Use of certain hydroxybenzoic acid amides for masking unpleasant taste impressions

Abstract

The present invention relates primarily to the use of certain hydroxybenzoic acid amides or the salts or mixtures thereof for masking an unpleasant taste impression, preferably of a bitter, adstringent, dusty, dry, floury, rancid, metallic and/or cardboard taste or aftertaste, of one or more unpleasant-tasting peptides or of certain amino acid mixtures. The invention further relates to a corresponding method for masking unpleasant taste impressions and to novel preparations.

Claims

1. A composition comprising: (i) 0.0001 to 0.5 wt. %, relative to the total weight of the composition, of 2,4-Dihydroxy-N-[(4-hydroxy-3-methoxy-phenyl)methyllbenzamide (compound 1), a salt thereof, or a mixture thereof; and (ii) 0.001 to 10 wt. %, relative to the total weight of YPFP (SEQ ID NO: 82), WWW, or a combination thereof; provided that the amount of component (i) is sufficient to mask an unpleasant taste impression of component (ii), compared to an otherwise identical comparative composition not comprising component (i).

2. The composition of claim 1, further comprising: (iii) one or more additional substances not of formula (I) that mask an unpleasant taste impression.

Description

EXAMPLES

Example 1: Effect of 2,4-Dihydroxy-N-[(4-hydroxy-3-methoxy-phenyl)methyl]benzamide (Compound 1),5,7-Dihydroxy-3-[(4-hydroxy-3-methoxy-phenyl)methyl]-1,3-benzoxazin-2,4-dione (Compound 2), 4-Hydroxy-N-[(4-hydroxy-3-methoxy-phenyl)methyl]benzamide (Compound 3), 2-Hydroxy-N-[(4-hydroxy-3-methoxy-phenyl)methyl]benzamide (Compound 4) and N-[(4-hydroxy-3-methoxy-phenyl)methyl]-2,4-dimethoxy-benzamide (Compound 5, Comparative Example) on the Bitterness of a Mixture of Amino Acids

(1) The masking effect of hydroxybenzoic acid amides (compounds 1-4) to be preferably used according to the invention as well as a comparative substance (compound 5) on a mixture of bitter amino acids (2 g/l L-Isoleucine; 3.5 g/l L-Leucine; 1 g/l L-Phenylalanine; 0.7 g/l L-Tryptophan in water) was evaluated by an panel of experts (n=13) (Evaluation 0 [not bitter] up to 10 [extremely bitter]). The tasting was performed with a nose clip, to exclude olfactory influences, and in a randomized duo-test. The bitterness of the mixture of amino acids was evaluated by the panel by 4.980,31 on a scale from 0 to 10.

(2) TABLE-US-00001 Reduction of Bitter taste Bitter taste bitterness in % amino amino acid compared to the acid mixture + mixture of amino Sample mixture sample acids 100 ppm 2,4-Dihydroxy- 5.27 3.90 25.9 N-[(4-hydroxy-3-methoxy- phenyl)methyl]benzamide (compound 1) 100 ppm 5,7-Dihydroxy-3- 4.59 3.20 30.3 [(4-hydroxy-3-methoxy- phenyl)methyl]-1,3- benzoxazin-2,4-dione (compound 2) 100 ppm 4-Hydroxy-N-[(4- 4.82 4.11 14.1 hydroxy-3-methoxy- phenyl)methyl]benzamide (compound 3) 100 ppm 2-Hydroxy-N-[(4- 5.13 4.74 7.7 hydroxy-3-methoxy- phenyl)methyl]benzamide (compound 4) 100 ppm N-[(4-hydroxy-3- 5.59 6.86 22.8 methoxy-phenyl)methyl]- 2,4-dimethoxy-benzamide (compound 5, comparative example)

Example 2: Effect of 2,4-Dihydroxy-N-[(4-hydroxy-3-methoxy-phenyl)methyl]benzamide (Compound 1) and N-[(4-hydroxy-3-methoxy-phenyl)methyl]-2,4-dimethoxy-benzamide (Compound 5, Comparative Example) on the Bitter Taste of Peptides

(3) The masking effect of 2,4-Dihydroxy-N-[(4-hydroxy-3-methoxy-phenyl)methyl]benzamide (compound 1) and N-[(4-hydroxy-3-methoxy-phenyl)methyl]-2,4-dimethoxy-benzamide (compound 5) on the bitter taste of peptides was examined in a panel of experts (n=15) in randomized duo-tests. Therefore, solutions of bitter peptides in water with or without the addition of the exemplary substances were tasted and the perceived bitter taste was evaluated on a scale from 0 (not bitter) to 10 (extremely bitter).

(4) With compound 1, a clear reduction of the bitterness could be achieved for a plurality of peptides (with the exception of the dipeptide Leu-Trp (confirmation of the data of Ley et al. (Ley et al., J Agr Food Chem 54, 8574-8579 (2006)) as well as the tripeptide Glu-Leu-Leu, which are added as comparative examples here). Compound 5 ((additional) comparative example) was not able to achieve a reduction of the bitterness for any of the peptides. For some, compound 5 even increased the bitter taste.

(5) TABLE-US-00002 Bitter taste Bitter taste Reduction of peptide peptide bitterness solution + Reduction of solution + compound 5 Bitter taste 100 ppm bitterness 100 ppm (%) Peptide (compound compound 1 (compound (comparative Peptide solution 1) (%) 5) example) Arg-Pro 1.85 1.47 20.9 2.05 10.81 0.1% (w/v) Trp-Trp-Trp 6.47 5.35 17.4 6.40 1.08 0.01% (w/v) Tyr-Pro-Phe- 4.48 3.43 23.3 4.68 4.46 Pro 0.1% (w/v) Leu-Trp 6.8 6.5 4 7.1 4.41 0.2% (w/v) (comparative example) Glu-Leu-Leu 5.3 5.1 3.77 5.6 5.66 0.2% (w/v) (comparative example)

Example 3: Effect of 2,4-Dihydroxy-N-[(4-hydroxy-3-methoxy-phenyl)methyl]benzamide (Compound 1) on the Bitter Taste of a Solution of Whey Protein Hydrolysate

(6) The bitter masking effect of 2,4-dihydroxy-N-[(4-hydroxy-3-methoxy-phenyl)methyl]benzamide (compound 1) on the bitter taste of whey protein hydrolysate was tested in a panel of experts [n=8] for a solution of 3% (w/v) of a commercially available whey protein hydrolysate (BioZate 3 of the company Davisco) in randomized duo-tests. The perceived bitter taste was evaluated on a scale from 0 [not bitter] to 10 [extremely bitter]. For comparison, a combination of compound 1 with a usual bitter masking aroma was tested, to examine possible additive effects.

(7) TABLE-US-00003 Reduction of the bitter Sample taste [%] Base [whey protein hydrolysate 0 (3% (w/v) in water)] Base + 100 ppm compound 1 24.5 Base + bitter masking aroma 65.5 (Symrise) (1.6% (w/v)) + 100 ppm compound 1

Application Example 1: Spray Dried Preparation as Semi-Finished Product for Aromatizing Finished Products According to the Invention

(8) TABLE-US-00004 Ingredient Use in wt.-% Drinking water 60.8% Maltodextrin of wheat 24.3% Gum Arabic 6.1% 2,4-Dihydroxy-N-[(4-hydroxy-3-methoxy- 8.8% phenyl)methyl]benzamide (compound 1)

(9) The drinking water is provided in a container and the maltodextrin and Gum Arabic are dissolved therein. Subsequently, the 2,4-dihydroxy-N-[(4-hydroxy-3-methoxy-phenyl)methyl]benzamide (compound 1) is emulsified into the carrier solution with a turrax. The temperature of the spray solution should not exceed 30 C. The mixture is then spray dried (required temperature entering: 185-195 C., required temperature exit: 70-75 C.).

(10) The spray dried semi-finished product contains approx. 19-22% of compound 1 and can be used for the production of a preparation according to the invention as described herein.

Application Example 2: Use in a Soy Drink

(11) The compound 2,4-Dihydroxybenzoicacid-N-(4-hydroxy-3-methoxybenzyl)amide (compound 1) was pre-dissolved in ethanol and added to a soy milk from a local supermarket, which contains unpleasant tasting substances according to claim 1. The mixture was stirred in the beaker with the milk aroma.

(12) TABLE-US-00005 Ingredient Use in wt.-% Soy milk (local supermarket, contains in average 99.8% approx . . . 15% free amino acids) Milk aroma (Symrise) 0.1% 10% 2,4-Dihydroxybenzoicacid-N-(4-hydroxy-3- 0.1% methontbenzyl)amide (compound 1) in ethanol

Application Example 3: Use in a Soy Drink in Combination with -Amino Butyric Acid

(13) -amino butyric acid was pre-dissolved in water and 2,4-Dihydroxybenzoicacid-N-(4-hydroxy-3-methoxybenzyl)amide in ethanol and added to a soy milk from a local supermarket, which contains unpleasant tasting substances according to claim 1, according to the table (mixtures A-C). The mixtures were stirred in the beaker together with the milk aroma.

(14) TABLE-US-00006 Use in wt.-% Ingredient A B C Soy milk (local supermarket) add to add to add to 100% 100% 100% Milk aroma (Symrise) 0.1% 0.1% 0.1% 10% 2,4-Dihydroxybenzoicacid-N-(4- 0.1% 0.1% hydroxy-3-methoxybenzyl)amide in ethanol 1% amino butyric acid in water 0.1%

(15) Compared to mixture B, the mixtures A and C were clearly less bitter. Additionally, in mixture A, the astringency and the beany taste were clearly reduced.

Application Example 4: Whey Protein Drink

(16) Production of a fruit whey protein drink according to the following recipe with subsequent homogenization and pasteurization.

(17) TABLE-US-00007 Use in wt.-% Ingredient A B Whey protein isolate (min. 88% protein TS, 8% 8% contains unpleasant tasting substances according to claim 1) Fruit juice concentrate mixture (mango, 10% 10% banana, carrot, orange) Citric acid 50% 0.2% 0.2% Pectin 0.4% 0.4% Vitamin-mixture 0.01% 0.01% Mineral salt-mixture 1% 1% 10% 2,4-Dihydroxybenzoicacid-N-(4- 0.1% hydroxy-3-methoxybenzyl)amide in ethanol Mango aroma (Symrise) 0.05% 0.05% Drinking water Add to 100% Add to 100%

(18) Compared to the comparative mixture A, mixture B was clearly less bitter.

Application Example 5: Highly Protein Containing Drink (Sports Nutrition)

(19) The dry ingredients are mixed and subsequently dissolved in drinking water. In example C, the 10% solution of the 2,4-Dihydroxybenzoesure-N-(4-hydroxy-3-methoxybenzyl)amide is added and stirred.

(20) TABLE-US-00008 Use in wt.-% Ingredient A B C Whey protein isolate (min. 88% 8% 8% 8% protein TS, contains unpleasant tasting substances according to claim 1) Mixture of amino acids (45% 1% 1% 1% L-Leucine; 30% L-Valine, 25% L-Isoleucine) Citric acid 0.1% 0.1% 0.1% Sucralose 0.007% 0.007% 0.007% Orange dry aroma (Symrise) 0.1% 0.1% 0.1% Bitter masking dry aroma 1.6% 1.6% (Symrise) 10% 2,4-Dihydroxybenzoicacid-N- 0.1% (4-hydroxy-3-methoxybenzyl)amide in ethanol Drinking water Add to Add to Add to 100% 100% 100%

(21) Compared to the comparative mixture A, the mixtures B and C are less bitter. Further, mixture C is clearly less bitter than mixture B.

Application Example 6: Dietary Foodstuff for Special Medical Purposes (FSMP)

(22) Production of a UHT-drink according to the recipe below.

(23) TABLE-US-00009 Use in wt.-% Ingredient A B Whey protein concentrate (min. 80% 12% 12% protein TS, contains unpleasant tasting substances according to claim 1) Drinking water Add to 100% Add to 100% Glucose syrup 10% 10% Vegetable oils 4% 4% Sucrose 2% 2% Maltodextrin 1.5% 1.5% Vitamin-mixture 0.05% 0.05% Mineral salt-mixture 2% 2% Vanilla aroma (Symrise) 0.2% 0.2% Lecithin 0.1% 0.1% Citric acid 0.05% 0.05% 10% 2,4-Dihydroxybenzoicacid-N-(4- 0.1% hydroxy-3-methoxybenzyl)amide in ethanol

(24) Mixture B is clearly less bitter and drying in the aftertaste compared to comparative mixture A.

Application Example 7: Protein Bar

(25) The cereals and the whey protein isolate are mixed. A syrup is cooked from the remaining ingredients (without aroma and 2,4-Dihydroxybenzoicacid-N-(4-hydroxy-3-methoxybenzyl)amide). At the end of the cooking time, the aroma or, respectively, the 10% solution 2,4-Dihydroxybenzoicacid-N-(4-hydroxy-3-methoxybenzyl)amide in ethanol is added. The syrup is mixed with the cereals and formed into bars.

(26) TABLE-US-00010 Use in wt.-% Ingredient A B C Oat flakes 13% 13% 13% Rice-Crispies 14% 14% 14% Corn Flakes 10% 10% 10% Whey protein isolate (min. 88% protein TS, 10% 10% 10% contains unpleasant tasting substances according to claim 1) Glucose Syrup 0.1% 0.1% 0.1% Sucrose 12% 12% 12% Glycerine 1% 1% 1% Salt 0.2% 0.2% 0.2% Drinking water 13.5% 13.5% 13.5% Vegetable fat 10% 10% 10% Lecithin 0.2% 0.2% 0.2% Bitter masking aroma (Symrise) 0.3% Caramel aroma (Symrise) 0.1% 0.1% 0.1% 10% 2,4-Dihydroxybenzoicacid-N-(4- 0.1% 0.1% hydroxy-3-methoxybenzyl)amide in ethanol

(27) Compared to the comparative mixture A, mixtures B and C are less bitter. Additionally, mixture C is clearly less drying and astringent in the aftertaste compared to mixture B.

Application Example 8: Highly Protein Containing Milk Product (Quark)

(28) 2,4-Dihydroxybenzoicacid-N-(4-hydroxy-3-methoxybenzyl)amide is pre-solved in ethanol and added while stirring into quark with the cream aroma. In the comparative mixture, only the cream aroma is added while stirring.

(29) TABLE-US-00011 Use in wt.-% Ingredient A B C Highly protein containing market Add to Add to Add to product (contains unpleasant tasting 100% 100% 100% substances according to claim 1); (French market) (9% protein, 2.9% fat) Sucrose 4% 4% 4% Cream aroma (Symrise) 0.15% 0.15% 0.15% 10% 2,4-Dihydroxybenzoicacid-N-(4- 0.05% 0.1% hydroxy-3-methoxybenzyl)amide in ethanol

(30) Compared to mixture A, mixtures B and C were clearly less bitter and astringent. In mixture C, the astringency was even more clearly reduced.