Dihydroavenanthramide d for reducing fragrance degradation
Dihydroavenanthramide D stabilizes fragrances in cosmetic and pharmaceutical preparations by preventing oxidative degradation, ensuring consistent scent quality during storage and transportation.
Patent Information
- Application Number
- PCT/EP2024/057146
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2024-03-18
- Publication Date
- 2025-09-25
AI Technical Summary
Fragrances in cosmetic and pharmaceutical preparations are prone to degradation during storage and transportation, leading to reduced or unpleasant odors, which consumers find unacceptable, and methods to prevent this degradation without impairing the preparations' effects are needed.
The use of Dihydroavenanthramide D, its pharmaceutically or cosmetically acceptable salts, or solvates, to stabilize fragrances by reducing or preventing their degradation, particularly in aldehydes, alcohols, esters, and ketones, through mechanisms such as oxidative stabilization.
Dihydroavenanthramide D effectively maintains the fragrance's olfactory impression and intensity over extended periods, reducing degradation and maintaining the original scent profile.
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Abstract
Description
[0001] Dihydroavenanthramide D for reducing fragrance degradation
[0002] The present invention relates to the use of Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof for reducing or preventing the degradation of one or more fragrance(s), to a method for reducing or preventing the degradation of one or more fragrance(s) and to a fragrance composition comprising one or more fragrance(s) and Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof.
[0003] Fragrances play an important role in the cosmetic industry and are commonly admixed to various cosmetic preparations. Likewise, also in the pharmaceutical industry, fragrances are used and incorporated into pharmaceutical preparations. Cosmetic preparations and pharmaceutical preparations are sold in all regions in the world. Thus, from their production in one place to their final application by e.g. a consumer in any other place, there is a long way of transportation, which acts on the cosmetic preparations and pharmaceutical preparations. The steps of transportation and the steps in between typically include long times of storing the cosmetic preparations and pharmaceutical prep- arations. Additionally, different conditions, such as the temperature, are acting on the stored / transported preparations. Consequently, after their initial production, cosmetic preparations and pharmaceutical preparations are subject to different conditions over a long time until they reach and are applied by the final consumer.
[0004] Such conditions have been found to negatively affect the fragrance(s) included in such preparations. Very often, the fragrance(s) are degraded to other compounds during storage and transportation. Such other compounds may have none or a reduced odour compared to the original compound or which may even have another odour, which is perceived as unpleasant odour by consumers.
[0005] Even though the function of a cosmetic preparation or a pharmaceutical preparation might still be the same or only insignificantly less than directly after its production, most consumers do not accept products with a reduced odour or with an unpleasant odour.
[0006] Thus, after storing and transporting the preparations, their original odour may be less intense and / or may comprise further, often unpleasant notes, which needs to be avoided.
[0007] However, reducing the time of storage and transport or completely avoiding conditions affecting the preparations is typically not an option.
[0008] There is thus a need of a solution to reduce or prevent the degradation of fragrances.
[0009] Preferably, such a solution may be used in a cosmetic or pharmaceutical preparation and thus does not impair the effect, which shall be provided with the cosmetic or pharmaceutical preparation. Advantageously, such a solution rather promotes or increases the effect, which shall be provided with the cosmetic or pharmaceutical preparation.
[0010] The primary object of the present invention was thus to provide a possibility for reducing or preventing the degradation of one or more fragrance(s).
[0011] The primary object of the present invention is solved by the use of Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof for reducing or preventing the degradation of one or more fragrance(s) selected from the group consisting of aldehydes, alcohols, esters, ketones or ethers. Dihydroavenanthramide D has been used e.g. in cosmetic preparations. However, it was surprisingly found that Dihydroavenanthramide D is able to reduce or, respectively, prevent the degradation of fragrances, particularly fragrances selected from aldehydes, alcohols, esters, ketones or ethers. After subjecting a mixture comprising fragrances to an artificial process of aging and degrading fragrances, the amount of the fragrances was much higher or even unaffected by the process when Dihydroavenanthramide D was present, compared to the same mixture, which did not contain Dihydroavenanthramide D.
[0012] Such an effect of Dihydroavenanthramide D was not known and was thus surprising.
[0013] Thus, Dihydroavenanthramide D can be used to prevent or reduce the degradation of fragrances, for example the fragrances in cosmetic preparations or pharmaceutical preparations. Therefore, the fragrances or, respectively, compositions or preparations comprising fragrances are less vulnerable with regard to storage and transportation when Dihydroavenanthramide D is added.
[0014] Preferably, unless stated otherwise, all features and effects described herein for Dihydroav- enanthramide D apply accordingly for the pharmaceutically or cosmetically acceptable salt(s) and / or solvates thereof.
[0015] Dihydroavenanthramide D is a compound with particular importance in the cosmetic industry. Dihydroavenanthramide D belongs to the family of Avenanthramides, i.e. anthranilic acid amides, and is also described as hydroxyphenyl propamidobenzoic acid. Dihydroavenanthramide D is described by the CAS number 697235-49-7 (as listed by the European Chemicals Agency) and corresponds to the following chemical structure:
[0016] Dihydroavenanthramide D
[0017] Preferably, the term “Dihydroavenanthramide D” includes the compound according to the chemical structure above, as well as its keto-enol tautomers and isomers thereof. Dihydroavenanthramide D has been described for several cosmetic applications. For example, WO 2006 / 134013 A1 describes an application of Dihydroavenanthramide D for alleviating itching and / or for reducing skin reddening.
[0018] US 2006 / 089413 A1 describes that Dihydroavenanthramide D can be used forthe inhibition of the substance P-induced release of histamine from mast cells. In this way, pruritus, skin reddening, weal development or allergic skin reactions may be prevented.
[0019] Preferably, the term “salt of Dihydroavenanthramide D”, as used herein, refers to pharmaceutically or cosmetically acceptable salts of Dihydroavenanthramide D. Particularly preferably, the term refers to or includes alkali metal and alkaline earth metal salts of Dihydroavenanthramide D, especially preferably the sodium or potassium salts of Dihydroavenanthramide D and mixtures thereof.
[0020] Preferably, the term “solvate of Dihydroavenanthramide D”, as used herein, refers to pharmaceutically or cosmetically acceptable salts of Dihydroavenanthramide D. Particularly preferably, the term refers to or includes the solvates of Dihydroavenanthramide D in a diol.
[0021] Preferably, the term “degradation of a fragrance”, as used herein, refers to the chemical conversion of the fragrance compound to another compound (i.e. the degraded compound). Preferably, the term “degradation of a fragrance”, as used herein, refers to the oxidative conversion of the fragrance, preferably to autoxidation of the fragrance. Preferably the term “another compound”, as used herein, also includes stereoisomers. Preferably the term “another compound”, as used herein, does not include stereoisomers.
[0022] Typically, the degradation of a compound (e.g. fragrance) can be detected by measuring the amount of the compound (e.g. fragrance) at different time points. Such a measurement may be performed by mass spectrometry. In case the amount is reduced in a later time point (compared to an earlier time point), the compound (e.g. fragrance) is degraded.
[0023] Typically, a degraded compound (e.g. fragrance) has a different olfactory characteristic than the original compound (e.g. fragrance). Usually, the different olfactory characteristic is perceived as an impairment of the olfactory characteristic. However, for some compounds (e.g. fragrances), a degraded compound (e.g. fragrance) may have similar or equal olfactory characteristics. Preferably, the, one, two, three or more or all fragrance(s) is / are selected from the group consisting of group A.
[0024] 2,4-Dimethylcyclohex-3-ene-1-carbaldehyde, Ethyl acetoacetate, (Z)-Hex-3-en-1-yl methyl carbonate, Linalool, Linalyl acetate, Cyclohexanol, 2-(1 ,1-dimethylethyl)-ac- etate, Methyl-2-octinoat, (2E)-3,7-Dimethylocta-2,6-dienal, 3,7-dimethyloct-6-en-1- ol, 2,6,10-Trimethylundec-9-enal, 3-(o-Ethylphenyl)-2,2-dimethylpropionalde- hydeand3-(p-Ethylphenyl)-2,2-dimethylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, (Ethoxymethoxy)cyclododecane, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcyclopent-3-en-1-yl) but-2-en-1-ol, 3a,6,6,9a-Tetra- methyldodecahydronaphtho[2,1-b]furan, Gamma-Undecalactone, cis-3-Hexenyl salicylate, Pentadecan-15-olide, (5E)-3-Methyl-5-cyclopentadecen-1-one, 3-Methyl-5- cyclopentadecen-1-one, (4E)-3-Methyl-4-cyclopentadecen-1-one, 1 ,3,4,6,7,8-Hexa- hydro-4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, a-Hexyl cinnamalde- hyde, Oxacycloheptadec-10-en-2-one, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin, ethylene brassylate, and trans-2,cis-6-Nonadienal, benzyl acetate, phenoxyethyl isobutyrate, p-tert. butyl cyclohexylacetate, linalyl acetate, dimethyl benzyl carbinyl acetate, phenyl ethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl phenyl glycinate, allyl cyclohexyl propionate, styrallyl propionate, benzyl salicylate, benzyl ethyl ether, linear alkanals containing 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxy-citronellal, lilial and bourgeonal, ionones, isomethylionone and methyl cedryl ketone, anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, terpenes, balsams, sage oil, camomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, limeblossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, la- danum oil and lavandin oil, bergamot oil, dihydromyrcenol, lilial, lyral, phenylethyl alcohol, hexylcinnamaldehyde, benzyl acetone, Boisambrene Forte, Ambroxan, indole, hedione, sandelice, citrus oil, mandarin oil, orange oil, allylamyl glycolate, cy- clovertal, lavandin oil, clary sage oil, damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Super, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, rose oxide, romillat, irotyl, floramate, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, and methyl-, ethyl-esters thereof, l-hexene-3-one, l-heptene-3-one, 1-octen-3-one, I- nonene-3-one, l-decene-3-one, octalactone, 1 -hexene, 1 -heptene, 1 -octene, 1-non- ene, 1 -decene, 2-ethyl-l-butene, 2-ethyl-l-pentene, 2-ethyl-l-hexene, 2-ethyl-l-hep- tene, 2-ethyl-l-octene, cis-3-methyl-2-pentene, cis-3-methyl-2-hexene, cis-3-methyl- 2-heptene, cis-3-methyl-2-octene, cis-3-methyl-2-nonene, trans-3-methyl-2-pen- tene, trans-3-methyl-2-hexene, trans-3-methyl-2-heptene, trans-3-methyl-2-octene, trans-3-methyl-2-nonene, cis-2-hexene, cis-2-heptene, cis-2-octene, cis-2-nonene, cis-2-decene, trans-2-hexene, trans-2-heptene, trans-2-octene, trans-2-nonene, trans-2-decene, cis-3-hexene, cis-3-heptene, cis-3-octene, cis-3-nonene, cis-3-de- cene, trans-3-hexene, trans-3-heptene, trans-3-octene, trans-3-nonene, trans-3-de- cene.
[0025] Particularly preferably, the, one, two, three or more or all fragrance(s) is / are selected from the group consisting of group B.
[0026] Group B:
[0027] 2,4-Dimethylcyclohex-3-ene-1-carbaldehyde, Ethyl acetoacetate, (Z)-Hex-3-en-1-yl methyl carbonate, Linalool, Linalyl acetate, Cyclohexanol, 2-(1 ,1-dimethylethyl)-ac- etate, Methyl-2-octinoat, (2E)-3,7-Dimethylocta-2,6-dienal, 3,7-dimethyloct-6-en-1- ol, 2,6,10-Trimethylundec-9-enal, 3-(o-Ethylphenyl)-2,2-dimethylpropionalde- hydeand3-(p-Ethylphenyl)-2,2-dimethylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, (Ethoxymethoxy)cyclododecane, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcyclopent-3-en-1-yl) but-2-en-1-ol, 3a,6,6,9a-Tetra- methyldodecahydronaphtho[2,1-b]furan", Gamma-Undecalactone, cis-3-Hexenyl salicylate, Pentadecan-15-olide, (5E)-3-Methyl-5-cyclopentadecen-1-one, 3-Methyl- 5-cyclopentadecen-1-one, (4E)-3-Methyl-4-cyclopentadecen-1-one, 1 ,3, 4, 6, 7, 8- Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, a-Hexyl cinnamal- dehyde, Oxacycloheptadec-10-en-2-one, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpro- panal, Ethylvanillin, Vanillin, ethylene brassylate, and trans-2,cis-6-Nonadienal.
[0028] Particularly preferably, the, one, two, three or more or all fragrance(s) is / are selected from the group consisting of group C.
[0029] Group C:
[0030] 2,4-Dimethylcyclohex-3-ene-1-carbaldehyde, Linalool, Linalyl acetate, (2E)-3,7-Di- methylocta-2,6-dienal, 3,7-dimethyloct-6-en-1-ol, 2,6,10-Trimethylundec-9-enal, 3- (o-Ethylphenyl)-2,2-dimethylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-dime- thylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcyclopent-3-en-1-yl) but-2-en-1-ol, 1 ,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, a- Hexyl cinnamaldehyde, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin,
[0031] Vanillin.
[0032] Preferably, the compounds listed above are described under the following names or, respectively, INCI names, and CAS numbers. Preferably, the CAS numbers are those as listed by the CAS Common Chemistry (https: / / commonchemistry.cas.org / ).
[0033]
[0034] The surprising effect of Dihydroavenanthramide D, as described herein is particularly advantageous for stabilizing one or more fragrances in a fragrance composition. Thus, Dihydroavenanthramide D can be used to prevent or reduce the degradation of fragrances, for example the fragrances in cosmetic preparations or pharmaceutical preparations. Therefore, the fragrances or, respectively, compositions or preparations comprising fragrances are less vulnerable with regard to storage and transportation when Dihydroavenanthramide D is added.
[0035] Therefore, it is preferred in the use according to the invention that the degradation is reduced or prevented in a fragrance composition, preferably comprising the one or more fragrance^).
[0036] Preferably in the use according to the invention, the degradation is reduced or prevented in a fragrance composition comprising one, two, three or more or all fragrances selected from the group consisting of group A.
[0037] Preferably in the use according to the invention, the degradation is reduced or prevented in a fragrance composition comprising one, two, three or more or all fragrances selected from the group consisting of group B.
[0038] Preferably in the use according to the invention, the degradation is reduced or prevented in a fragrance composition comprising one, two, three or more or all fragrances selected from the group consisting of consisting of group C.
[0039] Moreover, it is preferred in the use according to the invention that the degradation is reduced or prevented in a cosmetic or pharmaceutical preparation, preferably comprising the one or more fragrance(s).
[0040] Preferably in the use according to the invention, the degradation is reduced or prevented in a cosmetic or pharmaceutical preparation comprising one, two, three or more or all fragrances selected from the group consisting of group A. Preferably in the use according to the invention, the degradation is reduced or prevented in a cosmetic or pharmaceutical preparation comprising one, two, three or more or all fragrances selected from the group consisting of group B.
[0041] Preferably in the use according to the invention, the degradation is reduced or prevented in a cosmetic or pharmaceutical preparation comprising one, two, three or more or all fragrances selected from the group consisting of consisting of group C.
[0042] What is described herein for fragrance compositions, particularly with regard to the use and method according to the invention, applies accordingly to cosmetic or pharmaceutical preparations, where applicable.
[0043] As described herein, Dihydroavenanthramide D can prevent or reduce the degradation of fragrance(s), wherein the degraded fragrance often provides a different, usually impaired, olfactory impression. Thus, Dihydroavenanthramide D is able to stabilize the olfactory impression of a fragrance composition.
[0044] This effect of Dihydroavenanthramide D was not known and was surprising, since Dihydroavenanthramide D itself may provide an unpleasant glue-like olfactory impression under certain conditions.
[0045] Preferably, the term “stabilizing an olfactory impression”, as used herein, describes that the olfactory impression of e.g. a composition is not or not significantly altered when comparing the composition at different time points. Preferably, the term “stabilizing an olfactory impression”, as used herein, describes that the intensity of the olfactory impression of e.g. a composition is not or not significantly reduced when comparing the composition at different time points.
[0046] It is thus preferred in the use according to the invention that an olfactory impression of the fragrance composition or the cosmetic or pharmaceutical preparation is stabilized, preferably wherein the decrease of the intensity of the olfactory impression is reduced or prevented.
[0047] Preferably, the term “the decrease of the intensity of the olfactory impression is reduced or prevented” refers to a comparison of two fragrance compositions or cosmetic or pharma- ceutical preparations, which differ only by that one of the compositions comprises Dihy- droavenanthramide D. The two compositions or preparations are stored and subsequently analysed. In this case, a decrease of the intensity of the olfactory impression is reduced or prevented in case the observed decrease in the composition or preparation comprising Dihydroavenanthramide D is less than the observed decrease in the composition or preparation not comprising Dihydroavenanthramide D.
[0048] Whether an olfactory impression is altered or not (e.g. stabilized or not) may be determined by a trained panel evaluating the olfactory impression, for example by evaluating olfactory descriptors on a numeric scale, which is well-known to a skilled person. For example, a composition is produced and stored for a certain time. After storage, the same composition is produced again and the freshly produced composition as well as the stored composition are compared by olfactory evaluation.
[0049] Preferably, the olfactory impression is stabilized for at least 2 weeks, preferably at least 4 weeks, preferably at least 6 weeks, preferably at least 8 weeks, preferably at least 10 weeks, preferably at least 12 weeks, preferably at least 4 months, preferably at least 5 months, preferably at least 6 months, preferably at least 7 months, preferably at least 8 months, preferably at least 9 months, preferably at least 10 months, preferably at least 11 months, preferably at least 12 months, preferably at least 15 months, preferably at least 18 months, preferably at least 24 months.
[0050] Preferably, during the time, in which the olfactory impression of e.g. a composition is stabilized, the temperature of the e.g. composition does not exceed 70 °C, preferably 65 °C, preferably 60 °C, preferably 55 °C, preferably 50 °C, preferably 45 °C, preferably 40 °C, preferably 35 °C, preferably 30 °C.
[0051] It is preferred in the use according to the invention that the amount of Dihydroavenanthramide D and / or the pharmaceutically or cosmetically acceptable salt and / or solvate thereof in the fragrance composition is in the range of from 0.0005 to 25 wt.-%, preferably in the range of from 0.00075 to 22.5 wt.-%, preferably in the range of from 0.001 to 20 wt.- %, preferably in the range of from 0.0025 to 17.5 wt.-%, preferably in the range of from 0.005 to 15 wt.-%, preferably in the range of from 0.0075 to 12.5 wt.-%, preferably in the range of from 0.01 to 10 wt.-%, preferably in the range of from 0.025 to 7.5 wt.-%, preferably in the range of from 0.05 to 5 wt.-%, based on the total weight of the fragrance composition. It is preferred in the use according to the invention that the amount of Dihydroavenan- thramide D and / or the pharmaceutically or cosmetically acceptable salt and / or solvate thereof in the cosmetic or pharmaceutical preparation is in the range of from 0.0001 to 10 wt.-%, preferably in the range of from 0.0005 to 5 wt.-%, preferably in the range of from 0.00075 to 2.5 wt.-%, preferably in the range of from 0.001 to 1 wt.-%, preferably in the range of from 0.0025 to 0.5, preferably in the range of from 0.005 to 0.2 wt.-%, preferably in the range of from 0.01 to 0.1 wt.-%, based on the total weight of the preparation.
[0052] It is preferred in the use according to the invention that the weight ratio of the Dihydroav- enanthramide D and / or the pharmaceutically or cosmetically acceptable salt and / or solvate thereof in the fragrance composition or cosmetic or pharmaceutical preparation to the fragrance^) is in a range of from 500:1 to 1 :30,000, preferably in a range of from 250:1 to 1 :10,000, further preferably in a range of from 100:1 to 1 :1 ,000, particularly preferably of from 10:1 to 1 :100, especially preferably of from 5:1 to 1 :5, even further preferably of from 2:1 to 1 :2, more preferably of from 1.5:1 to 1 :1.5.
[0053] Preferably, for determining the amount of Dihydroavenanthramide D and / or the pharmaceutically or cosmetically acceptable salt and / or solvate thereof in the composition or preparation, the summed weights of Dihydroavenanthramide D and the salt and the solvate thereof in the composition or preparation are considered. In case one of the above is not present in the composition or preparation, its weight is considered as 0 g.
[0054] Preferably, the amount of frag rance (s) in the composition is in the range of from 50 to 99 wt.-%, preferably of from 60 to 97.5 wt.-%, particularly preferably of from 70 to 95 wt.-%, further preferably of from 75 to 92.5 wt.-%, especially preferably of from 80 to 90 wt.-%, based on the total weight of the composition.
[0055] Preferably, the amount of frag rance (s) in the cosmetic or pharmaceutical preparation is in the range of from 0.001 to 3 wt.-%, preferably of from 0.005 to 2 wt.-%, particularly preferably of from 0.01 to 1 .75 wt.-%, further preferably of from 0.05 to 1 .5 wt.-%, based on the total weight of the cosmetic or pharmaceutical preparation.
[0056] It is preferred that the term “the amount of frag rance (s)” refers to the fragrances selected from the group consisting of group A, preferably selected from the group consisting of group B, preferably selected from the group consisting of group C, wherein preferably the summed weights of all of these fragrance(s) are considered for determining the amount. In case a fragrance is not present in the mixture, its weight is considered as 0 g.
[0057] The present invention further relates to a method for reducing or preventing the degradation of one or more or fragrance(s), comprising the steps i) selecting one or more fragrance(s), of which the degradation shall be reduced or prevented, wherein the, one, two, three or more or all fragrance(s) is / are selected from the group consisting of aldehydes, alcohols, esters, ketones or ethers, ii) providing the fragrance(s) selected in step i) iii) providing Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof iv) mixing the components provided in step ii) and iii).
[0058] What was said herein with regard to the use according to the invention applies accordingly to the method according to the invention, particularly with regard to the preferred features.
[0059] Preferably, the term “selecting one or more fragrance(s)” in step i) refers to identifying one or more fragrance(s).
[0060] Preferably, the step of providing Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof in step iii) of the method according to the invention refers to providing Dihydroavenanthramide D or a pharmaceutically or cosmetically acceptable salt or a solvate thereof or a combination thereof. Such a combination includes a combination of the mentioned alternatives but also a combination of several possibilities of one alternative (as well as the combination of the above). For example, such a combination includes providing Dihydroavenanthramide D and a pharmaceutically or cosmetically acceptable salt thereof, but also providing two different pharmaceutically or cosmetically acceptable salts of Dihydroavenanthramide D. Additionally or alternatively, the step of providing Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof may refer to providing a composition comprising providing Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof or a combination thereof. It is preferred in the method according to the invention that the, one, two, three or more or all fragrance(s) selected in step i) is / are selected from the group consisting of group A.
[0061] It is preferred in the method according to the invention that the, one, two, three or more or all fragrance(s) selected in step i) is / are selected from the group consisting of group B.
[0062] It is preferred in the method according to the invention that the, one, two, three or more or all fragrance(s) selected in step i) is / are selected from the group consisting of group C.
[0063] The present invention further relates to a method for stabilizing an olfactory impression of a fragrance composition or a cosmetic or pharmaceutical preparation, wherein the fragrance composition or cosmetic or pharmaceutical preparation comprises one, two, three or more or all fragrance(s) selected from the group consisting of group A, comprising the steps a) selecting a fragrance composition or cosmetic or pharmaceutical preparation, of which the degradation shall be reduced or prevented, b) providing the fragrance composition or cosmetic or pharmaceutical preparation selected in step a), c) providing Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof, d) mixing the fragrance composition or cosmetic or pharmaceutical preparation provided in step b) and the Dihydroavenanthramide D and / or pharmaceutically or cosmetically acceptable salt and / or solvate thereof provided in step c).
[0064] Preferably, the term “selecting one or more fragrance(s)” in step a) refers to identifying one or more fragrance(s). Preferably, the step of providing Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof in step c) of the method according to the invention refers to providing Dihydroavenanthramide D or a pharmaceutically or cosmetically acceptable salt or a solvate thereof or a combination thereof. Such a combination includes a combination of the mentioned alternatives but also a combination of several possibilities of one alternative (as well as the combination of the above). For example, such a combination includes providing Dihydroavenanthramide D and a pharmaceutically or cosmetically acceptable salt thereof, but also providing two different pharmaceutically or cosmetically acceptable salts of Dihydroavenanthramide D.
[0065] Additionally or alternatively, the step of providing Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof may refer to providing a composition comprising providing Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof or a combination thereof.
[0066] It is preferred in the method according to the invention that the fragrance composition or cosmetic or pharmaceutical preparation comprises one, two, three or more or all fragrance^) selected from the group consisting of group B, preferably selected from the group consisting of group C.
[0067] Preferably, the composition obtained in step iv) or, respectively, d) of the method according to the invention is a fragrance composition, as described herein. What is said herein with regard to a fragrance composition, especially the preferred features, apply accordingly to the fragrance composition obtained in step iv) or, respectively, d) of the method according to the invention.
[0068] Preferably, the composition obtained in step iv) or, respectively, d) of the method according to the invention is a cosmetic or pharmaceutical preparation, as described herein. What is said herein with regard to a cosmetic or pharmaceutical preparation, especially the preferred features, apply accordingly to the cosmetic or pharmaceutical preparation obtained in step iv) or, respectively, d) of the method according to the invention.
[0069] It is preferred in the method according to the invention that the amount of Dihydroavenanthramide D and / or the pharmaceutically or cosmetically acceptable salt and / or solvate thereof in the composition obtained in step iv) or, respectively, d) of the method according to the invention is in the range of from 0.0005 to 25 wt.-%, preferably in the range of from 0.00075 to 22.5 wt.-%, preferably in the range of from 0.001 to 20 wt.-%, preferably in the range of from 0.0025 to 17.5 wt.-%, preferably in the range of from 0.005 to 15 wt.-%, preferably in the range of from 0.0075 to 12.5 wt.-%, preferably in the range of from 0.01 to 10 wt.-%, preferably in the range of from 0.025 to 7.5 wt.-%, preferably in the range of from 0.05 to 5 wt.-%, based on the total weight of the composition. It is preferred that said composition is a fragrance composition.
[0070] It is preferred in the method according to the invention that the amount of Dihydroavenan- thramide D and / or the pharmaceutically or cosmetically acceptable salt and / or solvate thereof in the composition obtained in step iv) or, respectively, d) of the method according to the invention is in the range of from 0.0001 to 10 wt.-%, preferably in the range of from 0.0005 to 5 wt.-%, preferably in the range of from 0.00075 to 2.5 wt.-%, preferably in the range of from 0.001 to 1 wt.-%, preferably in the range of from 0.0025 to 0.5, preferably in the range of from 0.005 to 0.2 wt.-%, preferably in the range of from 0.01 to 0.1 wt.-%, based on the total weight of the composition. It is preferred that said composition is a fragrance composition, or a cosmetic or pharmaceutical preparation.
[0071] It is preferred in the method according to the invention that the weight ratio of the Dihy- droavenanthramide D and / or the pharmaceutically or cosmetically acceptable salt and / or solvate thereof in the composition obtained in step iv) or, respectively, d) of the method according to the invention to the fragrance(s) is in a range of from 500:1 to 1 :30,000, preferably in a range of from 250:1 to 1 :10,000, further preferably in a range of from 100:1 to 1 :1 ,000, particularly preferably of from 10:1 to 1 :100, especially preferably of from 5:1 to 1 :5, even further preferably of from 2:1 to 1 :2, more preferably of from 1 .5:1 to 1 :1 .5.
[0072] Preferably, the amount of frag rance (s) in the composition obtained in step iv) or, respectively, d) of the method according to the invention is in the range of from 50 to 99 wt.-%, preferably of from 60 to 97.5 wt.-%, particularly preferably of from 70 to 95 wt.-%, further preferably of from 75 to 92.5 wt.-%, especially preferably of from 80 to 90 wt.-%, based on the total weight of the composition. It is preferred that said composition is a fragrance composition.
[0073] Preferably, the amount of frag rance (s) in the composition obtained in step iv) or, respectively, d) of the method according to the invention is in the range of from 0.001 to 3 wt.-%, preferably of from 0.005 to 2 wt.-%, particularly preferably of from 0.01 to 1 .75 wt.-%, further preferably of from 0.05 to 1.5 wt.-%, based on the total weight of the composition. It is preferred that said composition is a fragrance composition, or a cosmetic or pharmaceutical preparation.
[0074] Preferably, for determining the amount of Dihydroavenanthramide D and / or the pharmaceutically or cosmetically acceptable salt and / or solvate thereof in the composition or preparation, the summed weights of Dihydroavenanthramide D and the salt and the solvate thereof in the composition or preparation are considered. In case one of the above is not present in the composition or preparation, its weight is considered as 0 g.
[0075] It is preferred that the term “the amount of frag rance (s)” refers to the fragrances selected from the group consisting of group A, preferably selected from the group consisting of group B, preferably selected from the group consisting of group C, wherein preferably the summed weights of all of these fragrance(s) are considered for determining the amount. In case a fragrance is not present in the mixture, its weight is considered as 0 g.
[0076] The present invention further relates to a fragrance composition comprising a) one or more fragrance(s) selected from the group consisting of aldehydes, alcohols, esters, ketones or ethers, and b) Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof, wherein the peroxide value of the fragrance composition is at least 0.25 mmol / L, preferably at least 0.5 mmol / L, based on the total volume of the fragrance composition, and wherein the peroxide value of the fragrance composition is at most 70 %, preferably at most 65 %, further preferably at most 60 %, particularly preferably at most 55 % of the peroxide value of the same composition without component b).
[0077] The peroxide value preferably describes the amount of peroxides per 1 Liter of a composition. Peroxides are compounds with the structure R-O-O-R, wherein R is any element. Typically, when fragrances are degraded, oxidative processes are involved or responsible for the degradation. Usually, fragrances are degraded by autoxidation, which preferably refers to the gradual degradation of organic compounds in air at ambient temperatures (e.g. in the range of from 20 to 30 °C) due to oxidation.
[0078] The peroxide value thus indicates how much degradation has already occurred in a composition.
[0079] It was surprisingly found that the addition of Dihydroavenanthramide D reduced the peroxide value in a fragrance composition to approximately 50 % compared to the same composition but without Dihydroavenanthramide D. Thus, Dihydroavenanthramide D prevents or reduces the degradation of the fragrances in the fragrance composition, as described herein.
[0080] Nevertheless, even with Dihydroavenanthramide D, the degradation of the fragrances in a fragrance composition cannot be fully prevented for all time. Thus, the degradation of the fragrances occurs, however to only a minor extent.
[0081] A fragrance composition with a peroxide value of at least 0.25 mmol / L has thus undergone some degradation and thus does not describe a fragrance composition immediately after its production.
[0082] Preferably, the peroxide value of a fragrance composition may be determined by visual titration. Preferably, for such a visual titration, a sample is treated with acetic acid and a suitable organic solvent (preferably with a mixture of acetic acid and the suitable organic solvent) and subsequently a solution of potassium iodide. The resulting iodine may then be titrated with a standard solution of sodium thiosulfate to determine the peroxide value.
[0083] What was said above with regard to the use according to the invention or with regard to the method according to the invention applies accordingly to the fragrance composition according to the invention, particularly with regard to preferred features.
[0084] It is preferred in the fragrance composition according to the invention that the composition comprises compound b) in the range of from 0.0005 to 25 wt.-%, preferably in the range of from 0.00075 to 22.5 wt.-%, preferably in the range of from 0.001 to 20 wt.-%, preferably in the range of from 0.0025 to 17.5 wt.-%, preferably in the range of from 0.005 to 15 wt.-%, preferably in the range of from 0.0075 to 12.5 wt.-%, preferably in the range of from 0.01 to 10 wt.-%, preferably in the range of from 0.025 to 7.5 wt.-%, preferably in the range of from 0.05 to 5 wt.-%, based on the total weight of the composition.
[0085] Preferably, for determining the amount of Dihydroavenanthramide D and / or the salt and / or solvate thereof (i.e. compound b)) in the composition, the summed weights of Dihydroavenanthramide D and the salt and the solvate thereof in the composition are considered. In case one of the above is not present in the composition, its weight is considered as 0 g.
[0086] It is preferred in the fragrance composition according to the invention that the composition comprises compound a) in the range of from 50 to 99 wt.-%, preferably of from 60 to 97.5 wt.-%, particularly preferably of from 70 to 95 wt.-%, further preferably of from 75 to 92.5 wt.-%, especially preferably of from 80 to 90 wt.-%, based on the total weight of the composition.
[0087] It is preferred in the fragrance composition according to the invention that the weight ratio of compound b) to compound a) is in a range of from 500:1 to 1 :30,000, preferably in a range of from 250:1 to 1 :10,000, further preferably in a range of from 100:1 to 1 :1 ,000, particularly preferably of from 10:1 to 1 :100, especially preferably of from 5:1 to 1 :5, even further preferably of from 2:1 to 1 :2, more preferably of from 1 .5:1 to 1 :1 .5.
[0088] It is preferred in the fragrance composition according to the invention that the, one, two, three or more or all fragrance(s) of component a) is / are selected from the group consisting of group A.
[0089] It is further preferred in the fragrance composition according to the invention that the, one, two, three or more or all fragrance(s) of component a) is / are selected from the group consisting of group B, preferably selected from the group consisting of group C.
[0090] The present invention further relates to a cosmetic or pharmaceutical preparation comprising a fragrance composition according to the invention.
[0091] Cosmetic preparation, as described herein, are in particular preparations, which are suitable for topical application to the skin of a human, in particular to achieve a cosmetic effect. Preferably, pharmaceutical preparations according to the invention are in the form of capsules, tablets (uncoated and coated tablets, for example having coatings resistant to gastric juices), sugar-coated tablets, granules, pellets, mixtures of solids, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other swallowable or chewable preparations and are preferably used as medicines only available by prescription, from pharmacies or other medicines or as food supplements.
[0092] Cosmetic preparations or pharmaceutical preparations, as described herein, may further comprise one, two, three or more or all substances selected from the group consisting of odoriferous substances, perfume oils, fatty oils, fatty acids, ceramides, pseudoceramides, sterols, hydrocarbons phytosterols, anti-acne active ingredients, antidandruff active ingredients, antimicrobial active ingredients, preservatives, antiperspirants, anti-irritants, pruritus-relieving active ingredients, cooling active ingredients, antiaging active ingredients, skin-lightening and skin-tanning active ingredients, skin moisture regulators, osmolytes, insect repellents, enzyme inhibitors, odour absorbers, dyes, abrasives, anti-acne agents, anti-cellulitis agents, antidandruff agents, anti-inflammatory agents, irritation-preventing agents, irritation-inhibiting agents, antioxidants, astringents, perspiration-inhibiting agents, antiseptic agents, ant-statics, binders, buffers, carrier materials, chelating agents, cell stimulants, cleansing agents, care agents, depilatory agents, surface-active substances, deodorizing agents, antiperspirants, softeners, emulsifiers, enzymes, essential oils, fibres, filmforming agents, fixatives, foam-forming agents, foam stabilizers, substances for preventing foaming, foam boosters, gelling agents, gel-forming agents, hair care agents, hair-setting agents, hair-straightening agents, moisture-donating agents, moisturizing substances, moisture-retaining substances, bleaching agents, strengthening agents, stain-removing agents, optically brightening agents, impregnating agents, dirtrepellent agents, friction-reducing agents, lubricants, moisturizing creams, ointments, opacifying agents, plasticizing agents, covering agents, polish, gloss agents, polymers, powders, proteins, re-oiling agents, abrading agents, silicones, skin-soothing agents, skin-cleansing agents, skin care agents, skin-healing agents, skin-lightening agents, skin-protecting agents, skin-softening agents, hair promotion agents, cooling agents, skin-cooling agents, warming agents, skinwarming agents, stabilizers, UV-absorbing agents, UV filters, detergents, fabric conditioning agents, suspending agents, skin-tanning agents, thickeners, vitamins, oils, waxes, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, a-hydroxy acids, poly hydroxyfatty acids, liquefiers, dyestuffs, colour-protecting agents, pigments, anticorrosives, aromas, flavouring substances, odoriferous substances, polyols, surfactants, electrolytes, organic solvents, and silicone derivatives. Preferably, the amount of Dihydroavenanthramide D and / or the pharmaceutically or cosmetically acceptable salt and / or solvate thereof in the preparation according to the invention is in the range of from 0.0001 to 10 wt.-%, preferably in the range of from 0.0005 to 5 wt.-%, preferably in the range of from 0.00075 to 2.5 wt.-%, preferably in the range of from 0.001 to 1 wt.-%, preferably in the range of from 0.0025 to 0.5, preferably in the range of from 0.005 to 0.2 wt.-%, preferably in the range of from 0.01 to 0.1 wt.-%, based on the total weight of the preparation.
[0093] It was surprisingly found that within these ranges, Dihydroavenanthramide D and / or the salt and / or solvate thereof provides the effects as described herein, but does not yet provide a glue-like olfactory impression.
[0094] Preferably, for determining the amount of Dihydroavenanthramide D and / or the salt and / or solvate thereof in the preparation according to the invention, the summed weights of Dihydroavenanthramide D and the salt and the solvate thereof in the preparation are considered. In case one of the above is not present in the preparation, its weight is considered as o g.
[0095] Preferably, the amount of fragrance(s) in the preparation is in the range of from 0.001 to 3 wt.-%, preferably of from 0.005 to 2 wt.-%, particularly preferably of from 0.01 to 1 .75 wt.- %, further preferably of from 0.05 to 1 .5 wt.-%, based on the total weight of the preparation.
[0096] It is preferred in the preparation according to the invention that the weight ratio of the Dihydroavenanthramide D and / or the pharmaceutically or cosmetically acceptable salt and / or solvate thereof to the fragrance(s) is in a range of from 500:1 to 1 :30,000, preferably in a range of from 250:1 to 1 :10,000, further preferably in a range of from 100:1 to 1 :1 ,000, particularly preferably of from 10:1 to 1 :100, especially preferably of from 5:1 to 1 :5, even further preferably of from 2:1 to 1 :2, more preferably of from 1 .5:1 to 1 :1 .5.
[0097] It is preferred that the term “the amount of frag rance (s)” refers to the fragrances selected from the group consisting of group A, preferably selected from the group consisting of group B, preferably selected from the group consisting of group C, wherein preferably the summed weights of all of these fragrance(s) are considered for determining the amount. In case a fragrance is not present in the mixture, its weight is considered as 0 g.
[0098] Further aspects and advantages of the invention result from the subsequent description of preferred examples.
[0099] Examples
[0100] Example 1 : Fragrance degradation
[0101] A fragrance composition comprising the fragrances was prepared.
[0102] Dihydroavenanthramide D was added to the composition to obtain composition A, comprising a concentration of Dihydroavenanthramide D of 0.1 wt.-%.
[0103] Composition A and the same composition but without Dihydroavenanthramide D (control) were subjected to an artificial aging process. The artificial aging process was applied by subjecting the compositions to 70 °C and 5 bar for 24 h.
[0104] For artificial aging, the samples were aged by a ML OXIPRES ©that is designed to monitor the oxidation based on the consumption of oxygen at elevated temperatures and pressure.
[0105] A sample is weighed into a glass vessel and placed into the pressure vessel. The vessel is flushed with oxygen and a pressure of 5 bar is applied. The vessels are placed in the block heater and heated to 70 °C for 24 hours.
[0106] After the artificial aging process, the ingredients of the composition were analysed by mass spectrometry (GC-MS) using Biphenyl as an internal standard.
[0107] In the composition without Dihydroavenanthramide D (control), the total amount of the fragrances described above was reduced to 71 % (average, with 100 % being the initially admixed amounts).
[0108] In contrast, in the composition comprising Dihydroavenanthramide D, the total amount of the fragrances described above was only reduced to 98 % (average, with 100 % being the initially admixed amounts).
[0109] t was surprisingly found that the addition of Dihydroavenanthramide remarkably prevented reduced the degradation of the fragrances in the composition. Example 2: Peroxide value
[0110] A composition comprising was prepared and Dihydroavenanthramide was added to obtain composition B, comprising a concentration of Dihydroavenanthramide D of 0.1 wt.-%.
[0111] Composition B and the same composition but without Dihydroavenanthramide D (control) were subjected to an artificial aging process, as described in Example 1 .
[0112] The peroxide values were obtained by treating the corresponding sample with a mixture of acetic acid and a suitable organic solvent and then a solution of potassium iodide. The resulting iodine with titrated with a standard solution of sodium thiosulfate to determine the peroxide value.
[0113] A sample (3.0 g) was dissolved in acetic acid and chloroform 3:2 (50 mL) in a 250 ml Er- lenmeyer flask, a freshly prepared potassium iodide solution (1 mL) was added and allowed to react for 1 minute while stirring the solution vigorously. Then, distilled water (100 mL) was added and titration was done immediately with sodium thiosulfate solution from a purple to a slight yellow or colorless endpoint. A blank titration was carried out under the same conditions.
[0114] The peroxide value can be calculated using the consumption of the two titrations.
[0115] The peroxide value of the control was 476.64 mmol / L.
[0116] In contrast, the peroxide value of composition B was 18.06 mmol / L.
[0117] Adding Dihydroavenanthramide D to the composition surprisingly resulted in a decrease of the peroxide value after the aging process to only 3 % of the peroxide value of the control (i.e. reduction by 97 %).
[0118] Example 3: Peroxide value
[0119] The initial composition of Example 2 was prepared. A 3 % dilution in neutral oil was prepared to provide a composition representing a cosmetic composition. Dihydroavenanthramide was added to obtain composition C, comprising a concentration of Dihydroavenanthramide D of 0.05 wt.-%.
[0120] Composition C and the same composition but without Dihydroavenanthramide D (control) were subjected to an artificial aging process, as described in Example 1 . The peroxide values were measured as described in Example 2.
[0121] The peroxide value of the control was 2.57 mmol / L.
[0122] In contrast, the peroxide value of composition C was 1 .33 mmol / L.
[0123] Adding Dihydroavenanthramide D to the composition surprisingly resulted in a decrease of the peroxide value after the aging process to only 52 % of the peroxide value of the control (i.e. reduction by 48 %).
Claims
Claims1. Use of Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof for reducing or preventing the degradation of one or more fragrance(s) selected from the group consisting of aldehydes, alcohols, esters, ketones or ethers.
2. Use according to claim 1 , wherein the, one, two, three or more or all fragrance(s) is / are selected from the group consisting of 2,4-Dimethylcyclohex-3-ene-1-carbalde- hyde, Ethyl acetoacetate, (Z)-Hex-3-en-1-yl methyl carbonate, Linalool, Linalyl acetate, Cyclohexanol, 2-(1 ,1-dimethylethyl)-acetate, Methyl-2-octinoat, (2E)-3,7-Dime- thylocta-2,6-dienal, 3,7-dimethyloct-6-en-1-ol, 2,6,10-Trimethylundec-9-enal, 3-(o- Ethylphenyl)-2,2-dimethylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-dime- thylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, (Eth- oxymethoxy)cyclododecane, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcyclo- pent-3-en-1-yl) but-2-en-1-ol, 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]fu- ran, Gamma-Undecalactone, cis-3-Hexenyl salicylate, Pentadecan-15-olide, (5E)-3- Methyl-5-cyclopentadecen-1-one, 3-Methyl-5-cyclopentadecen-1-one, (4E)-3-Me- thyl-4-cyclopentadecen-1-one, 1 ,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cy- clopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, Oxacycloheptadec-10-en-2- one, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin, ethylene brassylate, and trans-2,cis-6-Nonadienal, benzyl acetate, phenoxyethyl isobutyrate, p-tert.butyl cyclohexylacetate, linalyl acetate, dimethyl benzyl carbinyl acetate, phenyl ethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl phenyl glycinate, allyl cyclohexyl propionate, styrallyl propionate, benzyl salicylate, benzyl ethyl ether, linear alkanals containing 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetal- dehyde, cyclamen aldehyde, hydroxy-citronellal, lilial and bourgeonal, ionones, isomethylionone and methyl cedryl ketone, anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, terpenes, balsams, sage oil, camomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, limeblossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, ladanum oil and lavandin oil, bergamot oil, dihydromyrcenol, lilial, lyral, phenylethyl alcohol, hexylcinnamaldehyde, benzyl acetone, Boisambrene Forte, Ambroxan, indole, hedione, sandelice, citrus oil, mandarin oil, orange oil, allylamyl glycolate, cyclovertal, lavandin oil, clary sage oil, damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Su- per, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, roseoxide, romillat, irotyl, floramate, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, and methyl-, ethyl-esters thereof, l-hex- ene-3-one, l-heptene-3-one, 1-octen-3-one, l-nonene-3-one, l-decene-3-one, octalactone, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 2-ethyl-l-butene, 2- ethyl-l-pentene, 2-ethyl-l-hexene, 2-ethyl-l-heptene, 2-ethyl-l-octene, cis-3-methyl-2- pentene, cis-3-methyl-2-hexene, cis-3-methyl-2-heptene, cis-3-methyl-2-octene, cis-3-methyl-2-nonene, trans-3-methyl-2-pentene, trans-3-methyl-2-hexene, trans-3- methyl-2-heptene, trans-3-methyl-2-octene, trans-3-methyl-2-nonene, cis-2-hexene, cis-2-heptene, cis-2-octene, cis-2-nonene, cis-2-decene, trans-2-hexene, trans-2- heptene, trans-2-octene, trans-2-nonene, trans-2-decene, cis-3-hexene, cis-3-hep- tene, cis-3-octene, cis-3-nonene, cis-3-decene, trans-3-hexene, trans-3-heptene, trans-3-octene, trans-3-nonene, trans-3-decene.
3. Use according to any one of the preceding claims, wherein the, one, two, three or more or all fragrance(s) is / are selected from the group consisting of 2,4-Dimethylcy- clohex-3-ene-1-carbaldehyde, Ethyl acetoacetate, (Z)-Hex-3-en-1-yl methyl carbonate, Linalool, Linalyl acetate, Cyclohexanol, 2-(1 ,1-dimethylethyl)-acetate, Me- thyl-2-octinoat, (2E)-3,7-Dimethylocta-2,6-dienal, 3,7-dimethyloct-6-en-1-ol, 2,6,10- Trimethylundec-9-enal, 3-(o-Ethylphenyl)-2,2-dimethylpropionalde-hydeand3-(p- Ethylphenyl)-2,2-dimethylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, (Ethoxymethoxy)cyclododecane, Iso E Gamma, (2E)-2-Ethyl-4- (2,2,3)-trimethylcyclopent-3-en-1-yl) but-2-en-1-ol, 3a,6,6,9a-Tetramethyldodecahy- dronaphtho[2,1-b]furan", Gamma-Undecalactone, cis-3-Hexenyl salicylate, Penta- decan-15-olide, (5E)-3-Methyl-5-cyclopentadecen-1-one, 3-Methyl-5-cyclopentade- cen-1-one, (4E)-3-Methyl-4-cyclopentadecen-1-one, 1 ,3,4,6,7,8-Hexahydro- 4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, Oxacycloheptadec-10-en-2-one, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin, ethylene brassylate, and trans-2,cis-6-Nonadienal, preferably selected from the group consisting of 2,4-Dimethylcyclohex-3-ene-1- carbaldehyde, Linalool, Linalyl acetate, (2E)-3,7-Dimethylocta-2,6-dienal, 3,7-dime- thyloct-6-en-1-ol, 2,6,10-Trimethylundec-9-enal, 3-(o-Ethylphenyl)-2,2-dime- thylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-dimethylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcyclopent-3-en-1-yl) but-2-en-1-ol, 1 ,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, 3- (1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin.
4. Use according to any one of the preceding claims, wherein the degradation is reduced or prevented in a fragrance composition or in a cosmetic or pharmaceutical preparation, comprising the one or more fragrance(s), preferably one, two, three or more or all fragrances as defined in claims 2 or 3.
5. Use according to claim 4, wherein an olfactory impression of the fragrance composition or cosmetic or pharmaceutical preparation is stabilized, preferably wherein the decrease of the intensity of the olfactory impression is reduced or prevented.
6. Method for reducing or preventing the degradation of one or more or fragrance(s), comprising the steps i) selecting one or more fragrance(s), of which the degradation shall be reduced or prevented, wherein the, one, two, three or more or all fragrance(s) is / are selected from the group consisting of aldehydes, alcohols, esters, ketones or ethers, ii) providing the fragrance(s) selected in step i) iii) providing Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof iv) mixing the components provided in step ii) and iii).
7. Method according to claim 6, wherein the, one, two, three or more or all fragrance(s) selected in step i) is / are selected from the group consisting of 2,4-Dimethylcyclohex- 3-ene-1-carbaldehyde, Ethyl acetoacetate, (Z)-Hex-3-en-1-yl methyl carbonate, Linalool, Linalyl acetate, Cyclohexanol, 2-(1 ,1-dimethylethyl)-acetate, Methyl-2-octi- noat, (2E)-3,7-Dimethylocta-2,6-dienal, 3,7-dimethyloct-6-en-1-ol, 2,6,10-Trime- thylundec-9-enal, 3-(o-Ethylphenyl)-2,2-dimethylpropionalde-hydeand3-(p- Ethylphenyl)-2,2-dimethylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, (Ethoxymethoxy)cyclododecane, Iso E Gamma, (2E)-2-Ethyl-4- (2,2,3)-trimethylcyclopent-3-en-1-yl) but-2-en-1-ol, 3a,6,6,9a-Tetramethyldodecahy-dronaphtho[2,1-b]furan, Gamma-Undecalactone, cis-3-Hexenyl salicylate, Pentade- can-15-olide, (5E)-3-Methyl-5-cyclopentadecen-1 -one, 3-Methyl-5-cyclopentade- cen-1-one, (4E)-3-Methyl-4-cyclopentadecen-1-one, 1 ,3,4,6,7,8-Hexahydro- 4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, Oxacycloheptadec-10-en-2-one, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin, ethylene brassylate, and trans-2,cis-6-Nonadienal, benzyl acetate, phenoxyethyl isobutyrate, p-tert.butyl cyclohexylacetate, linalyl acetate, dimethyl benzyl carbinyl acetate, phenyl ethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl phenyl glycinate, allyl cyclohexyl propionate, styrallyl propionate, benzyl salicylate, benzyl ethyl ether, linear alkanals containing 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxy-citronellal, lilial and bourgeonal, ionones, isomethylionone and methyl cedryl ketone, anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, terpenes, balsams, sage oil, camomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, limeblossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, la- danum oil and lavandin oil, bergamot oil, dihydromyrcenol, lilial, lyral, phenylethyl alcohol, hexylcinnamaldehyde, benzyl acetone, Boisambrene Forte, Ambroxan, indole, hedione, sandelice, citrus oil, mandarin oil, orange oil, allylamyl glycolate, cy- clovertal, lavandin oil, clary sage oil, damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Super, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, rose oxide, romillat, irotyl, floramate, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, and methyl-, ethyl-esters thereof, l-hexene-3-one, l-heptene-3-one, 1-octen-3-one, I- nonene-3-one, l-decene-3-one, octalactone, 1 -hexene, 1 -heptene, 1 -octene, 1 -nonene, 1 -decene, 2-ethyl-l-butene, 2-ethyl-l-pentene, 2-ethyl-l-hexene, 2-ethyl-l-hep- tene, 2-ethyl-l-octene, cis-3-methyl-2-pentene, cis-3-methyl-2-hexene, cis-3-methyl- 2-heptene, cis-3-methyl-2-octene, cis-3-methyl-2-nonene, trans-3-methyl-2-pen- tene, trans-3-methyl-2-hexene, trans-3-methyl-2-heptene, trans-3-methyl-2-octene, trans-3-methyl-2-nonene, cis-2-hexene, cis-2-heptene, cis-2-octene, cis-2-nonene, cis-2-decene, trans-2-hexene, trans-2-heptene, trans-2-octene, trans-2-nonene, trans-2-decene, cis-3-hexene, cis-3-heptene, cis-3-octene, cis-3-nonene, cis-3-de- cene, trans-3-hexene, trans-3-heptene, trans-3-octene, trans-3-nonene, trans-3-de- cene.
8. Method according to claim 6 or 7, wherein the, one, two, three or more or all fragrance^) is / are selected from the group consisting of 2,4-Dimethylcyclohex-3-ene- 1-carbaldehyde, Ethyl acetoacetate, (Z)-Hex-3-en-1-yl methyl carbonate, Linalool,Linalyl acetate, Cyclohexanol, 2-(1 ,1-dimethylethyl)-acetate, Methyl-2-octinoat, (2E)-3,7-Dimethylocta-2,6-dienal, 3,7-dimethyloct-6-en-1-ol, 2,6,10-Trimethylundec- 9-enal, 3-(o-Ethylphenyl)-2,2-dimethylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-di- methylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, (Ethoxymethoxy)cyclododecane, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcy- clopent-3-en-1 -yl) but-2-en-1 -ol, 3a,6,6,9a-Tetramethyldodecahydronaphtho[2, 1 - b]furan", Gamma-Undecalactone, cis-3-Hexenyl salicylate, Pentadecan-15-olide, (5E)-3-Methyl-5-cyclopentadecen-1-one, 3-Methyl-5-cyclopentadecen-1-one, (4E)-3-Methyl-4-cyclopentadecen-1-one, 1 ,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl- cyclopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, Oxacycloheptadec-10-en-2- one, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin, ethylene brassylate, and trans-2,cis-6-Nonadienal, preferably selected from the group consisting of 2,4-Dimethylcyclohex-3-ene-1- carbaldehyde, Linalool, Linalyl acetate, (2E)-3,7-Dimethylocta-2,6-dienal, 3,7-dime- thyloct-6-en-1-ol, 2,6,10-Trimethylundec-9-enal, 3-(o-Ethylphenyl)-2,2-dime- thylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-dimethylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcyclopent-3-en-1-yl) but-2-en-1-ol, 1 ,3,4,6,7,8-Hexahydro- 4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, 3- (1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin.
9. Method for stabilizing an olfactory impression of a fragrance composition or a cosmetic or pharmaceutical preparation, wherein the fragrance composition comprises one, two, three or more or all fragrance^) selected from the group consisting of 2,4-Dimethylcyclohex-3-ene-1- carbaldehyde, Ethyl acetoacetate, (Z)-Hex-3-en-1-yl methyl carbonate, Linalool, Linalyl acetate, Cyclohexanol, 2-(1 ,1-dimethylethyl)-acetate, Methyl-2-octinoat, (2E)- 3,7-Dimethylocta-2,6-dienal, 3,7-dimethyloct-6-en-1-ol, 2,6,10-Trimethylundec-9- enal, 3-(o-Ethylphenyl)-2,2-dimethylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-di- methylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, (Ethoxymethoxy)cyclododecane, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcy- clopent-3-en-1 -yl) but-2-en-1 -ol, 3a,6,6,9a-Tetramethyldodecahydronaphtho[2, 1 - b]furan, Gamma-Undecalactone, cis-3-Hexenyl salicylate, Pentadecan-15-olide, (5E)-3-Methyl-5-cyclopentadecen-1-one, 3-Methyl-5-cyclopentadecen-1-one, (4E)- 3-Methyl-4-cyclopentadecen-1-one, 1 ,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, Oxacycloheptadec-10-en-2- one, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin, ethylene brassylate, and trans-2,cis-6-Nonadienal, benzyl acetate, phenoxyethyl isobutyrate, p-tert.butyl cyclohexylacetate, linalyl acetate, dimethyl benzyl carbinyl acetate, phenyl ethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl phenyl glycinate, allyl cyclohexyl propionate, styrallyl propionate, benzyl salicylate, benzyl ethyl ether, linear alkanals containing 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetal- dehyde, cyclamen aldehyde, hydroxy-citronellal, lilial and bourgeonal, ionones, isomethylionone and methyl cedryl ketone, anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, terpenes, balsams, sage oil, camomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, limeblossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, ladanum oil and lavandin oil, bergamot oil, dihydromyrcenol, lilial, lyral, phenylethyl alcohol, hexylcinnamaldehyde, benzyl acetone, Boisambrene Forte, Ambroxan, indole, hedione, sandelice, citrus oil, mandarin oil, orange oil, allylamyl glycolate, cyclovertal, lavandin oil, clary sage oil, damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Su- per, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, rose oxide, romillat, irotyl, floramate, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, and methyl-, ethyl-esters thereof, l-hex- ene-3-one, l-heptene-3-one, 1-octen-3-one, l-nonene-3-one, l-decene-3-one, octalactone, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 2-ethyl-l-butene, 2- ethyl-l-pentene, 2-ethyl-l-hexene, 2-ethyl-l-heptene, 2-ethyl-l-octene, cis-3-methyl-2- pentene, cis-3-methyl-2-hexene, cis-3-methyl-2-heptene, cis-3-methyl-2-octene, cis- 3-methyl-2-nonene, trans-3-methyl-2-pentene, trans-3-methyl-2-hexene, trans-3- methyl-2-heptene, trans-3-methyl-2-octene, trans-3-methyl-2-nonene, cis-2-hexene, cis-2-heptene, cis-2-octene, cis-2-nonene, cis-2-decene, trans-2-hexene, trans-2- heptene, trans-2-octene, trans-2-nonene, trans-2-decene, cis-3-hexene, cis-3-hep- tene, cis-3-octene, cis-3-nonene, cis-3-decene, trans-3-hexene, trans-3-heptene, trans-3-octene, trans-3-nonene, trans-3-decene, comprising the steps a) selecting a fragrance composition or cosmetic or pharmaceutical preparation, of which the degradation shall be reduced or prevented, b) providing the fragrance composition or cosmetic or pharmaceutical preparation selected in step a),c) providing Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof, d) mixing the fragrance composition or cosmetic or pharmaceutical preparation provided in step b) and the Dihydroavenanthramide D and / or pharmaceutically or cosmetically acceptable salt and / or solvate thereof provided in step c).
10. Method according to claim 9, wherein the fragrance composition or cosmetic or pharmaceutical preparation comprises one, two, three or more or all fragrance(s) selected from the group consisting of 2,4-Dimethylcyclohex-3-ene-1-carbaldehyde, Ethyl acetoacetate, (Z)-Hex-3-en-1-yl methyl carbonate, Linalool, Linalyl acetate, Cyclohexanol, 2-(1 ,1-dimethylethyl)-acetate, Methyl-2-octinoat, (2E)-3,7-Dime- thylocta-2,6-dienal, 3,7-dimethyloct-6-en-1-ol, 2,6,10-Trimethylundec-9-enal, 3-(o- Ethylphenyl)-2,2-dimethylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-dime- thylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, (Eth- oxymethoxy)cyclododecane, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcyclo- pent-3-en-1-yl) but-2-en-1-ol, 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]fu- ran", Gamma-Undecalactone, cis-3-Hexenyl salicylate, Pentadecan-15-olide, (5E)-3-Methyl-5-cyclopentadecen-1 -one, 3-Methyl-5-cyclopentadecen-1 -one, (4E)-3-Me- thyl-4-cyclopentadecen-1-one, 1 ,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cy- clopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, Oxacycloheptadec-10-en-2- one, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin, ethylene brassylate, and trans-2,cis-6-Nonadienal, preferably selected from the group consisting of 2,4-Dimethylcyclohex-3-ene-1- carbaldehyde, Linalool, Linalyl acetate, (2E)-3,7-Dimethylocta-2,6-dienal, 3,7-dime- thyloct-6-en-1-ol, 2,6,10-Trimethylundec-9-enal, 3-(o-Ethylphenyl)-2,2-dime- thylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-dimethylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcyclopent-3-en-1-yl) but-2-en-1-ol, 1 ,3,4,6,7,8-Hexahydro- 4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, 3- (1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin.11 . Fragrance composition comprising a) one or more fragrance(s) selected from the group consisting of aldehydes, alcohols, esters, ketones or ethers, andb) Dihydroavenanthramide D and / or a pharmaceutically or cosmetically acceptable salt and / or solvate thereof, wherein the peroxide value of the fragrance composition is at least 0.25 mmol / L, preferably at least 0.5 mmol / L, based on the total volume of the fragrance composition, and wherein the peroxide value of the fragrance composition is at most 70 %, preferably at most 65 %, further preferably at most 60 %, particularly preferably at most 55 % of the peroxide value of the same composition without component b).
12. Fragrance composition according to claim 11 , wherein the, one, two, three or more or all fragrance(s) of component a) is / are selected from the group consisting of 2,4-Dimethylcyclohex-3-ene-1-carbalde- hyde, Ethyl acetoacetate, (Z)-Hex-3-en-1-yl methyl carbonate, Linalool, Linalyl acetate, Cyclohexanol, 2-(1 ,1-dimethylethyl)-acetate, Methyl-2-octinoat, (2E)-3,7-Dime- thylocta-2,6-dienal, 3,7-dimethyloct-6-en-1-ol, 2,6,10-Trimethylundec-9-enal, 3-(o- Ethylphenyl)-2,2-dimethylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-dime- thylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, (Eth- oxymethoxy)cyclododecane, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcyclo- pent-3-en-1-yl) but-2-en-1-ol, 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]fu- ran, Gamma-Undecalactone, cis-3-Hexenyl salicylate, Pentadecan-15-olide, (5E)-3- Methyl-5-cyclopentadecen-1-one, 3-Methyl-5-cyclopentadecen-1-one, (4E)-3-Me- thyl-4-cyclopentadecen-1-one, 1 ,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cy- clopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, Oxacycloheptadec-10-en-2- one, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin, ethylene brassylate, and trans-2,cis-6-Nonadienal, benzyl acetate, phenoxyethyl isobutyrate, p-tert.butyl cyclohexylacetate, linalyl acetate, dimethyl benzyl carbinyl acetate, phenyl ethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl phenyl glycinate, allyl cyclohexyl propionate, styrallyl propionate, benzyl salicylate, benzyl ethyl ether, linear alkanals containing 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetal- dehyde, cyclamen aldehyde, hydroxy-citronellal, lilial and bourgeonal, ionones, isomethylionone and methyl cedryl ketone, anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, terpenes, balsams, sage oil, camomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, limeblossom oil, juniperberry oil, vetiver oil, olibanum oil, galbanum oil, ladanum oil and lavandin oil, bergamot oil, dihydromyrcenol, lilial, lyral, phenylethyl alcohol, hexylcinnamaldehyde, benzyl acetone, Boisambrene Forte, Ambroxan, indole, hedione, sandelice, citrus oil, mandarin oil, orange oil, allylamyl glycolate, cyclovertal, lavandin oil, clary sage oil, damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Su- per, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, rose oxide, romillat, irotyl, floramate, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, and methyl-, ethyl-esters thereof, l-hex- ene-3-one, l-heptene-3-one, 1-octen-3-one, l-nonene-3-one, l-decene-3-one, octalactone, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 2-ethyl-l-butene, 2- ethyl-l-pentene, 2-ethyl-l-hexene, 2-ethyl-l-heptene, 2-ethyl-l-octene, cis-3-methyl-2- pentene, cis-3-methyl-2-hexene, cis-3-methyl-2-heptene, cis-3-methyl-2-octene, cis- 3-methyl-2-nonene, trans-3-methyl-2-pentene, trans-3-methyl-2-hexene, trans-3- methyl-2-heptene, trans-3-methyl-2-octene, trans-3-methyl-2-nonene, cis-2-hexene, cis-2-heptene, cis-2-octene, cis-2-nonene, cis-2-decene, trans-2-hexene, trans-2- heptene, trans-2-octene, trans-2-nonene, trans-2-decene, cis-3-hexene, cis-3-hep- tene, cis-3-octene, cis-3-nonene, cis-3-decene, trans-3-hexene, trans-3-heptene, trans-3-octene, trans-3-nonene, trans-3-decene.
13. Fragrance composition according to claim 1 1 or 12, wherein the, one, two, three or more or all fragrance(s) of component a) is / are selected from the group consisting of 2,4-Dimethylcyclohex-3-ene-1-carbalde- hyde, Ethyl acetoacetate, (Z)-Hex-3-en-1-yl methyl carbonate, Linalool, Linalyl acetate, Cyclohexanol, 2-(1 ,1-dimethylethyl)-acetate, Methyl-2-octinoat, (2E)-3,7-Dime- thylocta-2,6-dienal, 3,7-dimethyloct-6-en-1-ol, 2,6,10-Trimethylundec-9-enal, 3-(o- Ethylphenyl)-2,2-dimethylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-dime- thylpropion-aldehyde, Hydroxycitronellal, Cyclamen aldehyde, Anise aldehyde, (Eth- oxymethoxy)cyclododecane, Iso E Gamma, (2E)-2-Ethyl-4-(2,2,3)-trimethylcyclo- pent-3-en-1-yl) but-2-en-1-ol, 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]fu- ran", Gamma-Undecalactone, cis-3-Hexenyl salicylate, Pentadecan-15-olide, (5E)- 3-Methyl-5-cyclopentadecen-1 -one, 3-Methyl-5-cyclopentadecen-1 -one, (4E)-3-Me- thyl-4-cyclopentadecen-1-one, 1 ,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cy- clopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, Oxacycloheptadec-10-en-2- one, 3-(1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin, ethylene brassylate, and trans-2,cis-6-Nonadienal,preferably selected from the group consisting of 2,4-Dimethylcyclohex-3-ene-1- carbaldehyde, Linalool, Linalyl acetate, (2E)-3,7-Dimethylocta-2,6-dienal, 3,7-dime- thyloct-6-en-1-ol, 2,6,10-Trimethylundec-9-enal, 3-(o-Ethylphenyl)-2,2-dime- thylpropionalde-hydeand3-(p-Ethylphenyl)-2,2-dimethylpropion-aldehyde, Hy- droxycitronellal, Cyclamen aldehyde, Anise aldehyde, Iso E Gamma, (2E)-2-Ethyl- 4-(2,2,3)-trimethylcyclopent-3-en-1-yl) but-2-en-1-ol, 1 ,3,4,6,7,8-Hexahydro- 4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, a-Hexyl cinnamaldehyde, 3- (1 ,3-Benzodioxol-5-yl)-2-methylpropanal, Ethylvanillin, Vanillin.
14. Cosmetic or pharmaceutical preparation comprising a fragrance composition according to any one of claims 11 to 13.
Citation Information
Patent Citations
Anthranilic acid amides and derivatives thereof as cosmetic and pharmaceutical agents
US20060089413A1
Mixtures comprising anthranilic acid amides and cooling agents as cosmetic and pharmaceutical compositions for alleviating itching
WO2006134013A1
Odor and colorant stabilized compositions
WO2024027931A1
Odor and colorant stabilized compositions
WO2024028513A1