SUGAR-DIPEPTIDE CONJUGATES AS FLAVOR MOLECULES

Abstract

The present invention relates to compounds and compositions for use in enhancing flavor and umami taste of food products. Particularly, the present invention relates to compounds of the general formula (I) and compositions comprising them.

##STR00001##

Claims

1. Compound of the general formula I, ##STR00003## wherein R1 is selected from the group consisting of a hydrogen, a C.sub.1, a C.sub.2, a C.sub.3, a C.sub.4 alkyl group and a salt of the compound.

2. The compound according to claim 1, wherein R1 is selected from the group consisting of a hydrogen, a methyl group, and a salt of the compound.

3. The compound according to claim 1 which is 1-Deoxy-D-fructosyl-N-β-alanyl-L-glycine.

4. A composition comprising a compound of the general formula I, ##STR00004## wherein R1 is selected from the group consisting of a hydrogen, a C.sub.1, a C.sub.2, a C.sub.3, a C.sub.4 alkyl group and a salt of the compound in an amount of at least 1 mg/g.

5. The composition according to claim 4, wherein the composition is an extract from plant and/or meat material.

6. The composition according to claim 4, wherein the composition is the result of a flavor reaction.

7. The composition according to claim 4, wherein the composition is food grade.

8. The composition according to claim 4, wherein the composition is selected from the group consisting of a culinary seasoning, a cooking aid, a sauce or soup concentrate, a dry and a wet pet-food product.

9-12. (canceled)

13. Method for enhancing the flavor and/or umami taste of a culinary food product, comprising the step of adding a compound comprising the general formula I, ##STR00005## wherein R1 is selected from the group consisting of a hydrogen, a C.sub.1, a C.sub.2, a C.sub.3, a C.sub.4 alkyl group and a salt of the compound to the culinary food product.

14. The method according to claim 13, wherein the final concentration of the compound in the food product is at least 1 mg/g.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0014] The present invention pertains to a compound of the general formula I), wherein R1 is a hydrogen, a C.sub.1, a C.sub.2, or a C.sub.3 alkyl group; or a salt of said compound. In one embodiment, the R1 group of the compound of the present invention is a hydrogen. The chemical name of the corresponding compound is: 1-deoxy-D-fructosyl-N-β-alanyl-L-glycine.

[0015] A second aspect of the invention relates to a composition comprising said compound of the general formula I) in an amount of at least 1 mg/g, at least 1.4 mg/g, at least 1.7 mg/g, at least 2 mg/g, at least 2.5 mg/g, at least 3 mg/g, at least 3.5 mg/g, or at least 5 mg/g of the total composition.

[0016] In one embodiment, the composition of the present invention is an extract from plant and/or meat material. For example, the composition is an extract from beef meat, chicken meat, pork meat or a combination thereof.

[0017] In another embodiment, the composition of the present invention is the result of a flavor reaction. The term “flavor reaction” refers herein to a chemical reaction occurring between at least one reducing sugar and at least one amino acid or protein. Typically, this chemical reaction occurs during a heating process and is typically also referred to as Maillard reaction. In one example, the flavor reaction is a Maillard reaction.

[0018] In a preferred embodiment, the composition of the present invention is food grade. Under “food grade” the inventors mean that the composition is suitable for human consumption, for example directly, in concentrated form, and/or when used diluted in a food product.

[0019] For example, the composition of the present invention is selected from the group consisting of a culinary seasoning product, a cooking aid, a sauce or soup concentrate, a dry or wet pet-food product.

[0020] Further aspects of the present invention relate to a use of said compound for enhancing the flavor and/or the umami taste of a food product. Such a food product may be a ready-to-eat food product. It may also be a flavor concentrate used for seasoning a still further other food product. Advantageously, the compound of the present invention may be used for being added to a seasoning, a cooking aid or a food concentrate product. Thereby the strength of providing an umami taste to a still further food product is improved in such a seasoning, cooking aid or food concentrate product.

[0021] Further aspects of the present invention also relate to a use of a composition comprising said compound in an amount of at least 1 mg/g, at least 1.4 mg/g, at least 1.7 mg/g, at least 2 mg/g, at least 2.5 mg/g, at least 3 mg/g, at least 3.5 mg/g, or at least 5 mg/g of the total composition, for enhancing the flavor and/or the umami taste of a food product.

[0022] Advantageously, such a food product may be a ready-to-eat food product. The use of the present invention has the advantage that it allows to use natural extracts which for example have been enriched in said compounds for flavoring and improving the natural umami taste of those food products.

[0023] A still further aspect of the present invention is a method for enhancing the flavor and/or umami taste of a culinary food product, comprising the step of adding said compound or the composition comprising said compound to a food product. The food product can be a ready-to-eat food product or a flavor concentrate.

[0024] As an example of the present invention, the final concentration of said compound in the food product is at least 1 mg/g, at least 1.4 mg/g, at least 1.7 mg/g, at least 2 mg/g, at least 2.5 mg/g, at least 3 mg/g, at least 3.5 mg/g, or at least 5 mg/g of the composition. This advantageously, allows generating for example food seasoning products and flavor concentrate products which convey a strong umami taste to a further food product upon application.

[0025] Those skilled in the art will understand that they can freely combine all features of the present invention disclosed herein. In particular, features described for the products of the present invention may be combined with the uses and method of the present invention, and vice versa. Further, features described for different embodiments of the present invention may be combined.

[0026] Further advantages and features of the present invention are apparent from the figures and examples.

Example 1: Synthesis of 1-deoxy-D-fructosyl-N-β-alanyl-L-glycine from Glucose and β-alanyl-L-glycine

[0027] Chemicals: Sodium bisulphite and glycerol were purchased from Sigma, glucose from SDfine Chemicals, β-alanylglycine from Aksci, methanol and acetic acid from Merck. All commercially available reagents were used as received, from their respective suppliers.

[0028] .sup.1H NMR (360.13 MHz) and .sup.13C NMR (90.56 MHz) spectra were recorder on a Bruker DPX-360 spectrometer equipped with a broadband multinuclear z-gradient probehead. The chemical shifts (in ppm) were expressed with respect to an internal reference (TMS or TSP). Multiplicities are reported as follows: s=singlet, d=doublet, t=triplet, q=quatruplet, m=multiplet, bs=broad singlet.

[0029] D-Glucose (23 g, 127.37 mmol, 2.8 eq) and sodium bisulfite (1.6 g, 12.389 mmol, 0.28 eq.) were suspended in methanol (38 mL) and glycerol (19 mL). After stirring for 30 min at 100° C., β-alanine-L-glycine (6.7 g, 45.48 mmol, 1.0 eq.) and acetic acid (5.1 mL) were added and the resulting mixture was heated for 3.5 hours at 100° C. Reaction mass was then cooled down and diluted with water (38 mL). The reaction mixture was purified using a column packed in Amberlite IRN-77 ion exchange resin (100 g). NH.sub.3 0-0.4% was used as gradient in water for elution. Finally, 5 g 1-deoxy-D-fructosyl-N-β-alanyl-L-glycine was obtained (23.62%).

[0030] LC-MS (ESI.sup.+): m/z 309.22 (100, [M+H].sup.−); .sup.1H NMR (400 MHz, 300 K, Deuterium Oxide) δ 2.80 [t, J=6.5 Hz, 2H], 3.29-3.36 [m, 2H], 3.42 [t, J=6.5 Hz, 2H], 3.72-3.77 [m, 2H], 3.78 [s, 2H], 3.89 [dd, J=3.4, 9.8 Hz, 1H], 3.99-4.05 [m, 2H]. .sup.13C NMR (100 MHz, 300 K, Deuterium Oxide) δ 30.40, 43.18, 44.51, 53.04, 63.96, 68.85, 69.26, 69.77, 95.28, 172.13, 176.62.

Example 2: Sensory Evaluation of β-Alanyl-L-Glycine in Model Broth

[0031] The sensory tests were performed in a sensory panel room at 20-25° C. To avoid a retro-nasal aroma or taste impression, nose clips were used. The sensory panel consisted of 8 to 14 trained persons. The panel was trained to evaluate the taste of aqueous solutions (1 mL each) of the following standard taste compounds by using a triangle test: saccharose (50 mmol/L) and L-alanine (15 mmol/L), respectively, for sweet taste; lactic acid (20 mmol/L) for sour taste; NaCl (12 mmol/L) for salty taste; caffeine (1 mmol/L) and quinine hydrochloride (0.05 mmol/L), respectively, for bitter taste; sodium glutamate (8 mmol/L, pH 5.7) for umami taste; and tannin (0.05%) for astringency. The “white meaty” oral sensations was assessed in a model broth solution prepared from monosodium glutamate monohydrate (1.9 g/L), yeast extract (2.1 g/L), maltodextrin (6.375 g/L) and sodium chloride (2.9 g/L) in bottled water (pH 5.9).

[0032] The taste threshold concentration of β-alanyl-L-glycine was determined in model broth and was found to be 18,400 μmol/L (2.6 mg/g) for the thick-sour sensation and white-meaty oral impression.

Example 3: Sensory Evaluation of 1-deoxy-D-fructosyl-N-β-alanyl-L-glycine in Model Broth

[0033] The taste threshold concentration of 1-deoxy-D-fructosyl-N-β-alanyl-L-glycine was determined in model broth as described in Example 2 and was found to be 4,620 μmol/L (1.4 mg/g) for the thick-sour sensation and white-meaty oral impression under the same experimental model system (see Example 2). In fact, it corresponds to a lowering of the taste threshold molar concentration by a factor of about 4.

[0034] This result means that about a 4-time smaller amount of molecules of 1-deoxy-D-fructosyl-N-β-alanyl-L-glycine is required to impart a same corresponding taste impact of flavour and umami taste enhancement in a food product than with the corresponding β-alanyl-L-glycine under the same conditions.

Example 4: Seasoning Compositions

[0035] Chicken soups were prepared by dissolving 6 g chicken base powder (detailed recipe shown in Table 1) and 1 g monosodium glutamate in 500 mL hot water. 1-Deoxy-D-fructosyl-N-β-alanyl-L-glycine was added at 2 g/L.

TABLE-US-00001 TABLE 1 Composition of chicken base powder Ingredient Quantity (%) Chicken Meat powder 30 Starch 1.52 Flavors 2.58 Celery powder 0.50 Garlic powder 0.90 Chicken fat 8.00 Maltodextrine 56.50 Total 100

[0036] The sensory evaluation was carried out by 12 panelists, previously screened for their sensory abilities. The panelists were asked to taste a set of 2 chicken soups, one containing no 1-Deoxy-D-fructosyl-N-β-alanyl-L-glycine and one containing 1-Deoxy-D-fructosyl-N-β-alanyl-L-glycine at 2 g/L. If sensory differences were observed, the panelists were asked to describe them.

[0037] The sensory panel concluded that chicken soups with and without the 1-Deoxy-D-fructosyl-N-β-alanyl-L-glycine were perceived as significantly different and the addition of 1-Deoxy-D-fructosyl-N-β-alanyl-L-glycine increased the spicy, savory and meaty flavours.

Example 5: Seasoning Compositions

[0038] Tomato soups were prepared by dissolving in 6 g tomato base powder (detailed recipe shown in the Table 2) in 500 mL hot water. 1-Deoxy-D-fructosyl-N-β-alanyl-L-glycine was added at 2 g/L.

TABLE-US-00002 TABLE 2 Composition of tomato soup powder Ingredient Quantity (g) Yeast extract 0.036 White Sugar 0.348 Flavors 0.629 Tomato powder 0.03 Wheat flour 0.562 Corn starch 0.247 Guar gum 0.012 Spices powder 0.071 Maltodextrine 0.038 Sunflower oil 0.022 Total 2

[0039] The sensory panel concluded that tomato soups with and without the 1-Deoxy-D-fructosyl-N-β-alanyl-L-glycine were perceived as significantly different and the addition of 1-deoxy-D-fructosyl-N-β-alanine increased the savory, fatty and spicy notes.