EP1784088A1 - Amides d'acide hydroxybenzoique et leur utilisation pour masquer un gout amer - Google Patents

Amides d'acide hydroxybenzoique et leur utilisation pour masquer un gout amer

Info

Publication number
EP1784088A1
EP1784088A1 EP05777921A EP05777921A EP1784088A1 EP 1784088 A1 EP1784088 A1 EP 1784088A1 EP 05777921 A EP05777921 A EP 05777921A EP 05777921 A EP05777921 A EP 05777921A EP 1784088 A1 EP1784088 A1 EP 1784088A1
Authority
EP
European Patent Office
Prior art keywords
hydroxy
group
unpleasant
preparation
amide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05777921A
Other languages
German (de)
English (en)
Inventor
Jakob Ley
Heinz-Jürgen BERTRAM
Günter Kindel
Gerhard Krammer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Symrise AG filed Critical Symrise AG
Publication of EP1784088A1 publication Critical patent/EP1784088A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/48—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms

Definitions

  • the invention relates to the use of certain hydroxybenzoic acid amides, their salts and mixtures thereof for masking or reducing unpleasant taste impressions, in particular bitter, astringent and / or metallic taste impressions and / or enhancing the sweet taste impression of a sweet substance. Certain of these hydroxybenzoic acid amides are new. Furthermore, the invention relates to certain preparations which contain an effective content of the Hydroxybenzoeklareamiden, their salts or mixtures thereof. Finally, the invention relates to processes for the preparation according to the invention to be used Hydroxybenzoeklaamide.
  • Food or stimulants often contain various bitter substances that are both desirable and characteristic in moderation (eg caffeine in tea or coffee, quinine in so-called bitter lemon drinks, hop extracts in beer), on the other hand, the value can also greatly reduce (eg Flavonoid glycosides and limonoids in citrus juices, bitter aftertaste of many artificial sweeteners such as aspartame or saccharin, hydrophobic amino acids and / or peptides in cheese).
  • bitter substances eg caffeine in tea or coffee, quinine in so-called bitter lemon drinks, hop extracts in beer
  • the value can also greatly reduce (eg Flavonoid glycosides and limonoids in citrus juices, bitter aftertaste of many artificial sweeteners such as aspartame or saccharin, hydrophobic amino acids and / or peptides in cheese).
  • a subsequent treatment is often necessary, for example, extractive as in the decaffeination of tea or coffee, or enzymatically, for example, treatment of orange juice with a glycosidase to destroy the bitter naringin or use of special peptidases in the maturation of cheese.
  • This treatment is stressful for the product, generates waste and also causes, for example, solvent residues and other residues (enzymes) in the products.
  • bitter taste is particularly important.
  • Many pharmaceutical active ingredients for example aspirin, salicin, paracetamol, ambroxol or quinine, to mention only a very small selection for clarity, have a pronounced bitter, astringent and / or metallic taste and / or taste.
  • 2,4-Dihydroxybenzoic acid potassium salt is described in US 5,643,941 (table column 3, line 18) as a masking agent for the bitter taste of potassium chloride, but can not suppress the taste of caffeine, for example.
  • GB 2,380,936 the suppression of the taste of bitter pharmaceuticals with ginger extracts is achieved.
  • the strong flavor impression and / or the sharpness of ginger extracts or active ingredients thereof often found therein is not suitable for a variety of applications.
  • Neohesperidin dihydrochalcone also shows a bitter-reducing effect, but is above all a sweetener (see Manufacturing Chemist 2000, July issue, pp 16-17), which also has a disturbing effect in non-sweet applications.
  • the sodium salts sodium chloride, sodium citrate, sodium acetate and sodium lactate show a bitter-masking effect against many bitter substances (eg Nature, 1997, Vol. 387, p. 563);
  • the intake of larger amounts of sodium ions can lead to cardiovascular diseases.
  • a significant bitter-masking effect also occurs disadvantageously only at relatively high sodium concentrations (from about 0.1 M), which, for example, a generally unacceptably high proportion of about 0.6 wt .-% NaCl in the final application corresponds (see RSJ Keast, PAS Breslin and GK Beauchamp, Chimia 2001, 55 (5), 441-447)
  • polyglutamic acid is described as a bitterness-masking agent; while relatively high concentrations in the range of 1 wt .-% are needed.
  • a lipoprotein consisting of ⁇ -lactoglobulin and phosphatidic acid also shows a bitter-masking effect (EP-A 635 218).
  • EP-A 635 218 A lipoprotein consisting of ⁇ -lactoglobulin and phosphatidic acid also shows a bitter-masking effect (EP-A 635 218).
  • such polymers are difficult to characterize and standardize and show a pronounced soapy off-taste.
  • the flavone glycoside neodiosmin [5,7-dihydroxy-2- (4-methoxy-3-hydroxyphenyl) -7-O-neohesperidosyl-chromium-2-en-4-one] also shows a bitter-masking effect (US-A 4,154,862 ), but is characterized by a disaccharide radical, which makes the preparation or isolation and applicability of the substance very difficult.
  • R 1 to R 5 independently of one another denote hydrogen, hydroxyl, methoxy or ethoxy, with the proviso that at least one of the radicals R 1 to R 5 is hydroxyl,
  • R 6 is hydrogen, methyl or ethyl
  • n 1 or 2
  • R 1 , R 3 and R 5 are independently hydrogen or hydroxy, provided that at least one of said radicals is hydroxy,
  • R 2 and R 4 are hydrogen
  • R 6 is hydrogen, methyl or ethyl
  • n 1 or 2
  • R 1 is hydroxy
  • R 3 and R 5 are independently hydrogen or hydroxy
  • R 2 and R 4 are hydrogen
  • R 6 is hydrogen, methyl or ethyl
  • n 1 or 2
  • R 6 is preferably methyl or ethyl and n is preferably 1.
  • Unpleasant tasting substances according to the invention are:
  • the aforementioned unpleasant-tasting substances may have other, usually not unpleasant taste and / or odor qualities.
  • taste qualities which are not unpleasant for the purposes of the present invention, e.g. To call impressions spicy, umami, sweet, salty, sour, pungent, cooling, warming, burning or tingling.
  • Substances that are bitter, astringent, sticky, dusty, dry, floury, rancid or metallic for example: xanthine alkaloids xanthines (caffeine, theobromine, theophylline), alkaloids (quinine, brucine, strychnine, nicotine), phenolic glycosides (eg salicin, Arbutin), flavonoid glycosides (eg hesperidin, naringin), chalcone or chalcone glycosides, hydrolyzable tannins (gallus o of the esters of esters of carbohydrates, eg pentagalloylglucose), nonhydrolyzable tannins (possibly galloylated catechins or epicatechins and their oligomers, for example proanthocyanidins or procyanidins, thearubigenin), flavones (eg quercetin, taxifolin, myricetin), other polyphenols ( ⁇ -oryzanol, caffe
  • Substances that have a bitter, astringent, poppy, dusty, dry, floury, rancid or metallic aftertaste may belong, for example, to the group of sweeteners or sugar substitutes.
  • sweeteners or sugar substitutes examples include: aspartame, neotame, superaspartame, saccharin, sucralose, tagatose, monellin, steviosides, thaumatin, miraculin, glycyrrhizin, glycyrrhetinic acid or its derivatives, cyclamate or the pharmaceutically acceptable salts of the aforementioned compounds.
  • Sweet-tasting substances may, for example, be sweet-tasting carbohydrates (e.g., sucrose, trehalose, lactose,
  • salts of a hydroxybenzoic acid amide of the formula (I) to be used according to the invention where the above definitions still apply with regard to the preferred meanings of the radicals and variables
  • one, several or all hydroxyl groups of the hydroxybenzoic acid amide are deprotonated.
  • countercations which are preferably selected from the group consisting of: simply positively charged cations of the first main and subgroup, ammonium ions, trialkylammonium, twice positively charged cations of the second main and subgroup and triply positively charged Cations of the 3rd main and subgroup, and their mixtures.
  • the number of hydroxy groups in the underlying hydroxybenzoic acid amide is critical to the maximum degree of deprotonation and thus also to the amount of countercation present. For example, if only a total of two hydroxy groups are present in the underlying hydroxybenzoamide, complete deprotonation of the hydroxy groups will result in a doubly negatively charged amide anion such that a corresponding number of positive charges must be provided by the counter cation (s).
  • Particularly preferred cations are Na + , K + , NH 4 + , Ca 2+ , Mg 2+ , Al 3+ and Zn 2+ .
  • New compounds are the compounds (1) - (8).
  • WO 2004/026292 A1 discloses the compound N- (4-hydroxy-3-methoxybenzyl) -2-hydroxy-4,6-dimethoxybenzamide, but its use as a taste correcting agent is not described.
  • Example 9 the 2,4-dihydroxybenzoic acid ⁇ / - (3-hydroxy-4-methoxybenzyl) amide (Example 9) was prepared in own investigations and investigated for the presence of a bitter-masking effect (Application Example 1). No statistically significant change in the bitter impression was found.
  • the hydroxybenzoic acid amides to be used according to the invention even in very low concentrations, have the unpleasant taste impression, in particular the bitter taste impression of a multiplicity of substances, in particular of methylxanthines such as caffeine, alkaloids, such as quinine, flavonoids, for example
  • methylxanthines such as caffeine, alkaloids, such as quinine, flavonoids, for example
  • naringin phenols such as salicin
  • inorganic salts such as potassium chloride or magnesium sulfate
  • pharmaceutical agents such as Denatoniumbenzoat or ß-lactam antibiotics can reduce or even completely suppress, and it is particularly advantageous that the present invention to use hydroxybenzoic have almost no taste and the other , usually does not adversely affect unpleasant taste qualities.
  • the hydroxybenzoic acid amides to be used according to the invention simultaneously have a sweetness-boosting action and are therefore also able to serve excellently as taste correction by simultaneously reducing the bitterness and raising the sweetness taste.
  • the hydroxybenzoamide to be used according to the invention, the salt or the mixture are used for administration in the region of the head in an oral or pharmaceutical preparation or cosmetic preparation used for nutrition, oral hygiene or pleasure.
  • Preparations according to the invention serve (a) the nutrition, (b) the enjoyment or (c) the oral care or are (d) oral pharmaceutical preparations or are (e) cosmetic preparations for application in the region of the head.
  • Preparations and cosmetic preparations for application in the region of the head which are used according to the invention for nutrition, oral hygiene or pleasure preferably comprise 0.000001% by weight to 95% by weight, based on the total weight of the preparation of a hydroxybenzoic acid amide, salt or mixture.
  • An oral pharmaceutical preparation according to the invention preferably comprises 0.000001% by weight to 10% by weight, based on the total weight of the preparation, of a composition according to the invention Hydroxybenzoeklamids, salt or mixture and at least one unpleasant tasting substance (see the definition above).
  • preparations according to the invention which comprise at least one unpleasant tasting substance, the amount of the unpleasant tasting substance being sufficient to be perceived as an unpleasant taste in a comparison preparation which does not comprise a hydroxybenzoamide according to the invention, salt or mixture, but otherwise identically composed , and the amount of the hydroxybenzoic acid amide, salt or mixture according to the invention in the preparation is sufficient to mask the unpleasant taste impression of the unpleasant tasting substance or to reduce it in comparison with the comparison preparation.
  • Preparations according to the invention may be in the form of a semi-finished product, a fragrance, aroma or flavoring composition or a seasoning mixture.
  • nutrition or pleasure-serving preparations are, for example, baked goods (eg bread, dry biscuits, cakes, other pastries), confectionery (for example chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages.
  • baked goods eg bread, dry biscuits, cakes, other pastries
  • confectionery for example chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum
  • alcoholic or non-alcoholic beverages are, for example, baked goods (eg bread, dry biscuits, cakes, other pastries), confectionery (for example chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages.
  • alcoholic beverages eg coffee, tea, wine, wine-based drinks, beer, beer-based drinks, liqueurs, brandies, brandies, fruit-based sodas, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations
  • instant drinks eg instant drinks
  • meat products eg ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or salted meat products
  • eggs or egg products dry egg, egg white, egg yolk
  • cereal products eg breakfast cereals, Muesli bars, pre-cooked finished rice products
  • dairy products eg milk drinks, milk ice cream, yoghurt rt, kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partially or fully hydrolyzed milk protein-containing products
  • Products made from soy protein or other soybean fractions eg soy milk and products made therefrom, soy lecithin-containing preparations, fermented products
  • the preparations according to the invention can also serve as semi-finished goods for the production of further preparations serving for nutrition or enjoyment.
  • the preparations according to the invention can also be used in the form of capsules, tablets (non-coated and coated tablets, eg gastric juice-resistant coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as Pastes or other swallowable or chewable preparations as dietary supplements.
  • the oral care preparations according to the invention are in particular oral and / or dental care such as toothpastes, tooth gums, tooth powder, mouthwash, chewing gum and other oral care products.
  • Oral pharmaceutical preparations according to the invention are preparations which are e.g. in the form of capsules, tablets (uncoated and coated tablets, for example enteric coatings), dragées,
  • Granules, pellets, solid mixtures, dispersions in liquid phases as
  • Emulsions as powders, as solutions, as pastes or as other swallowable or chewable preparations and as a prescription, pharmacy or other drugs or as
  • Cosmetic preparations for application in the region of the head are in particular those which contain an unpleasant-tasting substance and can even come into contact with the oral cavity when properly applied to the skin, ie, for example, as already mentioned, cosmetic preparations for application in the region of the head Soaps, other cleansers or conditioners for the face, face creams or lotions or ointments, sunscreens, beard wipes or shampoos, shaving creams, soaps or gels, lipsticks or other lip cosmetics or lip balms.
  • compositions for nutrition, oral hygiene or pleasure or oral pharmaceutical preparations or cosmetic preparations in the region of the head can be used in amounts of from 5 to 99.999999% by weight, preferably 10 to 80 wt .-%, based on the total weight of the preparation, be contained.
  • the preparations may comprise water in an amount of up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
  • preparations according to the invention containing one or more of the hydroxybenzoic acid amides or their salts or mixtures to be used according to the invention are prepared according to a preferred embodiment by using the hydroxybenzoic acid amides or their salts or mixtures according to the invention as substances, as a solution or in the form of a Mixture with a solid or liquid carrier in a diet, oral care or pleasure or oral pharmaceutical base preparation are incorporated.
  • preparations according to the invention which are present as a solution can also be converted into a solid preparation by spray drying.
  • preparations to be used according to the invention are used according to the invention
  • Hydroxybenzoeklareamide or their salts or mixtures and optionally other constituents of the preparation according to the invention also previously in emulsions, in liposomes, for example starting from phosphatidylcholine, in microspheres, in nanospheres or else in capsules, granules or extrudates from a matrix suitable for foods and luxury foods, for example from starch, starch derivatives, cellulose or cellulose derivatives (eg hydroxypropylcellulose), others Polysaccharides (eg alginate), natural fats, natural waxes (eg beeswax, carnauba wax) or from proteins, eg gelatin, incorporated.
  • the hydroxybenzoic acid amides or their salts or mixtures are previously complexed with one or more suitable complexing agents, for example cyclic polysaccharides such as cyclofructans, cyclodextrins or cyclodextrin derivatives, preferably ⁇ -cyclodextrin or ⁇ -cyclodextrin, and used in this complexed form.
  • suitable complexing agents for example cyclic polysaccharides such as cyclofructans, cyclodextrins or cyclodextrin derivatives, preferably ⁇ -cyclodextrin or ⁇ -cyclodextrin, and used in this complexed form.
  • a preparation according to the invention in which the matrix is chosen such that the hydroxybenzoic acid amides are released from the matrix with a delay, so that a long-lasting effect is obtained.
  • auxiliaries and additives for foods or luxury foods for example water, mixtures of fresh or processed, vegetable or animal raw materials or raw materials (eg raw, roasted , dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or their mixtures), digestible or non-digestible carbohydrates (eg sucrose, maltose, fructose , Glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose), sugar alcohols (eg sorbitol), natural or hydrogenated fats (eg tallow, lard, palm fat, coconut fat, hydrogenated vegetable fat), oils (eg sunflower oil, peanut oil, corn oil, olive oil , Fish oil, soybean oil, sesame oil), fatty acids or their salts (eg potassium stearate),
  • vegetable or animal raw materials or raw materials eg raw, roasted , dried, fermented,
  • Dentifrices (as a base for oral care preparations) containing the hydroxybenzoic acid amides, their salts or mixtures to be used in accordance with the invention generally comprise an abrasive system (grinding or polishing agents), e.g. Silicic acids, calcium carbonates, calcium phosphates, aluminum oxides and / or hydroxyl apatites, surface-active substances such as e.g. sodium lauryl sulfate,
  • an abrasive system grinding or polishing agents
  • Silicic acids e.g. Silicic acids, calcium carbonates, calcium phosphates, aluminum oxides and / or hydroxyl apatites, surface-active substances such as e.g. sodium lauryl sulfate,
  • Natriumlaur ⁇ lsarcosinat and / or Cocamidopropylbetain humectants such as glycerol and / or sorbitol
  • thickeners such as carboxymethylcellulose, polyethylene glycols, carrageenan and / or Laponite ®
  • sweeteners such as saccharin
  • flavoring agents for unpleasant taste sensations flavoring properties for more, as a rule not unpleasant taste impressions
  • taste modulating substances eg Inositol phosphate, nucleotides such as guanosine monophosphate
  • Adenosine monophosphate or other substances such as monosodium glutamate or 2-phenoxypropionic acid
  • cooling agents e.g. Menthol or menthol derivatives
  • stabilizers and active agents e.g. Sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc nitrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetylpyridinium chloride,
  • Chewing gums (as another example of oral care preparations) containing hydroxybenzoic acid amides to be used according to the invention, their salts or mixtures generally comprise a chewing gum base, i. chewing gum that becomes plastic during chewing, sugars of various types, sugar substitutes, sweeteners, sugar alcohols,
  • Flavoring agents for unpleasant taste sensations for other, generally not unpleasant, taste modifiers (e.g., inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, flavors and stabilizers or odorants.
  • inositol phosphate nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid
  • humectants e.g., humectants, thickeners, emulsifiers, flavors and stabilizers or odorants.
  • constituents for oral pharmaceutical preparations it is generally possible to use all other active substances, basic substances, adjuvants and additives for oral pharmaceutical preparations.
  • unpleasant-tasting orally formable pharmaceutical active substances can also be used as active ingredients.
  • the active substances, basic substances, auxiliaries and additives can be converted into the oral administration forms in a manner known per se. This is done regularly using inert, non-toxic, pharmaceutically suitable excipients.
  • excipients eg microcrystalline cellulose
  • solvents eg liquid polyethylene glycols
  • emulsifiers eg sodium dodecyl sulfate
  • dispersants eg, polyvinylpyrrolidone
  • synthetic and natural biopolymers eg, albumin
  • stabilizers eg, antioxidants such as ascorbic acid
  • dyes eg, inorganic pigments such as iron oxides
  • odorants eg, inorganic pigments such as iron oxides
  • the preparations according to the invention may preferably also contain an aroma composition in order to round off and refine the taste and / or smell of the preparation.
  • Suitable flavor compositions contain e.g. synthetic, natural or nature-identical flavorings, fragrances and flavorings as well as suitable excipients and carriers. It is considered to be particularly advantageous that a bitter or metallic taste impression emanating from aroma or fragrance substances contained in the preparations according to the invention can be masked or reduced and thus the entire aroma or taste profile is improved.
  • Preparations according to the invention which are present as semi-finished goods, can serve to mask or reduce the unpleasant taste impression of finished product preparations which are produced using the semi-finished product preparation.
  • Preparations according to the invention which serve as semi-finished goods generally contain from 0.0001% by weight to 95% by weight, preferably from 0.001 to 80% by weight, but in particular from 0.01% by weight to 50% by weight , based on the total weight of the preparation, of hydroxybenzoic acid amides to be used according to the invention, their salts or mixtures thereof.
  • Preparations according to the invention, which are present as semi-finished goods can serve to mask or reduce the unpleasant taste impression of finished product preparations which are produced using the semi-finished product preparation.
  • the hydroxybenzoic acid amides according to the invention in combination with at least one further substance used for changing, masking or reducing the unpleasant taste impression of an unpleasant tasting substance.
  • at least one further substance used for changing, masking or reducing the unpleasant taste impression of an unpleasant tasting substance in this way, a particularly effective masking can be achieved.
  • nucleotides e.g.
  • hydroxyflavanones e.g., eriodictyol, homoeriodictyol or their sodium salts according to EP 1 258 200
  • amino acids or mixtures of whey proteins with lecithins e.g., eriodictyol, homoeriodictyol or their sodium salts according to EP 1 258 200.
  • R 1 to R 5 have the meaning given above (preferably one marked as preferred) and
  • X is a hydroxyl group, alkyloxy or alkenyloxy group, an (optionally substituted) aryloxy group, an N-heterocyclyloxy group, an N-heterocyclyl group, a halogen atom, an (optionally substituted) sulfur atom, a group -ON having a (multi) substituted nitrogen atom, or a group RC (O) -O-, wherein R represents an alkyl or alkenyl radical, preferably a halogen atom, a nitro-substituted aryloxy group, an aromatic sulphonyloxy group, an N-heterocyclyl group or a cyclic (optionally substituted) hydroxylamine or other carboxyl activating group, especially preferably chlorine, bromine, p- or o-nitrophenyloxy group, p-toluenesulfonyloxy group, N-imidazolyl group, N-benzotriazolyl group,
  • R 6 and n have the meanings given above (preferably one marked as preferred),
  • Trihydroxybenzoic acid or its protected derivatives but preferably 2-hydroxy, 4-hydroxy, 2,4-dihydroxy or 2,4,6-trihydroxybenzoic acid or their protected derivatives may be used
  • amines of the formula (III) it is possible to use 4-hydroxy-3-methoxybenzylamine, 4-hydroxy-3-ethoxybenzylamine, 2- (4-hydroxy-3-methoxyphenyl) ethylamine or 3,4-dihydroxybenzylamine. Their ammonium salts can also be used.
  • Suitable acid scavengers or bases may be alkali metal hydroxides (eg NaOH), alkali metal carbonates (eg Na 2 CO 3 or NaHCO 3 ), alkaline earth metal hydroxides (eg Mg (OH) 2 , Ba (OH) 2 ), alkaline earth metal oxides (eg CaO) or alkaline earth metal carbonates (eg CaCO 3 ), Ammonia, aliphatic amines (eg triethylamine or diisopropylamine) or heterocyclic amines (eg pyridine or 4- (N, N-dimethylamino) pyridine) or basic inorganic or organic ion exchangers.
  • alkali metal hydroxides eg NaOH
  • alkali metal carbonates eg Na 2 CO 3 or NaHCO 3
  • alkaline earth metal hydroxides eg Mg (OH) 2 , Ba (OH) 2
  • alkaline earth metal oxides eg CaO
  • a dehydrating system may be used, for example, an activated molecular sieve, a concentrated acid or a carbodiimide.
  • the reaction in the presence of carbodiimides is advantageously carried out in a solvent or solvent mixture.
  • the reactions are preferably carried out with nonpolar carbodiimides, for example N, N'-dicyclohexylcarbodiimide, in ethers, in particular diethyl ether, dioxanes, tetrahydrofuran or tert-butyl methyl ether or in esters, for example ethyl acetate, or in ketones, for example acetone
  • solvents or solvent mixtures are: water, lower alcohols (ethanol, methanol), acetone, 1,4-dioxane, tetrahydrofuran, tert-butyl methyl ether, aliphatic esters of aliphatic alcohols (such as ethyl acetate), chlorine-containing solvents (eg chloroform) and aromatic Solvents (eg benzene, toluene).
  • the bitterness of a caffeine or salicin solution containing 500 ppm and a sample containing 500 ppm caffeine or salicin and an alternate amount of the exemplary compound was determined by a panel of experts (rating 0). not bitter] to 10 [extremely bitter]).
  • the evaluation was carried out as a calculation of the reduction (in%) of the bitterness impression from the average values of the assessments of the caffeine or salicin solution or of the solutions containing caffeine or salicin and exemplary compound.
  • 2,4-Dihydroxybenzoic acid (2,4-DHB) was used as a comparison from US 5,643,941.
  • Application example 2 Spray-dried preparation as semi-finished product for the flavoring of finished goods
  • Example 1 The drinking water is placed in a container and the maltodextrin and gum arabic dissolved therein. Subsequently, the 2,4-dihydroxybenzoic acid ⁇ / - (4-hydroxy-3-methoxybenzyl) amide (Example 1) is emulsified with a Turrax in the carrier solution. The temperature of the spray solution should not exceed 30 ° C. The mixture is then spray-dried (nominal temperature input: 185-195 ° C, target temperature output: 70-75 ° C). The spray-dried semi-finished product contains about 18-22% of the active ingredient from example 1.
  • Application example 3 Black tea preparation
  • tea and semi-finished goods are mixed and packaged in teabags made of filter paper.
  • a tea bag is poured into 100 - 250 ml of boiling water and left for 2 - 5 min.
  • tea and semi-finished goods are mixed and packaged in teabags made of filter paper.
  • a tea bag is poured into 100 - 250 ml of boiling water and left for 2 - 5 min.
  • ⁇ -Aminobutyric acid was pre-dissolved in water and 2,4-dihydroxybenzoic acid- ⁇ / - (4-hydroxy-3-methoxybenzyl) amide from Example 1 ethanol and added to a soybean milk from a local supermarket. The mixture was stirred together with the Museumaroma in the beaker.
  • Parts A to D are mixed and kneaded intensively.
  • the raw mass may e.g. be processed in the form of thin strips to ready-to-eat chewing gum.
  • Parts A and B are each premixed and stirred well together under vacuum at 25-30 ° C for 30 minutes.
  • Part C is premixed and added to A and B; D is added and the mixture under vacuum at 25 - 30 0 C for 30 min stirred well. After relaxation, the toothpaste is ready and can be bottled.
  • the sweetness of a 5% sucrose containing low-fat (0.1%) commercial yoghurt (Optiwell) and a sample containing 5% ppm sucrose and a quantity of the exemplified compound was determined by a panel of experts (classification 0 [not cute] to 10 [extremely sweet]). Evaluation was done by calculating the enhancement (in%) of the sweetness impression from the average values of the evaluations of the yoghurt containing sucrose or the yoghurt containing exemplary compound.
  • Yoghurt containing example 1 was preferred and, in addition to the descriptors, increased fullness, less acidic, soft, creamy.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Seasonings (AREA)

Abstract

L'invention concerne des amides d'acide hydroxybenzoïque de la formule (I) où R<sup
EP05777921A 2004-08-27 2005-08-02 Amides d'acide hydroxybenzoique et leur utilisation pour masquer un gout amer Withdrawn EP1784088A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004041496A DE102004041496A1 (de) 2004-08-27 2004-08-27 Hydroxybenzoesäureamide und deren Verwendung zur Maskierung von bitterem Geschmack
PCT/EP2005/053764 WO2006024587A1 (fr) 2004-08-27 2005-08-02 Amides d'acide hydroxybenzoique et leur utilisation pour masquer un gout amer

Publications (1)

Publication Number Publication Date
EP1784088A1 true EP1784088A1 (fr) 2007-05-16

Family

ID=35058929

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05777921A Withdrawn EP1784088A1 (fr) 2004-08-27 2005-08-02 Amides d'acide hydroxybenzoique et leur utilisation pour masquer un gout amer

Country Status (4)

Country Link
US (1) US20080214675A1 (fr)
EP (1) EP1784088A1 (fr)
DE (1) DE102004041496A1 (fr)
WO (1) WO2006024587A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017186298A1 (fr) 2016-04-28 2017-11-02 Symrise Ag Dérivés de dihydrochalcone influençant des états inflammatoires
CN107667088A (zh) * 2015-03-31 2018-02-06 株式会社爱茉莉太平洋 新型苯甲酸酰胺化合物

Families Citing this family (86)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006106023A1 (fr) * 2005-04-04 2006-10-12 Symrise Gmbh & Co. Kg Hydroxydeoxybenzoines permettant de masquer un gout amer
ITMI20050674A1 (it) * 2005-04-15 2006-10-16 Univ Degli Studi Milano Uso di derivati ammidici come agenti modificatori del gusto composizioni aromatizzanti e prodotti che li contengono
US20080227866A1 (en) * 2005-07-05 2008-09-18 Symrise Gmbh & Co. Kg Hydroxyphenylalkadiones and Their Use for Masking Bitter Taste and/or for Intensifying Sweet Taste
EP2368442B1 (fr) 2005-07-27 2014-12-17 Symrise AG Utilisation d'hespérétine pour améliorer le goût sucré
US8778987B2 (en) 2007-03-13 2014-07-15 Symrise Ag Use of 4-hydroxychalcone derivatives for masking an unpleasant taste
EP1977655B1 (fr) 2007-03-29 2011-05-18 Symrise AG Compositions d'aromes d'alcamides comprenant de l'hespérétine et/ou des 4-hydroxydihydrochalcones et leurs sels destinées à renforcer les impressions sensorielles sucrées
EP1989944B1 (fr) 2007-05-08 2010-06-02 Symrise GmbH & Co. KG Acide cyclopropane carboxylique (3-méthyle-cyclohexyl)-amide substitué en tant qu'aromates
US8709521B2 (en) * 2007-05-22 2014-04-29 The Coca-Cola Company Sweetener compositions having enhanced sweetness and improved temporal and/or flavor profiles
DE502008002360D1 (de) * 2007-06-19 2011-03-03 Symrise Ag Aromakomposition zum Verringern oder Unterdrücken von unerwünschtem bitteren und adstringierenden Eindruck
EP2022503B1 (fr) 2007-08-07 2011-10-19 Symrise AG Extraits de vaccin encapsulés ayant une libération équilibrée dans l'estomac-intestin
EP2033688B1 (fr) 2007-08-20 2012-10-17 Symrise AG Dérivés d'acide oxalique et leur utilisation en tant que matières de refroidissement physiologiques
EP2064959B1 (fr) 2007-10-31 2012-07-25 Symrise AG Néomenthylamides aromatiques en tant qu'agents aromatisants
EP2058297B1 (fr) * 2007-11-08 2015-05-20 Symrise AG Procédé de production de profils polymériques organiques
WO2009085928A2 (fr) * 2007-12-20 2009-07-09 Motts Llp Boisson pour le sport et procédé de préparation de celle-ci
EP2135516B1 (fr) 2008-06-13 2012-08-15 Symrise AG Néo-dérivés de menthyle en tant qu'arômes artificiels
EP2135616B1 (fr) 2008-06-19 2016-05-04 Symrise AG Fruit d'airelle séché destiné à influencer l'état de l'intestin
US8043645B2 (en) 2008-07-09 2011-10-25 Starbucks Corporation Method of making beverages with enhanced flavors and aromas
ATE524978T1 (de) 2008-07-30 2011-10-15 Symrise Ag Zusammensetzung zur reduzierung des nacl-gehaltes in lebensmitteln
PL2323502T3 (pl) * 2008-09-05 2013-01-31 Unilever Nv Produkty żywnościowe zawierające flawan-3-ol
DE102008042421A1 (de) 2008-09-26 2010-04-01 Symrise Gmbh & Co. Kg Geranylaminderivate der Oxalsäure
DE102008044126A1 (de) 2008-11-27 2010-06-02 Symrise Gmbh & Co. Kg Aromastoffinklusionscellulose
EP2220945B1 (fr) 2008-12-11 2013-03-27 Symrise AG Composition aromatiques pour réduire ou supprimer les sensations indésirables de goût amer et astringent des édulcorants
EP2253226B1 (fr) 2009-05-15 2015-07-15 Leibniz-Institut für Pflanzenbiochemie (IPB) Utilisation de dérivés d'hydroxyflavane pour la modification du goût
DE102009027744A1 (de) 2009-07-15 2011-01-20 Deutsches Institut Für Ernährungsforschung Potsdam-Rehbrücke Prekursor-Verbindungen von Süßrezeptor-Antagonisten zur Prävention oder Behandlung von Krankheiten
EP2298084B1 (fr) 2009-08-28 2011-10-19 Symrise AG Produits réduits en saccharine, mélanges d'arômes correspondant et procédé de fabrication de tels produits
US10624372B2 (en) 2009-08-28 2020-04-21 Symrise Ag Reduced-sweetener products, flavoring mixtures for said reduced-sweetener products and process for the production of products of this type
EP2305742B1 (fr) 2009-10-01 2017-02-22 Symrise AG Particule coeur/enveloppe sphérique
US9446267B2 (en) 2009-10-06 2016-09-20 Symrise Ag Products comprising a flavoring agent composition
EP2186506B1 (fr) 2009-10-06 2015-09-30 Symrise AG Composition de nettoyage des dents contenant du menthol dotée d'une admission de l'amertume réduite
DE102009046126A1 (de) 2009-10-28 2011-05-12 Symrise Ag Oral konsumierbare Zubereitung umfassend Wurzelextrakt aus Mondia whitei
EP2340719B1 (fr) 2009-12-30 2014-02-19 Symrise AG Composition d'arome comportant de l'acide o-coumaromique pour réduire ou supprimer les impressions de mauvais goût des édulcorants
EP2359698B1 (fr) 2010-01-22 2013-12-04 Symrise AG Compositions avec système d'agent de surface comportant des saponines, et de la lécithine
EP2359702B1 (fr) 2010-01-22 2014-06-04 Symrise AG Agent de solubilisation pour solubiliser les polyphénols, flavonoïdes et/ou glucosides de diterpenoïde
PL2353403T3 (pl) 2010-02-01 2012-10-31 Symrise Ag Zastosowanie 1-(2,4-dihydroksy-fenylo)-3-(3-hydroksy-4-metoksy-fenylo)-propan-1-onu
AU2011215617B2 (en) * 2010-02-12 2016-01-28 Theocorp Holding Co., Llc Methods and compositions to improve mechanical resistance of teeth
AU2011239447B2 (en) * 2010-04-15 2016-03-17 Chromocell Corporation Compounds, compositions, and methods for reducing or eliminating bitter taste
RU2567175C2 (ru) 2010-05-11 2015-11-10 Симрайз Аг Применение рубузозида для ослабления или подавления некоторых неприятных вкусовых ощущений
US8939388B1 (en) 2010-09-27 2015-01-27 ZoomEssence, Inc. Methods and apparatus for low heat spray drying
US9332776B1 (en) 2010-09-27 2016-05-10 ZoomEssence, Inc. Methods and apparatus for low heat spray drying
WO2012042621A1 (fr) * 2010-09-29 2012-04-05 味の素株式会社 Exhausteur de saveur salée
WO2012149106A1 (fr) 2011-04-29 2012-11-01 The Board Of Trustees Of The Leland Stanford Junior University Compositions et procédés d'augmentation de la prolifération de cellules souches salivaires adultes
EP2517574B1 (fr) 2011-04-29 2015-11-11 Symrise AG Lignanes vanillyl spécifiques et leur utilisation comme améliorateurs de goût
ES2433004T3 (es) 2011-05-31 2013-12-05 Symrise Ag Amidas de ácido cinámico como sustancias saporíferas especiadas
EP2529633B1 (fr) 2011-06-01 2014-08-06 Symrise AG Préparations consommables oralement comprenant du triterpène et du triterpènglycoside au goût sucré
KR101604053B1 (ko) * 2011-08-05 2016-03-16 (주)아모레퍼시픽 신규 벤조산아미드 화합물
EP2559346B1 (fr) 2011-08-15 2014-03-26 Symrise AG Glycosides de triterpène de type oléanène en tant qu'agents de masquage
EP2570035B1 (fr) 2011-09-15 2014-06-18 Symrise AG Utilisation de néoflavonoïdes pour la modification du goût
EP2570036B1 (fr) 2011-09-15 2014-06-18 Symrise AG Utilisation de néoflavonoïdes précis pour le renforcement et/ou la production d'une impression sensorielle sucrée
DE102011085136A1 (de) 2011-10-24 2013-04-25 Deutsches Institut für Ernährungsforschung - Stiftung des öffentlichen Rechts - Aromatische N-Acylguanidine als Geschmacksstoffe
WO2013074811A1 (fr) 2011-11-15 2013-05-23 Dr Pepper/Seven Up, Inc. Modificateurs de goût
DE102012214560A1 (de) 2011-12-02 2013-06-06 Symrise Ag Bestimmte Lignane und deren Verwendung als Geschmacksverbesserer
EP2614727B1 (fr) 2012-01-10 2016-09-07 Symrise AG N-nonanoylvanillylamine comme moyen de réduction de l'appétit, comme moyen de transmission d'une sensation de satiété ainsi que produits consommables oralement et procédé
EP2633885A1 (fr) 2012-03-02 2013-09-04 Symrise AG Liaisons et mélanges destinés à influencer les états inflammatoires
EP2756765B1 (fr) 2013-01-17 2019-03-27 Symrise AG Compositions pharmaceutiques
JP6410790B2 (ja) 2013-03-14 2018-10-24 ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー ミトコンドリアアルデヒドデヒドロゲナーゼ−２調節因子およびその使用方法
KR101467673B1 (ko) * 2013-03-26 2014-12-04 계명대학교 산학협력단 신규한 페놀산 유도체 및 이의 항산화제로서의 용도
EP2873328B1 (fr) 2013-11-17 2020-10-28 DMK Deutsches Milchkontor GmbH Procédé de fabrication d'une pizza surgelée garnie d'un produit laitier acidifié ayant de bonnes propriétés de cuisson et une grande stabilité à la congélation-décongélation
EP2883459B1 (fr) 2013-12-16 2018-04-04 Symrise AG Compositions pour consommation orale
EP2915429B1 (fr) 2014-03-04 2019-01-09 DMK Deutsches Milchkontor GmbH Mass du protéine pour utilisation comme une succédané du fromage
EP2936991B1 (fr) 2014-04-24 2018-03-28 DMK Deutsches Milchkontor GmbH Lait stérilisé sans conservateurs
EP2952103B1 (fr) 2014-06-05 2019-05-08 Symrise AG Mixtures de matières
EP2990036B1 (fr) 2014-07-30 2019-04-10 Symrise AG Hydroxyflavones pour stimulation d'appétit
EP3078273A1 (fr) 2015-04-08 2016-10-12 DMK Deutsches Milchkontor GmbH Produits du lait acidulé comme base pour deserts cocktail
EP3085239A1 (fr) 2015-04-25 2016-10-26 DMK Deutsches Milchkontor GmbH Excipient de fromage stérile
EP3132695A1 (fr) 2015-05-18 2017-02-22 DMK Deutsches Milchkontor GmbH Compositions de protéines solides
US10736829B2 (en) 2015-09-30 2020-08-11 Symrise Ag Use of certain hydroxybenzoic acid amides for masking unpleasant taste impressions
US20180360086A1 (en) 2015-10-29 2018-12-20 Symrise Ag Foodstuff (iii)
AU2016405259A1 (en) 2016-04-28 2018-07-19 Symrise Ag Use of 3-(3-Hydroxy-4-methoxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-one
CN109310130B (zh) 2016-05-05 2022-05-17 西姆莱斯股份公司 清凉物质混合物
WO2017198284A1 (fr) 2016-05-14 2017-11-23 Symrise Ag Préparations aromatiques mentholées
US10155234B1 (en) 2017-08-04 2018-12-18 ZoomEssence, Inc. Ultrahigh efficiency spray drying apparatus and process
CA3071115C (fr) 2017-08-04 2022-06-21 ZoomEssence, Inc. Appareil et procede de sechage par pulverisation a tres haut rendement
US10486173B2 (en) 2017-08-04 2019-11-26 ZoomEssence, Inc. Ultrahigh efficiency spray drying apparatus and process
US9861945B1 (en) 2017-08-04 2018-01-09 ZoomEssence, Inc. Ultrahigh efficiency spray drying apparatus and process
US9993787B1 (en) 2017-08-04 2018-06-12 ZoomEssence, Inc. Ultrahigh efficiency spray drying apparatus and process
CN111132558A (zh) 2017-10-23 2020-05-08 西姆莱斯有限公司 芳香组合物
EP3709820A1 (fr) 2017-11-14 2020-09-23 Symrise AG Mélanges à activité antimicrobienne
US10569244B2 (en) 2018-04-28 2020-02-25 ZoomEssence, Inc. Low temperature spray drying of carrier-free compositions
WO2020015816A1 (fr) 2018-07-16 2020-01-23 Symrise Ag Composition de substitution de sucre dans les pâtisseries
WO2020147977A1 (fr) 2019-01-18 2020-07-23 Symrise Ag Agent de combinaison
EP3689324A1 (fr) 2019-02-04 2020-08-05 Symrise AG Nouveux agents rafraichissantes et preparations les contenant
EP3864966A1 (fr) 2020-02-12 2021-08-18 Savanna Ingredients GmbH Compositiones orales contenant crystals d'allulose
US20230139835A1 (en) 2020-02-12 2023-05-04 Savanna Ingredients Gmbh Allulose in crystalline form
WO2022105986A1 (fr) 2020-11-17 2022-05-27 Symrise Ag Nouveaux agents de refroidissement et préparations les contenant
WO2023117119A1 (fr) 2021-12-23 2023-06-29 Symrise Ag Ingrédients actifs présentant un effet sialagogue et un effet de picotement et de vertige et préparations les contenant
WO2023143741A1 (fr) 2022-01-28 2023-08-03 Symrise Ag Nouveaux réfrigérants et préparations les contenant

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5637618A (en) * 1990-06-01 1997-06-10 Bioresearch, Inc. Specific eatable taste modifiers
WO1992020645A1 (fr) * 1991-05-20 1992-11-26 Tsumura & Co. Analogues de phellodendrine et suppresseur d'allergie de type iv les contenant en tant qu'ingredients actifs
DE10122898A1 (de) * 2001-05-11 2002-11-14 Haarmann & Reimer Gmbh Verwendung von Hydroxyflavanonen zur Maskierung des bitteren Geschmacks
SI2527315T1 (sl) * 2002-05-31 2014-06-30 Proteotech Inc., Spojine, sestavki in metode za zdravljenje amiloidnih bolezni in sinukleinopatij, kot so Alzheimerjeva bolezen, diabetes tipa 2 in Parkinsonova bolezen
JPWO2004026292A1 (ja) * 2002-09-20 2006-01-12 株式会社ツムラ 鎮咳薬

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006024587A1 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107667088A (zh) * 2015-03-31 2018-02-06 株式会社爱茉莉太平洋 新型苯甲酸酰胺化合物
CN107667088B (zh) * 2015-03-31 2020-04-24 株式会社爱茉莉太平洋 新型苯甲酸酰胺化合物
WO2017186298A1 (fr) 2016-04-28 2017-11-02 Symrise Ag Dérivés de dihydrochalcone influençant des états inflammatoires

Also Published As

Publication number Publication date
DE102004041496A1 (de) 2006-03-02
US20080214675A1 (en) 2008-09-04
WO2006024587A8 (fr) 2006-05-18
WO2006024587A1 (fr) 2006-03-09

Similar Documents

Publication Publication Date Title
EP1784088A1 (fr) Amides d&#39;acide hydroxybenzoique et leur utilisation pour masquer un gout amer
EP1972203B1 (fr) Utilisation de dérivés de 4-hydroxychalcone pour masquer un goût désagréable
EP2253226B1 (fr) Utilisation de dérivés d&#39;hydroxyflavane pour la modification du goût
EP2570036B1 (fr) Utilisation de néoflavonoïdes précis pour le renforcement et/ou la production d&#39;une impression sensorielle sucrée
EP2529633B1 (fr) Préparations consommables oralement comprenant du triterpène et du triterpènglycoside au goût sucré
EP2570035B1 (fr) Utilisation de néoflavonoïdes pour la modification du goût
EP2353403B1 (fr) Utilisation de 1-(2,4-dihydroxy-phényle)-3-(3-hydroxy-4-méthoxy-phényle)-propane-1-on
EP2064959B1 (fr) Néomenthylamides aromatiques en tant qu&#39;agents aromatisants
EP2008530B1 (fr) Composition d&#39;aromes destinée à réduire ou à supprimer une impression indésirable amère et astringente
EP1868452B1 (fr) Hydroxydeoxybenzoines permettant de masquer un gout amer
EP3142499B1 (fr) Ester d&#39;acide homovallinique, en particulier pour obtenir une impression de chaleur et/ou de netteté
EP2597082A1 (fr) Composés destinés à masquer un goût désagréable
EP2298084A1 (fr) Produits réduits en saccharine, mélanges d&#39;arômes correspondant et procédé de fabrication de tels produits
WO2005096841A1 (fr) Utilisation d&#39;acide $g(y)-aminobutyrique afin de masquer ou de reduire l&#39;impression de mauvaise odeur et preparation contenant de l&#39;acide $g(y)-aminobutyrique
EP1901618A1 (fr) Hydroxyphénylalcadiones et leur utilisation pour masquer un goût amer et/ou pour intensifier un goût sucré
DE10351422A1 (de) Verwendung von Alkencarbonsäure-N-alkylamiden als Aromastoffe
DE102004032878A1 (de) Verwendung von Alkyloxyalkansäureamiden insbesondere als Aromastoffe sowie neue Alkyloxyalkansäureamide
EP3687311A1 (fr) Amide destiné à produire un effet trigéminal
DE102012214560A1 (de) Bestimmte Lignane und deren Verwendung als Geschmacksverbesserer
DE102009046126A1 (de) Oral konsumierbare Zubereitung umfassend Wurzelextrakt aus Mondia whitei
DE102009002268A1 (de) 4,4&#39;-Dihydroxydeoxybenzoine und deren Verwendung als Geschmacksverbesserer
WO2021160701A1 (fr) Allulose sous forme cristalline
DE102006006123A1 (de) Verwendung von Alk-2-en-4-insäureamiden als Aromastoffe
EP3641564B1 (fr) Agents aromatiques modulant la saveur
WO2023117119A1 (fr) Ingrédients actifs présentant un effet sialagogue et un effet de picotement et de vertige et préparations les contenant

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20070327

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20080403

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: SYMRISE AG

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20120301