FLAVORING COMPOSITIONS FOR TASTE IMPROVEMENT

Abstract

The present invention relates to flavoring compositions comprising eriocitrin, eriodictyol-7-O-glucoside and eriodictyol for taste improvement. Furthermore, the present invention relates to a method to produce such flavoring compositions as well as their use for taste improvement as well as a method for improving taste characteristics in a preparation.

Claims

1-34. (canceled)

35. Flavoring composition comprising eriocitrin, eriodictyol-7-O-glucoside and eriodictyol, and optionally neoeriocitrin, wherein, eriodictyol is contained in an amount of from 5 wt.-% to 79 wt.-%, preferably in an amount of from 30 to 75 wt.-%, preferably wherein neoeriocitrin, if present, is contained in an amount of from 0.01 wt.-% to 40 wt.-%, preferably in an amount of from 0.1 to 20 wt.-%, preferably in an amount of from 0.25 to 10 wt.-%, preferably wherein eriocitrin is contained in an amount of from 0.01 wt.-% to 40 wt.-%, preferably in an amount of from 0.1 to 20 wt.-%, preferably in an amount of from 0.25 to 10 wt.-%, and preferably wherein eriodictyol-7-O-glucoside is contained in an amount of from 0.2 wt.-% to 60 wt.-%, preferably in an amount of from 1 to 40 wt.-%, each dependent on the dry weight of the flavoring composition.

36. Flavoring composition according to claim 35, wherein the compounds (A) are obtained from a natural source by chemical or enzymatic hydrolysis.

37. Flavoring composition according to claim 36, wherein the compounds (A) are obtained from a natural source from a plant selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora tobiracola, Chrysanthemum morifolium, Chrysanthellum indicum, Citrus species, preferably C. bergamia and C. limon, Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum articulactum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus europaeus, Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica, Impatiens glandulifera.

38. Flavoring composition according to claim 35, wherein the composition comprises at least one additional flavoring substance selected from the group consisting of aliphatic flavoring substances, especially saturated aliphatic alcohols, such as ethanol, isopronanol, butanol, isoamyl alcohol, hexanol, 2-heptanol, octanol (1/2/3), decanol, unsaturated aliphatic alcohols, such as cis-2 pentenol, cis-3 hexenol, trans-2 hexenol, trans-3 hexenol, cis-2 octenol, 1-octen-3-ol, cis-6 nonen-1-ol, trans-2, cis-6 nonadienol, aliphatic aldehydes such as saturated aliphatic aldehydes (e.g. acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, isolvaleraldehyde, homoeriodictyol, hexanal, 3-methyl hexanal, octanal, nonanal, or mono- or multi-unsaturated aliphatic aldehydes, such as 2-methyl but-2-enal, trans-2 hexenal, cis-3 hexenal, cis-4 hexenal, trans-2 octenal, trans-2 nonenal, cis-6 nonenal, trans-2, cis-6 nonadienal, trans 2 decenal, trans-2, trans-decadienal, aliphatic ketones, e.g. saturated ketones (such as 2-butanone, 2-pentanone, 2-heptanone, 2-octanone, 2-methylheptan-3-one, 2-decanone, 2-undecanone), unsaturated ketones (such as 1-penten-3-one, 1-hexen-3-one, 5-methyl-3-hexenone, 3-hepten-2-one, 1-octen-3-one, 2-octen-4-one, 3-octen-2-one, 3-none-2-one), aliphatic diketones and aliphatic diketoles, e.g. diacetyl, acetyl methyl carbinol, 2,3-hexanedione, aliphatic acids, such as straight-chain saturated acids, such as acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, heptanoic acid, octanoic acid, decanoic acid, branched-chain saturated acids, such as 2-methyl heptanoic acid, 4-ethyl octanoic acid, and unsaturated acids, such as 2-butenoic acid, 2-pentenoic acid, 4-pentenoic acid, 2-methyl pentenoic acid, trans-3 hexenoic acid, cis-3 hexenoic acid, 3-octenoic acid, linoleic acid), aliphatic esters, such as saturated esters, e.g. methyl acetate, methylbutyrate, methyl-2-methylbutyrate, methyl hexanoate, ethylacetate, ethylbutyrate, ethyl-2-methylbutyrate, ethyl-3-methylbutyrate, ethyl hexanoate, ethyl decanoate, isopropyl acetate, isobutyl acetate, isobutyl valerate, isoamyl acetate, isoamyl butyrate, isoamyl isovalerate, hexyl acetate, hexyl hexanoate, 3-octyl acetate and unsaturated esters, such as methyl 2-hexenoate, allyl hexanoate, cis-3 hexenyl acetate, cis-3 hexenyl butyrate, aliphatic thiols and dithiols (e.g. propane thiol, allyl mercaptan, 1-methoxy-3-methylbutane-3-thiol, dimethyl sulfide, dimethyl trisulfide, dipropyl sulfide, diallyl trisulfide, other aliphatic sulfur compounds, such as 2-mercapto-3-butanol, methyl thio propanal, 3-mercapto-pentanone, 4-methoxy-2-methyl-2-mercaptobutanone, methyl thiobutyrate, methyl thiobutyrate, methyl 3-methylthiopropionate, aliphatic nitrogen compounds, such as butyl amine, trimethyl amine, allyl isothiocyanate, isopropyl isothiocyanate, alicyclic compounds, such as alicyclic ketones, e.g. cis-jasmone, isophorone, 4-ketoisophorone, alicyclic esters such as methyl jasmonate, hedione, terpenes, e.g. terpene alcohols, such as linalool, citronellol, geraniol, nerol, alpha terpineol, menthol, 8-p-menthene-1,2-diol, fenchol, borneol, nerolidol, hotrienol, terpene aldehydes such as geranial, neral, citronellal, beta-sinensal, terpene ketones, such as alpha-ionone, (D)-carvone, (L)-carvone, nootkatone, piperitone, menthone, alpha damascone, beta damascene, damascenone, terpene esters, such as linalyl acetate, geranyl acetate, citronellyl actetate, carvyl acetate, fenchyl acetate, terpene sulphur compounds, 4-mentha-8-thiol-3-one, thiogeraniol, para-menth-1-ene-8-thiol, mercapto p-menthan-3-one, terpene hydrocarbons, such as D-limonene, L-limonene, alpha-pinene, beta-pinene, ocimene, alpha-terpinene, gamma-terpinene, beta-bisabolene, valencene, terpene oxides, such as 1,8-cineole, rose oxide, mint lactone, menthofuran, aromatic compounds, e.g. aromatic alcohols, such as benzyl alcohol, cinnamyl alcohol, 2-phenyl alcohol, aromatic aldehydes, such as benzaldehyde, cinnamic aldehyde, 5-methyl-2-phenylhexenal, salicylaldehyde, 4-hydroxy benzaldehyde, cyclamen aldehyde, 2-phenyl-2-butenal, aromatic acids, such as 2-phenyl acetic acid, cinnamic acid, aromatic esters such as benzyl acetate, benzyl salicylate, anisyl acetate, methyl phenyl acetate, methyl benzoate, methyl salicylate, methyl cinnamate, aromatic phenols, such as phenol, ortho-cresol, para-cresol, 2,3-dimethyl phenyl, 2-ethyl phenol, 2,3,5-trimethyl phenol, 4-vinyl phenol, guaiacol, 4-vinyl guaiacol, eugenol, thymol, carvacrol, aromatic sulphur compounds, such as thiophenol, diphenyl disulphide, aromatic nitrogen compounds, such as methyl anthranilate, methyl N-methyl anthranilate, aromatic ethers such as vanillin, ethylvanillin, anethol, aromatic oxides, such as heliotropine, diphenyl oxide, aromatic lactones, such as coumarin, dihydro coumarin, heterocyclic compounds, such as heterocyclic lactones, e.g. gamma butyrolactone, gamma-nonalactone, gamma decalactone, delta decalactone, jasmin lactone, delta dodecalactone, ambrettolide, heterocyclic furanes, such as furfuryl alcohol, furfural, 2-acetyl furan, theaspirane, 2-methyl tetrahydro furan-3-one, furfuryl mercaptane, 2-methyl 3-furanthiol, 2-methyl 3-tetrahydro furanthiol, difurfuryl sulfide, difurfuryl disulfide, heterocyclic pyrans, such as maltol, ethyl maltole, rose oxide, maltol isobutyrate, heterocyclic pyrroles such as indole, 2-acetyle pyrrole, pyrrolidine, heterocyclic pyrazines, such as 2-methyl pyrazine, 2,3-dimethyl pyrazine, 2-methyl 3-ethyl pyrazine, trimethyl pyrazine, 2-acetyl pyrazine, 2-methoxy 3-methyl pyrazine, 2-methoxy 3-ethyl pyrazine, 2-methoxy 3-isobutyl pyrazine, 2-ethyl 3-methylthio pyrazine, heterocyclic thiazoles, such as thiazole, 2-methyl thiazole, 4-methyl 5-vinyl thiazole, 2-isobutyl thiazole, 2-acetyl thiazole, flavoring raw materials and flavoring preparations, e.g. essential oils, concretes, absolutes, extract or tinctures from raw materials such as citrus (e.g. lemon, lime, mandarine, bergamotte, grapefruit bitter orange, peel or essence oils), herbs (dill, parsley, cumin, rosemary, sage, clary sage, basil, tarragon, thyme, oregano, savoury, majoram, all spice, mace, nutmeg, clove leave, clove bud, caraway, cinnamom leaves, cinnamom bark, cassia, cardamom, ginger, galangal, turmeric, coriander seed, coriander leaf, fenugreek, juniper berry, wormwood, laurel leaves, eucalyptus, white pepper, green pepper, white pepper, carrot seed, celery seed, lovage leaf, asa foetida, onion, leek, garlic, mustard, horse radish, capsicum, paprika, sea weed, valerian oil, fir needle, spearmint, peppermint, wintergreen, buchu leaf, black currant buds, fennel, star anise, jambu, long pepper, davana, orris, mimosa, cassie, violet leaves, ho leaf, jasmin, ylang ylang, cananga, osmanthus, angelica, clary sage, ambrette seed, hops, camomile, lavender, rose, geranium, citronella, palmarosa, litsea cubeba, lemon grass, tagetes, neroli, petitgrain, mate, cognac oil, coffee, cola nut, cocoa, green tea, black tea, white tea, gentian, tolu balm, benzoe resin, peru balm, cascarilla, galbanum, vetiver, labdanum, patchouli, sandalwood, cedarwood, guaiac wood, oak wood, massoi bark, vanilla pods, tonka bean, as well as enriched fractions thereof, juice concentrates, such as orange juice, lemon juice, strawberry, cherry juice, or passion fruit juice concentrates, waterphases and recoveries from raw materials such as citrus (lemon, lime, orange, mandarine, grapefruit), apple, pear, quince, mispel, red fruits (raspberry, strawberry, blueberry, blackberry, Amellanchia (June plum), rose hip, cranberry, plum, prune, red and black currant, etc.) yellow fruits (peach, apricot, nectarine, banana, etc.), tropical fruits (mango, passionfruit, pineapple, lychee, etc.), vegetables (e.g. cucumber, tomato) and spices (e.g. ginger), 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 (e.g. Hedion?), heliotropin, 2-heptanone, 3-heptanone, 4-heptanone, trans-2-heptenal, cis-4-heptenal, trans-2-hexenal, cis-3-hexenol, trans-2-hexenoic acid, trans-3-hexenoic acid, cis-2-hexenyl acetate, cis-3-hexenyl acetate, cis-3-hexenyl caproate, trans-2-hexenyl caproate, cis-3-hexenyl formate, cis-2-hexyl acetate, cis-3-hexyl acetate, trans-2-hexyl acetate, cis-3-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, trans,trans-2,4-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 (here preferably homofuraneol (=2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone), homofuronol (=2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and maltol derivatives (here preferably ethyl maltol), coumarin and coumarin derivatives, gamma-lactones (here preferably gamma-undecalactone, gamma-nonalactone, gamma-decalactone), delta-lactones (here preferably 4-methyldeltadecalactone, massoilactone, deltadecalactone, tuberolactone), 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-trans-4-cis-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, cis/trans isomers or epimers of these substances.

39. Flavoring composition according to claim 35, wherein the composition comprises at least one sweet-tasting substance selected from the group consisting of natural sweeteners, preferably naturally occurring sweet tasting substances, including plant extracts, such as sweet tasting carbohydrates (such as sucrose, trehalose, lactose, maltose, melizitose, melibiose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, I-rhamnose, D-sorbose, D-mannose, D-tagatose, D-arabinose, I-arabinose, D-ribose, D-glyceraldehyde, D-allulose, maltodextrin), sugar alcohols (such as erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, maltitol, isomaltit, dulcitol, lactitol), proteins (such as miraculin, pentaidin, monellin, thaumatin, curculin, brazzein, mabinlin), D-amino acids (such as D-phenylalanine, D-tryptophan) or extracts or fractions obtained from natural sources containing these amino acids and/or proteins and the physiologically acceptable salts of these amino acids and/or proteins, particularly the sodium, potassium, calcium or ammonium salts thereof; neohesperidindihydrochalkon, naringindihydrochalkon, steviolgylcoside, stevioside, steviolbiosid, rebaudioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, rebaudioside M, rebaudioside N, rebaudioside X, dulcoside, rubusoside, suavioside A, suavioside B, suavioside G, suavioside H, suavioside I, suavioside J, baiyunoside 1, baiyunoside 2, phlomisoside 1, phlomisoside 2, phlomisoside 3, phlomisoside 4, phloretin, phlyydulcin, abrusoside A, abrusoside B, abrusoside C, abrusoside D, cyclocaryoside A, cyclocaryoside I, oslandin, polypodoside A, strogin 1, strogin, 2, strogin 4, selligueanin A, dihydroquercetin-3-acetate, perillartin, telosmosid A15, periandrin I-V, pterocaryoside, cyclocaryoside, mukurozioside, trans-anethol, trans-cinnamaldehyd, bryoside, bryonoside, bryonodulcoside, carnosifloside, hesperetin, scandenoside, gypenoside, hematoxylin, cyanin, chlorogenssure, albiziasaponin, telosmoside, gaudichaudiosid, mogrosides, such as mogroside V, hernandulcine, monatin, glycyrrhetinic acid and its derivatives, particularly glycyrrhizin, preferably glycyrrhizin ammonium salt; extracts or enriched fractions of such extracts such as extracts of Thaumatococcus or Stevia ssp., particularly Stevia rebaudiana, swingle extracts, particularly Momordica or Siratia grosvenorii or Luo-Han-Guo, extracts of Glycyrrhiza ssp., particularly Glycyrrhyzia glabra, extracts of Hydrangea macrophylla ssp., particularly Hydrangea macrophily serrata, extracts of Rubus ssp., particularly Rubus suavissimus, extracts of Lippia dulcis, extracts of Mycetia balansae, preferably comprising balansin A and/or balansin B; synthetic sweeteners, preferably synthetic sweet tasting substances, preferably selected from the group consisting of magap, sodium cyclamate or other physiologically acceptable salts of cyclamic acid, acesulfam K; neohesperidindihydrochalcone, naringindihydrochalcone, hesperetindihydrochalcone, saccharin, saccharin sodium salt, aspartam, superaspartam, neotam, alitam, advantam, perillartin, sucralose, lugduname, carrelame, sucrononate or sucrooctate or mixtures thereof.

40. Use of a flavoring composition according to claim 35 for masking and/or reducing at least one undesired taste characteristic in/of a preparation, preferably wherein the at least one undesired taste characteristic is selected from the group consisting of bitterness, astringency, metallic taste, sour, fermented, pea-like and yeasty, preferably wherein the flavoring composition is used in an amount of 0.05 wt.-%, more preferably in an amount of 0.02 wt.-% and especially preferably in an amount of from 0.001 wt.-% to 0.01 wt.-%, dependent on the total weight of the preparation.

41. Use according to claim 40, wherein the preparation is selected from the group consisting of preparations suitable for consumption, preferably a foodstuff, preparations for pleasure, beverages, semi-finished products and oral hygiene products.

42. Method for masking and/or reducing at least one undesired taste characteristic in/of a preparation, comprising or consisting of the steps a) providing at least one preparation, preferably selected from the group consisting of preparations suitable for consumption, preferably a foodstuff, preparations for pleasure, beverages, semi-finished products and oral hygiene products; b) providing a flavoring composition according to claim 35; c) contacting and mixing the preparation provided in step a) and the flavoring composition provided in step b); d) obtaining a preparation with an improved taste.

43. Method for manufacturing a flavoring composition according to claim 35, comprising or consisting of the steps: (i) providing a natural extract from at least one of the plants selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora tobiracola, Chrysanthemum morifolium, Chrysanthellum indicum, Citrus species preferably C. bergamia and C. limon, Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum articulactum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus europaeus, Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica, Impatiens glandulifera; (ii) providing at least one hydrolase; (iii) mixing the natural extract provided in step (i) with the at least one hydrolase provided in step ii); (iv) incubating the mixture obtained in step iii) at a temperature in the range of from 20 to 60? C., preferably of from 40 to 60? C., optionally under stirring for a duration of from 0.5 to 48 hours, preferably of from 2 to 24 hours, preferably of from 4 to 12 hours; (v) obtaining the flavoring composition; (vi) optionally: purifying the obtained flavoring composition of step (v); and optionally: (vii) adding additional flavoring and/or sweet-tasting substances to the flavoring composition; (viii) obtaining a flavoring composition.

44. Method for manufacturing a flavoring composition according to claim 35, comprising or consisting of the steps: (i) providing a natural extract from at least one of the plants selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora tobiracola, Chrysanthemum morifolium, Chrysanthellum indicum, Citrus species preferably C. bergamia and C. limon, Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum articulactum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus europaeus, Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica, Impatiens glandulifera; (ii) providing at least one natural and non-volatile organic acid, preferably an acid selected from the group consisting of citric acid, tartaric acid, glycolic acid, malic acid, lactic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, fumaric acid, maleic acid and mixtures thereof; (iii) mixing the natural extract provided in step (i) with the at least one natural and non-volatile organic acid provided in step ii); (iv) incubating the mixture obtained in step iii) at a temperature in the range of from 100 to 160? C., preferably of from 110 to 150? C., for a duration of from 4 to 48 hours, preferably of from 8 to 40 hours, preferably of from 12 to 36 hours (v) obtaining a flavoring composition; (vi) optionally: purifying the obtained flavoring composition of step (v); and optionally: (vii) adding additional flavoring and/or sweet-tasting substances to the flavoring composition; (viii) obtaining a flavoring composition.

45. Method according to claim 43, wherein the natural extract provided in step (i) is a citrus extract, preferably selected from C. bergamia and C. limon.

46. Method according to claim 43, wherein the hydrolase provided in step (ii) is a glucosidase or rhamnosidase.

47. Flavoring composition obtained or obtainable by: (i) providing a natural extract from at least one of the plants selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora tobiracola, Chrysanthemum morifolium, Chrysanthellum indicum, Citrus species preferably C. bergamia and C. limon, Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum articulactum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus europaeus, Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica, Impatiens glandulifera; (ii) providing at least one hydrolase; (iii) mixing the natural extract provided in step (i) with the at least one hydrolase provided in step ii); (iv) incubating the mixture obtained in step iii) at a temperature in the range of from 20 to 60? C., preferably of from 40 to 60? C., optionally under stirring for a duration of from 0.5 to 48 hours, preferably of from 2 to 24 hours, preferably of from 4 to 12 hours; (v) obtaining a flavoring composition; (vi) optionally: purifying the obtained flavoring composition of step (v); and optionally: (vii) adding additional flavoring and/or sweet-tasting substances to the flavoring composition; (viii) obtaining a flavoring composition.

48. Use according to claim 40, wherein the used flavoring composition is obtained or obtainable by: (i) providing a natural extract from at least one of the plants selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora tobiracola, Chrysanthemum morifolium, Chrysanthellum indicum, Citrus species preferably C. bergamia and C. limon, Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum articulactum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus europaeus, Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica, Impatiens glandulifera; (ii) providing at least one hydrolase; (iii) mixing the natural extract provided in step (i) with the at least one hydrolase provided in step ii); (iv) incubating the mixture obtained in step iii) at a temperature in the range of from 20 to 60? C., preferably of from 40 to 60? C., optionally under stirring for a duration of from 0.5 to 48 hours, preferably of from 2 to 24 hours, preferably of from 4 to 12 hours; (v) obtaining the flavoring composition; (vi) optionally: purifying the obtained flavoring composition of step (v); and optionally: (vii) adding additional flavoring and/or sweet-tasting substances to the flavoring composition; (viii) obtaining a flavoring composition.

49. Method according to claim 42, wherein the provided flavoring composition is obtained or obtainable by (i) providing a natural extract from at least one of the plants selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora tobiracola, Chrysanthemum morifolium, Chrysanthellum indicum, Citrus species preferably C. bergamia and C. limon, Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum articulactum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus europaeus, Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica, Impatiens glandulifera; (ii) providing at least one hydrolase; (iii) mixing the natural extract provided in step (i) with the at least one hydrolase provided in step ii); (iv) incubating the mixture obtained in step iii) at a temperature in the range of from 20 to 60? C., preferably of from 40 to 60? C., optionally under stirring for a duration of from 0.5 to 48 hours, preferably of from 2 to 24 hours, preferably of from 4 to 12 hours; (v) obtaining the flavoring composition; (vi) optionally: purifying the obtained flavoring composition of step (v); and optionally: (vii) adding additional flavoring and/or sweet-tasting substances to the flavoring composition; (viii) obtaining a flavoring composition.

Description

EXAMPLES

Example 1: Paired Comparison tests

[0113] A trained panel was given different samples with the bitter tasting substances caffeine (500 mg/kg), quinine (10 mg/kg) and naringin (100 mg/kg). Caffeine is the bitter principle of coffee and coffee-type beverages, quinine is used as food additive to flavor tonics or energy drinks and naringin is the bitter principle of grapefruit juice. Each test includes a different amount of bitter-masking substances or mixtures thereof. During the tests, the panellists wear nose-clips to exclude any olfactory impressions. These tests are referred to as bitter-duo tests.

[0114] In a first trial, above mentioned bitter samples were mixed with 10 mg/kg eriodictyol-7-O-glucoside at a purity of >95%. It was observed that the bitter-reducing effect was not significant (p<0.05). The data are shown in Table 1. At a concentration above 50 mg/kg, eriodictyol-7-O-glucoside shows even bitter notes.

TABLE-US-00001 TABLE 1 Bitter-duo test of eriodictyol-7-O-glucoside (>95%) Bitter masking Bitter Number of Dosage activity agent panellists [mg/kg] (%) t-test Caffein 20 10 ?1.94 0.87 Quinine 20 10 ?7.42 0.52 Naringin 20 10 ?2.59 0.81

[0115] In a second test, the bitter agents were mixed with 50 mg/kg eriocitrin at a purity of >95% and the bitter-masking effect evaluated by the panel. It was observed that the bitter masking effect was not significant (p>0.05). The data are shown in Table 2.

TABLE-US-00002 TABLE 2 Bitter-duo test of eriocitrin (>95%) Bitter masking Bitter Number of Dosage activity agent panelists [mg/kg] (%) t-test Caffein 20 10 5.6 0.76 Quinine 20 10 ?1.6 0.92 Naringin 20 10 0.8 0.96

[0116] Another trial was set-up using samples with 10 mg/kg quinine and 50 mg/kg eriodictyol (ED) alone or with an inventive flavoring composition containing eriodictyol-7-O-glucoside (EDMG) and neoeriocitrin (NEC) eriocitrin (EC). A synergistic effect of EDMG, EC and ED was found to improve the bitter masking activity significantly compared to pure eriodictyol. The same effect was observed when using neoeriocitrin instead of eriocitrin. The wt.-% are based on the dry weight of the flavoring composition. The results are displayed in Table 3.

TABLE-US-00003 TABLE 3 Bitter-duo test (10 mg/kg quinine) of eriodictyol and lemon peel extracts Bitter masking Number of Dosage activity No. Sample [wt.-%] panellists [mg/kg] [%] t-test 1 ED 19 50 ?31.0 0.037 2 69% ED, 19 50 ?32.4 0.025 1.2% EDMG, 1% EC 3 41% ED, 18 50 ?58.7 0.031 21% EDMG, 1.9% EC 4 55% ED, 20 50 ?50.7 0.003 11.1% EDMG, 1.5% EC

Example 2: Manufacturing of a Flavoring Composition from Lemon Peel Extract

[0117] A lemon peel extract (300 g) and tartaric acid (39 g) are solved in water/acetone (2700 g). The mixture is filled in an autoclave. The hydrolysis starts after the temperature of 120? C. and a pressure of 5 bar is reached. The reaction ends after 35 hours. After the obtained black liquid has cooled, it was removed from the autoclave. By adding water, the target compounds are precipitated. The solid phase is separated by filtration. Overall, 126 g product in the solid phase, are obtained comprising eriodictyol (56.10 g), eriodictyol 7-O-glycoside (33.06 g) and eriocitrin (0,68 g) after drying.

[0118] Purification of the precipitated extract is done by separation of the target compounds by ad-/desorption on a solid phase. In this particular example, the precipitated extract is cleaned by adsorption on activated carbon material and recovery of target compounds by elution with different solvents: The column with activated carbon (surface: 1400 m.sup.2/g; bed volume: 370 kg/m particle size: 7-75 ?m; particle size d.sub.50=30 ?m) is conditioned with 7.5 fold water/acetone of bed volume. The precipitated extract is rinsed through the conditioned column. The first pass of product solution with a bed volume ratio of 3.5 to 1 was withdrawn. This first pass is referred to as first fraction. The target compounds are adsorbed on the stationary phase. Then, the components are desorbed step by step with water, methanol, ethanol, propan-2-ol, ethyl acetate and tert.-methylbutyl ether. Elution takes place in a ratio of 4 to 1 of the eluting agent relative to the column volume. The fractions are brownish to slightly yellow to clear colorless. The highest content of eriocitrin and, eriodictyol-7-O-glucoside is eluted in the fractions with water and methanol, preferably in the fractions with methanol. The highest yield of eriodictyol at the lowest coloring is eluted in the methanol fraction. Elution of eriodictyol can be done with ethanol, propan-2-ol and ethyl acetate as well. The methanol fraction contained eriodictyol (58.0 g), eriodictyol-7-O-glucoside (41.7 g) and eriocitrin (0.3 g).

[0119] Other solvents than methanol, mixtures of solvents and different CV ratios can be used in order to achieve the same purification than with methanol as described herein. The column volume ration (CV) is the ratio of column bed volume and volume of solution flowing through column. The product was evaluated by a sensory panel (n=20). The bitter masking activity was assessed according to Example 1 and it was observed, that the lemon peel extract was able to significantly mask the bitterness of the quinine model solution.

Example 3: Manufacturing of a Flavoring Composition from Lemon Peel Extract

[0120] A lemon peel extract (100 g) and citric acid (13 g) are solved in water/acetone (900 g). The mixture is filled in the autoclave. The hydrolysis starts after the temperature of 120? C. and a pressure of 5 bar is reached. The reaction ends after 35 hours. After the obtained black liquid has cooled, it was removed from the autoclave. The target compounds are precipitated by adding water. The solid fraction is separated by filtration. Overall 42 g product are obtained after drying comprising of eriodictyol (18.30 g), eriodictyol-7-O-glucoside (10.89 g) and eriocitrin (0.22 g).

[0121] The crude product (42 g) is solved in methanol (168 g) at room temperature. The solution is stirred and an anti-solvent crystallization is forced by adding water (630 g) and eriodictyol (14.56 g), eriodictyol-7-O-glucoside (6.21 g) and eriocitrin (0.04 g) precipitates. By variation of concentration and temperature, different fractions with different ratios of eriodictyol (18.30 g), eriodictyol 7-O-glucoside (10.89 g) and eriocitrin (0.22 g) can be obtained.

Example 4: Manufacturing of a Flavoring Composition from Lemon Peel Extract

[0122] A lemon peel extract (30 g) and citric acid (16,4 g) are solved in water/acetone (270 g). The mixture is filled in the autoclave. The hydrolysis starts after the temperature of 120? C. and a pressure of 4 bar is reached. The reaction ends after 18 hours. After the obtained black liquid has cooled, it was removed from the autoclave. The secondary components are precipitated by adding water, separation by filtration. The target compounds are precipitated by adding water. The solid fraction is separated by filtration. Overall 11 g product are obtained after drying comprising eriodictyol (7,21 g), eriodictyol-7-O-glucoside (0,40 g) and eriocitrin (0.03 g).

Example 5: Manufacturing of a Flavoring Composition from Lemon Peel Extract by Enzymatic Hydrolysis

[0123] A slightly acidified 20 g/L lemon peel extract solution was hydrolyzed with 25 mL/L Vegazym P-CS (Erbsl?h, Geisenheim), a commercial enzyme preparation exhibiting rhamnosidase and glucosidase activity, in tap water stirring for 24 h at 40? C. The product was extracted three times with 40% of reaction volume ethyl acetate by stirring for 10 min followed by separating the phases via centrifugation for 20 min at 17.000?g. The combined organic phase was washed two times with 40% reaction volume tap water followed by drying under vacuum. The hydrolyzed product obtained after 24 h contained 0.01 wt.-% Eriocitrin 12.8 wt.-% Eriodictyol-7-O-glucoside, 69.5 wt.-% Eriodictyol.

[0124] Purification of the crude extract is done by precipitation. The crude extract is dissolved in ethanol at 40? C. and by adding water the target compounds precipitated. After filtration, the product contained 0.01 wt.-% Eriocitrin 3.90 wt.-% Eriodictyol-7-O-glucoside, 76.24 wt.-% Eriodictyol.

Example 6: Manufacturing of a Flavoring Composition from Lemon Peel Extract by Hydrolysis with Citric Acid and Enzymatic Hydrolysis

[0125] A lemon peel extract (300 g) and tartaric acid (39 g) are solved in water/acetone (2700 g). The mixture is filled in the autoclave. The hydrolysis starts after the temperature of 120? C. and a pressure of 5 bar is reached. The reaction ends after 35 hours. After the obtained black liquid has cooled, it was removed from the autoclave. By adding water, the target compounds are precipitated. The solid material is obtained by filtration and an enzymatic hydrolysis is switched for 24 h at 50? C. with Vegazym P-CS with 50 ml/L. The target compounds are recovered by extraction with ethylacetate and concentration. The extract contained 0.01 wt.-% Eriocitrin 3.4 wt.-% Eriodictyol-7-O-glucoside, 72.6 wt.-% Eriodictyol.

Example 7: Taste Improvement of a Vegan Patty

[0126] A vegan patty has been produced containing the following ingredients: water, leguminose protein isolate, sun flower oil, leguminose protein concentrate, coconut oil, methylcellulose, fiber, salt, starch, lactic acid and sodium diacetate. Water, thickener and starch are mixed with water, pH is adjusted, proteins are added next followed by fibre and oil ingredients. Finally, a taste masking ingredient according to Table 4 is added. The ingredients are thoroughly mixed and the dough is formed to patties. The patties where baked in an oven at 200? C. After cooling the patties, patties were sliced and samples were coded for a blind tasting with a panel.

TABLE-US-00004 TABLE 4 Sensory profile of vegan patties with an inventive composition (No. 4) in comparison to pure bitter masking compounds Dosage No. Bitter masking agent [mg/kg] Sensory profile 1 None None bitter, astringent aftertaste, bread- like, roasty 2 Eriodyctiol 98% purity 0.005 roasty, bread-like, bitter, dry 3 Homoeriodictyol 70% 0.10 bitterness less purity intense, roasty, juicy 4 41 wt.-% ED, 21 wt.-% 0.005 less bitter, best EDMG, 1.9 wt.-% EC off-taste masking, juicy

[0127] The vegan patties tasted bitter, astringent with bread-like, roasty notes (Table 4, no.1). The addition of bitter masking compounds eriodictyol and homoeriodictyol as described in EP 1258200 A1 improved the taste profile, whereas homoeriodictyol reduced the bitterness more than eriodictyol. However, the taste improving and bitter masking property of the inventive flavoring composition from lemon peel extract showed the best performance.

Example 8: Flavoring Compositions

[0128] The said mixture can be compared with further taste modulating compounds to impart taste modulating sensory effects. Naringenin and hesperetin have been used as an example and the results are displayed in Table 5. A masking mixture comprising three parts hesperetin, two parts naringenin and two parts of the inventive citrus hydrolysate (55 wt.-% ED, 11.1 wt.-% EDMG, 1.5 wt.-% EC) was tested with 50 mg/kg dosage against naringenin, hesperetin and homoeriodictyol (No. 1-3, Table 5). The compounds and the mixture were all solved in water with added 500 mg/kg caffeine as bitter agent. The panelists were asked to rate the bitter intensity of each sample of one sample pair on a scale of 1-100. The results show that the masking mixture is significantly (t-test=0.0039) masking the bitterness of caffeine solution (No. 4, Table 5) The bitter masking activity is higher than of homoeriodictyol (in direct comparison test no. 3, Table 5, -6,1% reduction), even higher than of hesperetin (in direct comparison test no. 2, Table 5, -16,4% reduction) and highest in direct comparison to naringenin (test no. 1, Table 5, -21,7% reduction). This demonstrates that naringenin and hesperetin alone are not potent bitter masking compounds, but formulated together with the inventive citrus hydrolysate they develop significant bitter masking activity and that the bitter masking activity is then at least as high than of homoeriodictyol although the masking mixture contains only approx. 5 mg/kg eriodictyol. Said mixtures can be obtained by mixing the inventive citrus hydrolysate with hydrolysates from orange (yielding hesperetin), grapefruit or bergamot (yielding naringenin) or bitter orange and lime among other citrus fruits.

TABLE-US-00005 TABLE 5 Bitter masking activity of the inventive composition in comparison to taste modulating compounds naringenin, hesperetin and homoeriodictyol. Dosage of Bitter inventive intensity composi- Bitter Masking [0-100] tion intensity effect No. Taste modulator of base [mg/kg] [0-100] [%] 1 Naringenin 36.4 50 28.5 ?21.7 (50 mg/kg) 2 Hesperetin 39 50 32.6 ?16.4 (50 mg/kg) 3 Homoeriodictyol 37.5 50 35.2 ?6.1 (50 mg/kg) 4 Inventive 38.5 50 27.5 ?28.6 composition

Example 9: Taste Improvement of Protein Food

[0129] A protein enriched food was produced by adding 100 g hot water to 0.5 g Agar Agar (CERO Agar Agar Gelidium Type 8952), stirring with 750 rpm at 55? C. and finally adding 10 wt.-% of pea (preparation 1) and soy protein (preparation 2) concentrate. Mixtures were homogenized and finally filled in cups. The sample thickened and formed a homogenous and stable matrix by cooling down to 8? C. for 20 min. Each sample was pairwise tasted against a sample with an inventive composition, namely a lemon peel hydrolysate according to sample no. 4 from Table 3. The samples were coded and tasted by five flavorists. The intensity of sensory attributes was determined on a scale of 0-10.

TABLE-US-00006 TABLE 6 Pairwise comparison of pea protein fortified product with/without addition of lemon peel hydrolysate Preparation 1 + 100 mg/kg Preparation 1 lemon peel hydrolysate Attribute (Pea) (Sample no. 4, Table 3) Green 3 3.5 Potato 3.5 3 Earthy 2 0 Neroli 2.5 0 Green 6 6 Astringent 5 4 Bitter 8 4 Peapod taste 9 6 Umami 0 1.5

TABLE-US-00007 TABLE 7 Pairwise comparison of soy protein fortified product with/without addition of lemon peel hydrolysate Preparation 2 + 100 mg/kg Preparation lemon peel hydrolysate Attribute (Soy) (Sample no. 4, Table 3) Yeasty 9 8 Mouldy 3 4 Bitter 6.5 4 Sour 5 4 Burnt 8 8.5

[0130] The sensory data show that off-tastes like bitter, astringent, sour and peapod taste can be reduced by adding 100 mg/kg lemon peel hydrolysate according to sample no.4 from Table 3.