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WO2006072921A2 - Composition edulcorante a base d'extrait de stevia et de maltol et procedes de preparation correspondants - Google Patents

Composition edulcorante a base d'extrait de stevia et de maltol et procedes de preparation correspondants Download PDF

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Publication number
WO2006072921A2
WO2006072921A2 PCT/IB2006/050061 IB2006050061W WO2006072921A2 WO 2006072921 A2 WO2006072921 A2 WO 2006072921A2 IB 2006050061 W IB2006050061 W IB 2006050061W WO 2006072921 A2 WO2006072921 A2 WO 2006072921A2
Authority
WO
WIPO (PCT)
Prior art keywords
sweetener composition
stevia extract
maltol
inert excipients
stevia
Prior art date
Application number
PCT/IB2006/050061
Other languages
English (en)
Other versions
WO2006072921A3 (fr
Inventor
Chandra Kant Katihyar
Arvind Padiyar
Avinash Narwaria
Rahul Singh
Roopak Kumar
Anil Kanaujia
Yogita Rani
Original Assignee
Ranbaxy Laboratories Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ranbaxy Laboratories Limited filed Critical Ranbaxy Laboratories Limited
Publication of WO2006072921A2 publication Critical patent/WO2006072921A2/fr
Publication of WO2006072921A3 publication Critical patent/WO2006072921A3/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/84—Flavour masking or reducing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • 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

Definitions

  • the technical field of the present invention relates to sweetener compositions of stevia extract and maltol, and processes for their preparation.
  • Stevia rebaudiana Bertoni is a perennial shrub of the Asteraceae (Compositae) family native to Paraguay and Brazil. Leaves of Stevia rebaudiana are well known for their sweetening properties.
  • the sweet compounds are mainly the diterpene glycosides based on the kaurene skeleton that represent about 14% constituent of dried leaves.
  • the sweet diterpene glycosides include stevioside, steviolbioside, rebaudioside A, B, C, D and E, and dulcoside A and B. Steviol is the aglycone moiety in all these glycosides.
  • the major sweet components are stevioside, which has a molecular weight of 804.9 and a melting point between 196-198°C, and rebaudioside A, which has a molecular weight of 967.0 and a melting point between 242-244°C.
  • Stevia rebaudiana extract is widely accepted as a food for use as dietary supplement and also as a natural sweetener, particularly in food and beverages.
  • the major component stevioside is heat and pH stable. It is approximately three hundred times sweeter than sucrose, and has zero calorific value. It has been used for more than twenty years in Japan and Brazil with no adverse effects reported so far.
  • the major component stevioside apart from its high level of sweetness, also has an inherent property of an unpleasant and undesirable menthol like bitter after taste. The unpleasant taste is also contributed by volatile aromatic or essential oils, tannins and flavanoids present in Stevia leaf extract (Stevia extract).
  • the first method involves organic solvent extraction using solvents such as alcohol. This method has the disadvantage of contributing to high amounts of residual solvents.
  • the second method involves attaching stevioside to resins by washing the resin with acid and alkaline solution. These methods produce low yields, hence are not cost effective. Moreover, these methods do not considerably improve the taste.
  • the third method involves adding moieties such as amino acid or glycosyl groups to the stevioside structure. However, since large quantities of amino acid and glycosyl are required in the production process, it results in increasing calorific value, and destroying the low calorie characteristic of stevioside.
  • the fourth method involves combining stevioside with other excipients which mask the bitter after taste of stevioside.
  • Japanese patent application 57150358 discloses combinations with polysaccharides such as puUulan, dextran, locust bean gum or b- cyclodextrin.
  • Japanese patent 05007973 discloses a combination with L-sorbose.
  • Japanese patent 05000981 discloses combinations with organic acid salts such as tartarate or citrate.
  • maltol One of the substances which is a major constituent of flavoring and taste masking compositions is maltol. However, a combination of stevia extract with maltol is not known in the prior art.
  • a sweetener composition comprising stevia extract and maltol.
  • Embodiments of the sweetener composition may include one or more of the following features.
  • the stevia extract may be or include stevioside.
  • the stevia extract may be made up of at least 30% w/w stevioside or of at least 50% w/w stevioside.
  • the stevia extract may further include rebaudioside A.
  • the stevia extract may include at least 10% w/w rebaudioside A or at least 20% w/w rebaudioside A.
  • the stevia extract may make up from about 5% w/w to about 50% w/w of the sweetener composition or from about 15% w/w to about 25% w/w of the sweetener composition.
  • the sweetener composition may be one or more of a tablet, granule, powder, and sachet.
  • the sweetener may further include one or more inert excipients.
  • the inert excipient may be selected from one or more of disintegrants/superdisintegrants, binders, fillers, suspending agents, surfactants, colors, and lubricants/glidants.
  • the sweetener composition may further include an active pharmaceutical ingredient.
  • a process for the preparation of a sweetener composition of stevia extract includes the steps of (a) blending stevia extract, maltol, and one or more inert excipients; and (b) processing in to a sweetener composition.
  • Embodiments of the process may include one or more of the following features.
  • the blend of stevia extract, maltol, and one or more inert excipients of step a maybe granulated.
  • the granulation may be a dry or wet granulation technique.
  • the blend of stevia extract, maltol, and one or more inert excipients of step a may be processed into spheroids by an extrusion-spheronization technique.
  • composition that includes an active pharmaceutical ingredient, stevia extract, and maltol.
  • Embodiments of the pharmaceutical composition may include one or more of the features described herein.
  • a sweetener composition comprising stevia extract andmaltol.
  • a sweetener composition comprising stevia extract and maltol wherein the stevia extract comprises at least 30% w/w stevioside.
  • a process for the preparation of a sweetener composition of stevia extract wherein the process comprises the steps of blending stevia extract, maltol, and one or more inert excipients; and processing into a sweetener composition.
  • the blend of stevia extract and maltol may also be granulated or processed into spheroids.
  • a method of masking the bitter after taste of stevia extract with maltol is provided.
  • the 'sweetener composition' as used herein includes tablets, granules, powder, sachets, and the like.
  • the present invention provides a simple and cost effective method of improving the bitter after taste of natural sweetener stevia by combining it with maltol as a flavoring agent. This has been confirmed from a panel study conducted among more than three hundred users.
  • the sweetener compositions may be prepared using conventional technologies in a minimum number of processing steps.
  • the term 'Stevia extract' as used herein refers to aqueous extract obtained from leaves of Stevia rebaudiana. It is a white, free flowing, fluffy granular powder having extremely sweet taste, and comprising at least 30% w/w stevioside and at least 10% w/ w rebaudioside A, in particular at least 50% w/w stevioside and at least 20% w/w re- baudioside A.
  • the amount of stevia extract may vary from about 5% w/w to about 50% w/w of the sweetener composition; in particular, it may vary from about 15% w/w to about 25% w/w.
  • Maltol (Larixinic acid) is a white, crystalline compound obtained from larch bark, pine needles, chicory, and roasted malt. Maltol is soluble in water and glycerine; slightly soluble in alcohol, chloroform; and has a melting point of 161 °C. Maltol and its derivatives have a caramel like odor and are used as versatile flavor enhancers and modifiers (sweet, caramel, fruity, strawberry) in foods, wines, and perfumes. Commercially, maltol is available under various trade names such as Veltol and Pyromaltol.
  • Maltol is also an important constituent of many flavors approved by FEMA/GRAS for oral use, for example Contramarum Forte (Flavour 225023) commercialized by Symrise.
  • Contramarum Forte Flavour comprises maltodextrin, gum arabic, and artificial and natural identical ingredients such as menthyl esters and food esters.
  • the bitter after taste is masked to acceptable limits. Further, maltol is required in very small quantities.
  • sweetener compositions may comprise stevia extract, maltol, and one or more inert excipients.
  • the term 'inert excipient' as used herein includes all physiologically inert excipients used in the art for preparation of sweetener compositions. Examples include dis- integrants/superdisintegrants, binders, fillers, suspending agents, surfactants, lubricants/glidants, colors, and the like.
  • disintegrants/superdisintegrants include starch, cellulose derivatives, natural and synthetic gums, sodium starch glycolate, croscarmellose sodium, crospovidone, and low-substituted hydroxypropylcellulose. Extremely fast disintegration may be achieved by using superdisntegrants in the sweetener composition.
  • binders include starch; gelatin; sugars such as molasses, lactose, glucose, dextrose and sucrose; natural and synthetic gums such as acacia, sodium alginate, carboxymethyl cellulose, methylcellulose, polyvinyl pyrrolidone and veegum.
  • fillers include calcium carbonate, calcium phosphate-dibasic, calcium phosphate-tribasic, calcium sulfate, microcrystalline cellulose, powdered cellulose, dextrates, dextrins, fructose, kaolin, lactitol, lactose, mannitol, sorbitol, starch, sucrose, sugar compressible, and sugar confectioners.
  • micro- crystalline cellulose a polysaccharide, may be used.
  • suspending agents include microcrystalline cellulose, sodium carboxy methylcellulose, colloidal anhydrous silica, mannitol, povidone, sodium starch glycolate, and veegum.
  • surfactants include both non-ionic and ionic (cationic, anionic and zwitterionic) surfactants suitable for use in sweetener compositions. These include polyethoxylated fatty acids and their derivatives, for example polyethylene glycol 400 distearate, polyethylene glycol - 20 dioleate, polyethylene glycol 4 -150 mono dilaurate, polyethylene glycol -20 glyceryl stearate; alcohol - oil transesterification products, for example polyethylene glycol - 6 corn oil; polyglycerized fatty acids, for example polyglyceryl - 6 pentaoleate; propylene glycol fatty acid esters, for example propylene glycol monocaprylate; mono and diglycerides for example glycerylri- cinoleate; sterol and sterol derivatives; sorbitan fatty acid esters and their derivatives, for example polyethylene glycol - 20 sorbitanmonooleate, sorbitan
  • lubricants/glidants include colloidal anhydrous silica, stearic acid, magnesium stearate, calcium stearate, zinc stearate, sodium stearyl fumarate, talc, hydrogenated castor oil, sucrose esters of fatty acid, microcrystalline wax, yellow beeswax, and white beeswax.
  • colors and colorants include any approved color for oral use.
  • the sweetener composition may be prepared by a process comprising the steps of blending stevia extract and maltol with or without one or more inert excipients; wet granulating the blend with a granulating fluid or solution/ dispersion of one or more inert excipients in the granulating fluid; drying and sizing the granules; blending with one or more inert excipients; and compressing into tablets or filling into sachets.
  • the sweetener composition may be prepared by a process comprising the steps of blending stevia extract and maltol with or without one or more inert excipients; dry granulating the blend by roller compaction or slugging; sizing the granules; blending with one or more inert excipients; and compressing into tablets or filling into sachets.
  • the sweetener composition may be prepared by a process comprising the steps of blending stevia extract and maltol with or without one or more inert excipients; and compressing into tablets filling into sachets.
  • the sweetener composition may be prepared by a process comprising the steps of blending stevia extract and maltol with or without one or more inert excipients; forming a wet mass using a granulating fluid or solution/dispersion of inert excipients in the granulating fluid; passing the wet mass through an extruder equipped with a screen; spheronizing the extrudate in a spheronizer; drying and sizing the spheroids ;blending with one or more inert excipients; and compressing into tablets or filling into sachets.
  • Sweetener tablets prepared according to the embodiments above showed a hardness of about 1.5-2.0 kg and a disintegration time of less than about three minutes, in particular less than about one minute.
  • Stevia Extract 90% is an extract of Stevia rebaudiana leaves [44] Procedure: [45]
  • Stevia extract and lactose anhydrous were individually sieved through a # 30 sieve.
  • step 3 The sieved croscarmellose sodium, flavour, silicon dioxide and stearic acid of step 1 were blended in a suitable mixer followed by blending with a part of the sieved lactose anhydrous powder of step 2.
  • step 4 The sieved stevia extract of step 2 was then added to the blend of step 3 and mixed for about 5-10 minutes, followed by blending with the remaining parts of lactose anhydrous for about 10-15 minutes.
  • step 4 The blend of step 4 was compressed into 100 mg tablets using appropriate tooling.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Alternative & Traditional Medicine (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
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Abstract

Cette invention concerne les compositions édulcorantes à base d'extrait de stevia et de maltol; ainsi que des procédés permettant de les préparer.
PCT/IB2006/050061 2005-01-07 2006-01-06 Composition edulcorante a base d'extrait de stevia et de maltol et procedes de preparation correspondants WO2006072921A2 (fr)

Applications Claiming Priority (2)

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IN42DE2005 2005-01-07
IN42/DEL/2005 2005-01-07

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WO2006072921A2 true WO2006072921A2 (fr) 2006-07-13
WO2006072921A3 WO2006072921A3 (fr) 2006-11-02

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Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008147723A1 (fr) * 2007-05-22 2008-12-04 The Coca-Cola Company Systèmes d'administration pour compositions édulcorantes naturelles très puissantes, procédés de préparation et utilisations
WO2011144831A1 (fr) * 2010-05-21 2011-11-24 Sine Sileo Agent édulcorant contenant un extrait de stévia rebaudiana bertoni
EP2482676A2 (fr) * 2009-06-16 2012-08-08 Zhejiang Green World Bio-Tech Engineering Co., Ltd. Procede pour rebaudioside d
CN103053995A (zh) * 2007-11-12 2013-04-24 三荣源有限公司 改善甜叶菊提取物甜味的方法
JP2013540795A (ja) * 2010-10-28 2013-11-07 ヘキサル・アクチェンゲゼルシャフト 苦味のある薬物のための経口用医薬フィルム製剤
WO2014000755A1 (fr) * 2012-06-27 2014-01-03 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Compositions de masquage du goût, compositions d'édulcorant et compositions de produit consommable les contenant
US8937168B2 (en) 2007-01-22 2015-01-20 Cargill, Incorporated Method of producing purified rebaudioside A compositions using solvent/antisolvent crystallization
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US9314048B2 (en) 2007-03-14 2016-04-19 The Concentrate Manufacturing Company Of Ireland Beverage products with non-nutritive sweetener and bitterant
US9402411B2 (en) 2011-01-28 2016-08-02 Tate & Lyle Ingredients Americas Llc Stevia blends containing rebaudioside B
EP2124648B1 (fr) 2007-03-14 2017-01-04 The Concentrate Manufacturing Company of Ireland Boisson ayant des édulcorants naturels avec un ou plusieurs composants de stévia et une source de baie
US9578895B2 (en) 2010-08-23 2017-02-28 Epc (Beijing) Natural Products Co., Ltd. Rebaudioside A and stevioside compositions
US9609887B2 (en) 2012-08-01 2017-04-04 Tate & Lyle Ingredients Americas Llc Sweetener compositions containing monk fruit extract and rebaudiosides A and B
US9795156B2 (en) 2011-03-17 2017-10-24 E.P.C (Beijing) Plant Pharmaceutical Technology Co., Ltd Rebaudioside B and derivatives
US9877500B2 (en) 2007-03-14 2018-01-30 Concentrate Manufacturing Company Of Ireland Natural beverage products
US10207004B2 (en) 2014-04-04 2019-02-19 Douxmatok Ltd Method for producing sweetener compositions and sweetener compositions
US10212961B2 (en) 2005-07-14 2019-02-26 Douxmatok Ltd Sweetener compositions
US10231476B2 (en) 2014-04-04 2019-03-19 Douxmatok Ltd Sweetener compositions and foods, beverages, and consumable products made thereof
US10264811B2 (en) 2014-05-19 2019-04-23 Epc Natural Products Co., Ltd. Stevia sweetener with improved solubility
US10357052B2 (en) 2014-06-16 2019-07-23 Sweet Green Fields USA LLC Rebaudioside A and stevioside with improved solubilities
US10485256B2 (en) 2014-06-20 2019-11-26 Sweet Green Fields International Co., Limited Stevia sweetener with improved solubility with a cyclodextrin
US10729632B2 (en) 2013-08-02 2020-08-04 Tate & Lyle Ingredients Americas Llc Sweetner compositions
US11246835B2 (en) 2014-04-04 2022-02-15 Douxmatok Ltd Method for producing sweetener compositions and sweetener compositions

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Publication number Priority date Publication date Assignee Title
US8084073B2 (en) 2007-03-14 2011-12-27 Concentrate Manufacturing Company Of Ireland Anisic acid modified steviol glycoside sweetened beverage products

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US3296079A (en) * 1963-12-09 1967-01-03 Pfizer & Co C Products sweetened without sugar and characterized by freedom from aftertaste
US4288464A (en) * 1978-05-11 1981-09-08 Smith Walton J Flavor enhancer

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Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10212961B2 (en) 2005-07-14 2019-02-26 Douxmatok Ltd Sweetener compositions
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US8937168B2 (en) 2007-01-22 2015-01-20 Cargill, Incorporated Method of producing purified rebaudioside A compositions using solvent/antisolvent crystallization
EP2124648B1 (fr) 2007-03-14 2017-01-04 The Concentrate Manufacturing Company of Ireland Boisson ayant des édulcorants naturels avec un ou plusieurs composants de stévia et une source de baie
US9877500B2 (en) 2007-03-14 2018-01-30 Concentrate Manufacturing Company Of Ireland Natural beverage products
US9314048B2 (en) 2007-03-14 2016-04-19 The Concentrate Manufacturing Company Of Ireland Beverage products with non-nutritive sweetener and bitterant
RU2483584C2 (ru) * 2007-05-22 2013-06-10 Дзе Кока-Кола Компани Система доставки композиций натуральных высокоэффективных подсластителей и способы получения и применение указанных систем
WO2008147723A1 (fr) * 2007-05-22 2008-12-04 The Coca-Cola Company Systèmes d'administration pour compositions édulcorantes naturelles très puissantes, procédés de préparation et utilisations
CN101765376A (zh) * 2007-05-22 2010-06-30 可口可乐公司 用于天然高效甜味剂组合物的转运系统及其配制方法和用途
US9044038B2 (en) 2007-11-12 2015-06-02 San-Ei Gen F.F.I., Inc. Method of improving sweetness qualities of stevia extract
CN103053995A (zh) * 2007-11-12 2013-04-24 三荣源有限公司 改善甜叶菊提取物甜味的方法
CN103053995B (zh) * 2007-11-12 2014-12-10 三荣源有限公司 改善甜叶菊提取物甜味的方法
EP2826386A1 (fr) * 2009-06-16 2015-01-21 EPC (Beijing) Natural Products Co., Ltd. Composition de stévia comprenant rébaudioside D
US9131718B2 (en) 2009-06-16 2015-09-15 Epc (Beijing) Natural Products Co., Ltd. Process for rebaudioside D
EP2482676A2 (fr) * 2009-06-16 2012-08-08 Zhejiang Green World Bio-Tech Engineering Co., Ltd. Procede pour rebaudioside d
US9635878B2 (en) 2009-06-16 2017-05-02 Epc (Beijing) Natural Products Co., Ltd. Process for rebaudioside D
EP2482676A4 (fr) * 2009-06-16 2014-07-09 Zhejiang Green World Bio Tech Engineering Co Ltd Procede pour rebaudioside d
WO2011144831A1 (fr) * 2010-05-21 2011-11-24 Sine Sileo Agent édulcorant contenant un extrait de stévia rebaudiana bertoni
US10285425B2 (en) 2010-08-23 2019-05-14 Epc Natural Products Co. Ltd Rebaudioside A and stevioside compositions
US9578895B2 (en) 2010-08-23 2017-02-28 Epc (Beijing) Natural Products Co., Ltd. Rebaudioside A and stevioside compositions
US11202462B2 (en) 2010-08-23 2021-12-21 Sweet Green Fields International Co., Limited Rebaudioside A and stevioside compositions
US9789112B2 (en) 2010-10-28 2017-10-17 Hexal Ag Oral pharmaceutical film formulation for bitter tasting drugs
JP2013540795A (ja) * 2010-10-28 2013-11-07 ヘキサル・アクチェンゲゼルシャフト 苦味のある薬物のための経口用医薬フィルム製剤
US10583314B2 (en) 2011-01-28 2020-03-10 Tate & Lyle Ingredients Americas Llc Stevia blends containing rebaudioside B
US9402411B2 (en) 2011-01-28 2016-08-02 Tate & Lyle Ingredients Americas Llc Stevia blends containing rebaudioside B
US11801402B2 (en) 2011-01-28 2023-10-31 Tate & Lyle Solutions Usa Llc Stevia blends containing rebaudioside b
US9795156B2 (en) 2011-03-17 2017-10-24 E.P.C (Beijing) Plant Pharmaceutical Technology Co., Ltd Rebaudioside B and derivatives
US11510428B2 (en) 2011-03-17 2022-11-29 Sweet Green Fields International Co., Limited Rebaudioside B and derivatives
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