TASTE MODIFIERS COMPRISING A CHLOROGENIC ACID

Abstract

A consumable comprising an ingredient or ingredients that cause an off-taste in the consumable, and a chlorogenic acid provided in a concentration sufficient to mask or modify the off-taste. The chlorogenic acid may be supplied as an extract from a botanical source obtained by extraction at 30-80° C. with water and/or a polar organic solvent. The method of making an off-taste by addition of a chlorogenic acid to a consumable is also claimed.

Claims

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22. A consumable comprising a steviol derivative which imparts an off-taste to the consumable, and a chlorogenic acid present the consumable in a concentration of 0.0001%.sup.w/v to 0.1%.sup.w/v.

23. The consumable according to claim 22, wherein the off-taste is a bitter aftertaste or is a metallic off-taste.

24. The consumable according to claim 22, wherein the chlorogenic acid is derived from green coffee bean extract.

25. The consumable according to claim 24, wherein the chlorogenic acid is derived from an extract of green robusta coffee beans.

26. The consumable of claim 22, wherein the consumable is selected from the group consisting of: cereal products, rice products, tapioca products, sago products, baker's products, biscuit products, pastry products, bread products, confectionery products, desert products, gums, chewing gums, chocolates, ices, honey products, treacle products, yeast products, baking-powder, salt and spice products, savory products, mustard products, vinegar products, sauces (condiments), tobacco products, cigars, cigarettes, processed foods, cooked fruits and vegetable products, meat and meat products, jellies, jams, fruit sauces, egg products, milk and dairy products, cheese products, butter and butter substitute products, milk substitute products, edible oils and fat products, medicaments, beverages, alcoholic drinks, beers, soft drinks, mineral and aerated waters and other non-alcoholic drinks, fruit drinks, fruit juices, coffee, artificial coffee, tea, cocoa, including forms requiring reconstitution, food extracts, plant extracts, meat extracts, condiments, sweeteners, nutraceuticals, gelatins, pharmaceutical and non-pharmaceutical gums, tablets, lozenges, drops, emulsions, elixirs, syrups and other preparations for making beverages, and combinations thereof.

27. The consumable according to claim 22 containing chlorogenic acid at a concentration of about 0.001%.sup.w/v to about 0.1%.sup.w/v.

28. The consumable according to claim 22, wherein the consumable is carbonated, and in which the concentration of chlorogenic acid is about 0.0005%.sup.w/v to about 0.05%.sup.w/v.

29. The consumable according to claim 22 wherein the chlorogenic acid is selected from the group consisting of 3-CQA, 4-CQA, 5-CQA, 3-FQA, 4-FQA, 5-FQA, 3-p-CoQA, 4-p-CoQA, 5-p-CoQA, 3,4-diCQA, 3,5-diCQA, 4,5-diCQA, 3,4-CFQA, 3,5-CFQA, 4,5-CFQA, or combinations thereof.

30. A consumable according to claim 29 wherein the chlorogenic acid comprises at least two of: 3-CQA, 4-CQA, 5-CQA, 3-FQA, 4-FQA, 5-FQA, 3-p-CoQA, 4-p-CoQA, 5-p-CoQA, 3,4-diCQA, 3,5-diCQA, 4,5-diCQA, 3,4-CFQA, 3,5-CFQA, 4,5-CFQA.

31. A consumable according to claim 30 wherein the chlorogenic acid comprises at least three of: 3-CQA, 4-CQA, 5-CQA, 3-FQA, 4-FQA, 5-FQA, 3-p-CoQA, 4-p-CoQA, 5-p-CoQA, 3,4-diCQA, 3,5-diCQA, 4,5-diCQA, 3,4-CFQA, 3,5-CFQA, 4,5-CFQA.

32. A taste-modifying composition comprising a chlorogenic acid which is effective in counteracting off-tastes imparted by a steviol derivative present in a consumable, when the chlorogenic acid is present in a concentration of about 0.001%.sup.w/v to about 0.1%.sup.w/v in the consumable.

33. The consumable according to claim 32, wherein the off-taste is a bitter aftertaste or is a metallic off-taste.

34. The taste-modifying composition of claim 32, wherein the chlorogenic acid is derived from green coffee bean extract.

35. The taste-modifying composition of claim 34, wherein the chlorogenic acid is derived from an extract of green robusta coffee beans.

36. A taste-modifying composition of claim 34, wherein the chlorogenic acid is selected from the group consisting of: 3-CQA, 4-CQA, 5-CQA, 3-FQA, 4-FQA, 5-FQA, 3-p-CoQA, 4-p-CoQA, 5-p-CoQA, 3,4-diCQA, 3,5-diCQA, 4,5-diCQA, 3,4-CFQA, 3,5-CFQA, 4,5-CFQA, or combinations thereof.

37.

36. A method for modifying the taste of a consumable comprising: adding chlorogenic acid to the consumable in a concentration of about 0.001%.sup.w/v to about 0.1%.sup.w/v which amount modifies or masks a bitter aftertaste imparted by a steviol derivative also present in the consumable.

37. The method of claim 36, wherein the off-taste is a bitter aftertaste or is a metallic off-taste.

38. The method of claim 36, wherein the consumable is derived from green coffee bean extract.

39. The method of claim 38, wherein the chlorogenic acid is derived from an extract of green robusta coffee beans.

40. A method according to claim 36, wherein the chlorogenic acid is selected from the group consisting of: 3-CQA, 4-CQA, 5-CQA, 3-FQA, 4-FQA, 5-FQA, 3-p-CoQA, 4-p-CoQA, 5-p-CoQA, 3,4-diCQA, 3,5-diCQA, 4,5-diCQA, 3,4-CFQA, 3,5-CFQA, 4,5-CFQA, or combinations thereof.

41. A method according to claim 40, wherein the chlorogenic acid comprises at least two of: 3-CQA, 4-CQA, 5-CQA, 3-FQA, 4-FQA, 5-FQA, 3-p-CoQA, 4-p-CoQA, 5-p-CoQA, 3,4-diCQA, 3,5-diCQA, 4,5-diCQA, 3,4-CFQA, 3,5-CFQA, 4,5-CFQA.

42. A method according to claim 41, wherein the chlorogenic acid comprises at least three of: 3-CQA, 4-CQA, 5-CQA, 3-FQA, 4-FQA, 5-FQA, 3-p-CoQA, 4-p-CoQA, 5-p-CoQA, 3,4-diCQA, 3,5-diCQA, 4,5-diCQA, 3,4-CFQA, 3,5-CFQA, 4,5-CFQA.

Description

EXAMPLE 1

Extraction and Purification by Precipitation

[0042] Whole green robusta coffee beans (21.8 kg) are extracted with a water and ethanol (95%) mixture at a ratio of 85/15 w/w. The beans are loaded in a conical-shaped extractor and the solvent is circulated at 60° C. for 16 hours. The extract is collected by draining from the extractor and the residual beans are extracted with fresh solvent of the same composition for two more times. The amount of solvent used for each extraction is between 2 to 4.5 times of the bean weight. The extracts are combined and concentrated to 36.3 kg. An amount of ethanol equal to the extract weight is added to induce the precipitation of protein and other insoluble material in the extract. The precipitation is discarded and the supernatant is collected by filtration and further concentrated to 9.8 kg. The concentrated extract is spray-dried without addition of carrier to form a tan-colored powder. For every kilogram of green coffee bean, 146 gram of powder is obtained. The powder is water-soluble, it forms a clear solution in water. The chlorogenic acid content is analyzed by HPLC. The analysis reveals the presence of several different types of chlorogenic acid, which amount to about 35% of the total mass of the extract. The proportions of the various types of chlorogenic acid separated by HPLC and quantitated as a weight per weight percentage are shown in the table below.

TABLE-US-00002 Total 3-CQA 4-CQA 5-CQA FQAs di-CQAs FCQAs Chlorogenic (% w/w) (% w/w) (%w/w) (% w/w) (% w/w) (% w/w) acid 5.71 5.63 11.52 5.07 5.92 1.24 35.09

EXAMPLE 2

Extraction and Purification by Washing (Phase Separation)

[0043] Whole green Robusta coffee beans (22.7 kg) are extracted with a water and ethanol (95%) mixture at ratio of 40/60 w/w. The beans are loaded in a conical-shaped extractor and the solvent is circulated at 60 C for 16 hours. The extract is collected by draining from the extractor and the residual beans are extracted with fresh solvent of the same composition for two more times. The amount of solvent used for each extraction is between 2 to 4.5 times of the bean weight. The extracts are combined and partially concentrated to 64.9 kg. The extract is washed with an equal weight of ethyl acetate/ethanol mixture (85/15 w/w) once. The ethyl acetate layer is collected and subsequently discarded. The aqueous layer is collected and dried under vacuum to a tan-colored powder. For every kilogram of green coffee bean, 178 gram of powder is obtained. The powder is water-soluble; it forms a clear solution in water. The chlorogenic acid was analyzed by HPLC and the results are summarized as follows.

TABLE-US-00003 Total 3-CQA 4-CQA 5-CQA FQAs di-CQAs FCQAs Chlorogenic (% w/w) (% w/w) (%w/w) (% w/w) (Y? w/w) (% w/w) acid 2.40 3.57 20.17 5.62 7.69 1.43 40.88

EXAMPLE 3

Extraction and Purification by Microfiltration

[0044] Whole green Robusta coffee beans (22.7 kg) are extracted with a water and ethanol (95%) mixture at ratio of 40/60 w/w. The beans are loaded in a conical-shaped extractor and the solvent is circulated at 60 C for 16 hours. The extract is collected by draining from the extractor and the residual beans are extracted with fresh solvent of the same composition for two more times. The amount of solvent used for each extraction is between 2 to 4.5 times of the bean weight. The extracts are combined and partially concentrated to 64.9 kg. An aliquot of 6.8 kg of the extract is passed through a microfilter with a molecular cut-off value at 10,000 Da. The materials retained by the filter are discarded and the materials that permeate through the filter are concentrated and dried. For every kilogram of green coffee bean, 146 grams of a tan-colored powder are obtained. The powder is water-soluble; it forms a clear solution in water. The chlorogenic acid is analyzed by HPLC and the results are summarized as follows.

TABLE-US-00004 Total 3-CQA 4-CQA 5-CQA FQAs di-CQAs FCQAs Chlorogenic (% w/w) (% w/w) (%w/w) (% w/w) (% w/w) (% w/w) acid 2.22 3.81 22.33 5.84 8.53 1.56 44.30

EXAMPLE 4

Extraction and Purification by Chromatography (Adsorption Resin)

[0045] Whole green Robusta coffee beans (66.7 kg) are loaded in a conical-shaped extractor and water is circulated at 80° C. for 16 hours. The extract is collected by draining from the extractor and the residual beans are extracted with water for two more times. The amount of water used for each extraction is between 2 to 4.5 times of the bean weight. The extracts are combined and concentrated to 102.1 kg. An aliquot of 200 g of the extract is further concentrated to 120 g and loaded on a column filled with Amberlite XAD-4 adsorption resin (wet mesh size 20-60). The column is 4 cm in diameter and 38 cm long with a column bed volume of 427 ml. The column is eluted with 6 bed volumes of water followed by 4.3 bed volumes of ethanol/water (50/50 w/w). The last 2 bed volumes of the ethanol/water (50/50 w/w) elution are collected and dried to a light tan-colored powder. For every kilogram of green coffee bean, 62 grams of powder are obtained. The powder is water-soluble; it forms a clear solution in water. The chlorogenic acid was analyzed by HPLC and the results are summarized as follows.

TABLE-US-00005 Total 3-CQA 4-CQA 5-CQA FQAs di-CQAs FCQAs Chlorogenic (% w/w) (% w/w) (% w/w) (% w/w) (% w/w) (% w/w) acid 4.90 11.39 21.17 9.48 11.27 0.67 58.88

EXAMPLE 5

Extraction and Removal of Precipitate by Centrifugation/Filtration

[0046] About 4.0 kg of green Robusta coffee beans are mixed with constant agitation in 16.0 kg of water at 80° C. for at least four hours. The extract is collected either by decanting, centrifuging, or filtering. The beans are then extracted with an additional 6 kg of water at 80° C. for at least another four hours. The extracts are combined and the water is evaporated by vacuum to concentrate the extract to about 5 or 6 kg. An amount of ethanol (95%) equal to one and one-half times the weight of the concentrated extract is added; the amount of ethanol may be increased to about four times the weight of the concentrated extract if a higher content of chlorogenic acid in the final extract is desired. The mixture is stirred for 15 minutes, and the slurry is allowed to stand at ambient temperature for at least one hour. The resulting precipitate is removed by either centrifugation or filtration and is subsequently discarded. The ethanol is evaporated from the supernatant or filtrate under vacuum, and the aqueous solution is dried under vacuum to yield about 460-500 g of a tan-colored powder. Alternatively, the aqueous solution may be concentrated to an appropriate solid content of about 30% to 45% of the total weight, followed by spray-drying the concentrated aqueous solution to a tan colored powder. The powdered extract is soluble in water. It forms a clear solution in water. The chlorogenic acid is analyzed by HPLC and the results are summarized as follows.

TABLE-US-00006 Total 3-CQA 4-CQA 5-CQA FQAs di-CQAs FCQAs Chlorogenic (% w/w) (% w/w) (% w/w) (% w/w) (% w/w) (% w/w) acid 8.6 8.4 16.7 8.9 5.8 3.0 51.4

[0047] In all the examples, the extract is analyzed by high performance liquid chromatography (HPLC) using a Prodigy ODS-3 column (150×4.6 mm, particle size 5 μm) (Phenomenex, Torrance, Calif.) at ambient temperature, interfaced with a mass spectroscopic detector (MSD) to measure chlorogenic acid. The gradient used for elution of the compounds is given in Table 2.

TABLE-US-00007 TABLE 2 Time Flow Rate Acetonitrile/0.1% Water/0.1% (min) (ml/min) Trifluoroacetic acid Trifluoroacetic acid  0 0.8 10 90 18 0.8 10 90 30 0.8 70 30 32 0.8 70 30 33 0.8 10 90 43 0.8 10 90

[0048] The conditions for MSD are as follows: atmospheric pressure chemical ionization mode, positive and negative polarity, gas temperature of 350° C., vaporizer temperature of 450° C., drying gas flow rate of 6.0 l/min nitrogen, nebulizer pressure of 35 psig, capillary voltage of 2500 V, corona current of 7 μA, and fragmentor voltage of 80 V. A standard curve is prepared using chlorogenic acid with the molecular formula of C.sub.16H.sub.18O.sub.9 (catalog No. C44206, Aldrich, Milwaukee, Wis.).

[0049] Other types of chlorogenic acid are also likely present but are not detected using the conditions for analysis. It will be appreciated that the HPLC and MSD conditions may be modified to resolve different types of chlorogenic acid, and that the yield and content of chlorogenic acid may vary with different batches and different types of green coffee beans or different sources.

[0050] Extracts of chlorogenic acid from several batches of green coffee beans are prepared as solutions ranging from 2.8%.sup.w/w to 10%.sup.w/w, pH ranging from about pH 4.5 to about pH 6.0, and are added to various consumables based on the weight of the powder. These solutions are added to consumables to modify and/or mask off-tastes.

EXAMPLE 6

Chlorogenic Acid (Synthetic) Added to an Aged Artificially Sweetened Beverage

[0051] An artificially sweetened beverage is prepared by mixing 1.4 g aspartame, 0.9 g acesulfame K, 6 ml sodium benzoate (25%.sup.w/v in water), 1.3 ml phosphoric acid (85%.sup.w/v), and 0.5 ml citric acid (50%.sup.w/v in water). The volume of the mixture is adjusted to 1000 ml with water. The beverage mixture is aged for three weeks at 34° C.

[0052] A 2.8%.sup.w/w solution of a commercially available synthetic chlorogenic acid (>95% pure (1,3,4,5-tetrahydroxy-cyclohexanecarboxylic acid 3-[3,4-dihydroxycinnamate]), Sigma Chemical Co., St. Louis, Mo.), in water, pH 5.6, is added to a portion of the aged beverage to a final concentration of 0.003%.sup.w/v. The beverage containing chlorogenic acid is evaluated and compared to the untreated beverage by a six member panel of trained flavorists. The beverage containing the commercial chlorogenic acid is judged by the panel to display markedly less of the metallic, slightly bitter aftertaste found in the aged artificially sweetened beverage.

EXAMPLE 7

Chlorogenic Acid (Extracted) Added to an Aged Artificially Sweetened Beverage

[0053] To another portion of the artificially sweetened beverage prepared as described in the first paragraph of Example 6, an aqueous solution of chlorogenic acid from the powdered extract of green coffee beans is added to a final concentration of 0.003%.sup.w/v chlorogenic acid. This beverage is evaluated by the same flavorist panel as described in Example 6. The beverage containing chlorogenic acid extracted from green coffee beans is also judged to display markedly less of the metallic, slightly bitter aftertaste found in the aged artificially sweetened beverage.

EXAMPLE 8

Chlorogenic Acid Added to an Unflavored Alcoholic Beverage

[0054] A 10 proof (5% alcohol) unflavored beverage is prepared by mixing 5.26 ml Grain Neutral Spirits (95% alcohol), 92.24 ml water, 2.0 ml high fructose corn syrup, 0.25 ml sodium benzoate (10%.sup.w/v in water), and 0.25 ml potassium sorbate (10%.sup.w/v in water).

[0055] A solution of chlorogenic acid from a green coffee bean extract, prepared as previously described, is added to a portion of the alcoholic beverage to a final concentration of 0.0035%.sup.w/v chlorogenic acid. The beverage containing chlorogenic acid is evaluated by a six member panel of trained flavorists. The beverage is judged to display significantly less of the alcohol-burn taste than that observed in the untreated beverage.

EXAMPLE 9

Chlorogenic acid Added to a Soy Product

[0056] A solution of chlorogenic acid from a green coffee bean extract, prepared as previously described, is added to a commercial soy milk product (White Wave, Silk Chocolate) to final concentration of 0.04%.sup.w/v chlorogenic acid.

[0057] A six member panel of trained flavorists evaluating the product containing chlorogenic acid find the soy milk's beany aldehydic soy off-notes to be masked and perceive the product to be smoother and creamier in comparison to the product without chlorogenic acid.

EXAMPLE 10

Chlorogenic Acid Added to a Flavored Carbonated Beverage

[0058] A solution of chlorogenic acid from a green coffee bean extract, prepared as previously described, is added to a standard carbonated orange flavored beverage (flavor level 0.2%) to final concentration of 0.001%.sup.w/v chlorogenic acid.

[0059] A six member panel of trained flavorists compared the carbonated beverages with and without addition of chlorogenic acid. The panel finds the beverage containing chlorogenic acid to have a significantly lowered impact of the sharp, slightly burning sensation of the carbonation when compared to the beverage without added chlorogenic acid.

EXAMPLE 11

Chlorogenic Acid Added to Aspartame Sweetened Yogurt

[0060] A solution of chlorogenic acid from a green coffee bean extract, prepared as previously described, is added to a commercial non-fat yogurt (Dannon, Light ‘n Fit Vanilla Yogurt, with Aspartame & fructose added) to a final concentration of 0.005%.sup.w/v chlorogenic acid.

[0061] A panel of six trained flavorists compares the yogurts with and without addition of chlorogenic acid. The panel judges that the product containing chlorogenic acid displays an improved body and texture in the mouth, and that the overall sweetness perception is fuller and more rounded than the yogurt without addition of chlorogenic acid.