Use of rubusoside for reducing or suppressing certain unpleasant taste impressions

Abstract

The invention relates to the use of rubusoside and certain mixtures containing rubusoside, preferably the use of certain rubusoside-containing mixtures, in particular Rubus suavissimus extracts, for masking, reducing or suppressing a bitter, sour and/or astringent taste impression. The invention further relates to orally consumable preparations, comprising at least one bitter, sour and/or astringent-tasting substance and rubusoside or certain rubusoside-containing mixtures, preferably certain Rubus suavissimus extracts, a corresponding method of producing said preparations and a method for reducing or suppressing the bitter, sour and/or astringent effect of a bitter, sour and/or astringent-tasting substance. The invention further relates to certain flavoring compositions that are particularly effective for masking, reducing or suppressing a bitter, sour and/or astringent taste impression.

Claims

1. A method for masking the sour and/or astringent taste of chlorogenic acid or isomers thereof, wherein the method is consisting of: adding to said chlorogenic acid or isomers thereof, an amount of rubusoside that does not bring about a sweet taste impression that is greater than a sweet taste impression of a 1.5 wt. % aqueous sucrose solution, thereby masking sour and/or astringent taste of the chlorogenic acid or isomers thereof.

2. A method for masking the sour and/or astringent taste of chlorogenic acid or isomers thereof, wherein the method is consisting of: adding to said chlorogenic acid or isomers thereof an extract of Rubus suavissimus in an amount that does not bring about a sweet taste impression that is greater than a sweet taste impression of a 1.5 wt. % aqueous sucrose solution, thereby masking sour and/or astringent taste of the chlorogenic acid or isomers thereof.

3. The method of claim 2, wherein said extract of Rubus suavissimus contains rubusosides and polyphenols.

4. The method of claim 3, wherein said extract contains polyphenols selected from the group consisting of ellagic acid, gallic acid and flavonoids and mixtures thereof.

5. The method of claim 4, wherein said flavonoids are selected from the group consisting of rutin and isoquercitrin and mixtures thereof.

6. The method of claim 2, wherein said extract of Rubus suavissimus comprises (a) rubusosides in an amount from 0.1 to 50 wt. % and (b) one or more phenolic compounds in a total amount in the range from 0.1 to 25 wt. %.

7. The method of claim 2, wherein said extract of Rubus suavissimus is obtained by a method comprising: (a) obtaining a primary extract from leaves using an extractant at a temperature in a range from 0° C. up to the boiling point of the extractant at normal pressure, (b) optionally concentrating the primary extract, (c) obtaining a secondary extract by treating the primary extract, (d) drying of the secondary extract, and (e) optionally mixing the dried secondary extract with a diluent or a mixture of two or more diluents.

Description

EXAMPLES

(1) Unless stated otherwise, all data refer to weight.

Example 1: Analytical Composition of a Rubus suavissimus Extract with 22.6 wt. % Rubusoside, Dissolved in Glycerol, to be Used According to the Invention

(2) TABLE-US-00001 CAS-No. Name Wt. % 64849-39-4 Rubusoside 22.6% 476-66-4 Ellagic acid 0.22% Glucose  0.1% Water 29.8% Glycerol 30.5% Proteins, total  1.3% Free sugars, total  4.6% Total content of phenols  5.7% (according to Folin-Ciocalteu; including ellagic acid and other polyphenols) Unknown substances To 100%

Example of Application 1: Suppression of Bitter Taste with Rubusoside or a Rubus suavissimus Extract

(3) To quantify the reduction of the bitter impression, the bitterness of the bitter substance in solution in water and of a sample that contained bitter substance and the amount of the test compound or of the extract (test substance) stated in each case was determined by a group of experts (classification 0 [not bitter] to 10 [extremely bitter]). Evaluation was carried out as calculation of the reduction (in %) of the bitter impression from the average values of the assessments of the bitter substance solution or the bitter substance and examples of solutions containing the test substance.

(4) TABLE-US-00002 Bitter impression % (1-10) Reduction a) without b) with of the Bitter test test bitter Test substance substance substance substance impression 60 ppm 500 ppm 5.2 4.1 21% Rubus suavissimus caffeine extract from Example 1 60 ppm 0.5% Rubus suavissimus potassium 4.8 4.4  9% extract from Example 1 chloride

Example of Application 2: Flavoring Compositions

(5) TABLE-US-00003 Flavoring composition (amount used, wt. %) Ingredient A B C D E F G H Rubus suavissimus 5 40 17.5 32.5 40 extract, from Example 1 Rubus suavissimus 10 65 35 extract, dry containing 10% rubusoside Homoeriodictyol 5 2.5 Eriodictyol 2.5 Phloretin 1 Hesperetin 0.5 10 wt. % trans-pellitorin 0.25 0.25 0.5 0.25 (e.g. according to WO 2004/043906) in 1,2-propylene glycol/diethylmalonate Extract from 2.5 2.5 2.5 Hydrangea macrophylla according to U.S. Provisional Application 61/237,866 (Symrise) and EP 2 298 084 A1, containing phyllodulcin Jambul oleoresin, containing 0.1 0.1 30 wt. % spilanthol in 1,2-propylene glycol (Robertet) 1,2-Propylene glycol — 20 — to 100 to 100 20 to 100 — Glycerol — to 100 — 20 20 to 100 20 — Maltodextrin to 100 — to 100 — — — — to 100

(6) The substances or solutions are mixed in the proportions stated above and are then taken up in 1,2-propylene glycol and/or glycerol and are dissolved completely by gentle heating or mixed homogeneously with the solid vehicles.

Example of Application 3: Spray-Dried Flavoring Compositions

(7) TABLE-US-00004 Flavoring composition (amount used in wt. %) Ingredient A B C D E F G H Maltodextrin from wheat 24.3 24.3 24.3 24.3 24.3 24.3 24.3 24.3 Gum arabic 6.1 6.1 6.1 6.1 6.1 6.1 6.1 6.1 Rubus suavissimus 10 10 8 10 8 10 12 12 extract, liquid, containing 20% rubusoside Trans-pellitorin according 0.02 0.02 0.01 0.02 0.01 0.01 0.02 0.03 to WO 2004/043906 Homoeriodictyol, sodium salt 1 1 1.2 2 Hesperetin 0.2 Phloretin 0.4 Drinking water to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100

(8) The drinking water is placed in a container and the maltodextrin and the gum arabic are dissolved in it. Then the constituents are emulsified using a mixer (Ultra Turrax) in the solution of vehicle described above. The temperature of the resultant mixture should not exceed 30° C. The mixture is then spray-dried (required inlet temperature: 185-195° C., required outlet temperature: 70-75° C.). The spray-dried semi-finished product contains approx. 18-22% of the flavoring compositions.

(9) Spray-dried preparations can also be produced similarly with other flavoring compositions according to the invention or to be used according to the invention.

Example of Application 4: Use of the Flavoring Compositions in Orally Consumable Preparations

(10) TABLE-US-00005 Preparation (amount used in wt. %) A B C D E F Yogurt 0.1% fat 99.9 Yogurt 1.5% fat 99.9 Orange juice 99.9 99.9 Green-tea 99.8 99.85 beverage Flavoring 0.1 0.1 composition 2E Flavoring 0.1 0.1 composition 2F Flavoring 0.2 composition 3B Flavoring 0.15 composition 3G

(11) The flavored samples A, B, E and F show a reduced sour impression relative to the unflavored base. The flavored samples C and D have, relative to the unflavored samples, a greatly reduced perception of bitterness and in the case of the yogurts and of the orange juice, of sourness and astringency, without an increase in sweetness.

Example of Application 5: Flavoring Compositions for Masking a Bitter and Astringent Taste

(12) TABLE-US-00006 Flavoring composition (amount used in wt. %) Ingredient A B C D E F G H I J K L Symrise cream flavor in 0.8 1 1 1,2-propylene glycol Symrise spring herbs 5 2.5 flavor, spray-dried Symrise soya-masking flavor 10 in 1,2-propylene glycol Symrise soya-masking flavor, 10 spray-dried Symrise juice intensifying flavor 10 5 Symrise orange flavor 2.5 Rubus suavissimus 35 40 80 extract, dry, containing 10% rubusoside Rubus suavissimus 40 17.5 5 17.5 32.5 40 extract, liquid, containing rubusoside from Example 1 Homoeriodictyol, sodium salt 2.5 Hesperetin 0.5 0.5 0.5 10 wt. % pellitorin 0.25 0.25 0.5 (e.g. according to WO 2004/043906) in 1,2-propylene glycol/diethylmalonate Glycerol to 100 to 100 to 100 to 100 to 100 to 100 1,2-Propylene glycol 20 30 30 20 20 30 Maltodextrin — to 100 to 100 to 100 to 100

(13) The substances or solutions are mixed in the proportions stated above and then taken up in propylene glycol and/or glycerol and are dissolved completely with gentle heating or mixed homogeneously with the solid vehicles.

Example of Application 6: Reduction of Astringent and Sour Impression

(14) The following products, in each case without and with a flavoring composition, were assessed by a panel of trained tasters. The astringent impression and sour impression were assessed on a scale from 1 (not perceptible) to 9 (very strong) and averaged for the tasters.

(15) TABLE-US-00007 Astringent Sour impression impression (0-9) (0-9) a) a) Orally without b) with without b) with consumable test test test test preparation Test substance substance substance substance substance Yogurt 0.1% fat 0.1% of flavoring 4.5 3 6 4 composition from Example of application 5C Yogurt 0.1% fat 0.1% of flavoring 4.5 2 6 3 composition from Example of application 5D Yogurt 0.1% fat 10 mg/kg rubusoside 5 5 7 5.5 Soya yogurt 0.1% of flavoring 7 5 4 2 2.7% fat composition from Example of application 5F Soya yogurt 0.1% of flavoring 7 4.5 4 2 2.7% fat composition from Example of application 5E Yogurt 0.1% fat 10 mg/kg rubusoside 5 5 7 5.5

Example of Application 7: Reduction of the Bitter and Sour Impression

(16) The following products, in each case without and with a flavoring composition, were assessed by a panel of trained tasters. The bitter impression (only in the case of orange juice) and the sour impression were assessed on a scale from 1 (not perceptible) to 9 (very strong) and averaged over the tasters.

(17) TABLE-US-00008 Bitter impression Sour impression (0-9) (0-9) a) a) Orally without b) with without b) with consumable test test test test preparation Test substance substance substance substance substance Orange direct 0.1% of flavoring 4.5 3 6 4 juice composition from Example of application 5A Pineapple direct 0.1% of flavoring n.a. n.a. 4 3 juice composition from Example of application 5I Salad dressing 0.2% of flavoring (water-oil based) composition from Example of application n.a. n.a. 7 5.5 5G n.a. = not assessed