0098] Another aspect of the present invention relates to flavored articles comprising or consisting of the following components:

[0099] (i) the fragrance composition according to the invention, as defined above;

[0100] (ii) at least one other spice, and

[0101] (iii) One or more other components, preferably one or more adjuvants and / or active ingredients.

[0102] In a preferred embodiment, the article is selected from cosmetics, hygiene products, and / or household products. Regarding the preferred embodiment, the content already mentioned above relating to the use according to the invention or the fragrance composition according to the invention should be applied mutatis mutandis.

[0103] Advantageously, the scented articles according to the invention are selected from detergents and cleaning agents, body and hair care products, household products, and preferably from perfume extracts, perfumes, eau de toilette, aftershave, cologne, preshave products, cologne pats and scented tissues, acidic, alkaline or neutral detergents, textile fresheners, ironing aids, liquid detergents, laundry powder, laundry pretreatment agents, fabric softeners, laundry soaps, laundry sheets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and shiners, 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 cosmetics, candles, lamp oil, incense sticks, insecticides, insect repellents and fuels.

[0104] Furthermore, for the flavored articles according to the present invention, it is preferred that the content of component (i) is sufficient to enable consumers to perceive a sensory effective amount of one or more aroma notes selected from fruity, floral, juicy, fresh, sweet, and green aromas.

[0105] It is also preferred that the total amount of the compound of formula (I) in the flavored product is 0.00001 to 10% by weight, preferably 0.0001 to 5% by weight, particularly preferably 0.001 to 2% by weight, more preferably 0.005 to 1% by weight, based on the total weight of the product.

[0106] The aforementioned additives, adjuvants, and / or active ingredients are preferably not fragrances. They can be, for example, preservatives, antibacterial agents, chelating agents, detergents, emulsifiers, fats, etc., and are all substances used as additives, adjuvants, and / or active ingredients primarily in the cosmetics industry, particularly in fragrance compositions and household chemical compositions.

[0107] The present invention will be further characterized below through embodiments.

[0108] Example 1: Odor description of preferred fragrance after adding 2,4-dimethyloctyl-2,7-dien-4-ol (isolinalool)

[0109] Table 1: Odor description of added isolinalool. All content indications are by weight percentage.

[0110]

[0111]

[0112]

[0113] Example 2: Aromatic Oil

[0114] Aromatic oil with fruity aroma (mango)

[0115]

[0116] Description of 1% perfume oil in shower gel:

[0117] The addition of isolinalool gives the aromatic oils a natural character. This blend smells more fruity and rounder.

[0118] Aromatic oil with floral notes (magnolia)

[0119]

[0120] Fragrance description of 10% aromatic oil in ethanol / water:

[0121] With the addition of isolinalool, the mixture becomes more natural, and the aroma becomes more floral and rounded.

[0122] Floral fragrance oils

[0123]

[0124]

[0125] Fragrance description of 0.3% aromatic oil in body lotion:

[0126] The addition of isolinalool enhances the floral notes, making the blend more impactful and giving it a rounded, natural aroma impression.

Claims

1. A compound of formula (I) (I) for imparting, modifying and / or enhancing one or more odor notes selected from fruity, floral, juicy, fresh, sweet, green and earthy of at least one fragrance.

2. The use according to claim 1, wherein the one or more odor notes are selected from fruity, floral, juicy, fresh, sweet and green.

3. The use according to claim 2, wherein the fruity odor note is selected from pineapple, apple and / or plum.

4. The use according to claim 2, wherein the floral odor note is selected from jasmine, magnolia, peony, lily of the valley, lily, lilac and / or rose.

5. A flavour composition comprising or consisting of: a compound of formula (I) (I) and at least one further fragrance having one or more odor notes selected from fruity, floral, juicy, fresh, sweet, green and earthy.

6. The fragrance composition according to claim 5, wherein the weight ratio of the total amount of the compound of formula (I) to the total amount of the further fragrance is from 1:1000 to 1:0.

1.

7. The fragrance composition according to claim 5 or 6, wherein the total amount of the compound of formula (I) is from 0.0001 to 99.9 wt.-%, based on the total weight of the fragrance composition.

8. The fragrance composition according to claim 5 or 6, wherein the total amount of the compound of formula (I) in the fragrance composition is an organoleptically effective amount sufficient to impart and / or enhance and / or modify one or more odor notes selected from fruity, floral, juicy, fresh, sweet, green and earthy.

9. The fragrance composition according to claim 8, wherein the one or more odor notes are selected from fruity, floral, juicy, fresh, sweet and green.

10. The fragrance composition according to claim 5 or 6, wherein the at least one further fragrance is selected from terpenes, aldehydes, nitriles, esters, lactones, alcohols and mixtures thereof.

11. The fragrance composition according to claim 5 or 6, wherein the at least one further fragrance is selected from ethyl 2-cyclopentenyl acetate, (E)-1-cyclohexylethyl but-2-enoate, ethyl 2-methylbutanoate, ethyl (2,4-dimethyl-1,3-dioxolan-2-yl)acetate, 4-methylpentan-2-yl (E)-but-2-enoate, (2-cyclopentylcyclopentyl) (E)-but-2-enoate, benzyl alcohol, 5-(3-methylphenyl)pentan-1-ol, benzyl acetate, methyl 3-oxo-2-pentylcyclopentaneacetate, 1-(4-propan-2-ylcyclohexyl)ethanol, 3,7-dimethyloctan-6-ol, gamma-undecalactone, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol and / or mixtures thereof.

12. Use of a fragrance composition according to claim 5 or 6 for imparting, modifying and / or enhancing one or more odor notes selected from fruity, floral, juicy, fresh, sweet, green and earthy.

13. The use according to claim 12, wherein the one or more odor notes are selected from fruity, floral, juicy, fresh, sweet and green.

14. A method for imparting, modifying and / or enhancing one or more odor notes selected from fruity, floral, juicy, fresh, sweet, green and earthy, comprising or consisting of the following steps: (a) providing a compound of formula (I) (I) (b) providing at least one further perfume having one or more olfactory notes selected from the group consisting of fruity, floral, juicy, fresh, sweet, green and earthy, (c) adding the compound of formula (I) to the at least one further perfume in a sensory effective amount sufficient to impart and / or enhance and / or modify one or more olfactory notes selected from the group consisting of fruity, floral, juicy, fresh, sweet, green and earthy.

15. The method according to claim 14, wherein the one or more olfactory notes are selected from the group consisting of fruity, floral, juicy, fresh, sweet, green and earthy.

16. A perfumed article comprising or, consisting of: (i) a perfume composition according to any one of claims 5 to 9 (ii) at least one further perfume, and (iii) one or more further components.

17. The perfumed article according to claim 16, wherein component (iii) is one or more adjuvants and / or active ingredients.

18. The perfumed article according to claim 17, wherein the article is selected from the group consisting of a cosmetic, a personal care article and / or a household article.

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