CA2385510A1 - Use of hydroxyflavanones for masking bitter taste - Google Patents
Use of hydroxyflavanones for masking bitter taste Download PDFInfo
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- CA2385510A1 CA2385510A1 CA002385510A CA2385510A CA2385510A1 CA 2385510 A1 CA2385510 A1 CA 2385510A1 CA 002385510 A CA002385510 A CA 002385510A CA 2385510 A CA2385510 A CA 2385510A CA 2385510 A1 CA2385510 A1 CA 2385510A1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F3/00—Tea; Tea substitutes; Preparations thereof
- A23F3/40—Tea flavour; Tea oil; Flavouring of tea or tea extract
- A23F3/405—Flavouring with flavours other than natural tea flavour or tea oil
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
Abstract
The invention relates to hydroxyflavanones, their salts and stereoisomers and their mixtures for suppressing or reducing the bitter and/or metallic taste impression. In addition, the invention relates to nutritional, nutritive or consumable preparations or oral pharmaceutical compositions, characterized in that these have an active content of hydroxyflavanones, their salts and stereoisomers or their mixtures.
Description
Mo-6917 HR 313-US TS/klu USE OF HYDROXYFLAVANONES FOR MASKING BITTER TASTE
FIELD OF THE INVENTION
The invention relates to the use of hydroxyl-substituted 2-phenylchroman-4-ones (termed hydroxyflavanones hereinafter), their salts and stereoisomers and mixtures thereof for masking or reducing bitter and/or metallic taste impression. The invention also relates to nutritional, nutritive or consumable preparations, or oral pharmaceutical preparations, characterized in that these have an active content of the designated hydroxyflavanones, their salts and stereoisomers and mixtures of the same.
BACKGROUND OF THE INVENTION
Foods or drinks frequently contain various bitter substances which, although they are characteristic (for example, caffeine in tea or coffee), they can also greatly decrease the value (for example limonoids in citrus juices, bitter aftertaste of many synthetic sweeteners such as aspartame or saccharin). To lower the natural content of bitter substances, therefore, frequently subsequent treatment is necessary, for example by extraction 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 ripening of cheese. This treatment causes stress to the product, produces wastes and also produces, for example, solvent residues and other residues (enzymes) in the products. It is, therefore, desirable to find substances, preferably natural or nature-identical substances, which can effectively suppress, or at least decrease, the bitter taste or aftertaste.
Suppressing the bitter taste in many pharmaceutically active compounds is particularly important, since, as a result, the readiness of the patients, in particular in the case of patients who are sensitive to bitter taste, such as children, to take the preparation orally, can be significantly increased. Many pharmaceutically active compounds, for example quinine, have a pronounced bitter taste and/or aftertaste.
To date, only a few substances have been described which suppress bitterness and have no inherent taste. Thus, U.S. Patent No. 6,083,459 describes bitter-masking amino acid derivatives which do not, however, occur in nature. 2(-4-~Methoxyphenoxy)propionic acid sodium salt (Lactisol) exhibits a weak bitter-reducing effect at relatively high concentrations (450 ppm), as reported in Chem. Senses, 1994, vol. 19, pp. 349 ff.; however, it is a problem that the substance at the same time suppresses the sweet taste impression (U.S. Patent No. 4,567,053).
Neohesperidin dihydrochalcone also exhibits a bitter-reducing effect, but is primarily a sweetener (see Manufacturing Chemist 2000, July issue, pp. 16-17), which,also has a disturbing action in non-sweet applications.
Although U.S. Patent No. 5,580,545 describes taste-modifying properties for some flavones (2-phenylchrom-2-en-4-ones), a bitter-reducing or bitter-suppressing action was not found.
Sodium chloride exhibits a bitter-masking effect against many bitter substances (e.g. Nature, 1997, vol. 387, p. 563); however, the intake of relatively large amounts of salt can lead, for example, to cardiovascular disorders.
Concentrated extracts of Herba Santa or simple aqueous or alcoholic extracts of the same exhibit a weak bitter-masking action towards quinine; however, to date the individual constituents have not been analyzed for their activity; in addition, the extracts display a rather strong herb-like inherent taste.
WO 00/21,390 describes polyglutamic acid as a bitterness-suppressing agent; relatively high concentrations in the region of 1 % by weight are required. A lipoprotein consisting of ~i-lactoglobulin and phosphatic acid also exhibits a bitter-masking effect (EP-A 635 218). Such polymers, however, are difficult to characterize and to standardize.
The flavone glycoside Neodiosmin (5,7-dihydroxy-2-(4-methoxy-3-hydroxyphenyl)-7-O-neohesperidosyl-chrom-2-en-4-one) shows a bitter-suppressing action (U.S. Patent No. 4,154,862), but features a disaccharide radical which makes preparation and applicability of the substance difficult.
SUMMARY OF THE INVENTION
It was an object of the present invention to find readily accessible low molecular weight substances which exhibit a bitter-suppressing effect against a multiplicity of bitter substances.
The invention therefore relates to the use of compounds of the general formula (I) :20 R' R6 (I) where R' to R9 independently of one another denote hydrogen atoms, hydroxyl groups, methyl, ethyl, 1-propyl, 2-propyl, methoxy, R' O
ethoxy, 1-propyloxy or 2-propyloxy groups, with the proviso that at least one of the radicals R' to R9 represents a hydroxyl group, as a constituent of nutritional, nutritive or consumable preparations, and also oral pharmaceutical preparatians, comprising at least one bitter substance or a substance which causes a bitter aftertaste, for masking or reducing the bitter or metallic taste impression.
BRIEF DESCRIPTION OF THE DRAWING
Fig. 1 shows a graph of the course of bitterness intensity of a solution containing 500 ppm of caffeine with increasing concentration of (2S)-homoeriodictyol disodium salt compared with a series of caffeine concentrations (100 to 500 ppm) Fig 2 shows a graph of the estimated caffeine intensity of a solution containing 500 ppm of caffeine and 100 ppm of an exemplary hydroxyflavanone.
Fig. 3 shows a graph of the decrease in bitter intensity for paracetamol.
DETAILED DESCRIPTION OF THE INVENTION
Bitter substances within the meaning of the invention can be, for example: xanthine alkaloids (for example caffeine, theobromine), quinoline derivatives (for example quinine) limonoids {for example limonine from citrus fruits), polyphenols (for example catechols, flavonols, y-oryzanol, hesperitin), pharmaceutically active compounds (for example fluoroquinolone antibiotics, aspirin, ~-lactam antibiotics, ambroxol, paracetamol, aspirin, guaifenesin), denatonium benzoate, sucralose octaacetate, potassium chloride, magnesium salts, urea, bitter amino acids (for example tryptophan) and bitter peptide fragments (for example having a terminal leucine or isoleucine radical).
Substances which have a bitter aftertaste within the meaning of the invention can be, for example: aspartame, neotame, saccharin and cyclamate.
The nutritional, nutritive or consumable preparations within the meaning of the present invention are, for example, bakery products (for example bread, dried biscuits, cake, other bakery products), confectionery (for example chocolates, hard and soft toffees, chewing gum), alcoholic or non-alcoholic beverages (for example coffee, tea, wine, beer, liqueurs, spirits, wine brandies, fruit-containing lemonades, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks, meat products (for example ham, sausage preparations), cereal products (for example breakfast cereals, muesli bars), milk products (for example milk drinks, dairy ice-cream, yogurt, kefir, cheese, dried milk powder, whey), fruit preparations (for example jams, fruit ice, fruit sauces), vegetable preparations (for example ketchup, sauces), snack items (for example fried potato crisps, maize- or peanut-based extrudates), oil- and fat-based products or emulsions of the same (for example mayonnaise, remoulade, dressings), seasonings, fragrance, flavoring and taste compositions, spice mixtures, ready-to-eat dishes and soups. The preparations within the meaning of the invention, particularly preferably the fragrance, flavoring and taste compositions and spice mixtures, can also, as semi-manufactured products, serve for producing further preparations serving for nutrition or pleasure.
Oral pharmaceutical preparations within the meaning of the invention are preparations which exist, for example, in the form of capsules, tablets (non-coated and coated tablets, for example coatings resistant to gastric juice), dragees, granules, pellets, solids mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other preparations which can be swallowed or chewed, and are used as drugs requiring prescriptions, sale by pharmacist or other drugs, or as food supplements.
Preference is given to the use of compounds of the general formula (I), where R2, R4, R5 and R9 represent hydrogen atoms, R', R3, R6, R' and R8 independently of one another denote hydrogen atoms, hydroxyl groups, methyl, methoxy or ethoxy groups, with the proviso that at least one of the radicals R6 to Rs represents a hydroxyl group, as a constituent of nutritional, nutritive or consumable preparations, and also oral pharmaceutical preparations comprising at least one bitter substance or a substance causing a bitter aftertaste, for masking or reducing the bitter or metallic taste impression.
;20 Preference is given to the use of compounds of the general formula (I), where R2, R4, R5, R8 and R9 represent hydrogen atoms, R', R3 and R6 independently of one another denote hydrogen atoms, hydroxyl or methoxy groups" with the proviso that at least one of the radicals R' and R3 represents a hydroxyl group, and R' represents a hydroxyl group, in nutritional, nutritive or consumable preparations and also oral pharmaceutical preparations comprising at least one bitter substance or a substance which causes a bitter aftertaste, for masking or reducing the bitter or metallic taste impression.
The inventive hydroxyflavanones can preferably exist as monovalent anions, or, in the case of a plurality of hydroxyl groups, as polyvalent anions, where the counterions are the cations with a single positive charge of the first main graup and subgroup of the Periodic Table of the Elements, the ammonium ion, a trialkylammonium ion, the cations with a double charge of the second main group and subgroup of the Periodic Table of the Elements, and the trivalent cations of the 3rd main group and subgroup, preferably Na+, K+, NH4'', Ca2+, Mg2+, AI3+ and Zn2+.
The inventive hydroxyflavanones can exist as (2S)- or (2R)-enantiomers or as a mixture of the two. Preferably, the inventive hydroxyflavanones are present as a (2S)-enantiomer or as a (2S)-enantiomer-enriched mixture.
Without restricting the invention thereto, the following exemplary compounds may be mentioned: 2-(4-hydroxyphenyl)-5,7-dihydroxychroman-4-one (naringenin), 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-4-one (eriodictyol), 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychroman-4-one (eriodictyol 7-methyl ether), 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxychroman-4-one (eriodictyol 5-methyl ether) and 2-(4-hydroxy-3-methoxyphenyl)-5,7-dihydroxychroman-4-one (homoeriodictyol), their (2S)- or (2R)-enantiomers, or mixtures of the same and their monovalent or polyvalent phenolate salts with Na~~, K+, NH4+, Ca2+, Mg2+ or AI3+ as counterions.
The diagram below illustrates the structures of the inventive examples preferred in particular:
H H H
\ \ \
Ho I '~ o '\ Ho ~ / .o I \ off Ho ( ,i o I ~ ocH, I / / OH /
Naringenin OH ~~~~1 Homoeriodictyol OH
HOC
\ \
H~C~O I / O \ OH ~ I r O \ off OH OH
Eriodietyol - 7-methyl ether Eriodictyol - 5-methyl ether The monosodium and disodium salts of (+)-(2S)-homoeriodictyol are preferred.
Obviously, the various inventive hydroxyffavanones, their stereoisomers and salts can be used according to the present invention in each case, alone or as mixtures.
Surprisingly, it has been found that the inventive hydroxyffavanones, even at very low concentrations, can reduce or even completely suppress the bitter taste impression of a multiplicity of bitter substances, in particular of methylxanthines, for example caffeine, alkaloids, for example quinine, flavonoids, for example naringin, inorganic salts, such as potassium chloride or magnesium sulfate, pharmaceutically active compounds, for example ~3-lactam antibiotics, paracetamol, guaifenesin, in which case it is particularly advantageous that the inventive hydroxyflavanones have virtually no inherent taste. In particular, the inventive hydroxyflavanones are active directly in the preparation on intake into the mouth, and need not be consumed prior to the bitter substance.
Some of the hydroxyflavanones have long been known and have been found 'in nature; for example naringenin occurs in grapefruits bound as glycoside; homoeriodictyol has been isolated as minor component from Chryothamnus spp. (Phytochemistry, 1999, volume 51, issue 6, pp. 771-780) and has been isolated together with eriodictyol from Eriodictyon californicum (J. Am. Chem. Soc. 1940, volume 62, p. 3285).
Eriodictyol 7-methyl ether has been isolated from Dubantia arborea (Biochem. Syst. Ecol., 1999, vol. 27, issue 7, pp. 755-757).
The invention further relates to nutritional, nutritive or consumable preparations or oral pharmaceutical preparations characterized in that they have an active content of hydroxyflavanones, their salts or their mixtures.
They generally comprise 0.000001 % by weight to 10% by weight, preferably 0.00001 % to 1 % by weight, but more preferably 0.0001 % by weight to 0.1 % by weight, based on the total weight of the preparation, of inventive hydroxyflavanones, their salts or their mixtures. Other customary active compounds, base compounds, aids and additives for food consumed for nutrition or pleasure or oral pharmaceutical preparations can be present in amounts of 5 to 99.999999% by weight, preferably 10 to 80%
by weight, based on the total weight of the preparation. In addition, the preparations can comprise water in an amount up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
The inventive preparations that serve as semi-manufactured products generally comprise 0.0001 % by weight to 95% by weight, preferably 0.1 to 80% by weight, but in particular 1 % by weight to 50% by weight, based on the total weight of the preparation, of inventive hydroxyflavanones, their salts or their mixtures.
The inventive preparations comprising one or more of the inventive hydroxyflavanones are produced in such a manner that the inventive hydroxyflavanones are incorporated into the nutritional, nutritive or consumable preparations as the substances themselves, as solution or in the form of a mixture with a solid or liquid carrier.
To produce the preparations, in a further embodiment, the inventive hydroxyflavanones and, if appropriate, other constituents of the inventive preparation can also be incorporated in advance into emulsions, into liposomes, for example based on phosphatidylcholine, into microspheres, into nanospheres or into capsules made of a matrix suitable for foods and drinks, for example made of starch, starch derivatives, other polysaccharides, natural fats, natural waxes or proteins, for example gelatin. A further embodiment is that the inventive hydroxyflavanones are complexed in advance with suitable complexing agents, for example with cyclodextrins or cyclodextrin derivatives, preferably ~i-cyclodextrin, and are used in this form.
Other constituents which can be used for the inventive nutritional, nutritive or consumable preparations are customary bases, aids, and additives for foods and drinks, for example water, mixtures of fresh or processed, plant or animal, base substances or raw materials (for example raw, roasted/fried, dried, fermented, smoked and/or boiled meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or their mixtures), digestible or indigestible carbohydrates (for example sucrose, maltose, fructose, glucose, dextrins, amylose, amylopectin, inulin, xylan, cellulose), sugar alcohols (for example sorbitol), natural or hardened fats (for example tallow, lard, palm fat, coconut fat, hardened vegetable fat), oils (for example sunflower oil, peanut oil, corn oil, olive oil, fish oil, soya bean oil, sesame oil), fatty acids or their salts (for example potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (for example taurine), peptides, native or processed proteins (for example gelatin), enzymes (for example peptidases), nucleic acids, nucleotides, flavor enhancers (for example sodium glutamate, inositol phosphate, 2-phenoxypropionic acid), emulsifiers (for example lecithins, diacylglycerols, monoacylglycerols), stabilizers (for example caragheenan, alginate), preservatives (for example benzoic acid, sorbic acid), antioxidants (for example tocopherol, ascorbic acid), chelators (for example citric acid), organic or inorganic acidulants (for example malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid), additional bitter substances (for example quinine, caffeine, limonine), sweeteners (for example saccharin, cyclamate, aspartame, neotame), mineral salts (for example sodium chloride, potassium chloride, magnesium chloride, sodium phosphates), the substances inhibiting enzymatic browning (for example sulfur dioxide, sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or colored pigments (for example carotenoids, flavonoids, anthocyans, chlorophylls and their derivatives), spices, synthetic, natural or nature identical flavorings or fragrances and odor-correctives and taste-correctives not affecting the bitter taste.
Other constituents which can be used for the inventive oral pharmaceutical preparations are all customary further active compounds, base substances, aids and additives for oral pharmaceutical preparations.
Active compounds which can be used are all bitter- or metallic-tasting pharmaceutical compounds which can be formulated for oral preparations.
The active compounds, base substances, aids and additives can be converted into the oral dosage forms in a manner known per se. This takes place with the use of inert non-toxic pharmaceutically compatible aids.
These include, inter alia, carriers (for example microcrystalline cellulose), solvents (for example liquid polyethylene glycols), emulsifiers (for example sodium dodecyl sulfate), dispersants (for example polyvinylpyrrolidone), synthetic and natural biopolymers (for example albumin), stabilizers (for example antioxidants such as ascorbic acid), colorants (for example inorganic pigments such as iron oxides) or odor-correctives and taste-correctives not affecting the bitter taste.
Preferably, the inventive preparations can also comprise a flavoring composition to round and refine the taste and/or odor of the preparation.
Suitable flavoring compositions comprise, for example, synthetic, natural or nature identical flavorings, fragrances and taste substances and suitable aids and carriers. It is considered here to be particularly advantageous that the bitter or metallic taste impression can be suppressed or reduced by filavorings or fragrances present in the inventive flavoring compositions and thus the entire flavor or taste profile can be improved.
The invention further relates to the use of the nutritional, nutritive or consumable preparations, or pharmaceutical preparations, as semi-manufactured products for suppressing or reducing the bitter taste or aftertaste of preparations manufactured therefrom as finished products.
Finished products within the meaning of the invention are ready to use products for end consumers and are, for example, mentioned on page 5 of the specification.
Semi-finished products within the meaning of the invention are preparations, which were mixed or blended with other semi-finished food products or finished products.
EXAMPLES
The examples serve only to illustrate the invention, without restricting it thereto.
Example 1: Debittering black tea Two different types of black tea were brewed using boiling water (3 g of tea to 100 ml, allowed to infuse for 3 min, filter) and were then tasted by an expert group. The bitterness was rated using a scale of 1 to 5 (1 just perceptibly bitter, 5 very bitter). The results are shown in the table below:
Table 1 Sample Rating (1-5) Tea sample 1 3.5 Tea sample 2 5 Tea sample 2 2 + 0.05% homoeriodictyol disodium salt Example 2: Masking the bitter taste of a [i-lactam antibiotic A solution of Faropenem Daloxate ([5R-[3(R*),5a,6a(R*)]]-6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-4-this-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester, CAS No. 141702-36-5, 0.1 % by weight in water, sample 1 ) and a mixture of Faropenem Daloxate + homoeriodictyol di-sodium salt (each 0.1 % by weight in water, sample 2) were made up. A
group of 7 testers were each given 3 samples for difference testing. 4 testers received sample 1 as a duplicate sample, 3 testers received sample 2 as a duplicate sample. The samples were tasted in differing orders. Of 7 testers, 7 correctly identified the individual sample. The average bitter intensity of sample 1 was rated 5, that of sample 2 was rated 2 (scale 1 to 5).
Example 3: Reducing bitterness of a caffeine solution by (2S)-homoeriodictyol disodium salt To quantify the reduction in bitter impression, the bitterness of a 500 ppm-containing caffeine solution and a sample which contained 500 ppm of caffeine and various amounts of (2S)-homoeriodictyol disodium salt was determined.
To categorize the test samples, a reference series was prepared using 10 different concentrations of caffeine in water (50, 100, 150, 200, 250, 300, 350, 400, 450 and 500 ppm). In the diagram hefeir~aft~r, the dependence of recognition of bitterness on the amount of homoeriodictyol disodium salt added may be seen:
Fig. 1 shows the course of bitterness intensity of a solution containing 500 ppm of caffeine with increasing concentration of (2S)-homoeriodictyol disodium salt compared with a series of caffeine concentrations (100 to 500 ppm) Examale 4: Reduction in bitterness of a caffeine solution by various hydroxyflavanones Similarly to Example 3, a caffeine solution (500 ppm) with or without 100 ppm of (2S)-homoeriodictyol, (2S)-homoeriodictyol disodium salt, (2S)-eriodictyol, (2S)-eriodictyol 7-methyl ether and (2S)-naringenin was tasted and classified on the basis of the reference series.
Fig 2 shows the estimated caffeine intensity of a solution containing 500 ppm of caffeine and 100 ppm of an exemplary hydroxyflavanone.
Example 5 The bitter impressions of a paracetamol solution, a paracetamollhomoeriodictyol disodium salt solution and a solution containing paracetamol/homoeriodictyol disodium salt and chocolate flavoring were classified on a scale of 1 to 9.
Fig. 3 shows the decrease in bitter intensity for paracetamol.
Although the invention has been described in detail in the foregoing for the purpose of illustration, it is to be understood that such detail is solely for that purpose and that variations can be made therein by those skilled in the art without departing from the spirit and scope of the invention except as it may be limited by the claims.
FIELD OF THE INVENTION
The invention relates to the use of hydroxyl-substituted 2-phenylchroman-4-ones (termed hydroxyflavanones hereinafter), their salts and stereoisomers and mixtures thereof for masking or reducing bitter and/or metallic taste impression. The invention also relates to nutritional, nutritive or consumable preparations, or oral pharmaceutical preparations, characterized in that these have an active content of the designated hydroxyflavanones, their salts and stereoisomers and mixtures of the same.
BACKGROUND OF THE INVENTION
Foods or drinks frequently contain various bitter substances which, although they are characteristic (for example, caffeine in tea or coffee), they can also greatly decrease the value (for example limonoids in citrus juices, bitter aftertaste of many synthetic sweeteners such as aspartame or saccharin). To lower the natural content of bitter substances, therefore, frequently subsequent treatment is necessary, for example by extraction 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 ripening of cheese. This treatment causes stress to the product, produces wastes and also produces, for example, solvent residues and other residues (enzymes) in the products. It is, therefore, desirable to find substances, preferably natural or nature-identical substances, which can effectively suppress, or at least decrease, the bitter taste or aftertaste.
Suppressing the bitter taste in many pharmaceutically active compounds is particularly important, since, as a result, the readiness of the patients, in particular in the case of patients who are sensitive to bitter taste, such as children, to take the preparation orally, can be significantly increased. Many pharmaceutically active compounds, for example quinine, have a pronounced bitter taste and/or aftertaste.
To date, only a few substances have been described which suppress bitterness and have no inherent taste. Thus, U.S. Patent No. 6,083,459 describes bitter-masking amino acid derivatives which do not, however, occur in nature. 2(-4-~Methoxyphenoxy)propionic acid sodium salt (Lactisol) exhibits a weak bitter-reducing effect at relatively high concentrations (450 ppm), as reported in Chem. Senses, 1994, vol. 19, pp. 349 ff.; however, it is a problem that the substance at the same time suppresses the sweet taste impression (U.S. Patent No. 4,567,053).
Neohesperidin dihydrochalcone also exhibits a bitter-reducing effect, but is primarily a sweetener (see Manufacturing Chemist 2000, July issue, pp. 16-17), which,also has a disturbing action in non-sweet applications.
Although U.S. Patent No. 5,580,545 describes taste-modifying properties for some flavones (2-phenylchrom-2-en-4-ones), a bitter-reducing or bitter-suppressing action was not found.
Sodium chloride exhibits a bitter-masking effect against many bitter substances (e.g. Nature, 1997, vol. 387, p. 563); however, the intake of relatively large amounts of salt can lead, for example, to cardiovascular disorders.
Concentrated extracts of Herba Santa or simple aqueous or alcoholic extracts of the same exhibit a weak bitter-masking action towards quinine; however, to date the individual constituents have not been analyzed for their activity; in addition, the extracts display a rather strong herb-like inherent taste.
WO 00/21,390 describes polyglutamic acid as a bitterness-suppressing agent; relatively high concentrations in the region of 1 % by weight are required. A lipoprotein consisting of ~i-lactoglobulin and phosphatic acid also exhibits a bitter-masking effect (EP-A 635 218). Such polymers, however, are difficult to characterize and to standardize.
The flavone glycoside Neodiosmin (5,7-dihydroxy-2-(4-methoxy-3-hydroxyphenyl)-7-O-neohesperidosyl-chrom-2-en-4-one) shows a bitter-suppressing action (U.S. Patent No. 4,154,862), but features a disaccharide radical which makes preparation and applicability of the substance difficult.
SUMMARY OF THE INVENTION
It was an object of the present invention to find readily accessible low molecular weight substances which exhibit a bitter-suppressing effect against a multiplicity of bitter substances.
The invention therefore relates to the use of compounds of the general formula (I) :20 R' R6 (I) where R' to R9 independently of one another denote hydrogen atoms, hydroxyl groups, methyl, ethyl, 1-propyl, 2-propyl, methoxy, R' O
ethoxy, 1-propyloxy or 2-propyloxy groups, with the proviso that at least one of the radicals R' to R9 represents a hydroxyl group, as a constituent of nutritional, nutritive or consumable preparations, and also oral pharmaceutical preparatians, comprising at least one bitter substance or a substance which causes a bitter aftertaste, for masking or reducing the bitter or metallic taste impression.
BRIEF DESCRIPTION OF THE DRAWING
Fig. 1 shows a graph of the course of bitterness intensity of a solution containing 500 ppm of caffeine with increasing concentration of (2S)-homoeriodictyol disodium salt compared with a series of caffeine concentrations (100 to 500 ppm) Fig 2 shows a graph of the estimated caffeine intensity of a solution containing 500 ppm of caffeine and 100 ppm of an exemplary hydroxyflavanone.
Fig. 3 shows a graph of the decrease in bitter intensity for paracetamol.
DETAILED DESCRIPTION OF THE INVENTION
Bitter substances within the meaning of the invention can be, for example: xanthine alkaloids (for example caffeine, theobromine), quinoline derivatives (for example quinine) limonoids {for example limonine from citrus fruits), polyphenols (for example catechols, flavonols, y-oryzanol, hesperitin), pharmaceutically active compounds (for example fluoroquinolone antibiotics, aspirin, ~-lactam antibiotics, ambroxol, paracetamol, aspirin, guaifenesin), denatonium benzoate, sucralose octaacetate, potassium chloride, magnesium salts, urea, bitter amino acids (for example tryptophan) and bitter peptide fragments (for example having a terminal leucine or isoleucine radical).
Substances which have a bitter aftertaste within the meaning of the invention can be, for example: aspartame, neotame, saccharin and cyclamate.
The nutritional, nutritive or consumable preparations within the meaning of the present invention are, for example, bakery products (for example bread, dried biscuits, cake, other bakery products), confectionery (for example chocolates, hard and soft toffees, chewing gum), alcoholic or non-alcoholic beverages (for example coffee, tea, wine, beer, liqueurs, spirits, wine brandies, fruit-containing lemonades, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks, meat products (for example ham, sausage preparations), cereal products (for example breakfast cereals, muesli bars), milk products (for example milk drinks, dairy ice-cream, yogurt, kefir, cheese, dried milk powder, whey), fruit preparations (for example jams, fruit ice, fruit sauces), vegetable preparations (for example ketchup, sauces), snack items (for example fried potato crisps, maize- or peanut-based extrudates), oil- and fat-based products or emulsions of the same (for example mayonnaise, remoulade, dressings), seasonings, fragrance, flavoring and taste compositions, spice mixtures, ready-to-eat dishes and soups. The preparations within the meaning of the invention, particularly preferably the fragrance, flavoring and taste compositions and spice mixtures, can also, as semi-manufactured products, serve for producing further preparations serving for nutrition or pleasure.
Oral pharmaceutical preparations within the meaning of the invention are preparations which exist, for example, in the form of capsules, tablets (non-coated and coated tablets, for example coatings resistant to gastric juice), dragees, granules, pellets, solids mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other preparations which can be swallowed or chewed, and are used as drugs requiring prescriptions, sale by pharmacist or other drugs, or as food supplements.
Preference is given to the use of compounds of the general formula (I), where R2, R4, R5 and R9 represent hydrogen atoms, R', R3, R6, R' and R8 independently of one another denote hydrogen atoms, hydroxyl groups, methyl, methoxy or ethoxy groups, with the proviso that at least one of the radicals R6 to Rs represents a hydroxyl group, as a constituent of nutritional, nutritive or consumable preparations, and also oral pharmaceutical preparations comprising at least one bitter substance or a substance causing a bitter aftertaste, for masking or reducing the bitter or metallic taste impression.
;20 Preference is given to the use of compounds of the general formula (I), where R2, R4, R5, R8 and R9 represent hydrogen atoms, R', R3 and R6 independently of one another denote hydrogen atoms, hydroxyl or methoxy groups" with the proviso that at least one of the radicals R' and R3 represents a hydroxyl group, and R' represents a hydroxyl group, in nutritional, nutritive or consumable preparations and also oral pharmaceutical preparations comprising at least one bitter substance or a substance which causes a bitter aftertaste, for masking or reducing the bitter or metallic taste impression.
The inventive hydroxyflavanones can preferably exist as monovalent anions, or, in the case of a plurality of hydroxyl groups, as polyvalent anions, where the counterions are the cations with a single positive charge of the first main graup and subgroup of the Periodic Table of the Elements, the ammonium ion, a trialkylammonium ion, the cations with a double charge of the second main group and subgroup of the Periodic Table of the Elements, and the trivalent cations of the 3rd main group and subgroup, preferably Na+, K+, NH4'', Ca2+, Mg2+, AI3+ and Zn2+.
The inventive hydroxyflavanones can exist as (2S)- or (2R)-enantiomers or as a mixture of the two. Preferably, the inventive hydroxyflavanones are present as a (2S)-enantiomer or as a (2S)-enantiomer-enriched mixture.
Without restricting the invention thereto, the following exemplary compounds may be mentioned: 2-(4-hydroxyphenyl)-5,7-dihydroxychroman-4-one (naringenin), 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-4-one (eriodictyol), 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychroman-4-one (eriodictyol 7-methyl ether), 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxychroman-4-one (eriodictyol 5-methyl ether) and 2-(4-hydroxy-3-methoxyphenyl)-5,7-dihydroxychroman-4-one (homoeriodictyol), their (2S)- or (2R)-enantiomers, or mixtures of the same and their monovalent or polyvalent phenolate salts with Na~~, K+, NH4+, Ca2+, Mg2+ or AI3+ as counterions.
The diagram below illustrates the structures of the inventive examples preferred in particular:
H H H
\ \ \
Ho I '~ o '\ Ho ~ / .o I \ off Ho ( ,i o I ~ ocH, I / / OH /
Naringenin OH ~~~~1 Homoeriodictyol OH
HOC
\ \
H~C~O I / O \ OH ~ I r O \ off OH OH
Eriodietyol - 7-methyl ether Eriodictyol - 5-methyl ether The monosodium and disodium salts of (+)-(2S)-homoeriodictyol are preferred.
Obviously, the various inventive hydroxyffavanones, their stereoisomers and salts can be used according to the present invention in each case, alone or as mixtures.
Surprisingly, it has been found that the inventive hydroxyffavanones, even at very low concentrations, can reduce or even completely suppress the bitter taste impression of a multiplicity of bitter substances, in particular of methylxanthines, for example caffeine, alkaloids, for example quinine, flavonoids, for example naringin, inorganic salts, such as potassium chloride or magnesium sulfate, pharmaceutically active compounds, for example ~3-lactam antibiotics, paracetamol, guaifenesin, in which case it is particularly advantageous that the inventive hydroxyflavanones have virtually no inherent taste. In particular, the inventive hydroxyflavanones are active directly in the preparation on intake into the mouth, and need not be consumed prior to the bitter substance.
Some of the hydroxyflavanones have long been known and have been found 'in nature; for example naringenin occurs in grapefruits bound as glycoside; homoeriodictyol has been isolated as minor component from Chryothamnus spp. (Phytochemistry, 1999, volume 51, issue 6, pp. 771-780) and has been isolated together with eriodictyol from Eriodictyon californicum (J. Am. Chem. Soc. 1940, volume 62, p. 3285).
Eriodictyol 7-methyl ether has been isolated from Dubantia arborea (Biochem. Syst. Ecol., 1999, vol. 27, issue 7, pp. 755-757).
The invention further relates to nutritional, nutritive or consumable preparations or oral pharmaceutical preparations characterized in that they have an active content of hydroxyflavanones, their salts or their mixtures.
They generally comprise 0.000001 % by weight to 10% by weight, preferably 0.00001 % to 1 % by weight, but more preferably 0.0001 % by weight to 0.1 % by weight, based on the total weight of the preparation, of inventive hydroxyflavanones, their salts or their mixtures. Other customary active compounds, base compounds, aids and additives for food consumed for nutrition or pleasure or oral pharmaceutical preparations can be present in amounts of 5 to 99.999999% by weight, preferably 10 to 80%
by weight, based on the total weight of the preparation. In addition, the preparations can comprise water in an amount up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
The inventive preparations that serve as semi-manufactured products generally comprise 0.0001 % by weight to 95% by weight, preferably 0.1 to 80% by weight, but in particular 1 % by weight to 50% by weight, based on the total weight of the preparation, of inventive hydroxyflavanones, their salts or their mixtures.
The inventive preparations comprising one or more of the inventive hydroxyflavanones are produced in such a manner that the inventive hydroxyflavanones are incorporated into the nutritional, nutritive or consumable preparations as the substances themselves, as solution or in the form of a mixture with a solid or liquid carrier.
To produce the preparations, in a further embodiment, the inventive hydroxyflavanones and, if appropriate, other constituents of the inventive preparation can also be incorporated in advance into emulsions, into liposomes, for example based on phosphatidylcholine, into microspheres, into nanospheres or into capsules made of a matrix suitable for foods and drinks, for example made of starch, starch derivatives, other polysaccharides, natural fats, natural waxes or proteins, for example gelatin. A further embodiment is that the inventive hydroxyflavanones are complexed in advance with suitable complexing agents, for example with cyclodextrins or cyclodextrin derivatives, preferably ~i-cyclodextrin, and are used in this form.
Other constituents which can be used for the inventive nutritional, nutritive or consumable preparations are customary bases, aids, and additives for foods and drinks, for example water, mixtures of fresh or processed, plant or animal, base substances or raw materials (for example raw, roasted/fried, dried, fermented, smoked and/or boiled meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or their mixtures), digestible or indigestible carbohydrates (for example sucrose, maltose, fructose, glucose, dextrins, amylose, amylopectin, inulin, xylan, cellulose), sugar alcohols (for example sorbitol), natural or hardened fats (for example tallow, lard, palm fat, coconut fat, hardened vegetable fat), oils (for example sunflower oil, peanut oil, corn oil, olive oil, fish oil, soya bean oil, sesame oil), fatty acids or their salts (for example potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (for example taurine), peptides, native or processed proteins (for example gelatin), enzymes (for example peptidases), nucleic acids, nucleotides, flavor enhancers (for example sodium glutamate, inositol phosphate, 2-phenoxypropionic acid), emulsifiers (for example lecithins, diacylglycerols, monoacylglycerols), stabilizers (for example caragheenan, alginate), preservatives (for example benzoic acid, sorbic acid), antioxidants (for example tocopherol, ascorbic acid), chelators (for example citric acid), organic or inorganic acidulants (for example malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid), additional bitter substances (for example quinine, caffeine, limonine), sweeteners (for example saccharin, cyclamate, aspartame, neotame), mineral salts (for example sodium chloride, potassium chloride, magnesium chloride, sodium phosphates), the substances inhibiting enzymatic browning (for example sulfur dioxide, sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or colored pigments (for example carotenoids, flavonoids, anthocyans, chlorophylls and their derivatives), spices, synthetic, natural or nature identical flavorings or fragrances and odor-correctives and taste-correctives not affecting the bitter taste.
Other constituents which can be used for the inventive oral pharmaceutical preparations are all customary further active compounds, base substances, aids and additives for oral pharmaceutical preparations.
Active compounds which can be used are all bitter- or metallic-tasting pharmaceutical compounds which can be formulated for oral preparations.
The active compounds, base substances, aids and additives can be converted into the oral dosage forms in a manner known per se. This takes place with the use of inert non-toxic pharmaceutically compatible aids.
These include, inter alia, carriers (for example microcrystalline cellulose), solvents (for example liquid polyethylene glycols), emulsifiers (for example sodium dodecyl sulfate), dispersants (for example polyvinylpyrrolidone), synthetic and natural biopolymers (for example albumin), stabilizers (for example antioxidants such as ascorbic acid), colorants (for example inorganic pigments such as iron oxides) or odor-correctives and taste-correctives not affecting the bitter taste.
Preferably, the inventive preparations can also comprise a flavoring composition to round and refine the taste and/or odor of the preparation.
Suitable flavoring compositions comprise, for example, synthetic, natural or nature identical flavorings, fragrances and taste substances and suitable aids and carriers. It is considered here to be particularly advantageous that the bitter or metallic taste impression can be suppressed or reduced by filavorings or fragrances present in the inventive flavoring compositions and thus the entire flavor or taste profile can be improved.
The invention further relates to the use of the nutritional, nutritive or consumable preparations, or pharmaceutical preparations, as semi-manufactured products for suppressing or reducing the bitter taste or aftertaste of preparations manufactured therefrom as finished products.
Finished products within the meaning of the invention are ready to use products for end consumers and are, for example, mentioned on page 5 of the specification.
Semi-finished products within the meaning of the invention are preparations, which were mixed or blended with other semi-finished food products or finished products.
EXAMPLES
The examples serve only to illustrate the invention, without restricting it thereto.
Example 1: Debittering black tea Two different types of black tea were brewed using boiling water (3 g of tea to 100 ml, allowed to infuse for 3 min, filter) and were then tasted by an expert group. The bitterness was rated using a scale of 1 to 5 (1 just perceptibly bitter, 5 very bitter). The results are shown in the table below:
Table 1 Sample Rating (1-5) Tea sample 1 3.5 Tea sample 2 5 Tea sample 2 2 + 0.05% homoeriodictyol disodium salt Example 2: Masking the bitter taste of a [i-lactam antibiotic A solution of Faropenem Daloxate ([5R-[3(R*),5a,6a(R*)]]-6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-4-this-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester, CAS No. 141702-36-5, 0.1 % by weight in water, sample 1 ) and a mixture of Faropenem Daloxate + homoeriodictyol di-sodium salt (each 0.1 % by weight in water, sample 2) were made up. A
group of 7 testers were each given 3 samples for difference testing. 4 testers received sample 1 as a duplicate sample, 3 testers received sample 2 as a duplicate sample. The samples were tasted in differing orders. Of 7 testers, 7 correctly identified the individual sample. The average bitter intensity of sample 1 was rated 5, that of sample 2 was rated 2 (scale 1 to 5).
Example 3: Reducing bitterness of a caffeine solution by (2S)-homoeriodictyol disodium salt To quantify the reduction in bitter impression, the bitterness of a 500 ppm-containing caffeine solution and a sample which contained 500 ppm of caffeine and various amounts of (2S)-homoeriodictyol disodium salt was determined.
To categorize the test samples, a reference series was prepared using 10 different concentrations of caffeine in water (50, 100, 150, 200, 250, 300, 350, 400, 450 and 500 ppm). In the diagram hefeir~aft~r, the dependence of recognition of bitterness on the amount of homoeriodictyol disodium salt added may be seen:
Fig. 1 shows the course of bitterness intensity of a solution containing 500 ppm of caffeine with increasing concentration of (2S)-homoeriodictyol disodium salt compared with a series of caffeine concentrations (100 to 500 ppm) Examale 4: Reduction in bitterness of a caffeine solution by various hydroxyflavanones Similarly to Example 3, a caffeine solution (500 ppm) with or without 100 ppm of (2S)-homoeriodictyol, (2S)-homoeriodictyol disodium salt, (2S)-eriodictyol, (2S)-eriodictyol 7-methyl ether and (2S)-naringenin was tasted and classified on the basis of the reference series.
Fig 2 shows the estimated caffeine intensity of a solution containing 500 ppm of caffeine and 100 ppm of an exemplary hydroxyflavanone.
Example 5 The bitter impressions of a paracetamol solution, a paracetamollhomoeriodictyol disodium salt solution and a solution containing paracetamol/homoeriodictyol disodium salt and chocolate flavoring were classified on a scale of 1 to 9.
Fig. 3 shows the decrease in bitter intensity for paracetamol.
Although the invention has been described in detail in the foregoing for the purpose of illustration, it is to be understood that such detail is solely for that purpose and that variations can be made therein by those skilled in the art without departing from the spirit and scope of the invention except as it may be limited by the claims.
Claims (20)
1. A preparation comprising a compound of the general formula (I) where R1 to R9 independently of one another denote hydrogen atoms, hydroxyl groups, methyl, ethyl, 1-propyl, 2-propyl, methoxy, ethoxy, 1-propyloxy or 2-propyloxy groups, with the proviso that at least one of the radicals R1 to R9 represents a hydroxyl group.
2. ~A preparation according to claim 1, containing an orally consumable product.
3. ~A preparation according to claim 1 or 2, wherein said preparation is a nutritional, nutritive, consumable or oral pharmaceutical preparation.
4. ~A preparation according to claim 1, 2 or 3, wherein in formula (I), R2, R4, R5 and R9 represent hydrogen atoms and R1, R3, R6, R7 and R8 independently of one another denote hydrogen atoms, hydroxyl groups, methyl, methoxy or ethoxy groups, with the proviso that at least one of the radicals R6 to R8 represents a hydroxyl group.
5. A preparation according to claim 1, 2 or 3 wherein in formula (I), R2, R4, R5, R8 and R9 represent hydrogen atoms and R1, R3 and R6 independently of one another denote hydrogen atoms, hydroxyl or methoxy groups, with the proviso that at least one of the radicals R1 and R3 represents a hydroxyl group, and R7 represents a hydroxyl group.
6. A preparation according to claim 1, 2 or 3 wherein said compound is selected from the group consisting of 2-(4-hydroxyphenyl)-5,7-dihydroxychroman-4-one (naringenin), 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-4-one (eriodictyol), 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychroman-4-one (eriodictyol 7-methyl ether), 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxychroman-4-one (eriodictyol 5-methyl ether) and 2-(4-hydroxy-3-methoxyphenyl)-5,7-dihydroxychroman-4-one (homoeriodictyol).
7. A preparation according to any one of claims 1 to 6, wherein said compounds of the formula (I) exist as monovalent anions or, in the case of a plurality of hydroxyl groups, as polyvalent anions, and counterions are cations with a single positive charge of the first main group and subgroup of the Periodic Table of the Elements, the ammonium ion, a trialkylammonium ion, the cations with a double charge of the second main group and subgroup of the Periodic Table of the Elements, and the trivalent cations of the 3 rd main group and subgroup of the Periodic Table of the Elements.
8. A preparation according to claim 1, 2 or 3, wherein compounds of the formula (I) exist as (2R)-enantiomers.
9. A preparation according to claim 1, 2 or 3, wherein compounds of the formula (I) exist as (2S)-enantiomers.
10. A preparation according to claim 1, 2 or 3, wherein compounds of the formula (I) exist as a mixture of (2R)- and (2S) -enantiomers.
11. A preparation according to any one of claims 1 to 10, wherein said preparation comprises 0.000001% by weight to 95% by weight, based on the total weight of the preparation, of said compound.
12. A preparation according to claim 11, wherein said preparation is a food preparation or drink preparation.
13. A preparation according to claim 11, wherein said preparation is an oral pharmaceutical preparation, and comprises 0.000001% by weight to 10% by weight, based on the total weight of the preparation, of said compounds.
14. A preparation according to claim 12, wherein said preparation is a semi-manufactured product.
15. A preparation according to claim 13, wherein said preparation is a semi-manufactured product.
16. A preparation according to claim 11, wherein said preparation is a fragrance, flavoring and taste compositions and spice mixtures.
17. A preparation according to any one of claims 1 to 13, wherein said preparation comprises at least one bitter substance wherein said compound masks or reduces the bitterness of said substance.
18. A preparation according to any one of claims 1 to 17, wherein said preparation comprises at least one further bitter-masking substance.
19. A preparation according to any one of claims 1 to 11, comprising an additional flavoring composition.
20. Use of a compound as defined in any one of claims 1 or 3 to 9, as a constituent of a nutritional, nutritive or consumable preparation, or oral pharmaceutical preparation containing at least one bitter or metallic taste impression substance or a substance causing a bitter or metallic after taste, for masking or reducing the bitter or metallic taste impression.
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| DE10122898A DE10122898A1 (en) | 2001-05-11 | 2001-05-11 | Use of 2-phenyl-4-chromanone derivatives to mask bitter or metallic tastes in foods, consumables and oral pharmaceutical products |
| DE10122898.8 | 2001-05-11 |
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| CA2385510A1 true CA2385510A1 (en) | 2002-11-11 |
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| CA002385510A Abandoned CA2385510A1 (en) | 2001-05-11 | 2002-05-08 | Use of hydroxyflavanones for masking bitter taste |
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2001
- 2001-05-11 DE DE10122898A patent/DE10122898A1/en not_active Withdrawn
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- 2002-04-29 EP EP02009275A patent/EP1258200B1/en not_active Expired - Lifetime
- 2002-04-29 ES ES02009275T patent/ES2236385T3/en not_active Expired - Lifetime
- 2002-04-29 AT AT02009275T patent/ATE289172T1/en not_active IP Right Cessation
- 2002-05-01 JP JP2002129893A patent/JP2002360188A/en active Pending
- 2002-05-08 IL IL149525A patent/IL149525A/en not_active IP Right Cessation
- 2002-05-08 CA CA002385510A patent/CA2385510A1/en not_active Abandoned
- 2002-05-08 US US10/141,426 patent/US8685436B2/en active Active
- 2002-05-09 MX MXPA02004645A patent/MXPA02004645A/en active IP Right Grant
- 2002-05-10 AU AU38273/02A patent/AU780220B2/en not_active Ceased
- 2002-05-13 BR BR0201714-8A patent/BR0201714A/en not_active Application Discontinuation
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| EP1258200A3 (en) | 2003-06-04 |
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| AU3827302A (en) | 2002-11-14 |
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| DE50202258D1 (en) | 2005-03-24 |
| IL149525A0 (en) | 2002-11-10 |
| EP1258200A2 (en) | 2002-11-20 |
| MXPA02004645A (en) | 2002-11-29 |
| US20020188019A1 (en) | 2002-12-12 |
| ATE289172T1 (en) | 2005-03-15 |
| ES2236385T3 (en) | 2005-07-16 |
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| EEER | Examination request | ||
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