CN106986905B - 处理糖苷的混合物以获得更纯的形式的一种或多种这些糖苷的方法 - Google Patents
处理糖苷的混合物以获得更纯的形式的一种或多种这些糖苷的方法 Download PDFInfo
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- CN106986905B CN106986905B CN201710007545.9A CN201710007545A CN106986905B CN 106986905 B CN106986905 B CN 106986905B CN 201710007545 A CN201710007545 A CN 201710007545A CN 106986905 B CN106986905 B CN 106986905B
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Classifications
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- A23L27/30—Artificial sweetening agents
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- C07H15/24—Condensed ring systems having three or more rings
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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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/52—Adding ingredients
- A23L2/60—Sweeteners
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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 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- 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
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- Polymers & Plastics (AREA)
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- Biotechnology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Saccharide Compounds (AREA)
- Seasonings (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Extraction Or Liquid Replacement (AREA)
- Processing Of Solid Wastes (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
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| CN2011800151398A Pending CN102811627A (zh) | 2010-01-28 | 2011-01-27 | 处理糖苷的混合物以获得更纯的形式的一种或多种这些糖苷的方法 |
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| KR20120027363A (ko) | 2009-06-16 | 2012-03-21 | 이피씨 (베이징) 내추럴 프로덕츠 컴퍼니, 리미티드 | 뒷맛을 감소시키거나 제거하기 위한 레바우디오사이드 ｄ를 포함하는 조성물 및 그의 제조 방법 |
| AU2011210818B2 (en) * | 2010-01-28 | 2014-10-30 | Cargill, Incorporated | Methods to treat mixtures of glycosides to obtain one or more of these glycosides in more pure form |
| US20150344512A1 (en) | 2011-12-19 | 2015-12-03 | Purecircle Usa Inc. | Methods of purifying steviol glycosides and uses of the same |
| US9578895B2 (en) * | 2010-08-23 | 2017-02-28 | Epc (Beijing) Natural Products Co., Ltd. | Rebaudioside A and stevioside compositions |
| WO2012068457A1 (en) | 2010-11-19 | 2012-05-24 | Cargill, Incorporated | Method for the enrichment of rebaudioside b and/or rebaudioside d in stevia-derived glycoside compositions using adsorb-desorb chromatography with a macroporous neutral adsorbent resin |
| US9510611B2 (en) * | 2010-12-13 | 2016-12-06 | Purecircle Sdn Bhd | Stevia composition to improve sweetness and flavor profile |
| US8962698B2 (en) | 2011-01-28 | 2015-02-24 | Tate & Lyle Ingredients Americas Llc | Rebaudioside-mogroside V blends |
| JP6010552B2 (ja) * | 2011-01-28 | 2016-10-19 | テート アンド ライル イングリーディエンツ アメリカズ エルエルシー | レバウディオサイドｂを含有するステビアブレンド |
| ES2717431T3 (es) * | 2011-02-10 | 2019-06-21 | Purecircle Usa | Composición a base de estevia |
| US9795156B2 (en) | 2011-03-17 | 2017-10-24 | E.P.C (Beijing) Plant Pharmaceutical Technology Co., Ltd | Rebaudioside B and derivatives |
| ES3032342T3 (en) * | 2011-09-06 | 2025-07-17 | Pepsico Inc | Rebaudioside d sweeteners and food products sweetened with rebaudioside d |
| EP3345490B1 (en) | 2011-12-19 | 2023-11-08 | The Coca-Cola Company | Beverage comprising rebaudioside x |
| GB201217700D0 (en) * | 2012-08-01 | 2012-11-14 | Tate & Lyle Ingredients | Sweetener compositions containing rebaudioside B |
| BR112015006543A2 (pt) | 2012-09-25 | 2017-07-04 | Cargill Inc | misturas de esteviosídeos |
| EP3653636A1 (en) | 2012-12-19 | 2020-05-20 | The Coca-Cola Company | Compositions and methods for improving rebaudioside x solubility |
| US20140171519A1 (en) | 2012-12-19 | 2014-06-19 | Indra Prakash | Compositions and methods for improving rebaudioside x solubility |
| DK3714699T3 (da) | 2013-06-07 | 2025-01-20 | Purecircle Usa Inc | Stevia-ekstrakt indeholdende udvalgte steviolglycosider som aroma-, salt- og sødmeprofilmodifikator |
| US10905146B2 (en) | 2013-07-12 | 2021-02-02 | The Coca-Cola Company | Compositions for improving rebaudioside M solubility |
| CN103709215B (zh) * | 2013-12-31 | 2016-01-06 | 天津北洋百川生物技术有限公司 | 一种从甜菊糖结晶母液糖中提取莱鲍迪甙d的方法 |
| 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 |
| PL3017708T3 (pl) * | 2014-10-24 | 2018-11-30 | Red Bull Gmbh | Kompozycja słodząca |
| CA2968280A1 (en) * | 2014-11-24 | 2016-06-02 | Cargill, Incorporated | Glycoside compositions |
| JP6845159B2 (ja) | 2015-05-20 | 2021-03-17 | カーギル インコーポレイテッド | グリコシド組成物 |
| CN105037458B (zh) | 2015-07-23 | 2018-12-28 | 诸城市浩天药业有限公司 | 一种甜菊糖d苷晶型a、其制备方法及其应用 |
| US11251343B2 (en) * | 2017-02-08 | 2022-02-15 | Current Lighting Solutions, Llc | LED design of lower CCT utilizing PFS phosphor |
| JP7391017B2 (ja) | 2017-10-06 | 2023-12-04 | カーギル インコーポレイテッド | ステビオール配糖体溶解度エンハンサー |
| CN109456371A (zh) * | 2018-10-16 | 2019-03-12 | 桂林莱茵生物科技股份有限公司 | 一种高效甜菊糖苷混合物的制备方法 |
| WO2020210118A1 (en) | 2019-04-06 | 2020-10-15 | Cargill, Incorporated | Sensory modifiers |
| JP2020031640A (ja) * | 2019-10-04 | 2020-03-05 | カーギル インコーポレイテッド | 配糖体混合物 |
| EP4262435A1 (en) * | 2020-12-16 | 2023-10-25 | CORN Products Development Inc. | Method for purifying a crude composition comprising one or more steviol glycosides |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101090642A (zh) * | 2004-10-18 | 2007-12-19 | 甜美绿色田野有限责任公司 | 生产纯新蛇菊苷a的高收率方法 |
| WO2008091547A2 (en) * | 2007-01-22 | 2008-07-31 | Cargill, Incorporated | Method of producing purified rebaudioside a compositions using solvent/antisolvent crystallization |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51142570A (en) | 1975-06-04 | 1976-12-08 | Morita Kagaku Kogyo | Method of imparting sweetness to food or pharmaceutical agent |
| JPS5262300A (en) | 1975-11-13 | 1977-05-23 | Ajinomoto Co Inc | Isolation of bibaudioside-a by crystallization |
| JPS56121453A (en) | 1980-02-27 | 1981-09-24 | Ajinomoto Co Inc | Separation of stevioside and rebaudioside a |
| JPS56121454A (en) | 1980-02-27 | 1981-09-24 | Ajinomoto Co Inc | Separation of stevioside and rebaudioside a by crystallization |
| US4361697A (en) | 1981-05-21 | 1982-11-30 | F. K. Suzuki International, Inc. | Extraction, separation and recovery of diterpene glycosides from Stevia rebaudiana plants |
| US4599403A (en) * | 1985-10-07 | 1986-07-08 | Harold Levy | Method for recovery of stevioside |
| EP0302948B1 (de) | 1987-07-21 | 1993-12-01 | Roger H. Giovanetto | Verfahren zur Gewinnung von Steviosiden aus pflanzlichem Rohmaterial |
| JP3111203B2 (ja) | 1987-12-26 | 2000-11-20 | 中里 隆憲 | ステビア新品種に属する植物 |
| US5962678A (en) * | 1996-09-13 | 1999-10-05 | Alberta Research Council | Method of extracting selected sweet glycosides from the Stevia rebaudiana plant |
| CN1243835A (zh) | 1998-08-05 | 2000-02-09 | 黑龙江垦区海林甜菊糖有限责任公司 | 莱苞迪甙a提取方法 |
| KR100944242B1 (ko) * | 2004-10-04 | 2010-02-24 | 카운슬 오브 사이언티픽 앤드 인더스트리얼 리서치 | 스테비아 레바우디아나 베르토니로부터 스테비오사이드를생산하는 방법 |
| US7838044B2 (en) | 2004-12-21 | 2010-11-23 | Purecircle Sdn Bhd | Extraction, separation and modification of sweet glycosides from the Stevia rebaudiana plant |
| US7862845B2 (en) * | 2005-10-11 | 2011-01-04 | Purecircle Sdn Bhd | Process for manufacturing a sweetener and use thereof |
| CN101472487B (zh) * | 2006-06-19 | 2013-05-01 | 可口可乐公司 | 甜菊双糖苷a组合物及其纯化方法 |
| US8791253B2 (en) | 2006-06-19 | 2014-07-29 | The Coca-Cola Company | Rebaudioside A composition and method for purifying rebaudioside A |
| US8017168B2 (en) * | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
| CN101200480B (zh) * | 2006-12-15 | 2011-03-30 | 成都华高药业有限公司 | 莱鲍迪甙a的提取方法 |
| CN101220062A (zh) | 2008-01-23 | 2008-07-16 | 石任兵 | 一种同时制备甜菊苷和莱鲍迪苷a的方法 |
| EP2416670A4 (en) * | 2009-04-09 | 2014-05-21 | Cargill Inc | SWEET COMPOSITION WITH REBAUDIOSIDE A HIGH SOLUBILITY FORM AND MANUFACTURING PROCESS |
| AU2011210818B2 (en) * | 2010-01-28 | 2014-10-30 | Cargill, Incorporated | Methods to treat mixtures of glycosides to obtain one or more of these glycosides in more pure form |
-
2011
- 2011-01-27 AU AU2011210818A patent/AU2011210818B2/en not_active Expired - Fee Related
- 2011-01-27 CN CN201710007545.9A patent/CN106986905B/zh active Active
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- 2011-01-27 CN CN2011800151398A patent/CN102811627A/zh active Pending
- 2011-01-27 US US13/575,751 patent/US9024012B2/en active Active
- 2011-01-27 BR BRBR112012018791-0A patent/BR112012018791A2/pt not_active IP Right Cessation
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- 2011-01-27 RU RU2012136639/13A patent/RU2012136639A/ru not_active Application Discontinuation
- 2011-01-27 EP EP11737652.5A patent/EP2528455A4/en not_active Withdrawn
- 2011-01-27 KR KR20127022004A patent/KR20120117895A/ko not_active Withdrawn
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- 2011-01-27 PE PE2012001052A patent/PE20121696A1/es not_active Application Discontinuation
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2015
- 2015-05-01 US US14/702,347 patent/US20160009749A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101090642A (zh) * | 2004-10-18 | 2007-12-19 | 甜美绿色田野有限责任公司 | 生产纯新蛇菊苷a的高收率方法 |
| WO2008091547A2 (en) * | 2007-01-22 | 2008-07-31 | Cargill, Incorporated | Method of producing purified rebaudioside a compositions using solvent/antisolvent crystallization |
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| EP2528455A4 (en) | 2013-11-27 |
| MX2012008546A (es) | 2012-09-07 |
| CA2788359A1 (en) | 2011-08-04 |
| EP2528455A1 (en) | 2012-12-05 |
| PE20121696A1 (es) | 2012-12-16 |
| US20120289687A1 (en) | 2012-11-15 |
| AU2011210818B2 (en) | 2014-10-30 |
| JP2013518118A (ja) | 2013-05-20 |
| RU2012136639A (ru) | 2014-03-10 |
| KR20120117895A (ko) | 2012-10-24 |
| WO2011094423A1 (en) | 2011-08-04 |
| CN102811627A (zh) | 2012-12-05 |
| CA2788359C (en) | 2019-01-08 |
| US20160009749A1 (en) | 2016-01-14 |
| CN106986905A (zh) | 2017-07-28 |
| BR112012018791A2 (pt) | 2015-09-01 |
| US9024012B2 (en) | 2015-05-05 |
| MX337550B (es) | 2016-03-10 |
| AU2011210818A1 (en) | 2012-08-23 |
| AR080051A1 (es) | 2012-03-07 |
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