IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS

Abstract

The use of compounds according to formula (I)

##STR00001##

and with X, Y═—NH— or —O—, wherein at least X or Y is —NH—,
in the form of any one of its stereoisomers or a mixture thereof, wherein
is indicating a carbon-carbon single or double bond, and wherein one carbon-carbon double bond is present either at C2 or C3,
the wavy bond is indicating an unspecified configuration of the adjacent double bond, as umami tastant.

Claims

1. A method of using at least one compound according to formula (I): ##STR00010## wherein R is independently selected from the group consisting of ##STR00011## and wherein X, Y are independently —NH— or —O—, wherein at least one of X or Y is —NH—, in the form of any one of its stereoisomers or a mixture thereof, wherein indicates a carbon-carbon single or double bond, and wherein one carbon-carbon double bond is present either at C2 or C3, and wherein the wavy bond indicates an unspecified configuration of the adjacent double bond, as an ingredient to confer, enhance, improve, or modify the umami taste of a consumable composition.

2. The method according to claim 1, wherein the at least one compound according to formula (I) is further defined by formula (II): ##STR00012## wherein R is independently selected from the group consisting of ##STR00013## in the form of any one of its stereoisomers or a mixture thereof, and wherein the wavy bond indicates an unspecified configuration of the adjacent double bond, as an ingredient to confer, enhance, improve, or modify the umami taste of a consumable composition.

3. The method according to claim 1, wherein the at least one compound according to formula (I) is selected from the group consisting of (E)-N-(4-cinnamamidobutyl)-2-methylbut-2-enamide, (E)-N-(4-((E)-3-(4-methoxyphenyl)acrylamido)butyl)-2-methylbut-2-enamide, (E)-4-methoxy-N-(4-(2-methylbut-2-enamido)butyl)benzamide, 4-cinnamamidobutyl (E)-2-methylbut-2-enoate, 4-cinnamamidobutyl 2-methylbut-3-enoate, and 4-((E)-2-methylbut-2-enamido)butyl cinnamate.

4. An umami flavour composition comprising: (i) at least one compound according to formula (I) as defined in claim 1; and (ii) one or more further flavour ingredients.

5. The umami flavour composition according to claim 4, wherein the at least one compound according to formula (I) is selected from the group consisting of (E)-N-(4-cinnamamidobutyl)-2-methylbut-2-enamide, (E)-N-(4-((E)-3-(4-methoxyphenyl)acrylamido)butyl)-2-methylbut-2-enamide, (E)-4-methoxy-N-(4-(2-methylbut-2-enamido)butyl)benzamide, 4-cinnamamidobutyl (E)-2-methylbut-2-enoate, 4-cinnamamidobutyl 2-methylbut-3-enoate, and 4-((E)-2-methylbut-2-enamido)butyl cinnamate.

6. A consumable composition comprising: (i) at least one compound according to formula (I) as defined in claim 1; and (ii) a product base.

7. A method of providing a consumable composition having umami taste, comprising the step of adding at least one compound according to formula (I): ##STR00014## wherein R is independently selected from the group consisting of ##STR00015## and wherein X, Y are independently —NH— or —O—, wherein at least one of X or Y is —NH—, in the form of any one of its stereoisomers or a mixture thereof, wherein indicates a carbon-carbon single or double bond, with the proviso that one of the dotted lines is representing a double bond while the other is representing a single bond, and wherein the wavy bond indicates an unspecified configuration of the adjacent double bond, to the consumable composition.

8. A compound according to formula (I) ##STR00016## wherein R is independently selected from the group consisting of ##STR00017## and wherein X, Y are independently —NH— or —O—, wherein at least one of X or Y is —NH—, in the form of any one of its stereoisomers or a mixture thereof, wherein indicates a carbon-carbon single or double bond, and wherein one carbon-carbon double bond is present either at C2 or C3, and wherein the wavy bond indicates an unspecified configuration of the adjacent double bond, with the proviso that the compound is not (E)-N-(4-cinnamamidobutyl)-2-methylbut-2-enamide.

9. The compound according to formula (I) as defined in claim 8, selected from the group consisting of (E)-N-(4-((E)-3-(4-methoxyphenyl)acrylamido)butyl)-2-methylbut-2-enamide, (E)-4-methoxy-N-(4-(2-methylbut-2-enamido)butyl)benzamide, 4-cinnamamidobutyl (E)-2-methylbut-2-enoate, 4-cinnamamidobutyl 2-methylbut-3-enoate, and 4-((E)-2-methylbut-2-enamido)butyl cinnamate.

10. A consumable composition comprising: (i) the umami flavour composition as defined in claim 4; and (ii) a product base.

11. A consumable composition comprising: (i) the umami flavour composition as defined in claim 5; and (ii) a product base.

12. The umami flavour composition of claim 4, wherein the at least one compound according to formula (I) comprises about 0.001 to about 100% by weight of the umami flavour composition.

13. The consumable composition of claim 6, wherein the at least one compound according to formula (I) comprises between 0.01 ppm and 10000 ppm by weight of the consumable composition.

14. An umami flavour composition comprising: (i) at least one compound according to formula (II) as defined in claim 2; and (ii) one or more further flavour ingredients.

15. The umami flavour composition according to claim 14, wherein the at least one compound according to formula (II) is selected from the group consisting of (E)-N-(4-cinnamamidobutyl)-2-methylbut-2-enamide, (E)-N-(4-((E)-3-(4-methoxyphenyl)acrylamido)butyl)-2-methylbut-2-enamide, (E)-4-methoxy-N-(4-(2-methylbut-2-enamido)butyl)benzamide, 4-cinnamamidobutyl (E)-2-methylbut-2-enoate, 4-cinnamamidobutyl 2-methylbut-3-enoate, and 4-((E)-2-methylbut-2-enamido)butyl cinnamate.

16. The umami flavour composition of claim 14, wherein the at least one compound according to formula (II) comprises about 0.001% to about 100% by weight of the umami flavour composition.

17. A consumable composition comprising: (i) at least one compound according to formula (II), as defined in claim 2; and (ii) a product base.

18. The consumable composition of claim 17, wherein the at least one compound according to formula (II) comprises between 0.01 ppm and 10000 ppm by weight of the consumable composition.

19. A consumable composition comprising: (i) the umami flavour composition as defined in claim 14; and (ii) a product base.

20. A consumable composition comprising: (i) the umami flavour composition as defined in claim 15; and (ii) a product base.

Description

EXAMPLES

Example 1: Synthesis of (E)-N-(4-cinnamamidobutyl)-2-methylbut-2-enamide (Ia)

[0047] ##STR00005##

1a) tert-butyl (4-cinnamamidobutyl)carbamate (1)

[0048] A solution of cinnamoyl chloride (4.21 g, 25.3 mmol) in dichloromethane (50 ml) was added dropwise to a solution of tert-butyl (4-aminobutyl)carbamate (5 g, 26.6 mmol) and triethylamine (3.07 g, 30.4 mmol) in dichloromethane (200 ml) cooled with an ice bath. After 2 hours stirring at room temperature, the reaction mixture was washed successively with 1M HCl (2×100 ml), saturated NaHCO.sub.3 (100 ml) and H.sub.2O (100 ml). The organic phase was dried over MgSO.sub.4, filtered and concentrated. The obtained solid was washed with MTBE/pentane and then dried in vacuum oven at 40° C. 7.5 g (93%) of tert-butyl (4-cinnamamidobutyl)carbamate (1) was yielded as white powder.

[0049] Purity is >95% by NMR analysis.

[0050] 1H NMR (600 MHz, DMSO-d6) δ=1.15-1.58 (m, 13H), 2.82-3.00 (m, 2H), 3.08-3.23 (m, 2H), 6.55-6.70 (m, 1H), 6.77-6.92 (m, 1H), 7.29-7.47 (m, 4H), 7.49-7.66 (m, 2H), 8.03-8.32 (m, 1H) ppm.

[0051] 13C NMR (151 MHz, DMSO-d6) δ=26.74, 27.26, 28.44, 38.61, 39.65, 77.52, 122.48, 127.63, 129.10, 129.54, 135.11, 138.55, 155.77, 164.96 ppm.

[0052] 1b) N-(4-aminobutyl)cinnamamide (2):

[0053] TFA (4.84 ml, 62.8 mmol) was added to a solution of tert-butyl (4-cinnamamidobutyl)carbamate (1) (2 g, 6.28 mmol) in dichloromethane (100 ml). After 2 hours stirring at room temperature, the volatiles were removed at reduced pressure (till 20 mbar) at 50° C. The intermediate N-(4-aminobutyl)cinnamamide (2, N-(4-aminobutyl)-3-phenyl-prop-2-enamide) was obtained as a viscous yellow oil, which is used in the next step 1c) without any further purification.

1c) (E)-N-(4-cinnamamidobutyl)-2-methylbut-2-enamide (Ia)

[0054] The intermediate N-(4-aminobutyl)cinnamamide (2) was dissolved in dichloromethane. To the resulted solution, triethylamine (5.25 ml, 37.7 mmol) was added while stirring at room temperature. Then, a solution of (E)-2-methylbut-2-enoyl chloride (1.043 g, 8.79 mmol) in dichloromethane (10 ml) was added dropwise. Stirring was continued for two hours, and then the solution was allowed to stand at room temperature overnight. The next day, the solution was diluted with dichloromethane (100 ml) and then washed successively with diluted hydrochloric acid solution (2×100 ml) and saturated potassium carbonate solution (2×100 ml). The organic layer was separated, dried over MgSO.sub.4, filtered and concentrated.

[0055] The obtained solid was dried in vacuum oven at 50° C./20 mbar.

[0056] 1.5 g (78%) of (E)-N-(4-cinnamamidobutyl)-2-methylbut-2-enamide (Ia) was yielded as a white solid.

[0057] Purity is ca. 98% by NMR analysis,

[0058] 1H NMR (600 MHz, DMSO-d6) δ=1.33-1.51 (m, 4H), 1.44 (s, 1H), 1.45 (s, 1H), 1.62-1.77 (m, 6H), 1.68 (s, 1H), 1.72 (s, 1H), 2.96-3.25 (m, 4H), 3.10 (s, 1H), 3.17 (s, 1H), 6.13-6.38 (m, 1H), 6.29 (s, 1H), 6.50-6.71 (m, 1H), 6.61 (s, 1H), 7.22-7.47 (m, 1H), 7.34-7.43 (m, 2H), 7.41 (s, 1H), 7.50-7.64 (m, 2H), 7.55 (s, 1H), 7.69-7.80 (m, 1H), 7.75 (s, 1H), 8.01-8.36 (m, 1H), 8.12 (s, 1H) ppm.

[0059] 13C NMR (151 MHz, DMSO-d6) δ=12.41, 13.63, 26.73, 26.79, 38.50, 38.57, 122.34, 127.48, 128.84, 128.96, 129.40, 132.05, 134 97, 138.41, 164.81, 168.31 ppm.

Example 2: Synthesis of (E)-N-(4-((E)-3-(4-methoxyphenyl)acrylamido)butyl)-2-methylbut-2-enamide (1b)

[0060] ##STR00006##

2a) tert-butyl (E)-(4-(2-methylbut-2-enamido)butyl)carbamate (3, N-Boc-N′-tiglyl-putrescine)

[0061] (E)-2-methylbut-2-enoyl chloride (3.19 g, 26.9 mmol) was added dropwise to a solution of tert-butyl (4-aminobutyl)carbamate (4.6 g, 24.43 mmol) and triethylamine (5 g, 49.4 mmol) in dichloromethane (200 mi) cooled with an ice bath. The resulted solution was stirred at room temperature for 2 hours then washed successively with 1M HCl (2×100 ml), saturated NaHCO.sub.3 (100 ml) and H.sub.2O (100 ml). The organic was dried with MgSO.sub.4, filtered and concentrated. The solid was washed with pentane and then dried in vacuum oven at 40° C. 6.1 g (92%) of tert-butyl (E)-(4-(2-methylbut-2-enamido)butyl)carbamate (3) was yielded as off white solid.

[0062] Purity is >95% by NMR analysis.

2b) (E)-N-(4-aminobutyl)-2-methylbut-2-enamide (4, N-mono-tiglyl-putrescine)

[0063] TFA (8.55 ml, 111 mmol) was added dropwise to solution of tert-butyl (E)-(4-(2-methylbut-2-enamido)butyl)carbamate (3) (3 g, 11.10 mmol) in dichloro-methane (50 mi) to give a colorless solution. After 1 hour stirring at room temperature, the solution was concentrated under re-duced pressure (till 20 mbar) at 50° C. The intermediate (E)-N-(4-aminobutyl)-2-methylbut-2-enamide (4) was obtained as a viscous yellow oil, which is used in the next step 2c without any further purification.

2c) (E)-N-(4-((E)-3-(4-methoxyphenyl)acrylamido)butyl)-2-methylbut-2-enamide (Ib)

[0064] The intermediate (E)-N-(4-aminobutyl)-2-methylbut-2-enamide (4) was dissolved in dichloromethane (150 ml). To the resulted solution, triethylamine (13.47 g, 133 mmol) was added while stirring at room temperature. Then, a solution of ((E)-3-(4-methoxyphenyl)acryloyl chloride (2.62 g, 13.31 mmol) in dichloromethane (20 ml) was added dropwise. Stirring was continued for two hours and then the solution allowed to stand at room temperature overnight. The next day, the solution was diluted with dichloromethane (100 ml) and washed successively with 1M HCl (3×150 ml), saturated NaHCO.sub.3 (2×150 ml) and H.sub.2O (150 ml) The organic layer was dried over MgSO.sub.4, filtered and concentrated to obtain 3.3 g of off white solid with a purity of ca. 80% by NMR analysis.

[0065] Purification by a silica gel column using DCM/ethyl acetate followed by recrystallization from ethanol resulted in 1.5 g (41%) of (E)-N-(4-((E)-3-(4-methoxyphenyl)acrylamido)butyl)-2-methylbut-2-enamide (Ib) as white solid.

[0066] Purity is >98% by NMR analysis.

[0067] 1H NMR (600 MHz, DMSO-d6) δ=1.35-1.50 (m, 4H), 1.43 (s, 1H), 1.44 (s, 1H), 1.60-1.77 (m, 6H), 1.67 (s, 1H), 1.72 (s, 1H), 3.00-3.21 (m, 4H), 3.10 (s, 1H), 3.15 (s, 1H), 3.70-3.85 (m, 3H), 3.78 (s, 1H), 6.17-6.36 (m, 1H), 6.27 (s, 1H), 6.41-6.56 (m, 1H), 6.96 (d, J=8.95 Hz, 2H), 7.21-7.43 (m, 1H), 7.43-7.56 (m, 2H), 7.48 (s, 1H), 7.60-7.82 (m, 1H), 7.74 (s, 1H), 7.89-8.17 (m, 1H), 8.01 (s, 1H) ppm.

[0068] 13C NMR (151 MHz, DMSO-d6) δ=12.41, 13.63, 26.79, 38.46, 38.59, 55.26, 114.38, 119.85, 127.52, 129.03, 132.05, 138.11, 160.25, 165.12, 168.32 ppm.

Example 3: Synthesis of (E)-4-methoxy-N-(4-(2-methylbut-2-enamido)butyl)benzamide (Ic)

[0069] ##STR00007##

[0070] 3a) The intermediate (E)-N-(4-aminobutyl)-2-methylbut-2-enamide (4) obtained from step 2b) of Example 2 was dissolved in dichloromethane (150 ml). To the resulted solution, trimethylamine (4.04 g, 39.9 mmol) was added while stirring at room temperature. Then, a solution of 4-methoxybenzoyl chloride (0.7 g, 4.10 mmol) in dichloromethane (20 ml) was added dropwise. Stirring was continued for two hours and then the solution was allowed to stand at room temperature overnight. The next day, the solution was diluted with dichloromethane (100 ml) and washed successively with 1M HCl (2×150 ml), saturated NaHCO (2×150 ml) and H.sub.2O (150 ml), The organic layer was dried over MgSO.sub.4, filtered and concentrated to obtain a slight yellow solid, which was recrystallized from ethyl acetate, washed with ether and dried in vacuum oven at 50° C., 0.8 g (79%) of (E)-4-methoxy-N-(4-(2-methylbut-2-enamido)butyl)benzamide (Ic) was yielded as white powder.

[0071] Purity is >95% by NMR analysis.

[0072] 1H NMR (600 MHz, DMSO-d6) δ=1.29-1.54 (m, 4H), 1.61-1.74 (m, 6H), 3.03-3.16 (m, 2H), 3.18-3.28 (m, 2H), 3.73-3.86 (m, 3H), 5.82-6.50 (m, 1H), 6.79-7.08 (m, 2H), 7.59-7.92 (m, 3H), 8.21-8.43 (m, 1H) ppm.

[0073] 13C NMR (151 MHz, DMSO-d6) δ=12.55, 13.76, 26.96, 38.50, 38.77, 55.47, 113.55, 127.02, 128.97, 129.07, 132.18, 161.53, 165.68, 168.42 ppm.

Example 4: Synthesis of a mixture of 4-cinnamamidobutyl (E)-2-methylbut-2-enoate (Id) and 4-cinnamamidobutyl 2-methylbut-3-enoate (Ie) (1:2)

4a) N-(4-hydroxybutyl)cinnamamide (5)

[0074] ##STR00008##

[0075] In a 250 mL round-bottomed flask 4-aminobutan-1-ol (3.21 g, 36.0 mmol) and triethylamine (9.20 ml, 66.0 mmol) in dichloromethane (100 ml) were provided. Cinnamoyl chloride (5 g, 30.0 mmol) in 10 mL of dichloromethane was added dropwise while cooling with an ice/water bath. The cooling bath was removed, and stirring was continued for 2 hours at room temperature. The reaction mixture was diluted with dichloromethane and washed with a diluted hydrochloric acid solution. The organic layer was separated and washed with a saturated sodiumbicarbonate solution and brine. The organic layer was dried and evaporated to yield 4.5 g (67%) of N-(4-hydroxybutyl)cinnamamide (5) as an oil.

[0076] Purity is >95% by NMR analysis.

[0077] 1H NMR (600 MHz, DMSO-d6) δ=1.35-1.55 (m, 4H), 3.09-3.25 (m, 2H), 3.36-3.58 (m, 2H), 4.43 (t, 1H), 6.61-6.64 (d, 1H), 7.32-7.43 (m, 4H), 7.54-7.56 (d, 2H), 8.11 (br t, 1H) ppm.

[0078] 13C NMR (151 MHz, DMSO-d6) δ=25.89, 30.00, 38.63, 60.45, 122.38, 127.49, 128.97, 129.40, 134.99, 138.40, 164.81 ppm.

4b) 4-cinnamamidobutyl (E)-2-methylbut-2-enoate (Id) and 4-cinnamamidobutyl 2-methylbut-3-enoate (Ie)

[0079] N-(4-hydroxybutyl)cinnamamide (5) (1 g, 4.56 mmol) was dissolved in dichloromethane (25 ml). Triethylamine (1.271 ml, 9.12 mmol) was added while stirring. Then (E)-2-methylbut-2-enoyl chloride (0.595 g, 5.02 mmol) was added dropwise while stirring. The exothermic reaction started to reflux. Stirring was continued for three hours at room temperature. The reaction mixture was diluted with ether and washed with a diluted hydrochloric acid solution. The organic layer was separated and washed with a saturated sodiumbicarbonate solution, dried and concentrated. The residue was purified by flash column chromatography. Eluent dichloromethane/methanol from 0 to 3% methanol.

[0080] 0.7 g of product Id and Ie (51%) was obtained in a ratio of 1:2.

[0081] 1H NMR (600 MHz, DMSO-d6) δ=1.16-1.20 (m, 3H), 1.45-1.56 (m, 3H), 1.57-1.67 (m, 3H), 1.74-1.78 (m, 3H), 3.16-3.23 (m, 4H), 4.03-4.07 (m, 2H), 4.07-4.11 (m, 1H) 5.06-5.17 (m, 2H), 5.84-5.92 (m, 1H), 6.59-6.64 (m, 1H), 6.74-6.81 (m, 1H), 7.35-7.39 (m, 2H), 7.39-7.41 (m, 2H), 7.41-7.44 (m, 3H), 7.53-7.59 (m, 3H), 8.04-8.21 (m, 51H) ppm.

[0082] 13C NMR (151 MHz, DMSO-d6) δ=12.50, 14.70, 18.90, 26.18, 26.24, 26.32, 38.73, 38.78, 40.56, 43.28, 64.23, 64.37, 116.48, 122.78, 128.01, 129.47, 129.92, 135.46, 137.67, 137.86, 139.00, 165.36, 174.09 ppm.

Example 5: Synthesis of 4-((E)-2-methylbut-2-enamido)butyl cinnamate (If)

[0083] ##STR00009##

5a) (E)-N-(4-hydroxybutyl)-2-methylbut-2-enamide (6)

[0084] 4-aminobutan-1-ol (3.01 g, 33.7 mmol) was dissolved in dichloromethane (50 ml). Triethylamine (4.70 ml, 33.7 mmol) was added while stirring. The solution was cooled with an ice/water bath and (E)-2-methylbut-2-enoyl chloride (2 g, 16.87 mmol) was added dropwise. The cooling bath was removed and stirring was continued for three hours at room temperature. The reaction mixture was diluted with dichloromethane and washed with a diluted hydrochloric acid solution. The organic layer was separated and washed with a potassiumcarbonate solution, dried and concentrated. The residue was purified by flash column chromatography. Eluent DCM/methanol from 0 to 3% methanol. 1 g of an oil was obtained.

[0085] Purity is >95% by NMR analysis.

[0086] 1H NMR (600 MHz, DMSO-d6) δ=1.28-1.51 (m, 4H), 1.62-1.70 (d, 3H), 1.74 (s, 3H), 3.00-3.13 (m, 2H), 3.36-3.40 (m, 2H), 4.30-4.36 (t, 1H), 6.25-6.30 (q, 1H), 7.59-7.86 (br t, 1H) ppm.

[0087] 13C NMR (151 MHz, DMSO-d6) δ=12.41, 13.62, 25.90, 30.02, 38.79, 60.54, 128.74, 132.11, 168.28 ppm.

5b) 4-((E)-2-methylbut-2-enamido)butyl cinnamate (If)

[0088] To (E)-N-(4-hydroxybutyl)-2-methylbut-2-enamide (6, 1 g, 5.84 mmol) was added cinnamoyl chloride (0.973 g, 5.84 mmol). The reaction mixture was stirred at 60° C. for three hours. Then it was heated at 100° C. for a short time. The crude was purified by flash column chromatography, eluent DCM/methanol with 1% methanol to yield 1.5 g of a colorless oil.

[0089] 1H NMR (600 MHz, DMSO-d6) δ=1.39-1.77 (m, 10H), 3.05-3.22 (q, 2H), 4.08-4.21 (t, 2H), 6.18-6.38 (q, 1H), 6.59-6.71 (d, 1H), 7.29-7.50 (m, 3H), 7.62-7.82 (m, 4H) ppm.

[0090] 13C NMR (151 MHz, DMSO-d6) δ=12.54, 13.75, 25.88, 30.86, 38.53, 63.98, 118.24, 128 34, 128.54, 129.08, 130.63, 132.17, 134.18, 144.62, 165.43, 168.48 ppm.

Example 6: Taste Evaluation—Comparison with MSG

[0091] An aqueous NaCl solution (0.5% by weight) was prepared. To this base was added:

[0092] a) 30 ppm of the compound Ia (sample 8a);

[0093] b) 200 ppm of MSG (sample 6b, benchmark).

[0094] The tastes of the two samples 6a and 6b have been evaluated by 5 trained panellists. They were asked to rate the intensity of sample 6a as difference to sample 6b and to describe the overall effect. Typically, the following descriptors are used to describe the effect: umami, salty, bitter, overall sweet.

[0095] The taste of sample 6a was described as umami, brothy and longlasting. The umami on bitter level was marked as a little higher than benchmark. Overall, sample 6a was preferred over sample 6b.

Example 7: Taste Evaluation—Comparison with Further Derivatives

[0096] An aqueous NaCl solution (0.5% by weight) was prepared. To this base was added:

[0097] a) 20 ppm of the compound Ia (sample 7a);

[0098] b) 20 ppm of the compound Ib (sample 7b):

[0099] c) 20 ppm of the compound Ic (sample 7c).

[0100] The tastes of the three samples 7a, 7b and 7c have been evaluated by 5 trained panellists.

[0101] The taste of sample 7b was described as more umami, stronger and more lingering, more sweet, but having an off note, animalic, floral sweet in comparison to sample 7a.

[0102] The taste of sample 7c was described as more umami and cleaner umami than sample 7a.

Example 8: Taste Evaluation of Amide Ester Analogues

[0103] An aqueous solution of NaCl (0.5% by weight) and MSG (0.05% by weight) was prepared.

[0104] To this base was added:

[0105] a) 20 ppm of the mixture of the compound (Id+Ie) in a ratio 1:2 (sample 8a);

[0106] b) 20 ppm of the compound if (sample 8b).

[0107] A group of four experienced tasters compared the samples 8a and 8b with the pure base.

[0108] Unanimously the group found that sample 8a was more umami than the base Additionally some bitterness was perceived.

[0109] Unanimously the group found that sample 8b was more umami than the base. The tasting was described as a pleasant taste experience.