WO2019214567A1 - Compositions d'édulcorant et d'arôme, leurs procédés de fabrication et leurs procédés d'utilisation - Google Patents

Compositions d'édulcorant et d'arôme, leurs procédés de fabrication et leurs procédés d'utilisation Download PDF

Info

Publication number
WO2019214567A1
WO2019214567A1 PCT/CN2019/085635 CN2019085635W WO2019214567A1 WO 2019214567 A1 WO2019214567 A1 WO 2019214567A1 CN 2019085635 W CN2019085635 W CN 2019085635W WO 2019214567 A1 WO2019214567 A1 WO 2019214567A1
Authority
WO
WIPO (PCT)
Prior art keywords
rebaudioside
food
beverage
composition
glycosylated
Prior art date
Application number
PCT/CN2019/085635
Other languages
English (en)
Inventor
Weiyao Shi
Jingang Shi
Hansheng Wang
Xin Shi
Yi Wang
Wei LV
Yingxiang XIN
Thomas Eidenberger
Original Assignee
Epc Natural Products Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US16/402,728 external-priority patent/US11154079B2/en
Priority claimed from US16/402,360 external-priority patent/US11425923B1/en
Application filed by Epc Natural Products Co., Ltd. filed Critical Epc Natural Products Co., Ltd.
Priority to JP2020563513A priority Critical patent/JP7474201B2/ja
Priority to CN201980030742.XA priority patent/CN112218542B/zh
Priority to AU2019264701A priority patent/AU2019264701A1/en
Publication of WO2019214567A1 publication Critical patent/WO2019214567A1/fr

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
    • A23C9/156—Flavoured milk preparations ; Addition of fruits, vegetables, sugars, sugar alcohols or sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids

Definitions

  • the present disclosure relates generally to the application of Maillard reaction technology to sweeteners and flavoring agents, and their use in food and beverage products.
  • Caloric sugars are widely used in the food and beverage industry. However, there is a growing trend toward use of more healthy alternatives, including non-caloric or low caloric sweeteners.
  • Popular non-caloric sweeteners include high intensity synthetic sweeteers, such as aspartame (e.g., NutraSweet, Equal) , sucralose (Splenda) , and acesulfame potassium (also known as acesulfame K, or Ace-K) , as well as high intensity natural sweeteners, which are typically derived from plants, such as Stevia.
  • high intensity synthetic sweeteers such as aspartame (e.g., NutraSweet, Equal) , sucralose (Splenda) , and acesulfame potassium (also known as acesulfame K, or Ace-K)
  • high intensity natural sweeteners which are typically derived from plants, such as Stevia.
  • steviol glycosides can bind the volatiles of various flavors used in food, beverages, cosmetics, feeds and pharmaceuticals.
  • Steviol glycosides treated by the methods disclosed herein are widely soluble in water, water/alcohol, alcohol, and other organic solvents used for the flavor industry at different temperatures.
  • the Stevia compositions could naturally encapsulate the flavor produced during the processes described herein. Therefore, they also excellent carriers for encapsulating material for flavors, including but not limited to flavors and spices originated from plants such as bark, flowers, fruits, leaves, and animals, including concentrated meat and sea food soups etc., and their extracts such as essential oils, etc.
  • a processed flavor is added to a Stevia solution, then dried into a powder by any method, including but not limited spray-drying, crystallization, tray-drying, freeze drying etc.
  • volatile flavors can be preserved.
  • MRP flavors have to be maintained at low temperatures, such as 10°C.
  • An advantage of the present embodiments is that encapsulation of flavors by steviol glycosides can be kept at room temperature or even higher temperatures without significant loss of flavor. Further, the antioxidant properties of MRPs can play an additional role in protecting these flavors.
  • compositions can be designed to enhance a foam for a specific application, such as foamed/frothy coffee.
  • an anti-foaming agent can be added together or separately during the reaction processes described herein, such that the product can be used to prevent foaming for beverage bottling applications.
  • Maillard reactions create orthonasal and retronasal taste (s) .
  • the typically associated off-taste of steviol glycosides is either removed or masked with MRPs added to the steviol glycoside (s) and creates an overall good smell and taste of the resulting composition.
  • MRPs increase the bitterness threshold of steviol glycosides and enhance intensity of sweetness, thus making steviol glycosides useful for sugar replacement or sugar reduction in a product.
  • the inventors have surprisingly found that the flavors of compositions herein are the result of the process not only characterized by Maillard reaction between sugar donor and amine donor, but that the flavors are also synergized by different groups of steviol glycosides with or without non-steviol glycoside substances.
  • the volatile substances produced during the Maillard reactions are surprisingly retained by the Stevia, including non-volatiles, so the processes described herein substantially improve both the taste and odor and consequently, improve the overall profile of steviol glycosides to be sugar-like, honey-like, chocolate, caramel, etc.
  • the mixture of MRPs, including initial and final SGs from the Maillard reaction provide new odor and taste profiles.
  • the initial SGs’ typical undesired taste features are therefore reduced by the processes and compositions described herein and are no longer recognized as low purity SGs, which normally possess grassy tastes and smells.
  • MRP Maillard reaction product
  • the sweetener or flavoring agent composition comprises: (1) a first component comprising Maillard reaction product (MRP) composition formed from a reaction mixture comprising: (a) a Stevia extract, a glycosylated Stevia extract, one or more purified steviol glycosides, and/or one or more glycosylated steviol glycosides; (b) one or more amine donors having a free amino group; and (2) a second component comprising one or more sweeteners, wherein the first and second components are present in the sweetener composition in an amount in the ranges of 1-100%of the sweetener composition.
  • MRP Maillard reaction product
  • the present application provides a non-Steviol glycoside sweetener-derived MRP composition
  • a non-Steviol glycoside sweetener-derived MRP composition comprising: a Maillard reaction product (MRP) composition formed from a reaction mixture comprising: (A) a non-Stevia sweetener; (B) a reducing sugar having a free carbonyl group; and (C) one or more amine donors having a free amino group
  • the non-Stevia sweetener is selected from the group consisting of sweet tea extracts, swingle extracts, glycosylated sweet tea extracts, glycosylated swingle extracts, glycosylated sweet tea glycosides, glycosylated mogrosides, glycyrrhizin, glycosylated glycyrrhizin, rubusoside, glycosylated rubusoside, suaviosides, glycosylated suaviosides, mogrosides, glycosylated mogrosides and sucralose,
  • the present application provides a beverage containing a non-Steviol glycoside sweetener-derived MRP (NS-MRP) composition, wherein the NS-MRP composition is formed from a reaction mixture comprising: (A) a non-Stevia sweetener; (B) a reducing sugar having a free carbonyl group; and (C) one or more amine donors having a free amino group; and wherein the non-Stevia sweetener is selected from the group consisting of sweet tea extracts, swingle extracts, glycosylated sweet tea extracts, glycosylated swingle extracts, glycosylated sweet tea glycosides, glycosylated mogrosides, glycyrrhizin, glycosylated glycyrrhizin, rubusoside, glycosylated rubusoside, suaviosides, glycosylated suaviosides, mogrosides, glycosylated mogrosides and sucralose, and wherein the M
  • the present application provides a beverage containing an MRP composition formed from a reaction mixture comprising: (1) one or more Stevia extracts, one or more glycosylated Stevia extracts, one or more steviol glycosides, and/or one or more glycosylated steviol glycosides, and (2) one or more amine donors having a free amino group.
  • the present application provide a beverage containing an MRP composition formed from a reaction mixture comprising: (1) an added Maillard reaction product (MRP) composition formed from a reaction mixture comprising one or more reducing sugars having a free carbonyl group, and one or more amine donors having a free amino group, and (2) one or more Stevia extracts, one or more glycosylated Stevia extracts, one or more purified steviol glycosides, and/or one or more glycosylated steviol glycosides, wherein the MRP composition is present in the beverage at a final concentration of 1-15,000 ppm.
  • MRP Maillard reaction product
  • the present application provides a beverage comprising a steviol glycoside-derived MRP (S-MRP) composition, wherein the S-MRP composition is formed from a reaction mixture comprising: (1) a Stevia extract and/or a glycosylated Stevia extracts; and (2) one or more amine donors having a free amino group, wherein the MRP composition comprises an Amadori product, and wherein the S-MRP composition is present in the beverage in a final concentration of 1-15,000 ppm.
  • S-MRP steviol glycoside-derived MRP
  • the beverage comprises an S-MRPs composition formed from a reaction mixture comprising: (1) a Stevia extract and/or a glycosylated Stevia extract; (2) one or more reducing sugars having a free carbonyl group; and (3) one or more amine donors having a free amino group, wherein the MRP composition comprises an Amadori product, and wherein the MRP composition is present in the beverage in a final concentration of 1-15,000 ppm.
  • the present application provides a method for improving the taste profile of a beverage by adding an S-MRP composition thereto, wherein the MRP composition is produced by: (1) heating a reaction mixture comprising (a) a steviol glycoside (SG) containing composition and one or more amine donors comprising a free amino group; or (2) heating a reaction mixture comprising (a) an SG-containing composition, (b) one or more amine donors comprising a free amino group, and (c) one or more reducing sugars comprising a free carbonyl group.
  • SG steviol glycoside
  • the method for improving the taste profile of a beverage includes the step of adding an MRP composition to the beverage, wherein the MRP composition is produced by heating a reaction mixture comprising (a) one or more amine donors comprising a free amino group; and (b) one or more reducing sugars comprising a free carbonyl group.
  • a method for improving the taste profile of a beverage includes the steps of: (1) adding an MRP composition to the beverage, wherein the MRP composition is produced by heating a reaction mixture for a period of time sufficient to initiate a Maillard reaction, wherein the reaction mixture comprises: (A) one or more reducing sugars comprising a free carbonyl group, and (B) one or more amine donors comprising a free amino group; and (2) adding a sweetener composition to the beverage to produce a final product, wherein the sweetener composition comprises one or more Stevia extracts, one or more glycosylated Stevia extracts, one or more purified steviol glycosides, and/or one or more glycosylated steviol glycosides, wherein the MRP composition is present in the final product in a concentration of 0.1-15,000 ppm.
  • a method for improving the taste profile of a bakery product includes the steps of: (1) preparing a dough comprising: (A) a Maillard reaction product (MRP) composition formed from a reaction mixture comprising: (i) one or more reducing sugars having a free carbonyl group, and (ii) one or more amine donors having a free amino group; and (B) one or more amine donors having a free amino group; and (2) baking the dough to produce the bakery product.
  • MRP Maillard reaction product
  • the present application provides a food product or beverage comprising a non-volatile component from an S-MRP composition.
  • the food product includes one or more non-volatile compounds from an MRP composition formed from a reaction mixture comprising: (i) a Stevia extract, a glycosylated, Stevia extract one or more purified steviol glycosides, and/or one or more glycosylated steviol glycosides; and (ii) one or more amine donors having a free amino group, wherein the one or more non-volatile compounds are present in the food product in an amount in the range of 0.0001-99 wt %of the food product.
  • the beverage includes one or more non-volatile compounds from a Maillard reaction product (MRP) composition formed from a reaction mixture comprising: (i) a Stevia extract, a glycosylated, Stevia extract one or more purified steviol glycosides, and/or one or more glycosylated steviol glycosides; and (ii) one or more amine donors having a free amino group, wherein the one or more non-volatile compounds are present in the beverage in an final concentration in the range of 1 ppm-15,000 ppm.
  • MRP Maillard reaction product
  • a method for improving the taste or mouth feel of a food product comprises the step of adding an MRP composition during the preparation of a food product to produce a final product, wherein the MRP composition is produced by: (1) heating a reaction mixture comprising (a) an steviol glycoside (SG) -containing composition and (b) one or more amine donors comprising a free amino group; or (2) heating a reaction mixture comprising (a) an SG-containing composition, (b) one or more amine donors comprising a free amino group, and (c) one or more reducing sugars comprising a free carbonyl group; or (3) heating a reaction mixture comprising (a) an SG-containing composition, (b) one or more amine donors comprising a free amino group, (c) one or more reducing sugars comprising a free carbonyl group, and (d) thaumatin.
  • a method for improving the taste or mouth feel of a sweetener composition comprises the step of adding an MRP composition to the sweetener composition to product a final product, wherein the MRP composition is produced by heating a reaction mixture comprising: (1) one or more reducing sugars having a free carbonyl group; and (2) one or more amine donors having a free amino group, wherein the MRP composition is present in the final product in an amount of 0.0001-10 wt %.
  • the present application provides a dough comprising: (1) a Maillard reaction product (MRP) composition formed from a reaction mixture comprising: (a) a first component comprising one or more reducing sugars having a free carbonyl group, and (b) one or more amine donors having a free amino group; and (2) a second component comprising a Stevia extract, a glycosylated Stevia extract, one or more purified steviol glycosides, and/or one or more glycosylated steviol glycosides, wherein the first and second components are present in the dough in a total amount in the range of 0.0001-20 wt %of the dough.
  • MRP Maillard reaction product
  • the present application provide a dough comprising: (1) a first component comprising a Maillard reaction product (MRP) composition formed from a reaction mixture comprising: (a) a Stevia extract, a glycosylated extract, one or more purified steviol glycosides, and/or one or more glycosylated steviol glycosides, and (b) one or more amine donors having a free amino group; and (2) a second component comprising one or more sweeteners, wherein the first and second components are present in the dough in a total amount in the range of 0.0001-50 wt %of the dough.
  • MRP Maillard reaction product
  • the present application provides a dairy product comprising: (1) a first component comprising an MRP composition formed from a reaction mixture comprising: (a) one or more reducing sugars having a free carbonyl group, and (b) one or more amine donors having a free amino group; and (2) a second component comprising a Stevia extract, a glycosylated Stevia extract, one or more purified steviol glycosides, and/or one or more glycosylated steviol glycosides, wherein the first and second components are present in the dairy product in a total amount in the range of 0.0001-10 wt %of the dairy product.
  • the dairy product comprises: (1) a first component comprising an MRP composition formed from a reaction mixture comprising: (a) a Stevia extract, a glycosylated Stevia extract, one or more purified steviol glycosides, and/or one or more glycosylated steviol glycosides, and (b) one or more amine donors having a free amino group; and (2) a second component comprising one or more sweeteners, wherein the first and second components are present in the dairy product in a total amount in the range of 0.0001-10 wt %of the dairy product.
  • Figure 1 depicts a relationship between the intensity of floral taste to the ratio of stevia to glucose and phenylalanine mixtures.
  • Figure 2 depicts a relationship between the intensity of tangerine taste to the ratio of stevia to galactose and glutamic acid mixtures.
  • Figure 3 depicts a relationship between the intensity of peach taste to the ratio of stevia to mannose and lysine mixtures.
  • Figure 4 depicts a relationship between the intensity of chocolate taste to the ratio of stevia to mannose and valine mixtures.
  • Figure 5 depicts a relationship between the intensity of popcorn taste to the ratio of stevia to mannose and proline mixtures.
  • Figure 6 depicts the relationship between the sensory evaluation results to the ratio of X&P mixture to stevia extract.
  • Figure 7 depicts relationship between the Overall-likeability score to the ratio of X&P mixture to stevia extract.
  • Figure 8 depicts the comparison between the products of EX41-1 and EX41-2.
  • Figure 9 depicts the relationship between the sensory evaluation results to the ratio of R&A mixture to stevia extract.
  • Figure 10 depicts the relationship between the Overall likeability score to the ratio of R&A mixture to stevia extract.
  • Figure 11 depicts the relationship between the sensory evaluation results to the ratio of G&P mixture to stevia extract.
  • Figure 12 depicts the relationship between the Overall likeability score to the ratio of G&P mixture to stevia extract.
  • Figure 13 depicts the comparison between the products of EX45-3 and EX45-4.
  • Figure 14 depicts the relationship between the sensory evaluation results to the ratio of R&V mixture to stevia extract.
  • Figure 15 depicts the relationship between the Overall likeability score to the ratio of R&V mixture to stevia extract.
  • Figure 16 depicts the comparison between the products of EX48-1 and EX48-2.
  • Figure 17 depicts the comparison between the products of EX49-1 and EX49-2.
  • Figure 18 depicts a flow diagram for testing of mixtures of amino acids, steviol glycosides and reaction products.
  • Figure 20 depicts an MS-spectrum related to Figure 19.
  • Figure 23 depicts an MS-Spectrum related to Figure 22.
  • Figure 32 depicts a chromatogram of the reaction Phe+Glucuronic Acid (SIM mode) .
  • Upper Lane: m/z 166 (Phe)
  • m/z 328 (MRI Phe+Glucose)
  • m/z 343.2 (Phe+Glucuronic Acid) .
  • Figure 33 depicts a chromatogram of the reaction of Phe+Glucose+Glucuronic Acid (SIM mode) .
  • Upper Lane: m/z 166 (Phe)
  • m/z 328 (MRI Phe+Glucose)
  • m/z 343.2 (Phe+Glucuronic Acid) .
  • Figure 34 depicts a chromatogram of the reaction Phe+Glucuronolactone (SIM mode) .
  • Upper Lane: m/z 166 (Phe)
  • Figure 35 depicts a chromatogram of the reaction of Phe+Glucose+Glucuronolactone (SIM mode) .
  • Upper Lane: m/z 166 (Phe)
  • m/z 328 (MRI Phe+Glucose)
  • m/z 343.2 (Phe+Glucuronolactone) .
  • Figure 36 depicts a chromatogram of unreacted reactants, Glucuronic Acid (SIM mode) .
  • Figure 37 depicts a chromatogram of unreacted reactants Glucuronolactone (SIM mode) .
  • Figure 44 depicts a chromatogram of a sugar degradation product and MS spectrum with corresponding m/z values.
  • Upper lane Phe+SG Sample No. 1-1 medium lane Ala+SG Sample No. 1-1, lower lane Lys+SG Sample No. 1-1.
  • Figure 46 depicts the decay of phenylalanine at 120 °C over time.
  • Figure 48 depicts the decay of glucose at 120 °C over time.
  • Figure 49 shows active iron-III reduction of combinations of amino acids and Reb-A.
  • Figure 50 shows radical scavenging properties of combinations of amino acids and Reb-A.
  • Figure 51 shows the relationship between the sensory evaluation results to the ratio of xylose to phenylalanine.
  • Figure 52 shows the relationship between the Overall likeability score to the ratio of xylose to phenylalanine.
  • Figure 53 shows the sensory evaluation with respect to coffee sweetened with sugar, RA60/SG95 or with Flora MRP.
  • Figure 54 shows the sensory evaluation with respect to Red Bull sugar free with thaumatin or thaumatin and Flora MRP.
  • Figure 55 shows the sensory evaluation with respect to Monster Energy drink with thaumatin or thaumatin and Flora MRP.
  • Figure 56 shows the sensory evaluation with respect to Starbucks vanilla Frappuccino with thaumatin or thaumatin and Flora MRP.
  • Figure 57 shows the sensory evaluation with respect to Starbuck caramel Frappuccino with thaumatin or thaumatin and caramel MRP.
  • Figure 58 shows the relationship between the sensory evaluation results to the ratio of phenylalanine to xylose of example 90.
  • Figure 59 shows the relationship between the overall likeability results to the ratio of phenylalanine to xylose of example 90.
  • Figure 60 shows the relationship between the sensory evaluation results to the ratio of sucralose to the mixture of xylose and phenylalanine of example 91.
  • Figure 61 shows the relationship between the overall likeability results to the ratio of sucralose to the mixture of xylose and phenylalanine of example 91.
  • Figure 62 shows the relationship between the sensory evaluation results to the ratio of proline to rhamnose of example 92.
  • Figure 63 shows the relationship between the overall likeability results to the ratio of proline to rhamnose of example 92.
  • Figure 64 shows the relationship between the sensory evaluation results to the ratio of sucralose to the mixture of proline and rhamnose of example 93.
  • Figure 65 shows the relationship between the overall likeability results to the ratio of sucralose to the mixture of proline and rhamnose of example 93.
  • Figure 66 shows the relationship between the sensory evaluation results to the ratio of alanine to xylose of example 94.
  • Figure 67 shows the relationship between the overall likeability results to the ratio of alanine to xylose of example 94.
  • Figure 68 shows the relationship between the sensory evaluation results to the ratio of sucralose to the mixture of alanine and xylose of example 95.
  • Figure 69 shows the relationship between the overall likeability results to the ratio of sucralose to the mixture of alanine and xylose of example 95.
  • Figure 70 shows the relationship between the sensory evaluation results to the ratio of MRP-CH to RA of example 106.
  • Figure 71 shows the relationship between the overall likeability results to the ratio of MRP-CH to RA of example 106.
  • Figure 72 shows the relationship between the sensory evaluation results to the ratio of S-MRP-CH to RA of example 107.
  • Figure 73 shows the relationship between the overall likeability results to the ratio of S-MRP-CH to RA of example 107.
  • Figure 74 shows the relationship between the sensory evaluation results to the ratio of TS-MRP-CH to RA of example 108.
  • Figure 75 shows the relationship between the overall likeability results to the ratio of TS-MRP-CH to RA of example 108.
  • Figure 76 shows the relationship between the sensory evaluation results to the ratio of STV to MRP-FL of example 109.
  • Figure 77 shows the relationship between the overall likeability results to the ratio of STV to MRP-FL of example 109.
  • Figure 78 shows the relationship between the sensory evaluation results to the ratio of STV to S-MRP-FL of example 110.
  • Figure 79 shows the relationship between the overall likeability results to the ratio of STV to S-MRP-FL of example 110.
  • Figure 80 shows the relationship between the sensory evaluation results to the ratio of STV to TS-MRP-FL of example 111.
  • Figure 81 shows the relationship between the overall likeability results to the ratio of STV to TS-MRP-FL of example 111.
  • Figure 82 shows the relationship between the sensory evaluation results to the ratio of RD to MRP-FL of example 112.
  • Figure 83 shows the relationship between the overall likeability results to the ratio of RD to MRP-FL of example 112.
  • Figure 84 shows the relationship between the sensory evaluation results to the ratio of RD to S-MRP-FL of example 113.
  • Figure 85 shows the relationship between the overall likeability results to the ratio of RD to S-MRP-FL of example 113.
  • Figure 86 shows the relationship between the sensory evaluation results to the ratio of RD to TS-MRP-FL of example 114.
  • Figure 87 shows the relationship between the overall likeability results to the ratio of RD to TS-MRP-FL of example 114.
  • Figure 88 shows the relationship between the sensory evaluation results to the ratio of RM to MRP-CA of example 115.
  • Figure 89 shows the relationship between the overall likeability results to the ratio of RM to MRP-CA of example 115.
  • Figure 90 shows the relationship between the sensory evaluation results to the ratio of RM to S-MRP-CA of example 116.
  • Figure 91 shows the relationship between the overall likeability results to the ratio of RM to S-MRP-CA of example 116.
  • Figure 92 shows the relationship between the sensory evaluation results to the ratio of RM to TS-MRP-CA of example 117.
  • Figure 93 shows the relationship between the overall likeability results to the ratio of RM to TS-MRP-CA of example 117.
  • Figure 94 shows the relationship between the sensory evaluation results to the ratio of MRP-CH to RD+RM (9: 1) of example 118.
  • Figure 95 shows the relationship between the overall likeability results to the ratio of MRP-CH to RD+RM (9: 1) of example 118.
  • Figure 96 shows the relationship between the sensory evaluation results to the ratio of S-MRP-CH to RD+RM (9: 1) of example 119.
  • Figure 97 shows the relationship between the overall likeability results to the ratio of S-MRP-CH to RD+RM (9: 1) of example 119.
  • Figure 98 shows the relationship between the sensory evaluation results to the ratio of TS-MRP-CH to RD+RM (9: 1) of example 120.
  • Figure 99 shows the relationship between the overall likeability results to the ratio of TS-MRP-CH to RD+RM (9: 1) of example 120.
  • Figure 100 shows the relationship between the sensory evaluation results to the ratio of MRP-CH to RD+RM (5: 5) of example 121.
  • Figure 101 shows the relationship between the overall likeability results to the ratio of MRP-CH to RD+RM (5: 5) of example 121.
  • Figure 102 shows the relationship between the sensory evaluation results to the ratio of S-MRP-CH to RD+RM (5: 5) of example 122.
  • Figure 103 shows the relationship between the overall likeability results to the ratio of S-MRP-CH to RD+RM (5: 5) of example 122.
  • Figure 104 shows the relationship between the sensory evaluation results to the ratio of TS-MRP-CH to RD+RM (5: 5) of example 123.
  • Figure 105 shows the relationship between the overall likeability results to the ratio of TS-MRP-CH to RD+RM (5: 5) of example 123.
  • Figure 106 shows the relationship between the sensory evaluation results to the ratio of MRP-CH to RD+RM (1: 9) of example 124.
  • Figure 107 shows the relationship between the overall likeability results to the ratio of MRP-CH to RD+RM (1: 9) of example 124.
  • Figure 108 shows the relationship between the sensory evaluation results to the ratio of S-MRP-CH to RD+RM (1: 9) of example 125.
  • Figure 109 shows the relationship between the overall likeability results to the ratio of S-MRP-CH to RD+RM (1: 9) of example 125.
  • Figure 110 shows the relationship between the sensory evaluation results to the ratio of TS-MRP-CH to RD+RM (1: 9) of example 126.
  • Figure 111 shows the relationship between the overall likeability results to the ratio of TS-MRP-CH to RD+RM (1: 9) of example 126.
  • Figure 112 shows the relationship between the sensory evaluation results to the ratio of MRP-CA to RU of example 127.
  • Figure 113 shows the relationship between the overall likeability results to the ratio of MRP-CA to RU of example 127.
  • Figure 114 shows the relationship between the sensory evaluation results to the ratio of S-MRP-CA to RU of example 128.
  • Figure 115 shows the relationship between the overall likeability results to the ratio of S-MRP-CA to RU of example 128.
  • Figure 116 shows the relationship between the sensory evaluation results to the ratio of TS-MRP-CA to RU of example 129.
  • Figure 117 shows the relationship between the overall likeability results to the ratio of TS-MRP-CA to RU of example 129.
  • Figure 118 shows the relationship between the sensory evaluation results to the ratio of mogroside V20 to MRP-FL of example 130.
  • Figure 119 shows the relationship between the overall likeability results to the ratio of mogroside V20 to MRP-FL of example 130.
  • Figure 120 shows the relationship between the sensory evaluation results to the ratio of mogroside V20 to S-MRP-FL of example 131.
  • Figure 121 shows the relationship between the overall likeability results to the ratio of mogroside V20 to S-MRP-FL of example 131.
  • Figure 122 shows the relationship between the sensory evaluation results to the ratio of mogroside V20 to TS-MRP-FL of example 132.
  • Figure 123 shows the relationship between the overall likeability results to the ratio of mogroside V20 to TS-MRP-FL of example 132.
  • Figure 124 shows the relationship between the sensory evaluation results to the ratio of mogroside V50 to MRP-CA of example 133.
  • Figure 125 shows the relationship between the overall likeability results to the ratio of mogroside V50 to MRP-CA of example 133.
  • Figure 126 shows the relationship between the sensory evaluation results to the ratio of mogroside V50 to S-MRP-CA of example 134.
  • Figure 127 shows the relationship between the overall likeability results to the ratio of mogroside V50 to S-MRP-CA of example 134.
  • Figure 128 shows the relationship between the sensory evaluation results to the ratio of mogroside V50 to TS-MRP-CA of example 135.
  • Figure 129 shows the relationship between the overall likeability results to the ratio of mogroside V50 to TS-MRP-CA of example 135.
  • Figure 130 shows the relationship between the sensory evaluation results to the ratio of sucralose, aspartame to MRP-CH of example 136.
  • Figure 131 shows the relationship between the overall likeability results to the ratio of sucralose, aspartame to MRP-CH of example 136.
  • Figure 132 shows the relationship between the sensory evaluation results to the ratio of sucralose, aspartame to S-MRP-CH of example 137.
  • Figure 133 shows the relationship between the overall likeability results to the ratio of sucralose, aspartame to S-MRP-CH of example 137.
  • Figure 134 shows the relationship between the sensory evaluation results to the ratio of sucralose, aspartame to TS-MRP-CH of example 138.
  • Figure 135 shows the relationship between the overall likeability results to the ratio of sucralose, aspartame to TS-MRP-CH of example 138.
  • Figure 136 shows the relationship between the sensory evaluation results to the ratio of sucralose to MRP-CA of example 139.
  • Figure 137 shows the relationship between the overall likeability results to the ratio of sucralose to MRP-CA of example 139.
  • Figure 138 shows the relationship between the sensory evaluation results to the ratio of sucralose to S-MRP-CA of example 140.
  • Figure 139 shows the relationship between the overall likeability results to the ratio of sucralose to S-MRP-CA of example 140.
  • Figure 140 shows the relationship between the sensory evaluation results to the ratio of sucralose to TS-MRP-CA of example 141.
  • Figure 141 shows the relationship between the overall likeability results to the ratio of sucralose to TS-MRP-CA of example 141.
  • Figure 142 shows the label of Heinz Ketchup Classic.
  • Figure 143 shows the label of Heinz Ketchup 50%reduced sugar &salt.
  • Figure 144a shows TIC of the Stevia.
  • Figure 144b shows TIC of the standard MRPs.
  • Figure 144c shows TIC of the Citrus MRPs.
  • Figure 145a shows the molecular structure of (-) -Limonene.
  • Figure 145b shows the molecular structure of Nerol.
  • Figure 145c shows the molecular structure of Bergamot.
  • Figure 145d shows the molecular structure of Aromadendrene Oxide.
  • Figure 145e shows the molecular structure of ⁇ -Calacorene.
  • Figure 145f shows the molecular structure of Ionone.
  • Figures 146a through 146j shows sensory analysis results for tests in final applications.
  • Figures 147a and 147b show the results of SG-MRPs flavor threshold determination.
  • Figures 148a through 148d show the HPLC chromatograms of the samples as tested.
  • Figures 149a, 149b and 149c show ESI--MS spectra of 3 peaks related to the stevia extract of example 37, sample A and sample B (9.8, 10.8 and 12.3 minutes)
  • Figures 150a, 150b and 150c show UV-VIS spectra of 2 peaks related to the stevia extract from example 37, sample A and sample B (9.8, 10.8 and 12.3 minutes) .
  • Figure 156 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V50 to MRP-FL.
  • Figure 157 demonstrates the relationship between the overall likeability results to the ratio of mogroside V50 to MRP-FL.
  • Figure 158 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V50 to MRP-CH.
  • Figure 159 demonstrates the relationship between the overall likeability results to the ratio of mogroside V50 to MRP-CH.
  • Figure 160 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V50 to MRP-CI.
  • Figure 161 demonstrates the relationship between the overall likeability results to the ratio of mogroside V50 to MRP-CI.
  • Figure 162 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V50 to S-MRP-FL.
  • Figure 163 demonstrates the relationship between the overall likeability results to the ratio of mogroside V50 to S-MRP-FL.
  • Figure 164 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V50 to S-MRP-CH.
  • Figure 165 demonstrates the relationship between the overall likeability results to the ratio of mogroside V50 to S-MRP-CH.
  • Figure 166 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V50 to S-MRP-CI.
  • Figure 167 demonstrates the relationship between the overall likeability results to the ratio of mogroside V50 to S-MRP-CI.
  • Figure 168 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V50 to TS-MRP-FL.
  • Figure 169 demonstrates the relationship between the overall likeability results to the ratio of mogroside V50 to TS-MRP-FL.
  • Figure 170 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V50 to TS-MRP-CH.
  • Figure 171 demonstrates the relationship between the overall likeability results to the ratio of mogroside V50 to TS-MRP-CH.
  • Figure 172 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V50 to TS-MRP-CI.
  • Figure 173 demonstrates the relationship between the overall likeability results to the ratio of mogroside V50 to TS-MRP-CI.
  • Figure 174 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V20 to MRP-CH.
  • Figure 175 demonstrates the relationship between the overall likeability results to the ratio of mogroside V20 to MRP-CH.
  • Figure 176 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V20 to MRP-CA.
  • Figure 177 demonstrates the relationship between the overall likeability results to the ratio of mogroside V20 to MRP-CA.
  • Figure 178 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V20 to MRP-CI.
  • Figure 179 demonstrates the relationship between the overall likeability results to the ratio of mogroside V20 to MRP-CI.
  • Figure 180 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V20 to S-MRP-CH.
  • Figure 181 demonstrates the relationship between the overall likeability results to the ratio of mogroside V20 to S-MRP-CH.
  • Figure 182 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V20 to S-MRP-CA.
  • Figure 183 demonstrates the relationship between the overall likeability results to the ratio of mogroside V20 to S-MRP-CA.
  • Figure 184 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V20 to S-MRP-CI.
  • Figure 185 demonstrates the relationship between the overall likeability results to the ratio of mogroside V20 to S-MRP-CI.
  • Figure 186 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V20 to TS-MRP-CH.
  • Figure 187 demonstrates the relationship between the overall likeability results to the ratio of mogroside V20 to TS-MRP-CH.
  • Figure 188 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V20 to TS-MRP-CA.
  • Figure 189 demonstrates the relationship between the overall likeability results to the ratio of mogroside V20 to TS-MRP-CA.
  • Figure 190 demonstrates the relationship between the sensory evaluation results to the ratio of mogroside V20 to TS-MRP-CI.
  • Figure 191 demonstrates the relationship between the overall likeability results to the ratio of mogroside V20 to TS-MRP-CI.
  • Figure 192 demonstrates the relationship between the sensory evaluation results to the ratio of MRP-CH to RU.
  • Figure 193 demonstrates the relationship between the overall likeability results to the ratio of MRP-CH to RU.
  • Figure 194 demonstrates the relationship between the sensory evaluation results to the ratio of MRP-FL to RU.
  • Figure 195 demonstrates the relationship between the overall likeability results to the ratio of MRP-FL to RU.
  • Figure 196 demonstrates the relationship between the sensory evaluation results to the ratio of MRP-CI to RU.
  • Figure 197 demonstrates the relationship between the overall likeability results to the ratio of MRP-CI to RU.
  • Figure 198 demonstrates the relationship between the sensory evaluation results to the ratio of S-MRP-CH to RU.
  • Figure 199 demonstrates the relationship between the overall likeability results to the ratio of S-MRP-CH to RU.
  • Figure 200 demonstrates the relationship between the sensory evaluation results to the ratio of S-MRP-FL to RU.
  • Figure 201 demonstrates the relationship between the overall likeability results to the ratio of S-MRP-FL to RU.
  • Figure 202 demonstrates the relationship between the sensory evaluation results to the ratio of S-MRP-CI to RU.
  • Figure 203 demonstrates the relationship between the overall likeability results to the ratio of S-MRP-CI to RU.
  • Figure 204 demonstrates the relationship between the sensory evaluation results to the ratio of TS-MRP-CH to RU
  • Figure 205 demonstrates the relationship between the overall likeability results to the ratio of TS-MRP-CH to RU.
  • Figure 206 demonstrates the relationship between the sensory evaluation results to the ratio of TS-MRP-FL to RU.
  • Figure 207 demonstrates the relationship between the overall likeability results to the ratio of TS-MRP-FL to RU.
  • Figure 208 demonstrates the relationship between the sensory evaluation results to the ratio of TS-MRP-CI to RU.
  • Figure 209 demonstrates the relationship between the overall likeability results to the ratio of TS-MRP-CI to RU.
  • Figure 210 represents graphically a citrus beverage with a stevia derived MRP stored at 2-4°C over a period of time (flavor intensity) .
  • Figure 211 represents graphically a citrus beverage with a stevia derived MRP stored at 2-4°C over a period of time (flavor intensity) .
  • Figure 212 represents graphically a citrus beverage with a stevia derived MRP stored at 2-4°C over a period of time.
  • Figure 213 represents graphically a citrus beverage with a stevia derived MRP stored at 2-4°C over a period of time (mouth feel) .
  • Figure 214 represents graphically a citrus beverage with a stevia derived MRP stored at 20-22°C over a period of time (flavor intensity) .
  • Figure 215 represents graphically a citrus beverage with a stevia derived MRP stored at 20-22°C over a period of time (flavor intensity) .
  • Figure 216 represents graphically a citrus beverage with a stevia derived MRP stored at 20-22°C over a period of time.
  • Figure 217 represents graphically a citrus beverage with a stevia derived MRP stored at 20-22°C over a period of time (mouth feel) .
  • Figure 218 represents graphically a cola beverage with a stevia derived MRP stored at 2-4°C over a period of time (flavor intensity) .
  • Figure 219 represents graphically a cola beverage with a stevia derived MRP stored at 2-4°C over a period of time (flavor intensity) .
  • Figure 220 represents graphically a cola beverage with a stevia derived MRP stored at 2-4°C over a period of time.
  • Figure 221 represents graphically a cola beverage with a stevia derived MRP stored at 2-4°C over a period of time (mouth feel) .
  • Figure 222 represents graphically a cola beverage with a stevia derived MRP stored at 20-22°C over a period of time (flavor intensity) .
  • Figure 223 represents graphically a cola beverage with a stevia derived MRP stored at 20-22°C over a period of time (flavor intensity) .
  • Figure 224 represents graphically a cola beverage with a stevia derived MRP stored at 20-22°C over a period of time.
  • Figure 225 represents graphically a cola beverage with a stevia derived MRP stored at 20-22°C over a period of time (mouth feel) .
  • Figure 226 depicts the sweetness, flavor and mouth feel profiles of samples of low fat vanilla yogurt (LFVY) with stevia MRPs.
  • LUVY low fat vanilla yogurt
  • Figure 227 depicts the sweetness, flavor and mouth feel profiles of samples of low fat vanilla yogurt (LFVY) with stevia MRPs and thaumatin.
  • LUVY low fat vanilla yogurt
  • Figure 228 depicts the relationship between the sensory evaluation results to the ratio of MRP-FL to RA90/RD7+RM (1: 9) .
  • Figure 229 depicts the relationship between the overall likeability results to the ratio of MRP-FL to RA90/RD7+RM (1: 9) .
  • Figure 230 depicts the relationship between the sensory evaluation results to the ratio of S-MRP-PC to RA90/RD7+RM (5: 5) .
  • Figure 231 depicts the relationship between the overall likeability results to the ratio of S-MRP-PC to RA90/RD7+RM (5: 5) .
  • Figure 232 depicts the relationship between the sensory evaluation results to the ratio of TS-MRP-CA to RA90/RD7+RM (9: 1) .
  • Figure 233 depicts the relationship between the overall likeability results to the ratio of TS-MRP-CA to RA90/RD7+RM (9: 1) .
  • Figure 234 depicts the relationship between the sensory evaluation results to the ratio of MRP-CA to RA80/RB10/RD6+RM (1: 9) .
  • Figure 235 depicts the relationship between the overall likeability results to the ratio of MRP-CA to RA80/RB10/RD6+RM (1: 9) .
  • Figure 236 depicts the relationship between the sensory evaluation results to the ratio of S-MRP-PC to RA80/RB10/RD6+RM (5: 5) .
  • Figure 237 depicts the relationship between the overall likeability results to the ratio of S-MRP-PC to RA80/RB10/RD6+RM (5: 5) .
  • Figure 238 depicts the relationship between the sensory evaluation results to the ratio of TS-MRP-FL to RA80/RB10/RD6+RM (9: 1) .
  • Figure 239 depicts the relationship between the overall likeability results to the ratio of TS-MRP-FL to RA80/RB10/RD6+RM (9: 1) .
  • Figure 240 depicts the relationship between the sensory evaluation results to the ratio of S-MRP-GRA50-FL to RA99.
  • Figure 241 depicts the relationship between the overall likeability results to the ratio of S-MRP-GRA50-FL to RA99.
  • Figure 242 depicts the relationship between the sensory evaluation results to the ratio of S-MRP-GRA80-CA to RD+RM (1: 3) .
  • Figure 243 depicts the relationship between the overall likeability results to the ratio of S-MRP-GRA80-CA to RD+RM (1: 3) .
  • Figure 244 depicts the relationship between the sensory evaluation results to the ratio of S-MRP-GRA95-PC to mogroside V50.
  • Figure 245 depicts the relationship between the overall likeability results to the ratio of S-MRP-GRA95-PC to mogroside V50.
  • Figure 246 depicts the relationship between the sensory evaluation results to the ratio of TS-MRP-GRA50-FL to aspartame.
  • Figure 247 depicts the relationship between the overall likeability results to the ratio of TS-MRP-GRA50-FL to aspartame.
  • Figure 248 depicts the relationship between the sensory evaluation results to the ratio of TS-MRP-GRA80-CA to sucralose.
  • Figure 249 depicts the relationship between the overall likeability results to the ratio of TS-MRP-GRA80-CA to sucralose.
  • Figure 250 depicts the relationship between the sensory evaluation results to the ratio of TS-MRP-GRA95-PC to Acesulfame potassium.
  • Figure 251 depicts the relationship between the overall likeability results to the ratio of TS-MRP-GRA95-PC to Acesulfame potassium.
  • Figure 252 depicts the relationship between the sensory evaluation results to the ratio of NVS-MRP-FL to RM.
  • Figure 253 depicts the relationship between the overall likeability results to the ratio of NVS-MRP-FL to RM.
  • Figure 254 depicts the relationship between the sensory evaluation results to the ratio of NVS-MRP-CA to sucralose.
  • Figure 255 depicts the relationship between the overall likeability results to the ratio of NVS-MRP-CA to sucralose.
  • Figure 256 depicts the relationship between the sensory evaluation results to the ratio of MRP-CH to Advantame.
  • Figure 257 depicts the relationship between the overall likeability results to the ratio of MRP-CH to Advantame.
  • Figure 258 depicts the relationship between the sensory evaluation results to the ratio of S-MRP-CH to Advantame.
  • Figure 259 depicts the relationship between the overall likeability results to the ratio of S-MRP-CH to Advantame.
  • Figure 260 depicts the relationship between the sensory evaluation results to the ratio of TS-MRP-CH to Advantame.
  • Figure 261 depicts the relationship between the overall likeability results to the ratio of TS-MRP-CH to Advantame.
  • Figure 262 depicts the GC/MS spectra of standard MRP-CI.
  • Figure 263 depicts the GC/MS spectra of CSE.
  • Figure 264 depicts the GC/MS spectra of RCSE.
  • Figure 265 depicts the GC/MS spectra of RCSE-MRP-CI.
  • Figure 266 depicts a graphical representation of the time/intensity profile of NHDC and thaumatin and combinations thereof.
  • Figure 267 depicts a graphical representation of sweetness intensity and mouth-feel of combinations with NHDC and Combination of GSGs and SGs.
  • Figure 268 depicts a graphical representation of time/intensity profile of combinations with NHDC and Combination of GSGs and SGs.
  • Figure 269 depicts a graphical representation of time/intensity profile of combinations with NHDC and Combination of GSGs and SGs.
  • Figure 270 depicts a graphical representation of the sweetness intensity, lingering and mouth-feel of combinations with NHDC and Combination of GSGs and SGs/EPCalin.
  • Figure 271 depicts a graphical representation of the time/intensity profile of combinations with NHDC and Combination of GSGs and SGs/EPCalin.
  • Figure 272 depicts a graphical description of a Summary View of the sweetness time/intensity profile of the stevia-derived MRP samples with thaumatin in place of an amino acid.
  • Figure 273 depicts a graphical description of the sweetness time/intensity profile of the stevia-derived MRP samples with thaumatin in place of an amino acid for selected heating times.
  • Figure 274 depicts a graphical description of the sweetness time/intensity profile of the stevia-derived MRP samples with thaumatin in place of an amino acid for selected heating times.
  • Figure 275 depicts a graphical description of the sensory test results for the flavor (odor) of stevia-derived MRPs (Lys/Fru/Zo) with increased heating time.
  • Figure 276 depicts a graphical description of the sensory test results for the flavor (odor) of stevia-derived MRPs (Lys/Xyl/Zo) with increased heating times.
  • Figure 277 depicts a graphical description of sensory test results for the taste of stevia-derived MRPs (Lys/Fru/Zo) with increased heating time.
  • Figure 278 depicts a graphical description of sensory test results for the taste of stevia-derived MRPs (Lys/Xyl/Zo) with increased heating times.
  • Figure 279 depicts a comparison of added amounts of stevia-derived MRPs (Lys/Fru/ZO) with different heating times and the perceived added sweetness.
  • Figure 280 depicts a comparison of added amounts of stevia-derived MRPs (Lys/Fru/ZO) with different heating times and the perceived added sweetness.
  • Figure 281 depicts a comparison of added amounts of stevia-derived MRPs (Lys/Xyl/ZO) with different heating times and the perceived added sweetness.
  • Figure 282 depicts a comparison of added amounts of stevia-derived MRPs (Lys/Xyl/ZO) with different heating times and the perceived added sweetness.
  • Figure 283 depicts a comparison of added amounts of stevia-derived MRPs (Lys/Fru/ZO) with different heating times and the perceived added sweetness.
  • Figure 284 depicts a comparison of added amounts of stevia-derived MRPs (Lys/Xyl/ZO) with different heating times and the perceived added sweetness.
  • Figure 285 depicts a graphical representation of sensory test results for varying ratios of lysine: fructose.
  • Figure 286 depicts a graphical representation of sensory test results for varying ratios of SGA (Combination of GSGs and SGs) added to fixed ratio of lysine: fructose.
  • Figure 287 depicts Chromatogramme (TIC) and Mass spectra for the reaction of Reb-A and Alanine (reflux heating for 4 hours in ethanol) .
  • Figure 288 depicts Chromatogramme (TIC) and Mass spectra for the reaction of Reb-A and Glycine (reflux heating for 4 hours in ethanol) .
  • Maillard reaction refers to a non-enzymatic reaction of (1) one or more reducing and/or non-reducing sugars, and (2) one or more amine donors in the presence of heat, wherein the non-enzymatic reaction produces a Maillard reaction product and/or a flavor.
  • this term is used unconventionally, since it accommodates the use of use of non-reducing sweetening agents as substrates, which were not heretofore believed to serve as subtrates for the Maillard reaction.
  • reaction mixture refers to a composition comprising at least one amine donor and one sugar donor, wherein the reaction mixture is to be subjected to a Maillard reaction; a “reaction mixture” is not to be construed as the reaction contents after a Maillard reaction has been conducted, unless otherwise noted.
  • sucrose refers to a sweet-tasting, soluble carbohydrate, typically used in consumer food and beverage products.
  • sucrose donor refers to a sweet-tasting compound or substance from natural or synthetic sources, which can participate as a substrate in a Maillard reaction with an amine group-containing donor molecule.
  • amine donor refers to a compound or substance containing a free amino group, which can participate in a Maillard reaction.
  • sweetener generally refers to a consumable product, which produces a sweet taste when consumed alone.
  • sweeteners include, but are not limited to, high-intensity sweeteners, bulk sweeteners, sweetening agents, and low sweetness products produced by synthesis, fermentation or enzymatic conversion methods.
  • high-intensity sweetener refers to any synthetic or semi-synthetic sweetener or sweetener found in nature.
  • High-intensity sweeteners are compounds or mixtures of compounds which are sweeter than sucrose.
  • High-intensity sweeteners are typically many times (e.g., 20 times and more, 30 times and more, 50 times and more or 100 times sweeter than sucrose) .
  • sucralose is about 600 times sweeter than sucrose
  • sodium cyclamate is about 30 times sweeter
  • Aspartame is about 160-200 times sweeter
  • thaumatin is about 2000 times sweeter then sucrose (the sweeteness depends on the tested concentration compared with sucrose) .
  • High-intensity sweeteners are commonly used as sugar substitutes or sugar alternatives because they are many times sweeter than sugar but contribute only a few to no calories when added to foods. High-intensity sweeteners may also be used to enhance the flavor of foods. High-intensity sweeteners generally will not raise blood sugar levels.
  • high intensity natural sweetener refers to sweeteners found in nature, typically in plants, which may be in raw, extracted, purified, refined, or any other form, singularly or in combination thereof. High intensity natural sweeteners characteristically have higher sweetness potency, but fewer calories than sucrose, fructose, or glucose.
  • High intensity natural sweeteners include, but are not limited to, sweet tea extracts, stevia extracts, swingle extracts, sweet tea components, steviol glycosides, mogrosides, glycosylated sweet tea extracts, glycosylated stevia extracts, glycosylated swingle extracts, glycosylated sweet tea glycosides, glycosylated steviol glycosides, glycosylated mogrosides, licorice extracts, glycyrrhizic acid, including mixtures, salts and derivatives thereof.
  • high intensity synthetic sweetener or “high intensity artificial sweetener” refers to high intensity sweeteners that are not found in nature.
  • High intensity synthetic sweeteners include “high intensity semi-synthetic sweeteners” or “high intensity semi-artificial sweeteners” , which are synthesized from, artificially modified from, or derived from, high intensity natural sweeteners.
  • high intensity synthetic sweeteners include, but are not limited to, sucralose, aspartame, acesulfame-K, neotame, saccharin and aspartame, glycyrrhizic acid ammonium salt, sodium cyclamate, saccharin, advantame, neohesperidin dihydrochalcone (NHDC) and mixtures, salts and derivatives thereof.
  • sweetening agent refers to a high intensity sweetener.
  • the term “bulk sweetener” refers to a sweetener, which typically adds both bulk and sweetness to a confectionery composition and includes, but is not limited to, sugars, sugar alcohols, sucrose, commonly referred to as “table sugar, ” fructose, commonly referred to as “fruit sugar, ” honey, unrefined sweeteners, syrups, such as agave syrup or agave nectar, maple syrup, corn syrup and high fructose corn syrup (or HFCS) .
  • sweetener enhancer refers to a compound (or composition) capable of enhancing or intensifying sensitivity of the sweet taste.
  • sweetener enhancer is synonymous with a “sweetness enhancer, ” “sweet taste potentiator, ” “sweetness potentiator, ” and/or “sweetness intensifier. ”
  • a sweetener enhancer enhances the sweet taste, flavor, mouth feel and/or the taste profile of a sweetener without giving a detectable sweet taste by the sweetener enhancer itself at an acceptable use concentration.
  • the sweetener enhancer provided herein may provide a sweet taste at a higher concentration by itself. Certain sweetener enhancers provided herein may also be used as sweetening agents.
  • Sweetener enhancers can be used as food additives or flavors to reduce the amounts of sweeteners in foods while maintaining the same level of sweetness. Sweetener enhancers work by interacting with sweet receptors on the tongue, helping the receptor to stay switched “on” once activated by the sweetener, so that the receptors respond to a lower concentration of sweetener. These ingredients could be used to reduce the calorie content of foods and beverages, as well as save money by using less sugar and/or less othersweeteners. Examples of sweetener enhancers include, but are not limited to, brazzein, miraculin, curculin, pentadin, mabinlin, thaumatin, and mixtures thereof.
  • sweetening agents or sweeteners can be used as sweetener enhancers or flavors when their dosages in food and beverage are low.
  • sweetener enhancers can be utilized as sweeteners where their dosages in foods and beverages are higher than dosages regulated by FEMA, EFSA or other related authorities.
  • low sweetness products produced by synthesis, fermentation or enzymatic conversion refers to products that have less sweetness or similar sweetness than sucrose.
  • low sweetness products produced by extraction, synthesis, fermentation or enzymatic conversion method include, but are not limited to, sorbitol, xylitol, mannitol, erythritol, trehalose, raffinose, cellobiose, tagatose, DOLCIA PRIMA TM allulose, inulin, N-- [N- [3- (3-hydroxy-4-methoxyphenyl) propyl] -alpha-aspartyl] -L-phenylalanine 1-methyl ester, glycyrrhizin, and mixtures thereof.
  • “sugar alcohols” or “polyols” are sweetening and bulking ingredients used in manufacturing of foods and beverages. As sugar substitutes, they supply fewer calories (about a half to one-third fewer calories) than sugar, are converted to glucose slowly, and are not characterized as causing spiked increases in blood glucose levels.
  • Sorbitol, xylitol, and lactitol are exemplary sugar alcohols (or polyols) . These are generally less sweet than sucrose, but have similar bulk properties and can be used in a wide range of food and beverage products. In some case, their sweetness profile can be fine-tuned by being mixed together with high-intensity sweeteners.
  • glycoside refers to a molecule in which a sugar (the “glycone” part or “glycone component” of the glycoside) is bonded to a non-sugar (the “aglycone” part or “aglycone component” ) via a glycosidic bond.
  • terpenoid are used interchangeably with reference to a large and diverse class of organic molecules derived from terpenes, more specifically five-carbon isoprenoid units assembled and modified in a variety of ways and classified in groups based on the number of isoprenoid units used in group members.
  • terpenoids includes hemiterpenoids, monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids and polyterpenoids.
  • terpenoid glycoside and “terpenoid sweetener” refer to a compound having a terpenoid aglycone linked by a glycosidic bond to a glycone.
  • exemplary terpenoid glycosides include steviol glycosides, stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, rebaudioside I, rebaudioside J, rebaudioside K, rebaudioside L, rebaudioside M, rebaudioside N, rebaudioside O, dulcoside A, steviolbioside, rubusoside, glycosylated steviol glycosides, glucosylated steviol glycosides, as well as any other steviol glycoside (s) found in Stevia rebaudiana plant; Luo Han Guo extract
  • steviol glycoside a glycoside of steviol, a diterpene compound shown in Formula I, which is found in Stevia leaves.
  • Non-limiting examples of steviol glycosides are shown in Tables A or B below.
  • the steviol glycosides for use in the present application are not limited by source or origin. Steviol glycosides may be extracted from Stevia leaves, synthesized by enzymatic processes or chemical syntheses, or produced by fermentation.
  • rebaudioside A, ” “Reb A, ” and “RA” are equivalent terms referring to the same molecule. The same condition applies to all lettered rebaudiosides.
  • steviol glycoside composition and “SG composition” are used interchangeably with reference to a composition comprising one or more SGs.
  • Stevia extract refers to a plant extract from Stevia that contains varying percentages of SGs.
  • glycosylated steviol glycoside and “GSG” are used interchangeably with reference to an SG containing one or more additional glucose residues added relative to the parental SGs (including partially glycosylated steviol glycosides) present in e.g., Stevia leaves.
  • a “GSG” may be produced from any known or unknown SG by enzymatic synthesis, chemical synthesis or fermentation. It should be understood that GSG (s) essentially contain a glycosylated steviol glycoside (s) , but may also contain unreacted steviol glycosides, dextrins and other non-steviol glycoside substances when using extracts in the starting materials. It should also be understood that the GSG (s) can be purified and/or separated into purified/isolated components.
  • glycosylated steviol glycoside composition or “GSG composition” refer to any material comprising one or more GSGs.
  • SG/GSG composition refers to a generic composition that may comprise one or more SGs and/or one or more GSGs.
  • SG component ” “SG-containing component, ” “SG-containing composition, ” “SG-containing product, ” “Stevia sweetener” and “SG sweetener” are used interchangeably with reference to a component, composition, product or sweetener that contains one or more steviol glycosides and/or one or more glycosylated steviol glycosides.
  • non-SG component “non-SG-containing component” , “non-SG-containing composition” , “non-SG-containing product” , “non-Stevia sweetener” , “non-SG sweetener” and “non-Stevia sweetening agent” are used with reference to a component, composition, product, sweetener or sweetening agent that does not contain a steviol glycoside or a glycosylated steviol glycoside.
  • total steviol glycosides refers to the total amount of SGs and/or SGs in a composition.
  • YYxx refers to a composition, where YY refers to a given (such as RA) or collection of compounds (e.g., SGs) , where "xx" is typically a percent by weight number between 1 and 100 denoting the level of purity of a given compound (such as RA) or collection of compounds, where the weight percentage of YY in the dried product is equal to or greater than xx.
  • YYxx+WWzz refers to a composition, where each one of “YY” and “WW” refers to a given compound (such as RA) or collection of compounds (e.g., SGs) , and where each of "xx” and “zz” refers to a percent by weight number between 1 and 100 denoting the level of purity of a given compound (such as RA) or collection of compounds, where the weight percentage of YY in the dried product is equal to or greater than xx, and where the weight percentage of WW in the dried product is equal to or greater than zz.
  • RAx refers to a Stevia composition containing RA in amount of ⁇ x%and ⁇ (x+10) %with the following exceptions: the acronym “RA100” specifically refers to pure RA; the acronym “RA99.5” specifically refers to a composition where the amount of RA is ⁇ 99.5 wt %, but ⁇ 100 wt %; the acronym “RA99” specifically refers to a composition where the amount of RA is ⁇ 99 wt %, but ⁇ 100 wt %; the acronym “RA98” specifically refers to a composition where the amount of RA is ⁇ 98 wt %, but ⁇ 99 wt %; the acronym “RA97” specifically refers to a composition where the amount of RA is ⁇ 97 wt %, but ⁇ 98 wt %; the acronym “RA95” specifically refers to a composition where the amount of RA is ⁇ 95 wt %, but ⁇ 97 wt %; the acronym “RA95
  • Stevia extracts include, but are not limited to, including, but are not limited to RA20, RA40, RA50, RA60, RA80, RA 90, RA95, RA97, RA98, RA99, RA99.5, RB8, RB10, RB15, RC15, RD6, and combinations thereof.
  • GSG-RAxx refers to a GSG composition prepared in an enzymatically catalyzed glycosylation process with RAxx as the starting SG material. More generally, acronyms of the type “GSG-YYxx” refer to a composition of the present application where YY refers to a compound (such as RA, RB, RC or RD) , or a composition (e.g., RA20) , or a mixture of compositions (e.g., RA40+RB8) .
  • GSG-RA20 refers to the glycosylation products formed from RA20.
  • GX refers to a glycosyl group “G” where “X” is a value from 1 to 20 and refers to the number of glycosyl groups present in the molecule.
  • Stevioside G1 ST-G1
  • ST-G2 ST-G2
  • ST-G3 ST-G3
  • ST-G4 ST-G4
  • Stevioside G5 ST-G5
  • ST-G6 ST-G6
  • ST-G7 has seven (7) groups present
  • Stevioside G8 (ST-G8) has eight (8) glycosyl groups present
  • Stevioside G9 ST-G9) has nine (9) glycosyl groups present,
  • MRP Malverification reaction product
  • amine donor a sugar donor in the form of a reducing sugar, non-reducing sugar, or both
  • sugar donor comprises at least one carbonyl group.
  • the sugar donor includes at least one carbonyl group.
  • the MRP is a compound that provides flavor ( "Maillard flavor” ) , color ( “Maillard color” ) , or a combination thereof.
  • MRP composition refers to a composition comprising one or more MRPs produced by a Maillard reaction between an amine donor and a sugar donor in the form of a reducing sugar, non-reducing sugar, or both.
  • the sugar donor includes at least one carbonyl group.
  • the MRP is a compound that provides flavor ( "Maillard flavor” ) , color ( “Maillard color” ) , or a combination thereof.
  • steviol glycoside-derived MRP steviol glycoside-derived MRP
  • SG-derived MRP SG-derived MRP
  • S-MRP S-MRP-containing composition produced by a Maillard reaction between an amine donor and a sugar donor comprising a steviol glycoside, a glycosylated steviol glycoside, a Stevia extract and/or a glycosylated Stevia extract or combination thereof with or without an additional reducing sugar added to the reaction.
  • an S-MRP may be used interchangeably with the term “SG-MRP.
  • S-MRP or SG-MRP refers to an MRP composition in which (1) one steviol glycosides, glycosylated steviol glycosides, steviol extracts, and glycosylated steviol extracts, or combination thereof (2) an amine donor, and (3) a reducing sugar, are present in a reaction mixture subjected to the Maillard reaction.
  • thaumatin as used herein, is used generically with reference to thaumatin I, II, III, a, b, c, etc. and/or combinations thereof.
  • T-MRP refers to (1) a thaumatin-containing MRP composition produced by a Maillard reaction, wherein the reaction mixture comprises thaumatin and wherein thaumatin may be present in the beginning of the Maillard reaction or be added during the Maillard reaction, (2) a composition comprising an MRP prepared in the absence of thaumatin and additionally added thaumatin, or (3) a composition comprising a thaumatin-containing MRP composition and additionally added thaumatin.
  • sweetener-derived MRP or “sweetening agent-derived MRP” refers to an MRP or MRP-containing composition produced by a Maillard reaction between (1) an amine donor and (2) a sugar donor comprising a sweetener or a sweetening agent, respectively.
  • MRPs Meltiol
  • S-MRPs Stemmettyl-N-(2-aminoethyl)-N-(2-aminoethyl)-N-(2-aminoethyl)-N-(2-aminoethyl)-N-(2-aminoethyl)-N-(2-aminoethyl)-N-(2-aminoethyl) present, and/or mixtures thereof.
  • non-volatile refers to a compound having a negligible vapor pressure at room temperature, and/or exhibits a vapor pressure of less than about 2 mm. of mercury at 20 °C.
  • volatile refers to a compound having a measurable vapor pressure at room temperature, and/or exhibits a vapor pressure of, or greater than, about 2 mm. of mercury at 20 °C.
  • flavor and “flavor characteristic” are used interchangeably with reference to the combined sensory perception of one or more components of taste, odor, and/or texture.
  • flavoring agent e.g., a flavoring agent, “flavoring” and “flavorant” are used interchangeably with reference to a product added to food or beverage products to impart, modify, or enhance the flavor of food. As used herein, these terms do not include substances having an exclusively sweet, sour, or salty taste (e.g., sugar, vinegar, and table salt) .
  • salty taste e.g., sugar, vinegar, and table salt
  • natural flavoring substance refers to a flavoring substance obtained by physical processes that may result in unavoidable but unintentional changes in the chemical structure of the components of the flavoring (e.g., distillation and solvent extraction) , or by enzymatic or microbiological processes, from material of plant or animal origin.
  • synthetic flavoring substance refers to a flavoring substance formed by chemical synthesis.
  • enhancement includes augmenting, intensifying, accentuating, magnifying, and potentiating the sensory perception of a flavor characteristic without changing the nature or quality thereof.
  • modify includes altering, varying, suppressing, depressing, fortifying and supplementing the sensory perception of a flavor characteristic where the quality or duration of such characteristic was deficient.
  • the phrase “sensory profile” or “taste profile” is defined as the temporal profile of all basic tastes of a sweetener.
  • the onset and decay of sweetness when a sweetener is consumed, as perceived by trained human tasters and measured in seconds from first contact with a taster's tongue ( “onset” ) to a cutoff point (typically 180 seconds after onset) is called the “temporal profile of sweetness” .
  • a plurality of such human tasters is called a “sensory panel” .
  • sensory panels can also judge the temporal profile of the other “basic tastes” : bitterness, saltiness, sourness, piquance (aka spiciness) , and umami (aka savoriness or meatiness) .
  • the onset and decay of bitterness when a sweetener is consumed, as perceived by trained human tasters and measured in seconds from first perceived taste to the last perceived aftertaste at the cutoff point is called the “temporal profile of bitterness” .
  • sucrose equivalence is the amount of non-sucrose sweetener required to provide the sweetness of a given percentage of sucrose in the same food, beverage, or solution.
  • a non-diet soft drink typically contains 12 grams of sucrose per 100 ml of water, i.e., 12%sucrose. This means that to be commercially accepted, diet soft drinks must generally have the same sweetness as a 12%sucrose soft drink, i.e., a diet soft drink must have a 12%SE.
  • Soft drink dispensing equipment assumes an SE of 12%, since such equipment is set up for use with sucrose-based syrups.
  • off-taste refers to an amount or degree of taste that is not characteristically or usually found in a beverage product or a consumable product of the present disclosure.
  • an off-taste is an undesirable taste of a sweetened consumable to consumers, such as, a bitter taste, a licorice-like taste, a metallic taste, an aversive taste, an astringent taste, a delayed sweetness onset, a lingering sweet aftertaste, and the like, etc.
  • orally ingestible product refers to a composition comprising substances which are contacted with the mouth of man or animal, including substances which are taken into and subsequently ejected from the mouth and substances which are drunk, eaten, swallowed or otherwise ingested, and are safe for human or animal consumption when used in a generally acceptable range.
  • ppm parts per million
  • the Maillard reaction generally refers to a non-enzymatic browning reaction of a sugar donor with an amine donor in the presence of heat which produces flavor.
  • Common flavors produced as a result of the Maillard reaction include, for example, those associated with red meat, poultry, coffee, vegetables, bread crust etc. subjected to heat.
  • a Maillard reaction relies mainly on sugars and amino acids but it can also contain other ingredients including: autolyzed yeast extracts (AYE) , hydrolyzed vegetable proteins (HVP) , gelatin (protein source) , vegetable extracts (i.e. onion powder) , enzyme treated proteins, meat fats or extracts and acids or bases to adjust the pH of the reaction.
  • the reaction can be in an aqueous environment with an adjusted pH at specific temperatures for a specified amount of time to produce a variety of flavors.
  • Typical flavors include those associated with chicken, pork, beef, caramel, chocolate etc.
  • a wide variety of different taste and aroma profiles can be achieved by adjusting the ingredients, the temperature and/or the pH of the reaction.
  • the main advantage of the reaction flavors is that they can produce characteristic meat, burnt, roasted, caramellic, or chocolate profiles desired by the food industry, which are not typically achievable by using compounding of flavor ingredients.
  • Reducing groups can be found on reducing sugars (sugar donors) and amino groups can be found on amino donors such as free amino acids, peptides, and proteins.
  • a reactive carbonyl group of a reducing sugar condenses with a free amino group, with a concomitant loss of a water molecule.
  • a reducing sugar substrate for Maillard reaction typically has a reactive carbonyl group in the form of a free aldehyde or a free ketone.
  • the resultant N-substituted glycoaldosylamine is not stable.
  • the aldosylamine compound rearranges, through an Amadori rearrangement, to form a ketosamine.
  • Ketosamines that are so-formed may further react through any of the following three pathways: (a) further dehydration to form reductones and dehydroreductones; (b) hydrolytic fission to form short chain products, such as diacetyl, acetol, pyruvaldehyde, and the like, which can, in turn, undergo Strecker degradation with additional amino groups to form aldehydes, and condensation, to form aldols; and (c) loss of water molecules, followed by reaction with additional amino groups and water, followed by condensation and/or polymerization into melanoids.
  • Factors that affect the rate and/or extent of Maillard reactions include among others the temperature, water activity, and pH. The Maillard reaction is enhanced by high temperature, low moisture levels, and alkaline pH.
  • suitable carbonyl containing reactants include those that comprise a reactive aldehyde (--CHO) or keto (--CO--) group, such that the carbonyl free aldehyde or free keto group is available to react with an amino group associated with the reactant.
  • the reducing reactant is a reducing sugar, e.g., a sugar that can reduce a test reagent, e.g., can reduce Cu 2+ to Cu + , or can be oxidized by such reagents.
  • Monosaccharides, disaccharides, oligosaccharides, polysaccharides (e.g., dextrins, starches, and edible gums) and their hydrolysis products are suitable reducing reactants if they have at least one reducing group that can participate in a Maillard reaction.
  • Reducing sugars include aldoses or ketoses such as glucose, fructose, maltose, lactose, glyceraldehyde, dihydroxyacetone, arabinose, xylose, ribose, mannose, erythrose, threose, and galactose.
  • reducing reactants include uronic acids (e.g., glucuronic acid, glucuronolactone, and galacturonic acid, mannuronic acid, iduronic acid) or Maillard reaction intermediates bearing at least one carbonyl group such as aldehydes, ketones, alpha-hydroxycarbonyl or dicarbonyl compounds.
  • uronic acids e.g., glucuronic acid, glucuronolactone, and galacturonic acid, mannuronic acid, iduronic acid
  • Maillard reaction intermediates bearing at least one carbonyl group such as aldehydes, ketones, alpha-hydroxycarbonyl or dicarbonyl compounds.
  • MRPs Maillard Reaction Products
  • the Maillard reactants in a reaction mixture include an amino donor and a sugar donor in the form of a reducing sugar and/or a non-reducing sugar that are present as reactants.
  • the Maillard reaction products (MRPs) formed from these reactants encompass MRPs formed with or without sweeteners or sweetening agents.
  • S-MRPs Steviol Glycoside-Derived Maillard Reaction Products
  • the Maillard reactants in a reaction mixture include (1) an amino donor; and (2) a sugar donor comprising a steviol glycoside, a glycosylated steviol glycoside, a steviol extract, a glycosylated steviol extract, or combinations thereof.
  • the resulting products are referred to as steviol glycoside-derived MRPs, S-MRPs, or SG-MRPs.
  • S-MRPs or SG-MRPs are produced from a reaction mixture that comprises (1) one or more amine donors, (2) one or more reducing sugar, and (3) one or more steviol glycosides, glycosylated steviol glycosides, steviol extracts, and/or glycosylated steviol extracts.
  • the S-MRPs are formed under reaction conditions in which no reducing sugar is present.
  • MRP Maillard reaction product
  • SGs and SGEs have been surprisingly found to undergo a Maillard type reaction to provide MRPs and/or undergo caramelization (to produce caramelization reaction products (CRPs) ) , even though a ketone or aldehyde is not present in the sweetening agent.
  • steviol glycoside-derived Maillard reaction products can be formed.
  • the terms “steviol glycoside-derived MRP” , “SG-derived MRP” , and “S-MRP” are used interchangeably with reference to an MRP or MRP-containing composition produced by a Maillard reaction between an amine donor and one or more steviol glycosides, with or without the addition of reducing sugar (s) being added to the reaction mixture or reaction solution.
  • Additional high intensity natural sweetening agents for use in the present reactions and product compositions include sweet tea extracts (Rubus suavissimus S. Lee (Rosaceae) providing, for example rubusoside and suaviosides which are kaurane-type diterpene glycosides including suaviosides B, G, H, I and J) , swingle extracts (mogroside extracts) , glycosylated sweet tea extracts, glycosylated Stevia extracts, glycosylated swingle extracts, glycosylated sweet tea glycosides, glycosylated steviol glycosides, glycosylated mogrosides, neohesperidin dihydrochalcone (NHDC) , glycosylated NHDC, glycyrrhizin, glycosylated glycyrrhizin, hernandulcin, and mixtures thereof.
  • sweet tea extracts Rubus suavissimus S. Lee (Rosace
  • the MRP compositions of the present application include products preparable (or obtainable) by the reaction of an amine with a non-reducing sugar, for example, a high intensity natural sweetening agent, such as a steviol glycoside (SG) , a Stevia extract , a mogroside, a sweet tea extract, a glycosylated Stevia extract (GSG) , NHDC, etc.
  • a high intensity natural sweetening agent such as a steviol glycoside (SG) , a Stevia extract , a mogroside, a sweet tea extract, a glycosylated Stevia extract (GSG) , NHDC, etc.
  • the Maillard reactions described herein utilize an amine donor in combination with at least one sweetening agent (SA) (or natural high intensity sweetener) .
  • SA sweetening agent
  • SA-MRP synthetic high intensity sweetener
  • the terms “sweetening agent-derived MRP” and “SA-MRP” are used interchangeably with reference to an MRP or MRP-containing composition produced by a Maillard reaction between an amine donor and a sweetening agent, i.e., natural high intensity sweetener.
  • an S-MRP is a particular type of SA-MRP.
  • one or more carbohydrate sweeteners may be added to a reaction mixture subjected to the Maillard reaction. In other embodiments, one or more carbohydrate sweeteners may be added to an MRP composition.
  • carbohydrate sweeteners for use in the present application include caloric sweeteners, such as, sucrose, fructose, glucose, D-tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., ⁇ -cyclodextrin, ⁇ -cyclodextrin, and ⁇ -cyclodextrin) , ribulose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose,
  • caloric sweeteners
  • carbohydrate sweeteners are non-reducing sugars.
  • Sugars having acetal or ketal linkages are not reducing sugars, as they do not have free aldehyde chains. They therefore do not react with reducing-sugar test solutions (e.g., in a Tollens' test or Benedict's test) .
  • a non-reducing sugar can be hydrolyzed using dilute hydrochloric acid.
  • Exemplary carbohydrate sweeteners that are not reducing sugars include e.g., sucrose, trehalose, xylitol, and raffinose.
  • T-MRPs Thaumatin Containing MRPs
  • Thaumatin is a sweet-tasting protein that can serve as an amino donor in the Maillard reaction.
  • thaumatin is added to the reaction mixture subjected to the Maillard reaction or is added to an MRP composition produced with or without thaumatin.
  • Thaumatin is typically prepared from the katemfe fruit (Thaumatococcus daniellii Bennett) of West Africa. Wherever thaumatin is mentioned in this specification, it should be understood to apply to the use of thaumatin prepared from all types of katemfe fruit extracts or any other extracts, or from other plants and plant extracts, including genetically modified plants, as well as protein preparations derived from cell cultures or fermentation processes.
  • thaumatin in the Maillard reaction or added to an MRP composition formed therefrom can significantly improve the overall taste profile of food and beverages to have a better mouth feel, a creamy taste, a reduction of bitterness of other ingredients in food and beverage, such as astringency of tea, protein, or their extracts, acidic nature and bitterness of coffee, etc.
  • Thaumatin can also help to reduce lingering, bitterness and metallic aftertaste of natural, synthetic high intensity sweeteners, or their combinations, their combination with other sweeteners, with other flavors much more than thaumatin itself.
  • sweetening agents or sweeteners such as sucralose, acesulfame-K, aspartame, steviol glycosides, swingle extract, sweet tea extracts, allulose, sodium saccharin, sodium cyclamate or siratose.
  • malic acid can further improve the taste profile substantially, including less lingering.
  • Maillard reaction technology described herein may be used for the production of process or reaction flavors.
  • Process flavors are complex aroma building blocks, which provide similar aroma and taste properties as thermally treated foodstuffs such as cooked meat, chocolate, coffee, caramel, popcorn and bread. Additionally, they can be combined with other flavor ingredients to impart flavor enhancement and/or specific flavor notes in the applications in which they are used.
  • Such technology currently is mainly used for producing meat flavor and spiciness to enhance the taste of food. It is seldom considered as a tool to improve taste for the beverage industry.
  • Flavor can be characterized as a complex combination of the olfactory, gustatory and trigeminal sensations perceived during tasting.
  • the flavor can be influenced by tactile, thermal, painful and/or kinaesthetic effects.
  • flavor perception involves a wide range of stimuli, ii) the chemical compounds and food structures that activate the flavor sensors change as food is eaten, iii) the individual modalities interact in a complex way.
  • the Maillard reaction is one of the most important routes to flavor compounds in cooked foods.
  • the initial stages of the reaction involve the condensation of the carbonyl group of a reducing sugar with an amine compound, followed by the degradation of the condensation products to give a number of different oxygenated compounds.
  • the subsequent stages of the Maillard reaction involve the interaction of these compounds with other reactive components, such as amines, amino acids, aldehydes, hydrogen sulfide and ammonia.
  • These additional reactions lead to many important classes of flavor compounds including furans, pyrazines, pyrroles, oxazoles, thiophenes, thiazoles and other heterocyclic compounds.
  • the large number of different reactive intermediates that can be generated in the Maillard reaction gives rise to an extremely complex array of volatile products.
  • the Maillard reaction produces volatile substances (comprising pure and impure substances) and non-volatile substances (comprising pure and impure substances) .
  • the Maillard reaction products include various products that can be isolated, either partially volatile substances or partially non-volatile substances removed as a direct result of the Maillard reaction.
  • volatile compounds may be separated from non-volatile compounds at e.g., 105 °C, which represents a typical temperature to determine the dry mass of compounds.
  • dry mass may be interpreted as “compound-water-volatile compounds” .
  • Extraction with organic solvents generally provides a more complete profile of volatile metabolites including representation from polar hydrophilic species such as the lower molecular weight alcohols, hydroxyl-acids, thiols, and flavor compounds such as acetoin, methionol and furaneol.
  • polar hydrophilic species such as the lower molecular weight alcohols, hydroxyl-acids, thiols, and flavor compounds such as acetoin, methionol and furaneol.
  • non-volatile material such as leaf waxes, triterpenes, sterols, triglycerides and more complex lipids, and silicones and plasticizers from laboratory apparatuses are also likely to be extracted and may complicate analysis unless removed or the analytical method is suitably modified.
  • Solvents chosen to optimize the profile of extracted metabolites include pentane-ether mixtures and dichloromethane.
  • Unwanted interfering compounds such as lipids, pigments and hydrocarbons, may be removed by distillation (simultaneous distillation-extraction (SDE) , vacuum micro distillation or solvent assisted flavor evaporation (SAFE) , or by adsorption chromatography (solid phase extraction) .
  • SDE silictaneous distillation-extraction
  • SAFE solvent assisted flavor evaporation
  • adsorption chromatography solid phase extraction
  • Vacuum micro distillation using liquid nitrogen to distil and condense organic extracts under vacuum, also appears a useful technique to isolate volatile fractions suitable for instrumental analysis from complex matrices such as urine and faeces.
  • Atmospheric pressure (SDE) and steam distillation (hydrodistillation) methods used to prepare volatile extracts for GC-MS analysis are liable to artifact formation due to the use of heat.
  • Solvent extracts are routinely concentrated by evaporation before analysis, increasing sensitivity but resulting in selective loss of the more volatile metabolites as a function of the extent of the volume reduction. These losses may be compensated for by the use of internal standards which are generally added during sample extraction and are used to correct for any loss of volatiles that occurs during the process of sample preparation. Internal standards are generally more easily used with solvent extraction than with headspace methods. Since only a small portion (1 ⁇ L) of the final solvent extract is usually used for GC-MS analysis, solvent extraction methods offer less sensitivity than direct thermal desorption or SPME. Solvent extracts, prepared either by solvent extraction or elution of headspace sampling adsorbents provide the most convenient method of sample handling. Samples can be easily stored before analysis, introduction into the GC is readily and reliably automated, and there is usually sufficient sample for multiple analyses facilitating robust identification and quantification of both known and unknown volatiles.
  • SCF supercritical fluids
  • SCF supercritical carbon dioxide
  • SDE simultaneous distillation-extraction
  • profiling of volatile compounds can be achieved using gas chromatography mass spectrometry (GC-MS) .
  • GC may be coupled to detection by electron impact mass spectrometry (EI-MS) to provide high chromatographic resolution, sensitivity, compound-specific detection, quantification, and the potential to identify unknown volatiles by characteristic and reproducible fragmentation spectra in addition to their retention times on the gas chromatograph.
  • EI-MS electron impact mass spectrometry
  • Sample analysis can be simplified compared with silylation-based methods for the GC analysis of primary metabolites in that no chemical derivatization is required and the chromatograms generally contain fewer metabolites and less chemical noise.
  • a variety of commercial and web-based resources can be used to identify unknown compounds in a given volatile sample including large databases of searchable mass spectral libraries.
  • High-resolution time-of-flight GC-MS instruments enable highly accurate measurement of ion masses (m/z ratios) . This allows the calculation of chemical formulae and aids in the identification of unknown metabolites.
  • the use of chemical detectors other than the mass spectrometer, sulfur selective detectors or the human nose in gas chromatography-olfactometry (sniffer port, GC-O) may enable more specific and sensitive detection of particular metabolites.
  • Maillard reaction products may include water soluble and/or fat soluble compounds.
  • the Maillard reaction can be broken down into four stages.
  • the first stage involves the formation of glycosylamines.
  • the second stage involves rearrangement of the glycosylamines to form Amadori and Heyns rearrangement products (often abbreviated in the literature to "ARPs” and “HRPs” , respectively) .
  • the third stage involves dehydration and/or fission of the Amadori and Heyns rearrangement products to furan derivatives, reductones and other carbonyl compounds (which may have significant organoleptic qualities) .
  • These "third stage products” may also be produced without the formation of ARP's or HRP's.
  • the fourth stage involves the conversion of these furan derivatives, reductones and other carbonyl compounds into colored and aroma/flavor compounds.
  • products and reactants present in both the third and fourth stage of the Maillard reaction contribute towards aroma and/or flavor.
  • phosphate can be used as catalyst to help the conversion of Amadori compounds to flavor compounds.
  • Amadori rearrangement refers to an organic reaction describing the acid or base catalyzed isomerization or rearrangement reaction of the N-glycoside of an aldose or the glycosylamine to the corresponding 1-amino-1-deoxy-ketose.
  • the reaction is important in carbohydrate chemistry, specifically the glycation of hemoglobin (as measured by the HbA1c test) .
  • the rearrangement is usually preceded by formation of an ⁇ -hydroxyimine by condensation of an amine with an aldose sugar in a reaction known as Schiff base formation.
  • the rearrangement itself entails an intramolecular redox reaction, converting this ⁇ -hydroxyimine to an ⁇ -ketoamine.
  • the formation of imines is generally reversible, but subsequent to conversion to the keto-amine, the attached amine is fixed irreversibly.
  • the term “Amadori product” or “Amadori compound” refers to an intermediate in the Maillard reaction between a compound having a free amino group and a compound having a free aldehyde having a ketoamine structure represented by a general formula -- (CO) --CHR--NH-- (R represents a hydrogen atom or a hydroxyl group) .
  • the Amadori product is formed by a rearrangement of the Schiff base. Flavor compounds and other intermediates may be generated from Amadori products via different degradation pathways.
  • the MRP reaction products of the present application may include one or more detectable Amadori products in the final reaction products, as documented in Examples 281 and 282.
  • the intermediate analogous to the Amadori product is referred to as a “Heyn’s product” or “Heyn’s compound. ”
  • the Heyn’s product is formed by a rearrangement of the Schiff base. Flavor compounds and other intermediates may be generated from Heyn’s products via different degradation pathways.
  • the MRP reaction products of the present application may include one or more detectable Heyn’s products in the final reaction products.
  • the present application provides an MRP composition comprising one or more Amadori products.
  • the present application provides an MRP composition comprising one or more Heyn’s products.
  • MRP composition should be considered to further accommodate one or more Amadori products, one or more Heyn’s products or a combination thereof.
  • Reaction Scheme I illustrates a classical Maillard reaction between a reducing sugar and an amino group from an amino acid:
  • Reaction Scheme III illustrates the formation of a Schiff base (a very early Maillard reaction product) between an organic amine and a reducing sugar:
  • a composition of Maillard reaction products includes the raw materials for the reaction, the sugar donor and amine donor; and the finished Maillard products, which include MRP reactant products originating from the reaction between the sugar donor and the amine donor, as well as any unreacted reactants remaining after the reaction, i.e., sugar donors and amine donors.
  • the reactants may be completely or partially consumed.
  • Reaction Scheme IV illustrates a proposed reaction between a steviol glycosides and a free amino group:
  • the finished S-MRP products are comprised of two parts: (1) unreacted reactants, including sugar donor, amine donor, Stevia extract with or without non-steviol glycosides; (2) reactant resultants, including any resultants from the reaction of the sugar donor, amine donor, any resultant from reaction of steviol glycosides and the amino donor, any resultant from non-steviol glycosides exracted from leaves, or other typw of method to produce the steviol glycosides (e.g., fermentation, bioconversion) during the heated reaction of amine donors with or without sugar donors.
  • unreacted reactants including sugar donor, amine donor, Stevia extract with or without non-steviol glycosides
  • reactant resultants including any resultants from the reaction of the sugar donor, amine donor, any resultant from reaction of steviol glycosides and the amino donor, any resultant from non-steviol glycosides exracted from leaves, or other typw of method to produce the steviol glycosides (e.g., fermentation, bioconversion) during
  • the proposed Reaction IV is further applicable to other high intensity natural sweeteners that are not aldoses or ketoses, but have free carboxylic groups for reaction with an amine donor.
  • Maillard reaction products can be classified into four groups depending on their aroma type, chemical structure, molecular shape and processing parameters. These include, but are not limited to:
  • Cylic enolones of maltol or isomaltol, dehydrofuranones, dehydropyrones, cyclopentenolones are responsible for typically caramel like odors.
  • MRPs Maillard reaction products
  • MRPs include but are not limited to, for example, pyrazines, pyrroles, alkyl pyridines, acyl pyridines, furanones, furans, oxazoles, melanoidins, and thiophenes.
  • MRPs impart flavors such as nutty, fruity, caramel, meaty, or combinations thereof.
  • pyrazines provide cooked, roasted and/or toasted flavors.
  • Pyrroles provide cereal-like or nutty flavors.
  • Alkylpyridines provide bitter, burnt or astringent flavors.
  • Acylpyridines provide cracker-like or cereal flavors.
  • Furanones provide sweet, caramel or burnt flavors.
  • Furans provide meaty, burnt, or caramel-like flavors.
  • Oxazoles provide green, nutty or sweet flavors.
  • Thiophenes provide meaty or roasted flavors.
  • the Maillard reaction products (MRPs) produced may include, but are not limited to, (1) acyclic products, such as methional, phenylacetylaldehyde, 2-mercaptopropionic acid, (E) -2- ( (methylthio) methyl) but-2-enal glyoxal, butanedione, pyruvaldehyde, prop-2-ene-1, 1-diylbis (methylsulfane) , glyceraldehyde, 1, 3-dihydroxyacetone, acetoin and glycoladehyde; (2) cyclic products, such as cyclic products including 3, 5, 6-trimethyhlpyrazin-2 (1H) -one, 4, 5-dimethyl-2- (2- (methylthio) ethyl) oxazole and 1- (3H-imidazo [4, 5-c] pyridine-4-yl) ethan-1-one; (3) heterocyclic products such as 5- (hydroxymethyl) furan-2
  • MRPs can act as a coloring agent by optimization of reaction conditions.
  • the MRPs’ own color can be combined with natural colors to create new colors.
  • the MRPs can be blended with other colors to remove the unpleasant taste associated with the color/coloring agent.
  • Maillard reactions typically create a brownish color, which might not be desirable in certain applications.
  • the inventors of the present application have successfully developed a method to select optimized reactants and reaction condition for a desired color.
  • the final product may be prepared to provide good color, aroma, taste and texture. Suitable colors include, for example, red, orange, yellow, etc.
  • Maillard reaction flavors are also called process flavors.
  • the ingredients for reaction or process flavors can include (a) a protein nitrogen source, (b) a carbohydrate source, (c) a fat or fatty acid source and (d) other ingredients including herbs and spices; sodium chloride; polysiloxane acids; bases and salts such as pH regulators; water; the salts and acid forms of thiamine, ascorbic, citric, lactic, inosinic acid and guanylic acids; esters or amino acids; inositol; sodium and ammonium sulfides and hydrosulfides; diacetyl and lecithin.
  • the Maillard reactions described herein can be advantageously controlled to have only 1 st or the 2 nd reaction steps in the overall process if necessary.
  • the composition (s) would include the product (s) of the first step or from the second step.
  • the term “Maillard reaction” refers to a non-enzymatic reaction of (1) one or more reducing and/or non-reducing sugars, and (2) one or more amine donors in the presence of heat, wheren the non-enzymatic reaction produces a flavor.
  • this term is used unconventionally, since it accommodates the use of use of non-reducing sweetening agents as substrates, which were not heretofore believed to serve as subtrates for the Maillard reaction, such as sweet tea extracts (Rubus Suavissimus S.
  • Phenaceae providing, for example rubusoside and suaviosides which are kaurane-type diterpene glycosides including suaviosides B, G, H, I and J) , stevia extracts, swingle extracts (mogroside extracts) , glycosylated sweet tea extracts, glycosylated stevia extracts, glycosylated swingle extracts, glycosylated sweet tea glycosides, glycosylated steviol glycosides, glycosylated mogrosides, glycyrrhizine, glycosylated glycyrrhizinse or mixtures thereof could undergo a Maillard type reaction to provide MRPs like substances and/or caramelization to provide CRPs like substances even thought a ketone or aldehyde is not present in the sweetening agent.
  • compositions include products preparable (or obtainable) by the reaction of an amine with a non-reducing sugar, for example, a steviol glycoside, sweet tea extract (s) , glycosylated stevia extracts, etc., noted as sweetening agents herein.
  • a non-reducing sugar for example, a steviol glycoside, sweet tea extract (s) , glycosylated stevia extracts, etc.
  • sweetening agents include free carbonyl groups, such as free carboxyl groups, they do not have free aldehyde or free keto groups, characteristic of conventional “reducing sugars” or “caloric carbohydrate sweeteners” used in Maillard reactions.
  • Maillard reaction products can include the reaction products resulting from Maillard reactions between one or more donor amine (s) and one or more reducing sugar (s) , non-reducing sweetening agents and/or components from extracts, syrups, plants, etc. that provide a source of the reducing sugar (s) and/or the non-reducing sweetening agent (s) .
  • Steviol glycosides are not regarded as reducing sugars in the conventional sense, however, as further documented in the Examples, the inventors have surprisingly found that steviol glycosides can react with amine donors directly. Therefore, the inventors found that glycosides can act as sugar donor replacements with in a Maillard reaction with amine donors. In should be noted, however, that in certain instances steviol glycosides may be degraded to create reducing sugars which can react with amine donors in a conventional sense.
  • a composition of the present application can comprise one or more MRPs formed where the sugar donor (s) (or sweetening agent (s) ) comprise one or more glycosides.
  • the embodiments described herein can also provide the advantages of providing a “kokumi” taste.
  • the term “kokumi” is used for flavors that cannot be represented by any of the five basic taste qualities.
  • Kokumi is Japanese for “rich taste. ”
  • Kokumi is a taste sensation best known for the hearty, long finish it provides to a flavor.
  • Kokumi also provides a mouthful punch at initial taste, and lends an overall balance and richness to foods, like umami, kokumi heightens the sensation of other flavors. Therefore, kokumi helps developers respond to consumer demands for healthier products, by allowing a reduction of sodium, sugar, oil, fat or MSG content without sacrificing taste.
  • Kokumi can be classified into four profiles, namely thickness, continuity, mouthfulness and harmony of taste as well as long-lastingness.
  • Compounds with kokumi properties (such as peptides) increase the perception of other tastes, especially saltiness and umami; as such, with the same amount of salt, a food rich in these kokumi compounds will be perceived as saltier and more flavorful.
  • compositions described herein have a mouthful punch at initial quick on site sweet, and overall balance and richness, which make the sweetening agents more sugar-like and overcome the disadvantages of the sweetening agents having slow onset, void, bitterness, lingering, aftertaste etc.
  • steviol glycosides which are ent-kaurane-type diterpene glycosides
  • other constituents in high intensity natural sweeteners such as phytosterols, non-glycosylated sterebins A-N ent-labdanes glycosides, nonsweet steroid glycosides, lupeol esters, pigments, flavonoids, fatty acids, phospholipids, and glycolipids etc.
  • 30 to over 300 compounds have been detected within the essential and volatile oils of S. rebaudiana.
  • the inventors of the present application have surprisingly found that retention of some amount of these volatile substances, such as trans- ⁇ -farnesene, nerolidol, caryophyllene, caryophyllene oxide, limonene, spathulenol together with other sesqiterpenes, nonoxygenated sesquiterpenes, mono-terpenes could improve the taste profile of steviol glycosides and create unique pleasant flavors. These flavors could also exist in their intact form, react in Maillard reactions, and/or interact with other MRPs to create new, interesting flavors. For example, they can improve the overall taste profile of steviol glycosides and make them more acceptable for consumers.
  • these volatile substances such as trans- ⁇ -farnesene, nerolidol, caryophyllene, caryophyllene oxide, limonene, spathulenol together with other sesqiterpenes, nonoxygenated sesquiterpenes, mono-terpenes could improve the taste profile
  • non-reducing sugars may serve as substrates in the Maillard reaction and provide Maillard reaction product (MRP) compositions having improved taste profiles over previously reported high intensity natural sweetener compositions.
  • MRP Maillard reaction product
  • an MRP sweetening composition comprises one or more Maillard reaction products (MRPs) formed from a Maillard reaction between (1) a high intensity natural sweetening agent composition comprising one or more steviol glycosides, one or more Stevia extracts, or a combination thereof: and (2) an amine donor comprising a free amino group, wherein the amine donor is a primary amine compound, a secondary amine compound, an amino acid, a peptide, a protein, a protein extract, or a mixtures thereof.
  • MRPs Maillard reaction products
  • an MRP sweetening composition comprises one or more Maillard reaction products (MRPs) formed from a Maillard reaction mixture comprising (1) a high intensity natural sweetening agent composition in combination with a reactant mixture comprising (2) an amine donor comprising a free amino group and (3) a reducing sugar comprising a free aldehyde or free ketone group, wherein the high intensity natural sweetening agent composition comprises one or more steviol glycosides, one or more Stevia extracts, or a combination thereof, wherein the amine donor is a primary amine compound, a secondary amine compound, an amino acid, a peptide, a protein, a protein extract, or a mixtures thereof, and wherein the reducing sugar is a monosaccharide, disaccharide, oligosaccharide, polysaccharide, or a combinations thereof.
  • MRPs Maillard reaction products
  • an MRP sweetening composition comprises one or more MRP (s) and at least one sweetening agent or sweetener as defined in the present application.
  • amine reactant refers to a compound or substance containing a free amino group, which can participate in a Maillard reaction.
  • Amine containing reactants include amino acids, peptides (including dipeptides, tripeptides, and oligopeptides) , proteins, proteolytic or nonenzymatic digests thereof, and other compounds that react with reducing sugars and similar compounds in a Maillard reaction, such as phospholipids, chitosan, lipids, etc.
  • the amine reactant also provides one or more sulfur-containing groups.
  • Exemplary amine donors include amino acids, peptides, proteins, protein extracts.
  • amino acids include, for example, nonpolar amino acids, such as alanine, glycine, isoleucine, leucine, methionine, tryptophan, phenylalanine, proline, valine; polar amino acids, such as cysteine, serine, threonine, tyrosine, asparagine, and glutamine; polar basic (positively charged) amino acids, such as histidine and lysine; and polar acidic (negatively charged) amino acids, such as aspartate and glutamate.
  • nonpolar amino acids such as alanine, glycine, isoleucine, leucine, methionine, tryptophan, phenylalanine, proline, valine
  • polar amino acids such as cysteine, serine, threonine, tyrosine, asparagine, and glutamine
  • polar basic (positively charged) amino acids such as histidine and lysine
  • Exemplary peptides include, for example, hydrolyzed vegetable proteins (HVPs) and mixtures thereof.
  • HVPs hydrolyzed vegetable proteins
  • Exemplary proteins include, for example, sweet taste-modifying proteins, soy protein, sodium caseinate, whey protein, wheat gluten or mixtures thereof.
  • Exemplary sweet taste-modifying proteins include, for example, thaumatin, monellin, brazzein, miraculin, curculin, pentadin, mabinlin, and mixtures thereof.
  • the sweet-taste modifying proteins may be used interchangeably with the term “sweetener enhancer. ”
  • Exemplary protein extracts include yeast extracts, plant extracts, bacterial extracts and the like.
  • the nature of the amino donor can play an important role in accounting for the many flavors produced from a Maillard reaction.
  • the amine donor may account for one or more flavors produced from a Maillard reaction.
  • a flavor may be produced from a Maillard reaction by using one or more amine donors, or a particular combination of a amine donor and sugar donor.
  • the amine donor is present in the compositions described herein in a range of from about 1 to about 99 weight percent, from about 1 to about 50 weight percent, from about 1 to about 10 weight percent, from about 2 to about 9 weight percent, from about 3 to about 8 weight percent, from about 4 to about 7 weight percent, from about 5 to about 6 weight percent and all values and ranges encompassed over the range of from about 1 to about 50 weight percent.
  • the sugar donor may be a reducing sugar, a non-reducing sugar, or a combination thereof.
  • the MR reactants include one or more reducing sugars in combination with one or more amine donors.
  • a reaction mixture contains these reactants in the absence of non-reducing sugars (including high intensity natural sweeteners) an MRP composition is formed.
  • Reducing groups are found on reducing sugars. Initially, a reactive carbonyl group of a reducing sugar condenses with a free amino group, with a concomitant loss of a water molecule.
  • a reducing sugar substrate for the Maillard reaction typically has a reactive carbonyl group in the form of a free aldehyde (aldose) or a free ketone (ketose) .
  • the MR reactants include (1) one or more amine donors and (2) one more reducing sugars.
  • the MR reactants include (1) one or more amine donors and (2) one more non-reducing sugars.
  • the MR reactants include (1) one or more amine donors; (2) one more non-reducing sugars; and (3) one or more reducing sugars.
  • non-reducing sugar refers to a sugar or sweetening agent that does not contain free aldehyde or free keto groups.
  • exemplary non-reducing sugars include sucrose, trehalose, raffinose, stachyose, and verbascose.
  • exemplary non-reducing sweetening agents include high intensity natural sweetening agents.
  • the non-reducing sugars include one or more high intensity natural sweetening agents, which may be included as reactant (s) in the Maillard reaction or are added to MRP compositions formed therefrom.
  • the high intensity natural sweetening agents may comprise the only sugar donor (s) in the Maillard reaction mixture or they may be combined with one or more sweetening agents.
  • the natural and/or synthetic sweetening agents may be added to an MRP composition after completion of the MR reaction.
  • High-intensity natural sweeteners are commonly used as sugar substitutes or sugar alternatives, because they are many times sweeter than sugar, contribute only a few to no calories when added to foods, and enhance the flavor of foods. Because they are many times sweeter than table sugar (sucrose) , smaller amounts of high-intensity sweeteners are needed to achieve the same level of sweetness as sugar in food. Moreover, they generally will not raise blood sugar levels.
  • High intensity synthetic sweeteners are synthetically produced sugar substitutes or sugar alternatives that are similarly many times sweeter than sugar and contribute few to no calories when added to foods. Moreover, they can be similarly used as Maillard reaction components or as flavor enhancers added to MRP compositions of the present application. High intensity synthetic sweeteners include Advantame, Aspartame, Acesulfame potassium (Ace-K) , Neotame, Sucralose, and Saccharin.
  • Advantame can boost the flavor and taste profile of the compositions disclosed herein, especially when added after Maillard reaction.
  • Advantame and other high intensity synthetic sweeteners can be added in the range of 0.01ppm to 100 ppm.
  • the MR reactants include (1) one or more amine donors; and (2) one or more terpenoid glycosides with or without additional sweetening agents and/or reducing sugars.
  • the sugar donor may account for one or more flavors produced from a Maillard reaction. More particularly, a flavor may be produced from a Maillard reaction by using one or more sugar donors, wherein at least one sugar donor is selected from a product comprising a glycoside and a free carbonyl group.
  • glycosidic materials for use in Maillard reactions include natural concentrates/extracts selected from bilberry, raspberry, lingonberry, cranberry, apple, peach, apricot, mango, etc.
  • Reducing sugars can be derived from various sources for use as a sugar donor in the Maillard reaction or as a component added to an MRP composition.
  • a sugar syrup may be extracted from a natural source, such as Monk fruit, fruit juice or juice concentrate (e.g., grape juice, apple juice, etc. ) , vegetable juice (e.g., onion etc. ) , or fruit (e.g., apples, pears, cherries, etc. ) , could be used as sugar donor.
  • a syrup may include any type of juice regardless whether there is any ingredient being isolated from juice, such as purified apple juice with trace amount of malic acid etc.
  • the juice could be in the form of liquid, paste or solid.
  • Reducing sugars may also be extracted from Stevia, sweet tea, luohanguo, etc. after isolation of high intensity sweetening agents described herein (containing non-reducing sugars) from crude extracts and mixtures thereof.
  • the natural extracts used in Maillard reactions described herein can include any solvent extract-containing substances, such as polyphenols, free amino acids, flavonoids etc.
  • the extracts can be further purified by methods such as resin-enriched, membrane filtration, crystallization etc., as further described herein.
  • a Maillard reaction mixture or an MRP composition produced thereof may include a sweetener, thaumatin, and optionally one or more MRP products, wherein the sweetener is selected from date paste, apple juice concentrate, monk fruit concentrate, sugar beet syrup, pear juice or puree concentrate, apricot juice concentrate.
  • a root or berry juice may be used as as sugar donor or sweetener added to an MRP composition.
  • particular flavors may be produced from a Maillard reaction through the use of one or more sugar donors, where at least one sugar donor is selected from plant juice/powder, vegetable juice/powder, berries juice/powder, fruit juice/powder.
  • a concentrate or extract may be used, such as a bilberry juice concentrate or extract having an abundance of anthocyanins.
  • at least one sugar donor and/or one amine donor is selected from animal source based products, such as meat, oil etc. Meat from any part of an animal, or protein (s) from any part of a plant could be used as source of amino donor (s) in this application.
  • the sugar donor is present in the compositions described herein in a range of from about 1 to about 99 weight percent, from about 1 to about 50 weight percent, from about 1 to about 10 weight percent, from about 2 to about 9 weight percent, from about 3 to about 8 weight percent, from about 4 to about 7 weight percent, from about 5 to about 6 weight percent and all values and ranges encompassed over the range of from about 1 to about 50 weight percent.
  • the sugar donor is a reducing sugar or carbohydrate sweetener.
  • Reducing sugars for use in the present application include, for example, all monosaccharides and some disaccharides, which can be aldose reducing sugars or ketose reducing sugars.
  • the reducing sugar may be selected from the group consisting of aldotetrose, aldopentose, aldohexose, ketotetrose, ketopentose, and ketohexose reducing sugars.
  • aldose reducing sugars include erythrose, threose, ribose, arabinose, xylose, lyxose, allose, altrose, glucose, mannose, gulose, idose, galactose and talose.
  • ketose reducing sugars include erythrulose, ribulose, xylulose, psicose, fructose, sorbose and tagatose.
  • the aldose or the ketose may also be a deoxy-reducing sugar, for example a 6-deoxy reducing sugar, such as fucose or rhamnose.
  • Specific monosaccharide aldoses include, for example, reducing agents include, for example, Where at least one reducing sugar is a monosaccharide, or the one or more reducing sugars are selected from a group comprising monosaccharide reducing sugars, typically at least one monosaccharide reducing sugar is an aldose or a ketose
  • the reducing sugar is a monosaccharide
  • the monosaccharide may be in the D-or L-configuration, or a mixture thereof.
  • the monosaccharide is present in the configuration in which it most commonly occurs in nature.
  • the one or more reducing sugars may be selected from the group consisting of D-ribose, L-arabinose, D-xylose, D-lyxose, D-glucose, D-mannose, D-galactose, D-psicose, D-fructose, L-fucose and L-rhamnose.
  • the one or more reducing sugars are selected from the group consisting of D-xylose, D-glucose, D-mannose, D-galactose, L-rhamnose and lactose.
  • Specific reducing sugars include ribose, glucose, fructose, maltose, lyxose, galactose, mannose, arabinose, xylose, rhamnose, rutinose, lactose, maltose, cellobiose, glucuronolactone, glucuronic acid, D-allose, D-psicose, xylitol, allulose, melezitose, D-tagatose, D-altrose, D-alditol, L-gulose, L-sorbose, D-talitol, inulin, stachyose, including mixtures and derivatives therefrom.
  • Exemplary disaccharide reducing sugars for use in the present application include maltose, lactose, lactulose, cellubiose, kojibiose, nigerose, sophorose, laminarbiose, gentiobiose, turanose, maltulose, palantinose, gentiobiulose, mannobiose, melibiose, melibiulose, rutinose, rutinulose or xylobiose.
  • Mannose and glucuronolactone or glucuronic acid can be used as sugar donors under Maillard reaction conditions, although they have seldom been used.
  • Maillard reaction products of mannose, glucuronolactone or glucuronic acid provide yet another unique approach to provide new taste profiles with the sweetening agents described thoughout the specification alone or in combination with additional natural sweeteners, synthetic sweeteners, and/or flavoring agents described herein.
  • reducing sugars for use in the present application additionally include any of the carbohydrate sweeteners described above in Section II.
  • Terpenoid glycosides include steviol glycosides and other high intensity natural sweetening agents from plants, including glycosides, which may serve as sugar substitutes, and which are further described below.
  • a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond.
  • the sugar group is known as the glycone and the non-sugar group as the aglycone or genin part of the glycoside.
  • Glycosides are prevalent in nature and represent a significant portion of all the pharmacologically active constituents of botanicals. As a class, aglycones are much less water-soluble than their glycoside counterparts.
  • glycosides of the present application can be classified as ⁇ -glycosides or ⁇ -glycosides.
  • Some enzymes such as ⁇ -amylase can only hydrolyze ⁇ -linkages; others, such as emulsin, can only affect ⁇ -linkages.
  • linkages there are four types of linkages present between glycone and aglycone: a C-linked glycosidic bond, which cannot be hydrolyzed by acids or enzymes" ; an O-linked glycosidic bond; an N-linked glycosidic bond; or an S-linked glycosidic bond.
  • the glycone can consist of a single sugar group (monosaccharide) or several sugar groups (oligosaccharide) .
  • Exemplary glycones include glucose, galactose, fructose, mannose, rhamnose, rutinose, xylose, lactose, arabinose, glucuronic acid etc.
  • An aglycone is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom.
  • glycosides When combining a glycone with an aglycone, a number of different glycosides may be formed, including steviol glycosides, terpenoid glycosides, alcoholic glycosides, anthraquinone glycosides, coumarin glycosides, chromone glycosides, cucurbitane glycosides, cyanogenic glycosides, flavonoid glycosides, phenolic glycosides, steroidal glycosides, iridoid glycosides, and thioglycosides.
  • flavone aglycone refers to an unglycosylated flavonoid.
  • Flavonoid aglycones include flavone aglycones, flavanol aglycones, flavanone aglycones, isoflavone aglycones and mixtures thereof.
  • flavone aglycone refers to unglycosylated flavones, flavanols, flavanones and isoflavones, respectively.
  • the flavonoid aglycone may be selected from the group consisting of apigenin, luteolin, quercetin, kaempferol, myricetin, naringenin, pinocembrin, hesperetin, genistein, and mixtures thereof.
  • Terpenoid glycosides for use in the present application, include e.g., steviol glycosides, Stevia extracts , mogrosides (MGs) , Siraitia grosvenorii (luo han guo or monk fruit) plant extracts, rubusosides (RUs) , Rubus suavissimus (Chinese sweet tea) plant extracts; flavanoid glycosides, such as neohesperidin dihydrochalcone (NHDC) ; osladin, a sapogenin steroid glycoside from the rhizome of Polypodium vulgare; trilobatin, a dihydrochalcone glucoside from apple leaves; eriodictyol, a bitter-masking flavonoid glycoside extracted from yerba santa (Eriodictyon californicum) , one of the four flavanones extracted from this plant as having taste-modifying properties, along homoeriodict
  • terpenoid glycoside or high intensity natural sweetening agent such as an SG, a Stevia extract, a mogroside, a swingle extract, a sweet tea extract, NHDC, or any glycosylated derivative thereof, that the example is meant to be inclusive and applicable to all of the other terpenoid glycosides or high intensity natural sweetening agents in these classes.
  • sweetening agent such as a terpenoid glycoside sweetener, steviol glycoside sweetener, high intensity natural sweetener, sweetener enhancer, high intensity synthetic sweetener, reducing sugar, or non-reducing sugar, that the example is meant to be inclusive and applicable to all of the other sweeteners or sweetening agents in any given class.
  • Extracts from Stevia plants provide steviol glycosides ( “SGs” ) with varying percentages of components, SGs.
  • SGs steviol glycosides
  • RA rebaudioside A
  • RB rebaudioside B
  • RC rebaudioside C
  • RD rebaudioside D
  • RE rebaudioside E
  • RF rebaudioside F
  • RM rebaudioside M
  • RO rebaudioside O
  • RH rebaudioside H
  • RH rebaudioside I
  • RK rebaudioside J
  • rubusoside dulcoside A
  • DA dulcoside A
  • steviol glycoside As used herein, the terms “steviol glycoside, ” or “SG” refers to a glycoside of steviol, a diterpene compound shown in Formula I.
  • SGs are comprised of steviol molecules glycosylated at the C13 and/or C19 position (s) .
  • SGs Based on the type of sugar (i.e.glucose, rhamnose/deoxyhexose, xylose/arabinose) SGs can be grouped into three families (1) SGs with glucose; (2) SG with glucose and one rhamnose or deoxyhexose moiety; and (3) SGs with glucose and one xylose or arabinose moiety.
  • sugar i.e.glucose, rhamnose/deoxyhexose, xylose/arabinose
  • Table A provides a non-limiting list of about 80 SGs grouped according to the molecular weight.
  • the steviol glycosides for use in the present application are not limited by source or origin. Steviol glycosides may be extracted from Stevia leaves, synthesized by enzymatic processes, synthesized by chemical syntheses, or produced by fermentation. Steviol glycosides found in the Stevia plant include rebaudioside A (RA) , rebaudioside B (RB) , rebaudioside D (RD) , stevioside, rubusoside, as well as those in Table B (below) etc., and further includes mixtures thereof. The steviol glycoside of interest can be purified before use.
  • RA rebaudioside A
  • RB rebaudioside B
  • RD rebaudioside D
  • stevioside rubusoside
  • SG-1 to 16 SGs without a specific name
  • SG-Unk1-6 SGs without detailed structural proof
  • Glc Glucose
  • Rha Rhamnose
  • Xyl Xylose
  • Ara Arabinose.
  • SG-1 to 16 SGs without a specific name
  • SG-Unk1-6 Steviolglycosides without detailed structural proof
  • Glc Glucose
  • Rha Rhamnose
  • Xyl Xylose
  • Ara Arabinose
  • Fru Fructose
  • Gal Galactose
  • Steviol glycosides include a hydrophobic part (steviol) and a hydrophilic part (sugars, such as glucose) . When steviol glycosides are dissolved in a suitable solvent, steviol glycosides can form solvate (s) . It is assumed that steviol glycosides can form clusters similar with flavor molecules as they do for water and other solvents. Such structures can stabilize the flavor, especially volatile substances, either in an aqueous solution or in solid form. It has been found that three steviol glycosides share one water molecule in its crystal structure. Not to be limited by theory, it is believed that steviol glycosides share one or more flavor molecules which can stabilize the flavor molecule better than in the absence of the Stevia.
  • steviol glycosides improve the solubility of flavor substances. It is further believed that Stevia extracts and steviol glycosides have attractive forces to hold the flavor, protect the stability of flavor, and hereafter it is referred to as steviol glycoside flavorate (SGF) .
  • SGF steviol glycoside flavorate
  • One embodiment includes a composition comprising a Stevia extract with a flavor.
  • compositions of RA+RB, RA+RB+RD RA+RB+RC, RA+RB+RC+RD, RA+RB+RC+RD+RE, RA+RB+RC+RD+RM, RA+RD+RM, RD+RM+RO+RE, etc. are used. These combinations can be either added to Maillard reaction products produced from a sugar donor and an amine donor, or included in the Maillard reaction with the sugar donor and amine donor, or serve as the substrate (s) for the Maillard reaction in the presence of an amine donor.
  • steviol glycoside composition or “SG composition” refers to a composition comprising one or more SGs (steviol glycosides) .
  • the sugar donor (s) comprise a plurality of SGs in the form of a Stevia extract. Extracts from Stevia leaves, for example, provide SGs with varying percentages corresponding to the SGs present in a particular extract.
  • the phrase "steviol glycoside" is recognized in the art and is intended to include the major and minor constituents of Stevia.
  • These SGs include, for example, stevioside, steviolbioside, rebaudioside A (RA) , rebaudioside B (RB) , rebaudioside C (RC) , rebaudioside D (RD) , rebaudioside E (RE) , rebaudioside F (RF) , rebaudioside M (RM) , rebaudioside O (RO) , rebaudioside H (RH) , rebaudioside I (RI) , rebaudioside L (RL) , rebaudioside N (RN) , rebaudioside K (RK) , rebaudioside J (RJ) , rubusoside, dulcoside A (DA) , mixtures thereof, as well as those listed in Tables A and B.
  • RA steviolbioside
  • RA rebaudioside A
  • RB rebaudioside B
  • RC rebaudioside C
  • RD re
  • a Stevia extract may contain various combinations of individual SGs, where the extract may be defined by the proportion of a particular SG in the extract.
  • the extract may be defined by the proportion of a particular SG in the extract.
  • Table C An analysis of an exemplary RA50 extract prepared by the process described in Example 81 is shown in Table C.
  • An analysis of an exemplary combination extract comprising RA40+RB8 is shown in Table D.
  • the Stevia extract (s) included in the Maillard reaction or added to an MRP composition may be selected from the group consisting of RA20, RA40, RA50, RA60, RA80, RA 90, RA95, RA97, RA98, RA99, RA99.5, RB8, RB10, RB15, RC15, RD6, STV60, STV90, RA75/RB15, RA90/RD7, RA80/RB10/RD6 and combinations thereof.
  • the Stevia extract comprises non-steviol glycoside components.
  • Non-steviol glycoside components are volatile substances characterized by a characteristic odor and/or flavor, such as a citrus flavor and other flavors described herein.
  • the Stevia extract comprises a non-volatile type of non-steviol glycoside substances comprising one or more molecules characterized by terpene, di-terpene, or ent-kaurene structure.
  • the Stevia extract comprises one or more volatile and one or more non-volatile types of non-steviol glycoside substances.
  • the SGs can be fractionated to select for high molecular weight molecules.
  • the Stevia extract comprises 25-35 wt%Reb-A, 0.4-4 wt%Reb-B, 5-15 wt%Reb-C, 1-10 wt%Reb-D, 2-5 wt%Reb-F, 1-5 wt%Reb-K, and 20-40 wt%Stevioside.
  • the Stevia extract comprises one or more members selected from the group consisting of 1-5 wt%Rubusoside, 1-3 wt%Dulcoside A, 0.01-3 wt%steviolbioside, 0.2-1.5 wt%Dulcoside B, 00.01-2 wt%Reb-O, 0.01-2 wt %Reb-S, 0.01-1.2 wt %Reb-T, 0.01-0.8 wt%Reb-R, 0.01-0.7 wt%Reb-J, 0.01-0.7 wt%Reb-W, 0.01-0.7 wt%Reb-V, 0.01-0.6 wt%Reb-V2, 0.01-0.5 wt%Reb-G, 0.01-0.5 wt%Reb-H, 0.01-0.5 wt%Reb-K2, 0.01-0.5 wt%Reb-U2, 0.01-0.5 %Reb-I, 0.01-0.5 wt%Rel SG#
  • the Stevia extract comprises at least 20, at least 21, at least 22, at least 23 or at least 24 members selected from the group consisting of: 1-5 wt%Rubusoside, 1-3 wt%Dulcoside A, 0.01-3 wt%steviolbioside, 0.2-1.5 wt%Dulcoside B, 00.01-2 wt%Reb-O, 0.01-2 wt %Reb-S, 0.01-1.2 wt %Reb-T, 0.01-0.8 wt%Reb-R, 0.01-0.7 wt%Reb-J, 0.01-0.7 wt%Reb-W, 0.01-0.7 wt%Reb-V, 0.01-0.6 wt%Reb-V2, 0.01-0.5 wt%Reb-G, 0.01-0.5 wt%Reb-H, 0.01-0.5 wt%Reb-K2, 0.01-0.5 wt%Reb-U2, 0.01-0.5 %Reb-I
  • the Stevia extract comprises 45-55 wt%Reb-A, 20-40 wt%Stevioside, 2-6 wt%Reb-C, 0.5-3 wt%Reb-B, and 0.5-3 wt%Reb-D.
  • the Stevia extract comprises one or more members selected from the group consisting of: 0.1-3 wt%Related SG#5, 0.05-1.5 wt%Reb-R1, 0.0.05-1.5 wt%Reb-K2, 0.05-1.5 wt%Reb-E, 0.01-1 wt%Dulcoside A, 0.01-1 wt%Dulcoside B, 0.01-1 wt%Rubusoside, 0.01-1 wt%Steviolbioside, 0.01-1 wt%Iso-steviolbioside, 0.01-1 wt%Stevioside-B, 0.01-1 wt%Related SG#3, 0.01-1 wt%Related SG#2, 0.01-1 wt%Reb-G, 0.01-1 wt%Reb-F, and 0.01-1 wt%Reb-W.
  • the Stevia extract comprises at least 12, at least 13, at least 14 or at least 15 members selected from the group consisting of: 0.1-3 wt%Related SG#5, 0.05-1.5 wt%Reb-R1, 0.0.05-1.5 wt%Reb-K2, 0.05-1.5 wt%Reb-E, 0.01-1 wt%Dulcoside A, 0.01-1 wt%Dulcoside B, 0.01-1 wt%Rubusoside, 0.01-1 wt%Steviolbioside, 0.01-1 wt%Iso-steviolbioside, 0.01-1 wt%Stevioside-B, 0.01-1 wt%Related SG#3, 0.01-1 wt%Related SG#2, 0.01-1 wt%Reb-G, 0.01-1 wt%Reb-F, and 0.01-1 wt%Reb-W.
  • the Stevia extract comprises 35-45 wt%Reb-A, 10-25 wt%Stevioside, 4-12 wt%Reb-B, 4-12 wt%Dulcoside A, 0.5-4 wt%Reb-C, and 0.1-4 wt%Reb-O.
  • the Stevia extract comprises one or more members selected from the group consisting of: 0.3-3 wt%Rubusoside, 0.1-3 wt%Reb-D, 0.1-3 wt%Reb-G, 0.1-3 wt%Reb-I, 0.1-3 wt%Stevioside B, 0.1-3 wt%Related SG#3, 0.05-1.5 wt%Reb-E, 0.05-2 wt%Reb-R, 0.05-1 wt%Dulcoside B, 0.01-1 wt%Reb-N, 0.01-1 wt%Reb-Y, 0.01-1 wt%Steviolbioside, 0.01-1 wt%Dulcoside B, and combinations thereof.
  • the Stevia extract comprises at least 10, at least 11, at least 12 or at least 13 members selected from the group consisting of: 0.3-3 wt%Rubusoside, 0.1-3 wt%Reb-D, 0.1-3 wt%Reb-G, 0.1-3 wt%Reb-I, 0.1-3 wt%Stevioside B, 0.1-3 wt%Related SG#3, 0.05-1.5 wt%Reb-E, 0.05-2 wt%Reb-R, 0.05-1 wt%Dulcoside B, 0.01-1 wt%Reb-N, 0.01-1 wt%Reb-Y, 0.01-1 wt%Steviolbioside, and 0.01-1 wt%Dulcoside B.
  • compositions of stevia derived MRP (s) and/or also the Stevia derived MRP (s) and non-steviol glycosides contained within the stevia leaves/extracts include compositions of stevia derived MRP (s) and/or also the Stevia derived MRP (s) and non-steviol glycosides contained within the stevia leaves/extracts.
  • the steviol glycosides and non-steviol glycoside are extracted directly from leaves together.
  • the steviol glycosides and non-steviol glycosides may be blended following separate extraction (s) and/or separation (s) , and then blended back together.
  • the non-stevia glycoside substances can be obtained by fermentation or enzymatic conversion.
  • the non-steviol glycoside substances can be used as substrates for the Maillard reaction.
  • the inventors of the present application have developed an extraction process from the Stevia plant so as to preserve unique flavors, such as citrus (or tangerine) .
  • unique citrus (or tangerine) flavor originates from one or more flavor substances in the Stevia extract.
  • the flavor substances may be water soluble or they may be dispersible in an oil-in-water solution or Stevia flavorate, where the flavor threshold value can be as low as 10 -9 ppb.
  • a composition of steviol glycoside (s) and flavor substances originate from a Stevia extract.
  • Flavored Stevia extracts may be prepared by processes further described in the Examples.
  • Exemplary flavors that may be formed from the Stevia extracts include floral, caramel, citrus, chocolate, orange, violet, nectar, peach, jujube, barbecue, green tea, toast, roast barley, and combinations thereof.
  • Suitable FEMA recognized Stevia based compositions are included herein as noted in Table E. These Stevia based compositions can be used in the Maillard reaction as described throughout as the sweetening agent (s) .
  • GSGs Glycosylated Steviol Glycosides
  • the sugar donor (s) comprise one or more glycosylated steviol glycosides (GSGs) originating from one or more SGs listed in Table A or Table B.
  • GSG refers to an SG containing additional glucose residues added relative to the parental (or native) SGs present in e.g., Stevia leaves.
  • the additional sugar groups can be added at various positions of the SG molecules.
  • a GSG may be produced from any known or unknown SG by enzymatic synthesis, chemical synthesis or fermentation.
  • the additional sugar groups are added in an enzymatically catalyzed glycosylation process.
  • the glycosylation of an SG can be determined by HPLC-MS as described herein (see e.g., Example 17.
  • GSGs may be obtained by enzymatic processes, for example, by transglycosylating stevia extract containing steviol glycosides, or by common known synthetic manipulation.
  • the GSGs comprise glycosylated stevia extract containing glycosylated steviol glycoside (s) and also comprises short chain compounds obtained by hydrolyzation of glycosylated product, as well as non-glycosylated components which are the residue of unreacted steviol glycosides, or unreacted components other than steviol glycosides contained in the stevia extract.
  • any of the SGs in Tables A-D for example, STB, ST, RA, RB, RC, RD, rebaudioside E (RE) , rebaudioside F (RF) , rebaudioside M (RM) , rubusoside and dulcoside A can be enzymatically modified to afford, for example, their corresponding multi-glycosylated glycosides as follows: Steviol-G1, Steviol-G2, Steviol-G3, Steviol-G4, Steviol-G5, Steviol-G6, Steviol-G7, Steviol-G8, Steviol-G9, STB-G1, STB-G2, STB-G3, STB-G4, STB-G5, STB-G6, STB-G7, STB-G8, STB-G9, RB-G1, RB-G2, RB-G3, RB-G4, RB-G5, RB-G6, RB-G7, RB-G8, RB-G9, RC-G1, RC-
  • G1 and G2 of steviol, STB, ST, RA, RB, RC, RD, RE, RF, RM, rubusoside and dulcoside A are shown below.
  • GSGs may originate from an SG selected from the group consisting of Reb-D, Reb-I, Reb-L, Reb-Q, and Reb-I2.
  • the resulting GSGs are included in the group consisting of GSG-5G-1, GSG-5G-2, GSG-5G-3, GSG-5G-4, and GSG-5G-5. These GSGs originate from the SG-5G group.
  • Table F depicts GSG groups corresponding to parental SGs with glucose ( “G” ; i.e., 2nd G after hyphen) moieties added thereto.
  • G glucose
  • GSG-1G-2 refers to an SG having one glucose added
  • “2” is the series number in the row of Table F.
  • G rhamnose or deoxyhexose
  • R rhamnose or deoxyhexose
  • Table H depicts GSG groups corresponding to parental SGs with glucose ( “G” ; i.e., 2nd G after hyphen) and one moiety of xylose or arabinose ( “X” ) added thereto.
  • the one or more GSGs comprise at least one GSG representing a further glycosylation product of an SG from Table A or Table B.
  • the one or more GSGs comprise at least one GSG representing a further glycosylation product of an SG selected from the group consisting of SvGn#1, SG-4, iso-steviolbioside, SvGn#3, rebaudioside R1, stevioside F, SG-Unk1, dulcoside B, SG-3, iso-rebaudioside B, iso-stevioside, rebaudioside KA, SG-13, stevioside B, rebaudioside R, SG-Unk2, SG-Unk3, rebaudioside F3, rebaudioside F2, rebaudioside C2, stevioside E, stevioside E2, SG-10, rebaudioside L1, SG-2, rebaudioside A3, iso-rebaudioside A2, rebaudioside
  • the one or more GSGs comprise one or more additional glucose moieties.
  • the one or more GSGs are selected from the group consisting of: GSG-1G-1, GSG-1G-2, GSG-1G-3, GSG-1G-4, GSG-1G-5, GSG-2G-1, GSG-2G-2, GSG-2G-3, GSG-2G-4, GSG-3G-1, GSG-3G-2, GSG-3G-3, GSG-4G-1, GSG-4G-2, GSG-5G-1, and combinations thereof.
  • the one or more GSGs comprise one or more additional glucose moieties and are selected from the group consisting of: GSG-3G-2, GSG-3G-3, GSG-3G-4, GSG-3G-7, GSG-3G-8, GSG-4G-1, GSG-4G-2, GSG-4G-3, GSG-4G-7, GSG-5G-1, GSG-5G-2, GSG-5G-3, GSG-5G-4, GSG-5G-5, GSG-6G-3, and combinations thereof.
  • the one or more GSGs comprise one or more rhamnose moieties, one or more deoxyhexose moieties, or a combination thereof.
  • the one or more GSGs are selected from the group consisting of: GSG-1G1R-1, GSG-1G1R-2, GSG-2G1R-1, GSG-1G1R-3, GSG-2G1R-2, GSG-3G1R-1, GSG-1G1R-4, GSG-2G1R-3, GSG-3G1R-2, GSG-4G-1R-1, GSG-1G1R-5-1, GSG-2G1R-4, GSG-3G1R-3a, GSG-3G1R-3b, GSG-4G1R-2, GSG-5G1R-1, and combinations thereof.
  • the one or more GSGs are selected from the group consisting of: GSG-3G1R-3a, GSG-3G1R-3b, GSG-4G1R-2, GSG-4G1R-3, GSG-4G1R-4, GSG-4G1R-6, GSG-5G1R-4, GSG-6G1R-1a, GSG-6G1R-1b, GSG-6G1R-2, and combinations thereof.
  • the one or more GSGs comprise one or more xylose moieties, arabinose moieties, or a combination thereof.
  • the one or more GSGs are selected from the group consisting of: GSG-1G1X-1, GSG-1G1X-2, GSG-1G1X-3, GSG-1G1X-4, GSG-2G1X-1, GSG-2G1X-2, GSG-2G1X-3, GSG-3G1X-1, GSG-3G1X-2, GSG-4G1X-1, and combinations thereof.
  • the one or more GSGs are selected from the group consisting of: GSG-3G1X-4, GSG-3G1X-5, GSG-4G1X-1, GSG-4G1X-2, GSG-4G1X-3, GSG-4G1X-4, and combinations thereof.
  • At least one of the one or more GSGs has a molecular weight less than equal to or less than 1128 daltons; less than equal to or less than 966 daltons; or less than equal to or less than 804 daltons.
  • At least one of the one or more GSGs has a molecular weight greater than 1128 daltons; equal to or greater than 1260 daltons; equal to or greater than 1422 daltons; equal to or greater than 1746 daltons; or equal to or greater than 1922 daltons.
  • the one or more GSGs may be present in the composition in a total amount of 0.1-99.5 %of the composition by weight. In some embodiments, the one or more GSGs comprise are 50-70%of the composition by weight or 55-65%of the composition by weight.
  • Glycosylated Stevia extracts may be derived from any Stevia extract (s) .
  • a non-limiting list of exemplary GSGs includes glycosylated Stevia extracts including, but not limited to, GSG-RA20, GSG-RA30, GSG-RA40, GSG-RA50, GSG-RA60, GSG-RA70, GSG-RA80, GSG-RA90, GSG-RA95, GSG-RA97, GSG- (RA50+RB8) , GSG- (RA30+RC15) , and GSG- (RA40+RB8) .
  • Different sugar donors such as glucose, xylose, rhamnose, etc. also can be obtained during degradation of different compositions of steviol glycosides. These combinations of sugar donors could react with different amino acid donors, thus creating many unique and surprisingly pleasant flavors. The reaction removes the typical grassy, bitter, void, lingering and aftertaste of steviol glycosides.
  • glycosylated steviol glycosides are obtained for example, by synthetic manipulation or by enzymatic processes. GSGs obtained by these methods are not naturally occurring steviol glycosides. The methods and GSGs found in KR10-2008-0085811 are herein incorporated by reference.
  • Stevioside G1 ST-G1
  • Stevioside G2 ST-G2
  • Stevioside G3 ST-G3
  • Stevioside G4 ST-G4
  • Stevioside G5 ST-G5
  • Stevioside G6 ST-G6
  • Stevioside G7 ST-G7
  • Stevioside G8 ST-G8
  • Stevioside G9 ST-G9
  • Rebaudioside A G1 (RA-G1) Rebaudioside A G2 (RA-G2)
  • Rebaudioside A G3 R-G3
  • Rebaudioside A G4 RA-G4
  • Rebaudioside A G5 R-G5
  • Rebaudioside A G6 R-G6
  • Rebaudioside A G7 R-G7
  • Rebaudioside A G8 R-G8
  • Rebaudioside A G9 R-G9
  • a suitable method to prepare glycosylated steviol glycosides can be found, for example, in Examples 1 and 2 of KR10-2008-0085811. It is also anticipated that other steviol glycosides, for example, steviolbioside, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, rebaudioside O, rebaudioside H, rebaudioside I, rebaudioside L, rebaudioside N, rebaudioside K, rebaudioside J, rubusoside and dulcoside A can be enzymatically modified to afford their corresponding multiple glycosylated glycosides: Steviol G1, Steviol G2 Steviol G3, Steviol G4, Steviol G5, Steviol G6, Steviol G7, Steviol G8, Steviol G9, Steviobioside G1, Steviobioside G2, Steviobioside G3, Steviobioside G4, Stevio
  • GSG-RA20, GSG-RA30, GSG-RA40, GSG-RA50, GSG-RA60, GSG-RA70, GSG-RA80, GSG-RA90, GSG-RA95, GSG-RA97, GSG- (RA50+RB8) , GSG- (RA30+RC15) , and GSG- (RA40+RB8) are GSGs which are used to be combined with steviol glycosides, such as RA, RB, RD, etc.
  • GSG-RA20 is typically prepared from RA20 as a key starting material
  • GSG-RA30 is typically prepared from RA30 as a key starting material
  • GSG-RA40 is typically prepared from RA40 as a key starting material
  • GSG-RA50 is typically prepared from RA50 as a key starting material
  • GSG-RA60 is typically prepared from RA60 as a key starting material
  • GSG-RA70 is typically prepared from RA70 as a key starting material
  • GSG-RA80 is prepared from RA80 as the key starting material
  • GSG-RA90 is typically prepared from RA90 as a key starting material
  • GSG-RA95 is typically prepared from RA95 as a key starting material
  • GSG-RA97 is prepared from RA97 as a key starting material.
  • each composition contains varying concentrations of GSGs and steviol glycosides, then each composition may have different taste profiles. It is envisioned that specific ratios of GSGs and steviol glycosides may have unique and beneficial physical and chemical properties that are unknown and have not been previously disclosed.
  • GSGs or GSG extracts can be combined with one or more of steviol, stevioside, steviolbioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, rebaudioside O, rebaudioside H, rebaudioside I, rebaudioside L, rebaudioside N, rebaudioside K, rebaudioside J, rubusoside and dulcoside A to provide suitable sweetening agent compositions.
  • steviol, stevioside, steviolbioside rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, rebaudioside O, rebaudioside H, rebaudioside I, rebaudioside L, rebaudioside N, reb
  • a GSG or GSGs such as any one or more of GSG-RA20, GSG-RA30, GSG-RA40, GSG-RA50, GSG-RA60, GSG-RA70, GSG-RA80, GSG-RA90, GSG-RA95, GSG-RA97, GSG- (RA50+RB8) , GSG- (RA30+RC15) , and GSG- (RA40+RB8) can be included in the compositions described herein at 1 %wt/wt, 2 %wt/wt, 3 %wt/wt, 4 %wt/wt, 5 %wt/wt, 6 %wt/wt, 7 %wt/wt, 8 %wt/wt.
  • the one or more steviol glycosides including steviol, stevioside, steviolbioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, rebaudioside O, rebaudioside H, rebaudioside I, rebaudioside L, rebaudioside N, rebaudioside K, rebaudioside J, rubusoside, and dulcoside A, as well as those included in Table 2, are contained in the sweetening agent composition.
  • SG steviol glycosides
  • the steviol glycosides of the compositions can make up 1 %wt/wt, 2 %wt/wt, 3 %wt/wt, 4 %wt/wt, 5 %wt/wt, 6 %wt/wt, 7 %wt/wt, 8 %wt/wt, 9 %wt/wt, 10 %wt/wt, 11 %wt/wt, 12 %wt/wt, 13 %wt/wt, 14 %wt/wt, 15 %wt/wt, 16 %wt/wt, 17 %wt/wt, 18 %wt/wt, 19 %wt/wt, 20 %wt/wt, 21 %wt/wt, 22 %wt/wt, 23 %wt/wt, 24 %wt/wt, 25 %wt/wt, 26 %wt/wt, 27 %wt/
  • the GSGs used in the present application are prepared as follows: i) dissolving a glucose-donor material in water to form a liquefied glucose-donor material; ii) adding a starting SG composition to liquefied glucose-donor material to obtain a mixture; iii) adding an effective amount of an enzyme to the mixture to form a reaction mixture, wherein the enzyme catalyzes the transfer of glucose moieties from the glucose-donor material to SGs in the starting SG composition, and incubating the reaction mixture at a desired temperature for a desired length of reaction time to glycosylate SGs with glucose moieties present in the glucose-donor molecule.
  • the reaction mixture can be heated to a sufficient temperature for a sufficient amount of time to inactivate the enzyme.
  • the enzyme is removed by filtration in lieu of inactivation.
  • the enzyme is removed by filtration following inactivation.
  • the resulting solution comprising GSG, residual SGs and dextrin is decolorized.
  • the resulting solution of GSG, residual SGs and dextrin is dried. In some embodiments, the drying is by spray drying.
  • step (i) comprises the substeps of (a) mixing a glucose-donor material with a desired amount of water to form a suspension, (b) adding a desired amount of enzyme to the suspension and (c) incubate the suspension at a desired temperature for a desired time to form liquefied glucose-donor material.
  • Starch can be a suitable substitute for dextrin (s) and/or dextrin (s) can be obtained by the hydrolysis of starch.
  • Mogrosides are defined by a family of triterpene-glycosides, which are present in the fruit of Siraitia grosvenorii (formerly called Momordica grosvenori) , a member of the Curcubitaceae (gourd) family, which is native to southern China and northern Thailand.
  • the fruit is also referred to as Luo Han Guo (luohanguo) or monk fruit. Luohanguo has been used in traditional Chinese medicine as a medicinal herb for treating cough and sore throat and is popularly considered, in southern China, to be a longevity aid.
  • the fruit is well-known for its sweet taste, which is attributed to the triterpine glycosides present in the fruit, as well as extracts from the fruit, which are commonly referred to as “swingle” extracts.
  • Gourd family also contain remarkably sweet components, including additional species of the genus Siraitia (e.g., S. siamensis, S. silomaradjae, S. sikkimensis, S. africana, S. borneensis, and S. taiwaniana) and the popular herb jiaogulan (Gynostemma pentaphyllum) .
  • Siraitia e.g., S. siamensis, S. silomaradjae, S. sikkimensis, S. africana, S. borneensis, and S. taiwaniana
  • the popular herb jiaogulan Gynostemma pentaphyllum
  • Extracts from the fruits of Siraitia grosvenorii also known as Momordica grosvenori (Swingle) , Luo Han Guo or monk fruit etc. provide a family of triterpene-glycosides and are referred to as mogroside (s) ( “MGs” ) throughout the specification.
  • the extracts include, for example, mogroside V, mogroside IV, siamenoside I, and 11-oxomogroside V.
  • Constituents of the mogroside extracts are referred to by the designation “MG” followed by symbol, such as “V” , therefore mogroside V is “MGV” .
  • Siamenoside I would be “SSI”
  • 11-oxomogroside V would be “OGV” .
  • mogroside is used with reference to a triterpene-glycoside that is recognized in the art and is intended to include the major and minor constituents from mogroside extracts.
  • Exemplary triterpene glycosides for use in the present application include mogrosides, such as mogroside II, mogroside IIIA, mogroside IIIE, mogroside IVA, mogroside IVE, siamenoside I, and 11-oxomogroside V.
  • mogrosides such as mogroside II, mogroside IIIA, mogroside IIIE, mogroside IVA, mogroside IVE, siamenoside I, and 11-oxomogroside V.
  • the juice or extract monk fruit includes mainly non-sugar natural sweeteners, the triterpenoid glycosides, which include mogroside V (esgoside) , mogroside IV, and D-mannitol.
  • the natural sweetness of them is 256-344, 126, and 0.55-0.65 times of that of sugar.
  • the juice/extract contains large amounts of glucose, 14%fructose, proteins, vitamin C, and 26 inorganic elements, such as manganese, iron, nickel, selenium, tin, iodine, molybdenum and others.
  • the juice/extract also includes fatty acids, such as linoleic acid, oleic acid, palmitic acid, stearic acid, palmitic acid, myristic acid, lauric acid, and decanoic acid.
  • monk fruit extracts can contain, for example, a mogroside, such as MGV, in an amount of 3%by weight, 5%by weight, 20%by weight, 40%by weight, 50%by weight, 60%by weight or higher but containing other mogrosides or non-mogrosides in the extracts.
  • a mogroside such as MGV
  • MGV mogroside
  • some other polysaccharides or flavonoids may be present.
  • the mogroside (s) of interest can be purified before use.
  • Glycosylated mogrosides or “GMGs” refer to mogrosides that are glycosylated at least at one or more positions in addition to those positions glycosylated in native form, and may be obtained, for example, by synthetic manipulation or by enzymatic processes.
  • swingle extract and “monk fruit extract” are used interchangeably herein.
  • glycosyltransferase preferably, CGTase enzyme (cyclodextringlycosyltransferase)
  • glycosylated mogrosides or glycosylated swingle extracts containing glycosylated mogrosides may further comprise short chain compounds obtained by hydrolyzation of glycosylated product and also comprise non-glycosylated ingredients which include the residues of non-reacted mogrosides, or unreacted components other than mogrosides contained in the swingle extract.
  • GMG (s) essentially contains glycosylated mogroside (s) , but also contains unreacted mogrosides, dextrin and other non-mogroside substances found in extracts. It should also be understood that the GMG (s) can be purified and/or separated into purified/isolated components.
  • a swingle extract containing mogrosides may be produced by the method of extracting the fruit of Siraitia grosvenorii (Swingle) with an alcohol, a mixture of alcohol and water, or water to obtain mixtures of mogrosides, then purified to provide desired mogrosides, such as mogroside V.
  • an exemplary method for producing a swingle extract containing mogrosides may involve: extraction of the fruit of Siraitia grosvenorii with an alcohol, a mixture of alcohol and water, or water to obtain the mogrosides (such as mogroside V etc. ) component ranging from about 0.1 %to 99%by weight of the extract.
  • the swingle extract contains about 10-90%by weight mogrosides.
  • the swingle extract contains about 20-80%by weight mogrosides.
  • the swingle extract contains about 30-70%by weight mogrosides.
  • the swingle extract contains about 40-60%by weight mogrosides.
  • a suitable process to obtain a monk fruit extract is provided as follows. Luo Han Guo fruit is extracted with water or a mixture of water/alcohol (ethanol or methanol) at a temperature of from about 40°C to about 80°C with the ratio of fruit to solvent being about 1: 10 to about 1: 20 (weight to volume) .
  • the liquid can be clarified by flocculation or membrane filtration followed by purification through a macroporous resin and ion exchange resin. Decolorization can be accomplished with activated carbon. Solids are then filtered and dried.
  • glycosylated mogroside V is produced by dissolving dextrin in water (reverse osmosis water) .
  • the ratio of GMGV to water is about 1: 10 (weight/volume, (w/v) ) .
  • the ratio of dextrin to mogrosides/extract is optimized in a ratio of between 100: 1 to 1: 100 with suitable ranges including 3: 1, 2: 1, 1.5: 1 and 1: 1.
  • the dextrin to swingle extract ratio is between 30: 70 and 70: 30.
  • CGTase enzyme is added to the mixture (ratio of GMGV to CGTase is about 20: 1 (w/v) and incubated at 60-70°C for a desired length of reaction time (typically from about 2 hours to about 72 hours, more preferably from about 8 hours to about 48 hours, even more preferably from about 12 hours to about 24 hours) to glycosylate mogrosides with glucose molecules derived from dextrin, wherein the added amount of CGTase by volume is about 0.1-0.5ml based on 1g mogrosides.
  • the ratio of GMGV to CGTase is from about 10: 1 to about 20: 1 w/v.
  • the reaction mixture is heated to 90-100°C for 30 minutes to inactivate the CGTase, which can then be removed by filtration.
  • the resulting solution of GMGs, residual mogroside and dextrin is decolored and spray dried.
  • amylase can be added to the mixture and the mixture is incubated at 70°C for a desired length of reaction time to shorten the length of glucose chain (s) in the GMG molecules.
  • Decolorization and/or spray drying the resulting mixture of GMG, residual mogrosides and dextrin can then be undertaken.
  • monk fruit extracts with Maillard reaction products described herein are particularly useful in the savory industry to improve overall taste.
  • Rubusoside (RU) a steviol glycoside, and kaurane-type diterpene glycosides, such as suaviosides B, G, H, I and J, constitute a variety of natural sweeteners found in leaves of the Chinese sweet tea plant (Rubus suavissimus S. Lee) .
  • Rubusoside is 200 times sweeter than cane sugar and is the main steviol glycoside found in the leaves of the sweet tea plant.
  • Sweet tea plant extracts contain rubusoside, as well as the aforementioned suaviosides.
  • glycosylated RU refers to a glycosylated rubusoside
  • glycosylated sweet tea extract refers to a R. suavissimus leaf extract containing glycosylated RU and/or glycosylated suaviosides B, G, H, I and J.
  • glycosylated compounds may be obtained by transglycosylating rubusoside or a sweet tea extract containing rubusoside and/or suaviosides so as to add glucose units, for example, one, two, three, four, five or more than five glucose units, to the native rubusoside or suavioside (s) by glycosyltransferase, preferably, CGTase enzyme (cyclodextringlycosyltransferase) .
  • CGTase enzyme cyclodextringlycosyltransferase
  • the resulting glycosylated sweet tea glycosylates include short chain compounds obtained by hydrolyzation of glycosylated product and may also include non-glycosylated ingredients which are residues of non-reacted rubusoside or suavioside (s) or unreacted components other than rubusoside or suavioside (s) contained in the sweet tea extract.
  • Neohesperidin and naringin are flavanone glycosides present in citrus fruits and grapefruit, and are responsible for the bitterness of citrus juices, along with limonin.
  • Neohesperidin, naringin, and their derivatives, such as neohesperidine chalcone, naringin chalcone, phloracetophenone, neohesperidine dihydrochalcone, naringin dihydrochalcone etc. (as further described herein) are good candidates for bitter or sweet enhancers, as they have been found to be effective in masking the bitter tastes of other compounds found in citrus, including limonin and naringin.
  • bitter orange also known as Seville orange, sour orange, bigarade orange, or marmalade orange refers to a citrus tree (Citrus ⁇ aurantium) and its fruit. It is native to Southeast Asia and has been spread by humans to many parts of the world. The bitter orange is believed to be a cross between Citrus maxima ⁇ Citrus reticulate.
  • neohesperidine dihydrochalcone is produced by extracting neohesperidin from the bitter orange, and then hydrogenating neohesperidin to make NHDC.
  • NHDC is roughly 1500-1800 times sweeter than sugar at threshold concentrations and about 340 times sweeter than sugar weight-for-weight.
  • glycosylated derivatives of NHDC prepared by enzymatic processes may be employed.
  • the flavanone glycosides are provided in the form a metal salts.
  • a metal salt of dihydrochalcone has the following formula:
  • R is selected from the group consisting of hydrogen and hydroxy
  • R' is selected from the group consisting of hydroxy, methoxy, ethoxy and propoxy
  • R" is selected from the group consisting of neohesperidoxyl, B-rutinosyl and ⁇ -D-glucosyl
  • M is a mono-or divalent metal selected from the group consisting of an alkali metal and an alkaline earth metal
  • n is an integer from 1 to 2 corresponding to the valence of the selected metal M.
  • Typical compounds of the above formula are the alkali or alkaline earth metal monosalts having the following structures:
  • Neohesperidin dihydrochalcone (Forumal I)
  • alkali metals include e.g., sodium, potassium, lithium, rubidium, caesium, and ammonium, while the term “alkaline earth metals” includes e.g., calcium, magnesium, strontium, barium, etc. These may be used as salts of dihydrochalcone, along with other alkali amino acids as counterpart ions. Thus, certain embodiments of the present application comprise the use of one or more salts of dihydrochalcone.
  • Glycyrrhizin (or glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of Glycyrrhiza glabra (liquorice) root.
  • Glycyrrhizin is obtained as an extract from licorice root after maceration and boiling in water.
  • Licorice extract provides a source of glycyrrhizin and is sold as a liquid, paste, or spray-dried powder. When used in specified amounts, it is approved for use as a flavor and aroma in manufactured foods, beverages, candies, dietary supplements, and seasonings. It is 30 to 50 times as sweet as sucrose (table sugar) .
  • glycosylated derivatives of glycyrrhizin prepared by enzymatic processes may be employed.
  • fatty acids can act as sugar donors in Maillard reactions in combination with Stevia extracts, amino acids, and optionally a reducing sugar, such as glucose. This was found by evaluating MRP products formed when subjecting a fatty acid and an amine donor, e.g., an amino acid, to the Maillard reaction.
  • a fatty acid or its derivative refers to aliphatic acid or aliphatic esters of aliphatic acid which can be used as sugar donor in Maillard reaction.
  • An exemplary, non-limiting list of fatty acids includes cinnamic acid, glyceryl stearate, lactic acid, linolenic acid, alpha-linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, stearidonic acid, eicosatetraenoic acid, linoleic acid, gamma-linolenic acid, dihommo-gamma-linolenic acid, arachidonic acid, eicosadienoic acid, docosadienoic acid, adrenic acid, docosapentaenoic acid and combinations thereof.
  • compositions can be prepared with the components discussed herein including sweet tea extracts, Stevia extracts, swingle extracts, MG (s) , SG (s) , as well as components of sweet tea extract (s) , GMG (s) , GSG (s) glycosylated sweet tea glycosylates, in combination with an amine donor, and optionally, in combination any of the sugar donors described herein, such as glucose, fructose or galactose.
  • suitable Maillard reaction components (along with one or more amine donors) to provide suitable ingestible compositions from a Maillard reaction process.
  • an amine donor (s) is used in the Maillard reaction under appropriate reaction conditions (a pH from about 2 to about 14, e.g., pH ⁇ 7, elevated temperature) to produce the resultant Maillard reaction product (s) .
  • a GMG or mixtures of GMGs (1) A GMG or mixtures of GMGs.
  • a GMG, a GSG and a sugar donor A GMG, a GSG and a sugar donor.
  • a GMG, an SG and a sugar donor A GMG, an SG and a sugar donor.
  • a GMG, an MG and a sugar donor A GMG, an MG and a sugar donor.
  • a GMG, a GSG, an SG and an MG (12) A GMG, a GSG, an SG and an MG.
  • a GMG, a GSG an SG and a sugar donor (13) A GMG, a GSG an SG and a sugar donor.
  • a GMG, a GSG, an MG and a sugar donor (14) A GMG, a GSG, an MG and a sugar donor.
  • a GMG, a GSG an SG, an MG and a sugar donor (15) A GMG, a GSG an SG, an MG and a sugar donor.
  • GSG glycosylated steviol glycoside
  • GSG glycosylated steviol glycoside
  • a swingle extract (mogroside extract) .
  • a sweet tea component e.g., rubusosides, suaviosides.
  • a steviol glycoside (SG) a glycosylated steviol glycoside (GSG) and a sugar donor.
  • the reactants for the Maillard reaction may include a number of different raw materials for producing MRP compositions.
  • the raw materials may be categorized into the following groups comprsing the following exemplary materials:
  • the present application contemplates the use of any one of a number of raw materials exemplified below to produce NATURAL PRODUCTS:
  • Xylose syrup arabinose syrup and rhamnose syrup manufactured from beech wood. Ardilla Technologies supply these along with natural crystalline L-xylose, L-arabinose and L-rhamnose. Xylose syrup may also be obtained from natural sources, such as the xylan-rich portion of hemicellulose, mannose syrup from ivory nut, etc. These and other types of syrup described herein can be used as sugar donors in the compositions described herein.
  • Thickeners such as gum arabic can be hydrolyzed with an organic acid or by enzyme hydrolysis to produce a mixture containing arabinose.
  • Arabinose could also be obtained from other wood-based or biomass hydrolysate.
  • Cellulose enzymes can also be used.
  • Jardox Meat and poultry extracts and stocks.
  • Kanegrade Fish powders, anchovy, squid, tuna and others.
  • the fat contains phospholipids and lecithin.
  • the proteins are coagulating proteins and their activity must be destroyed by hydrolysis with acid or by the use of proteases prior to use. This will also liberate amino acids and peptides useful in reaction flavors. (Allergen activity)
  • Meat digests can also add authenticity but they are usually not as powerful as yeast extracts and HVPs.
  • compositions disclosed herein can be purchased or made by processes known to those of ordinary skill in the art and combined (e.g., precipitation/co-precipitation, mixing, blending, grounding, mortar and pestle, microemulsion, solvothermal, sonochemical, etc. ) or treated as defined by the current invention.
  • Sweetener (s) including reducing sugars, non-reducing sugars, high intensity natural sweeteners, high intensity synthetic sweeteners, and sweet taste-modifying proteins, can be included in a Maillard reaction or they may be added to an MRP composition in an amount in the range of 1 to about 99 weight percent, from about 1 to about 75 weight percent 1 to about 50 weight percent, from about 1 to about 40 weight percent, from about 1 to about 30 weight percent, from 1 to about 20 weight percent, from about 1 to about 10 weight percent, from about 2 to about 9 weight percent, from about 3 to about 8 weight percent, from about 4 to about 7 weight percent, from about 5 to about 6 weight percent and all values and ranges encompassed over the range of from about 1 to about 99 weight percent including 5 weight percent, 10 weight percent, 15, weight percent, 20 weight percent including increments of 5, for example, through 95 weight percent, and alternatively from about 2 weight percent, 4 weight percent, 6 weight percent, including increments of 2, for example, through 98 weight percent.
  • the MR reactants or the MRP composition prepared therefrom includes at least one sweetener enhancer.
  • the ratio of the MR reactants to the at least one sweetener enhancer is between 20: 1 and 1: 1, between 15: 1 and 2: 1, between 10: 1 and 5: 1, or any ratio or any range derived from any of the aforementioned ratios.
  • Sweetener enhancer (s) may be present in the MRP reaction mixture or in the MRP composition in a range of from about 0.5ppm to about 1000ppm, from about 1ppm to about 900ppm, from about 2ppm to about 800ppm, from about 3ppm to about 700ppm from about 4ppm to about 600ppm, about 500ppm, and all values and ranges encompassed over the range of from about 0.5 ppm to about 1000 ppm, including 5 ppm, 10 ppm, 15 ppm, 20 ppm, including increments of 5, for example, through 1000 ppm, alternatively from about 2 ppm, including 4 ppm, 6 ppm, 8 ppm, 10 ppm, including increments of 2, for example, through 1000 ppm.
  • Thaumatin may be included in the composition, before, during, or after the Maillard reaction, in a range from 0.01 ppm to 99.9 wt %on the basis of the total weight of the composition, including all specific values in the range and all subranges between any two specific values.
  • thaumatin may be present in the composition in an amount of 0.1%, 0.5%, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%70%, 80%, 90%, 95%by weight of the composition or any range derived therefrom, as well as the subranges of 0.5-95 wt%, 1-90 wt%, 5-80 wt%, 10-70 wt%, 20-60 wt%or 30-50 wt%on the basis of the total weight of the composition.
  • NHDC may be included in the composition, with or without thaumatin, before, durng, or after the Maillard reaction in these same amounts.
  • the MRP composition comprises from 0.01 ppm to 99.9 wt%of thaumatin, one or more MRPs as prepared by the present embodiments, and optionally 0.1-99.9 wt%of a sweetening agent and/or 0.1-99.9 wt%of sweetener.
  • the MRP composition comprises from 0.01 ppm to 30 wt%of thaumatin, 0.01 ppm to 50 wt%of MRP as prepared by the present embodiments, and optionally 10-30 wt%of sweetening agent, and optionally 10-30 wt%of sweetener.
  • the ratio of thaumatin to the MRP or S-MRP may range from 1: 100 to 1: 0.67, based on pure thaumatin.
  • typical ratios (by weight) of thaumatin: (MRP/S-MRP) may range from 1: 1000 to about 1: 0.4, more preferably from about 1: 200 to about 1: 1. Similar ratios may be utilized when substituting or additionally incorporated NHDC.
  • thaumatin may be used in a Maillard reaction with e.g., suitable natural sweeteners, such as SGs, Stevia extracts, GSGs and/or glycosylated Stevia extracts.
  • suitable natural sweeteners such as SGs, Stevia extracts, GSGs and/or glycosylated Stevia extracts.
  • NHDC may be ifurther combined in the reaction mixture.
  • the ratio of thaumatin to amino acid (s) may encompass exemplary ranges, such as 1: 2.64, 1: 0, and 1: 2424, respectively.
  • Thaumatin, a protein can be used as an amino donor alone or in combination with other amino acid (s) .
  • the MR reactants or the MRP composition prepared therefrom includes at least one high intensity synthetic sweetener.
  • high intensity synthetic sweeteners include, but are not limited to sucralose, sorbitol, xylitol, mannitol, sucralose, aspartame, acesulfame-K, neotame, erythritol, trehalose, raffinose, cellobiose, tagatose, DOLCIA PRIMA TM allulose, inulin, N- [N- [3- (3-hydroxy-4-methoxyphenyl) propyl] -alpha-aspartyl] -L-phenylalanine 1-methyl ester, glycyrrhizin, sodium cyclamate, including salts thereof and combinations thereof.
  • the ratio of the MR reactants to the at least one high intensity synthetic sweetener is between 20: 1 and 1: 1, between 15: 1 and 2: 1, between 10: 1 and 5: 1, or any ratio or any range derived from any of the aforementioned ratios.
  • the MR reactants or the MRP composition prepared therefrom includes at least one at least one sweetener enhancer and at least one high intensity synthetic sweetener.
  • the ratio of the MR reactants to the combination of the sweetener enhancer (s) and the high intensity synthetic sweetener (s) is between 20: 1 and 1: 1, between 15: 1 and 2: 1, between 10: 1 and 5: 1, or any ratio or any range derived from any of the aforementioned ratios.
  • the inventors of the present application have also developed a unique process which could preserve useful flavor substances originating from Stevia plants and recovered in in the form of Stevia extracts. Such substances are further amplified in Maillard reactions involving SGs and Stevia extracts in combination with various amine donors as described herein.
  • the flavor substances in Stevia plants include but are not limited to alkanes, ketones, acids, aldehydes, hydrocarbons, alkenes, aromatics, esters, alcohols, aliphatics or amines.
  • the acids comprise Acetic acid, Propanoic acid, Pentanoic acid, Hexanoic acid, Trans 2-hexenoic acid, Heptanoic acid, Octanoic acid, (Z) -9-Octadecenoic acid, decahydro-1-Naphthalenecarboxylic acid, 2, 3-dihyd-9, 12, 15-Octadecatrienoic acid
  • the alcohols comprise 1-Azabicyclo [3.2.1] octan-6-ol, 2-Ethyl-1-dodecanol, (+) spathulenol, 1, 2, 3, 4, 4a, 7, 8, 8a-octahy-1-Naphthalenol
  • the aldehydes comprise Hexanal, 2, 4-
  • a flavoring agent other than a flavor derived from a Maillard reaction product as described herein, can be added to the compositions described herein before or after a Maillard reaction has been effected.
  • suitable flavoring agents include, for example, natural flavors, vitamins, such as vitamin C, artificial flavors, spices, seasonings, and the like.
  • Exemplary flavor agents include synthetic flavor oils and flavoring aromatics and/or oils, uronic acids (e.g., glucuronic acid and galacturonic acid) or oleoresins, essences, and distillates, and a combination comprising at least one of the foregoing.
  • top note agents may be added, which are often quite volatile, vaporizing at or below room temperature. “Top notes” are often what give foods their fresh flavors. Suitable top note agents include but are not limited to, for example, furfuryl mercaptan, methional, nonanal, trans, trans- 2, 4-decadienal, 2, 2'- (dithiodimethylene) difuran, 2-methyl-3-furanthiol, 4-methyl-5-thiazoleethanol, pyrazineethanethiol, bis (2-methyl-3-furyl) disulfide, methyl furfuryl disulfide, 2, 5-dimethyl-2, 5-dihydroxy-1, 4-dithiane, 95%, trithioacetone, 2, 3-butanedithiol, methyl 2-methyl-3-furyl disulfide, 4-methylnonanoic acid, 4-methyloctanoic acid, or 2-methyl-3-tetrahydrofuranthi
  • Flavor oils include spearmint oil, cinnamon oil, oil of wintergreen (methyl salicylate) , peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil of nutmeg, allspice, oil of sage, mace, oil of bitter almonds, and cassia oil; useful flavoring agents include artificial, natural and synthetic fruit flavors, such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yuzu, sudachi, and fruit essences including apple, pear, peach, grape, raspberry, blackberry, gooseberry, blueberry, strawberry, cherry, plum, prune, raisin, cola, guarana, neroli, pineapple, apricot, banana, melon, apricot, cherry, tropical fruit, mango, mangosteen, pomegranate, papaya, and so forth.
  • useful flavoring agents include artificial, natural and synthetic fruit flavors, such as vanilla, and citrus oils including
  • Additional exemplary flavors imparted by a flavoring agent include a milk flavor, a butter flavor, a cheese flavor, a cream flavor, and a yogurt flavor; a vanilla flavor; tea or coffee flavors, such as a green tea flavor, an oolong tea flavor, a tea flavor, a cocoa flavor, a chocolate flavor, and a coffee flavor; mint flavors, such as a peppermint flavor, a spearmint flavor, and a Japanese mint flavor; spicy flavors, such as an asafetida flavor, an ajowan flavor, an anise flavor, an angelica flavor, a fennel flavor, an allspice flavor, a cinnamon flavor, a chamomile flavor, a mustard flavor, a cardamom flavor, a caraway flavor, a cumin flavor, a clove flavor, a pepper flavor, a coriander flavor, a sassafras flavor, a savory flavor, a Zanthoxyli Fructus flavor, a perilla flavor
  • any flavoring agent or food additive such as those described in "Chemicals Used in Food Processing” , Publication No 1274, pages 63-258, by the National Academy of Sciences, can be used. This publication is incorporated herein by reference.
  • flavoring agent or “flavorant” herein refers to a compound or an ingestibly acceptable salt or solvate thereof that induces a flavor or taste in an animal or a human.
  • the flavoring agent can be natural, semi-synthetic, or synthetic.
  • Suitable flavorants and flavoring agentt additives for use in the compositions of the present application include, but are not limited to, vanillin, vanilla extract, mango extract, cinnamon, citrus, coconut, ginger, viridiflorol, almond, bay, thyme, cedar leaf, nutmeg, allspice, sage, mace, menthol (including menthol without mint) , an essential oil, such as an oil produced from a plant or a fruit, such as peppermint oil, spearmint oil, other mint oils, clove oil, cinnamon oil, oil of wintergreen, or an oil of almonds; a plant extract, fruit extract or fruit essence from grape skin extract, grape seed extract, apple, banana, watermelon, pear, peach, grape, strawberry, raspberry, cherry, plum, pineapple, apricot, a flavoring agent comprising a citrus flavor, such as an extract, essence, or oil of lemon, lime, orange, tangerine, grapefruit, citron, kumquat, or combinations thereof.
  • Non-limiting examples of proprietary flavorants include Dohler TM Natural Flavoring Sweetness Enhancer K14323 (Dohler TM , Darmstadt, Germany) , Symrise TM Natural Flavor Mask for Sweeteners 161453 and 164126 (Symrise TM , Holzminden, Germany) , Natural Advantage TM Bitterness Blockers 1, 2, 9 and 10 (Natural Advantage TM , Freehold, New Jersey, U.S.A. ) , and Sucramask TM (Creative Research Management, Stockton, California, U.S.A. ) .
  • the flavoring agent is present in the composition of the present application in an amount effective to provide a final concentration of about 0.1 ppm, 0.5 ppm, 1 ppm, 2 ppm, 5 ppm, 10 ppm, 15 ppm, 20 ppm, 25 ppm, 30 ppm, 35 ppm, 40 ppm, 45 ppm, 50 ppm, 55 ppm, 60 ppm, 65 ppm, 70 ppm, 75 ppm, 80 ppm, 85 ppm, 90 ppm, 100 ppm, 110 ppm, 120 ppm, 130 ppm, 140 ppm, 150 ppm, 160 ppm, 170 ppm, 180 ppm, 190 ppm, 200 ppm, 220 ppm, 240 ppm, 260 ppm, 280 ppm, 300 ppm, 320 ppm, 340 ppm, 360 ppm, 380
  • the flavoring agent is present in the composition of the present application in an amount effective to provide a final concentration ranging from 10 ppm to 1000 ppm, from 50 ppm to 900 ppm, from 50 ppm to 600 ppm, from 50 ppm to 500 ppm, from 50 ppm to 400 ppm, from 50 ppm to 300 ppm, from 50 ppm to 200 ppm, from 75 ppm to 600 ppm, from 75 ppm to 500 ppm, from 75 ppm to 400 ppm, from 75 ppm to 300 ppm, from 75 ppm to 200 ppm, from 75 ppm to 100 ppm, from 100 ppm to 600 ppm, from 100 ppm to 500 ppm, from 100 ppm to 400 ppm, from 100 ppm to 300 ppm, from 100 ppm to 200 ppm, from 125 ppm to 600 ppm, from 125 ppm to 500 ppm, from 10 ppm to
  • the reaction mixture may include a pH regulator, which can be an acid or a base.
  • Suitable base regulators include, for example, sodium hydroxide, potassium hydroxide, baking powder, baking soda any useable food grade base salts including alkaline amino acids.
  • the Maillard reaction can be conducted in the presence of alkalinic amino acids without the need of an additional base where the alkaline amino acid serves as the base itself.
  • the pH of the reaction mixture can be maintained at any pH suitable for the Maillard reaction.
  • the pH is maintained at a pH of from about 2 to about 14, from about 2 to about 7, from about 3 to about 9, from about 4 to about 6, from about 7 to about 14, from about 8 to about 10, from about 9 to about 11, from about 10 to about 12, or any pH range derived from these integer values.
  • the reaction mixture contains less than 95 wt %, less than 90 wt %, less than 80 wt %, less than 70 wt %, less than 60 wt %, less than 50 wt %, less than 40 wt %, less than 30 wt %, less than 20 wt %, less than 15 wt %, or less than 10 wt % or less than 5 wt %, less than 1 wt %solvent.
  • the reaction temperature in any of the MRP reaction mixtures described in the present application may be 0°C, 5°C, 10°C, 20°C, 25°C, 30°C, 35°C, 40°C, 50°C, 55°C, 60°C, 65°C, 70°C, 80°C, 90°C, 100°C, 110°C, 120°C, 125°C, 130°C, 135°C, 140°C, 150°C, 155°C, 160°C, 165°C, 170°C, 180°C, 190°C, 200°C, 210°C, 220°C, 225°C, 230°C, 235°C, 240°C, 250°C, 255°C, 260°C, 265°C, 270°C, 280°C, 290°C, 300°C, 400°C, 500°C, 600°C, 700°C, 800°C, 900°C, 1000°C,
  • the reaction temperature in any of the MRP reaction mixtures described in the present application may range from 0°C to 1000°C, 10°C to 300°C, from 15°C to 250°C, from 20°C to 250°C, from 40°C to 250°C, from 60°C to 250°C, from 80°C to 250°C, from 100°C to 250°C, from 120°C to 250°C, from 140°C to 250°C, from 160°C to 250°C, from 180°C to 250°C, from 200°C to 250°C, from 220°C to 250°C, from 240°C to 250°C, from 30°C to 225°C, from 50°C to 225°C, from 70°C to 225°C, from 90°C to 225°C, from 110°C to 225°C, from 130°C to 225°C, from 150°C to 225°C, from 170°C to 225°C, from 190°C to 225°C, from
  • Maillard reaction (s) can be conducted either under open or sealed conditions.
  • the reaction time is generally from a few seconds to about 100 hours, more particularly from about a few minutes to about 24 hours, from about a few minutes to about 12 hours, from about a few minutes to about 8 hours, from a few minutes to about 5 hours, from about 10 minutes to about 1 hour, from about 20 minutes to about 40 minutes, from about 1 hour to about 3 hours, from about 2 hours to about 4 hours, or any time range thereof.
  • the reaction can be terminated at any time.
  • the Maillard reaction mixture can contain unreacted reactants, degraded substances from the reactants, pH regulator (s) , and/or salt (s) .
  • the Maillard reactions can be conducted at atmospheric pressure or under pressure.
  • the reaction mixture When conducted under pressure, the reaction mixture may be subjected to constant pressure or it may be subjected to varying pressures over time.
  • the pressure in the reaction vessel is at least 10 MPa, at least 20 MPa, at least 30 MPa, at least 40 MPa, at least 50 MPa, at least 75 MPa, at least 100 MPa, at least 150 MPa, at least 200 MPa, at least 250 MPa, at least 300 MPa, at least 400 MPa, at least 500 MPa, at least 600 MPa, at least 700 MPa, at least 800 MPa, and any pressure range derived from the aforementioned pressure values.
  • the use of low solubility-or insoluble amino acids in the Maillard reaction may result in insoluble reactants present in the final MRP composition.
  • filtration may be used to remove any insoluble components present in the MRP compositions.
  • any one of the high intensity natural sweetening agents described herein such as steviol, stevioside, steviolbioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, rebaudioside O, rebaudioside H, rebaudioside I, rebaudioside L, rebaudioside N, rebaudioside K, rebaudioside J, rubusoside, and dulcoside A, mogrosides, glycosylated mogrosides, GSGs, SGs, rubusosides, glycosylated rubusosides, suaviosides, glycosylated suaviosides, sweet tea extracts, glycosylated sweet tea extracts, as well as those included in Table A; high intensity synthetic sweetening agents described herein; any one of the sweetener enhancers described
  • the ratio of the high intensity natural sweetening agent to the one or more amino acids may be between 99: 1 and 85: 15, between 95: 5 and 90: 10, between 90: 10 and 85: 15, or any ratio or any range derived from any of the aforementioned ratios.
  • the ratio of the amino donors or amino acids to one another may range between 5: 1 and 1: 5, between 4: 1 and 1: 4, between 3: 1 and 1: 3, between 2: 1 and 1: 2, or any ratio or any range derived from any of the aforementioned ratios.
  • the components can have ratios of from 1: 99, 2: 98, 3: 97, 4: 96, 5: 95, 6: 94, 7: 93, 8: 92, 9: 91, 10: 90, 11: 89, 12: 88, 13: 87, 14: 86, 15: 85, 16: 84, 17: 83, 18: 82, 19: 81, 20: 80, 21: 79, 22: 78, 23: 77, 24: 76, 25: 75, 26: 74, 27: 73, 28: 72, 29: 71, 30: 70, 31: 69, 32: 68, 33: 67, 34: 66, 35: 65, 36: 64, 37: 63, 38: 62, 39: 61, 40: 60, 41: 59, 42: 58, 43: 57, 44: 56, 45: 55, 46: 54, 47: 53, 48: 52, 49: 51 and 50: 50, and
  • the different components can be sweeteners, non-nutritive sweeteners, individual components of sweeteners, such as RA, RB, RD, RM, etc., components of Stevia extracts, components of mogroside extracts, etc.
  • Ratios of Maillard reaction product (s) to sweetener enhancer (s) may range from e.g., 100: 1 to 1: 100 with all ratios therebetween, including for example 10: 1, 20: 1, 30: 1, 40: 1, 50: 1, 60: 1, 70: 1, 80: 1, 90: 1 and including integer values there between, including for example, 2: 1, 3: 1, 4: 1, 5: 1, 6: 1, 7: 1, 8: 1, 9: 1, 11: 1, 12: 1, etc.
  • the ratios are from 1: 10, 1: 20, 1: 30, 1: 40, 1: 50, 1: 60, 1: 70, 1: 80, 1: 90 and including integer values there between, including for example, 1: 2, 1: 3, 1: 4, 1: 5, 1: 6, 1: 7, 1: 8, 1: 9, 1: 11, 1: 12, etc.
  • the components can have ratios of from 1: 1: 98, 1: 2: 97, 1: 3: 96, 1: 4: 95, 1: 5: 94, 1: 6: 93, 1: 7: 92, 1: 8: 91, 1: 9: 90, 1: 10: 89, 1: 11: 88, 1: 12: 87, 1: 13: 86, 1: 14: 85, 1: 15: 84, 1: 16: 83, 1: 17: 82, 1: 18: 81, 1: 19: 80, 1: 20: 79, 1: 21: 78, 1: 22: 77, 1: 23: 76, 1: 24: 75, 1: 25: 74, 1: 26: 73, 1: 27: 72, 1: 28: 71, 1: 29: 70, 1: 30: 69, 1: 31: 68, 1: 32: 67, 2: 3:
  • the different components can be sweeteners, non-nutritive sweeteners, individual components of sweeteners, such as RA, RB, RD, RM, etc., components of Stevia extracts, components of mogroside extracts, etc.
  • compositions having only two or three different components e.g., SGs, MGs, GSGs, GMGs, non-nutritive sweeteners, etc. herein, and that the exemplary ratios are non-limiting. Rather, the same formula can be followed for establishing ratios of as many different components as are contained within a given composition.
  • a composition that comprises 20 different components described herein the components can have ratios of from 1: 1: 1: 1: 1: 1: 1: 1: 1: 1: 1: 1: 1: 1: 1: 1: 1: 81 to 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5: 5, and all possible combinations of ratios therebetween.
  • a composition of the present disclosure may have up to and including a combination of all compounds, for example but not limited to, those in Table 2.
  • one or more components may be added before, during, or after the Maillard reaction to a composition or product, or may be added to an MRP composition, or may be added to a consumable product, such as beverage product or food product, wherein any one of the components is present in any of the aforementioned composition (s) or product (s) at a parts-per-million (ppm) basis (or concentration) relative to the other contents in a composition or product, wherein the one or more components are selected from any one of the high intensity natural sweeteners described herein; any one of the high intensity synthetic sweeteners described herein; any one of the sweetener enhancers described herein; any one of the reducing sugars described herein; any one of the sweetening agents described herein; any one of the non-reducing sugars described herein; any one of the amine donors described herein; any one of the flavor substances described herein, or any of the additional additives described herein, such that any one of these component (s) is present in a
  • one or more components may be added before, during, or after the Maillard reaction to a composition or product, or may be added to an MRP composition, or may be added to a consumable product, such as beverage product or food product, wherein any one of the components is present in any of the aforementioned composition (s) or product (s) at a parts-per-million (ppm) basis (or concentration) relative to the other contents in a composition or product, wherein the one or more components are selected from any one of the high intensity natural sweeteners described herein; any one of the high intensity synthetic sweeteners described herein; any one of the sweetener enhancers described herein; any one of the reducing sugars described herein; any one of the sweetening agents described herein; any one of the non-reducing sugars described herein; any one of the amine donors described herein; any one of the flavor substances described herein, or any of the additional additives described herein, such that any one of these component (s) is present in a
  • final concentration refers to the concentration of, for example, any one of the aforementioned components present in any final composition or final orally consumable product (i.e., after all ingredients and/or compounds have been added to produce the composition or to produce the orally consumable product) .
  • one or more components may be added to the Maillard reaction or added to an MRP composition formed therefrom, wherein any one of the components is expressed in terms of its purity.
  • any one of the components may be characterized by a level of purity of about 50%to about 100%by weight, about 55%to about 100%by weight, about 60%to about 100%by weight, about 65%to about 100%by weight, about 70%to about 100%by weight, about 75%to about 100%by weight, about 80%to about 100%by weight, about 85%to about 100%by weight, about 86%to about 100%by weight, about 87%to about 100%by weight, about 88%to about 100%by weight, about 8
  • the purity of the component (w/w) may be at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 86%, at least 87%, at least 88%, at least 89%, at least 90%, at least 91%, at least 92%, at least 93%, at least 94%, at least 95%, at least 96%, at least 97%, at least 98%, at least 99%, at least 99.5%, at least 99.9%, at least 100%, or any any range defined by any two of the aforementioned values.
  • a general method to prepare Stevia derived Maillard reaction product (s) is described as follows. Briefly, an SG or Stevia extract is dissolved with or without a sugar donor, and together with amino acid donor in water, followed by heating of the solution at an elevated temperature, for example from about 50 to about 200 degrees centigrade.
  • the reaction time can be varied from more than one second to a few days, more generally a few hours, until Maillard reaction products (MRPs) are formed or the reaction components have been exhausted or the reaction has been completed, with or without formation of caramelization reaction products (CRPs) , which are further described below.
  • MRPs Maillard reaction products
  • CRPs caramelization reaction products
  • a pH adjuster or pH buffer can be added to regulate the pH of the reaction mixture before, during or after reaction as futher described herein.
  • the resultant solution is dried by spray dryer or hot air oven to remove the water and to obtain the MRP (s) .
  • Suitable solvents approved for oral use include, for example, alcohols, such as low molecular weight alcohols, e.g., methanol, ethanol, propanol, butanol, pentanol, hexanol, ethylene glycol, propylene glycol, butyl glycol, etc.
  • alcohols such as low molecular weight alcohols, e.g., methanol, ethanol, propanol, butanol, pentanol, hexanol, ethylene glycol, propylene glycol, butyl glycol, etc.
  • the following additional solvents may be used in the Maillard reaction or may act as carriers for Maillard reaction products: acetone, benzyl alcohol, 1, 3-butylene glycol, carbon dioxide, castor oil, citric acid esters of mono-and di-glycerides, ethyl acetate, ethyl alcohol, ethyl alcohol denatured with methanol, glycerol (glycerin) , glyceryl diacetate, glyceryl triacetate (triacetin) , glyceryl tributyrate (tributyrin) , hexane, isopropyl alcohol, methyl alcohol, methyl ethyl ketone (2-butanone) , methylene chloride, monoglycerides and diglycerides, monoglyceride citrate, 1, 2-propylene glycol, propylene glycol mono-esters and diesters, triethyl citrate, and mixtures thereof.
  • the Maillard reaction mixtures may further include one or more carriers (or flavor carriers) considered acceptable for use in flavoring agents are therefore suitable for use as solvents for the Maillard reaction: acetylated distarch adipate, acetylated distarch phosphate, agar agar, alginic acid, beeswax, beta-cyclodextrine, calcium carbonate, calcium silicate, calcium sulphate, candelilla wax, carboxymethyl cellulose, Na salt, carnauba wax, carrageenan, microcrystalline cellulose, dextran, dextrin, diammonium phosphate, distarch phosphate, edible fats, elemi resin, ethyl lactate, ethyl cellulose, ethyl hydroxyethyl cellulose, ethyl tartrate, gelatin, gellan gum, ghatti gum, glucose, glyceryl diacetate, glyceryl diesters of aliphatic
  • the amount of solvent is sufficient to dissolve the components or provide a heterogeneous mixture.
  • the amount of water to reaction products ratio is from about 100: 1 to about 1: 100, for example from about 6: 1, 1: 1 to about 1: 4.
  • Ratios for the Maillard reaction components to solvent are thus from 100: 1 to 1: 100, e.g., 1: 99 to 80: 20, with all ratios there between, including for example 10: 1, 20: 1, 30: 1, 40: 1, 50: 1, 60: 1, 70: 1, 80: 1, 90: 1 and including integer values there between, including for example, 2: 1, 3: 1, 4: 1, 5: 1, 6: 1, 7: 1, 8: 1, 9: 1, 11: 1, 12: 1, etc.
  • the ratios are from 1: 10, 1: 20, 1: 30, 1: 40, 1: 50, 1: 60, 1: 70, 1: 80, 1: 90 and including integer values there between, including for example, 1: 2, 1: 3, 1: 4, 1: 5, 1: 6, 1: 7, 1: 8, 1: 9, 1: 11, 1: 12, etc.
  • the product mixture does not need to be neutralized or it can be neutralized.
  • Water and/or solvent (s) do not necessarily need to be removed but can be removed by distillation, spray drying or other known methods if the product is desired as a powder or liquid, whatever the case may be.
  • the Maillard reaction products can include one or more of the following components after the reaction has occurred. These components include, for example, remaining sweetening agent (s) , remaining reducing sugar (sugar donor (s) ) , remaining amine donor (s) , degraded sweetening agent (s) ; degraded sugar donor (s) , degraded amine donor (s) , possible salt (s) that occur naturally from the Maillard reaction process and/or added salt (s) , remaining sweetener (s) , degraded sweetener (s) , remaining sweetener enhancer (s) , degraded sweetener enhancer (s) , MRP (s) , CRP (s) , additional MRP (s) added to the reaction product and/or additional CRP (s) added to the reaction product.
  • the Maillard reaction can be performed such that there can be an excess of amine donor (s) in comparison to reducing sugar (s) or much less than the amount of reducing sugar present.
  • the resultant Maillard reaction mixture would include remaining amine donor (s) , degraded amine donor (s) and/or residue (s) or amine donor (s) .
  • the amine donor (s) would be reacted during the course of the reaction.
  • the reducing sugar is replaced with a sweetening agent (e.g., a material such as a Stevia extract that does not include a reactive aldehydic or ketone moiety) and subjected to amine donor (s)
  • a sweetening agent e.g., a material such as a Stevia extract that does not include a reactive aldehydic or ketone moiety
  • the amine donor (s) may be present in amounts that would be fully consumed by a Maillard type reaction or be present in an amount that would provide excess amine donor (s) and consequently amine donor (s) , amine donor residue (s) and/or amine degradation product (s) would be present in the Maillard reaction mixture.
  • MRPs consist of volatile substances and non-volatile substances. By evaporating the volatile substances, purified non-volatile substances can be obtained. These non-volatile substances (or products) can be used as flavor modifiers or with the top note of final products.
  • MRPs include a composition including one or more volatile substances, one or more non-volatile substances or mixtures thereof.
  • Non-volatile substances in MRPs or isolated from MRPs can provide a good mouth feel, umami and Kukumi taste.
  • Stevia extracts and MRP compositions derived therefrom contain volatile and unvolatile terpine and/or terpinoid substances that can be further purified in order to obtain substance providing a tasteful, sweet and/or aromatic profile.
  • Treatment of Stevia extracts and S-MRP compositions using column chromatography, separation resins, and/or other separation methods, such as distillation, can be employed to retain most of the tasteful aroma terpine and/or terpinoid substances containing oxygen in the structure, while removing other unpleasant taste substances.
  • a Stevia extract can be enriched for the presence of aromatic terpene substances containing oxygen in the structure.
  • the inventors of the present application have found a way to enhance a citrus or tangerine taste by heat-treating a terpine-and/or terpinoid rich Stevia extract under acidic conditions comprising e.g., citric acid, tartaric acid, fumaric acid, lactic acid, malic acid etc., more preferably citric acid.
  • substances such as linalool can react with citric acid with or without Maillard reaction.
  • Vacuum distillation of fractions or column chromatography employing macroporous resins and/or silica gels, including ion exchange resins produced by Dow and Sunresin can be used for further purification.
  • the present application provides a composition comprising a tangerine (or citrus) flavored Stevia extract and method for producing the same as further described in the Examples.
  • a method to produce a citrus flavored Stevia extract involves a heat process with or without Maillard reaction under acid conditions, more preferably in a Maillard reaction with citric acid.
  • compositions comprising flavor substances from the Stevia plant or other natural sweetener plants described herein, including leaves, roots, seeds, etc. therefrom.
  • vanilla, maltol or other flavor modifier product can be added to the compositions described herein to further improve the taste.
  • FMPs such as maltol, ethyl-maltol, vanillin, ethyl vanillin, m-methylphenol, and m-n-propylphenol can further enhance the mouthfeel, sweetness and aroma of the MRP compositions described herein.
  • one or more FMPs may be added before or after the Maillard reaction, such as maltol, ethyl-maltol, vanillin, ethyl vanillin, m-methylphenol, m-n-propylphenol, or combinations thereof.
  • MRPs and/or sweeteners may be combined with one or more FMPs.
  • Particular MRP/FMP combinations include MRPs and maltol; MRPs and vanillin; sweetener (s) and maltol; sweetener (s) and vanillin etc.
  • Such compositions may be used in any of the food or beverage products described herein.
  • Production of MRPs or S-MRPs may comprise the use of any of the following methodologies, including reflux at atmospheric pressure, reaction under pressure, oven drying, vacuum oven drying, roller/drum drying, surface scraped heat exchange, and/or extrusion.
  • the MRP compositions and methods described herein are useful for improved taste and aroma profiles relative to control samples and for other natural sweeteners and mixtures therefrom, including but not limited to licorice, thaumatin etc., and mixtures with steviol glycosides, mogrosides, rubusosides etc.
  • the phrase “taste profile” which is interchangeable with “sensory profile” and “sweetness profile” , may be defined as the temporal profile of all basic tastes of a sweetener.
  • the “temporal profile” may be considered to represent the intensity of sweetness perceived over time in tasting of the composition by a human, especially a trained “taster” .
  • Carbohydrate and polyol sweeteners typically exhibit a quick onset followed by a rapid decrease in sweetness, which disappers realtively quickly on swallowing a food or beverage containing the same.
  • high intensity natural sweeteners typically have a slower sweet taste onset reaching a maximal response more slowly, followed by a decline in intensity more slowly than with carbohydrate and polyol sweeteners. This decline in sweetness is often referred to as “sweetness linger” and is a major limitation associated with the use of high intensity natural sweeteners.
  • the terms “improve” , “improved” and “improvement” are used interchangeably with reference to a perceived advantageous change in a composition or consumable product upon introduction of an MRP composition of the present application from the original taste profile of the composition or consumable product without the added MRP composition in any aspect, such as less bitterness, better sweetness, better sour taste, better aroma, better mouth feel, better flavor, less aftertaste, etc.
  • the terms “improve” or “improvement” can refer to a slight change, a change, or a significant change of the original taste profile, etc., which makes the composition more palatable to an individual.
  • the MRP compositions and methods described herein are useful for improving the taste and aroma profiles for other synthetic sweeteners, including but not limited to sucralose, ACE-K, aspartame, sodium saccharin, and mixtures thereof.
  • the MRP compositions of the present application may be evaluated with reference to the degree of their sucrose equivalence. Accordingly, the MRP compositions of the present application may be diluted or modified with respect to its ingredients to conform with this sucrose equivalence.
  • the onset and decay of sweetness when an MRP composition is consumed can be perceived by trained human tasters and measured in seconds from first contact with a taster's tongue ( "onset” ) to a cutoff point (typically 180 seconds after onset) to provide a "temporal profile of sweetness” .
  • a plurality of such human tasters is called a “sensory panel. "
  • sensory panels can also judge the temporal profile of the other "basic tastes” : bitterness, saltiness, sourness, piquance (aka spiciness) , and umami (aka savoriness or meatiness) .
  • Aromas from aroma producing substances are volatile compounds which are perceived by the odor receptor sites of the smell organ, i.e., the olfactory tissue of the nasal cavity. They reach the receptors when drawn in through the nose (orthonasal detection) and via the throat after being released by chewing (retronasal detection) .
  • aroma substances like the concept of taste substances, is to be used loosely, since a compound might contribute to the typical odor or taste of one food, while in another food it may cause a faulty odor or taste, or both, resulting in an off-flavor.
  • sensory profile may include evaluation of aroma as well.
  • mouth feel involves the physical and chemical interaction of a consumable in the mouth. More specifically, as used herein, the term “mouth feel” refers to the fullness sensation experienced in the mouth, which relates to the body and texture of the consumable such as its viscosity. Mouth feel is one of the most important organoleptic properties and the major criteria that consumers use to judge the quality and freshness of foods. Subtle changes in a food and beverage product’s formulation can change mouth feel significantly. Simply taking out sugar and adding a high intensity sweetener can cause noticeable alterations in mouth feel, making a formerly good product unacceptable to consumers. Sugar not only sweetens, it also builds body and viscosity in food and beverage products, and leaves a slight coating on the tongue. For example, reducing salt levels in soup changes not only taste, but can alter mouth feel as well. Primarily it is the mouth feel that is always the compliant with non-sugar sweeteners.
  • Maillard reaction products commonly taken as volatile substances, can provide great mouth feel and increase consumers’ acceptance of using high intensity sweeteners in food and beverage products, preferably high intensity sweetener (s) involved during the Maillard reaction.
  • Maillard reaction products can be used individually or combined with other sweeteners, especially “sugar-free” natural or synthetic sweeteners used for foods and beverages, such as tea, milk, coffee, chocolate etc.
  • Maillard reaction products when using Maillard reaction products with high intensity sweeteners such as sucralose, the inventors surprisingly found that Maillard reaction products can act as flavor modifier products to improve the taste profile of high intensity natural sweeteners, such as steviol glycosides and/or high intensity synthetic sweeteners, such as sucralose, as reflected in overall-likeability, less lingering, less astringency, less bitterness, quick upfront sweetness, umami, sensation enjoyment, fullness etc. Therefore, MRPs can be excellent flavor enhancers when blended with e.g., steviol glycosides and/or sucralose.
  • sweetness detection threshold refers to the minimum concentration at which panelists consisting of 1-10 persons are able to detect sweetness in a composition, liquid or solid. This is further defined as provided in the Examples herein and are conducted by the methods described in Sensory Testing for Flavorings with Modifying Properties by Christie L. Harman, John B. Hallagan, and the FEMA Science, Committee Sensory Data Task Force, November 2013, Volume 67, No. 11 and Appendix A attached thereto, the teachings of which are incorporated herein by reference.
  • Theshold of sweetness refers to a concentration of a material below which sweetness cannot be detected, but can still impart a flavor to a consumable (including water) .
  • the sample meets the threshold.
  • concentrations of the substance below the sweetness level are considered a flavoring agent.
  • the flavoring agents described herein can be used in combination with Stevia blends, including steviol glycosides, to encapsulate and reduce or eliminate the unwanted off taste of the Stevia component (s) present in the composition.
  • Stevia blends including steviol glycosides
  • a first reaction takes place between a first sugar donor and a first amine donor under appropriate conditions followed by a second reaction with a second sugar donor and a second amine donor, and possible subsequent reactions to provide a complex flavorant composition that is a combination of various Maillard reaction products between, for example, the first sugar donor and first amine donor, along with the reaction between the first sugar donor and a second amine donor or a second sugar donor reacting with the first sugar donor, etc. under the Maillard reaction conditions described herein.
  • the processes described herein can be used to preserve flavors.
  • a sample may be tested by e.g., a panel of 4-10 people.
  • a trained taster may independently taste the sample (s) first. The taster may be asked to describe the taste profile and score 0-5 according to the increasing sugar like, bitterness, aftertaste and lingering taste profiles. The taster may be allowed to re-taste, and then make notes for the sensory attributes perceived.
  • another group of 3-10 tasters may similarly taste the sample (s) , record its taste attributes and discuss the samples openly to find a suitable description. Where more than 1 taster disagrees with the results, the tasting may be repeated. For example, a “5” for sugar like is the best score for having a taste that is sugar like and conversely a value of 0 or near zero is not sugar like. Similarly, a “5” for bitterness, aftertaste and lingering is not desired. A value of zero or near zero means that the bitterness, aftertaste and/or lingering is reduced or is removed.
  • Other taste attributes may include astringency and overall likeability.
  • the composition of the present application further comprises one or more additional additives.
  • additives include, but are not limited to, salts, flavoring agents, minerals, organic acids and inorganic acids, polyols, nucleotides, bitter compounds, astringent compounds, proteins or protein hydrolysates, surfactants, gums and waxes, antioxidants, polymers, fatty acids, vitamins, preservatives, hydration agents, dietary fiber, glucosamine, probiotics, prebiotics, weight management agents, osteoporosis management agents, phytoestrogens, and phytosterols, as further described below.
  • the Maillard reaction mixture and MRP products can further include a salt.
  • the salt can be added during the Maillard reaction or after the reaction is complete.
  • Suitable salts include, for example, sodium carbonate, sodium bicarbonate, sodium chloride, potassium chloride, magnesium chloride, sodium sulfate, magnesium sulfate, potassium sulfate or mixtures thereof. Salts may form during the Maillard reaction itself from reactants or degraded reactants and be present in the Maillard reaction product (s) .
  • the salt (s) present in the Maillard reaction mixture can be from about 0 percent by weight to about 50 percent by weight, more particularly from about 0 percent to about 15 percent by weight, even more particularly from about 0 percent to about 5 percent by weight, e.g., 0.1, 0.2, 0.5, 0.75, 1, 2, 3 or 4 percent by weight of the Maillard reaction mixture.
  • the Maillard reaction product (s) and reaction mixture can include a sweetener.
  • the sweetener can be added before, during the Maillard reaction or after the reaction is completed.
  • Suitable sweeteners include non-nutritive sweeteners, such as for example, sorbitol, xylitol, mannitol, sucralose, aspartame, acesulfame-K, neotame, erythritol, trehalose, raffinose, cellobiose, tagatose, DOLCIA PRIMA TM allulose, inulin, N-- [N- [3- (3-hydroxy-4-methoxyphenyl) propyl] -alpha-aspartyl] -L-phenylalanine 1-methyl ester, glycyrrhizin, sodium cyclamate, saccharin, or mixtures thereof.
  • composition of the present application can comprise one or more salts.
  • salt refers to salts that retain the desired chemical activity of the compositions of the present application and are safe for human or animal consumption in a generally acceptable range.
  • the one or more salts may be organic or inorganic salts.
  • Nonlimiting examples of salts include sodium carbonate, sodium bicarbonate, sodium chloride, potassium chloride, magnesium chloride, sodium sulfate, magnesium sulfate, and potassium sulfate, or any edible salt, for example calcium salts, metal alkali halides, metal alkali carbonates, metal alkali bicarbonates, metal alkali phosphates, metal alkali sulfates, biphosphates, pyrophospates, triphosphates, metaphosphates, and metabisulfates.
  • the one or more salts are salts formed with metal cations such as calcium, bismuth, barium, magnesium, aluminum, copper, cobalt, nickel, cadmium, sodium, potassium, and the like, or with a cation formed from ammonia, N, N-dibenzylethylenediamine, D-glucosamine, ethanolamine, diethanolamine, triethanolamine, N-methylglucamine tetraethylammonium, or ethylenediamine.
  • metal cations such as calcium, bismuth, barium, magnesium, aluminum, copper, cobalt, nickel, cadmium, sodium, potassium, and the like
  • metal cations such as calcium, bismuth, barium, magnesium, aluminum, copper, cobalt, nickel, cadmium, sodium, potassium, and the like
  • the one or more salts are formed with inorganic acids, such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like; or formed with organic acids, such as acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3- (4-hydroxybenzoyl) benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1, 2-ethane-disulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, 4-chlorobenzenesulfonic acid, 2-naphthalenesulfonic acid, 4-toluenesulfonic acid,
  • non-limiting inorganic salts may be selected from the group consisting of sodium chloride, sodium carbonate, sodium bicarbonate, sodium acetate, sodium sulfide, sodium sulfate, sodium phosphate, potassium chloride, potassium citrate, potassium carbonate, potassium bicarbonate, potassium acetate, europium chloride (EuCl 3 ) , gadolinium chloride (GdCl 3 ) , terbium chloride (TbCl 3 ) , magnesium sulfate, alum, magnesium chloride, mono-, di-, tri-basic sodium or potassium salts of phosphoric acid (e.g., inorganic phosphates) , salts of hydrochloric acid (e.g., inorganic chlorides) , sodium carbonate, sodium bisulfate, and sodium bicarbonate.
  • EuCl 3 europium chloride
  • GdCl 3 gadolinium chloride
  • TbCl 3 terbium chloride
  • Exemplary organic salts may be selected from the group consisting of choline chloride, alginic acid sodium salt (sodium alginate) , glucoheptonic acid sodium salt, gluconic acid sodium salt (sodium gluconate) , gluconic acid potassium salt (potassium gluconate) , guanidine HCl, glucosamine HCl, amiloride HCl, monosodium glutamate (MSG) , adenosine monophosphate salt, magnesium gluconate, potassium tartrate (monohydrate) , and sodium tartrate (dihydrate) .
  • the salt is a metal or metal alkali halide, a metal or metal alkali carbonate or bicarbonate, or a metal or metal alkali phosphate, bisphosphate, pyrophosphate, triphosphate, metaphosphate, or metabisulfate thereof.
  • the salt is an inorganic salt that comprises sodium, potassium, calcium, or magnesium.
  • the salt is a sodium salt or a potassium salt.
  • the salt forms can be added to the sweetener compositions in the same amounts as their acid or base forms.
  • Alternative salts include various chloride or sulfate salts, such as sodium chloride, potassium chloride, magnesium chloride, sodium sulfate, magnesium sulfate, and potassium sulfate, or any edible salt.
  • the one or more salts comprise one or more salts of steviol glycosides (SG salts) and/or salts of glycosylated steviol glycosides (GSG-salts) .
  • the one or more SG salts comprise a salt of RB and/or STB.
  • the one or more salts comprise one or more amino acid salts. In some embodiments, the one or more salts comprise one or more poly-amino acid salts.
  • the one or more salts comprise one or more sugar acid salts, including e.g., aldonic, uronic, aldaric, alginic, gluconic, glucuronic, glucaric, galactaric, galacturonic, and their salts (e.g., sodium, potassium, calcium, magnesium salts or other physiologically acceptable salts) , and combinations thereof.
  • sugar acid salts including e.g., aldonic, uronic, aldaric, alginic, gluconic, glucuronic, glucaric, galactaric, galacturonic, and their salts (e.g., sodium, potassium, calcium, magnesium salts or other physiologically acceptable salts) , and combinations thereof.
  • the one or more salts can make up anywhere from about 0.01 wt. %to about 30 wt. %of the composition of the present application, specifically about 0.01 wt. %, about 0.02 wt. %, about 0.03 wt. %, about 0.04 wt. %, about 0.05 wt. %, about 0.06 wt. %, about 0.07 wt. %, about 0.08 wt. %, about 0.09 wt. %, 0.1 wt. %, about 0.2 wt. %, about 0.3 wt. %, about 0.4 wt. %, about 0.5 wt. %, about 0.6 wt.
  • wt. % about 0.7 wt. %, about 0.8 wt. %, about 0.9 wt. %, about 1 wt. %, about 2 wt. %, about 3 wt. %, about 4 wt. %, about 5 wt. %, about 6 wt. %, about 7 wt. %, about 8 wt. %, about 9 wt. %, about 10 wt. %, about 11 wt. %, about 12 wt. %, about 13 wt. %, about 14 wt. %, about 15 wt. %, about 16 wt. %, about 17 wt. %, about 18 wt.
  • the salt content in a composition is calculated based on the weight of sodium chloride. More specifically, the salt content (based on weight of NaCl) may be determined by determining the total ash content of a sample according to the general method for determining total ash content as set forth in FAO JECFA MONOGRAPHS, vol. 4, 2007. The weight of sodium chloride is determined from the weight of sodium oxide multiplied by a factor of 1.89. For example, if the total ash content of 100g the composition of the present application is 1g, the composition of the present application has a salt content of 1.89 wt %.
  • Minerals comprise inorganic chemical elements required by living organisms. Minerals are comprised of a broad range of compositions (e.g., elements, simple salts, and complex silicates) and also vary broadly in crystalline structure. They may naturally occur in foods and beverages, may be added as a supplement, or may be consumed or administered separately from foods or beverages.
  • compositions e.g., elements, simple salts, and complex silicates
  • Minerals may be categorized as either bulk minerals, which are required in relatively large amounts, or trace minerals, which are required in relatively small amounts.
  • Bulk minerals generally are required in amounts greater than or equal to about 100 mg per day and trace minerals are those that are required in amounts less than about 100 mg per day.
  • the minerals are chosen from bulk minerals, trace minerals or combinations thereof.
  • bulk minerals include calcium, chlorine, magnesium, phosphorous, potassium, sodium, and sulfur.
  • trace minerals include chromium, cobalt, copper, fluorine, iron, manganese, molybdenum, selenium, zinc, and iodine. Although iodine generally is classified as a trace mineral, it is required in larger quantities than other trace minerals and often is categorized as a bulk mineral.
  • the mineral is a trace mineral, believed to be necessary for human nutrition, non-limiting examples of which include bismuth, boron, lithium, nickel, rubidium, silicon, strontium, tellurium, tin, titanium, tungsten, and vanadium.
  • the minerals embodied herein may be in any form known to those of ordinary skill in the art.
  • the minerals are in their ionic form, having either a positive or negative charge.
  • sulfur and phosphorous often are found naturally as sulfates, sulfides, and phosphates.
  • the minerals are present in their molecular form.
  • minerals are present in the composition of the present application in an amount effective to provide an amount of from about 25 ppm to about 25,000 ppm in the final product.
  • Suitable organic acid additives include any compound which comprises a -COOH moiety, such as, for example, C2-C30 carboxylic acids, substituted hydroxyl C2-C30 carboxylic acids, butyric acid (ethyl esters) , substituted butyric acid (ethyl esters) , benzoic acid, substituted benzoic acids (e.g., 2, 4-dihydroxybenzoic acid) , substituted cinnamic acids, hydroxyacids, substituted hydroxybenzoic acids, anisic acid substituted cyclohexyl carboxylic acids, tannic acid, aconitic acid, lactic acid, tartaric acid, citric acid, isocitric acid, gluconic acid, glucoheptonic acids, adipic acid, hydroxycitric acid, malic acid, fruitaric acid (a blend of malic, fumaric, and tartaric acids) , fumaric acid, maleic acid, succinic acid, chlorogenic acid
  • organic acid additives described optionally may be substituted with at least one group chosen from hydrogen, alkyl, alkenyl, alkynyl, halo, haloalkyl, carboxyl, acyl, acyloxy, amino, amido, carboxyl derivatives, alkylamino, dialkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, sulfo, thiol, imine, sulfonyl, sulfenyl, sulfinyl, sulfamyl, carboxalkoxy, carboxamido, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, anhydride, oximino, hydrazino, carbamyl, phosphor or phosphonato.
  • the organic acid additive is present in the composition of the present application in an amount effective to provide anhydride, oximin
  • Organic acids also include amino acids such as, aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, arabinose, trans-4-hydroxyproline, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid ( ⁇ -, ⁇ -, and/or ⁇ -isomers) , glutamine, hydroxyproline, taurine, norvaline and sarcosine.
  • amino acids such as, aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, arabinose, trans-4-hydroxyproline, isoleucine, asparagine, serine,
  • the amino acid may be in the D-or L-configuration and in the mono-, di-, or tri-form of the same or different amino acids. Additionally, the amino acids may be ⁇ -, ⁇ -, ⁇ -and/or ⁇ -isomers if appropriate. Combinations of the foregoing amino acids and their corresponding salts (e.g., sodium, potassium, calcium, magnesium salts or other alkali or alkaline earth metal salts thereof, or acid salts) also are suitable additives in some embodiments.
  • the amino acids may be natural or synthetic.
  • the amino acids also may be modified.
  • Modified amino acids refers to any amino acid wherein at least one atom has been added, removed, substituted, or combinations thereof (e.g., N-alkyl amino acid, N-acyl amino acid, or N-methyl amino acid) .
  • modified amino acids include amino acid derivatives such as trimethyl glycine, N-methyl-glycine, and N-methyl-alanine.
  • modified amino acids encompass both modified and unmodified amino acids.
  • amino acids also encompass both peptides and polypeptides (e.g., dipeptides, tripeptides, tetrapeptides, and pentapeptides) such as glutathione and L-alanyl-L-glutamine.
  • polypeptides e.g., dipeptides, tripeptides, tetrapeptides, and pentapeptides
  • glutathione and L-alanyl-L-glutamine such as glutathione and L-alanyl-L-glutamine.
  • Suitable polyamino acid additives include poly-L-aspartic acid, poly-L-lysine (e.g., poly-L-a-lysine or poly-L-s-lysine) , poly-L-ornithine (e.g., poly-L-a-ornithine or poly-L-s-ornithine) , poly-L-arginine, other polymeric forms of amino acids, and salt forms thereof (e.g., calcium, potassium, sodium, or magnesium salts such as L-glutamic acid mono sodium salt) .
  • the poly-amino acid additives also may be in the D-or L-configuration.
  • poly-amino acids may be ⁇ -, ⁇ -, ⁇ -, ⁇ -, and ⁇ -isomers if appropriate. Combinations of the foregoing poly-amino acids and their corresponding salts (e.g., sodium, potassium, calcium, magnesium salts or other alkali or alkaline earth metal salts thereof or acid salts) also are suitable additives in some embodiments.
  • the poly-amino acids described herein also may comprise co-polymers of different amino acids.
  • the poly-amino acids may be natural or synthetic.
  • poly-amino acids also may be modified, such that at least one atom has been added, removed, substituted, or combinations thereof (e.g., N-alkyl poly-amino acid or N-acyl poly-amino acid) .
  • poly-amino acids encompass both modified and unmodified poly-amino acids.
  • modified poly-amino acids include, but are not limited to, poly-amino acids of various molecular weights (MW) , such as poly-L-a-lysine with a MW of 1,500, MW of 6,000, MW of 25,200, MW of 63,000, MW of 83,000, or MW of 300,000.
  • the amino acid is present in the composition of the present application in an amount effective to provide an amount of from about 10 ppm to about 50,000 ppm in the final product.
  • Suitable inorganic acid additives include, but are not limited to, phosphoric acid, phosphorous acid, polyphosphoric acid, hydrochloric acid, sulfuric acid, carbonic acid, sodium dihydrogen phosphate, and alkali or alkaline earth metal salts thereof (e.g., inositol hexaphosphate Mg/Ca) .
  • the in organic acid is present in the composition of the present application in an amount effective to provide an amount of from about 25 ppm to about 25,000 ppm in the final product.
  • polyol refers to a molecule that contains more than one hydroxyl group.
  • a polyol may be a diol, triol, or a tetraol which contains 2, 3, and 4 hydroxyl groups respectively.
  • a polyol also may comprise more than 4 hydroxyl groups, such as a pentaol, hexaol, heptaol, or the like, which comprise 5, 6, or 7 hydroxyl groups, respectively.
  • a polyol also may be a sugar alcohol, polyhydric alcohol, or polyalcohol which is a reduced form of carbohydrate, wherein the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
  • Non-limiting examples of polyols in some embodiments include maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerin) , threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup, and sugar alcohols or any other carbohydrates capable of being reduced which do not adversely affect taste.
  • polyol is present in the compositions of the present application in an amount effective to provide an amount of from about 100 ppm to about 250,000 ppm in the final product.
  • Suitable nucleotide additives include, but are not limited to, inosine monophosphate ( “IMP” ) , guanosine monophosphate ( “GMP” ) , adenosine monophosphate ( “AMP” ) , cytosine monophosphate (CMP) , uracil monophosphate (UMP) , inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil diphosphate, inosine triphosphate, guanosine triphosphate, adenosine triphosphate, cytosine triphosphate, uracil triphosphate, alkali or alkaline earth metal salts thereof, or combinations thereof.
  • inosine monophosphate “IMP” )
  • GMP guanosine monophosphate
  • AMP adenosine monophosphate
  • CMP cytosine monophosphate
  • UMP uracil monophosphat
  • nucleotides described herein also may comprise nucleotide-related additives, such as nucleosides or nucleic acid bases (e.g., guanine, cytosine, adenine, thymine, uracil) .
  • nucleosides or nucleic acid bases e.g., guanine, cytosine, adenine, thymine, uracil
  • nucleotide is present in the compositions of the present application in an amount effective to provide an amount of from about 5 ppm to about 1,000 ppm in the final product.
  • Suitable bitter compound additives include, but are not limited to, caffeine, quinine, urea, bitter orange oil, naringin, quassia, and salts thereof.
  • bitter compounds are present in the compositions of the present application in an amount effective to provide an amount of from about 25 ppm to about 25,000 ppm in the final product.
  • Suitable astringent compound additives include, but are not limited to, tannic acid, europium chloride (EuCl3) , gadolinium chloride (GdCl3) , terbium chloride (TbCl3) , alum, tannic acid, and polyphenols (e.g., tea polyphenols) .
  • astringent compound is present in the compositions of the present application in an amount effective to provide an amount of from about 0.5 ppm to about 5,000 ppm in the final product.
  • Suitable protein or protein hydrolysate additives include, but are not limited to, bovine serum albumin (BSA) , whey protein (including fractions or concentrates thereof such as 90%instant whey protein isolate, 34%whey protein, 50%> hydrolyzed whey protein, and 80%> whey protein concentrate) , soluble rice protein, soy protein, protein isolates, protein hydrolysates, reaction products of protein hydrolysates, glycoproteins, and/or proteoglycans containing amino acids (e.g., glycine, alanine, serine, threonine, asparagine, glutamine, arginine, valine, isoleucine, leucine, norvaline, methionine, proline, tyrosine, hydroxyproline, and the like) , collagen (e.g., gelatin) , partially hydrolyzed collagen (e.g., hydrolyzed fish collagen) , and collagen hydrolysates (e.g., porcine collagen
  • proteins or protein hydrolysates are present in the compositions of the present application in an amount effective to provide an amount of from about 100 ppm to about 50,000 ppm in the final product.
  • Suitable surfactant additives include, but are not limited to, polysorbates (e.g., polyoxyethylene sorbitan monooleate (polysorbate 80) , polysorbate 20, polysorbate 60) , sodium dodecylbenzenesulfonate, dioctyl sulfosuccinate or dioctyl sulfosuccinate sodium, sodium dodecyl sulfate, cetylpyridinium chloride (hexadecylpyridinium chloride) , hexadecyltnmethylammonium bromide, sodium cholate, carbamoyl, choline chloride, sodium glycocholate, sodium taurodeoxycholate, lauric arginate, sodium stearoyl lactylate, sodium taurocholate, lecithins, sucrose oleate esters, sucrose stearate esters, sucrose palmitate esters, sucrose laurate esters, and other e
  • surfactants are present in the compositions of the present application in an amount effective to provide an amount of from about 20 ppm to about 20,000 ppm in the final product.
  • Gums and mucilages represent a broad array of different branched structures.
  • Guar gum is a galactomannan produced from the ground endosperm of the guar seed. Guar gum is commercially available (e.g., Benefiber by Novartis AG) .
  • Other gums such as gum arabic and pectins, have still different structures. Still other gums include xanthan gum, gellan gum, tara gum, psylium seed husk gum, and locust been gum.
  • Waxes are esters of ethylene glycol and two fatty acids, generally occurring as a hydrophobic liquid that is insoluble in water.
  • gums or waxes are present in the compositions of the present application in an amount effective to provide an amount of from about 100 ppm to about 100,000 ppm in the final product.
  • antioxidant refers to any substance which inhibits, suppresses, or reduces oxidative damage to cells and biomolecules. Without being bound by theory, it is believed that antioxidants inhibit, suppress, or reduce oxidative damage to cells or biomolecules by stabilizing free radicals before they can cause harmful reactions. As such, antioxidants may prevent or postpone the onset of some degenerative diseases.
  • antioxidants examples include, but are not limited to, vitamins, vitamin cofactors, minerals, hormones, carotenoids, carotenoid terpenoids, non-carotenoid terpenoids, flavonoids, flavonoid polyphenolics (e.g., bioflavonoids) , flavonols, flavones, phenols, polyphenols, esters of phenols, esters of polyphenols, nonflavonoid phenolics, isothiocyanates, or combinations thereof.
  • bioflavonoids e.g., bioflavonoids
  • the antioxidant is vitamin A, vitamin C, vitamin E, ubiquinone, mineral selenium, manganese, melatonin, a-carotene, ⁇ -carotene, lycopene, lutein, zeanthin, crypoxanthin, reservatol, eugenol, quercetin, catechin, gossypol, hesperetin, curcumin, ferulic acid, thymol, hydroxytyrosol, tumeric, thyme, olive oil, lipoic acid, glutathinone, gutamine, oxalic acid, tocopherol-derived compounds, butylated hydroxyanisole (BHA) , butylated hydroxytoluene (BHT) , ethylenediaminetetraacetic acid (EDTA) , tert-butylhydroquinone, acetic acid, pectin, tocotrienol, tocophe
  • BHA
  • the antioxidant is a synthetic antioxidant such as butylated hydroxytolune or butylated hydroxyanisole, for example.
  • suitable antioxidants for embodiments of this application include, but are not limited to, fruits, vegetables, tea, cocoa, chocolate, spices, herbs, rice, organ meats from livestock, yeast, whole grains, or cereal grains.
  • antioxidants for use in flavoring agents: ascorbic acid and salts thereof, ascorbyl palmitate, butylated hydroxyanisole (BHA) , butylated hydroxytoluene (BHT) , dodecyl gallate, erythorbic acid and salts thereof, octyl gallate, propyl gallate, tert. -butyl hydroquinone (TBHQ) , natural tocopherols, and synthetic tocopherols.
  • BHA butylated hydroxyanisole
  • BHT butylated hydroxytoluene
  • TBHQ tert. -butyl hydroquinone
  • polyphenols also known as “polyphenolics”
  • polyphenolics are a group of chemical substances found in plants, characterized by the presence of more than one phenol group per molecule.
  • a variety of health benefits may be derived from polyphenols, including prevention of cancer, heart disease, and chronic inflammatory disease and improved mental strength and physical strength, for example.
  • Suitable polyphenols for embodiments of this application include catechins, proanthocyanidins, procyanidins, anthocyanins, quercerin, rutin, reservatrol, isoflavones, curcumin, punicalagin, ellagitannin, hesperidin, naringin, citrus flavonoids, chlorogenic acid, other similar materials, or combinations thereof.
  • Neohesperidin and naringin are flavanone glycosides present in citrus fruits and grapefruit, and are responsible for the bitterness of citrus juices.
  • Neohesperidin, naringin, and their derivatives, such as neohesperidine chalcone, naringin chalcone, phloracetophenone, neohesperidine dihydrochalcone, naringin dihydrochalcone etc. (as further described herein) are good candidates for bitter or sweet enhancers. It has been surprisingly found that adding these components to the MRP compositions of the present invention can help to mask the bitterness and/or aftertaste of other ingredients and make the taste cleaner.
  • the antioxidant is a citrus flavonoid or flavanone glycoside, such as hesperidin or naringin.
  • Suitable natural sources of citrus flavonoids, such as hesperidin or naringin, for embodiments of this application include, but are not limited to, oranges, grapefruits, and citrus juices.
  • the ratio of flavonoids in the MRP compositions can range from 0.1 ppm to 99.9% (w/w) .
  • the antioxidant is a catechin such as, for example, epigallocatechin gallate (EGCG) .
  • EGCG epigallocatechin gallate
  • Suitable sources of catechins for embodiments of this application include, but are not limited to, green tea, white tea, black tea, oolong tea, chocolate, cocoa, red wine, grape seed, red grape skin, purple grape skin, red grape juice, purple grape juice, berries, pycnogenol, and red apple peel.
  • the antioxidant is chosen from proanthocyanidins, procyanidins or combinations thereof.
  • Suitable sources of proanthocyanidins and procyanidins for embodiments of this application include, but are not limited to, red grapes, purple grapes, cocoa, chocolate, grape seeds, red wine, cacao beans, cranberry, apple peel, plum, blueberry, black currants, choke berry, green tea, sorghum, cinnamon, barley, red kidney bean, pinto bean, hops, almonds, hazelnuts, pecans, pistachio, pycnogenol, and colorful berries.
  • the antioxidant is an anthocyanin.
  • Suitable sources of anthocyanins for embodiments of this application include, but are not limited to, red berries, blueberries, bilberry, cranberry, raspberry, cherry, pomegranate, strawberry, elderberry, choke berry, red grape skin, purple grape skin, grape seed, red wine, black currant, red currant, cocoa, plum, apple peel, peach, red pear, red cabbage, red onion, red orange, and blackberries.
  • the antioxidant is chosen from quercetin, rutin or combinations thereof.
  • Suitable sources of quercetin and rutin for embodiments of this application include, but are not limited to, red apples, onions, kale, bog whortleberry, lingonberrys, chokeberry, cranberry, blackberry, blueberry, strawberry, raspberry, black currant, green tea, black tea, plum, apricot, parsley, leek, broccoli, chili pepper, berry wine, and ginkgo.
  • the antioxidant is reservatrol.
  • Suitable sources of reservatrol for embodiments of this application include, but are not limited to, red grapes, peanuts, cranberry, blueberry, bilberry, mulberry, Japanese Itadori tea, and red wine.
  • the antioxidant is an isoflavone.
  • Suitable sources of isoflavones for embodiments of this application include, but are not limited to, soy beans, soy products, legumes, alfalfa sprouts, chickpeas, peanuts, and red clover.
  • the antioxidant is curcumin.
  • Suitable sources of curcumin for embodiments of this application include, but are not limited to, turmeric and mustard.
  • the antioxidant is chosen from punicalagin, ellagitannin or combinations thereof.
  • Suitable sources of punicalagin and ellagitannin for embodiments of this application include, but are not limited to, pomegranate, raspberry, strawberry, walnut, and oak-aged red wine.
  • the antioxidant is chlorogenic acid.
  • Suitable sources of chlorogenic acid for embodiments of this application include, but are not limited to, green coffee, yerba mate, red wine, grape seed, red grape skin, purple grape skin, red grape juice, purple grape juice, apple juice, cranberry, pomegranate, blueberry, strawberry, sunflower, Echinacea, pycnogenol, and apple peel.
  • antioxidants are present in the compositions of the present application in an amount effective to provide an amount of from about 100 ppm to about 250,000 ppm in the final product.
  • Suitable polymer additives include, but are not limited to, chitosan, pectin, pectic, pectinic, polyuronic, polygalacturonic acid, starch, food hydrocolloid or crude extracts thereof (e.g., gum acacia Senegal (Fibergum TM ) , gum acacia seyal, carageenan) , poly-L-lysine (e.g., poly-L- ⁇ -lysine or poly-L- ⁇ -lysine) , poly-L-ornithine (e.g., poly-L- ⁇ -ornithine or poly-L- ⁇ -ornithine) , polypropylene glycol, polyethylene glycol, poly (ethylene glycol methyl ether) , polyarginine, polyaspartic acid, polyglutamic acid, polyethylene imine, alginic acid, sodium alginate, propylene glycol alginate, and sodium polyethyleneglycolalginate, sodium
  • a polymer is present in the compositions of the present application in an amount effective to provide an amount of from about 10 ppm to about 10,000 ppm in the final product.
  • a “fatty acid” refers to any straight chain monocarboxylic acid and includes saturated fatty acids, unsaturated fatty acids, long chain fatty acids, medium chain fatty acids, short chain fatty acids, fatty acid precursors (including omega-9 fatty acid precursors) , and esterified fatty acids.
  • a “long chain polyunsaturated fatty acid” refers to any polyunsaturated carboxylic acid or organic acid with a long aliphatic tail.
  • omega-3 fatty acid refers to any polyunsaturated fatty acid having a first double bond as the third carbon-carbon bond from the terminal methyl end of its carbon chain.
  • the omega-3 fatty acid may comprise a long chain omega-3 fatty acid.
  • an “omega-6 fatty acid” refers to any polyunsaturated fatty acid having a first double bond as the sixth carbon-carbon bond from the terminal methyl end of its carbon chain.
  • Suitable omega-3 fatty acids for use in embodiments of the present application can be produced from algae, fish, animals, plants, or combinations thereof, for example.
  • suitable omega-3 fatty acids include, but are not limited to, linolenic acid, alpha-linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, stearidonic acid, eicosatetraenoic acid or combinations thereof.
  • suitable omega-3 fatty acids can be provided in fish oils, (e.g., menhaden oil, tuna oil, salmon oil, bonito oil, and cod oil) , microalgae omega-3 oils or combinations thereof.
  • suitable omega-3 fatty acids may be produced from commercially available omega-3 fatty acid oils, such as Microalgae DHA oil (from Martek, Columbia, MD) , OmegaPure (from Omega Protein, Houston, TX) , Marinol C-38 (from Lipid Nutrition, Channahon, IL) , Bonito oil and MEG-3 (from Ocean Nutrition, Dartmouth, NS) , Evogel (from Symrise, Holzminden, Germany) , Marine Oil, from tuna or salmon (from Arista Wilton, CT) , OmegaSource 2000, Marine Oil, from menhaden and Marine Oil, from cod (from OmegaSource, RTP, NC) .
  • omega-3 fatty acid oils such as Microalgae DHA oil (from Martek, Columbia, MD) , OmegaPure (from Omega Protein, Houston, TX) , Marinol C-38 (from Lipid Nutrition, Channahon, IL) , Bonito oil and MEG-3 (from Ocean Nutrition, Dartmouth, NS) , Evo
  • Suitable omega-6 fatty acids include, but are not limited to, linoleic acid, gamma-linolenic acid, dihommo-gamma-linolenic acid, arachidonic acid, eicosadienoic acid, docosadienoic acid, adrenic acid, docosapentaenoic acid, or combinations thereof.
  • Suitable esterified fatty acids for embodiments of the present application may include, but are not limited to, monoacylgycerols containing omega-3 and/or omega-6 fatty acids, diacylgycerols containing omega-3 and/or omega-6 fatty acids, triacylgycerols containing omega-3 and/or omega-6 fatty acids, or combinations thereof.
  • fatty acids are present in the compositions of the present application in an amount from about 100 ppm to about 100,000 ppm.
  • Vitamins are organic compounds that the human body needs in small quantities for normal functioning. The body uses vitamins without breaking them down, unlike other nutrients such as carbohydrates and proteins. To date, thirteen vitamins have been recognized, and one or more can be used in the compositions herein. Suitable vitamins and their alternative chemical names are provided in the accompanying parentheses which follow include, vitamin A (retinol, retinaldehyde) , vitamin D (calciferol, cholecalciferol, lumisterol, ergocalciferol, dihydrotachysterol, 7-dehydrocholesterol) , vitamin E (tocopherol, tocotrienol) , vitamin K (phylloquinone, naphthoquinone) , vitamin B1 (thiamin) , vitamin B2 (riboflavin, vitamin G) , vitamin B3 (niacin, nicotinic acid, vitamin PP) , vitamin B5 (pantothenic acid) , vitamin B6 (pyridoxine, pyridoxal,
  • vitamin includes pseudo-vitamins.
  • the vitamin is a fat-soluble vitamin chosen from vitamin A, D, E, K or combinations thereof. In other embodiments, the vitamin is a water-soluble vitamin chosen from vitamin B1, vitamin B2, vitamin B3, vitamin B6, vitamin B12, folic acid, biotin, pantothenic acid, vitamin C or combinations thereof.
  • vitamins are present in the compositions of the present application in an amount effective to provide an amount of from about 10 ppm to about 10,000 ppm in the final product.
  • the preservative is chosen from antimicrobials, antienzymatics or combinations thereof.
  • Non-limiting examples of antimicrobials include sulfites, propionates, benzoates, sorbates, nitrates, nitrites, bacteriocins such as nisin, salts, sugars, acetic acid, dimethyl dicarbonate (DMDC) , ethanol, and ozone.
  • Sulfites include, but are not limited to, sulfur dioxide, sodium bisulfite, and potassium hydrogen sulfite.
  • Propionates include, but are not limited to, propionic acid, calcium propionate, and sodium propionate.
  • Benzoates include, but are not limited to, sodium benzoate and benzoic acid.
  • Sorbates include, but are not limited to, potassium sorbate, sodium sorbate, calcium sorbate, and sorbic acid.
  • Nitrates and nitrites include, but are not limited to, sodium nitrate and sodium nitrite.
  • Non-limiting examples of antienzymatics suitable for use as preservatives in particular embodiments of the application include ascorbic acid, citric acid, and metal chelating agents such as ethylenediaminetetraacetic acid (EDTA) .
  • preservatives are present in the compositions of the present application in an amount from about 100 ppm to about 5000 ppm.
  • Hydration agents help the body to replace fluids that are lost through excretion.
  • fluid is lost as sweat in order to regulate body temperature, as urine in order to excrete waste substances, and as water vapor in order to exchange gases in the lungs.
  • Fluid loss can also occur due to a wide range of external causes, non-limiting examples of which include physical activity, exposure to dry air, diarrhea, vomiting, hyperthermia, shock, blood loss, and hypotension.
  • Diseases causing fluid loss include diabetes, cholera, gastroenteritis, shigellosis, and yellow fever.
  • Forms of malnutrition causing fluid loss include excessive consumption of alcohol, electrolyte imbalance, fasting, and rapid weight loss.
  • the hydration agent helps the body replace fluids that are lost during exercise.
  • the hydration agent is an electrolyte, non-limiting examples of which include sodium, potassium, calcium, magnesium, chloride, phosphate, bicarbonate, or combinations thereof.
  • Suitable electrolytes for use in some embodiments of this application are also described in U.S. Patent No. 5,681,569, the disclosure of which is expressly incorporated herein by reference.
  • the electrolytes are obtained from their corresponding water-soluble salts.
  • Non-limiting examples of salts for use in some embodiments include chlorides, carbonates, sulfates, acetates, bicarbonates, citrates, phosphates, hydrogen phosphates, tartrates, sorbates, citrates, benzoates, or combinations thereof.
  • the electrolytes are provided by juice, fruit extracts, vegetable extracts, tea, or tea extracts.
  • the hydration agent is a flavanol that provides cellular rehydration.
  • Flavanols are a class of natural substances present in plants, and generally comprise a 2-phenylbenzopyrone molecular skeleton attached to one or more chemical moieties.
  • Non-limiting examples of flavanols suitable for use herein include catechin, epicatechin, gallocatechin, epigallocatechin, epicatechin gallate, epigallocatechin 3-gallate, theaflavin, theaflavin 3 -gallate, theaflavin 3'-gallate, theaflavin 3, 3' gallate, thearubigin or combinations thereof.
  • Several common sources of flavanols include tea plants, fruits, vegetables, and flowers. In preferred embodiments, the flavanol is extracted from green tea.
  • the hydration agent is a glycerol solution to enhance exercise endurance.
  • the ingestion of a glycerol containing solution has been shown to provide beneficial physiological effects, such as expanded blood volume, lower heart rate, and lower rectal temperature.
  • hydration agents are present in the compositions of the present application in an amount effective to provide an amount of from about 100 ppm to about 250,000 ppm in the final product.
  • composition of the present application further comprises one or more functional ingredients.
  • additional additives include, but are not limited to, dietary fiber sources, glucosamine, probiotics, prebiotics, weight management agents, osteoporosis management agents, phytoestrogens, phytosterols and combinations thereof.
  • the functional ingredient is at least one dietary fiber source.
  • the at least one dietary fiber source can comprise a single dietary fiber source or a plurality of dietary fiber sources as a functional ingredient for the compositions provided herein.
  • the at least one dietary fiber source is present in the composition in an amount sufficient to promote health and wellness.
  • polymeric carbohydrates having significantly different structures in both composition and linkages fall within the definition of dietary fiber.
  • Such compounds are well known to those skilled in the art, non-limiting examples of which include non-starch polysaccharides, lignin, cellulose, methylcellulose, the hemicelluloses, ⁇ -glucans, pectins, gums, mucilage, waxes, inulins, oligosaccharides, fructooligosaccharides, cyclodextrins, chitins, and combinations thereof.
  • Polysaccharides are complex carbohydrates composed of monosaccharides joined by glycosidic linkages.
  • Non-starch polysaccharides are bonded with ⁇ -linkages, which humans are unable to digest due to a lack of an enzyme to break the ⁇ -linkages.
  • digestible starch polysaccharides generally comprise ⁇ (1-4) linkages.
  • Lignin is a large, highly branched and cross-linked polymer based on oxygenated phenylpropane units.
  • Cellulose is a linear polymer of glucose molecules joined by a ⁇ (1-4) linkage, which mammalian amylases are unable to hydrolyze.
  • Methylcellulose is a methyl ester of cellulose that is often used in foodstuffs as a thickener, and emulsifier. It is commercially available (e.g., Citrucel by GlaxoSmithKline, Celevac by Shire Pharmaceuticals) .
  • Hemicelluloses are highly branched polymers consisting mainly of glucurono-and 4-O-methylglucuroxylans.
  • ⁇ -glucans are mixed-linkage (1-3) , (1-4) ⁇ -D-glucose polymers found primarily in cereals, such as oats and barley.
  • Pectins such as beta pectin, are a group of polysaccharides composed primarily of D-galacturonic acid, which is methoxylated to variable degrees.
  • Gums and mucilages represent a broad array of different branched structures.
  • Guar gum derived from the ground endosperm of the guar seed, is a galactomannan. Guar gum is commercially available (e.g., Benefiber by Novartis AG) . Other gums, such as gum arabic and pectins, have still different structures. Still other gums include xanthan gum, gellan gum, tara gum, psylium seed husk gum, and locust been gum.
  • Waxes are esters of ethylene glycol and two fatty acids, generally occurring as a hydrophobic liquid that is insoluble in water.
  • Inulins comprise naturally occurring oligosaccharides belonging to a class of carbohydrates known as fructans. They generally are comprised of fructose units joined by ⁇ (2- 1) glycosidic linkages with a terminal glucose unit. Oligosaccharides are saccharide polymers containing typically three to six component sugars. They are generally found either 0-or N-linked to compatible amino acid side chains in proteins or to lipid molecules. Fructooligosaccharides are oligosaccharides consisting of short chains of fructose molecules.
  • Food sources of dietary fiber include, but are not limited to, grains, legumes, fruits, and vegetables.
  • Grains providing dietary fiber include, but are not limited to, oats, rye, barley, wheat.
  • Legumes providing fiber include, but are not limited to, peas and beans such as soybeans.
  • Fruits and vegetables providing a source of fiber include, but are not limited to, apples, oranges, pears, bananas, berries, tomatoes, green beans, broccoli, cauliflower, carrots, potatoes, celery.
  • Plant foods such as bran, nuts, and seeds (such as flax seeds) are also sources of dietary fiber.
  • Parts of plants providing dietary fiber include, but are not limited to, the stems, roots, leaves, seeds, pulp, and skin.
  • dietary fiber generally is derived from plant sources
  • indigestible animal products such as chitins are also classified as dietary fiber.
  • Chitin is a polysaccharide composed of units of acetylglucosamine joined by ⁇ (1-4) linkages, similar to the linkages of cellulose.
  • Sources of dietary fiber often are divided into categories of soluble and insoluble fiber based on their solubility in water. Both soluble and insoluble fibers are found in plant foods to varying degrees depending upon the characteristics of the plant. Although insoluble in water, insoluble fiber has passive hydrophilic properties that help increase bulk, soften stools, and shorten transit time of fecal solids through the intestinal tract.
  • soluble fiber Unlike insoluble fiber, soluble fiber readily dissolves in water. Soluble fiber undergoes active metabolic processing via fermentation in the colon, increasing the colonic microflora and thereby increasing the mass of fecal solids. Fennentation of fibers by colonic bacteria also yields end-products with significant health benefits. For example, fermentation of the food masses produces gases and short-chain fatty acids. Acids produced during fermentation include butyric, acetic, propionic, and valeric acids that have various beneficial properties such as stabilizing blood glucose levels by acting on pancreatic insulin release and providing liver control by glycogen breakdown. In addition, fiber fermentation may reduce atherosclerosis by lowering cholesterol synthesis by the liver and reducing blood levels of LDL and triglycerides.
  • the acids produced during fermentation lower colonic pH, thereby protecting the colon lining from cancer polyp formation.
  • the lower colonic pH also increases mineral absorption, improves the barrier properties of the colonic mucosal layer, and inhibits inflammatory and adhesion irritants. Fermentation of fibers also may benefit the immune system by stimulating production of T-helper cells, antibodies, leukocytes, splenocytes, cytokinins and lymphocytes.
  • the functional ingredient is glucosamine.
  • glucosamine is present in the compositions in an amount sufficient to promote health and wellness.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Mycology (AREA)
  • Seasonings (AREA)

Abstract

L'invention concerne des compositions d'édulcorant et d'arôme présentant des profils de goût améliorés. L'invention concerne également des procédés de fabrication et des procédés d'utilisation de ces compositions d'édulcorant et d'arôme.
PCT/CN2019/085635 2018-05-08 2019-05-06 Compositions d'édulcorant et d'arôme, leurs procédés de fabrication et leurs procédés d'utilisation WO2019214567A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2020563513A JP7474201B2 (ja) 2018-05-08 2019-05-06 甘味料および香料組成物、製造方法およびそれらの使用方法
CN201980030742.XA CN112218542B (zh) 2018-05-08 2019-05-06 甜味剂和风味剂组合物，其制备方法和使用方法
AU2019264701A AU2019264701A1 (en) 2018-05-08 2019-05-06 Sweetener and flavor compositions, methods of making and methods of use thereof

Applications Claiming Priority (52)

Application Number Priority Date Filing Date Title
US201862668535P 2018-05-08 2018-05-08
US201862668580P 2018-05-08 2018-05-08
US201862668553P 2018-05-08 2018-05-08
US62/668,553 2018-05-08
US62/668,580 2018-05-08
US62/668,535 2018-05-08
US201862691723P 2018-06-29 2018-06-29
US62/691,723 2018-06-29
US201862696481P 2018-07-11 2018-07-11
US62/696,481 2018-07-11
US201862730449P 2018-09-12 2018-09-12
US62/730,449 2018-09-12
US201862744755P 2018-10-12 2018-10-12
US62/744,755 2018-10-12
US201862771485P 2018-11-26 2018-11-26
US62/771,485 2018-11-26
US201862775983P 2018-12-06 2018-12-06
US62/775,983 2018-12-06
US201962819980P 2019-03-18 2019-03-18
US62/819,980 2019-03-18
US201962841858P 2019-05-02 2019-05-02
US62/841,858 2019-05-02
US16/402,641 2019-05-03
US16/402,728 US11154079B2 (en) 2018-05-08 2019-05-03 Tasteful natural sweetener and flavor
US16/402,991 US11266170B2 (en) 2018-05-08 2019-05-03 Sweetener and flavor compositions, methods of making and methods of use thereof
US16/402,999 2019-05-03
US16/402,728 2019-05-03
US16/403,053 US11304431B2 (en) 2018-05-08 2019-05-03 Sweetener and flavor compositions, methods of making and methods of use thereof
US16/402,413 US11324237B2 (en) 2018-05-08 2019-05-03 Tasteful natural sweetener and flavor
US16/402,816 US11369127B2 (en) 2018-05-08 2019-05-03 Sweetener and flavor compositions, methods of making and methods of use thereof
US16/402,448 2019-05-03
US16/403,163 2019-05-03
US16/402,360 US11425923B1 (en) 2018-05-08 2019-05-03 Tasteful natural sweetener and flavor
US16/402,846 2019-05-03
US16/402,448 US11849742B2 (en) 2018-05-08 2019-05-03 Tasteful natural sweetener and flavor
US16/402,846 US11147295B2 (en) 2018-05-08 2019-05-03 Sweetener and flavor compositions, methods of making and methods of use thereof
US16/402,360 2019-05-03
US16/403,178 US20200367543A1 (en) 2018-05-08 2019-05-03 Sweetener and flavor compositions, methods of making and methods of use thereof
US16/402,816 2019-05-03
US16/402,413 2019-05-03
US16/402,999 US11284634B2 (en) 2018-05-08 2019-05-03 Sweetener and flavor compositions, methods of making and methods of use thereof
US16/403,061 US11793218B2 (en) 2018-05-08 2019-05-03 Sweetener and flavor compositions, methods of making and methods of use thereof
US16/402,991 2019-05-03
US16/403,163 US20190357579A1 (en) 2018-05-08 2019-05-03 Sweetener and flavor compositions, methods of making and methods of use thereof
US16/402,641 US11102996B2 (en) 2018-05-08 2019-05-03 Sweetener and flavor compositions, methods of making and methods of use thereof
US16/403,223 US20210045420A1 (en) 2018-05-08 2019-05-03 Sweetener and flavor compositions, methods of making and methods of use thereof
US16/403,223 2019-05-03
US16/403,178 2019-05-03
US16/403,053 2019-05-03
US16/403,061 2019-05-03
US16/402,605 2019-05-03
US16/402,605 US11252978B2 (en) 2018-05-08 2019-05-03 Tasteful natural sweetener and flavor

Publications (1)

Publication Number Publication Date
WO2019214567A1 true WO2019214567A1 (fr) 2019-11-14

Family

ID=68466853

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2019/085635 WO2019214567A1 (fr) 2018-05-08 2019-05-06 Compositions d'édulcorant et d'arôme, leurs procédés de fabrication et leurs procédés d'utilisation

Country Status (1)

Country Link
WO (1) WO2019214567A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112493481A (zh) * 2020-11-30 2021-03-16 李军 一种运动营养补充含片及其制备方法
CN112931632A (zh) * 2021-03-12 2021-06-11 石家庄君乐宝乳业有限公司 炭烧干酪制品及其制备方法
CN113397117A (zh) * 2021-06-30 2021-09-17 四川好哥们食品有限公司 一种方便即食型冷吃食品的制备方法
WO2021233242A1 (fr) * 2020-05-19 2021-11-25 Epc Natural Products Co., Ltd. Compositions édulcorantes et aromatisantes contenant des glycosides terpéniques
WO2021232750A1 (fr) * 2020-05-19 2021-11-25 Epc Natural Products Co., Ltd. Compositions d'édulcorant et d'arôme
CN113749257A (zh) * 2020-06-01 2021-12-07 鲁南制药集团股份有限公司 一种益生菌组合物及其在调味面制品中的应用
WO2023242015A3 (fr) * 2022-06-14 2024-02-29 Givaudan Sa Compositions contenant de la brazzéine

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101652342A (zh) * 2007-03-30 2010-02-17 吉万奥丹股份有限公司 遮蔽不适感感觉的有机化合物
CN102076223A (zh) * 2008-06-24 2011-05-25 雀巢产品技术援助有限公司 美拉德风味组合物及此类组合物的制备方法
CN102762110A (zh) * 2009-12-18 2012-10-31 雀巢产品技术援助有限公司 含有非水极性溶剂的美拉德风味组合物及制备该组合物的方法
US20140335263A1 (en) * 2010-08-23 2014-11-13 Epc (Beijing) Natural Products Co., Ltd. Rebaudioside a and stevioside compositions
US20150327584A1 (en) * 2014-05-19 2015-11-19 Epc (Beijing) Natural Products Co., Ltd. Stevia sweetener with improved solubility
CN103492403B (zh) * 2011-03-17 2016-04-06 伊比西(北京)植物药物技术有限公司 莱鲍迪甙b及其衍生物
WO2017075257A2 (fr) * 2015-10-29 2017-05-04 Senomyx, Inc. Édulcorants à intensité élevée
WO2017218072A1 (fr) * 2016-06-14 2017-12-21 Purecircle Usa Inc. Compositions de glycosides de stéviol, procédés de production et utilisations

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101652342A (zh) * 2007-03-30 2010-02-17 吉万奥丹股份有限公司 遮蔽不适感感觉的有机化合物
CN102076223A (zh) * 2008-06-24 2011-05-25 雀巢产品技术援助有限公司 美拉德风味组合物及此类组合物的制备方法
CN102762110A (zh) * 2009-12-18 2012-10-31 雀巢产品技术援助有限公司 含有非水极性溶剂的美拉德风味组合物及制备该组合物的方法
US20140335263A1 (en) * 2010-08-23 2014-11-13 Epc (Beijing) Natural Products Co., Ltd. Rebaudioside a and stevioside compositions
CN103492403B (zh) * 2011-03-17 2016-04-06 伊比西(北京)植物药物技术有限公司 莱鲍迪甙b及其衍生物
US20150327584A1 (en) * 2014-05-19 2015-11-19 Epc (Beijing) Natural Products Co., Ltd. Stevia sweetener with improved solubility
WO2017075257A2 (fr) * 2015-10-29 2017-05-04 Senomyx, Inc. Édulcorants à intensité élevée
WO2017218072A1 (fr) * 2016-06-14 2017-12-21 Purecircle Usa Inc. Compositions de glycosides de stéviol, procédés de production et utilisations

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WANG, YONGHUA: "Maillard Reaction", FOOD FLAVOR CHEMISTRY, 30 June 2015 (2015-06-30), pages 42 - 47 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021233242A1 (fr) * 2020-05-19 2021-11-25 Epc Natural Products Co., Ltd. Compositions édulcorantes et aromatisantes contenant des glycosides terpéniques
WO2021232750A1 (fr) * 2020-05-19 2021-11-25 Epc Natural Products Co., Ltd. Compositions d'édulcorant et d'arôme
CN115835784A (zh) * 2020-05-19 2023-03-21 伊比西(北京)植物药物技术有限公司 甜味剂和风味剂组合物
CN113749257A (zh) * 2020-06-01 2021-12-07 鲁南制药集团股份有限公司 一种益生菌组合物及其在调味面制品中的应用
CN112493481A (zh) * 2020-11-30 2021-03-16 李军 一种运动营养补充含片及其制备方法
CN112931632A (zh) * 2021-03-12 2021-06-11 石家庄君乐宝乳业有限公司 炭烧干酪制品及其制备方法
CN113397117A (zh) * 2021-06-30 2021-09-17 四川好哥们食品有限公司 一种方便即食型冷吃食品的制备方法
WO2023242015A3 (fr) * 2022-06-14 2024-02-29 Givaudan Sa Compositions contenant de la brazzéine

Similar Documents

Publication Publication Date Title
US11985994B2 (en) Sweetener and flavor compositions, methods of making and methods of use thereof
CN112218542B (zh) 甜味剂和风味剂组合物，其制备方法和使用方法
WO2019217258A1 (fr) Édulcorant naturel de bon goût et arôme
WO2019214567A1 (fr) Compositions d'édulcorant et d'arôme, leurs procédés de fabrication et leurs procédés d'utilisation
US11751593B2 (en) Sweetener and flavor compositions, methods of making and methods of use thereof
JP7474201B2 (ja) 甘味料および香料組成物、製造方法およびそれらの使用方法
WO2020123067A2 (fr) Compositions d'édulcorant et d'arôme, leurs procédés de fabrication et leurs procédés d'utilisation
US20230082165A1 (en) Tasteful natural sweetener and flavor

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19800844

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2020563513

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2019264701

Country of ref document: AU

Date of ref document: 20190506

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 19800844

Country of ref document: EP

Kind code of ref document: A1