Flavoring compositions for improving taste

Abstract

The present invention relates to flavoring compositions comprising eriocitrin, eriodictyol-7-O-glucoside, and eriodictyol for improving taste. The present invention also relates to methods for producing such flavoring compositions, as well as their use for improving taste and methods for improving taste characteristics in preparations.

Description

[Technical Field]

[0001] The present invention relates to flavoring compositions comprising eriocitrin, eriodictyol-7-O-glucoside, and eriodictyol for improving taste. The present invention also relates to methods for producing such flavoring compositions, as well as their use for improving taste and methods for improving taste characteristics in preparations. [Background technology]

[0002] There is a constantly growing need for new substances or compositions for improving the taste characteristics of preparations such as foods, beverages, or hygiene products. Various substances with unpleasant tastes, such as bitter, sour, and astringent substances, may be present in foods and beverages, which, on the one hand, are reasonably desirable and distinctive (e.g., caffeine in tea or coffee, tannins in red wine or green tea, quinine in so-called bitter lemon drinks, saponins or isoflavonoids or their glycosides in soy milk, hop extracts in beer, fruit acids or edible acids in sweet fruit juices). However, on the other hand, they may significantly reduce value. An unpleasant taste is often further intensified by an unpleasant odor; for example, in soy milk, which often has a bitter and astringent taste, the commonly described description "beany" is also described as unpleasant.

[0003] Bitter taste is often caused by certain substances that bind to special bitter receptors on taste cells (found in the so-called taste buds on the tongue), sending signals via a neurochemical cascade to the brain, which then produces a defensive response and a negative taste impression (see non-patent document 1).

[0004] Astringency is caused by the precipitation of proline-rich proteins in saliva by astringents, such as metal salts or tannins. The normally homogeneous saliva, which acts as a "lubricant," now contains denatured proteins, which reduce its lubricity and result in a rough or dry sensation in the mouth, which is also experienced as astringent (Non-Patent Document 2).

[0005] Sour taste is caused by proton acids. The so-called titratable proton concentration is then more decisive for the sour impression than pH; for example, a hydrochloric acid solution with the same pH as a malic acid solution tastes much less sour in comparison. Generally, unpleasant sourness is significantly mitigated by combining it with sweet flavoring materials, primarily sugar, or with more salty-tasting substances, primarily sodium chloride, while sourness is perceived as much more unpleasant by bitter or astringent-tasting substances.

[0006] Known taste modulating substances for modifying these taste impressions include eriodictyol and homoeriodictyol. The bitterness-masking activity of eriodictyol was first described in U.S. Patent No. 5,629,999, in which Eriodictyon californicum was designated as the source of eriodictyol. This application does not disclose information about the production or natural sources from which eriodictyol may be obtained. It also does not describe the effect of eriodictyol when coexisting with other taste modulating substances.

[0007] Eriodictyol is a flavanone. Flavanones can generally be obtained by organic acid-catalyzed hydrolysis of the respective flavanone glycosides, as described in Patent Document 2. However, this application only discloses the hydrolysis of easily recoverable components, such as hesperidin and phloridzin, that are 90% or more pure. However, no information is disclosed regarding the hydrolysis and purification of less pure materials. It is well known that the hydrolysis of less pure materials results in the formation of undesirable minor components that impart off-notes, such as phenols, to the product. Therefore, the disclosed method does not teach a method for economically producing eriodictyol from natural sources.

[0008] Patent Document 3 describes compositions made from lemons rich in eriocitrin and eriodictyol for use as antioxidants and anti-inflammatory agents. No information is disclosed about the taste-modulating properties of the compositions, nor about the manufacturing process.

[0009] Patent Document 4 describes a method for obtaining eriocitrin-rich extracts from citrus fruits by solvent extraction followed by adsorption onto a polymer resin. However, the obtained product exhibited an odor similar to Chinese herbal medicine. It is well known that polyphenol-containing materials exhibit off-notes and browning depending on the processing and storage conditions. This application does not disclose a process for producing a lemon extract without off-notes or for imparting taste-modulating functionality.

[0010] Patent Document 5 describes a process for obtaining an eriocitrin-rich extract from citrus fruits by solvent extraction followed by resin adsorption. The inventors of this patent application address the off-note problem associated with polymeric resins by using a resin modified with phenol-formaldehyde. Here, eriocitrin is adsorbed not only physically onto the surface but also chemically by ion exchange due to basic amino groups and weakly acidic phenolic groups. The off-notes are reduced by this process. However, this invention does not disclose taste-modulating compositions according to the present invention that contain compounds more active than eriocitrin.

[0011] Patent Document 6 describes compositions containing eriodictyol and eriocitrin, but does not describe their (synergistic) effect on masking bitterness.

[0012] Patent Document 7 describes compositions comprising eriocitrin and neoeriocitrin. However, the compositions are intended for medical purposes to treat inflammation and / or metabolic syndrome. The (synergistic) effect on bitterness masking is not described.

[0013] Non-Patent Document 3 describes eriocitrin and neoeriocitrin in bergamot peel, but does not describe their (synergistic) effect on masking bitterness.

[0014] Patent Document 8 describes the use of eriodictyol and / or homoeriodictyol as a bitterness-masking agent in food and beverage compositions. However, it does not describe a synergistic improvement in the bitterness-masking effect of eriodictyol. [Prior art documents] [Patent documents]

[0015] [Patent Document 1] European Patent Publication No. 1258200A2 [Patent Document 2] European Patent Publication No. 2017272A2 [Patent Document 3] US Patent No. 10596185B2 [Patent Document 4] Japanese Patent Publication No. 2000217560A [Patent Document 5] European Patent Publication No. 2223930A1 [Patent Document 6] European Patent Publication No. 1783193A1 [Patent Document 7] US Patent Publication No. 2017 / 0014439A1 [Patent Document 8] European Patent Publication No. 2756765A1 [Non-patent literature]

[0016] [Non-Patent Document 1] Wolfgang Meyerhof, Reviews of Physiology, Biochemistry and Pharmacology, 2005, 154, pp. 37-72 [Non-patent document 2] Isabelle Lesschaeve and Ann C. Noble, American Journal of Clinical Nutrition, 2005, Vol. 81, p. 330-335 [Non-patent document 3] Mandalari et al., "Characterization of Flavonoids and Pectins from Bergamot (Citrus bergamia Risso) Peel, a Major Byproduct of Essential Oil Extraction," JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 54, no. 1, p. 14, December 2005. Summary of the Invention [Problem to be solved by the invention]

[0017] It was therefore a primary object of the present invention to provide a flavoring composition that is capable of improving the taste characteristics, preferably bitterness and astringency, of a preparation, that can be commercially produced using an economical process, and that preferably does not exhibit off-notes. [Means for solving the problem]

[0018] This object has been primarily achieved in a first aspect of the present invention by providing a flavoring composition comprising eriocitrin, eriodictyol-7-O-glucoside and eriodictyol, and optionally neoeriocitrin, wherein If present, neoeriocitrin is contained in an amount of 0.1% to 40% by weight, preferably 0.1 to 10% by weight; Eriocitrin is contained in an amount of 0.1 to 40% by weight, preferably 0.1 to 10% by weight, Eriodictyol-7-O-glucoside is contained in an amount of 0.2% by weight to 60% by weight, preferably 1% by weight to 40% by weight, Eriodictyol is contained in an amount of 5 to 79% by weight, preferably 10 to 77% by weight, preferably 20 to 76% by weight, preferably 30 to 75% by weight, each depending on the dry weight of the flavoring composition.

[0019] 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 percentage. Therefore, the dry weight is preferably measured by subtracting the moisture content from the total weight of the composition whose dry weight is to be determined. Preferably, the moisture content is determined by Karl Fischer titration, loss on drying, or by a halogen moisture analyzer. DETAILED DESCRIPTION OF THE INVENTION

[0020] In one embodiment of the present invention, the flavoring composition comprises neoeriocitrin in an amount of 0.1% to 40% by weight, preferably 0.1 to 10% by weight, eriocitrin in an amount of 0.1% to 40% by weight, preferably 0.1 to 10% by weight, eriodictyol-7-O-glucoside in an amount of 0.2% to 60% by weight, preferably 1 to 40% by weight, and eriodictyol in an amount of 5% to 90% by weight, preferably 30 to 80% by weight.

[0021] In another embodiment of the present invention, the flavoring composition comprises neoeriocitrin in an amount of 0.1% to 40% by weight, preferably in an amount of 0.1 to 10%, and eriocitrin in an amount of 0.1% to 40% by weight, preferably in an amount of 0.1 to 10% by weight.

[0022] In yet another embodiment of the present invention, the flavoring composition comprises neoeriocitrin in an amount of 0.1% to 40% by weight, preferably in an amount of 0.1 to 10% by weight, and eriodictyol-7-O-glucoside in an amount of 0.2% to 60% by weight, preferably in an amount of 1 to 40% by weight.

[0023] In one embodiment of the present invention, the flavoring composition comprises neoeriocitrin in an amount of 0.1% to 40% by weight, preferably in an amount of 0.1 to 10% by weight, and eriodictyol in an amount of 5% to 90% by weight, preferably in an amount of 30 to 80% by weight.

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

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

[0026] In yet another embodiment of the present invention, the flavoring composition comprises eriodictyol-7-O-glucoside in an amount of 0.2% to 60% by weight, preferably in an amount of 1 to 40% by weight, and eriodictyol in an amount of 5% to 90% by weight, preferably in an amount of 30 to 80% by weight.

[0027] In one embodiment of the present invention, the flavoring composition comprises neoeriocitrin in an amount of 0.1% to 40% by weight, preferably 0.1 to 10% by weight, eriocitrin in an amount of 0.1% to 40% by weight, preferably 0.1 to 10% by weight, and eriodictyol-7-O-glucoside in an amount of 0.2% to 60% by weight, preferably 1 to 40% by weight.

[0028] In a particularly preferred embodiment of the present invention, the flavoring composition comprises eriocitrin in an amount of 0.1% to 40% by weight, preferably in an amount of 0.1 to 10% by weight, eriodictyol-7-O-glucoside in an amount of 0.2% to 60% by weight, preferably in an amount of 1 to 40% by weight, and eriodictyol in an amount of 5% to 90% by weight, preferably in an amount of 30 to 80% by weight.

[0029] In another embodiment of the present invention, the flavoring composition comprises 0.1% to 40% by weight, preferably 0.1 to 10% by weight, neoeriocitrin, 0.2% to 60% by weight, preferably 1 to 40% by weight, eriodictyol-7-O-glucoside, and 5% to 90% by weight, preferably 30 to 80% by weight, of eriodictyol.

[0030] Neoeriocitrin (I) is the 7-O-glycoside of the flavanone eriodictyol and the disaccharide neohesperidose (2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside). The term "neo" refers to the glycosyl moiety.

[0031] [ka]

[0032] Eriocitrin (II) is a disaccharide derivative of eriodictyol, consisting of eriodictyol substituted at the 7-position via a glycosidic bond with a rutinose 6-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl moiety. Essentially, eriocitrin acts as an antioxidant.

[0033] [ka]

[0034] Eriodictyol-7-O-glucoside (III) is a derivative of eriodictyol that has a flavonoid moiety O-glycosidically linked to a carbohydrate moiety at the C7 position.

[0035] [ka]

[0036] Eriodictyol (IV) is a flavanone extracted from yerba santa (Eriodictyon californicum) substituted with hydroxy groups at the 5, 7, 3', and 4' positions, respectively.

[0037] [ka]

[0038] It has surprisingly been found that the flavoring compositions according to the invention, in such combinations, are able to synergistically improve certain taste characteristics, preferably masking bitter, astringent, metallic, sour, fermented, pea-like and yeasty tastes in preparations to a much greater extent than the taste improvement imparted by neoeriocitrin, eriocitrin, eriodictyol-7-O-glucoside and eriodictyol alone, respectively.

[0039] Whenever there is an inconsistency between the name of a substance and the structural formula, the structural formula should be considered as the reference. Since the structures as shown above can occur as stereoisomers, R and S enantiomeric forms are also included in the context of the present invention. Furthermore, the glucosides can be attached to the flavonoid moiety via α- or β-glucosidic bonds. Therefore, these are also described in terms of the compounds and structures as listed above in the context of the present invention.

[0040] One embodiment of the present invention relates to a flavoring composition, wherein compounds (A) are obtained from natural sources by chemical or enzymatic hydrolysis.

[0041] "Natural source" in the context of the present invention means any material that grows naturally and is not produced by any artificial chemical reaction initiated by humans. "Natural source" is preferably to be understood in the context of the present invention as plant matter.

[0042] Chemical hydrolysis is a process in which chemical bonds are broken by the addition of water molecules. This reaction can be carried out, for example, at elevated temperatures.

[0043] Enzymatic hydrolysis is a process in which chemical bonds are broken with the aid of enzymes along with the addition of water. Enzymes capable of carrying out hydrolysis reactions are called hydrolases.

[0044] In another embodiment of the invention, the compounds (A) of the flavoring composition are selected from the group consisting of Gleditsia caspia (Caspian honey locust), Balanophora involucrate, Balanophora tobiracola (Yellow honey locust), Chrysanthemum morifolium (Chrysanthemum), Chrysanthellum indicum, Citrus species, preferably C. bergamia and C. limon, Dracocephalum rupestre, Viscum liquidambaricolum, Viscum coloratum, Viscum alticulatum, Flatstick mistletoe (Lasianthus articulatum), Lasianthus japonica, Lophophytum leandri, Elsholtzia bodinieri, Umbellularia californica (California bay tree), Lycopus europaeus (Lycopus europaeus), Buddleja parviflora, Eminium spiculatum, Coreopsis tinctoria (Coreopsis), Cyclotrichiurn niveum, Arnica longifolia, Caryopteris The compound is obtained from a natural source from a plant selected from the group consisting of Mentha incana, Mentha aquatica, and Impatiens glandulifera.

[0045] From the standpoint of the present invention, it is particularly preferred that the flavoring composition is obtained from a citrus source, particularly preferably Citrus bergamia and Citrus limon, and it is further preferred if the flavoring composition is obtained from a citrus extract by chemical or enzymatic hydrolysis.

[0046] Yet another embodiment of the present invention relates to a flavoring composition, which comprises at least one additional flavoring substance selected from the group consisting of the following substances: Aliphatic flavoring substances, in particular saturated aliphatic alcohols such as ethanol, isopropanol, 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, c is-6 nonen-1-ol, trans-2,cis-6 nonadienol, aromatic aldehydes, for example, saturated aromatic aldehydes (e.g., acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, isovaleraldehyde, homoeriodictyol, hexanal, 3-methylhexanal, octanal, nonanal), or mono- or multi-unsaturated aromatic aldehydes, for example For example, 2-methylbut-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, for example, saturated ketones (e.g., 2-butanone, 2-pentanone, 2-heptanone, 2-octanone, 2-methylheptan-3-one, 2-decanone, 2-undecanone), unsaturated ketones (e.g., 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 diketol, e.g., diacetyl, acetylmethylcarbinol, 2,3-hexanedione, aliphatic acids, for example, linear 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, for example, saturated esters such as methyl acetate, methyl butyrate, methyl methyl ester, methyl 2-methylbutyrate, methyl hexanoate, ethyl acetate, ethyl butyrate, 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 cis-3 hexenyl acetate, cis-3 hexenyl butyrate, aliphatic thiols and dithiols (e.g., propanethiol, allyl mercaptan, 1-methoxy-3-dimethylbutane-3-thiol, dimethyl sulfide, dimethyl trisulfide, dipropyl sulfide, diallyl trisulfide), other aliphatic sulfur compounds, e.g., 2-mercapto-3-butanol, methylthiopropanal, 3-mercaptopentanone, 4-methoxy-2-methyl-2-mercaptobutanone, methylthiobutyrate, methylthio butyrate, methyl 3-methylthiopropionate, aliphatic nitrogen compounds such as butylamine, trimethylamine, allyl isothiocyanate, isopropyl isothiocyanate, alicyclic compounds such as alicyclic ketones such as cis-jasmone, isophorone, 4-ketoisophorone, alicyclic esters such as methyl jasmonate, hedione, terpenes such as terpene alcohols such as linalool, citronellol, geraniol, nerol, α-terpineol, menthol, 8-p-menthen-1,2-diols, fenchol, borneol, nerolidol, hotrienol, terpene aldehydes such as geranial, neral, citronellal, β-sinensal, terpene ketones such as α-ionone, (D)-carvone, (L)-carvone, nootkatone, piperitone, menthone, α-damascone, β-damascene, damascenone, terpene esters such as linalyl acetate, geranyl acetate, Citronellyl acetate, carvyl acetate, fenchyl acetate, terpene sulfur 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, α-pinene, β-pinene, ocimene, α-terpinene, γ-terpinene, β-bisabolene, valencene, terpene oxides aromatic compounds such as 1,8-cineole, rose oxide, mint lactone, menthofuran; aromatic compounds such as 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, methyl phenyl acetate, methyl benzoate, methyl salicylate, methyl cinnamate; aromatic phenols such as phenol, ortho-cresol, para-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-methylanthranilate, aromatic ethers such as vanillin, ethyl vanillin, anethole, aromatic oxides such as heliotropin, diphenyl oxide, aromatic lactones such as coumarin, dihydrocoumarin, heterocyclic compounds such as heterocyclic lactones such as γ-butyrolactone, γ-nonalactone, γ-decalactone, δ-decalactone, jasmine lactone, δ-dodecalactone, ambretride, heterocyclic furans such as furfuryl alcohol, furfural, 2-acetylfuran, theaspirane, 2-methyltetrahydrofuran Furan-3-one, furfuryl mercaptan, 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 pyrazines 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, Flavoring raw materials and flavoring preparations, for example, raw materials such as citrus (e.g., lemon, lime, mandarin, bergamot, grapefruit, bitter orange, peel or essential oils), herbs (dill, parsley, cumin, rosemary, sage, clary sage, basil, tarragon, thyme, oregano, savory, marjoram, all spices, mace, nutmeg, clove leaves, clove buds, caraway, cinnamon leaf, cinnamon), Monbark, cassia, cardamom, ginger, galangal, turmeric, coriander seeds, coriander leaves, fenugreek, juniper berries, wormwood, laurel leaves, eucalyptus, white pepper, green pepper, white pepper, carrot seeds, celery seeds, lovage leaves, asafoetida, onions, chives, garlic, mustard, horseradish, bell peppers, paprika, seaweed, valerian oil, fir needles, spearmint , Peppermint, Wintergreen, Buttercup Leaf, Blackcurrant Bud, Fennel, Star Anise, Jambu, Long Pepper, Davana, Orris, Mimosa, Cassi, Violet Leaf, Holly Leaf, Jasmine, Ylang Ylang, Cananga, Osmanthus, Angelica, Clary Sage, Ambrette Seed, Hops, Chamomile, Lavender, Rose, Geranium, Citronella, Palmarosa, Litsea Cubeba, Lemongrass, Tagetes, Neroli, Petitgrain, Essential oils, concretes, absolutes, extracts or tinctures from yerba mate, cognac oil, coffee, cola nut, cocoa, green tea, black tea, white tea, gentian, true balm, benzoic resin, Peruvian balm, cascarilla, galbanum, vetiver, labdanum, patchouli, sandalwood, cedarwood, guaiac wood, oakwood, massoi bark, vanilla pod, tonka bean, as well as their concentrated fractions; Juice concentrates, for example orange juice, lemon juice, strawberry, cherry juice or passion fruit juice concentrates, aqueous phases and recovered materials from raw materials such as citrus (lemon, lime, orange, mandarin, grapefruit), apple, pear, quince, medlar, red fruits (raspberry, strawberry, blueberry, blackberry, amelanchia (June plum), rosehip, cranberry, plum, prune, red and black currant, etc.), 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), Acetophenone, allyl caproate, α-ionone, β-ionone, anisaldehyde, anisyl acetate, anisyl formate, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, β-ionone, butyl butyrate, butyl caproate, butylidenephthalide, carvone, camphene, caryophyllene, cineole, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascone, decalactone, dihydriodide Rocumarine, dimethyl anthranilate, dodecalactone, ethoxyethyl acetate, ethyl butyrate, ethyl butyrate, ethyl caprate, ethyl caproate, ethyl crotonate, ethyl furaneol, ethyl guaiacol, ethyl isobutyrate, ethyl isovalerate, ethyl lactate, ethyl methyl butyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptylate, 4-(p-hydroxyphenyl)-2-butanone, γ-decalactone, geraniol, geranyl acetate, grapefruit aldehyde, methyl dihydrojasmonate (e.g., Hedion®), heliotropinone, 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, ci s-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, methyl butanol, methyl butyric acid, 2-methylbutyl acetate,Methyl caproate, methyl cinnamate, 5-methylfurfural, 3,2,2-methylcyclopentenolone, 6,5,2-methylheptenone, methyl dihydrojasmonate, methyl jasmonate, 2-methylmethylbutyrate, 2-methyl-2-pentenoic 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, δ- Octalactone, γ-octalactone, 2-octanol, 3-octanol, 1,3-octenol, 1-octyl acetate, 3-octyl acetate, palmitic acid, paraldehyde, phellandrene, pentanedione, phenethyl acetate, phenethyl alcohol, phenethyl isovalerate, piperonal, propionaldehyde, propyl butyrate, pulegone, pulegol, sinenal, sulfurol, terpinene, terpineol, terpinolene, 8,3-s-thiomenthanone, 4,4,2-thiomethylpentanone, thymol, δ- undecalactone, γ-undecalactone, valencene, valeric acid, vanillin, acetoin, ethyl vanillin, ethyl vanillin isobutyrate (=3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3(2H)-furanone and its derivatives (preferably homofuraneol (=2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone), homofuranol (=2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)- furanone), maltol and maltol derivatives (herein preferred is ethyl maltol), coumarin and coumarin derivatives, γ-lactones (herein preferred is γ-undecalactone, γ-nonalactone, γ-decalactone), δ-lactones (herein preferred is 4-methyl-δ-decalactone, massolactone, δ-decalactone, 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)disulfide, furfuryl mercaptan, methional, 2-acetyl-2-thiazoline, 3-mercapto-2-pentanone, 2,5-methyl-3-furanthiol, 2,4,5-trimethylthiazole, 2-acetylthiazole, 2,4-dimethyl-5-ethylthiazole azole, 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-methyltrimethylpyrazine Decanal, 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 stereoisomers, enantiomers, positional isomers, diastereomers, cis / trans isomers or epimers of these substances (not explicitly mentioned here).

[0047] Another embodiment of the present invention relates to a flavoring composition, which comprises at least one sweet tastant selected from the group consisting of the following sweeteners: Natural sweeteners, preferably plant extracts, such as sweet carbohydrates (e.g., sucrose, trehalose, lactose, maltose, melezitose, melibiose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, l-rhamnose, D-sorbose, D-mannose, D-tagatose, D-arabinose, l-arabinose, D-ribose, D-glyceraldehyde, D-allulose, maltodextrin), sugar alcohols (e.g., erythritol, threitol, arabitol, ribose, and the like. Examples of suitable amino acids include: maltitol, xylitol, sorbitol, mannitol, maltitol, isomaltitol, dulcitol, lactitol), proteins (e.g., miraculin, pentaidine, monellin, thaumatin, curculin, brazzein, mabinlin), D-amino acids (e.g., D-phenylalanine, D-tryptophan), or extracts or fractions obtained from natural sources containing these amino acids and / or proteins, as well as physiologically acceptable salts of these amino acids and / or proteins, in particular their sodium salts. , potassium, calcium or ammonium salts, neohesperidin dihydrochalcone, naringin dihydrochalcone, steviol glycoside, stevioside, steviolbioside, 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 Oside J, bayunoside 1, bayunoside 2, phlomisoside 1, phlomisoside 2, phlomisoside 3, phlomisoside 4, phloretin, phyllodulcin, abrusoside A, abrusoside B, abrusoside C, abrusoside D, cyclocarioside A, cyclocarioside I, osladin, polypodoside A, strogin 1, strogin 2, strogin 4, seriguenin A, dihydroquercetin-3-acetate, perillartine, telosmoside A15, periandrin IV, pterocarioside, cyclocarioside, mukurozioside, trans-anethole,trans-Cinnamaldehyde, bryoside, bryonoside, bryonodulcoside, carnosifloside, hesperetin, scandenoside, gypenoside, hematoxylin, cyanin, chlorogenic acid, albiziasaponin, telosmosides, gaudichaudioside, mogrosides, e.g. mogroside V, hernandulcin, monatin, glycyrrhetinic acid and derivatives thereof, in particular glycyrrhizin, preferably glycyrrhizin ammonium salt, extracts or concentrated fractions of such extracts, for example extracts of Thaumatococcus or Stevia subsp., in particular Stevia rebaudiana, swingle extracts, in particular Momordica or Siratia grosvenorii or Luo-Han-Guo, extracts of Glycyrrhiza subsp., in particular Glycyrrhyzia glabra, extracts of Hydrangea macrophylla subsp., in particular Hydrangea macrophylla serrata, extracts of Rubus subsp., in particular Rubus suavissimus, extracts of Lippia dulcis, naturally occurring sweeteners including extracts of Mycetia balansae, preferably comprising balancin A and / or balancin B, Synthetic sweeteners, preferably selected from the group consisting of magap, sodium cyclamate or other physiologically acceptable salts of cyclamic acid, acesulfame K, neohesperidin dihydrochalcone, naringin dihydrochalcone, hesperetin dihydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotam, alitam, advantam, perillartine, sucralose, ragduname, carrelam, sucrononate or sucrooctate or mixtures thereof.

[0048] Particularly preferred in view of the present invention is that the flavoring composition according to the invention comprises at least one additional sweetener selected from the group consisting of allulose, sucrose, trehalose, phloretin, naringenin, hesperetin, rubusoside, steviol glycosides (preferably rebaudioside A, rebaudioside D and rebaudioside M), mogroside V, phyllodulcin and hesperetin dihydrochalcone.

[0049] Another aspect of the invention relates to the use of a flavoring composition according to the invention for masking and / or reducing at least one undesirable taste characteristic in / of a preparation, preferably the flavoring composition is used in an amount of 0.05% by weight, more preferably in an amount of 0.02% by weight, and particularly preferably in an amount of 0.001% to 0.01% by weight, based on the total weight of the preparation.

[0050] One embodiment of the use according to the invention relates to the use of a flavoring composition according to the invention in preparations suitable for consumption, preferably selected from the group consisting of foodstuffs, recreational preparations, beverages, semi-finished products and oral hygiene products.

[0051] Preferably, the at least one undesirable taste characteristic is selected from the group consisting of bitter, astringent, metallic, sour, fermented, pea-like and yeasty.

[0052] Bitterness, astringency, and sourness are taste impressions as defined above. A metallic taste can be perceived in preparations containing heavy metals, such as multivitamin preparations containing copper, zinc, and / or magnesium. Some medications can also impart a metallic taste in the oral cavity. The off-taste of sweet glycosides, such as rebaudioside A, is described as a combination of bitter and metallic.

[0053] A fermented taste is perceptible when consuming fermented, i.e., microbiologically transformed, preparations. The taste is described as partly sour and partly savory, and while desirable in certain preparations, it can also be perceived as unwanted and unpleasant.

[0054] Pea-like taste impression describes the taste of legumes in preparations where this taste is undesirable, such as protein-rich food preparations.

[0055] The yeasty taste is particularly present in preparations prepared with yeast, such as bread, sparkling wine, or beer. In certain preparations, this yeasty taste is desirable, but in other preparations, or at high levels of yeast, it is perceived as unpleasant.

[0056] Another aspect of the present invention relates to a method for masking and / or reducing at least one undesirable taste characteristic in / of a preparation, said method comprising: a) providing at least one preparation, preferably selected from the group consisting of preparations suitable for consumption, preferably foods, recreational preparations, beverages, semi-finished products and oral hygiene products; b) providing a flavoring composition according to the present invention; c) contacting and mixing the preparation provided in step a) with the flavoring composition provided in step b); d) obtaining a preparation with improved taste; It comprises or consists of:

[0057] Particularly preferred in view of the present invention are those in which the undesirable taste characteristics are selected from the group consisting of bitter, astringent, metallic, sour, fermented, pea-like and yeasty.

[0058] In a preferred embodiment, the flavoring composition is produced or producible by a method for producing a flavoring composition as disclosed herein.

[0059] Yet another aspect of the present invention relates to a method for producing a flavoring composition according to the present invention, said method comprising the steps of: (i) providing a natural extract from at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involuculata, Balanophora tauplicacora, Chrysanthemum morifolium, Chrysanthermum indicum, Citrus species, preferably C. bergamia and C. limon, Dracocephalum rupestre, Viscum liquidum varicorum, Viscum coloratum, Viscum alticulatum, Lucianthus japonica, Lophophytum leandrii, Ersholtzia bodinieri, Umbellaria californica, Lycops europaeus, Buddleia parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichurn niveum, 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 at least one hydrolase provided in step ii); (iv) incubating the mixture obtained in step iii) at a temperature in the range of 20-60°C, preferably 40-60°C, optionally under stirring, for a duration of 0.5-48 hours, preferably 2-24 hours, preferably 4-12 hours; (v) obtaining a flavoring composition according to the present invention; (vi) optionally: purifying the flavoring composition obtained in step (v); and optionally: (vii) adding additional flavoring and / or sweetening substances to the flavoring composition, preferably as defined herein; (viii) obtaining a flavoring composition according to the invention, preferably comprising additional flavoring and / or sweetening substances as defined herein; It comprises or consists of:

[0060] Furthermore, the present invention relates to a method for producing a flavoring composition according to the invention, which method comprises the steps of: (i) providing a natural extract from at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involuculata, Balanophora tauplicacora, Chrysanthemum morifolium, Chrysanthermum indicum, Citrus species, preferably C. bergamia and C. limon, Dracocephalum rupestre, Viscum liquidum varicorum, Viscum coloratum, Viscum alticulatum, Lucianthus japonica, Lophophytum leandrii, Ersholtzia bodinieri, Umbellaria californica, Lycops europaeus, Buddleia parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica, and Impatiens glandulifera; (ii) providing at least one naturally occurring 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 at least one natural non-volatile organic acid provided in step ii); (iv) incubating the mixture obtained in step iii) at a temperature in the range of 100-160°C, preferably 110-150°C, for a duration of 4-48 hours, preferably 8-40 hours, preferably 12-36 hours; (v) obtaining a flavoring composition according to the present invention; (vi) optionally: purifying the flavoring composition obtained in step (v); and optionally: (vii) adding additional flavoring and / or sweetening substances to the flavoring composition, preferably as defined herein; (viii) obtaining a flavoring composition according to the present invention, preferably as defined herein; It comprises or consists of:

[0061] Furthermore, the present invention relates to a method for producing a flavoring composition according to the invention, which method comprises the steps of: (i) providing a natural extract from at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involuculata, Balanophora tauplicacora, Chrysanthemum morifolium, Chrysanthermum indicum, Citrus species, preferably C. bergamia and C. limon, Dracocephalum rupestre, Viscum liquidum varicorum, Viscum coloratum, Viscum alticulatum, Lucianthus japonica, Lophophytum leandrii, Ersholtzia bodinieri, Umbellaria californica, Lycops europaeus, Buddleia parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica, and Impatiens glandulifera; (ii) providing at least one naturally occurring 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 at least one natural non-volatile organic acid provided in step ii); (iv) incubating the mixture obtained in step iii) at a temperature in the range of 100-160°C, preferably 110-150°C, for a duration of 4-48 hours, preferably 8-40 hours, preferably 12-36 hours; (v) obtaining a flavoring composition according to the present invention; (vi) optionally: purifying the flavoring composition obtained in step (v); (vii) providing at least one hydrolase; (viii) mixing the composition obtained in step (v) or step (vi) with at least one hydrolase provided in step (vii); (ix) incubating the mixture obtained in step (viii) at a temperature in the range of 20-60°C, preferably 40-60°C, optionally under stirring, for a duration of 0.5-48 hours, preferably 2-24 hours, preferably 4-12 hours; (x) obtaining a flavoring composition according to the present invention; (xi) optionally, purifying the flavoring composition of step (x) obtained; and optionally: (xii) adding additional flavoring and / or sweetening substances to the flavoring composition, preferably as defined herein; (xiii) obtaining a flavoring composition according to the invention, preferably comprising additional flavoring and / or sweetening substances as defined herein; It comprises or consists of:

[0062] In steps (v) and (x) of the above process, a flavoring composition according to the present invention is obtained. In both cases, the flavoring composition is according to the present invention. However, in the composition obtained in step (x) of the above process, the amount of eriodictyol is further increased.

[0063] Preferably, in the present text, in the context of the above method, the term "composition according to the invention" refers to the composition obtained in step (v).

[0064] Preferably, in the present text, in the context of the above method, the term "composition according to the invention" refers to the composition obtained in step (x).

[0065] Preferably, in the present text, in the context of the above method, the term "composition according to the invention" refers to the composition obtained in steps (v) and (x).

[0066] Preferably, in the process according to the invention, in step (ii) or (vii) providing at least one natural non-volatile organic acid, the incubation in step (iv) is carried out at a pressure in the range of 2 to 6.5 bar, preferably in the range of 3 to 6 bar, preferably in the range of 3.5 to 5.5 bar, preferably in the range of 4 to 5 bar.

[0067] In view of the present invention, it is preferred that the purification in step vi) of the process according to the 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.In view of the process for producing a flavoring composition, it is particularly preferred that a combination of methods selected from absorption, adsorption, chromatography, crystallization, precipitation, liquid-liquid extraction, solid-liquid extraction, filtration, drying or freeze-drying is used.

[0068] One embodiment of the method for producing 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 C. bergamia and C. limon.

[0069] Another embodiment of the process for producing a flavoring composition according to the present invention relates to a process, wherein the hydrolase provided in step (ii) or step (vii) is a glucosidase and / or a rhamnosidase.

[0070] Glucosidases are enzymes capable of degrading complex carbohydrates by cleaving the carbohydrate bonds between sugar monomers.

[0071] Rhamnosidase is an enzyme that catalyzes the hydrolysis of terminal non-reducing L-rhamnose.

[0072] Another aspect of the present invention relates to a flavoring composition according to the present invention, which is obtained or obtainable by a process for producing a flavoring composition according to the present invention.

[0073] The present invention also relates to the use of a flavoring mixture as described herein, the flavoring composition used being obtained or obtainable by a process for producing a flavoring composition according to the invention.

[0074] The present invention is further characterized by illustrative, non-limiting examples. [Example]

[0075] [Example 1] Paired Comparison Test A training panel was given different samples containing the bitter substances caffeine (500 mg / kg), quinine (10 mg / kg), and naringin (100 mg / kg). Caffeine is the bittering agent in coffee and coffee-type beverages, quinine is used as a food additive in flavored tonics or energy drinks, and naringin is the bittering agent in grapefruit juice. Each test contained a different amount of bitter-masking substances or their mixtures. During the test, panelists wore nose clips to eliminate any olfactory impressions. These tests are called bitter-duo tests.

[0076] In the first test, the bitter samples described above were mixed with 10 mg / kg of eriodictyol-7-O-glucoside with a purity of 95% or higher. No significant bitterness-reducing effect was observed (p<0.05). The data are shown in Table 1. At concentrations above 50 mg / kg, eriodictyol-7-O-glucoside even exhibited a bitter note.

[0077] [Table 1]

[0078] In the second test, bittering agents were mixed with 50 mg / kg of eriocitrin with a purity of 95% or higher, and the bitterness-masking effect was evaluated by a panel. No significant bitterness-masking effect was observed (p>0.05). The data are shown in Table 2.

[0079] [Table 2]

[0080] Another test was set up using samples containing 10 mg / kg quinine and 50 mg / kg eriodictyol (ED) alone or the inventive flavoring composition containing eriodictyol-7-O-glucoside (EDMG) and neoeriocitrin (NEC), eriodictyol (EC). The synergistic effect of EDMG, EC, and ED was found to significantly improve taste-masking activity compared to pure eriodictyol. The same effect was observed when neoeriocitrin was used instead of eriodictyol. The weight percentages are based on the dry weight of the flavoring composition. The results are shown in Table 3.

[0081] [Table 3]

[0082] [Example 2] Preparation of a flavoring composition from lemon peel extract Lemon peel extract (300 g) and tartaric acid (39 g) are dissolved in water / acetone (2700 g). The mixture is charged into an autoclave. Hydrolysis begins after reaching a temperature of 120°C and a pressure of 5 bar. The reaction is complete after 35 hours. The resulting black liquid is removed from the autoclave after cooling.

[0083] The target compounds are precipitated by adding water. The solid phase is separated by filtration. After drying, 126 g of solid product is obtained, which contains eriodictyol (56.10 g), eriodictyol-7-O-glucoside (33.06 g), and eriocitrin (0.68 g).

[0084] Purification of the precipitated extract is carried out by separation of the target compounds by adsorption / absorption on a solid phase. In this particular example, the precipitated extract is purified by adsorption on activated carbon material and recovery of the target compounds by elution with various solvents. A column (surface: 1400 m) of activated carbon was used. 2 / g; Bed volume: 370 kg / m; Particle size: 7-75 μm; Particle size d 50 The column (=30 pm) is conditioned with 7.5 bed volumes of water / acetone. The precipitated extract is rinsed through the conditioned column. A first pass of the product solution with a bed volume ratio of 3.5:1 is drawn off. This first pass is called the first fraction. The target compounds are adsorbed onto the stationary phase. Next, these components are stepwise desorbed with water, methanol, ethanol, propan-2-ol, ethyl acetate, and t-methyl butyl ether. Elution occurs at an eluent ratio of 4:1 to the column volume. These fractions range in color from brownish or slightly yellow to clear and colorless. The highest content of eriocitrin and eriodictyol-7-O-glucoside is eluted in the fraction fraction with water and methanol, preferably with methanol. The highest yield of eriodictyol, with the least color, is eluted in the methanol fraction. Elution of eriodictyol can be carried out similarly with ethanol, propan-2-ol, and ethyl acetate. The methanol fraction contained eriodictyol (58.0 g), eriodictyol-7-O-glucoside (41.7 g), and eriocitrin (0.3 g).

[0085] To achieve the same purity as using methanol as described herein, solvents other than methanol, mixtures of solvents, and different CV ratios can be used. The column volume ratio (CV) is the ratio of the column bed volume to the volume of the solution flowing through the column. The products were evaluated by a sensory panel (n=20). Bitterness-masking activity was assessed according to Example 1, and it was observed that lemon peel extract was able to significantly mask the bitterness of a quinine model solution.

[0086] [Example 3] Preparation of a flavoring composition from lemon peel extract Lemon peel extract (100 g) and citric acid (13 g) are dissolved in water / acetone (900 g). The mixture is charged into an autoclave. Hydrolysis begins after reaching a temperature of 120 °C and a pressure of 5 bar. The reaction is complete after 35 hours. The resulting black liquid is cooled and then removed from the autoclave. The target compounds are precipitated by adding water. The solid fraction is separated by filtration. After drying, 42 g of product is obtained, consisting of eriodictyol (18.30 g), eriodictyol-7-O-glucoside (10.89 g), and eriocitrin (0.22 g).

[0087] The crude product (42 g) was dissolved in methanol (168 g) at room temperature. The solution was stirred and antisolvent crystallization was carried out by adding water (630 g) and precipitating eriodictyol (14.56 g), eriodictyol-7-O-glucoside (6.21 g), and eriocitrin (0.04 g). By varying the 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) were obtained.

[0088] [Example 4] Preparation of a flavoring composition from lemon peel extract Lemon peel extract (30 g) and citric acid (16.4 g) are dissolved in water / acetone (270 g). The mixture is charged into an autoclave. Hydrolysis begins after reaching a temperature of 120 °C and a pressure of 4 bar. The reaction is complete after 18 hours. The resulting black liquid is cooled and then removed from the autoclave. Secondary components are precipitated by adding water and separated by filtration. The target compounds are precipitated by adding water. The solid fraction is separated by filtration. After drying, a total of 11 g of product is obtained, comprising eriodictyol (7.21 g), eriodictyol-7-O-glucoside (0.40 g), and eriocitrin (0.03 g).

[0089] [Example 5] Preparation of flavoring compositions from lemon peel extracts by enzymatic hydrolysis A slightly acidified 20 g / L lemon peel extract solution was hydrolyzed in tap water with stirring at 40°C for 24 h using 25 mL / L of Vegazym P-CS (Erbsloeh, Geisenheim), a commercially available enzyme preparation exhibiting rhamnosidase and glucosidase activities. The product was extracted three times with 40% of the reaction volume of ethyl acetate by stirring for 10 min followed by phase separation via centrifugation at 17,000 x g for 20 min. The combined organic phase was washed twice with 40% of the reaction volume of tap water and then dried under vacuum. The hydrolysis product obtained after 24 h contained 0.01 wt% eriocitrin, 12.8 wt% eriodictyol-7-O-glucoside, and 69.5 wt% eriodictyol.

[0090] The crude extract was purified by precipitation. The crude extract was dissolved in ethanol at 40°C, and the target compounds were precipitated by adding water. After filtration, the product contained 0.01% by weight of eriocitrin, 3.90% by weight of eriodictyol-7-O-glucoside, and 76.24% by weight of eriodictyol.

[0091] [Example 6] Preparation of flavoring compositions from lemon peel extracts by hydrolysis with citric acid and enzymatic hydrolysis Lemon peel extract (300 g) and tartaric acid (39 g) are dissolved in water / acetone (2700 g). The mixture is charged into an autoclave. Hydrolysis begins after reaching a temperature of 120°C and a pressure of 5 bar. The reaction is complete after 35 hours. The resulting black liquid is removed from the autoclave after cooling.

[0092] The target compounds were precipitated by adding water. The solid material was obtained by filtration, and enzymatic hydrolysis was switched on using Vegazym P-CS at 50 ml / L at 50 °C for 24 hours. The target compounds were recovered by extraction and concentration with ethyl acetate. The extract contained 0.01 wt% eriocitrin, 3.4 wt% eriodictyol-7-O-glucoside, and 72.6 wt% eriodictyol.

[0093] [Example 7] Improving the taste of vegan patties Vegan patties were made containing the following ingredients: water, legume protein isolate, sunflower oil, legume protein concentrate, palm oil, methylcellulose, fiber, salt, starch, lactic acid, and sodium diacetate. The water, thickener, and starch are mixed with the water, the pH is adjusted, and then the protein, followed by the fiber and oil ingredients, are added. Finally, the taste-masking ingredients according to Table 4 are added. These ingredients are thoroughly mixed to form a dough into patties. The patties were baked in an oven at 200°C. After cooling, the patties were sliced ​​and the samples coded for blind tasting by a panel.

[0094] [Table 4]

[0095] The vegan pâté had a bitter, astringent taste with bready, roasty notes (Table 4, no. 1). Addition of the bitterness-masking compounds eriodictyol and homoeriodictyol, as described in U.S. Patent No. 5,629,499, improved the taste profile, but homoeriodictyol reduced the bitterness even more than eriodictyol. However, the flavoring composition of the present invention from lemon peel extract showed the best taste-improving and bitterness-masking properties.

[0096] [Example 8] Flavoring compositions The mixture can be compared with additional taste-modulating compounds to impart a taste-modulating sensory effect. Naringenin and hesperetin are used as examples, and the results are shown in Table 5. A masking mixture comprising 3 parts hesperetin, 2 parts naringenin, and 2 parts of the present citrus hydrolysate (55 wt.% ED, 11.1 wt.% EDMG, 1.5 wt.% EC) was tested at a 50 mg / kg dose against naringenin, hesperetin, and homoeriodictyol (Nos. 1-3, Table 5). All of these compounds and the mixture were dissolved in water with 500 mg / kg of caffeine added as a bittering agent. Panelists were asked to rate the bitterness intensity of each sample in a pair on a scale of 1 to 100. The results show that the masking mixture significantly (t-test = 0.0039) masked the bitterness of the caffeine solution (No. 4, Table 5). The taste-masking activity was higher than that of homoeriodictyol (-6.1% reduction in Direct Comparison Test No. 3, Table 5), higher than that of hesperetin (-16.4% reduction in Direct Comparison Test No. 2, Table 5), and highest in a direct comparison to naringenin (-21.7% reduction in Test No. 1, Table 5). This demonstrates that naringenin and hesperetin alone are not effective bitter-masking compounds, but when formulated with the citrus hydrolysate of the present invention, they exhibit significant bitter-masking activity, and that the bitter-masking activity is at least higher than that of homoeriodictyol, even though the masking mixture only contains approximately 5 mg / kg of eriodictyol. Said mixture can be obtained by mixing the citrus hydrolysate according to the invention with hydrolysates from orange (yielding hesperetin), grapefruit or bergamot (yielding naringenin) or bitter orange and lime, among other citrus fruits.

[0097] [Table 5]

[0098] [Example 9] Improving the taste of protein foods Protein-rich foods were prepared by adding 0.5 g of agar agar (CERO Agar Agar Gelidium Type 8952) to 100 g of warm water, stirring at 750 rpm at 55°C, and finally adding 10% by weight of pea (Preparation 1) and soy protein (Preparation 2) concentrates. The mixtures were homogenized and finally filled into cups. The samples were thickened by cooling to 8°C for 20 minutes to form a homogeneous and stable matrix. Each sample was tasted pairwise against a sample containing the inventive composition, i.e., lemon peel hydrolysate according to sample no. 4 from Table 3. These samples were coded and tasted by five flavorists. The intensity of the sensory attributes was determined on a scale of 0 to 10.

[0099] [Table 6]

[0100] [Table 7]

[0101] The sensory data show that off-tastes such as bitter, astringent, sour and pea pod taste can be reduced by adding 100 mg / kg lemon peel hydrolysate according to sample no. 4 from Table 3.

Claims

1. A flavoring composition for improving taste and / or masking bitterness, comprising eriocitrin, eriodictyol-7-O-glucoside, and eriodictyol, Eriodictyol is contained in an amount of 5% to 55% by weight, said amount being dependent on the dry weight of said flavoring composition; With or without neoeriocitrin, Flavoring compositions.

2. 2. The flavoring composition of claim 1, wherein the flavoring composition is obtained from a natural extract of at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involuculata, Balanophora tobiracora, Chrysanthemum morifolium, Chrysantherum indicum, Citrus species, Dracocephalum rupestre, Viscum liquidumvaricorum, Viscum coloratum, Viscum alticulatum, Lucianthus japonica, Lophophytum leandrii, Ersholtzia bodinieri, Umbellaria californica, Lycops europaeus, Buddleia parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica, and Impatiens glandulifera.

3. The composition may comprise the following additional flavoring substances: aliphatic flavoring substances, Flavoring ingredients, Juice concentrates, and Acetophenone, allyl caproate, α-ionone, β-ionone, anisaldehyde, anisyl acetate, anisyl formate, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, β-ionone, butyl butyrate, butyl caproate, butylidenephthalide, carvone, camphene, caryophyllene, cineole, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascone, decalactone, dihydro Coumarin, dimethyl anthranilate, dodecalactone, ethoxyethyl acetate, ethyl butyrate, ethyl butyrate, ethyl caprate, ethyl caproate, ethyl crotonate, ethyl furaneol, ethyl guaiacol, ethyl isobutyrate, ethyl isovalerate, ethyl lactate, ethyl methyl butyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptylate, 4-(p-hydroxyphenyl)-2-butanone, γ-decalactone, geraniol, geranyl acetate, grapefruit Thualdehyde, methyl dihydrojasmonate, heliotropinone, 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, methyl butanol, methyl butyric acid, 2-methylbutyl acetate, methyl caproate, methyl cinnamate,5-methylfurfural, 3,2,2-methylcyclopentenolone, 6,5,2-methylheptenone, methyl dihydrojasmonate, methyl jasmonate, 2-methylmethylbutyrate, 2-methyl-2-pentenoic 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, δ-octalactone, γ-octalactone ethanol, 2-octanol, 3-octanol, 1,3-octenol, 1-octyl acetate, 3-octyl acetate, palmitic acid, paraldehyde, phellandrene, pentanedione, phenethyl acetate, phenethyl alcohol, phenethyl isovalerate, piperonal, propionaldehyde, propyl butyrate, pulegone, pulegol, sinensal, sulfurol, terpinene, terpineol, terpinolene, 8,3-s-thiomenthanone, 4,4,2-thiomethylpentanone, thymol, δ-undecalactone, γ-undecyl Calactone, valencene, valeric acid, vanillin, acetoin, ethyl vanillin, ethyl vanillin isobutyrate (= 3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3(2H)-furanone, homofuranol (= 2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol, coumarin, γ-lactone, δ-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, 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)disulfide, furfuryl mercaptan, 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 pyrazine, 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, cinnamyl alcohol, methyl salicylate, isopulegol, and stereoisomers, enantiomers, diastereomers, cis / trans isomers or epimers of these substances, 3. The flavoring composition according to claim 1, comprising at least one selected from the group consisting of:

4. The composition comprises:

3. The flavoring composition according to claim 1, which contains at least one sweet substance selected from the group consisting of natural sweeteners and synthetic sweeteners.

5. 1. A method for masking and / or reducing the bitter taste in / of a preparation, comprising: a) providing at least one preparation selected from the group consisting of a food, a beverage and an oral hygiene product; b) providing a flavoring composition according to claim 1; c) contacting and mixing the preparation provided in step a) with the flavoring composition provided in step b); d) obtaining a preparation with improved taste; or consisting of steps a) to d).

6. (i) providing a natural extract from at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involuculata, Balanophora tobiracora, Chrysanthemum morifolium, Chrysantherum indicum, Citrus species, Dracocephalum rupestre, Viscum liquidumvaricorum, Viscum coloratum, Viscum alticulatum, Lucianthus japonica, Lophophytum leandrii, Ersholtzia bodinieri, Umbellaria californica, Lycops europaeus, Buddleia parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichurn niveum, 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 to 60°C; (v) obtaining a flavoring composition according to claim 1; 2. A method for producing a flavoring composition according to claim 1, comprising or consisting of steps (i) to (v).

7. (i) providing a natural extract from at least one plant selected from the group consisting of Gleditsia caspia, Balanophora involuculata, Balanophora tobiracora, Chrysanthemum morifolium, Chrysantherum indicum, Citrus species, Dracocephalum rupestre, Viscum liquidumvaricorum, Viscum coloratum, Viscum alticulatum, Lucianthus japonica, Lophophytum leandrii, Ersholtzia bodinieri, Umbellaria californica, Lycops europaeus, Buddleia parviflora, Eminium spiculatum, Coreopsis tinctoria, Cyclotrichurn niveum, Arnica longifolia, Caryopteris incana, Mentha aquatica, and Impatiens glandulifera; (ii) providing at least one naturally occurring non-volatile organic acid; (iii) mixing the natural extract provided in step (i) with the at least one natural non-volatile organic acid provided in step ii); (iv) incubating the mixture obtained in step iii) at a temperature in the range of 100-160°C; (v) obtaining a flavoring composition according to claim 1; 2. A method for producing a flavoring composition according to claim 1, comprising or consisting of steps (i) to (v).

8. 8. The method of claim 6 or 7, wherein the natural extract provided in step (i) is a citrus extract.

9. 7. The method of claim 6, wherein the hydrolase provided in step (ii) is a glucosidase or a rhamnosidase.

10. 8. The method of claim 5, wherein the provided flavoring composition is obtained or obtainable by the method of claim 6 or 7.

Images