Combining Linoleum with Fruity and / or Spicy Fragrances

Linolal, a mixture of C13 and C15 aldehydes, is used to enhance and modify fragrance profiles in the perfume industry, effectively improving spicy and fruity notes in existing fragrances, thus addressing the industry's challenge of creating new and appealing scents.

JP2025507508AActive Publication Date: 2025-03-21SYMRISE GMBH & CO KG
View PDF 5 Cites 0 Cited by

Patent Information

Application Number
JP2024543376
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Filing Date
2022-03-09
Publication Date
2025-03-21
Estimated Expiration
2042-03-09

AI Technical Summary

Technical Problem

The perfume industry faces challenges in creating new fragrances that meet consumer demands, as it requires selecting specific fragrance compositions from a vast array of possible structures, and identifying compounds that can modify or enhance existing fragrances to create novel scents is difficult.

Method used

The use of linolal, a mixture of C13 and C15 aldehydes, in combination with other fragrances to impart, modify, and enhance the fragrance profile, particularly by affecting spicy and fruity notes, is proposed.

Benefits of technology

Linolal significantly modifies and enhances the aroma profiles of fragrance compositions, specifically improving spicy and fruity notes without having a fruity or spicy fragrance on its own, thus expanding the fragrance palette with minimal additional compounds.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure 2025507508000001
    Figure 2025507508000001
  • Figure 2025507508000002
    Figure 2025507508000002
  • Figure 2025507508000003
    Figure 2025507508000003
Patent Text Reader

Abstract

To provide compounds that allow for the active modification of known scents and / or improve the fragrance profile even in small amounts, thus increasing the palette of scents offered to consumers. The present invention proposes the use of small amounts of linolal as an enhancer and / or regulator in fragrance compositions in order to positively influence fruity and spicy notes.
Need to check novelty before this filing date? Find Prior Art

Description

[Technical field]

[0001] The present invention relates to the use of linolal as a fragrance enhancer, modifier and / or imparter.Furthermore, the present invention relates to fragrance compositions, their uses and methods for imparting, modifying and / or enhancing specific fragrance notes. [Background technology]

[0002] In the perfume industry, there is a constant need to develop new fragrances to expand the olfactory palette and satisfy consumer demands. However, the creation of new fragrances or fragrance compositions entails many challenges. For example, it is necessary to select a small number of specific compositions of fragrances from an almost unlimited number of possible structures known from the prior art in order to prepare a product that meets the specific needs of the market and matches the profile required by the customer. It is possible.

[0003] Combining multiple known fragrances can create a scent that consumers perceive as novel and exciting. This process requires combining multiple compounds for one product. However, the cost of the basic ingredients of fragrances and fragrance compositions is high, and as a result, the perfume industry is interested in utilizing fragrances as efficiently as possible. Adding more compounds to already known fragrances to create new scents is an effective way to enhance the scent palette. Compounds that enhance or modify new or known fragrances or compositions are in high demand because the resulting products can have superior properties in terms of the overall perception of the scent. However, it is difficult to identify compounds or compositions that modify and / or enhance the scent profile of known fragrances or fragrance compositions to create new scents. Currently, it is not possible to match compounds based on chemical structure alone to create a pleasant scent. Therefore, rigorous testing of fragrance combinations and concentrations by industry experts is required to identify new candidates. In particular, the identification of additional compounds that can modify known fragrances by providing trace amounts of the additional compounds is highly desirable, since the addition of the compounds may create a large number of new scents from known fragrances or fragrance compositions. This method is cost-effective, since only small amounts are required to enhance and / or modify already known scents. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Patent Publication 2008-19441 Summary of the Invention [Means for solving the problem]

[0005] Thus, the objective underlying the present invention is to provide compounds which allow the active modification of known scents and / or enhance the fragrance profile even in small amounts, thus increasing the palette of scents offered to the consumer. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0006] This is solved by using linolal in combination with at least one other fragrance to impart, modify and / or enhance the odor profile of the fragrance composition.

[0007] Linolal is a mixture of C13 and C15 aldehydes.

[0008] In a preferred embodiment, the C13 and C15 aldehydes are present in a weight ratio of about 1:100 to about 100:1.

[0009] In a preferred embodiment, linolal is a mixture of compounds according to CAS number 93821-14-8.

[0010] In a preferred embodiment, linolal is the hydroformylation product of C12 to C14 alkenes.

[0011] In a preferred embodiment, the linolal is a reaction mass of pentadecanal, tridecanal, 2-methyldodecanal and 2-methyltetradecanal.

[0012] Linolal is known in the fragrance industry and its fragrance profile is described as consisting of aldehydes, fatty, coniferous and floral notes.

[0013] Surprisingly, it has been found that the addition of a small amount of linolal to a fragrance composition significantly changes the odor profile of the composition in a positive way. In particular, the spicy and / or fruity notes of the fragrance composition are affected by the addition of linolal. The addition of a small amount of linolal has been shown to modify the fruity notes already present in the fragrance composition, imparting in particular the sensation of notes associated with watermelon, raspberry, banana, pear, apricot, peach, mandarin peel, and citrus. Similarly, spicy notes are also positively influenced by the addition of linolal, imparting in particular the sensation of almond, coriander, basil, bergamot peel, eucalyptus, pepper, cinnamon, cassia, bay oil, caraway, anise, and cardamom. However, these results are particularly surprising, since linolal does not have a fruity or spicy odor by itself, and has not been described to affect the odor characteristics of fragrance compositions that promote such odors.

[0014] In connection with the preferred use for imparting, modifying and / or enhancing fragrance notes, it is recognized that linolal performs an excellent function as a so-called booster.

[0015] Even more surprisingly, small amounts of linolal were able to enhance already present spicy and / or fruity notes of the fragrance composition.

[0016] In the context of the preferred uses according to the invention, linolal is used in an effective sensory amount, which is the total amount (=active amount) required to provide a sensory effect, either alone or in combination with further compounds or compositions.

[0017] In a preferred embodiment, linolal is used with at least one fragrance and / or composition to create a fragrance composition. Said fragrance composition can be obtained by methods known in the art, such as simple mixing or homogenization of the ingredients. The at least one other fragrance and / or composition can be any other fragrance or composition.

[0018] Thus, the present invention relates to the use of linolal and at least one further compound and / or composition as a fragrance composition, wherein the linolal is contained in an organoleptically effective amount sufficient to impart, modify and / or enhance the fruity and / or spicy notes of an existing fragrance.

[0019] In a preferred embodiment of the present invention, the fruity notes are selected from the group consisting of watermelon, raspberry, banana, pear, apricot, peach, mandarin peel, and citrus.

[0020] In a preferred embodiment of the present invention, the spicy notes are selected from the group consisting of almond, coriander, basil, bergamot peel, eucalyptus, pepper, cinnamon, cassia, bay oil, caraway, anise, and cardamom.

[0021] Linolal can be used in a variety of products and can be particularly advantageously combined with other fragrances in different ratios to form fragrance mixtures, which can lead to the creation of new and unique perfume compositions. Thus, one aspect of the present invention relates to fragrance mixtures that include linolal and, optionally, further components, such as solvents.

[0022] In preferred embodiments of the present invention, the amount of linolal ranges from 0.00001 to 99.9% by weight, more preferably from 0.001 to 5% by weight, and most preferably from 0.05 to 1% by weight, based on the total weight of the fragrance composition.

[0023] In a preferred embodiment of the invention, the weight ratio of linolal to the total amount of other fragrances ranges from 1:100,000 to 1:20, more preferably from 1:20,000 to 1:1,000.

[0024] Examples of fragrances which may be advantageously combined with linolal in the context of the present 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 ei a / ., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001.

[0025] These include: Extracts from natural sources such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures, etc.: e.g. Ambergris Tincture;Amyris Oil;Angelica Seed Oil;Angelica Root Oil;Anise Oil;Valerian Oil;Basil Oil;Tree Moss Absolute;Bay Oil;Mugwort Oil;Benzoelectin;Bergamot Oil;Beeswax Absolute;Birch Tar Oil;Bitter Almond Oil;Savory Oil;Bucco Leaf Oil;Cabreuva Oil;Cade Oil;Calmus Oil;Camphor Oil;Cananga Oil;Cardamom Oil;Cascarilla Oil;Cassia Oil;Cassie Absolute;Castreum Absolute t;Cedar Leaf Oil;Cedarwood Oil;Cistus Oil;Citronella Oil;Citron Oil;Copaiba Balsam;Copaiba Balsam Oil;Coriander Oil;Costus Root Oil;Cumin Oil;Cypress Oil;Davana Oil;Dill Herb Oil;Dill Seed Oil;Hors d'oeuvre Absolute;Oak Moss Absolute;Elemi Oil;Tarragon Oil;Eucalyptus Citriodora Oil;Eucalyptus Oil;Fennel Oil;Spruce Needle Oil;Galbanum Oil;Galbanum Tree Oil;Geranium Oil;Grapefruit Root oil;Guaiacwood oil;Gurjun balsam;Gurjun balsam oil;Helichrysum absolute;Helichrysum oil;Ginger oil;Iris root absolute;Iris root oil;Jasmine absolute;Calamus oil;Blue chamomile oil;Roman chamomile oil;Carrot seed oil;Cascarilla oil;Pine needle oil;Spearmint oil;Caraway oil;Labdanum oil;Labdanum absolute;Labdanum resin;Lavandin absolute;Lavandin oil;Labe underwood absolute;lavender oil;lemongrass oil;lovage oil;distilled lime oil;pressed lime oil;linaloe oil;littose cuba oil;bay leaf oil;mace oil;marjoram oil;mandarin oil;masoir bark oil;mimosa absolute;musk grain oil;musk tincture;muscat sage oil;nutmeg oil;myrrh absolute;myrrh oil;myrrh oil;myrrh oil;myrtle oil;clove leaf oil;clove flower oil;neroli oil;olibanum absolute;olibanum oil;Opopanax oil;Orange blossom absolute;Orange oil;Peppermint oil;Pepper oil;Allspice oil;Pine oil;Pauly oil;Rose absolute;Rosewood oil;Rose oil;Rosemary oil;Dalmatian sage oil;Spanish sage oil;Sandalwood oil;Celery seed oil;Spicy lavender oil;Star anise oil;Styrax oil;Tagetes oil;Fir needle oil;Tea tree oil;Turpentine oil;Thyme oil;Tolu balsam;Tonkabi psol;Tuberose absolute;Vanilla extract;Violet leaf absolute;Verbena oil;Vetiver oil;Juniper berry oil;Wine yeast oil;Wormwood oil;Wintergreen oil;Ylang oil;Hyssop oil;Civet absolute;Cinnamon leaf oil;Cinnamon bark oil and fractions thereof or components isolated therefrom.;

[0026] Individual odorants from the hydrocarbon group, e.g., 3-carene; α-pinene; s-pinene; a-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane; Individual odorants from the group of aliphatic alcohols, such as, for example, 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-methyleneheptan-2-ol; (E,Z)-2,6-nonadienol; 3,7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol; Individual odorants from the group of aliphatic aldehydes and their acetals, such as, for example, 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 diethyl acetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; 1-( 1 -methoxy-propoxy)-(E / Z)-3-hexene; Individual odorants from the group of aliphatic ketones and their oximes, for example, 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-οη; 6-methyl-5-hepten-2-one; Individual odorants from the group of aliphatic sulfur-containing compounds, such as, for example, 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthen-8-thiol; Individual odorants from the group of aliphatic nitriles, for example, 2-nonenoic acid nitrile; 2-undecenoic acid nitrile; 2-tridecenoic acid nitrile; 3,12-tridecadienoic acid nitrile; 3,7-dimethyl-2,6-octadienoic acid nitrile; 3,7-dimethyl-6-octenoic acid nitrile; Individual odorants from the group of esters of aliphatic carboxylic acids, such as, for example, (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-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; (E)- and (Z)-3-hexenyl isobutyrate. Hexyl crotonate;Ethyl isovalerate;Ethyl 2-methylpentanoate;Ethyl hexanoate;Allyl hexanoate;Ethyl heptanoate;Allyl heptanoate;Ethyl octanoate;Ethyl (E,Z)-2,4-decadienoate;Methyl 2-octynate;Methyl 2-nonynate;Allyl 2-isoamyloxyacetate;Methyl 1-3,7-dimethyl-2,6-octadien-eoate;4-Methyl-2-pentylcrotonate; Individual odorants from the group of acyclic terpene alcohols, such as geraniol; nerol; lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-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-Dimethyloct-6-en-1-ol; (2E)-3,7-Dimethylocta-2,6-dien-1-ol; 3,7-Dimethyl-1,5,7-octatrien-3-ol; 2,6-Dimethyl-2,5J-octatrien-1-ol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates; Individual odorants from the group of acyclic terpene aldehydes and ketones, such as 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranylacetone; dimethyl acetal and diethyl acetal of geranial and neral; Individual odorants from the group of cyclic terpene alcohols, such as menthol; isopulegol; α-terpineol; terpinenol-4; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambrinol; vetiverol; guaiol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglates, 3-methyl-2-butenoates; Individual odorants from the group of cyclic terpene aldehydes and ketones, for example, menthone; isomenthone; 8-mercaptomenthan-3-οη; carvone; camphor; fenchone; α-ionone; β-ionone; α-n-methylionone; β-n-methylionone; α-isomethylionone; β-isomethylionone; α-irone; β-damascenone; 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-methanonaphthalen-8(5H)-one; 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; nootkatone; dihydronootkatone; 4,6,8-Megastigmatriene-3-οη;α-Sinensal;β-Sinensal;Acetylated Cedarwood Oil (Methyl Cedryl Ketone); Individual odorants from the group of cyclic alcohols, for example, 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isocamphylcyclohexanol; 2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol; 2-isobutyl-4-m-ethyltetrahydro-2H-pyran-4-ol; 4-cyclohexylbutan-2-ol; Individual odorants from the group of cycloaliphatic alcohols, such as, for example, α,3,3-trimethylcyclohexylmethanol; 1-(4-propylcyclohexyl)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-cyclopent-1-yl)-4-penten-2-ol; 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 1-(2,2,6-trimethylcyclohexyl)pentan-3-ol; 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol; Individual odorants from the group of cyclic and cycloaliphatic ethers, such as, for example, cineol; cedryl methyl ether; cyclododecyl methyl ether; 1,1-dimethoxycyclododecane; (ethoxymethoxy)cyclododecane; α-cedrene epoxide; 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan; 1,5,9-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene; rose oxide; 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-m-ethyl-5-(1-methylpropyl)-1,3-d ioxane; Individual odorants from the group of cyclic and macrocyclic ketones, such as, for example, 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-cyclopenten-1-one; 3-Methyl-5-cyclopentadecenone;3-Methylcyclopentadecanone;4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone;4-tert-pentylcyclohexanone;5-Cyclohexadecen-1-one;6,7-Dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone;8-Cyclohexadecen-1-one;9-Cycloheptadecen-1-οη;Cyclopentadecanone;Cyclohexadecanone; Individual odorants from the group of cycloaliphatic aldehydes, such as 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde; 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde; Individual odorants from the group of cycloaliphatic ketones, such as, for example, 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-naphthalenyl methyl ketone; methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl-(2,4-dimethyl-3-cyclohexen-1-yl) ketone; Individual odorants from the group of esters of cyclic alcohols, for example, 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-Cyclopentyl cyclopentyl crotonate;3-pentyltetrahydro-2H-pyran-4-yl acetate;decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5,resp.6-indenyl acetate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5,or 6-indenyl propionate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5,or 6-indenyl isobutyrate;4,7-methanooctahydro-5,or 6-indenyl acetate; Individual odorants from the group of esters of cycloaliphatic alcohols, for example, 1-cyclohexylethyl crotonate; Individual odorants from the group of esters of cycloaliphatic carboxylic acids, such as, for example, allyl 3-cyclohexylpropionate; allyl cyclohexyloxyacetate; glacial trans-methyl dihydrojasmonate; glacial trans-methyl jasmonate; 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-acetate; Individual odorants from the group of aliphatic alcohols, for example, benzyl alcohol; 2-phenylethanol; 1-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3-(3-methylphenyl)propanol; 1,1-dimethyl-2-phenylethyl alcohol; 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; Individual odorants from the group of esters of aliphatic alcohols and aliphatic carboxylic acids, for example: benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; α-trichloromethylbenzyl acetate; α,α-dimethylphenylethyl acetate; α,α-dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate; Individual odorants from the group of aliphatic ethers, for example, 2-phenylethyl methyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl 1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; hydratropaldehyde dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxine; 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxine; Individual odorants from the group of aromatic and aliphatic aldehydes, for example: benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; hydratropaldehyde; 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.butyl-phenyl)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; Individual odorants from the group of aromatic and aliphatic ketones, for example, acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4-(4-hydroxyphenyl)-2-butanone; 1-(2-naphthalenyl)ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl)ethanone; Benzophenone;1,1,2,3,6-Hexamethyl-5-indanyl methyl ketone;6-tert-butyl-1,1-di-methyl-4-indanyl methyl ketone;1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone;5',6',7',8'-Tetrahydro-3',5',6',8',8'-hexamethyl-2-aceto-naphthone; Individual odorants from the group of aromatic and aliphatic carboxylic acids and their esters, for example: benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; phenylethyl acetate; geranyl phenylacetate; phenylethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allylphenoxy cinnamate; methyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenylethyl salicylate; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; 3-phenylethyl glycidenate; 3-methyl-3-phenylethyl glycidenate; Individual odorants from the group of heterocyclic compounds, for example, 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-οη; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one; Individual odorants from the group of lactones, for example, 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide; 4-methyl-1,4-decanolide; 1,15-pentadecanolide; 1,16-Hexadecanolide;9-Hexadecen-1,16-olide;10-Oxa-1,16-hexadecanolide;1-1-Oxa-1,16-hexadecanolide;12-Oxa-1,16-hexadecanolide;Ethylene-1,12-dodecanedioate;Ethylene-1,13-tridecanedioate;2,3-Dihydrocoumarin;Octahydrocoumarin.

[0027] In a preferred embodiment according to the present invention, the at least one other fragrance is selected from the group consisting of: 4-(4-methoxyphenyl)butan-2-one, 3-methylbutyl acetate, hexyl acetate, benzaldehyde, 3,7-dimethylocta-1,6-dien-3-ol, 5-heptyloxolan-2-one, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 2-(4-methyl-1-cyclohex-3-enyl)propan-2-yl acetate, (2E)-3-phenylprop-2-enal, 2-Methoxy-4-(prop-2-en-1-yl)phenol, (Z)-Deca-6-enal, 3-(1-ethoxyethoxy)-3,7-dimethylocta-1,6-diene, Eletaria cardamomum L. seed oil, Pimenta acriscostel leaf oil, Triethyl 2-hydroxypropane-1,2,3-tricarboxylate, 3-ethoxy-4-hydroxybenzaldehyde, Phenylmethanol, Cinnamomum moniliforme bark oil le, Pepper L. Fruit Oil Black, Benzyl (2E)-3-Phenylprop-2-enoate, 3-Phenylpropan-1-ol, Cinnamon L. Leaf Oil, Myristica Fragrance Hout, Fruit Oil, 5-Pentyloxolan-2-one, (2E)-3,7-Dimethylocta-2,6-dien-1-ol, Ethyl Acetate, 4-Hydroxy-3-Methoxybenzaldehyde, (E)-4-(2,6,6-Trimethyl- 1-Cyclohex-2-enyl)but-3-en-2-one, 4-oxa-2,6-heptanediol and 4-oxa-1,6-heptanediol, Egonochiton chinensis kleib ex Hartweiss resin, 2,4-dimethylcyclohex-3-ene-1-carbaldehyde, benzyl acetate, (2-tert-butylcyclohexyl)acetate, ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate.

[0028] The fragrance composition according to the present invention consists of or comprises linolal and at least one further compound or composition, wherein the linolal is present in an organoleptically effective amount sufficient to impart, modify and / or enhance the fruity and / or spicy notes of an existing fragrance.

[0029] Preferably, the fragrance composition according to the invention consists of or comprises linolal and two or more additional fragrances. More preferably, the fragrance composition according to the invention consists of or comprises linolal and three or more additional fragrances. Most preferably, the fragrance composition according to the invention consists of or comprises linolal and four or more additional fragrances.

[0030] Perfume oil compositions (=fragrance mixtures, compositions) containing linolal are advantageously used in perfumery in liquid form, either undiluted or diluted with a solvent. Suitable solvents for this are, for example, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.

[0031] Furthermore, the fragrance composition according to the invention can be adsorbed on a carrier that ensures both a fine distribution of the fragrance in the product and a controlled release during use.Such carriers can be porous inorganic materials such as light sulfates, silica gel, zeolites, plaster, clay, clay granules, aerated concrete, etc., or organic materials such as wood, cellulosic materials, sugar, dextrins (e.g. maltodextrin) or plastics such as PVC, polyvinyl acetate or polyurethane.The resulting combination of the composition according to the invention and the carrier material is also understood as the fragrance composition according to the invention.

[0032] The fragrance compositions according to the invention can also be added in this form, for example as microencapsulated, spray dried, inclusion complexes or as extruded products, to the product to be perfumed.

[0033] If necessary, the properties of the composition thus modified can be further optimized with a view to a more targeted release of the fragrance by so-called "coating" with a suitable material, for which purpose waxy plastics such as polyvinyl alcohol are preferably used. The product thus obtained is the moulded article according to the invention.

[0034] The fragrance compositions according to the invention can be advantageously used in the form of concentrates, solutions or modifications as mentioned above for the manufacture of fragrances according to the invention, such as perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, preshave products, splash colognes and scented refreshment towels, as well as acidic, alkaline and neutral cleaning agents, such as floor cleaners, window cleaners, dishwashing detergents, bathroom and sanitary cleaners, abrasive emulsions, solid and liquid toilet cleaners, powder and foam carpet cleaners, textile fresheners, ironing aids, liquid detergents, powder detergents, ironing aids, laundry pretreatments such as bleaches, soaking agents, stain removers, fabric softeners, laundry soaps, laundry tablets, disinfectants. Air fresheners in liquid, gel or solid carrier form, aerosol sprays, waxes and polishes such as furniture polish, floor wax and shoe cream, personal care products such as bar and liquid soaps, shower gels, shampoos, shaving soaps and shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil cosmetic emulsions, such as skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, suntan creams and lotions, hair care products such as hairsprays and hair gels, These products include hair sprays, hair gels, hair lotions, hair conditioners, permanent hair dyes, semi-permanent hair dyes, hair shaping products such as cold wave and hair straightening, hair lotions, hair creams, hair lotions, deodorants and antiperspirants such as underarm sprays, roll-ons, deodorant sticks and deodorant creams, decorative cosmetics such as eye shadows, nail polish, lipsticks and mascara, candles, lamp oil, incense, insecticides, repellents and fuel.

[0035] Of course, the fragrance composition according to the invention can also be included in a cosmetic or household composition.

[0036] Another aspect of the present invention relates to a method for modifying and / or enhancing an existing fragrance, for imparting, modifying and / or enhancing the fruity and / or spicy notes of said fragrance, comprising or consisting of the following steps: a. providing linol; b. providing at least one additional fragrance; and c. adding to the at least one additional fragrance a sensory effective amount of linolal sufficient to impart, modify and / or enhance the fruity and / or spicy notes of the existing fragrance.

[0037] A further aspect of the present invention relates to a scented product comprising or consisting of linolal and at least one additional fragrance compound, the linolal being present in an organoleptically effective amount sufficient to impart, modify and / or enhance the fruity and / or spicy notes of an existing fragrance.

[0038] In a preferred embodiment, the perfumed product is selected from cosmetics, hygiene products and / or household products. The further preferred embodiments listed above also apply to the perfumed products of the present invention.

[0039] Preferably, the scented household product is selected from the group consisting of detergents and cleaning agents, hygiene or care products, preferably products in the field of body and hair care, cosmetics and household products, preferably fragrance extracts, eau de parfum, eau de toilette, aftershave lotions, eau de cologne, preshave products, splash cologne, scented refreshing tissues, acidic, alkaline or neutral cleaning agents, fabric fresheners, ironing aids, liquid detergents, washing powders, laundry pretreatments, fabric softeners, wash tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, personal care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, suntan creams and lotions, hair care products, decorative cosmetics, candles, lamp oils, incense, insecticides, repellents and fuels. Most preferably, the scented product is selected from alcohol perfumes, personal hygiene products or cleaning or care products for use in the home.

[0040] The above-mentioned additives, auxiliaries and / or active substances are preferably not odoriferous substances. They can be, for example, preservatives, antibacterial agents, chelating agents, detergents, emulsifiers, oils and fats, etc., and in principle, all substances that are used as additives, auxiliaries and / or active ingredients in cosmetic products, especially fragrance compositions, and household compositions.

[0041] The further preferred embodiments listed above also apply to the scented products of the present invention.

[0042] In the following, the invention will be further characterized on the basis of examples. EXAMPLES

[0043] Examples 1-13: <Effect of trace amounts of linol on fragrance compositions>

[0044] To investigate the effect of linolal in enhancing or modifying the odor profile, known fragrance compounds or compositions were mixed with a working amount of linolal. The resulting odor changes are reported in Table 1, as compared to compositions without linolal. The amount of linolal is given as a weight percent of the total composition.

[0045] Table 1: The addition of trace amounts of linoleic acid enhances and modifies the fragrance profile. [Table 1]

[0046] These data indicate that linolal has a strong impact on fragrance compositions to modify and enhance already present notes.

[0047] Example 14: <Fragrance composition containing a small amount of linol> Table 2: Fragrance mixtures [Table 2]

[0048] According to the expert panel, the linoleum ingredient gives this fruity scent even more juiciness and enhances the natural peach notes with its sparkling effect, enhancing the overall fragrance and revealing a more spectacular fruity profile. Example 15: <Fragrance composition containing a small amount of linol>

[0049] Table 3: Fragrance mixtures [Table 3]

[0050] According to the expert panel, the metallic notes of Linolal give the sparkling cinnamon note a boost, making it more impactful. Overall, it enhances all the spiciness of the fragrance and can be used as a trail to power the spicy top notes.

[0051] The examples presented clearly show the impact of trace amounts of linolal in modifying and enhancing particularly spicy and fruity notes in fragrance compositions.

Claims

1. The use of linolal and at least one further compound and / or composition in a fragrance composition, comprising The use wherein linolal is used in an organoleptically effective amount sufficient to impart, modify and / or enhance the fruity and / or spicy notes of an existing fragrance.

2. 2. The use according to claim 1, wherein the fruity notes are selected from the group consisting of watermelon, raspberry, banana, pear, apricot, peach, mandarin peel and citrus.

3. 3. Use according to claim 1 or claim 2, wherein the spicy notes are selected from the group consisting of almond, coriander, basil, bergamot peel, eucalyptus, pepper, cinnamon, cassia, bay oil, caraway, anise and cardamom.

4. 4. The use according to claim 1, wherein the at least one further compound is selected from the group consisting of: 4-(4-methoxyphenyl)butan-2-one, 3-methylbutyl acetate, hexyl acetate, benzaldehyde, 3,7-dimethylocta-1,6-dien-3-ol, 5-heptyloxolan-2-one, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 2-(4-methyl-1-cyclohex-3-enyl)propan-2-yl acetate, (2E)-3-phenylprop-2-enal , 2-Methoxy-4-(prop-2-en-1-yl)phenol, (Z)-Deca-6-enal, 3-(1-ethoxyethoxy)-3,7-dimethylocta-1,6-diene, Eletaria cardamomum L. seed oil, Pimenta acriscostel leaf oil, Triethyl 2-hydroxypropane-1,2,3-tricarboxylate, 3-ethoxy-4-hydroxybenzaldehyde, Phenylmethanol, Cinnamon bark Oil, Peppermint Fruit Oil Black, Benzyl (2E)-3-Phenylprop-2-enoate, 3-Phenylpropan-1-ol, Cinnamon Leaf Oil, Myristica Fragrans Hout, Fruit Oil, 5-Pentyloxolan-2-one, (2E)-3,7-Dimethylocta-2,6-dien-1-ol, Ethyl Acetate, 4-Hydroxy-3-Methoxybenzaldehyde, (E)-4-(2,6,6-Trimethyl-1 -cyclohex-2-enyl)but-3-en-2-one, 4-oxa-2,6-heptanediol and 4-oxa-1,6-heptanediol, egonochiton chinensis kleib ex Hartweiss resin, 2,4-dimethylcyclohex-3-ene-1-carbaldehyde, benzyl acetate, (2-tert-butylcyclohexyl)acetate, ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate.

5. 5. Use according to at least one of claims 1 to 4, in which the amount of linolal ranges from 0.001 to 5% by weight, based on the total weight of the fragrance composition.

6. 5. Use according to at least one of claims 1 to 4, in which the amount of linolal ranges from 0.05 to 1% by weight, based on the total weight of the fragrance composition.

7. 5. Use according to at least one of claims 1 to 4, in which the weight ratio of linolal to the total amount of other fragrances ranges from 1:100,000 to 1:

20.

8. Use according to at least one of claims 1 to 4, in which the weight ratio of linolal to the total amount of other fragrances ranges from 1:20000 to 1:1000.

9. A fragrance composition comprising or consisting of linolal and at least one further compound, A fragrance composition comprising linolal in an organoleptically effective amount sufficient to impart, modify and / or enhance the fruity and / or spicy notes of an existing fragrance.

10. 10. The fragrance composition of claim 9, wherein the amount of linolal ranges from 0.001 to 5% by weight, based on the total weight of the fragrance composition.

11. 10. The fragrance composition of claim 9, wherein the weight ratio of linolal to the total amount of other fragrances ranges from 1:100,000 to 1:

20.

12. A method for modifying and / or enhancing an existing fragrance, for imparting, modifying and / or enhancing the fruity and / or spicy notes of said fragrance, said method comprising or consisting of the following steps: a. providing linol; b. providing at least one additional fragrance; and c) adding to the at least one additional fragrance an organoleptically effective amount of linolal sufficient to impart, modify and / or enhance the fruity and / or spicy notes of the existing fragrance.

13. 13. The method of claim 12, wherein the amount of linolal ranges from 0.001 to 5% by weight, based on the total weight of the fragrance composition.

14. 13. The method of claim 12, wherein the weight ratio of linolal to the total amount of other fragrances ranges from 1:100,000 to 1:

20.

15. A scented product comprising or consisting of linol and at least one further fragrance compound, A scented product comprising linolal in an organoleptically effective amount sufficient to impart, modify and / or enhance the fruity and / or spicy notes of an existing fragrance.

Citation Information

Patent Citations

  • Cyclopentylcyanomethylcyclopentene compound, preparation thereof, and use thereof as fragrant substance

    JP1993140071A

  • Musk-scented esters and their use in fragrances

    JP2002524438A

  • Citrus-note perfume composition

    JP2004168936A

  • FRAGRANCE EXHALING SUBSTANCE AND AROMATIC SUBSTANCE COMPRISING ALDEHYDE HAVING ALKYL RESIDUE SUBSTITUTED AT alpha-POSITION

    JP2008019441A

  • Isomer mixtures of unsaturated macrocyclic musk compounds

    US20170211014A1