Flavoring composition for taste improvement

Abstract

The present invention relates to a flavoring composition for improving taste, comprising eriocitrin, eriocitrin-7-O-glucoside and eriocitrin. In addition, the present invention relates to a method for preparing such a flavoring composition and its use for improving taste and a method for improving the taste characteristics in a preparation.

Description

Technical Field

[0001] The present invention relates to a flavoring composition for improving taste, comprising eriocitrin, eriodictyol-7-O-glucoside and eriodictyol. In addition, the present invention relates to a method for preparing such a flavoring composition and its use for improving taste and a method for improving the taste characteristics in a preparation. Background Art

[0002] There is a constant demand for new substances or compositions for improving the taste profile in preparations such as food, beverages or hygiene products. Various substances may be present in foods and beverages which have an unpleasant taste, such as bitter substances, strongly acidic substances and astringent substances, which are desirable and characteristic in moderation on the one hand (e.g. caffeine in tea or coffee, tannins in red wine or green tea, quinine in so-called bitter lemon drinks, saponins or isoflavones or their glycosides in soy milk, hop extracts in beer, fruit acids or edible acids in sweet fruit juices), but which may also greatly reduce the value on the other hand. Often, the unpleasant taste is further aggravated by an unpleasant odor, for example in soy milk, which often has a bitter taste, and the taste often referred to as "beany" is also described as unpleasant.

[0003] Bitter taste is usually caused by specific substances that bind to special bitter receptors on taste cells (found in so-called taste buds on the tongue) and signal to the brain via a neurochemical cascade, causing a defensive reaction and a negative taste impression (see Wolfgang Meyerhof, Reviews of Physiology, Biochemistry and Pharmacology 2005, 154, 37-72).

[0004] Astringency is caused by astringents (such as metal salts or tannins) precipitating proline-rich proteins in saliva. The normally homogeneous saliva, which acts as a "lubricant", contains denatured proteins, which reduces lubricity, leaving a rough or dry feeling in the mouth, which is also considered astringent (Isabelle Lesschaeve, Ann C. Noble, American Journal of Clinical Nutrition 2005, 81, 330S-335S).

[0005] Sour taste is caused by proton acids. For the acidic impression, the so-called titratable proton concentration is more decisive than the pH: for example, a hydrochloric acid solution with the same pH as a malic acid solution is much less sour than malic acid. In general, the offensive sour taste is greatly weakened by combining with sweet flavoring materials (mainly sugar) or even substances with a salty taste (mainly sodium chloride), while the sour taste of bitter or astringent substances is even more unpleasant.

[0006] Some known taste modifiers that alter these taste impressions are eriodictyol and homoeriodictyol. The bitterness masking activity of eriodictyol was first described in European patent application EP1258200A2. In this application, North American eriodictyol is described as the source of eriodictyol. The application does not disclose any information about the manufacture, nor does it disclose information about the natural sources where eriodictyol can be obtained. Furthermore, there is no description of the effects of eriodictyol when used together with other taste modifiers.

[0007] Eriodictyol is a flavanone. As described in European patent application EP2017272A2, flavanones can generally be obtained by organic acid-catalyzed hydrolysis of the corresponding flavanone glycosides. However, the application only discloses the hydrolysis of components with a purity of more than 90%, such as hesperidin and phloridzin, which are easily recovered. However, no information is disclosed about the hydrolysis of low-purity materials and their purification. It is well known that the unwanted side components formed by the hydrolysis of low-purity materials will give the product a phenolic odor. Therefore, the disclosed method does not introduce a method for economically producing eriodictyol using natural source materials.

[0008] US10596185B2 describes a composition made from lemons rich in eriocitrin and eriocitol for use as an antioxidant and anti-inflammatory agent. No information is disclosed about the taste-modifying properties of the composition and the manufacturing process.

[0009] JP2000217560A describes a method for obtaining an extract rich in eriocitrin from citrus fruits by solvent extraction followed by adsorption on a polymer resin. However, the product obtained exhibits an odor similar to that of Chinese herbal medicine. It is well known that polyphenol-containing materials exhibit odor and browning due to processing and storage conditions. The present application discloses neither a method for producing an odor-free lemon extract nor a method for imparting taste-modulating functions.

[0010] EP2223930A1 describes a method for obtaining an extract rich in eriocitrin from citrus fruits by solvent extraction combined with resin adsorption. The inventors of this patent application have solved the odor problem when using polymer resins by using phenolic modified resins, wherein eriocitrin is adsorbed on the surface by physical and chemical means / ion exchange due to the basic amino group and the weakly acidic phenolic group. The odor is reduced by this process. However, the present invention does not disclose a taste-adjusting composition according to the present invention containing a compound more active than eriocitrin.

[0011] EP1783193A1 describes a composition comprising eriodictyol and eriocitrin. However, a (synergistic) effect on bitterness masking is not described.

[0012] US2017 / 0014439A1 describes a composition comprising eriocitrin and neoeriocitrin. However, the composition is directed to the medical purpose of treating inflammation and / or metabolic syndrome. No (synergistic) effect on bitter taste masking is described.

[0013] Mandalari et al. published “Characterization of flavonoids and pectins from Citrus bergamot (Bergamot) peel, major by-products of essential oil extraction”, Journal of Agricultural and Food Chemistry, Vol. 54, No. 1, December 14, 2005, describing eriocitrin and neoeriocitrin in Citrus bergamot peel. However, no (synergistic) effect on bitterness masking was described.

[0014] EP2756765A1 describes the use of eriodictyol and / or homoeriodictyol as bitterness masking agents in food and beverage compositions. However, a synergistic improvement in the bitterness masking of eriodictyol is not described. Summary of the invention

[0015] Therefore, the main task of the present invention is to provide a flavoring composition which is able to improve the taste characteristics, preferably bitterness and astringency, in a preparation and which can be produced commercially in an economical way and which preferably does not exhibit off-taste.

[0016] This task is mainly solved by providing a flavoring composition comprising eriocitrin, eriocitrol-7-O-glucoside and eriocitrol and optionally neoeriocitrin in a first aspect of the present invention, wherein:

[0017] The content of neoeriocitrin (if any) is 0.1 wt.-% to 40 wt.-%, preferably 0.1 wt.-% to 10 wt.-%,

[0018] The content of eriocitrin is 0.1wt.-% to 40wt.-%, preferably 0.1wt.-% to 10wt.-%,

[0019] The content of eriodictyol-7-O-glucoside is 0.2 wt.-% to 60 wt.-%, preferably 1 wt.-% to 40 wt.-%, and

[0020] The eriodictyol is present in an amount of 5 to 79 wt.-%, preferably 10 to 77 wt.-%, preferably 20 to 76 wt.-%, preferably 30 to 75 wt.-%, each based on the dry weight of the flavoring composition.

[0021] All weight percentages above are based on the dry weight of the flavoring composition. This means that water or solvents are excluded when determining the weight percentages. Therefore, preferably, the dry weight is measured by subtracting the water content from the gross weight of the composition, wherein the dry weight should be determined. Preferably, the water content is determined by Karl Fischer titration, loss on drying or halogen moisture analyzer.

[0022] In one embodiment of the present invention, the seasoning composition comprises 0.1 wt.-% to 40 wt.-% of neoeriocitrin, preferably 0.1 wt.-% to 10 wt.-%, 0.1 wt.-% to 40 wt.-%, preferably 0.1 wt.-% to 10 wt.-%, 0.2 wt.-% to 60 wt.-% of eriocitrin-7-O-glucoside, preferably 1 wt.-% to 40 wt.-%, and 5 wt.-% to 90 wt.-% of eriocitrin, preferably 30 wt.-% to 80 wt.-%.

[0023] In another embodiment of the present invention, the flavoring composition comprises neoeriocitrin in an amount of 0.1 wt.-% to 40 wt.-%, preferably in an amount of 0.1 wt.-% to 10 wt.-%, and eriocitrin in an amount of 0.1 wt.-% to 40 wt.-%, preferably in an amount of 0.1 wt.-% to 10 wt.-%.

[0024] In yet another embodiment of the present invention, the flavoring composition comprises eriocitrin in an amount of 0.1 wt.-% to 40 wt.-%, preferably in an amount of 0.1 wt.-% to 10 wt.-%, and eriocitrin-7-O-glucoside in an amount of 0.2 wt.-% to 60 wt.-%, preferably in an amount of 1 wt.-% to 40 wt.-%.

[0025] In one embodiment of the present invention, the flavoring composition comprises eriocitrin in an amount of 0.1 wt.-% to 40 wt.-%, preferably in an amount of 0.1 wt.-% to 10 wt.-%, and eriocitrin in an amount of 5 wt.-% to 90 wt.-%, preferably in an amount of 30 wt.-% to 80 wt.-%.

[0026] In another embodiment of the present invention, the flavoring composition comprises eriocitrin in an amount of 0.1 wt.-% to 40 wt.-%, preferably in an amount of 0.1 wt.-% to 10 wt.-%, and eriocitol-7-O-glucoside in an amount of 0.2 wt.-% to 60 wt.-%, preferably in an amount of 1 wt.-% to 40 wt.-%.

[0027] In another embodiment of the present invention, the flavoring composition comprises eriocitrin in an amount of 0.1 wt.-% to 40 wt.-%, preferably in an amount of 0.1 wt.-% to 10 wt.-%, and eriodictyol in an amount of 5 wt.-% to 90 wt.-%, preferably in an amount of 30 wt.-% to 80 wt.-%.

[0028] In yet another embodiment of the present invention, the flavoring composition comprises eriodictyol-7-O-glucoside in an amount of 0.2 wt.-% to 60 wt.-%, preferably in an amount of 1 wt.-% to 40 wt.-%, and eriodictyol in an amount of 5 wt.-% to 90 wt.-%, preferably in an amount of 30 wt.-% to 80 wt.-%.

[0029] In one embodiment of the present invention, the flavoring composition comprises 0.1 wt.-% to 40 wt.-% of neoeriocitrin, preferably 0.1 wt.-% to 10 wt.-%, 0.1 wt.-% to 40 wt.-% of eriocitrin, preferably 0.1 wt.-% to 10 wt.-%, and 0.2 wt.-% to 60 wt.-% of eriocitrin-7-O-glucoside, preferably 1 wt.-% to 40 wt.-%.

[0030] In a particularly preferred embodiment of the present invention, the flavoring composition comprises eriocitrin in an amount of 0.1 wt.-% to 40 wt.-%, preferably in an amount of 0.1 wt.-% to 10 wt.-%, and eriocitol-7-O-glucoside in an amount of 0.2 wt.-% to 60 wt.-%, preferably in an amount of 1 wt.-% to 40 wt.-%, and eriocitol in an amount of 5 wt.-% to 90 wt.-%, preferably in an amount of 30 wt.-% to 80 wt.-%.

[0031] In another embodiment of the present invention, the flavoring composition comprises eriodictyol in an amount of 0.1 wt.-% to 40 wt.-%, preferably in an amount of 0.1 wt.-% to 10 wt.-%, eriodictyol-7-O-glucoside in an amount of 0.2 wt.-% to 60 wt.-%, preferably in an amount of 1 wt.-% to 40 wt.-%, and eriodictyol in an amount of 5 wt.-% to 90 wt.-%, preferably in an amount of 30 wt.-% to 80 wt.-%.

[0032] Neoeriocitrin (I) is the 7-O-glycoside of the flavanone eriocitrin and the disaccharide neohesperidin (2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside). The term "neo" refers to the glycosyl moiety.

[0033]

[0034] Eriocitrin (II) is a disaccharide derivative from eriocitol, consisting of eriocitol partially substituted by rutinose 6-O-(α-L-rhamnopyranosyl)-β-D-pyranoglucoside at position 7 via a glycosidic bond. In nature, it acts as an antioxidant.

[0035]

[0036] Eriodictyol-7-O-glucoside (III) is a derivative of eriodictyol with a flavonoid moiety which is O-glycosidically linked to the carbohydrate moiety at the C7 position.

[0037]

[0038] Eriodictyol (IV) is a flavanone extracted from Santorini (Eriodictyon californicum) that is substituted with hydroxyl groups at the 5, 7, 3' and 4' positions.

[0039]

[0040] Surprisingly, during the preparation process, the flavoring composition of the present invention is able to (in this combination) synergistically improve certain taste characteristics (preferably masking bitterness, astringency, metallic taste, sourness, fermentation, pea taste and yeast taste) much better than the taste improvement effect of neoeriocitrin, eriocitrin, eriocitrol-7-O-glucoside and eriocitrol individually.

[0041] When there is a discrepancy between the name of the substance and the structural formula, the structural formula shall prevail. Since the structure shown above can occur as stereoisomers in nature, the present invention also includes R and S-enantiomeric forms. In addition, the glucosides can be bound to the flavonoid part as α- or β-glycosidic bonds. Therefore, according to the present invention, these are also described by the compounds and structures listed above.

[0042] One embodiment of the present invention relates to a flavoring composition, wherein compound (A) is obtained from a natural source by chemical or enzymatic hydrolysis.

[0043] For the purposes of the present invention, "natural source" refers to any material that grows in nature and is not produced by any artificial chemical reaction. According to the present invention, "natural source" is preferably understood to be plants.

[0044] Chemical hydrolysis is a process in which chemical bonds are broken by the addition of water molecules. This reaction can be carried out under conditions such as high temperature.

[0045] Enzymatic hydrolysis is a process in which chemical bonds are broken by the addition of water and enzymes. Enzymes capable of carrying out hydrolysis reactions are called hydrolases.

[0046] In another embodiment of the present invention, compound (A) of the flavoring composition is obtained from a natural source of 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 articulatum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus europaeus, Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica and Impatiens glandulifera.

[0047] For the purposes of the present invention, it is particularly preferred that the flavoring composition is obtained from a citrus source, particularly preferably bergamot (Citrus bergamia) and lemon (Citrus limon). Furthermore, it is preferred that the flavoring composition is obtained from a citrus extract by chemical or enzymatic hydrolysis.

[0048] Yet another embodiment of the present invention relates to a flavoring composition, wherein the composition comprises at least one additional flavoring substance selected from the group consisting of:

[0049] Fatty flavoring substances, in particular saturated fatty alcohols, such as ethanol, isopropanol, butanol, isopentanol, hexanol, 2-heptanol, octanol (1 / 2 / 3), decanol; unsaturated fatty 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; fatty aldehydes, such as saturated fatty aldehydes (e.g. acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, isovaleraldehyde, homoeriochoride, hexanal, 3-methylhexanal, octanal, nonanal; or monounsaturated or polyunsaturated fatty aldehydes, such as 2-methylbut-2-enal, trans-2-hexenal, cis-3-hexenal, cis-4-hexenal, trans-2-octenal, trans-2- Nonanal, cis-6-nonenal, trans-2, cis-6-nonadienal, trans-2-decenal, trans-2, trans-decadienal; aliphatic ketones, for example 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-nonen-2-one); aliphatic diketones and aliphatic diketo alcohols, for example diacetyl, acetylmethyl carbinol, 2,3-hexanedione; fatty 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 saturated acids such as 2-methylheptanoic acid, 4-ethyloctanoic acid; and unsaturated acids such as 2-butenoic acid, 2-pentenoic acid, 4-pentenoic acid, 2-methylpentenoic acid, trans-3-hexenoic acid, cis-3-hexenoic acid, 3-octenoic acid, linoleic acid); aliphatic esters such as saturated esters, for example methyl acetate, methyl butyrate, methyl 2-methylbutyrate, methyl caproate, ethyl acetate, ethyl butyrate, ethyl 2-methylbutyrate, ethyl 3-methylbutyrate, ethyl caproate, ethyl caproate, ethyl caproate, isopropyl acetate, isobutyl acetate, isobutyl valerate, isoamyl acetate, isoamyl butyrate, isoamyl isovalerate, hexyl acetate, hexyl caproate, 3-octyl acetate and unsaturated esters such as methyl 2-hexenoate, allyl caproate, cis-3-hexenoic acid esters, cis-3-hexenyl butyrate; aliphatic thiols and dithiols (e.g., propanethiol, 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, methylthiopropionaldehyde, 3-mercapto-pentanone, 4-methoxy-2-methyl-2-mercaptobutanone, methyl thiobutyrate, methyl thiobutyrate, methyl 3-methylthiopropionate; aliphatic nitrogen compounds such as butylamine, trimethylamine, allyl isothiocyanate, isopropyl isothiocyanate; alicyclic compounds such as alicyclic ketones, for example, cis-jasmone, isophorone, 4-oxoisophorone; alicyclic esters such as methyl jasmonate, methyl dihydrojasmonate;Terpenes, for example terpene alcohols such as linalool, citronellol, geraniol, nerol, α-terpineol, menthol, 8-p-menthene-1,2-diol, fenchyl alcohol, borneol, nerolidol, dehydrolinalool; terpene aldehydes such as geranyl aldehyde, neral, citronellal, β-neral; terpene ketones such as α-ionone, (D)-carvone, (L)-carvone, nootkatone, piperitone, menthone, α-damascenone, β-damascenone, damascenone; terpene esters such as linalyl acetate, geranyl acetate, citronellyl acetate, carvyl acetate, fenchyl acetate; terpene sulfur compounds, 4-menth-8-thiol-3-one, thiogeraniol, p-menth-1-ene-8-thiol, thiol-p-menth-3-one; terpene hydrocarbons , such as D-limonene, L-limonene, α-pinene, β-pinene, ocimene, α-terpinene, γ-terpinene, β-bisabolene, valencene; terpene oxides, such as 1,8-cineole, rose oxide, mentholide, menthofuran; aromatic compounds, for example, aromatic alcohols, such as benzyl alcohol, cinnamyl alcohol, 2-phenyl alcohol; aromatic aldehydes, such as benzaldehyde, cinnamaldehyde, 5-methyl-2-phenylhexenal, salicylaldehyde, 4-hydroxybenzaldehyde, cyclamen aldehyde, 2-phenyl-2-butenal; aromatic acids, such as 2-phenylacetic acid, cinnamic acid; aromatic esters, such as benzyl acetate, benzyl salicylate, anisyl acetate, benzyl acetate, methyl benzoate, methyl salicylate, methyl cinnamate; aromatic phenols, such as phenol, o-cresol, p-cresol, 2,3 -dimethylphenyl, 2-ethylphenol, 2,3,5-trimethylphenol, 4-vinylphenol, guaiacol, 4-vinylguaiacol, eugenol, thymol, carvacrol; aromatic sulfur compounds such as thiophenol, diphenyl disulfide; aromatic nitrogen compounds such as methyl anthranilate, methyl N-methyl anthranilate; aromatic ethers such as vanillin, ethyl vanillin, anisol; aromatic oxides such as piperonal, diphenyl ether; aromatic lactones such as coumarin, dihydrocoumarin; heterocyclic compounds such as heterocyclic lactones, for example, γ-butyrolactone, γ-nonalactone, γ-decalactone, δ-decalactone, jasmine lactone, δ-dodecalactone, hibiscus lactone; heterocyclic furans such as furfuryl alcohol, furfural, 2-acetylfuran, tea snail alkane, 2-methyltetrahydrofuran-3-one, furfurylthiol, 2-methyl 3-furanthiol, 2-methyl 3-tetrahydrofuranthiol, difurfuryl sulfide, difurfuryl disulfide; heterocyclic pyrans such as maltol, ethyl maltol, rose oxide, maltol isobutyrate; heterocyclic pyrroles such as indole, 2-acetylpyrrole, pyrrolidine; heterocyclic pyrroles such as 2-methylpyrazine, 2,3-dimethylpyrazine, 2-methyl 3-ethylpyrazine, trimethylpyrazine, 2-acetylpyrazine, 2-methoxy 3-methylpyrazine, 2-methoxy 3-ethylpyrazine, 2-methoxy 3-isobutylpyrazine, 2-ethyl 3-methylthiopyrazine; heterocyclic thiazoles such as thiazole, 2-methylthiazole, 4-methyl 5-vinylthiazole, 2-isobutylthiazole, 2-acetylthiazole,;

[0050] Flavoring raw materials and flavoring preparations, for example, essential oils, extracts, absolutes, extracts or tinctures from raw materials such as citrus (e.g. lemon, lime, mandarin, bergamot, grapefruit, bitter orange, peel or essential oil); herbs (dill, parsley, cumin, rosemary, sage, clary sage, basil, tarragon, thyme, oregano, savory, hyssop, allspice, mace, nutmeg, clove leaves, clove buds, coriander, cinnamon leaves, cinnamon bark, cassia bark, cardamom, ginger, galangal, turmeric, coriander seeds, coriander leaves, fenugreek, juniper berries, wormwood, bay leaves, eucalyptus, white pepper, green pepper, white pepper, carrot seeds, celery, angelica leaves, fumitory, onion, leek, garlic, mustard, horseradish, chili pepper, red pepper, cumin, thyme, cumin ... Chili, seaweed, valerian oil, fir, spearmint, mint, sedge, buchu leaves, black currant buds, fennel, star anise, wax apple, long pepper, davana, sweet calamus root, mimosa, acacia, purple orchid leaves, camphor leaves, jasmine, ylang-ylang, cananga, osmanthus, angelica, clary sage, okra seeds, humulus flowers, chamomile, lavender, rose, geranium, lemongrass, palmarosa oil, mountain pepper, lemongrass, marigold, neroli, orange leaf, mate, conake oil, coffee, kola nut, cocoa, green tea, black tea, white tea, gentian root, tolu balsam oil, benzoin resin, Peru balsam, West Indian bittersweet tree, white rosin, vetiver, labdanum, patchouli, sandalwood, cedar, guaiac wood, oak, horsetail bark (massoi bark), vanilla pods, tonka beans, and their concentrates,

[0051] Concentrated juices, such as orange juice, lemon juice, strawberry juice, cherry juice, or passion fruit juice concentrates, aqueous phases and regrinds from raw materials such as citrus (lemon, lime, orange, mandarin, grapefruit), apple, pear, papaya, loquat, red berries (raspberry, strawberry, blueberry, blackberry, amelanchier, rose hip, cranberry, plum, prune, red currant and black currant), yellow fruits (peach, apricot, nectarine, banana, etc.), tropical fruits (mango, passion fruit, pineapple, lychee, etc.), vegetables (e.g. cucumber, tomato) and spices (e.g. ginger),

[0052] Acetophenone, allyl hexanoate, α-ionone, β-ionone, anisaldehyde, anisyl acetate, anisyl formate, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, β-ionone, butyl butyrate, butyl hexanoate, butenylphthalide, carvone, camphene, caryophyllene, eucalyptol, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascenone, decalactone, dihydrocoumarin, o-methylamino methyl benzoate, lauryl lactone, ethoxyethyl acetate, ethyl butyric acid, ethyl butyrate, ethyl decanoate, ethyl hexanoate, ethyl crotonate, ethyl furanone, ethyl guaiacol, ethyl isobutyrate, ethyl isovalerate, ethyl lactate, ethyl methyl butyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptanoate, 4-(p-hydroxyphenyl)-2-butanone, γ-decanoyl lactone, geraniol, geranyl acetate, geranyl acetate, naringenaldehyde, dihydrojasmonic acid matrix (e.g. ), piperonal, 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 hexanoate, trans-2-hexenyl hexanoate, cis-3-hexenyl formate, cis-2-hexyl acetate, cis-3-hexyl acetate, trans-2-hexyl acetate, cis-3-hexyl formate, p-hydroxybenzyl acetone, isopentanol, isopentanyl isovalerate, isobutyl butyrate, isobutylaldehyde, isoeugenol methyl ether, isopropyl methylthiazole, lauric acid, levulinic acid, linalool, linalool oxide, linalyl acetate, thin Furfuryl alcohol, menthyl furan, methyl o-aminobenzoate, methyl butanol, methyl butyric acid, 2-methyl butyl acetate, methyl caproate, methyl cinnamate, 5-methyl furfural, 3,2,2-methylcyclopentenone, 6,5,2-methylheptanone, methyl dihydrojasmonate, methyl jasmonate, 2-methyl methyl butyrate, 2-methyl-2-pentenoic acid, methyl thiobutyrate, 3,1-methylthiohexanol, 3-methylthiohexyl acetate, nerol, nerol acetate, trans, trans-2,4-nonadienal, 2,4-nonadienol, 2,6-nonadienol, 2,4-nonadienol, nootkatone, δ-octalactone, γ-octalactone, 2-octanol, 3-octanol, 1,3-octenol, 1-acetic acid -octyl ester, 3-octyl acetate, palmitic acid, secondary aldehyde, phellandrene, acetylacetone, phenylethyl acetate, phenylethanol, phenylethyl isovalerate, piperonal, propionaldehyde, propyl butyrate, pulegone, pulegol, sweet orange aldehyde, thiothiazole, terpinene, terpineol, terpinolene, 8,3-thiomenthone, 4,4,2-methylthiopentanone, thymol, δ-undecalactone, γ-undecalactone, valencene, valeric acid, vanillin, acetoin, ethyl vanillin, ethyl vanillyl isobutyrate (= 3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3(2H)-furanone and its derivatives (preferably soy sauce ketone (= 2-ethyl-4-hydroxy-5-methyl- 3 (2H) -furanone), furanones (= 2-ethyl-5-methyl-4-hydroxy-3 (2H) -furanone and 5-ethyl-2-methyl-4-hydroxy-3 (2H) -furanone), maltol and maltol derivatives (preferably ethyl maltol), coumarin and coumarin derivatives, γ-lactones (preferably γ-undecalactone, γ-nonalactone, γ-decanolactone), δ-lactones (preferably 4-methyl δ-decanolactone, dihydropentylpyran, δ-decanolactone, tuberose lactone), 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, isopentyl acetate, ethyl butyrate, n-butyl butyrate, isopentyl butyrate, ethyl 3-methyl butyrate, ethyl hexanoate, allyl hexanoate, n-butyl hexanoate, ethyl octanoate, ethyl 3-methyl-3-phenylglycine, ethyl 2-trans-4-cis-decadienoate, 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-heptane 1-ene-aldehyde and phenylacetaldehyde, 2-methyl-3-(methylthio)furan, 2-methyl-3-furanthiol, di(2-methyl-3-furanyl) disulfide, furfurylthiol, methylthiopropionaldehyde, 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-ethyl 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-methyltridecal aldehydes, 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, cinnamyl alcohol, methyl salicylate, isopulegol and (not explicitly stated here) stereoisomers, enantiomers, positional isomers, diastereomers, cis / trans isomers or epimers of these substances.

[0053] Another embodiment of the present invention relates to a flavoring composition, wherein the composition comprises at least one sweetening substance selected from the group consisting of:

[0054] Natural sweeteners, preferably naturally occurring sweeteners, include plant extracts, such as sweet carbohydrates (such as sucrose, trehalose, lactose, maltose, melezitose, melibiose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, 1-rhamnose, D-sorbose, D-mannose, D-tagatose, D-arabinose, 1-arabinose, D-ribose, D-glyceraldehyde, D-psicose, maltodextrin); sugar alcohols (such as erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, maltitol, isomalt, galactitol, lactitol); sugar alcohols); proteins (such as miraculin, pitatin, monelin, thaumatin, curculin, sweet protein, tangerine); 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 physiologically acceptable salts of these amino acids and / or proteins, in particular their sodium, potassium, calcium or ammonium salts; neohesperidin dihydrochalcone, naringin dihydrochalcone, steviol glycosides, stevioside, steviolbioside, rebaudioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E ... E, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside B, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside E, rebaudioside B, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E Baudioside F, rebaudioside G, rebaudioside H, rebaudioside M, rebaudioside N, rebaudioside X, ducoside, rubusoside, rubusoside A, rubusoside B, rubusoside G, rubusoside H, rubusoside I, rubusoside J, baiyun ginsenoside 1, baiyun ginsenoside 2, succinoside 1, succinoside 2, succinoside 3, succinoside 4, phloretin, phyllodulcin, abrinus triterpenoid glycoside A, abrinus triterpenoid glycoside B, abrinus triterpenoid glycoside C, abrinus triterpenoid glycoside D, cyclacoside A, cyclacoside I, osladin, polyboside A, succinoside 1, succinoside 2, succinoside 4, Pteridin A, dihydroquercetin-3-acetate, perilla, tromos A15, Brazilian glycyrrhizin IV, butterfly card glycoside, cyclocardin, soapberry sesquiterpene glycoside, trans-anethole, trans-cinnamaldehyde, Bryce, Brynos, fleshy snow gall saponin, rattan notoginseng snow gall glycoside, hesperidin, gynostemma pentaphyllum saponin, hematoxylin, anthocyanin, chlorogenic acid, albizzia saponin, tromos, ganchaos, mogrosides such as mogroside V, Helan sweet essence, monatin, glycyrrhetinic acid and derivatives thereof, in particular glycyrrhizin, preferably glycyrrhizin ammonium salt; extracts or concentrated fractions of extracts, such as catanine or steviol glycosides (Stevia ssp.) extracts, in particular stevia, bergamot extracts, in particular monk fruit or Luo-Han-Guo, liquorice extracts, in particular liquorice root extract, Hydrangea macrophylla ssp.) extract, in particular hydrangea serrata, raspberry extract, in particular sweet tea leaf extract, sweet tongue grass extract, Mycetia balansae extract, preferably containing balansin A and / or balansin B;.

[0055] Synthetic sweeteners, preferably synthetic sweeteners, are preferably selected from the group consisting of magnum, sodium cyclamate or other physiologically acceptable salts of cyclamate, acesulfame K; neohesperidin dihydrochalcone, naringin dihydrochalcone, hesperetin dihydrochalcone, saccharin, saccharin sodium salt, aspartame, super aspartame, neotame, alitame, advantame, perilla, sucralose, lugduname, carrelame, suronate or suronate or a mixture thereof.

[0056] In terms of the present invention, it is particularly preferred that the flavoring composition of the present invention comprises at least one additional sweetener selected from the group consisting of psicose, sucrose, trehalose, phloretin, naringenin, hesperetin, rubusoside, steviol glycosides (preferably rebaudioside A, rebaudioside D and rebaudioside M), mogroside V, phyllotoxin and hesperetin dihydrochalcone.

[0057] Another aspect of the present invention relates to the use of a flavoring composition according to the present invention for masking and / or reducing at least one undesirable taste characteristic in a formulation, preferably wherein the flavoring composition is used in an amount of 0.05 wt.-%, more preferably in an amount of 0.02 wt.-%, particularly preferably in an amount of 0.001 wt.-% to 0.01 wt.-%, based on the total weight of the formulation.

[0058] One embodiment of the use according to the invention relates to the use of a flavouring composition according to the invention, wherein the preparation is selected from the group consisting of preparations suitable for consumption, preferably foods, preparations for recreation, beverages, semi-finished products and oral hygiene products.

[0059] Preferably, the at least one undesirable taste characteristic is selected from the group consisting of bitter, astringent, metallic, sour, fermented, pea-like and yeasty.

[0060] Bitterness, astringency and sourness are taste impressions defined above. In preparations with heavy metal content, such as multivitamin preparations containing, for example, copper, zinc and / or magnesium, a metallic taste can be perceived. In addition, some drugs can impart a metallic taste in the mouth. The off-flavor of sweet glycosides such as rebaudioside A is described as a combination of bitterness and metallic taste.

[0061] When consuming fermented foods, a fermented taste can be detected, which indicates microbial transformation of the preparation. This taste is described as somewhat sour and somewhat salty, which is desirable in some preparations, but may also be unacceptable or unwelcome.

[0062] The pea taste impression describes the taste of beans in formulations (e.g. protein-rich food formulations) where this taste is unacceptable.

[0063] Yeasty flavors are found specifically in preparations made with yeast, such as bread, sparkling wine or beer. This yeasty flavor is desirable in some preparations, but undesirable in others or at high yeast concentrations.

[0064] Another aspect of the present invention relates to a method for masking and / or reducing at least one undesirable taste characteristic in / of a formulation, comprising or consisting of the following steps:

[0065] a) providing at least one preparation, preferably selected from the group consisting of preparations suitable for consumption, preferably foods, preparations for recreation, beverages, semi-finished products and oral hygiene products;

[0066] b) providing a flavoring composition according to the invention;

[0067] c) contacting and mixing the formulation provided in step a) and the flavoring composition provided in step b); and

[0068] d) Obtaining a preparation with improved taste.

[0069] In the context of the present invention, it is particularly preferred that the undesirable taste characteristic is selected from the group consisting of bitterness, astringency, metallic taste, sourness, fermentation, pea taste and yeast taste.

[0070] In a preferred embodiment, the flavoring composition is produced or producible by the method for producing a flavoring composition disclosed herein.

[0071] Another aspect of the present invention relates to a method for producing the flavoring composition of the present invention, comprising or consisting of the following steps:

[0072] (i) providing a natural extract from at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora abiracola, Chrysanthemum morifolium, Chrysanthellumindicum, Citrus species (preferably C. bergamia and C. limon), Dracocephalum rupestre, Viscum liquidambaricohum, Viscum coloratum, Viscum articulatum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus rubrum, europaeus, Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica and Impatiens glandulifera;

[0073] (ii) providing at least one hydrolase;

[0074] (iii) mixing the natural extract provided in step (i) with the at least one hydrolase provided in step ii);

[0075] (iv) incubating the mixture obtained in step iii) at a temperature of 20°C to 60°C, preferably 40°C to 60°C, optionally under stirring, for 0.5 to 48 hours, preferably 2 to 24 hours, preferably 4 to 12 hours;

[0076] (v) obtaining a flavoring composition according to the invention;

[0077] (vi) optionally: purifying the flavoring composition obtained in step (v);

[0078] and optionally:

[0079] (vii) adding additional flavouring and / or sweetening substances, preferably as defined herein, to the flavouring composition; and

[0080] (viii) obtaining a flavouring composition according to the invention, preferably comprising an additional flavouring and / or sweetening substance as defined herein.

[0081] Furthermore, the present invention relates to a method for producing a flavoring composition according to the present invention, comprising or consisting of the following steps:

[0082] (i) providing a natural extract from at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora abiracola, Chrysanthemum morifolium, Chrysanthellumindicum, Citrus species (preferably C. bergamia and C. limon), Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum articulatum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus rubrum, europaeus, Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica and Impatiens glandulifera;

[0083] (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;

[0084] (iii) mixing the natural extract provided in step (i) with the at least one natural and non-volatile organic acid provided in step ii);

[0085] (iv) incubating the mixture obtained in step iii) at a temperature of 100° C. to 160° C., preferably 110° C. to 150° C., for 4 to 48 hours, preferably 8 to 40 hours, preferably 12 to 36 hours;

[0086] (v) obtaining a flavoring composition according to the invention;

[0087] (vi) optionally: purifying the flavoring composition obtained in step (v);

[0088] and optionally:

[0089] (vii) adding additional flavouring and / or sweetening substances, preferably as defined herein, to the flavouring composition; and (viii) obtaining a flavouring composition according to the invention, preferably as defined herein.

[0090] Furthermore, the present invention relates to a method for producing a flavoring composition according to the present invention, comprising or consisting of the following steps:

[0091] (i) providing a natural extract from at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora abiracola, Chrysanthemum morifolium, Chrysanthellumindicum, Citrus species (preferably C. bergamia and C. limon), Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum articulatum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus europaeus, Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica and Impatiens glandulifera;

[0092] (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;

[0093] (iii) mixing the natural extract provided in step (i) with the at least one natural and non-volatile organic acid provided in step ii);

[0094] (iv) incubating the mixture obtained in step iii) at a temperature of 100° C. to 160° C., preferably 110° C. to 150° C., for 4 to 48 hours, preferably 8 to 40 hours, preferably 12 to 36 hours;

[0095] (v) obtaining a flavoring composition according to the invention;

[0096] (vi) optionally: purifying the flavoring composition obtained in step (v);

[0097] (vii) providing at least one hydrolase;

[0098] (viii) mixing the composition obtained in step (v) or (vi) with at least one hydrolase provided in step (vii);

[0099] (ix) incubating the mixture obtained in step (viii) at a temperature of 20°C to 60°C, preferably 40°C to 60°C, optionally under stirring, for 0.5 hour to 48 hours, preferably 2 hours to 24 hours, preferably 4 hours to 12 hours;

[0100] (x) obtaining a flavoring composition according to the present invention;

[0101] (xi) optionally: purifying the flavoring composition obtained in step (x);

[0102] and optionally:

[0103] (xii) adding additional flavouring and / or sweetening substances, preferably as defined herein, to the flavouring composition; and

[0104] (xiii) obtaining a flavouring composition according to the invention, preferably comprising an additional flavouring and / or sweetening substance as defined herein.

[0105] In steps (v) and (x) of the above method, a flavoring composition according to the invention is obtained. In both cases, the flavoring composition is manufactured according to the invention. However, in the composition obtained in step (x) of the above method, the content of eriodictyol is further increased.

[0106] Preferably, in the present context and according to the above method, the term "composition according to the invention" refers to the composition obtained in step (v).

[0107] Preferably, in the present context and according to the above method, the term "composition according to the invention" refers to the composition obtained in step (x).

[0108] Preferably, in the present context and according to the above method, the term "composition according to the invention" refers to the composition obtained in step (v) and step (x).

[0109] Preferably, according to the method of the present invention, at least one natural and non-volatile organic acid is provided in step (ii) or (vii), and the incubation in step (iv) is carried out at a pressure in the range of 2 bar to 6.5 bar, preferably in the range of 3 bar to 6 bar, preferably in the range of 3.5 bar to 5.5 bar, preferably in the range of 4 bar to 5 bar.

[0110] In the context of the present invention, it is preferred that the purification in step vi) of the method of the present invention is carried out by at least one method selected from the group consisting of absorption, adsorption, chromatography, crystallization, precipitation, liquid-liquid extraction, solid-liquid extraction, filtration, drying or freeze-drying. It is particularly preferred that the seasoning composition is prepared using a combination of methods selected from the group consisting of absorption, adsorption, chromatography, crystallization, precipitation, liquid-liquid extraction, solid-liquid extraction, filtration, drying or freeze-drying.

[0111] One embodiment of the method for manufacturing a flavoring composition according to the present invention relates to a method, wherein the natural extract provided in step (i) is a citrus extract, preferably selected from the group consisting of C. bergamia and C. limon.

[0112] Another embodiment of the method for producing a flavoring composition according to the present invention relates to a method, wherein the hydrolase provided in step (ii) or (vii) is a glucosidase and / or a rhamnosidase.

[0113] Glucosidase is an enzyme that is able to degrade complex carbohydrates by severing carbohydrate bonds between sugar monomers.

[0114] Rhamnosidase is an enzyme that catalyzes the hydrolysis of terminal non-reducing L-rhamnose.

[0115] Another aspect of the invention relates to a flavouring composition according to the invention, obtained or obtainable by a process for the manufacture of a flavouring composition according to the invention.

[0116] Furthermore, the present invention relates to the use of a flavouring mixture as described herein, wherein the flavouring composition used is obtained or obtainable by a process for the manufacture of a flavouring composition according to the invention.

[0117] Furthermore, the embodiments of the present invention are intended to be illustrative rather than restrictive. DETAILED DESCRIPTION

[0118] Example 1: Paired comparison test

[0119] A trained panel was given different samples containing the bitter substances caffeine (500mg / kg), quinine (10mg / kg) and naringin (100mg / kg). Caffeine is the bitter element in coffee and coffee-like drinks, quinine is used as a food additive in flavor tonics or energy drinks, and naringin is the bitter element in grapefruit juice. Each test included different amounts of the bitter masking substance or its mixture. During the test, the panelists wore a nose clip to exclude any olfactory impression. These tests are called bitter double tests.

[0120] In the first test, the above bitter samples were mixed with 10 mg / kg of eriodictyol-7-O-glucoside with a purity of >95%. No significant bitterness reduction effect was observed (p < 0.05). The data are shown in Table 1. At concentrations above 50 mg / kg, eriodictyol-7-O-glucoside showed an even more bitter taste.

[0121] Table 1: Double test of bitterness of eriodictyol-7-O-glucoside (>95%)

[0122] Bitter Number of team members Dosage [mg / kg] Bitter taste masking activity (%) t-test caffeine 20 10 -1.94 0.87 Quinine 20 10 -7.42 0.52 Naringin 20 10 -2.59 0.81

[0123] In the second test, the bittering agent was mixed with 50 mg / kg of eriocitrin with a purity of >95% and the panel evaluated the bitterness masking effect. It was observed that the bitterness masking effect was not significant (p>0.05). The data are shown in Table 2.

[0124] Table 2: Double test of bitter taste of eriocitrin (>95%)

[0125] Bitter Number of team members Dosage [mg / kg] Bitter taste masking activity (%) t-test caffeine 20 10 5.6 0.76 Quinine 20 10 -1.6 0.92 Naringin 20 10 0.8 0.96

[0126] Another test was conducted using samples containing 10 mg / kg of quinine and 50 mg / kg of eriodictyol (ED) alone or samples of the flavoring composition of the present invention containing eriodictyol-7-O-glucoside (EDMG) and neoeriocitrin (NEC) eriodictyol (EC). It was found that the synergistic effect of EDMG, EC and ED significantly increased the bitter taste masking activity compared to pure eriodictyol. The same effect was observed when neoeriocitrin was used instead of eriodictyol. The wt.-% is based on the dry weight of the flavoring composition. The results are shown in Table 3.

[0127] Table 3: Dual test of bitterness of eriodictyol and lemon peel extract (10 mg / kg quinine)

[0128]

[0129] Example 2: Preparation of flavoring composition from lemon peel extract

[0130] Lemon peel extract (300 g) and tartaric acid (39 g) were dissolved in water / acetone (2700 g). The mixture was placed in an autoclave. Hydrolysis began after reaching a temperature of 120° C. and a pressure of 5 bar. The reaction lasted for 35 hours and ended. After the obtained black liquid had cooled, it was taken out of the autoclave.

[0131] By adding water, the target compound was precipitated. The solid phase was separated by filtration. In general, 126 g of solid phase product was obtained after drying, which contained eriodictyol (56.10 g), eriodictyol-7-O-glycoside (33.06 g) and eriocitrin (0.68 g).

[0132] Purification of the precipitated extract was accomplished by separation of the target compound by solid phase adsorption / desorption. In this specific example, the precipitated extract was cleaned by adsorption on an activated carbon material and recovery of the target compound by elution with different solvents: an activated carbon column (surface: 1400 m 2 / g; bed volume: 370kg / m particle size: 7-75μm; particle size d 50 =30pm) is adjusted with 7.5 times the bed volume of water / acetone. The precipitated extract is washed through the adjustment column. The first product solution with a bed volume ratio of 3.5:1 is taken out. The first is called the first fraction. The target compound is adsorbed on the stationary phase. Then, the components are gradually desorbed with water, methanol, ethanol, propan-2-ol, ethyl acetate and tert-methyl butyl ether. The elution is implemented under the condition that the ratio of the eluent to the column volume is 4:1. The fraction is brown to slightly yellow to colorless and transparent. Among the fractions eluted with water and methanol, it is preferred that the content of eriodictyol and eriodictyol-7-O-glucoside eluted in the component eluted with methanol is the highest. The highest yield of eriodictyol is eluted in the methanol fraction when the color is the lightest. Ethanol, propan-2-ol and ethyl acetate can also be used for eriodictyol elution. The methanol fraction contains eriodictyol (58.0g), eriodictyol-7-O-glucoside (41.7g) and eriodictyol (0.3g).

[0133] Other solvents, mixtures of solvents and different CV ratios besides methanol can be used to achieve the same degree of purification as methanol described herein. The column volume ratio (CV) is the ratio of the column bed volume to the volume of solution flowing through the column. The products were evaluated by a sensory panel (n=20). Bitter taste masking activity was evaluated according to Example 1 and it was observed that the lemon peel extract was able to significantly mask the bitter taste of a quinine model solution.

[0134] Example 3: Preparation of flavoring composition from lemon peel extract

[0135] Lemon peel extract (100g) and citric acid (13g) were dissolved in water / acetone (900g). The mixture was placed in an autoclave. Hydrolysis began after reaching a temperature of 120°C and a pressure of 5bar. The reaction was continued for 35 hours and then ended. After the obtained black liquid was cooled, it was taken out from the autoclave. The target compound was precipitated by adding water. The solid fraction was separated by filtration. A total of 42g of product was obtained after drying, which contained eriodictyol (18.30g), eriodictyol-7-O-glucoside (10.89g) and eriodictyol (0.22g).

[0136] The crude product (42 g) was dissolved in methanol (168 g) at room temperature. The solution was stirred and the antisolvent crystallization was promoted by adding water (630 g) and eriodictyol (14.56 g), eriodictyol-7-O-glucoside (6.21 g) and eriodictyol (0.04 g) precipitation. By changing the concentration and temperature, different proportions of eriodictyol (18.30 g), eriodictyol-7-O-glucoside (10.89 g) and eriodictyol (0.22 g) can be obtained.

[0137] Example 4: Preparation of flavoring composition from lemon peel extract

[0138] Lemon peel extract (30 g) and citric acid (16.4 g) were dissolved in water / acetone (270 g). The mixture was placed in an autoclave. Hydrolysis began after reaching a temperature of 120° C. and a pressure of 4 bar. The reaction was continued for 18 hours and then ended. After the obtained black liquid was cooled, it was taken out from the autoclave. The second component was precipitated by adding water and separated by filtration. The target compound was precipitated by adding water. The solid fraction was separated by filtration. A total of 11 g of product was obtained after drying, which contained eriodictyol (7.21 g), eriodictyol-7-O-glucoside (0.40 g) and eriodictyol (0.03 g).

[0139] Example 5: Lemon Peel Extract pass Enzymatic hydrolysis to produce flavoring compositions

[0140] Use 25mL / L Vegazym P-CS ( A 20 g / L solution of a lightly acidified lemon peel extract was hydrolyzed with 1% ethyl acetate (Geisenheim) (a commercial enzyme preparation showing rhamnosidase and glucosidase activity) in tap water at 40°C for 24 hours under stirring. The product was extracted three times with 40% of the reaction volume of ethyl acetate by stirring for 10 minutes and then the phases were separated by centrifugation at 17.000 x g for 20 minutes. The combined organic phases were washed twice with 40% of the reaction volume of tap water and then dried under vacuum. The hydrolyzate obtained after 24 hours contained 0.01 wt.-% of eriocitrin, 12.8 wt.-% of eriocitrin-7-O-glucoside and 69.5 wt.-% of eriocitrin.

[0141] The purification of the crude extract was carried out by precipitation. The crude extract was dissolved in ethanol at 40°C and water was added to precipitate the target compound. After filtration, the product contained 0.01 wt.-% of eriocitrin, 3.90 wt.-% of eriocitrol-7-O-glucoside and 76.24 wt.-% of eriocitrol.

[0142] Example 6: Preparation of flavoring composition by hydrolysis of lemon peel extract with citrate hydrolase

[0143] Lemon peel extract (300 g) and tartaric acid (39 g) were dissolved in water / acetone (2700 g). The mixture was placed in an autoclave. Hydrolysis began after reaching a temperature of 120° C. and a pressure of 5 bar. The reaction lasted for 35 hours and ended. After the obtained black liquid had cooled, it was taken out of the autoclave.

[0144] By adding water, the target compound was precipitated. The solid material was obtained by filtration and hydrolyzed with 50 ml / L of Vegazym P-CS switch enzyme at 50°C for 24 hours. The target compound was recovered by ethyl acetate extraction and concentration. The extract contained 0.01 wt.-% of eriocitrin, 3.4 wt.-% of eriocitrin-7-O-glucoside and 72.6 wt.-% of eriocitrin.

[0145] Example 7: Taste Improvement of Vegan Patties

[0146] The vegan patties produced contained the following ingredients: water, legume protein isolate, sunflower oil, legume protein concentrate, coconut oil, methylcellulose, fiber, salt, starch, lactic acid, and sodium diacetate. Water, thickener, and starch were mixed with water and the pH was adjusted, followed by the addition of protein, and then fiber and oil ingredients. Finally, the taste masking ingredients according to Table 4 were added. The ingredients were mixed thoroughly and the dough was formed into patties. The patties were baked in an oven at 200°C. After cooling the patties, the patties were sliced ​​and the samples were numbered for blind tasting by a panel.

[0147] Table 4: Sensory profile of vegan patties with the composition of the invention (No. 4) compared to pure bitter masking compound

[0148]

[0149] The vegan patty tasted bitter with a toasty, bready flavor (Table 4, entry 1). As described in EP1258200A1, the addition of bitter masking compounds eriodictyol and homoeriodictyol improved the taste profile, with homoeriodictyol reducing bitterness more than eriodictyol. However, the flavoring composition of the present invention derived from lemon peel extract had the best taste improvement and bitter masking properties.

[0150] Example 8: Flavoring composition

[0151] The mixture can be compared with other taste modulating compounds to impart a taste modulating sensory effect. Naringenin and hesperetin were used as examples and the results are shown in Table 5. A masking mixture containing three parts of hesperetin, two parts of naringenin and two parts of a citrus hydrolysate of the present invention (55 wt.-% ED, 11.1 wt.-% EDMG, 1.5 wt.-% EC) at a dose of 50 mg / kg was used to test naringenin, hesperetin and homoeriodictyol (Table 5, No. 1-3) for comparison. The compounds and mixtures were all dissolved in water and 500 mg / kg of caffeine was added as a bittering agent. The panelists were asked to rate the bitterness intensity of each sample in a pair of samples on a scale of 1-100. The results showed that the masking mixture significantly (t-test = 0.0039) masked the bitterness of the caffeine solution (Table 5, No. 4). The bitter masking activity is higher than homoeriodictyol (in direct comparison test table 5, number 3, reduction of -6.1%), even higher than hesperetin (in direct comparison test table 5, number 2, reduction of -16.4%), and is highest in direct comparison with naringenin (test table 5, number 1, reduction of -21.7%). This shows that naringenin and hesperetin alone are not effective bitter masking compounds, but formulated with the citrus hydrolysate of the present invention, they form a significant bitter masking activity, and the bitter masking activity is therefore at least higher than eriodictyol, although the masking mixture contains only about 5 mg / kg of eriodictyol. The mixture can be obtained by mixing the citrus hydrolysate of the present invention with hydrolysates from orange (producing hesperetin), grapefruit or bergamot (producing naringenin) or bitter orange and lime and other citrus fruits.

[0152] Table 5: Bitter taste masking activity of the compositions of the present invention compared to the taste modulating compounds naringenin, hesperetin and homoeriodictyol

[0153]

[0154] Example 9: Taste improvement of protein foods

[0155] A protein-rich food was prepared by adding 100 g of hot water to 0.5 g of agar (CERO Agar Gelidium Type 8952), stirring at 750 rpm at 55° C. and finally adding 10 wt.-% of pea (formulation 1) and soy protein (formulation 2) concentrates. The mixture was homogenized and finally filled into cups. By cooling to 8° C. within 20 minutes, the samples thickened and formed a homogeneous and stable matrix. Each sample was paired with a sample having a composition of the invention (i.e., the lemon peel hydrolyzate of sample numbered 4 in Table 3) for tasting. The samples were numbered and tasted by five perfumers. The intensity of the sensory attributes is expressed on a scale of 0-10.

[0156] Table 6: Paired comparison of pea protein fortified products with and without lemon peel hydrolysate

[0157] property Preparation 1 (pea) Formulation 1 + 100 mg / kg lemon peel hydrolysate (Table 3, sample No. 4) Qingxiang 3 3.5 Potato 3.5 3 Earthy 2 0 Neroli 2.5 0 Qingxiang 6 6 Astringency 5 4 bitterness 8 4 Pea flavor 9 6 Umami 0 1.5

[0158] Table 7: Paired comparison of soy protein fortified products with / without lemon peel hydrolysate

[0159] property Preparation 2 (soybean) Formulation 2 + 100 mg / kg lemon peel hydrolysate (Table 3, sample No. 4) Yeasty 9 8 Musty 3 4 bitterness 6.5 4 sour 5 4 Burnt smell 8 8.5

[0160] The sensory data showed that, according to the sample No. 4 in Table 3, by adding 100 mg / kg of lemon peel hydrolyzate, the foreign flavors such as bitterness, astringency, sourness, and pea flavor could be reduced.

Claims

1. A flavoring composition comprising eriocitrin, eriocitrin-7-O-glucoside and eriocitrin, wherein: The content of eriodictyol is 30wt% to 75wt%, The content of eriocitrin is 0.25wt% to 10wt%, and The content of eriodictyol-7-O-glucoside is 1wt% to 40wt%, Each is based on the dry weight of the flavoring composition, wherein the sum of the percentages of the various components in the composition equals 100%.

2. The flavoring composition according to claim 1, wherein the composition further comprises neoeriocitrin.

3. The flavoring composition according to claim 2, wherein The content of neoeriocitrin is 0.01 wt % to 40 wt %.

4. The flavoring composition according to claim 2, wherein The content of neoeriocitrin is 0.1 wt % to 20 wt %.

5. The flavoring composition according to claim 2, wherein The content of neoeriocitrin is 0.25 wt % to 10 wt %.

6. The flavoring composition according to claim 1, wherein the composition comprises at least one additional flavoring substance selected from the group consisting of: Flavoring ingredients and flavoring preparations.

7. The flavoring composition according to claim 1, wherein the composition comprises at least one additional flavoring substance selected from the group consisting of: Fatty flavoring substances, Seasoning ingredients, Juice from concentrate.

8. The flavoring composition according to claim 1, wherein the composition comprises at least one sweetening substance selected from the group consisting of: Natural sweeteners; Synthetic sweeteners.

9. Use of a flavoring composition according to any one of claims 1 to 8 for masking and / or reducing at least one undesirable taste characteristic in a formulation.

10. Use of a flavoring composition according to any one of claims 1 to 8 for masking and / or reducing at least one undesirable taste characteristic of a formulation.

11. Use according to claim 9 or 10, wherein the at least one undesirable taste characteristic is selected from the group consisting of bitterness, astringency, metallic taste, sourness, fermentation, pea taste and yeast taste.

12. The use according to claim 9 or 10, wherein the amount of the flavoring composition is 0.05 wt%, based on the total weight of the preparation.

13. The use according to claim 9 or 10, wherein the amount of the flavoring composition is 0.02 wt%, based on the total weight of the preparation.

14. The use according to claim 9 or 10, wherein the amount of the flavoring composition is 0.001 wt% to 0.01 wt%, based on the total weight of the preparation.

15. Use according to claim 9 or 10, wherein the formulation is selected from the group consisting of formulations suitable for consumption.

16. Use according to claim 9 or 10, wherein the preparation is selected from the group consisting of foods, preparations for recreation, semi-finished products and oral hygiene products.

17. Use according to claim 9 or 10, wherein the preparation is selected from the group consisting of preparations for recreation, beverages, semi-finished products and oral hygiene products.

18. A method for masking and / or reducing at least one undesirable taste characteristic in / of a formulation, comprising or consisting of the following steps: a) providing at least one formulation; b) providing a flavoring composition according to any one of claims 1 to 8; c) contacting and mixing the formulation provided in step a) and the flavoring composition provided in step b); as well as d) Obtaining preparations with improved taste.

19. The method according to claim 18, wherein the formulation provided in step a) is selected from the group consisting of formulations suitable for consumption.

20. The method according to claim 18, wherein the preparation provided in step a) is selected from the group consisting of a food, a preparation for recreation, a semi-finished product and an oral hygiene product.

21. The method according to claim 18, wherein the preparation provided in step a) is selected from the group consisting of preparations for recreation, beverages, semi-finished products and oral hygiene products.

22. A method for producing a flavoring composition as claimed in any one of claims 1 to 8, comprising or consisting of the following steps: (i) providing a natural extract from at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora tobiracola, Chrysanthemum morifolium, Chrysanthellum indicum, Citrus species, Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum articulatum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus europaeus, Buddlejaparviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurnniveum, Arnica longifolia, Caryopteris incana, Mentha aquatica and 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 20°C to 60°C, optionally under stirring for 0.5 to 48 hours; (v) obtaining a flavoring composition according to any one of claims 1 to 5; (vi) optionally: purifying the flavoring composition obtained in step (v); and optionally: (vii) adding additional flavoring substances to the flavoring composition; and (viii) obtaining a flavoring composition according to any one of claims 1 to 8.

23. The method of claim 22, wherein an additional sweetening substance is added to the flavoring composition in step (vii).

24. The method of claim 22, wherein step (iv) is performed at a temperature in the range of 40°C to 60°C.

25. The method of claim 22, wherein step (iv) is performed under stirring for 2 to 24 hours.

26. The method of claim 22, wherein step (iv) is performed under stirring for 4 to 12 hours.

27. The method according to claim 22, wherein the flavoring substance added in step (vii) is as defined in claim 6 or 7.

28. The method according to claim 22, wherein the sweetening substance added in step (vii) is as defined in claim 8.

29. The method according to claim 27 or 28, wherein the flavoring composition obtained in step (viii) is the flavoring composition according to claim 6, 7 or 8.

30. The method of claim 22, wherein the plant in step (i) is selected from the group consisting of C. bergamia and C. limon.

31. The method of claim 22, wherein the hydrolase provided in step (ii) is a glucosidase or a rhamnosidase.

32. A method for making a flavoring composition as claimed in any one of claims 1 to 8, comprising or consisting of the following steps: (i) providing a natural extract from at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involucrate, Balanophora tobiracola, Chrysanthemum morifolium, Chrysanthellum indicum, Citrus species, Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum articulatum, Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica, Lycopus europaeus, Buddlejaparviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichiurnniveum, Arnica longifolia, Caryopteris incana, Mentha aquatica and Impatiens glandulifera; (ii) providing at least one natural and non-volatile organic acid; (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 of 100° C. to 160° C. for 4 hours to 48 hours; (v) obtaining a flavoring composition according to any one of claims 1 to 5; (vi) optionally: purifying the flavoring composition obtained in step (v); and optionally: (vii) adding additional flavoring substances to the flavoring composition; and (viii) obtaining a flavoring composition according to any one of claims 1 to 8.

33. The method of claim 32, wherein in step (vii) an additional sweetening substance is added to the flavoring composition.

34. The method of claim 32, wherein the natural and non-volatile organic acid is 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.

35. The method of claim 32, wherein step (iv) is performed at a temperature of 110°C to 150°C.

36. The method of claim 32, wherein step (iv) is performed for a duration of 8 to 40 hours.

37. The method of claim 32, wherein step (iv) is performed for a duration of 12 hours to 36 hours.

38. The method according to claim 32, wherein the flavoring substance added in step (vii) is as defined in claim 6 or 7.

39. The method according to claim 32, wherein the sweetening substance added in step (vii) is as defined in claim 8.

40. The method according to claim 38 or 39, wherein the flavoring composition obtained in step (viii) is the flavoring composition according to claim 6 or 7 or 8.

41. The method of claim 32, wherein the plant in step (i) is selected from the group consisting of C. bergamia and C. limon.

42. The flavoring composition according to claim 1, obtained by the method of any one of claims 22 to 41.

43. Use according to claim 9 or 10, wherein the used flavouring composition is obtained by the method according to any one of claims 22 to 41.

44. The method of claim 18, wherein the flavoring composition provided is obtained by the method of any one of claims 22 to 41.

Images