US20200268027A1 - Stabilized steviol glycoside compositions and uses thereof - Google Patents

Stabilized steviol glycoside compositions and uses thereof Download PDF

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US20200268027A1
US20200268027A1 US16/753,731 US201816753731A US2020268027A1 US 20200268027 A1 US20200268027 A1 US 20200268027A1 US 201816753731 A US201816753731 A US 201816753731A US 2020268027 A1 US2020268027 A1 US 2020268027A1
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acid
composition
steviol glycoside
ester
reb
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Dan S. Gaspard
Adam T. ZARTH
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Cargill Inc
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/34—Tea substitutes, e.g. matè; Extracts or infusions thereof
    • 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
    • A23L2/56—Flavouring or bittering agents
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/68—Acidifying substances
    • 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
    • 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
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    • A—HUMAN NECESSITIES
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    • 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
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    • 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
    • A23L27/88—Taste or flavour enhancing agents
    • 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
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
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    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
    • B01D15/361—Ion-exchange
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/256—Polyterpene radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/14—Extraction; Separation; Purification
    • C07K1/16—Extraction; Separation; Purification by chromatography
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/14—Extraction; Separation; Purification
    • C07K1/16—Extraction; Separation; Purification by chromatography
    • C07K1/18—Ion-exchange chromatography
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/15—Flavour affecting agent
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
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    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/31—Extraction of the material involving untreated material, e.g. fruit juice or sap obtained from fresh plants
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K2236/30—Extraction of the material
    • A61K2236/39—Complex extraction schemes, e.g. fractionation or repeated extraction steps

Definitions

  • Steviol glycosides are currently being investigated as sweetening agents for use in foods, beverages, pharmaceuticals, and oral hygiene/cosmetic products, including in beverages such as carbonated soft drinks.
  • SEs solubility enhancers
  • steviol glycosides can provide a non-caloric option for sweetening such products, there can be challenges to preparing such products with steviol glycosides. Though they can be stable at neutral pH, in some cases, steviol glycoside compositions can have limited chemical stability, especially at higher concentrations, over longer storage times at low pH and/or elevated temperatures. For example, beverage concentrates such as fountain syrups or throw syrups inherently have a low pH and can require storage over time, sometimes at elevated temperatures.
  • the disclosure provides, among other things, the use of steviol glycoside stabilizing compounds to enhance the chemical stability of SGs, such that the SGs can be used to prepare compositions with increased chemical stability, especially at higher SG concentrations and over longer storage times.
  • the steviol glycoside stabilizing compounds can also enhance the chemical stability of SGs under acidic conditions and/or at elevated temperatures.
  • This disclosure also describes the enhanced chemical stability of the steviol glycoside stabilizing compounds themselves, which are less subject to acidic hydrolysis and/or oxidation in the presence of SGs. This effect appears to be concentration dependent, with higher concentrations yielding greater stability. This finding opens up the possibility of using SGs in water enhancers, coffee syrups, and liquid stevia products where the SG concentration is higher, the desired shelf-life is longer, and/or the pH can be acidic.
  • FIG. 1 is a flow diagram of an example of a method for making a composition comprising steviol glycoside stabilizing compounds, such as caffeic acid, monocaffeoylquinic acids, and dicaffeoylquinic acids, and salts thereof.
  • steviol glycoside stabilizing compounds such as caffeic acid, monocaffeoylquinic acids, and dicaffeoylquinic acids, and salts thereof.
  • FIG. 2 is a flow diagram of another example of a method for making a composition comprising steviol glycoside stabilizing compounds, such as caffeic acid, monocaffeoylquinic acids, and dicaffeoylquinic acids, and salts thereof.
  • steviol glycoside stabilizing compounds such as caffeic acid, monocaffeoylquinic acids, and dicaffeoylquinic acids, and salts thereof.
  • FIG. 3 is a flow diagram of another example of a method for making a composition comprising steviol glycoside stabilizing compounds, such as caffeic acid, monocaffeoylquinic acids, and dicaffeoylquinic acids, and salts thereof.
  • steviol glycoside stabilizing compounds such as caffeic acid, monocaffeoylquinic acids, and dicaffeoylquinic acids, and salts thereof.
  • FIG. 4 is a flow diagram of another example of a method for making a composition comprising steviol glycoside stabilizing compounds, such as caffeic acid, monocaffeoylquinic acids, and dicaffeoylquinic acids, and salts thereof.
  • steviol glycoside stabilizing compounds such as caffeic acid, monocaffeoylquinic acids, and dicaffeoylquinic acids, and salts thereof.
  • compositions comprising a steviol glycoside (SG) and a steviol glycoside stabilizing compound in an amount effective to reduce degradation of the SG.
  • the compositions comprising the SG and the steviol glycoside stabilizing compound can be formulated in any suitable way, including as an aqueous composition.
  • steviol glycoside stabilizing compounds significantly increases the stability of SGs under most conditions, including at higher concentrations of SG and over longer storage times. Additionally, the presence of steviol glycoside stabilizing compounds significantly increases the stability of SGs under acidic conditions and/or at elevated temperatures. For example, in the presence of the steviol glycoside stabilizing compounds described herein, one can not only access SG concentrations of up to 35 wt. % (e.g., from about 1 wt. % to about 35 wt. %, with 5 wt.
  • the SGs will be chemically stable at acidic pH over a period of greater than 72 days, or even for a period of one year or longer.
  • the SG/steviol glycoside stabilizing compound compositions are chemically stable for weeks, months or even years, even at acidic pHs and/or elevated temperatures.
  • the chromatographic analysis can be performed on a C18-based reversed-phase chromatography column at elevated temperature under gradient conditions, utilizing trifluoroacetic acid in water and acetonitrile. SGs can be detected utilizing a UV detector set to 210 nm. A linear calibration curve can be applied using Reb A standard as a reference solution.
  • the amount of steviol glycoside stabilizing compound effective to reduce degradation of SG is an amount to chemically stabilize the SG over higher concentrations of SG and/or over longer storage times.
  • the amount of SG and/or steviol glycoside stabilizing compound can be at least 1 wt %, at least 3 wt. %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 30 wt. %; about 1 wt % to about 35 wt. %, about 5 wt. % to about 15 wt %, about 1 wt. % to about 5 wt % or about 5 wt. % to about 20 wt %, about And within these stated ranges, the SG and the steviol glycoside stabilizing compound can be chemically stable for days, weeks, months or years.
  • the amount of steviol glycoside stabilizing compound effective to reduce degradation of SG can be determined by an accelerated chemical stability assay.
  • the “amount of steviol glycoside stabilizing compound effective to reduce degradation of the steviol glycoside” is an amount such that at least about 10% (e.g., at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95%; or from about 10% to about 100%, about 20% to about 80%, about 30% to about 95%, about 40% to about 80%, about 60% to about 90% or about 70% to about 99% or more) relative to an initial steviol glycoside concentration remains when the stabilized steviol glycoside composition is subjected to storage for 7 days at 40° C. in a 5% phosphoric acid solution. In some cases, there is statistically less degradation of the steviol glycosides than when steviol glycoside stabilizing compound is absent.
  • compositions comprising a SG and a steviol glycoside stabilizing compound can have a pH of less than about 5 (e.g., less than about 4, less than about 3, less than about 2.5, less than about 2, less than about 1.7, less than about 1.5, less than about 1, much less than about 1; about 0.1 to about 4, about 1 to about 4, about 0.5 to about 2 or about 1 to about 3).
  • compositions comprising a SG and a steviol glycoside stabilizing compound are storable at room temperature, at below room temperature (e.g., 4° C.) or at above room temperature (e.g., at 40° C.), without any substantial degradation of the steviol glycoside.
  • compositions comprising a SG and a steviol glycoside stabilizing compound can comprise any suitable steviol glycoside, such as stevioside, Reb A, Reb C, dulcoside A, Reb M, Reb B, Reb D, and Reb E and salts thereof (in cases where compounds can form salts, such as in the case of Reb B, steviolbioside, and steviol-13-O-glucoside (13-SMG)).
  • the steviol glycoside can be Reb M, Reb A or mixtures of one or more of the aforementioned steviol glycosides.
  • the steviol glycoside comprises one or more steviol glycosides selected from the list consisting of Reb A, Reb B, Reb C, Reb D, Reb E, Reb F, Reb M, Reb N, Reb O, rubusoside, dulcoside A, Reb I, Reb Q, 1,2-stevioside, 1,3-stevioside, steviol-1,2-bioside, steviol-1,3-bioside, 13-SMG, steviol-19-O-glucoside (19-SMG), and steviol glycosides with 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or more sugar additions, such as glucose, rhamnose, or xylose as three examples.
  • steviol glycosides selected from the list consisting of Reb A, Reb B, Reb C, Reb D, Reb E, Reb F, Reb M, Reb N, Reb O, rubusoside, dulcoside A, Reb I, Reb Q, 1,2-stevioside, 1,3-stevioside, steviol-1,2-bioside, steviol-1,3-bio
  • compositions comprising a SG and a steviol glycoside stabilizing compound can comprise any suitable steviol glycoside at any suitable concentration.
  • the compositions comprising a SG and a steviol glycoside stabilizing compound can comprise any suitable amount of steviol glycoside, such as at least about 0.03 wt. % (e.g., at least about 0.1 wt. %, at least about 0.5 wt. %, at least about 0.6 wt. %, at least about 1 wt. %, at least about 1.5 wt. %, at least about 2.5 wt. %, at least 3 wt. %, at least about 5 wt. %, at least about 6 wt.
  • wt. % at least about 10 wt. %, at least about 15 wt. %, at least about 20 wt. %, at least about 25 wt. %, at least about 30 wt. %, at least about 35 wt. %, or up to about 40 wt. %; about 0.03 wt. % to about 5 wt. %, about 0.1 wt. % to about 10 wt. %, about 1 wt. % to about 4 wt. %, about 0.1 wt. % to about 5 wt. %, about or about 1 wt. % to about 5 wt. %) steviol glycoside.
  • compositions comprising a SG and a steviol glycoside stabilizing compound can comprise any suitable steviol glycoside at any suitable concentration.
  • the compositions comprising a SG and a steviol glycoside stabilizing compound can comprise concentrated products that are diluted by the consumer for consumer use. For example, beverage concentrates such as throw syrups are diluted six to seven times for use and flavored water enhancer liquids are diluted up to 100 times.
  • a beverage concentrate product comprising the compositions comprising a SG and a steviol glycoside stabilizing compound can comprise between about 1,800 ppm and about 10,000 ppm (e.g., about 2,000 ppm to about 5,000 ppm, about 2,000 ppm to about 8,000 ppm, about 3,000 ppm to about 5,000 ppm or about 2,500 ppm to about 7,500 ppm) steviol glycoside.
  • ppm e.g., about 2,000 ppm to about 5,000 ppm, about 2,000 ppm to about 8,000 ppm, about 3,000 ppm to about 5,000 ppm or about 2,500 ppm to about 7,500 ppm
  • compositions comprising a SG and a steviol glycoside stabilizing compound can comprise between about 1.0 wt. % and about 10 wt. % (e.g., about 4 wt. % to about 10 wt. %, about 5 wt. % to about 10 wt. %, about 7 wt. % to about 9 wt. % or about 8 wt. % to about 10 wt. %) steviol glycoside.
  • compositions comprising a SG and a steviol glycoside stabilizing compound can comprise any suitable additives including buffering agent, acidulants, such as citric acid, antimicrobial agents, such as benzoic acid and sorbic acid (and salts thereof), natural colors, natural flavors, artificial flavors, artificial colors, and artificial sweeteners.
  • acidulants such as citric acid
  • antimicrobial agents such as benzoic acid and sorbic acid (and salts thereof)
  • natural colors natural flavors, artificial flavors, artificial colors, and artificial sweeteners.
  • steviol glycoside stabilizing compounds include:
  • caffeic acid an ester of caffeic acid, an ester of caffeic acid and quinic acid, an ester of caffeic acid and quinic acid comprising a single caffeic acid moiety (e.g., chlorogenic, cryptochlorogenic, and neochlorogenic acid; structures of each are provided herein), an ester of caffeic acid and quinic acid comprising more than one caffeic acid moiety (e.g., 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylqunic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid; structures of each are provided herein);
  • a single caffeic acid moiety e.g., chlorogenic, cryptochlorogenic, and neochlorogenic acid; structures of each are provided herein
  • an ester of caffeic acid and quinic acid comprising more than one caffeic acid moiety
  • ferulic acid an ester of ferulic acid, an ester of ferulic acid and quinic acid, an ester of ferulic acid and quinic acid comprising a single ferulic acid moiety, an ester of ferulic acid and quinic acid comprising more than one ferulic acid moiety;
  • quinic acid a quinic acid derivative, an ester of quinic acid, an ester of a quinic acid derivative;
  • p-coumaric acid an ester of p-coumaric acid, an ester of p-coumaric acid and quinic acid, an ester of p-coumaric acid and quinic acid comprising a single p-coumaric acid moiety, an ester of p-coumaric acid and quinic acid comprising more than one p-coumaric acid moiety;
  • tartaric acid a tartaric acid derivative, an ester of tartaric acid, an ester of a tartaric acid derivative, and
  • 3-O-feruloylquinic acid 4-O-feruloylquinic acid, 5-O-feruloylquinic acid, 3,4-diferuloylquinic acid, 3,5-diferuloylquinic acid, 4,5-diferuloylquinic acid.
  • Caffeic Acid has the Structure:
  • Ferulic Acid has the Structure:
  • p-Coumaric Acid has the Structure:
  • Sinapic Acid has the Structure:
  • Tartaric Acid has the Structure:
  • esters of the various acids contemplated herein include the ester of caffeic acid and quinic acid, which includes monocaffeoylqunic acids (e.g., chlorogenic acid, neochlorogenic acid, and cryptochlorogenic acid), and dicaffeoylqunic acids (e.g., 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylqunic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid), and salts thereof:
  • monocaffeoylqunic acids e.g., chlorogenic acid, neochlorogenic acid, and cryptochlorogenic acid
  • dicaffeoylqunic acids e.g., 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylqunic acid, 3,5-
  • 4,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 3,4-dicaffeoylquinic acid being most prevalent in the compositions contemplated herein and most prevalent in abundant in stevia , yerba mate, globe artichoke, and green coffee.
  • esters of the various acids contemplated herein include the ester of caffeic acid and tartaric acid, which includes cichoric acid having the structure:
  • steviol glycoside stabilizing compounds can be isolated from botanical sources, including but not limited to botanical sources such as eucommoia ulmoides , honeysuckle, Nicotiana benthamiana , globe artichoke, cardoon, stevia Rebaudiana , monkfruit, coffee, coffee beans, green coffee beans, tea, white tea, yellow tea, green tea, oolong tea, black tea, red tea, post-fermented tea, bamboo, heather, sunflower, blueberries, cranberries, bilberries, grouseberries, whortleberry, lingonberry, cowberry, huckleberry, grapes, chicory, eastern purple coneflower, echinacea , Eastern pellitory-of-the-well, Upright pellitory, Lichwort, Greater celandine, Tetterwort, Nipplewort, Swallowwort, Bloodroot, Common nettle, Stinging nettle, Potato, Potato leaves, Eggplant, Aubergine, Tomato, Cherry tomato, Bitter apple
  • compositions comprising a SG and a steviol glycoside stabilizing compound can comprise any suitable amount of steviol glycoside stabilizing compound, such as at least about 0.03 wt. % (e.g., at least about 0.1 wt. %, at least about 0.5 wt. %, at least about 0.6 wt. %, at least about 1 wt. %, at least about 1.5 wt. %, at least about 2.5 wt. %, at least 3 wt. %, at least about 5 wt. %, at least about 6 wt. %, at least about 10 wt. %, at least about 15 wt. %, at least about 20 wt.
  • steviol glycoside stabilizing compound such as at least about 0.03 wt. % (e.g., at least about 0.1 wt. %, at least about 0.5 wt. %, at least about 0.6 wt. %, at least about 1
  • steviol glycoside stabilizing compound steviol glycoside stabilizing compound.
  • compositions comprising a SG and a steviol glycoside stabilizing compound can comprise a 1:0.3 to 1:3 (e.g., 1:1 to 1:1.5; or 1:1 to 1:2) ratio by weight of steviol glycoside to steviol glycoside stabilizing compound.
  • aforementioned acids can be considered weak acids, they can each exist in at least one of their conjugate acid form, conjugate base form (e.g., in their salt form), and mixed conjugate acid-conjugate base form, wherein a fraction (e.g., mole fraction) of the compounds exist in the conjugate acid form and another fraction exist in the conjugate base form.
  • the fraction of conjugate acid form to conjugate base of each acid will depend on various factors, including the pK a of each compound and the pH of the composition.
  • salts of any of the aforementioned acids include, but are not limited to, quaternary ammonium, sodium, potassium, lithium, magnesium, and calcium salts of the one or more steviol glycoside stabilizing compounds, and the like.
  • An example of a method for making a composition comprising one or more steviol glycoside stabilzing compounds, and salts thereof, comprises:
  • composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof, comprises:
  • Step (a) of the methods described herein involve contacting yerba mate biomass with an aqueous composition to obtain an initial extract comprising one or more steviol glycoside stabilizing compounds, and salts thereof (e.g., quaternary ammonium, sodium, potassium, lithium, magnesium, and calcium salts).
  • an initial extract comprising one or more steviol glycoside stabilizing compounds, and salts thereof (e.g., quaternary ammonium, sodium, potassium, lithium, magnesium, and calcium salts).
  • the aqueous composition can comprise water and not contain any co-solvents, such as organic solvents. But the aqueous composition can comprise co-solvents, in addition to water. Suitable co-solvents include organic solvents, such as, (C 1 -C 4 )akanols and mixtures of (C 1 -C 4 )akanols.
  • the aqueous composition can be buffered with any suitable buffering system, including, but not limited to, a phosphate, citrate, ascorbate, lactate, acetate, and the like. Buffers can be in the range of 1-1000 mM of the anion.
  • water acidified to pH 5-6 with hydrochloric acid, sulfuric acid, nitric acid or the like can be useful in the aqueous composition, with or without a co-solvent.
  • pure water made basic to pH 7-11 with hydroxide, such as with sodium or potassium hydroxide can be useful in the aqueous composition, with or without a co-solvent.
  • the term “yerba mate biomass” generally refers to any and all parts of the yerba mate plant, such as Ilex paraguariensis , including the yerba mate plant leaves, stalks, stems, tops, roots, and the like.
  • the yerba mate biomass can be in any suitable form including in comminuted form resulting from, e.g., from chopping the yerba mate biomass prior to and/or during the contacting with the aqueous composition.
  • the yerba mate biomass can be comminuted in a suitable container and the aqueous composition can be added to the comminuted yerba mate biomass, thus “contacting” the yerba mate biomass.
  • the yerba mate biomass can be stirred, sonicated or otherwise agitated prior to and/or during the contacting to, among other things, maximize the extraction of, among other of the acids described herein, the one or more steviol glycoside stabilizing compounds, and salts thereof.
  • the initial extract can be carried through to step (c) as-is or bulk solids and or plant solids present, such as comminuted yerba mate plant leaves, stalks, tops, roots, and the like, can be removed in step (b) of the methods described herein.
  • step (b) When step (b) is carried out, one obtains a second initial extract.
  • Bulk solids can be removed by any suitable method, including centrifugation, skimming, or filtration.
  • the initial extract can be filtered using any suitable filtration method, including gravity filtration or vacuum filtration through any suitable filter, so long as the filter does not substantially retain the one or more steviol glycoside stabilizing compounds, and salts thereof, including a paper filter (e.g., low ash filter paper, such as Whatman 44 or 54 low ash filter paper), a nylon filter, polyethersulfone filter, a glass fiber filter, a pad of diatomaceous earth, and the like.
  • a paper filter e.g., low ash filter paper, such as Whatman 44 or 54 low ash filter paper
  • nylon filter such as Whatman 44 or 54 low ash filter paper
  • polyethersulfone filter such as Whatman 44 or 54 low ash filter paper
  • glass fiber filter such as Whatman 44 or 54 low ash filter paper
  • pad of diatomaceous earth and the like.
  • Step (c) of the methods described herein involves adjusting the volume of the initial extract or second initial extract with a first aqueous composition or a second aqueous composition, respectively, to obtain an adjusted initial extract or adjusted second initial extract.
  • the first and second aqueous compositions can be different or the same.
  • the adjusted initial extract or adjusted second initial extract can be filtered at this point or can be carried through to step (d) as-is.
  • the initial extract or the second initial extract can be filtered using any suitable filtration method, including gravity filtration or vacuum filtration through any suitable filter, so long as the filter does not substantially retain the one or more steviol glycoside stabilizing compounds, and salts thereof, including a paper filter (e.g., low ash filter paper, such as Whatman 44 or 54 low ash filter paper), a nylon filter, polyethersulfone filter, a glass fiber filter, a pad of diatomaceous earth, and the like.
  • a paper filter e.g., low ash filter paper, such as Whatman 44 or 54 low ash filter paper
  • a nylon filter such as Whatman 44 or 54 low ash filter paper
  • polyethersulfone filter such as Whatman 44 or 54 low ash filter paper
  • glass fiber filter such as Whatman 44 or 54 low ash filter paper
  • the volume of the initial extract or second initial extract can be adjusted with a sufficient amount of an aqueous composition (e.g., water) to obtain an adjusted initial extract or adjusted second initial extract to, among other things, increase the binding of the one or more steviol glycoside stabilizing compounds, and salts thereof, to the ion exchange chromatography column used in step (d) of the methods described herein, relative to an unadjusted initial extract or an unadjusted second initial extract.
  • an aqueous composition e.g., water
  • the volume of the initial extract or second initial extract can be adjusted to, among other things, adjust the amount of organic solvent, when present, in the initial extract or second initial extract.
  • the volume of the initial extract or second initial extract can be adjusted such that the adjusted initial extract or adjusted second initial extract comprises less than about 60%, less than about 50%, less than about 40%, less than about 30%, less than about 20%, less than about 10%, less than about 5%, less than about 1% or even about 0% by volume organic solvent, the balance being water; or from about 0% to about 40%, about 0% to about 30%, about 10% to about 40%, about 10% to about 30%, about 20% to about 40%, about 30% to about 40%, or about 35% by volume organic solvent, the balance being water.
  • the chromatographing can be performed with an aqueous composition (e.g., an aqueous composition comprising a (C 1 -C 4 )akanol) as eluent (e.g., an aqueous composition comprising from about 0% to about 40%, about 0% to about 30%, about 10% to about 40%, about 10% to about 30%, about 20% to about 40%, about 30% to about 40%, or about 35% by volume (C 1 -C 4 )akanol, the balance being water), leaving one or more steviol glycoside stabilizing compounds, and salts thereof, adsorbed on the weak ion exchange chromatography column, while eluting other compounds including caffeine, rutin (also known as rutoside, quercetin-3-O-rutinoside, and sophorin)
  • rutin also known as rutoside, quercetin-3-O-rutinoside, and sophorin
  • Step (d) of the methods described herein can decrease the concentration of at least one of caffeine, rutin, and rutin isomers to a concentration of less than 1%, less than 0.5%, less than 0.1%, less than 0.05%, less than 0.01% or less than 0.001% by mass.
  • the instant disclosure therefore contemplates yerba mate extracts comprising less than 0.1% of at least one of caffeine, rutin, and rutin isomers by mass.
  • the instant disclosure also contemplates yerba mate extracts comprising less than 0.5% by mass of each one of caffeine, rutin, and rutin isomers and a less than about 1% by mass of caffeine, rutin, and rutin isomers combined.
  • the instant disclosure also contemplates yerba mate extracts that are effectively free of at least one of caffeine, rutin, and rutin isomers (e.g., free of caffeine, free of rutin, free of rutin isomers, and/or free of caffeine, rutin, and rutin isomers).
  • the ion exchange stationary phase is non-limiting and can be any suitable ion exchange chromatography stationary phase.
  • suitable ion exchange chromatography stationary phases include ANX-SEPHAROSE® fast flow resin, DEAE SEPHAROSE®, DEAE SEPHADEX® A25 resin, Reite RAM2, Reite MG1P, AMBERLITE® (FPA 53; FPA 55; CG-50 Type I; IRC-50; IRC-50S; and IRP-64), DIAION WA10, and DOWEX® CCR-3.
  • the ion exchange chromatography stationary phase can optionally be pre-conditioned with an aqueous composition (e.g., an aqueous composition comprising a (C 1 -C 4 )alkanol), such as an aqueous composition comprising from about 0% to about 40%, about 0% to about 30%, about 10% to about 40%, about 10% to about 30%, about 20% to about 40%, about 30% to about 40%, or about 35% by volume (C 1 -C 4 )alkanol, the balance being water, prior to the chromatographing of the adjusted initial extract or adjusted second initial extract.
  • the weak ion exchange chromatography column can be pre-conditioned with about 2 or more bed volumes (BV) at a flow rate of about 2 BV/h.
  • the pH of the weak ion exchange chromatography column can optionally be adjusted prior to the chromatographing of the adjusted initial extract or adjusted second initial extract.
  • the pH of the weak ion exchange chromatography column can be adjusted prior to the chromatographing with any suitable acid (e.g., hydrochloric acid) such that the pH of the weak ion exchange chromatography column (e.g., the pH of the resir/stationary phase) is a pH of less than about 10, about 9 or less, about 8 or less, about 7 or less, about 6 or less, about 5 or less, about 4 or less, about 3 or less; or a pH of about 2 to about 10, about 3 to about 8, about 5 to about 9, about 2 to about 6; about 3 to about 4; or about 3 to about 6.
  • any suitable acid e.g., hydrochloric acid
  • the pH of the weak ion exchange chromatography column can be adjusted before or after the column is optionally pre-conditioned with the aqueous composition comprising a (C 1 -C 4 ) prior to the chromatographing of the adjusted initial extract or adjusted second initial extract.
  • the adjusted initial extract or adjusted second initial extract can be loaded onto the column at any suitable rate, such as at a rate of above 2 BV/h (bed volumes per hour).
  • the column can be washed with any suitable volume of an aqueous composition comprising a (C 1 -C 4 )alkanol (e.g., at least about 2 BV, at least about 3 BV or at least about 4 BV of an aqueous composition comprising from about 10% to about 40%, about 10% to about 30%, about 20% to about 40%, about 30% to about 40%, or about 35% by volume (C 1 -C 4 )alkanol, the balance being water) at any suitable rate, such as at a rate of about 2 BV/h.
  • the volume of aqueous composition comprising a (C 1 -C 4 )alkanol can be discarded, as it will contain, among other things, caffeine, rutin, and rutin isomers.
  • Step (e) of the methods described herein involves eluting the adsorbed one or more steviol glycoside stabilizing compounds, and salts thereof, from the weak ion exchange chromatography column to obtain a first eluent comprising one or more steviol glycoside stabilizing compounds, and salts thereof.
  • the eluting is performed under any conditions suitable to elute the one or more steviol glycoside stabilizing compounds, and salts thereof from the column.
  • An example of suitable conditions to elute the one or more steviol glycoside stabilizing compounds, and salts thereof from the column include eluting the column with any suitable volume of a solution comprising a salt (e.g., sodium chloride, potassium chloride, ammonium chloride, sodium sulfate, potassium sulfate, sodium phosphate, potassium phosphate, and the like).
  • solutions comprising a salt include solutions comprising at least one salt (e.g., about 5 wt. % to about 25 wt. %, about 15 wt. % to about 20 wt. % or about 5 wt. % to about 10 wt.
  • aqueous composition comprising a (C 1 -C 4 )alkanol (e.g., at least about 2 BV, at least about 3 BV or at least about 4 BV of an aqueous composition comprising from about 10% to about 60%, about 20% to about 50%, about 30% to about 55%, about 40% to about 60%, or about 50% by volume (C 1 -C 4 )alkanol).
  • a (C 1 -C 4 )alkanol e.g., at least about 2 BV, at least about 3 BV or at least about 4 BV of an aqueous composition comprising from about 10% to about 60%, about 20% to about 50%, about 30% to about 55%, about 40% to about 60%, or about 50% by volume (C 1 -C 4 )alkanol).
  • suitable conditions to elute the one or more steviol glycoside stabilizing compounds, and salts thereof from the column include eluting the column with any suitable volume of a solution comprising an acid (e.g., hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, formic acid, and the like).
  • solutions comprising an acid include solutions comprising hydrochloric acid and the like and optionally acids solutions comprising an aqueous composition comprising from about 10% to about 60%, about 20% to about 50%, about 30% to about 55%, about 40% to about 60%, or about 50% by volume (C 1 -C 4 )alkanol).
  • the first eluent comprising the one or more steviol glycoside stabilizing compounds, and salts thereof comprises a solvent.
  • the solvent can be removed in a step (f) to dryness or it can be removed to a point where a volume of an aqueous composition comprising a (C 1 -C 4 )alkanol remains as a solvent (e.g., about 50%, about 40%, about 30% about 20%, about 10% or about 5% of an original, total volume of the eluent) to form a concentrate, though the ratio of components that make up the aqueous composition comprising a (C 1 -C 4 )alkanol may or may not be different from the ratio of components that made up the aqueous composition comprising a (C 1 -C 4 )alkanol that was used to elute the adsorbed one or more steviol glycoside stabilizing compounds, and salts thereof.
  • the solvent in the eluent comprising the one or more steviol glycoside stabilizing compounds, and salts thereof can be removed to a point where a volume of an aqueous composition comprising a (C 1 -C 4 )alkanol remains, wherein the aqueous composition comprising a (C 1 -C 4 )alkanol comprises less than about 10%, less than about 5%, less than about 2% or less than about 1% by volume (C 1 -C 4 )alkanol.
  • Suitable conditions for removing solvent from the eluent comprising, among other of the acids described herein, the one or more steviol glycoside stabilizing compounds, and salts thereof, to form a concentrate comprising, among other of the acids described herein, the one or more steviol glycoside stabilizing compounds, and salts thereof include blowing an inert gas (e.g., nitrogen gas) over the surface of the eluent.
  • the eluent can be heated while blowing the nitrogen gas or it can be at room temperature (e.g., 25° C.).
  • Other conditions for removing the solvent in the eluent include applying a vacuum to the container containing the eluent. The vacuum can be applied with the eluent at room temperature or while heating the container.
  • Yet other conditions for removing solvent in the eluent include passing the eluent through a wiped film evaporator or an agitated thin film evaporator.
  • the pH of the concentrate can be adjusted at this point to obtain a pH-adjusted concentrate, though adjusting the pH at this point is optional.
  • the pH of the concentrate can be adjusted to a pH where, among other of the acids described herein, the one or more steviol glycoside stabilizing compounds, and salts thereof are protected from degradation. Suitable pHs include pHs of less than about 6, less than about 5, less than about 4, less than about 3 or less than about 2; such as a pH of from about 2 to about 6, about 2 to about 5, about 2 to about 4, about 3 to about 5 or a pH of about 3.5.
  • the pH of the concentrate can be adjusted by using any suitable acid or base. When an acid is used, the acid can be hydrochloric acid and the like.
  • the pH-adjusted concentrate can be filtered through a polymeric membrane, such as a polyethersulfone (PES) filter having, e.g., 0.2 ⁇ m pore size, or a pleated (flat membrane, vacuum filtration) or a pleated PES membrane, depending on the volume of the concentrate or the pH-adjusted concentrate.
  • a polymeric membrane such as a polyethersulfone (PES) filter having, e.g., 0.2 ⁇ m pore size, or a pleated (flat membrane, vacuum filtration) or a pleated PES membrane, depending on the volume of the concentrate or the pH-adjusted concentrate.
  • PES polyethersulfone
  • performing the one or more steps under an inert atmosphere can reduce the formation of highly colored polymeric substances that either natively exist in the yerba mate biomass or form at one or more of the steps described herein.
  • the concentrate can be decolored by any suitable means, including ultrafiltration (e.g., filtering through a molecular weight cutoff membrane, size-exclusion chromatography or gel permeation).
  • ultrafiltration e.g., filtering through a molecular weight cutoff membrane, size-exclusion chromatography or gel permeation.
  • Ultrafiltration accomplishes, among other things, decoloration of a concentrate that can be highly colored. While not wishing to be bound by any specific theory, it is believed that ultrafiltration removes highly colored polymeric substances that either natively exist in the yerba mate biomass or form at one or more of the steps described herein.
  • the filtrate from decoloring can be taken on to drying step (h) or it can be desalted in step (g).
  • the concentrate whether it is pH-adjusted, filtered or both pH-adjusted and filtered, can be desalted without first decoloring.
  • the desalting can be accomplished using a nanofiltration membrane and a hydrophobic resin. Those of skill in the art would recognize that when one uses a nanofiltration membrane and a hydrophobic resin one discards the permeate and keeps the retentate.
  • desalting can be accomplished using a hydrophobic resin (e.g., a porous poly divinylbenzene/ethylvinylbenzene matrix, such as SEPABEADSTM SP70), where one would load a pH-adjusted concentrate (e.g., an acidified concentrate, with a pH of less than about 2) comprising less than about 20% by volume (C 1 -C 4 )alkanol.
  • a hydrophobic resin e.g., a porous poly divinylbenzene/ethylvinylbenzene matrix, such as SEPABEADSTM SP70
  • a pH-adjusted concentrate e.g., an acidified concentrate, with a pH of less than about 2
  • C 1 -C 4 alkanol
  • the resin is then washed with dilute alcohol (e.g., less than about 10% by volume (C 1 -C 4 )alkanol, the rest being water having a pH of less than about 2) and then eluted with an aqueous composition comprising about 70% by volume (C 1 -C 4 )alkanol in water to obtain a desalted second eluent comprising one or more steviol glycoside stabilizing compounds, and salts thereof.
  • dilute alcohol e.g., less than about 10% by volume (C 1 -C 4 )alkanol, the rest being water having a pH of less than about 2
  • an aqueous composition comprising about 70% by volume (C 1 -C 4 )alkanol in water to obtain a desalted second eluent comprising one or more steviol glycoside stabilizing compounds, and salts thereof.
  • the solvent in the permeate from the desalting step can be removed to a point where a volume of an aqueous composition comprising a (C 1 -C 4 )alkanol remains as a solvent (e.g., about 50%, about 40%, about 30% about 20%, about 10% or about 5% of an original, total volume of the eluent) to form a first desalted concentrate.
  • a volume of an aqueous composition comprising a (C 1 -C 4 )alkanol remains as a solvent (e.g., about 50%, about 40%, about 30% about 20%, about 10% or about 5% of an original, total volume of the eluent) to form a first desalted concentrate.
  • the solvent in the permeate from the desalting can be removed, to give a second desalted concentrate, to a point where a volume of an aqueous composition comprising a (C 1 -C 4 )alkanol remains, wherein the aqueous composition comprising a (C 1 -C 4 )alkanol comprises less than about 10%, less than about 5%, less than about 2% or less than about 1% by volume (C 1 -C 4 )alkanol.
  • the first desalted concentrate can also have the attributes of the second desalted concentrate, such that the first desalted concentrate also has less than about 10%, less than about 5%, less than about 2% or less than about 1% by volume (C 1 -C 4 )alkanol.
  • Suitable conditions for removing solvent from the permeate comprising one or more steviol glycoside stabilizing compounds, and salts thereof, to form a first/second desalted concentrate comprising one or more steviol glycoside stabilizing compounds, and salts thereof include blowing an inert gas (e.g., nitrogen gas) over the surface of the eluent.
  • the permeate can be heated while blowing the nitrogen gas or it can be at room temperature (e.g., 25° C.).
  • Other conditions for removing the solvent in the eluent include applying a vacuum to the container containing the permeate. The vacuum can be applied with the permeate at room temperature or while heating the container.
  • Yet other conditions for removing solvent in the permeate include passing the permeate through a wiped film evaporator or an agitated thin film evaporator.
  • the concentrate comprising one or more steviol glycoside stabilizing compounds, and salts thereof can be filtered through filter paper to obtain a first filtrate, the first filtrate is ultrafiltered to obtain a second filtrate, and the second filtrate is nanofiltered using a nanofiltration membrane to obtain a first retentate or the second filtrate is eluted through a hydrophobic resin to obtain a desalted second eluent.
  • the concentrate comprising one or more steviol glycoside stabilizing compounds, and salts thereof can be filtered through filter paper to obtain a first filtrate, the first filtrate is nanofiltered using a nanofiltration membrane to obtain a third retentate or the first filtrate is eluted through a hydrophobic resin to obtain a desalted second eluent, and the third retentate or the desalted second eluent is ultrafiltered to obtain a third filtrate.
  • the eluent comprising one or more steviol glycoside stabilizing compounds, and salts thereof can be concentrated to dryness or it can be concentrated to a point where a volume of an aqueous composition comprising a (C 1 -C 4 )alkanol remains. If the eluent is concentrated to dryness, the dry material can be reconstituted using, for example, an aqueous composition comprising a (C 1 -C 4 )alkanol. The reconstituted material can then be filtered as described herein, to among other things, at least one of desalt and decolor.
  • the methods described herein can include step (h) that involves drying first retentate, desalted second eluent or the third filtrate to obtain the composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof.
  • the first retentate, desalted second eluent or the third filtrate can be dried in any suitable manner, including by lyophilization or spray drying.
  • FIG. 1 is a flow diagram of a method 100 for making a composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof.
  • yerba mate biomass is contacted with an aqueous composition containing 50% ethanol/water in a suitable container (e.g., a glass jar) for 1 h (300 g yerba mate biomass into 1.5 L solvent) to obtain an initial extract.
  • the initial extract is filtered using, for example, a ceramic Büchner funnel with Whatman 54 low ash filter paper into glass 4 L side arm flask.
  • the volume of the filtered initial extract is adjusted with an aqueous composition, in this case water, to obtain an adjusted filtered initial extract containing a lower proportion of ethanol, in this case 35% by volume ethanol.
  • the adjusted filtered initial extract can be re-filtered using, for example, a ceramic Büchner funnel with Whatman 44 low ash filter paper into glass 4 L side arm flask.
  • the adjusted filtered initial extract is chromatographed on an ion exchange chromatography stationary phase. For example, AMBERLITE® FPA 53 resin is packed in glass column. The resin is preconditioned with 35% ethanol (2 BV at 2 BV/h).
  • the adjusted filtered initial extract is loaded is loaded (2 BV/h) onto the resin, discarding the loading permeate.
  • the resin is washed with 35% ethanol (4 BV at 2 BV/h) discarding the washing permeate.
  • the one or more steviol glycoside stabilizing compounds, and salts thereof are eluted with 50% ethanol/water, 10% FCC sodium chloride (4 BV, 0.5 BV/h) and the permeate is kept.
  • the column/resin can optionally be regenerated with water (4 BV, 2 BV/h).
  • the eluent/permeate is concentrated to form a concentrate.
  • the concentrate is acidified to a pH of approximately 3.5 and then filtered through a Whatman 44 filter paper on a Büchner funnel followed by 0.2 ⁇ m polyether sulfone (PES) filter.
  • PES polyether sulfone
  • the filtered concentrate is decolored using a molecular weight cutoff membrane (MWCO; e.g., a MWCO membrane that removes materials having a molecular weight of greater than 10 kDA, such as a 3 kDa TURBOCLEAN® NP010 or Synder VT-2B or a 1 kDa Synder XT-2B) to, among other things, decolor the filtered concentrate and obtain a permeate.
  • MWCO molecular weight cutoff membrane
  • a MWCO membrane that removes materials having a molecular weight of greater than 10 kDA, such as a 3 kDa TURBOCLEAN® NP010 or Synder VT-2B or a 1 kDa Synder XT-2B
  • the permeate is filtered through a nanofiltration membrane (e.g., TRISEP XN45 membrane) and the retentate is subsequently dried in operation 120 to obtain the composition comprising one or more steviol glycoside stabilizing compounds
  • FIG. 2 is a flow diagram of a method 200 for making a composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof.
  • yerba mate biomass is contacted with an aqueous composition containing 50% ethanol/water in a suitable container (e.g., a glass jar) for 1 h (300 g yerba mate biomass into 1.5 L solvent) to obtain an initial extract.
  • the initial extract is filtered using, for example, a ceramic Büchner funnel with Whatman 54 low ash filter paper into glass 4 L side arm flask.
  • the volume of the filtered initial extract is adjusted with an aqueous composition, in this case water, to obtain an adjusted filtered initial extract containing a lower proportion of ethanol, in this case 35% by volume ethanol.
  • the adjusted filtered initial extract can be re-filtered using, for example, a ceramic Büchner funnel with Whatman 44 low ash filter paper into glass 4 L side arm flask.
  • the adjusted filtered initial extract is chromatographed on an ion exchange chromatography stationary phase. For example, AMBERLITE® FPA 53 resin is packed in glass column. The resin is preconditioned with 35% ethanol (2 BV at 2 BV/h).
  • the adjusted filtered initial extract is loaded is loaded (2 BV/h) onto the resin, discarding the loading permeate.
  • the resin is washed with 35% ethanol (4 BV at 2 BV/h) discarding the washing permeate.
  • the one or more steviol glycoside stabilizing compounds, and salts thereof are eluted with 50% ethanol/water, 10% FCC sodium chloride (4 BV, 0.5 BV/h) and the permeate is kept.
  • the column/resin can optionally be regenerated with water (4 BV, 2 BV/h).
  • the eluent/permeate is concentrated to form a concentrate, where the volume is approximately one third of the initial volume of eluent/permeate and/or ethanol is less than 1% in the eluent/permeate, thereby obtaining a concentrate.
  • the concentrate is acidified to a pH of approximately 1 and then filtered through a Whatman 44 filter paper on a Büchner funnel followed by 0.2 ⁇ m polyether sulfone (PES) filter.
  • PES polyether sulfone
  • the concentrate is desalted using a hydrophobic resin (e.g., a porous poly divinylbenzene/ethylvinylbenzene matrix, such as SEPABEADSTM SP70) and the solvent in the retentate is removed in operation 217 .
  • a hydrophobic resin e.g., a porous poly divinylbenzene/ethylvinylbenzene matrix, such as SEPABEADSTM SP70
  • the desalted concentrate is decolored using a molecular weight cutoff membrane (MWCO; e.g., a MWCO membrane that removes materials having a molecular weight of greater than 10 kDA, such as a 3 kDa TURBOCLEAN® NP010) to, among other things, decolor the filtered concentrate and obtain a permeate, which is subsequently dried in operation 220 to obtain the composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof.
  • MWCO molecular weight cutoff membrane
  • composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof, the method comprising
  • Steps (i), (ii), and (vi) are performed as described herein for steps (a), (b), and (h).
  • Step (v) is analogous to filtering step (g), except that step (v) involves only decoloring processes, such as ultrafiltration, which includes filtering through a molecular weight cutoff membrane, size-exclusion chromatography, and gel permeation, as discussed herein. Accordingly, the disclosure with regard to steps (a), (b), (g), and (h) apples to steps (i), (ii), (v), and (vi).
  • the aqueous composition can comprise water and not contain any co-solvents, such as organic solvents. But the aqueous composition can comprise co-solvents, in addition to water. Suitable co-solvents include organic solvents, such as, (C 1 -C 4 )alkanols and mixtures of (C 1 -C 4 )alkanols.
  • the yerba mate biomass can be stirred, sonicated or otherwise agitated prior to and/or during the contacting of step (i) to, among other things, maximize the extraction of one or more steviol glycoside stabilizing compounds, and salts thereof.
  • the initial extract can be carried through to step (iii) as-is or bulk solids and or plant solids present, such as comminuted yerba mate plant leaves, stalks, tops, roots, and the like, can be removed in step (ii) of the methods described herein.
  • step (ii) is carried out, one obtains a second initial extract.
  • Bulk solids can be removed by any suitable method, including centrifugation, skimming, or filtration.
  • the initial extract can be filtered using any suitable filtration method, including gravity filtration or vacuum filtration through any suitable filter, so long as the filter does not substantially retain the one or more steviol glycoside stabilizing compounds, and salts thereof, including a paper filter (e.g., low ash filter paper, such as Whatman 44 or 54 low ash filter paper), a nylon filter, polyethersulfone filter, a glass fiber filter, a pad of diatomaceous earth, and the like.
  • a paper filter e.g., low ash filter paper, such as Whatman 44 or 54 low ash filter paper
  • nylon filter such as Whatman 44 or 54 low ash filter paper
  • polyethersulfone filter such as Whatman 44 or 54 low ash filter paper
  • glass fiber filter such as Whatman 44 or 54 low ash filter paper
  • pad of diatomaceous earth and the like.
  • Step (iii) of the methods described herein involves contacting the first or second initial extract with acidified ethyl acetate to obtain an acidic ethyl acetate extract.
  • the acidified ethyl acetate can be prepared in any suitable manner, including by adding any suitable acid, including hydrochloric acid, sulfuric acid, and glacial acetic acid (e.g., 0.01-1% vol/vol).
  • the acidic ethyl acetate extract is washed with water (e.g., three times, with 1:1 vol/vol water).
  • Step (iii) of the methods described herein can be carried out in other suitable ways, including by using ethyl acetate that has not been pre-acidified as described herein (e.g., by pre-washing with glacial acetic acid), but instead by adjusting the pH of the initial or second initial extract with a suitable acid. (e.g., hydrochloric acid and the like), then extracting the pH-adjusted initial or second initial extract with ethyl acetate that has not been pre-acidified. Regardless of the acid used to adjust the pH of the initial extract or the second initial extract, the pH of the initial extract or the second initial extract is adjusted to about 4 or less, 3 or less, about 2 or less, or about 1 or less. The water layers are discarded and the acidic ethyl acetate extract that results is carried on to step (iv).
  • a suitable acid e.g., hydrochloric acid and the like
  • Step (iv) of the methods described herein involves neutralizing the acidic ethyl acetate extract to obtain neutralized ethyl acetate and an aqueous extract.
  • This is accomplished in any suitable way, including washing the acidic ethyl acetate extract with water (e.g., three times, with 1:1 vol/vol water) comprising a suitable base, such as sodium hydroxide, potassium hydroxide, and the like, and combinations thereof.
  • a suitable base such as sodium hydroxide, potassium hydroxide, and the like, and combinations thereof.
  • the one or more steviol glycoside stabilizing compounds, and salts thereof will substantially be in their conjugate base form and will substantially reside in the water layer that forms when the acidic ethyl acetate extract is washed with water comprising a suitable base.
  • aqueous extract comprising the one or more steviol glycoside stabilizing compounds, and salts thereof, whether they emanate from step (iv) or step (iv-a), can then be submitted for step (v) to accomplish, among other things, decoloring of aqueous extract, which can be highly colored.
  • Decoloring can be accomplished by any suitable means, including ultrafiltration (e.g., filtering through a molecular weight cutoff membrane, size-exclusion chromatography, or gel permeation). One obtains a filtrate from decoloring.
  • Ultrafiltration accomplishes, among other things, decoloration of a concentrate that can be highly colored. While not wishing to be bound by any specific theory, it is believed that ultrafiltration removes highly colored polymeric substances that either natively exist in the yerba mate biomass or form at one or more of the steps described herein.
  • steps (i)-(vi) includes a method for making a composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof, the method comprising contacting yerba mate biomass with an aqueous composition to obtain an initial extract;
  • steps (i)-(vi) includes a method for making a composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof, the method comprising contacting yerba mate biomass with an aqueous composition to obtain an initial extract;
  • the methods described herein can include step (vi) that involves drying the decolored aqueous extract to obtain the composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof.
  • the first or second retentates or the third filtrate can be dried in any suitable manner, including by lyophilization or spray drying.
  • the filtrate from operation 304 is extracted in operation 306 with acidified ethyl acetate extraction.
  • the acidified ethyl acetate is washed with water comprising a suitable base, such as sodium hydroxide, potassium hydroxide, and the like, in operation 308 to obtain neutralized ethyl acetate and an aqueous extract
  • a suitable base such as sodium hydroxide, potassium hydroxide, and the like
  • the water layer is filtered to obtain a filtrate.
  • the filtrate is decolored using a 3 kDa molecular weight cutoff membrane (TURBOCLEAN® NP010; six diafiltrations) to, among other things, decolor the aqueous extract, thereby obtaining a decolored aqueous extract.
  • the decolored aqueous extract is dried to obtain the composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof.
  • the filtrate from operation 404 is pH-adjusted to from about 4 to about 7 and the filtrate is extracted in operation 408 with ethyl acetate, while the compounds of interest remain in the aqueous layer.
  • the pH of the aqueous layer is adjusted to less than 2 and the aqueous layer is extracted with ethyl acetate.
  • the ethyl acetate is removed to dryness in operation 407 to obtain a solid.
  • the solid is reconstituted with water and the pH of the water is adjusted to from about 3 to about 7.
  • the one or more steviol glycoside stabilizing compounds will substantially be in their conjugate base form and will dissolve in the water.
  • the water layer is filtered to obtain a filtrate.
  • the filtrate is decolored using a 3 kDa molecular weight cutoff membrane (TURBOCLEAN® NP010; six diafiltrations) to, among other things, decolor the aqueous extract, thereby obtaining a decolored aqueous extract.
  • the decolored aqueous extract is dried to obtain the composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof.
  • composition comprising the one or more steviol glycoside stabilizing compounds, and salts thereof prepared according to the methods described herein can be incorporated into any ingestible composition, including into beverages and food products.
  • the ingestible composition can be a comestible composition or noncomestible composition.
  • “comestible composition” it is meant any composition that can be consumed as food by humans or animals, including solids, gel, paste, foamy material, semi-solids, liquids, or mixtures thereof.
  • noncomestible composition it is meant any composition that is intended to be consumed or used by humans or animals not as food, including solids, gel, paste, foamy material, semi-solids, liquids, or mixtures thereof.
  • the noncomestible composition includes, but is not limited to medical compositions, which refers to a noncomestible composition intended to be used by humans or animals for therapeutic purposes.
  • composition comprising the one or more steviol glycoside stabilizing compounds, and salts thereof prepared according to the methods described herein can be added to a noncomestible composition or non-edible product, such as supplements, nutraceuticals, functional food products (e.g., any fresh or processed food claimed to have a health-promoting and/or disease-preventing properties beyond the basic nutritional function of supplying nutrients), pharmaceutical and over the counter medications, oral care products such as dentifrices and mouthwashes, cosmetic products such as lip balms and other personal care products.
  • a noncomestible composition or non-edible product such as supplements, nutraceuticals, functional food products (e.g., any fresh or processed food claimed to have a health-promoting and/or disease-preventing properties beyond the basic nutritional function of supplying nutrients), pharmaceutical and over the counter medications, oral care products such as dentifrices and mouthwashes, cosmetic products such as lip balms and other personal care products.
  • over the counter (OTC) product and oral hygiene product generally refer to product for household and/or personal use which may be sold without a prescription and/or without a visit to a medical professional.
  • OTC products include, but are not limited to Vitamins and dietary supplements; Topical analgesics and/or anaesthetic; Cough, cold and allergy remedies; Antihistamines and/or allergy remedies; and combinations thereof.
  • Vitamins and dietary supplements include, but are not limited to vitamins, dietary supplements, tonics/bottled nutritive drinks, child-specific vitamins, dietary supplements, any other products of or relating to or providing nutrition, and combinations thereof.
  • composition comprising one or more steviol glycoside stabilizing compounds, and salts thereof prepared according to the methods described herein can be added to food or beverage products or formulations.
  • food and beverage products or formulations include, but are not limited to coatings, frostings, or glazes for comestible products or any entity included in the Soup category, the Dried Processed Food category, the Beverage category, the Ready Meal category, the Canned or Preserved Food category, the Frozen Processed Food category, the Chilled Processed Food category, the Snack Food category, the Baked Goods category, the Confectionary category, the Dairy Product category, the Ice Cream category, the Meal Replacement category, the Pasta and Noodle category, and the Sauces, Dressings, Condiments category, the Baby Food category, and/or the Spreads category.
  • the Soup category refers to canned/preserved, dehydrated, instant, chilled, UHT and frozen soup.
  • soup(s) means a food prepared from meat, poultry, fish, vegetables, grains, fruit and other ingredients, cooked in a liquid which may include visible pieces of some or all of these ingredients. It may be clear (as a broth) or thick (as a chowder), smooth, pureed or chunky, ready to serve, semi condensed or condensed and may be served hot or cold, as a first course or as the main course of a meal or as a between meal snack (sipped like a beverage). Soup may be used as an ingredient for preparing other meal components and may range from broths (consommé) to sauces (cream or cheese based soups).
  • “Dehydrated and Culinary Food Category” usually means: (i) Cooking aid products such as: powders, granules, pastes, concentrated liquid products, including concentrated bouillon, bouillon and bouillon like products in pressed cubes, tablets or powder or granulated form, which are sold separately as a finished product or as an ingredient within a product, sauces and recipe mixes (regardless of technology); (ii) Meal solutions products such as: dehydrated and freeze dried soups, including dehydrated soup mixes, dehydrated instant soups, dehydrated ready to cook soups, dehydrated or ambient preparations of ready-made dishes, meals and single serve entrees including pasta, potato and rice dishes; and (iii) Meal embellishment products such as: condiments, marinades, salad dressings, salad toppings, dips, breading, batter mixes, shelf stable spreads, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes, including recipe mixes for salad, sold as a finished product or as an ingredient within a product, whether dehydrated, liquid or frozen
  • the Beverage category means beverages, beverage mixes and concentrates, including but not limited to, carbonated and non-carbonated beverages, alcoholic and nonalcoholic beverages, ready to drink beverages, liquid concentrate formulations for preparing beverages such as sodas, and dry powdered beverage precursor mixes.
  • the Beverage category also include the alcoholic drinks, the soft drinks, sports drinks, isotonic beverages, and hot drinks.
  • the alcoholic drinks include, but are not limited to beer, cider/perry, FABs, wine, and spirits.
  • the soft drinks include, but are not limited to carbonates, such as colas and non-cola carbonates; fruit juice, such as juice, nectars, juice drinks and fruit flavored drinks; bottled water, which includes sparking water, spring water and purified/table water; functional drinks, which can be carbonated or still and include sport, energy or elixir drinks; concentrates, such as liquid and powder concentrates in ready to drink measure.
  • carbonates such as colas and non-cola carbonates
  • fruit juice such as juice, nectars, juice drinks and fruit flavored drinks
  • bottled water which includes sparking water, spring water and purified/table water
  • functional drinks which can be carbonated or still and include sport, energy or elixir drinks
  • concentrates such as liquid and powder concentrates in ready to drink measure.
  • the hot drinks include, but are not limited to coffee, such as fresh (e.g., brewed), instant, combined coffee, liquid, ready-to-drink, soluble and dry coffee beverages, coffee beverage mixes and concentrates (syrups, pure, formulated, or in powder form; example of a “powder form” is a product comprising coffee, sweetener, and whitener all in powder form); tea, such as black, green, white, oolong, and flavored tea; and other hot drinks including flavor-, malt- or plant-based powders, granules, blocks or tablets mixed with milk or water.
  • coffee such as fresh (e.g., brewed), instant, combined coffee, liquid, ready-to-drink, soluble and dry coffee beverages, coffee beverage mixes and concentrates (syrups, pure, formulated, or in powder form; example of a “powder form” is a product comprising coffee, sweetener, and whitener all in powder form); tea, such as black, green, white, oolong
  • the Snack Food category generally refers to any food that can be a light informal meal including, but not limited to Sweet and savory snacks and snack bars.
  • snack food include, but are not limited to fruit snacks, chips/crisps, extruded snacks, tortilla/corn chips, popcorn, pretzels, nuts and other sweet and savory snacks.
  • snack bars include, but are not limited to granola/muesli bars, breakfast bars, energy bars, fruit bars and other snack bars.
  • the Baked Goods category generally refers to any edible product the process of preparing which involves exposure to heat or excessive sunlight.
  • baked goods include, but are not limited to bread, buns, cookies, muffins, cereal, toaster pastries, pastries, waffles, tortillas, biscuits, pies, bagels, tarts, quiches, cake, any baked foods, and any combination thereof.
  • the Ice Cream category generally refers to frozen dessert containing cream and sugar and flavoring.
  • ice cream include, but are not limited to: impulse ice cream; take-home ice cream; frozen yoghurt and artisanal ice cream; soy, oat, bean (e.g., red bean and mung bean), and rice-based ice creams.
  • the Confectionary category generally refers to edible product that is sweet to the taste.
  • Examples of confectionary include, but are not limited to candies, gelatins, chocolate confectionery, sugar confectionery, gum, and the likes and any combination products.
  • the Meal Replacement category generally refers to any food intended to replace the normal meals, particularly for people having health or fitness concerns. Examples of meal replacement include, but are not limited to slimming products and convalescence products.
  • the Ready Meal category generally refers to any food that can be served as meal without extensive preparation or processing.
  • the read meal includes products that have had recipe “skills” added to them by the manufacturer, resulting in a high degree of readiness, completion and convenience.
  • Examples of ready meal include, but are not limited to canned/preserved, frozen, dried, chilled ready meals; dinner mixes; frozen pizza; chilled pizza; and prepared salads.
  • the Pasta and Noodle category includes any pastas and/or noodles including, but not limited to canned, dried and chilled/fresh pasta; and plain, instant, chilled, frozen and snack noodles.
  • the Canned/Preserved Food category includes, but is not limited to canned/preserved meat and meat products, fish/seafood, vegetables, tomatoes, beans, fruit, ready meals, soup, pasta, and other canned/preserved foods.
  • the Frozen Processed Food category includes, but is not limited to frozen processed red meat, processed poultry, processed fish/seafood, processed vegetables, meat substitutes, processed potatoes, bakery products, desserts, ready meals, pizza, soup, noodles, and other frozen food.
  • the Dried Processed Food category includes, but is not limited to rice, dessert mixes, dried ready meals, dehydrated soup, instant soup, dried pasta, plain noodles, and instant noodles.
  • the Chill Processed Food category includes, but is not limited to chilled processed meats, processed fish/seafood products, lunch kits, fresh cut fruits, ready meals, pizza, prepared salads, soup, fresh pasta and noodles.
  • the Baby Food category includes, but is not limited to milk- or soybean-based formula; and prepared, dried and other baby food.
  • the Spreads category includes, but is not limited to jams and preserves, honey, chocolate spreads, nut based spreads, and yeast based spreads.
  • the Dairy Product category generally refers to edible product produced from mammal's milk.
  • dairy product include, but are not limited to drinking milk products, cheese, yoghurt and sour milk drinks, and other dairy products.
  • comestible compositions include one or more confectioneries, chocolate confectionery, tablets, countlines, bagged selflines/softlines, boxed assortments, standard boxed assortments, twist wrapped miniatures, seasonal chocolate, chocolate with toys, alfajores, other chocolate confectionery, mints, standard mints, power mints, boiled sweets, pastilles, gums, jellies and chews, toffees, caramels and nougat, medicated confectionery, lollipops, liquorice, other sugar confectionery, gum, chewing gum, sugarized gum, sugar free gum, functional gum, bubble gum, bread, packaged/industrial bread, unpackaged/artisanal bread, pastries, cakes, packaged/industrial cakes, unpackaged/artisanal cakes, cookies, chocolate coated biscuits, sandwich biscuits, filled biscuits, savory biscuits and crackers, bread substitutes, breakfast cereals, rte cereals, family breakfast cereals, flakes, muesi, other cereals
  • comestible compositions also include confectioneries, bakery products, ice creams, dairy products, sweet and savory snacks, snack bars, meal replacement products, ready meals, soups, pastas, noodles, canned foods, frozen foods, dried foods, chilled foods, oils and fats, baby foods, or spreads or a mixture thereof.
  • comestible compositions also include breakfast cereals, sweet beverages or solid or liquid concentrate compositions for preparing beverages.
  • comestible compositions also include coffee flavored food (e.g., coffee flavored ice cream).
  • a range format should be interpreted in a flexible manner to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range were explicitly recited.
  • a range of “about 0.1% to about 5%” or “about 0.1% to 5%” should be interpreted to include not just about 0.1% to about 5%, but also the individual values (e.g., 1%, 2%, 3%, and 4%) and the sub-ranges (e.g., 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the indicated range.
  • the steps can be carried out in any order without departing from the principles of the invention, except when a temporal or operational sequence is explicitly recited. Furthermore, specified steps can be carried out concurrently unless explicit claim language recites that they be carried out separately. For example, a claimed step of doing X and a claimed step of doing Y can be conducted simultaneously within a single operation, and the resulting process will fall within the literal scope of the claimed process.
  • substantially refers to a majority of, or mostly, as in at least about 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98%, 99%, 99.5%, 99.9%, 99.99%, or at least about 99.999% or more.
  • Samples were prepared via the design shown in Table 1, in weight to volume percentage.
  • An appropriate amount of steviol glycoside (SG) was weighed into a 10 mL glass vial and diluted with an appropriate volume of pH 4 citrate buffer, e.g., for 0.6% level, 27 mg was diluted into 4.5 mL of buffer. This was repeated for all conditions in Table 1.
  • Samples that were designed for pH 2.5 were then adjusted via phosphoric acid and pH meter to pH 2.5, dropwise. For these samples, the same lot of steviol glycoside stabilizing compound (SC) was used, which was purified from stevia leaves.
  • SC steviol glycoside stabilizing compound
  • Two different SG sources were used, RM80 (>80% Reb M on a dry weight basis) and RA95 (>95% Reb A on a dry weight basis).
  • long term storage chemical stability data stored at 4° C.; room temperature ( ⁇ 22° C.); at pH 4; and at pH 2.5>94% recovery of the SG after 48+ weeks of storage.
  • the long term storage chemical stability data is given in Table 2.
  • a value of NM denotes that no measurement was taken at that time.
  • Steviol glycoside stability compounds are effective to stabilize steviol glycoside over time.
  • Steviol glycoside stability compounds are effective to stabilize steviol glycoside over 48 weeks with greater than 94% recovery of the steviol glycoside at 4° C., at room temperature, at pH 4, and/or at pH 2.5.
  • Samples were prepared at 500 ppm (a use level that can be used in beverages) for storage at room temperature (RT, which is ⁇ 22° C.).
  • a pH 1.7 buffer (Oakton, part number 00654-01) was purchased from Fisher and used to dilute all samples.
  • the lot of SC material used in the study was derived from yerba mate.
  • Three total solutions were made for the study: one with no additives (500 ppm Reb M in pH 1.7 buffer), one with 500 ppm Reb M and 500 ppm SCs, and one negative control with 500 ppm Reb M and 500 ppm ascorbic acid (a common antioxidant).
  • Highly purified Reb M (>99%) was weighed directly into a 40 mL glass vial at an appropriate level, so the final concentration was 500 ppm, i.e., 20 mg into 40 mL. Next the additive (if present) was weighed directly in the same vial. Finally the total volume of pH 1.7 buffer was added and the solution was mixed to dissolve.
  • Table 5 shows the percent recovery data from pure Reb M (>99%) study in 5% phosphoric acid matrix (pH ⁇ 1) stored at 40° C.
  • Table 6 shows the percent recovery data from Reb M in RM80 product in 5% phosphoric acid matrix (pH ⁇ 1) stored at 40° C.
  • Table 7 shows data from a use level (e.g., 0.1% RM80) study in 0.1% phosphoric acid matrix at room temperature ( ⁇ 22° C.).
  • Table 8 is the statistical evaluation of the stability enhancement at each timepoint compared to the solution without stability enhancing compounds.
  • Tables 9 and 10 show the percent recovery data from Reb M (>99%) study in 5% phosphoric acid matrix (pH ⁇ 1) stored at 40° C., in the presence of Rosmarinic Acid and Cichoric Acid respectively.
  • the steviol glycoside stabilzing compounds are themselves subject to degradation over time.
  • the SCs can hydrolyze under acidic conditions to form caffeic acid.
  • the SCs can also oxidize over time when exposed to oxygen.
  • the SCs were also quantified in the same experiment as outlined in Table 11.
  • the SCs are much more resistant to acidic hydrolysis than the SGs, but the stability enhancement follows the same trend. At higher concentrations, the SGs and SCs both are more efficiently stabilized.
  • the present invention provides for the following embodiments, the numbering of which is not to be construed as designating levels of importance:
  • Embodiment 1 relates to a composition comprising:
  • Embodiment 2 relates to the composition of Embodiment 1, wherein the composition is an aqueous composition.
  • Embodiment 3 relates to the composition of Embodiments 1-2, wherein the amount of steviol glycoside stabilizing compound effective to reduce degradation of the steviol glycoside is an amount such that at least about 10 wt. % of an initial steviol glycoside remains when the stabilized steviol glycoside composition is subjected to storage for 7 days at 40° C. in 5% phosphoric acid.
  • Embodiment 4 relates to the composition of Embodiments 1-3, wherein the steviol glycoside comprises at least about 0.03 wt. % steviol glycoside.
  • Embodiment 5 relates to the composition of Embodiments 1-3, wherein the steviol glycoside comprises at least about 0.6 wt % steviol glycoside.
  • Embodiment 6 relates to the composition of Embodiments 1-5, wherein the composition comprises a 1:0.3 to 1:3 ratio by weight of steviol glycoside to steviol glycoside stabilizing compound.
  • Embodiment 7 relates to the composition of Embodiments 1-6, wherein the composition has a pH of less than about 4.
  • Embodiment 8 relates to the composition of Embodiments 1-6, wherein the composition has a pH of less than about 1.
  • Embodiment 9 relates to the composition of Embodiments 1-8, wherein the composition is stored at room temperature.
  • Embodiment 10 relates to the composition of Embodiments 1-8, wherein the composition is stored at about 4° C.
  • Embodiment 11 relates to the composition of Embodiments 1-10, wherein the steviol glycoside is Rebaudioside A or Rebaudioside M.
  • Embodiment 12 relates to a beverage concentrate product comprising the composition of Embodiments 1-11, wherein the steviol glycoside comprises between about 1,800 ppm and about 10,000 ppm steviol glycoside.
  • Embodiment 13 relates to a liquid water enhancer product comprising the composition of Embodiments 1-11, wherein the steviol glycoside comprises between about 1.5 wt. % and about 3.5 wt. %. steviol glycoside.
  • Embodiment 14 relates to a liquid sweetener comprising the composition of Embodiments 1-11, wherein, the steviol glycoside comprises between about 1.0 wt. % and about 10 wt. % steviol glycoside.

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US16/374,388 Active US11701400B2 (en) 2017-10-06 2019-04-03 Steviol glycoside compositions with reduced surface tension
US16/374,422 Abandoned US20190223483A1 (en) 2017-10-06 2019-04-03 Sensory modifier compounds
US16/374,894 Active US11351214B2 (en) 2017-10-06 2019-04-04 Methods for making yerba mate extract composition
US17/807,798 Pending US20220323528A1 (en) 2017-10-06 2022-06-20 Steviol glycoside solubility enhancers
US18/153,484 Pending US20230364171A1 (en) 2017-10-06 2023-01-12 Sensory modifier compounds
US18/328,066 Pending US20240050506A1 (en) 2017-10-06 2023-06-02 Steviol glycoside compositions with reduced surface tension
US18/335,968 Pending US20240082334A1 (en) 2017-10-06 2023-06-15 Stabilized steviol glycoside compositions and uses thereof
US18/335,946 Pending US20240082333A1 (en) 2017-10-06 2023-06-15 Readily dissolvable steviol glycoside compositions

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