WO2015042344A1 - Glycoside de stéviol glucosylé utile en tant que modificateur d'arôme - Google Patents

Glycoside de stéviol glucosylé utile en tant que modificateur d'arôme Download PDF

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Publication number
WO2015042344A1
WO2015042344A1 PCT/US2014/056451 US2014056451W WO2015042344A1 WO 2015042344 A1 WO2015042344 A1 WO 2015042344A1 US 2014056451 W US2014056451 W US 2014056451W WO 2015042344 A1 WO2015042344 A1 WO 2015042344A1
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Prior art keywords
taste
food
steviol glycosides
flavor
modifying composition
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PCT/US2014/056451
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English (en)
Inventor
Avetik Markosyan
Original Assignee
Purecircle Usa Inc.
Purkayastha, Siddhartha
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Filing date
Publication date
Priority claimed from US14/031,290 external-priority patent/US9107436B2/en
Application filed by Purecircle Usa Inc., Purkayastha, Siddhartha filed Critical Purecircle Usa Inc.
Priority to MX2016003540A priority Critical patent/MX2016003540A/es
Priority to CN202211629713.5A priority patent/CN115736229A/zh
Priority to CN201480057789.2A priority patent/CN105899087A/zh
Priority to EP14845720.3A priority patent/EP3046427A4/fr
Priority to BR112016006155A priority patent/BR112016006155A2/pt
Publication of WO2015042344A1 publication Critical patent/WO2015042344A1/fr

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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
    • 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
    • A23L23/00—Soups; Sauces; Preparation or treatment 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
    • 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
    • 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
    • A23L27/86—Addition of bitterness inhibitors
    • 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
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A23L29/35—Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches
    • 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
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A23L29/37—Sugar alcohols
    • 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

Definitions

  • the present invention relates generally to glucosylated steviol glycoside compositions and methods for making and using them as a taste improver and flavor modifier in various food and beverage products.
  • the invention also relates to a combination of selective combination of glucosylated steviol glycoside components and steviol glycoside molecules from Stevia rebaudiana Bertoni plant extract to make the optimum sweetness profile and flavor modification in food and beverage applications.
  • the invention also relates to the combination of the steviol glycoside derived molecules and maltodextrin derived from starch to provide the mouthfeel and flavor modification characteristics of Glucosylated steviol Glycosides in reduced or no sugar added food and beverage products.
  • the extract of Stevia rebaudiana plant contains a mixture of different sweet diterpene glycosides, which have a single base - steviol and differ by the presence of carbohydrate residues at positions CI 3 and CI 9. These glycosides accumulate in Stevia leaves and compose approximately 10% - 20% of the total dry weight.
  • the major steviol glycoside molecules present in the stevia extract are stevioside, Rebaudioside A, Rebaudioside C, Dulcoside A, Rebaudioside D, Rebaudioside B and Rebaudioside F.
  • Other minor components are Rebaudioside E, Steviolbioside and Rubusoside.
  • Recent research found additional steviol glycoside molecules (Ohta et al, 2010; Prakash et al, 2013): Rebaudioside G, H, I, J, K, L, M, N, and O.
  • steviol glycoside molecules have high intensity of sweetness, ranging between 50 to 400 times sweeter than sugar. However, apart from the high level of sweetness, they have also intrinsic properties of bitter and licorice taste and undesirable aftertaste. Some undesirable taste characteristics of glycosides can be as a result of contamination of other substances present in stevia extract.
  • One of the main ways to improve the taste quality is the enzymatic glycosylation of mixture of semi-purified steviol glycosides. It is known that the undesired taste attributes can be substantially reduced or eliminated by the reaction of intermolecular transglycosylation of various enzymes, upon which the attachment of new carbohydrates at positions CI 3 and C19 of steviol glycosides takes place (FIG. 1).
  • a process is developed to make a mixture of glucosylated steviol glycosides with small amount of other steviol glycosides and maltodextrin.
  • the process involved precise control of pH, temperature, enzyme source and activity, quality of stevia extract, glucose- donor (amount and source) and time to achieve blends of different ratios of glucosylated steviol glycosides, steviol glycoside molecules, and maltodextrin.
  • the present invention is directed to a taste and flavor profile improving composition.
  • the composition includes glucosylated steviol glycosides, steviol glycosides and maltodextrin.
  • the glucosylated steviol glycosides may include a plurality of glucose units.
  • the glucosylated steviol glycosides may include three, four, five, or more than five glucose units (FIG. 1).
  • the invention in part, pertains to an ingredient containing glucosylated steviol glycoside (GSG) of different degree of glycosylation to steviol glycoside molecules derived from stevia extract of Stevia Rebaudiana Bertoni plant. Also, this invention, in part, pertains to specific blends of GSG components with varying degree of glycosylation. The invention, in part, pertains to an ingredient comprising steviol glycosides of Stevia Rebaudiana Bertoni plant.
  • GSG glucosylated steviol glycoside
  • the steviol glycosides are selected from the group consisting of stevioside, Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, dulcoside A, steviolbioside, rubusoside, as well as other steviol glycosides found in Stevia Rebaudiana Bertoni plant and mixtures thereof.
  • Rebaudioside is commonly expressed as Reb or reb also.
  • the invention in part, pertains to specific blends of different steviol glycosides (SG) and glucosylated steviol glycosides (GSG) for producing an ingredient containing Rebaudioside D, Rebaudioside A, Rebaudioside B, stevioside, Rebaudioside C, and other steviol glycosides found in Stevia Rebaudiana Bertoni plant and mixtures thereof.
  • SG steviol glycoside
  • GSG glucosylated steviol glycosides
  • the invention in part, pertains to specific blends of different GSG, SG components and residual maltodextrins derived from starch, which is used as glucose-donor.
  • the source of starch such as, but not limited to, tapioca, maize, wheat, potato, barley, sweet potato and other commercial and non-commercial carbohydrate source.
  • the present invention is also directed to a process to make the different blends of GSG and SG from stevia extracts of different amount and mixture of steviol glycosides.
  • the process conditions, type and ratio of stevia extract and starch used are crucial for making the composition, which will yield different amount and composition of GSG, SG and maltodextrin.
  • the invention in part, pertains to a process of manufacturing the specific blend of GSG components, selected steviol glycosides (SG) and maltodextrin.
  • the processing steps include: i) Tapioca starch is dissolved in RO water and liquefied by CGTase under controlled processing conditions
  • CGTase enzyme added to mixture and incubated at 60°C for a desired length of reaction time to glycosylate steviol glycosides with glucose molecules derived from
  • reaction mixture is heated to 100°C for 15min to inactivate the CGTase, which is then removed by treating with activated carbon.
  • the present invention is also directed to a food or beverage product having an intense taste and flavor profile, wherein the food or beverage product includes a taste and flavor modifying composition comprising glucosylated steviol glycosides, selected steviol glycosides and maltodextrins.
  • a taste and flavor modifying composition comprising glucosylated steviol glycosides, selected steviol glycosides and maltodextrins.
  • the taste and flavor profile of a food or beverage product including a taste and flavor modifying composition may be more intense than a comparative taste and flavor profile of a comparative food or beverage product which does not include the taste and flavor modifying composition.
  • the mouthfeel of a food or beverage product including the taste and flavor modifying composition wherein the taste and flavor modifying composition includes glucosylated steviol glycosides, selected steviol glycosides and maltodextrins, may be improved in relation to a mouthfeel of a comparative food or beverage product which does not include the taste and flavor modifying composition.
  • the present invention is further directed to a method of enhancing the taste and flavor intensity of a food or beverage product, including the step of adding a taste and flavor modifying composition to the food or beverage product, wherein the taste and flavor modifying composition includes the blend of glucosylated steviol glycosides, selected steviol glycosides and maltodextrins.
  • compositions can be used as flavor modifier in various food and beverage products.
  • beverage products include carbonated and still beverages, flavored water, juice-based beverages, energy drinks and powder soft drinks.
  • Non-limiting examples of food include dairy products (yogurt, yogurt drinks, flavored milk, frozen dairy desserts including ice cream), baked goods and baking mixes (bread, biscuits, cookies, muffins, rolls, and baking mixes), sauces and gravies, jams and jellies, gelatins, puddings and fillings, soy sauce and other soy based products, breakfast cereals, condiments and relishes, confections and frostings, processed fruits and vegetables, sugar substitutes and confectionery products including chewing gums.
  • FIG. 1 illustrates the glycosylation steps for making different glucosylated steviol glycoside molecules from stevioside.
  • FIG 1A shows the single glycosylation of stevioside.
  • FIG IB shows multiple glycosylation.
  • FIG. 2 is a graph of the sweetness potency, or sucrose equivalent value (SEV), of steviol glycosides and Glucosylated steviol glycosides at a 5% sugar sweetness level.
  • FIG. 3 shows the impact of degree of glucosylation on the perception of sweetness and flavor profile of a typical beverage application.
  • FIG. 4 shows the impact of GSG components on the perception of sweetness and bitterness in beverage application.
  • GSG glucosylated steviol glycosides
  • flavor modification is affected by the composition of the blend of GSG, steviol glycosides (SG) and maltodextrin.
  • the size and amount of GSG molecules and the type and amount of residual steviol glycoside (SG) contribute different degree of flavor modification. Therefore, while sweetness decreases with glycosylation, flavor modification increases.
  • the flavor modification may include an increase (enhance) in certain flavor note and/or reduction (suppress) of certain other flavor notes.
  • the blend of GSG and SG provides a certain amount of sweetness, but the present invention shows that such blends modify the flavor and sweetness profile in a wide range of food and beverage applications.
  • the present invention pertains to a process where the blend of specific type and content of GSG and SG made from Tapioca starch and stevia extract, which contains total steviol glycoside content from 50 to 100%, with predominant steviol glycoside molecules of stevioside, Reb A, Reb B, Reb C and Reb D.
  • the specific type of GSG means GSG molecules derived from steviol glycosides with different degree of glycosylation, resulting number of additional glucose units added to base steviol glycoside molecules.
  • the type of residual steviol glycosides means the unreacted residual steviol glycosides, which may be stevioside, Reb A, Reb B, Reb C, Reb D and other steviol glycoside molecules present in the stevia extract.
  • the present invention also pertains to the specific composition of blends, where the type and amount of different GSG molecules and SG molecules contribute different degree of taste modification in the food and beverage applications.
  • compositions can be used as flavor and sweetness profile modifier in various food and beverage products.
  • food and beverage products include carbonated soft drinks, ready to drink beverages, energy drinks, isotonic drinks, low-calorie drinks, zero- calorie drinks, sports drinks, teas, fruit and vegetable juices, juice drinks, dairy drinks, yoghurt drinks, alcohol beverages, powdered beverages, bakery products, cookies, biscuits, baking mixes, cereals, confectioneries, candies, toffees, chewing gum, dairy products, flavored milk, yoghurts, flavored yoghurts, cultured milk, soy sauce and other soy base products, salad dressings, mayonnaise, vinegar, frozen-desserts, meat products, fish-meat products, bottled and canned foods, tabletop sweeteners, fruits and vegetables.
  • compositions can be used in drug or pharmaceutical preparations and cosmetics, including but not limited to toothpaste, mouthwash, cough syrup, chewable tablets, lozenges, vitamin preparations, and the like.
  • compositions can be used "as-is" or in combination with other sweeteners, sugar alcohols, flavors and food ingredients in food, beverage, pharmaceutical and cosmetics applications.
  • sweeteners sugar alcohols
  • flavors and food ingredients in food, beverage, pharmaceutical and cosmetics applications.
  • the following examples illustrate various embodiments of the invention. It will be understood that the invention is not limited to the materials, proportions, conditions and procedures set forth in the examples, which are only illustrative.
  • FIG. 1A illustrates the single glycosylation (Gl) of a stevioside molecule. This process can yield multiple glycosylation (G2, G3, etc.) of different steviol glycosides (mainly stevioside and Rebaudioside A) present in stevia extract as shown in FIG IB.
  • CGTase cyclomaltodextrin glucanotransferase
  • reaction mixture is heated to 100°C for 15min to inactivate the CGTase, which is then removed by treating with activated carbon.
  • the resulting solution of GSG, residual steviol glycosides and maltodextrin concentrated by means of conventional vacuum evaporator and dried.
  • Test Design 2- AFC, Balanced, randomized within pair. Blind
  • steviol glycosides SG
  • GSG glucosylated steviol glycosides
  • Table 4 a series of stevia derived samples were selected as shown in Table 4.
  • aqueous solutions of sugar, stevioside, Rebaudioside A (Reb A), Rebaudioside D (Reb D), GSG- S (contains mainly smaller GSGs with 1 or 2 glucose units added to SG), GSG-M and GSG-L at various concentrations were prepared using bottled water. Samples were evaluated by the judges at room temperature (70-72°F). Table 4
  • the judges were 1 1 panelists that have been previously qualified for their taste acuity and trained in the use of a sweetness intensity rating scale. The evaluations were done in duplicate using the same panelists so that a total of 22 values were generated for each average data point. Prior to the conduct of the study, judges were trained with sugar solutions and the use of the ballot.
  • Samples were given to the judges sequentially and coded with triple digit numbers. The order of sample presentation was randomized to avoid order of presentation bias. A rest period of five minutes was provided between samples. Water and unsalted crackers were provided in order to cleanse the palate.
  • Results were statistically analyzed to generate a standard error value for each solution as well as a confidence level at a 95% level.
  • sweetness potency at 5% sucrose equivalent
  • concentration of each stevia ingredient was estimated as shown in FIG. 2.
  • the sweetness equivalence of stevia ingredient at 5% sucrose-level is commercially relevant. This figure shows the effect of glycosylation on the SEV of steviol glycosides. The sweetness increases from stevioside to Reb A and then starts decreasing as more glucose units are added to the base molecules (stevioside and Reb A).
  • a mango-passion fruit flavored water formula was developed to evaluate the effect of different stevia ingredients on the sweetness and flavor profile of the beverage.
  • a total of 9-10 panel members participated in this sensory test, where they assigned relative values to sweetness, onset of sweetness, mango fruit flavor, passion fruit flavor, acidity, overall taste, etc.
  • Table 5 shows the no-sugar added beverage formula that used mainly Reb A, Reb D, GSG-S, or GSG-L.
  • the amount of each ingredient (Reb A: 150 ppm; Reb D: 165 ppm; GSG-S: 190 ppm; and GSG-L: 300 ppm) was selected to have around 50 ppm of steviol in each formula.
  • FIG. 3 shows the modification of flavor and sweetness profiles caused by glycosylation.
  • the sweetness intensity decreased and sweet onset delayed with glycosylation.
  • Mango flavor was enhanced and the passion fruit flavor was suppressed with glycosylation.
  • sweetness intensity can impact the perception of the overall taste, flavor and sweetness profile
  • main objective was to determine the contribution of different flavoring blends on different taste attributes by adding amount of each blend (Table 6) that contributes 1 % sugar equivalent sweetness.
  • the taste attributes of sweetness intensity, bitterness intensity and overall liking were used to rank flavors from most to least desirables.
  • the sensory evaluation was conducted by 20 members consumer panel recruited in Chicago area. Each person was trained on 15 point sweetness and bitterness intensity scale. For each sample, sweetness and bitterness intensity was evaluated on a 15 point scale. Sweet and bitter aftertaste was assessed on a 5 point scale. Overall liking was evaluated on a 9 point hedonic scale. Each participant tasted 5 samples during one session. Unsalted cracker and water were used to cleanse palate in addition to 2 minute wait between samples. In forced ranking, the consumer panels found that GSG-S contributed the highest perception of sweetness, which decreased with larger molecules of GSG (GSG M & GSG-L) as shown in FIG. 4. The perception of bitterness was least for GSG-S, highest for GSG-M.
  • the GSG-L and combination of GSG had lower bitterness than GSG-M.
  • GSG-S was directionally better in delivering sweetness intensity without contributing significant bitterness.
  • the statistical analysis of results indicates that the perception of lower bitterness had the highest impact on the overall liking of a sample.
  • the sweet and bitter aftertaste had lower impact than bitter perception on the overall liking of a sample.
  • FIG. 4 shows the relative perception of sweet and bitter taste.
  • GSG-M is made from a stevia extract with high Reb A content and it contains the predominantly Reb A as the residual SG in the blend.
  • GSG-S is made from a stevia extract with high stevioside content and thus it contains the predominantly stevioside as the residual SG in the blend.
  • Each participant was presented Set 1 first, followed by Set 2.
  • the order of samples in each set was randomized and evaluated for sweetness, bitterness intensity and aftertaste and overall liking.
  • each panel member was asked for forced preference for liking in each set.
  • the bitterness and aftertaste was similar to the control. No significant differences were seen in overall liking.
  • the panel members preferred GSG-SW (48% ranked 1 st ) over control (28% ranked 1 st ) and GSG-M (24% ranked 1 st ).
  • the bitterness for GSG-SW was directionally lower than control (p 0.6). No significant differences were seen in aftertaste and overall liking.

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Abstract

La présente invention concerne une composition modifiant le profil de goût et de saveur. La composition comprend un mélange de glycosides de stéviol glucosylés et de glycosides de stéviol résiduels qui peuvent modifier l'intensité d'un goût et/ou un arôme dans un produit alimentaire ou une boisson.
PCT/US2014/056451 2013-09-19 2014-09-19 Glycoside de stéviol glucosylé utile en tant que modificateur d'arôme WO2015042344A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
MX2016003540A MX2016003540A (es) 2013-09-19 2014-09-19 Glicosido de esteviol glucosilado como un modificador de sabor.
CN202211629713.5A CN115736229A (zh) 2013-09-19 2014-09-19 作为风味改良剂的糖基化甜菊醇糖苷
CN201480057789.2A CN105899087A (zh) 2013-09-19 2014-09-19 作为风味改良剂的糖基化甜菊醇糖苷
EP14845720.3A EP3046427A4 (fr) 2013-09-19 2014-09-19 Glycoside de stéviol glucosylé utile en tant que modificateur d'arôme
BR112016006155A BR112016006155A2 (pt) 2013-09-19 2014-09-19 glicosídeo de esteviol glicosilado como um modificador de sabor

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US14/031,290 2013-09-19
US14/031,290 US9107436B2 (en) 2011-02-17 2013-09-19 Glucosylated steviol glycoside as a flavor modifier

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WO2015042344A1 true WO2015042344A1 (fr) 2015-03-26

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WO2017011291A1 (fr) * 2015-07-10 2017-01-19 Sweet Green Fields USA LLC Compositions de dérivés multiglycosylés de stéviol et composants de stévia
WO2017089444A1 (fr) * 2015-11-24 2017-06-01 Firmenich Sa Glycosides de terpène glucosylés
WO2019162509A1 (fr) * 2018-02-26 2019-08-29 Firmenich Sa Composition comprenant des glycosides terpéniques glucosylés, des glycosides terpéniques et de la cyclodextrine
WO2020126688A1 (fr) * 2018-12-19 2020-06-25 Firmenich Sa Formulations d'édulcorant et utilisations

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EP3644757A1 (fr) * 2017-06-26 2020-05-06 Firmenich SA Compositions aromatisantes
CN108103127A (zh) * 2017-12-13 2018-06-01 桂林莱茵生物科技股份有限公司 一种工业化快速生产制备葡萄糖基甜菊糖苷混合物的方法
CN109293718A (zh) * 2018-10-08 2019-02-01 山东奥晶生物科技有限公司 一种甜菊糖酶改质甜菊糖甙的制备方法
WO2020147080A1 (fr) * 2019-01-17 2020-07-23 Beijing Gingko-Group Biological Technology Co., Ltd Procédé pour la transglucosylation de glycosides de stéviol et de ses compositions de glycosides de stéviol
CN110907604A (zh) * 2019-12-06 2020-03-24 浙江华康药业股份有限公司 一种用于改善糖醇类物质感官属性的方法及其应用

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CN111601516A (zh) * 2018-02-26 2020-08-28 弗门尼舍有限公司 包含糖基化萜烯糖苷、萜烯糖苷和环糊精的组合物
JP2021514607A (ja) * 2018-02-26 2021-06-17 フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ グルコシル化テルペングリコシド、テルペングリコシドおよびシクロデキストリンを含む組成物
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MX2016003540A (es) 2016-12-08
CN105899087A (zh) 2016-08-24
EP3046427A1 (fr) 2016-07-27
EP3046427A4 (fr) 2017-11-29
CN115736229A (zh) 2023-03-07

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