ALDEHYDE MIXTURES FOR FLAVOUR IMPROVEMENT

Abstract

The present invention relates to ingredients for improving the flavour of food products. It concerns flavouring compositions with 8Z, 11Z-heptadecadional, 8Z-heptadecenal and 7Z-hexadecenal and optionally further aldehydes. Furthermore, the present invention relates to preparations with improved taste characteristics comprising an inventive flavouring composition as well as the use of an inventive flavouring composition and a method for improving at least one taste characteristic in a preparation.

Claims

1-14. (canceled)

15. A flavoring composition comprising a combination of aldehydes, wherein the combination of aldehydes comprises: 8Z, 11Z-heptadecadienal; 8Z-heptadecenal; 7Z-Hexadecenal; and optionally, one or more compounds selected from 5Z, 8Z, 12Z-heptadecatrienal, 8Z-pentadecenal, 7Z-tetradecenal, or combinations thereof.

16. The flavoring composition of claim 15 comprising 0.0001 to 30 wt. % of 8Z, 11Z-heptadecadienal; 0.0001 to 30 wt. % or 8Z-heptadecenal; 0.0001 to 30 wt.-% of 7Z-hexadecenal; if present, 0.0001 to 20 wt. % of 5Z, 8Z, 12Z-heptadecatrienal; if present, 0.0001 to 20 wt. % of 8Z-pentadecenal; and/or if present, 0.0001 to 20 wt. % of 7Z-tetradecenal; in each case based on the total weight of the flavoring composition.

17. The flavoring composition of claim 15, wherein one or more of the aldehydes are obtained by enzymatic conversion of palmitoleic acid, arachidonic acid, alpha-linolenic acid, oleic acid, punicic acid, alpha-elaeosteraric acid, docosahexaenoic acid, eicosapentaenoic acid, petroselic acid, chaulmoogric acid, alpha-licaric acid, olive oil, canola oil, macadamia nut oil, sea buckthorn fruit oil, tung oil, fish oil, borage oil, chaulmoogr oil, parsley oil, oiticica oil, pomegranate seed oil, coconut oil, sunflower oil, grape seed oil, and fungal oils obtained from any of the genera selected from Conidiobolus, Flammulina, Fomes, Ganoderma, Mortierella, Panellus, Pleurotus, Psathyrella, Stereum, Umbelopsis.

18. The flavoring composition of claim 15, wherein the flavoring composition further comprises one or more additional flavorings selected from aliphatic flavoring substances, aliphatic aldehydes, mono- or multi-unsaturated aliphatic aldehydes, aliphatic ketones, unsaturated ketones, aliphatic diketones and aliphatic diketoles, aliphatic acids, branched-chain saturated acids, aliphatic esters, unsaturated esters, aliphatic sulfur compounds, aliphatic nitrogen compounds, alicyclic compounds, alicyclic esters, terpene alcohols, terpene ketones, terpene esters, terpene hydrocarbons, aromatic compounds, aromatic aldehydes, aromatic acids, aromatic esters, aromatic sulphur compounds, aromatic ethers, aromatic oxides, aromatic lactones, heterocyclic compounds, heterocyclic furanes, heterocyclic pyrans, heterocyclic pyrroles, heterocyclic pyrazines, heterocyclic thiazoles, or mixtures thereof.

19. The flavoring composition of claim 15, further comprising one or more essential oils, concretes, absolutes, extracts, tinctures, or mixtures thereof.

20. The flavoring composition of claim 15, further comprising one or more juice concentrates.

21. The flavoring composition of claim 15, further comprising one or more flavorings selected from acetophenone, allyl caproate, alpha-ionone, beta-ionone, anisaldehyde, anisyl acetate, anisyl formate, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, beta-ionone, butyl butyrate, butyl caproate, butylidene phthalide, carvone, camphene, caryophyllene, cineol, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascone, decalactone, dihydrocoumarin, dimethyl anthranilate, dodecalactone, ethoxyethyl acetate, ethylbutyric acid, ethyl butyrate, ethyl caprate, ethyl caproate, ethyl crotonate, ethylfuraneol, ethylguaiacol, ethylisobutyrate, ethylisovalerate, ethyl lactate, ethylmethyl butyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptylate, 4-(p-hydroxyphenyl)-2-butanone, gamma-decalactone, geraniol, geranyl acetate, geranyl acetate, grapefruit aldehyde, methyl dihydrojasmonate, heliotropin, 2-heptanone, 3-heptanone, 4-heptanone, 2E-heptenal, 4Z-heptenal, 2E-hexenal, 3Z-hexenol, 2E-hexenoic acid, 3E-hexenoic acid, 2Z-hexenyl acetate, 3Z-hexenyl acetate, 3Z-hexenyl caproate, 2E-hexenyl caproate, 3Z-hexenyl formate, 2Z-hexyl acetate, 3Z-hexyl acetate, 2E-hexyl acetate, 3Z-hexyl formate, para-hydroxybenzyl acetone, isoamyl alcohol, isoamyl isovalerate, isobutyl butyrate, isobutyraldehyde, isoeugenol methyl ether, isopropyl methylthiazole, lauric acid, levulinic acid, linalool, linalool oxide, linalyl acetate, menthol, menthofuran, methyl anthranilate, methylbutanol, methylbutyric acid, 2-methylbutyl acetate, methyl caproate, methyl cinnamate, 5-methylfurfural, 3,2,2-methylcyclopentenolone, 6,5,2-methylheptenone, methyl dihydrojasmonate, methyl jasmonate, 2-methylmethyl butyrate, 2-methyl-2-pentenol acid, methylthiobutyrate, 3,1-methylthiohexanol, 3-methylthiohexyl acetate, nerol, nerol acetate, 2E, 4E-nonadienal, 2,4-nonadienol, 2,6-nonadienol, 2,4-nonadienol, nootkatone, delta-octalactone, gamma-octalactone, 2-octanol, 3-octanol, 1,3-octenol, 1-octyl acetate, 3-octyl acetate, palmitic acid, paraldehyde, phellandrene, pentanedione, phenylethyl acetate, phenylethyl alcohol, phenylethyl isovalerate, piperonal, propionaldehyde, propyl butyrate, pulegone, pulegol, sinensal, sulfurol, terpinene, terpineol, terpinolene, 8,3-s thiomenthanone, 4,4,2-thiomethylpentanone, thymol, delta-undecalactone, gamma-undecalactone, valencene, valeric acid, vanillin, acetoin, ethylvanillin, ethylvanillin isobutyrate (=3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3 (2H)-furanone and derivatives thereof, maltol and maltol derivatives, coumarin and coumarin derivatives, gamma-lactones, delta-lactones, methyl sorbate, divanillin, 4-hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3 (2H) furanone, 2-hydroxy-3-methyl-2-cyclopentenone, 3-hydroxy-4,5-dimethyl-2 (5H)-furanone, acetic acid isoamyl ester, butyric acid ethyl ester, butyric acid-n-butyl ester, butyric acid isoamyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, n-hexanoic acid-n-butyl ester, n-octanoic acid ethyl ester, ethyl-3-methyl-3-phenylglycidate, ethyl-2-E-4-Z-decadienoate, 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al and phenylacetaldehyde, 2-methyl-3-(methylthio) furan, 2-methyl-3-furanthiol, bis(2-methyl-3-furyl)disulphide, furfurylmercaptan, methional, 2-acetyl-2-thiazoline, 3-mercapto-2-pentanone, 2,5-dimethyl-3-furanthiol, 2,4,5-trimethylthiazole, 2-acetylthiazole, 2,4-dimethyl-5-ethylthiazole, 2-acetyl-1-pyrroline, 2-methyl-3-ethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, 2,3-diethyl-5-methylpyrazine, 3-isopropyl-2-methoxypyrazine, 3-isobutyl-2-methoxypyrazine, 2-acetylpyrazine, 2-pentylpyridine, (E,E)-2,4-decadienal, (E,E)-2,4-nonadienal, (E)-2-octenal, (E)-2-nonenal, 2-undecenal, 12-methyltridecanal, 1-penten-3-one, 4-hydroxy-2,5-dimethyl-3 (2H)-furanone, guaiacol, 3-hydroxy-4,5-dimethyl-2 (5H)-furanone, 3-hydroxy-4-methyl-5-ethyl-2 (5H)-furanone, cinnamaldehyde, cinnamon alcohol, methyl salicylate, isopulegol and (here not explicitly stated) stereoisomers, enantiomers, positional isomers, diastereomers, ZIE isomers or epimers thereof.

22. The flavoring composition of claim 15, further comprising one or more compounds conveying a sweet taste.

23. The flavoring composition of claim 15, wherein the one or more compounds conveying a sweet taste are selected from natural sweeteners.

24. The flavoring composition of claim 15, wherein the one or more compounds conveying a sweet taste are selected from synthetic sweeteners.

25. A preparation comprising the flavoring composition of claim 15 in an amount of 0.001 to 10 ppm, based on the total weight of the preparation.

26. The preparation of claim 25, wherein the preparation is a preparation suitable for consumption, a preparation for pleasure, a beverage, a semi-finished product, or an oral hygiene product.

27. The preparation of claim 25, further comprising one or more additional flavorings selected from aliphatic flavoring substances, aliphatic aldehydes, mono- or multi-unsaturated aliphatic aldehydes, aliphatic ketones, unsaturated ketones, aliphatic diketones and aliphatic diketoles, aliphatic acids, branched-chain saturated acids, aliphatic esters, unsaturated esters, aliphatic sulfur compounds, aliphatic nitrogen compounds, alicyclic compounds, alicyclic esters, terpene alcohols, terpene ketones, terpene esters, terpene hydrocarbons, aromatic compounds, aromatic aldehydes, aromatic acids, aromatic esters, aromatic sulphur compounds, aromatic ethers, aromatic oxides, aromatic lactones, heterocyclic compounds, heterocyclic furanes, heterocyclic pyrans, heterocyclic pyrroles, heterocyclic pyrazines, heterocyclic thiazoles, or mixtures thereof.

28. The preparation of claim 25, further comprising one or more essential oils, concretes, absolutes, extract, tinctures, or mixtures thereof.

29. The preparation of claim 25, further comprising one or more juice concentrates.

30. The preparation of claim 25, further comprising one or more flavorings selected from acetophenone, allyl caproate, alpha-ionone, beta-ionone, anisaldehyde, anisyl acetate, anisyl formate, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, beta-ionone, butyl butyrate, butyl caproate, butylidene phthalide, carvone, camphene, caryophyllene, cineol, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascone, decalactone, dihydrocoumarin, dimethyl anthranilate, dodecalactone, ethoxyethyl acetate, ethylbutyric acid, ethyl butyrate, ethyl caprate, ethyl caproate, ethyl crotonate, ethylfuraneol, ethylguaiacol, ethylisobutyrate, ethylisovalerate, ethyl lactate, ethylmethyl butyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptylate, 4-(p-hydroxyphenyl)-2-butanone, gamma-decalactone, geraniol, geranyl acetate, geranyl acetate, grapefruit aldehyde, methyl dihydrojasmonate, heliotropin, 2-heptanone, 3-heptanone, 4-heptanone, 2E-heptenal, 4Z-heptenal, 2E-hexenal, 3Z-hexenol, 2E-hexenoic acid, 3E-hexenoic acid, 2Z-hexenyl acetate, 3Z-hexenyl acetate, 3Z-hexenyl caproate, 2E-hexenyl caproate, 3Z-hexenyl formate, 2Z-hexyl acetate, 3Z-hexyl acetate, 2E-hexyl acetate, 3Z-hexyl formate, para-hydroxybenzyl acetone, isoamyl alcohol, isoamyl isovalerate, isobutyl butyrate, isobutyraldehyde, isoeugenol methyl ether, isopropyl methylthiazole, lauric acid, levulinic acid, linalool, linalool oxide, linalyl acetate, menthol, menthofuran, methyl anthranilate, methylbutanol, methylbutyric acid, 2-methylbutyl acetate, methyl caproate, methyl cinnamate, 5-methylfurfural, 3,2,2-methylcyclopentenolone, 6,5,2-methylheptenone, methyl dihydrojasmonate, methyl jasmonate, 2-methylmethyl butyrate, 2-methyl-2-pentenol acid, methylthiobutyrate, 3,1-methylthiohexanol, 3-methylthiohexyl acetate, nerol, nerol acetate, 2E, 4E-nonadienal, 2,4-nonadienol, 2,6-nonadienol, 2,4-nonadienol, nootkatone, delta-octalactone, gamma-octalactone, 2-octanol, 3-octanol, 1,3-octenol, 1-octyl acetate, 3-octyl acetate, palmitic acid, paraldehyde, phellandrene, pentanedione, phenylethyl acetate, phenylethyl alcohol, phenylethyl isovalerate, piperonal, propionaldehyde, propyl butyrate, pulegone, pulegol, sinensal, sulfurol, terpinene, terpineol, terpinolene, 8,3-s thiomenthanone, 4,4,2-thiomethylpentanone, thymol, delta-undecalactone, gamma-undecalactone, valencene, valeric acid, vanillin, acetoin, ethylvanillin, ethylvanillin isobutyrate (=3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3 (2H)-furanone and derivatives thereof, maltol and maltol derivatives, coumarin and coumarin derivatives, gamma-lactones, delta-lactones, methyl sorbate, divanillin, 4-hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3 (2H) furanone, 2-hydroxy-3-methyl-2-cyclopentenone, 3-hydroxy-4,5-dimethyl-2 (5H)-furanone, acetic acid isoamyl ester, butyric acid ethyl ester, butyric acid-n-butyl ester, butyric acid isoamyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, n-hexanoic acid-n-butyl ester, n-octanoic acid ethyl ester, ethyl-3-methyl-3-phenylglycidate, ethyl-2-E-4-Z-decadienoate, 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al and phenylacetaldehyde, 2-methyl-3-(methylthio) furan, 2-methyl-3-furanthiol, bis(2-methyl-3-furyl)disulphide, furfurylmercaptan, methional, 2-acetyl-2-thiazoline, 3-mercapto-2-pentanone, 2,5-dimethyl-3-furanthiol, 2,4,5-trimethylthiazole, 2-acetylthiazole, 2,4-dimethyl-5-ethylthiazole, 2-acetyl-1-pyrroline, 2-methyl-3-ethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, 2,3-diethyl-5-methylpyrazine, 3-isopropyl-2-methoxypyrazine, 3-isobutyl-2-methoxypyrazine, 2-acetylpyrazine, 2-pentylpyridine, (E,E)-2,4-decadienal, (E,E)-2,4-nonadienal, (E)-2-octenal, (E)-2-nonenal, 2-undecenal, 12-methyltridecanal, 1-penten-3-one, 4-hydroxy-2,5-dimethyl-3 (2H)-furanone, guaiacol, 3-hydroxy-4,5-dimethyl-2 (5H)-furanone, 3-hydroxy-4-methyl-5-ethyl-2 (5H)-furanone, cinnamaldehyde, cinnamon alcohol, methyl salicylate, isopulegol and (here not explicitly stated) stereoisomers, enantiomers, positional isomers, diastereomers, ZIE isomers or epimers thereof.

31. The preparation of claim 25, further comprising one or more compounds conveying a sweet taste selected from natural sweeteners, synthetic sweeteners, or mixtures thereof.

32. A method for improving one or more taste characteristics of a preparation comprising: (a) providing a preparation suitable for consumption, a preparation for pleasure, a beverage, a semi-finished product, or an oral hygiene product; (b) providing the flavoring composition of claim 15; (c) contacting and mixing the preparation with the flavoring composition; and (d) obtaining a preparation with one or more improved taste characteristics.

33. The method of claim 32, wherein the flavoring composition of (b) is in an amount of from 0.001 to 10 ppm, based on the total weight of the preparation.

34. The method of claim 32, wherein at least one of the one or more taste characteristics is richness, body, authenticity, impact, mouthfeel, sweetness, or juiciness.

Description

EXAMPLES

Example 1: Production of a Flavouring Preparation from Natural Sources

1. Borage Seed Oil

[0126] 10 grams of borage seed oil were incubated with Candida antarctica Lipase B and tert-Butanol to hydrolyse the contained triglycerides. The reaction mixture containing free fatty acids from borage seed oil are extracted with methyl-tert-butylether (MTBE) und the solvent is evaporated in a subsequent step. The enriched free fatty acids from borage seed oil are subsequently incubated with an alpha-dioxygenase and an aldehyde dehydrogenase for obtaining the desired aldehydes, which are extracted with ethyl acetate after finishing the enzymatic treatment. 1.8 g of the flavouring preparation according to the invention is obtained after evaporating the solvent and subsequent ball distillation.

2. Macadamia Nut Oil

[0127] 10 grams of macadamia nut oil is incubated with Candida antarctica Lipase B and tert-Butanol to hydrolyse the contained triglycerides. The reaction mixture containing free fatty acids from macadamia nut oil are extracted with MTBE und the solvent is evaporated in a subsequent step. The purified free fatty acids from macadamia nut oil are subsequently incubated with an alpha-dioxygenase and an aldehyde dehydrogenase for obtaining the desired aldehydes, which are extracted with ethyl acetate after finishing the enzymatic treatment. 0.66 g flavouring preparation according to the invention is obtained after evaporating the solvent and subsequent ball distillation.

Example 2: Analytic of the Obtained Flavouring Preparations from Example 1

[0128] The obtained flavouring preparations were analysed via gas chromatography and gas chromatography coupled to a mass spectrometer (GC-MS). Samples were diluted 1:300 using ethyl acetate prior to analysis.

[0129] The following conditions were used: [0130] (1) Gas chromatography: Inj. volume: 1 L; run time: 45 min; column info: 15 m MXT-1 (HT) 0.1 M df; ID: 0.25 mm/60 C.-10 C./min380 C. PTV [0131] (2) Gas chromatography-MS: column info: 20 m ZB-1, 60-9-300, Split 30).

[0132] The following results regarding the aldehydes of the flavouring preparation according to the present invention were obtained for borage seed oil and macadamia nut oil:

1. Borage Seed Oil

TABLE-US-00001 TABLE 1 GC-MS results for a flavouring preparation prepared from borage seed oil. Aldehyde Peak Area [%] Time Tridecanal 0.452 5.833 6Z-,9Z- 0.225 7.983 pentadecadienal Tetradecanal 2.283 12.772 8Z-pentadecenal 0.211 13.740 Pentadecenal 8.685 14.072 Hexadecatrienal 0.458 14.669 7Z-,10Z- 5.615 14.843 hexadecadienal 7Z-hexadecenal 1.548 14.948 Hexadecenal 0.350 15.244 Heptadecatrienal 5.730 15.850 8Z,11Z- 22.395 16.064 heptadecadienal 8Z-heptadecenal 17.528 16.171 Heptadecanal 5.519 16.430 Nonadecenal 2.641 18.259

2. Macadamia Nut Oil

TABLE-US-00002 TABLE 2 GC-MS results for a flavouring preparation prepared from macadamia nut oil. Aldehyde Peak Area [%] Time 12Z-Tridecanal 0.373 11.007 Tridecanal 0.274 11.293 7Z-tetradecenal 1.189 12.335 Tetradecanal 0.430 12.630 8Z-pentadecenal 5.357 13.619 Pentadecenal 2.533 13.906 7Z-hexadecenal 1.683 14.807 8Z-,11Z- 0.446 15.841 heptadecadienal 8Z-heptadecenal 12.611 15.974 Heptadecanal 0.752 16.261 Nonadecenal 0.537 18.108

Example 3: Sensory Evaluation of the Flavouring Preparation

[0133] The obtained and analyzed flavouring compositions were used in different dosing regimens of and tasted by a panel consisting of five to eight educated panellists. The tasting base solution is an aqueous solution with 8 wt.-% sucrose and 0.15 wt.-% citric acid dependent on the total mass of the aqueous solution. The tests were conducted by comparing the taste of the aqueous solution after adding a dosage of an essence oil to a dosage of an essence oil and the respective flavouring composition.

1. Borage Seed Oil

[0134] Table 3 shows the results of the tests with a flavouring preparation obtained from borage seed oil as described in Examples 1 and 2.

TABLE-US-00003 TABLE 3 Results of the sensorial experiments with a flavouring preparation manufactured from borage seed oil. Sample Dosage Odor Taste Essence oil orange 25 ppm fruity, essence, ripe, fruity, essence, ripe, juicy, slightly aldehydic juicy, slightly aldehydic Essence oil orange + 25 ppm plus lift, more impact sweeter, fuller, riper, flavouring composition 0.05 ppm more body Essence oil tangerine 12 ppm fruity, methyl anthranilate, fruity, methyl anthranilate, juicy, slightly aldehydic- juicy, slightly aldehydic- fishy fishy Essence oil tangerine + 12 ppm plus more impact, stronger, more body, impact, flavouring preparation 0.015 ppm more candy-anthranilate, slightly fishy, more typical more fishy, more albedo- peely

[0135] Additionally to testing the flavouring preparation in a model solution, the flavouring composition was also added in dosing regimens of 0.01 to 0.08 g/L of a 0.1 wt.-% solution in triacetin to commercially available citrus lemonades. The overall observed influence on the odor and the taste of the preparations was described by the panelists as that the addition of the flavouring preparation leads to a lift of aldehydic-zesty and albedo-peely notes in the odor. Additionally the odor was fresher and more juicy. The taste is described as having more body and more impact, conveying a sweeter and fuller mouthfeel and being more albedo-aldehydic and fatty-waxy as desired for these types of beverages.

[0136] The beverage application examples are displayed in Table 4.

TABLE-US-00004 TABLE 4 Beverage formulations containing the aldehyde mixture from borage seed oil or macadamia nut oil. Orange Near carbonated Isotonic water soft drink grapefruit mandarine Ingredient [g/L] [g/L] [g/L] Ascorbic acid 0.40 0.40 Citric acid 2.10 1.30 Sweetener mix 0.30 Invert sugar 100.00 35.00 syrup 72.7 wt.-% Fructose syrup 15.00 95 wt.-% Carotine beta 0.01 Orange compound 10.00 Citrus compound 12.00 Mandarine oil 0.10 terpene-free 10 vol.-% in Ethanol Orange Washing 0.60 Naringin ex 0.10 Grapefruit Lemon juice 9.00 concentrate Grapefruit juice 7.00 concentrate Orange juice 7.00 3.00 concentrate Flavouring 0.03-0.08 0.03-0.08 0.01-0.03 preparation from (preferred (preferred (preferred Table 1 0.1 wt.- 0.05) 0.05) 0.05) % in triacetin Carbonated ad 1 L ad 1 L water (6 g/l CO2) Water ad 1 L

[0137] An orange or citrus compound describes a base composition for manufacturing softdrinks comprising an amount of 50 wt-% sugar and 15.5 wt.-% fruit acid and colorants.

[0138] An orange washing is the extraction product from extracting orange essential oil with food grade solvents (e.g. ethanol and water). 5

2. Macadamia Nut Oil

[0139] Table 5 shows the results of the tests with a flavouring composition obtained from macadamia nut oil as described in Examples 1 and 2.

TABLE-US-00005 TABLE 5 Results of the sensorial experiments with a flavouring preparation manufactured from macadamia nut oil. Sample Dosage Odor Taste Essence oil orange 25 ppm fruity, essence, ripe, juicy, fruity, essence, ripe, juicy, slightly aldehydic slightly aldehydic Essence oil orange + 25 ppm + sweeter, fruitier, fuller, sweeter, fuller , riper flavouring composition 0.5 ppm more impact Essence oil tangerine 12 ppm fruity, methyl anthranilate, fruity, methyl anthranilate, juicy, slightly aldehydic- juicy, slightly aldehydic- fishy fishy Essence oil tangerine + 12 ppm + more impact, stronger, mainly juicier flavouring preparation 0.5 ppm juicier, bit more zesty

[0140] Additionally to testing the flavouring preparation in a model solution, the flavouring preparation was also added in dosing regimens of 0.015 to 0.05 ppm to commercially available citrus lemonades. The overall observed influence on the odor and the taste of the preparations was described by the panelists as that the addition of the flavouring preparation leads to a lift and more impact of the odor. Overall, the odor was a bit fresher and more zesty and conveys a bit more fatty-aldehydic, albedo-waxy notes. The taste is described as having more body, being more juicy and fuller with more fatty-aldehydic and albedo-waxy notes as desired for these types of beverages.

Example 4: Formulation Examples and Sensorial Evaluation

[0141] The following tables show flavouring compositions according to the invention, their dosage in the final application and the effect on the taste and odour in the final application.

4.1 Lime Flavouring Composition

TABLE-US-00006 TABLE 6 Ingredients of a lime flavouring composition, its dosage in the final application and the effect on taste and odour in the final application. Ingredient Amount in g/100 g Decanol 0.10 Decanal 0.20 Dodecanal 0.30 Borneol 0.05 Iso-Borneol 0.10 Camphene 0.02 Campheroil 0.10 trans-I-Carveol 0.05 Caryophyllene 2.50 Caryophyllenoxid 0.30 Citral 0.50 p-Cymene 1.00 Eucalyptol 0.50 Fenchol 2.00 Fenchone 0.20 Geranyl acetate 0.05 Linalool 0.50 Nerol 0.06 Neryl acetate 2.50 Ocimene 0.20 gamma-Terpinene 3.00 4-Terpinenol 4.00 alpha-Terpineol 25.00 gamma-Terpineol 4.00 Terpinolene 5.00 Lime oil distilled Q.S. Flavouring preparation from borage 0.01-0.10 (preferably 0.02) seed oil 0.1 wt.-% in triacetin Dosage in final application 25 ppm Effect on taste and odour fresher, more waxy, better mouthfeel

4.2 Mandarine Flavouring Composition

TABLE-US-00007 TABLE 7 Ingredients of a mandarine flavouring preparation, its dosage in the final application and the effect on taste and odour in the final application. Ingredient Amount in g/100 g Decanol 0.01 Octanol 0.05 Octanal 0.10 Nonanal 0.01 Decanal 0.05 trans-I-Carveol 0.01 Caryophyllene 0.10 Citronellal 0.01 Citronellol 0.01 p-Cymene 1.00 4Z-Decenal 0.01 2E-Decenal 0.01 Methyl N-methyl anthranilate 0.20 2E-Dodecenal 0.01 Linalool 0.10 Myrcene 1.80 Nerol 0.01 Perilla aldehyde replacer 0.05 alpha-Pinene 3.00 beta-Pinene 1.50 Sinensal fraction ex orange 0.02 gamma-Terpinene 15.00 4-Terpinenol 0.05 alpha-Terpineol 0.20 Terpinolene 1.00 Thymol 0.10 Orange oil Brazilian 30.00 Flavouring preparation from borage 0.03-0.20 (preferably 0.06) seed oil 0.1 wt.-% in triacetin Dosage in final application 20 ppm Effect on taste and odour more albedo, fatty, more body, more juiciness

4.3 Kalamansi Flavouring Composition

TABLE-US-00008 TABLE 8 Ingredients of a kalamansi flavouring preparation, its dosage in the final application and the effect on taste and odour in the final application. Ingredient Amount in g/100 g Acetaldehyde 0.2 Decanol 0.01 Octanol 0.10 Decanal 0.10 Undecanal 0.03 Dodecanal 0.02 Caryophyllene 0.10 Citral 0.50 Citronellal 0.02 2E,4E-Decadienal 0.02 4Z-Decenal 0.01 Geranyl acetate 0.10 Linalool 0.01 Linalyl acetate 0.10 Mandarine oil Italian 10.00 Nerolidol 0.02 Alpha-pinene 0.60 4-Terpinenol 0.10 alpha-Terpineol 0.20 Orange oil Brazilian 30.00 Tangerine oil Q.S. Flavouring preparation from borage 0.01-0.10 (preferably 0.25) seed oil 0.1 wt.-% in triacetin Dosage in final application 80 ppm Effect on taste and odour more waxy-fatty, albedo, more impact, more body

4.4 Tangerine Flavouring Composition

TABLE-US-00009 TABLE 9 Ingredients of a tangerine flavouring composition, its dosage in the final application and the effect on taste and odour in the final application. Ingredient Amount in g/100 g Dodecanal 0.10 4Z-Decenal 0.02 2E-Decenal 0.02 2E-Dodecenal 0.02 Mandarine oil Italian 5.00 2E,6Z -Nonadienal 1 wt.-% 0.10 6Z-Nonenal 1 wt.-% 0.02 Orange oil bitter 10.00 Sinensal fraction ex orange 0.20 Orange oil Brazilian 20.00 Tangerine oil Q.S. Flavouring preparation from borage 0.01-0.10 (preferably 0.025) seed oil 0.1 wt.-% in triacetin Dosage in final application 80 ppm Effect on taste and odour more waxy-fatty, albedo, more impact, more body

4.5 Orange Flavouring Composition

TABLE-US-00010 TABLE 10 Ingredients of an orange flavouring composition, its dosage in the final application and the effect on taste and odour in the final application. Ingredient Amount in g/100 g Decanol 0.08 Hexanol 0.01 Octanol 0.50 Nonanol 0.10 Hexanal 0.10 Octanal 1.00 Nonanal 0.20 Decanal 1.00 Dodecanal 0.20 Caprylic acid 0.10 trans-I-Carveol 0.25 Caryophyllene 0.04 Caryophyllenoxid 0.10 Citral 0.50 Citronellal 0.15 Citronellol 0.07 2E-Decenal 0.02 Ethyl butyrate 0.20 Ethyl caprylate 0.02 2-Ethyl methylbutyrate 0.02 Geraniol 0.03 2E-Hexenal 0.02 Linalool 3.00 Myrcene 1.80 Nerol 0.05 Nootkatone 0.10 1-Octyl acetate 0.07 Orange essence oil Florida 50.00 Perilla aldehyde replacer 0.15 Sinensal fraction ex orange 0.50 Valencene fraction ex orange 1.00 Orange oil Brazilian Q.S. Flavouring preparation from borage 0.03-0.15 (preferably 0.055) seed oil 0.1 wt.-% in triacetin Dosage in final application 40 ppm Effect on taste and odour sweeter, fuller, aldehydic, more juicy-fruity, riper

4.6 Grapefruit Flavouring Composition

TABLE-US-00011 TABLE 11 Ingredients of a grapefruit flavouring composition, its dosage in the final application and the effect on taste and odour in the final application. Ingredient Amount in g/100 g Decanol 0.02 Octanol 0.20 Octanal 0.50 Nonanal 0.10 Decanal 0.60 Dodecanal 0.05 Capric acid 0.10 Caprylic acid 0.05 trans-I-Carveol 0.04 trans-Carvyl acetate 0.05 Caryophyllene 0.40 Citral 0.20 Citronellal 0.05 p-Cymene 0.20 Geraniol 0.02 Geranyl acetate 0.08 Grapefruit oil white 60.00 Heptyl acetate 0.04 Linalool 0.40 1,8-Menthenthiol 1 wt.-% in limonen 0.70 Myrcene 1.80 Nootkatone 0.40 Ocimene 0.50 1-Octyl acetate 0.10 Palmitic acid 0.08 Perilla aldehyde replacer 0.04 alpha-Pinene 1.00 beta-Pinene 0.25 alpha-Terpineol 0.15 Terpinolene 0.01 Valencene fraction ex orange 0.30 Orange oil Brazilian Q.S. Flavouring preparation from borage 0.01-0.15 seed oil 0.1 wt.-% in triacetin Dosage in final application 25 ppm Effect on taste and odour more albedo-waxy, more impact, sweeter

4.7 Lemon Flavouring Composition

TABLE-US-00012 TABLE 12 Ingredients of a lemon flavouring composition, its dosage in the final application and the effect on taste and odour in the final application. Ingredient Amount in g/100 g Decanol 0.20 Nonanol 0.10 Octanal 0.20 Nonanal 0.80 Decanal 0.40 Undecanal 0.10 Dodecanal 0.05 Borneol 0.04 Campheroil 0.05 Capric acid 0.04 Caryophyllene 0.03 Citral 10.00 Citronellal 0.10 Citronellol 0.04 Citronellyl acetate 0.02 Eucalyptol 0.20 Geraniol 0.05 Geranyl acetate 0.50 Hotrienol 0.02 Linalool 0.20 Linoleicacid 0.10 Nerol 0.10 Neryl acetate 2.00 Palmitic acid 0.10 4-Terpinenol, 0.20 alpha-Terpineol, 0.20 Lime juice oil 20.00 Lemon oil Italian Q.S. Flavouring preparation from borage 0.01-0.10 seed oil Dosage in final application 50 ppm Effect on taste and odour more waxy, residue notes, slightly more juicy