JP2013530677A - 溶解度を高めたテルペングリコシド - Google Patents
溶解度を高めたテルペングリコシド Download PDFInfo
- Publication number
- JP2013530677A JP2013530677A JP2012552150A JP2012552150A JP2013530677A JP 2013530677 A JP2013530677 A JP 2013530677A JP 2012552150 A JP2012552150 A JP 2012552150A JP 2012552150 A JP2012552150 A JP 2012552150A JP 2013530677 A JP2013530677 A JP 2013530677A
- Authority
- JP
- Japan
- Prior art keywords
- glucopyranosyl
- inclusion complex
- acid
- cyclodextrin
- rebaudioside
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
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- -1 Terpene glycosides Chemical class 0.000 title claims abstract description 227
- 229930182470 glycoside Natural products 0.000 title claims abstract description 93
- 235000007586 terpenes Nutrition 0.000 title claims abstract description 92
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 191
- 239000000203 mixture Substances 0.000 claims abstract description 94
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 33
- 235000013361 beverage Nutrition 0.000 claims abstract description 16
- 235000019640 taste Nutrition 0.000 claims abstract description 14
- RPYRMTHVSUWHSV-CUZJHZIBSA-N rebaudioside D Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RPYRMTHVSUWHSV-CUZJHZIBSA-N 0.000 claims description 120
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 108
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 99
- 239000002253 acid Substances 0.000 claims description 86
- QSRAJVGDWKFOGU-WBXIDTKBSA-N rebaudioside c Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]1(CC[C@H]2[C@@]3(C)[C@@H]([C@](CCC3)(C)C(=O)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC3)C(=C)C[C@]23C1 QSRAJVGDWKFOGU-WBXIDTKBSA-N 0.000 claims description 70
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical group O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 claims description 41
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- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 claims description 38
- 235000019203 rebaudioside A Nutrition 0.000 claims description 38
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- 235000019202 steviosides Nutrition 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 229930189775 mogroside Natural products 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
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- 150000008064 anhydrides Chemical class 0.000 claims description 5
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- 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
- A23L2/56—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 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
-
- 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
-
- 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
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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
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
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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
- A23L27/84—Flavour masking or reducing agents
Landscapes
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- Nutrition Science (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
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- Proteomics, Peptides & Aminoacids (AREA)
- Non-Alcoholic Beverages (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- General Preparation And Processing Of Foods (AREA)
- Jellies, Jams, And Syrups (AREA)
- Seasonings (AREA)
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016165298A (ja) * | 2012-03-26 | 2016-09-15 | ペプシコ, インコーポレイテッドPepsiCo Inc. | 水中のレバウディオサイドｄの溶解度を向上させる方法 |
| JP2019004905A (ja) * | 2018-09-10 | 2019-01-17 | アナリティコン ディスカバリー ゲーエムベーハー | 甘味料または甘味増強剤として使用される新規なトリペルテングリコシド |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102481372B (zh) * | 2009-06-24 | 2016-05-11 | 路易斯安那州州立大学及农业机械学院管理委员会 | 作为增溶剂的萜类糖苷及其组合 |
| US9578895B2 (en) | 2010-08-23 | 2017-02-28 | Epc (Beijing) Natural Products Co., Ltd. | Rebaudioside A and stevioside compositions |
| WO2013036366A1 (en) | 2011-09-07 | 2013-03-14 | Purecircle Usa Inc. | Highly soluble stevia sweetener |
| US9795156B2 (en) | 2011-03-17 | 2017-10-24 | E.P.C (Beijing) Plant Pharmaceutical Technology Co., Ltd | Rebaudioside B and derivatives |
| WO2013036768A1 (en) * | 2011-09-09 | 2013-03-14 | The Coca-Cola Company | Improved sweetener blend compositions |
| LT2793618T (lt) * | 2011-12-19 | 2018-03-26 | The Coca-Cola Company | Gėrimas, apimantis steviolio glikozidus |
| US10292412B2 (en) | 2012-02-15 | 2019-05-21 | Kraft Foods Global Brands Llc | High solubility natural sweetener compositions |
| US9752174B2 (en) * | 2013-05-28 | 2017-09-05 | Purecircle Sdn Bhd | High-purity steviol glycosides |
| CN108484698A (zh) * | 2012-12-19 | 2018-09-04 | 可口可乐公司 | 用于提高莱鲍迪苷x溶解度的组合物和方法 |
| US20140171519A1 (en) | 2012-12-19 | 2014-06-19 | Indra Prakash | Compositions and methods for improving rebaudioside x solubility |
| US9522929B2 (en) * | 2014-05-05 | 2016-12-20 | Conagen Inc. | Non-caloric sweetener |
| 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 |
| EP3283614B1 (en) | 2015-04-14 | 2020-07-08 | Conagen Inc. | Production of non-caloric sweeteners using engineered whole-cell catalysts |
| BR112018013985B1 (pt) | 2016-01-07 | 2022-07-19 | Purecircle Usa Inc | Método para produzir uma composição de glicosídeo de esteviol altamente solúvel |
| MY207190A (en) | 2017-10-06 | 2025-02-05 | Cargill Inc | Readily dissolvable steviol glycoside compositions |
| US20210127726A1 (en) * | 2018-04-30 | 2021-05-06 | The Coca-Cola Company | Methods for improving the solubility of steviol glycoside mixtures, and uses |
| EP3952667A1 (en) | 2019-04-06 | 2022-02-16 | Cargill, Incorporated | Sensory modifiers |
| US10941084B1 (en) * | 2020-05-23 | 2021-03-09 | King Saud University | Fertilizers derived from date syrup |
| EP4018838B1 (de) | 2020-12-23 | 2024-05-22 | Red Bull GmbH | Anlage zur herstellung eines wässrigen lebensmittels, verwendung eines ft-nir-spektrometers in einer anlage zur herstellung eines wässrigen lebensmittels, mischvorrichtung für eine anlage zur herstellung eines wässrigen lebensmittels sowie verfahren zur herstellung von wässrigen lebensmitteln |
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| JPS57182301A (en) * | 1981-01-23 | 1982-11-10 | Wellcome Found | Composite body of sugar-containing compound and cycloamlose and manufacture |
| JPS6098957A (ja) * | 1983-11-02 | 1985-06-01 | Sanraku Inc | 新規なステビオサイド類甘味料及びその製造法 |
| JPS60188035A (ja) * | 1984-03-08 | 1985-09-25 | Riken Vitamin Co Ltd | ステビオサイドの呈味改善法 |
| JPS642552A (en) * | 1987-06-24 | 1989-01-06 | Dainippon Seito Kk | Method for reducing bitter taste of extract of gymnema silvesta |
| JPH01120263A (ja) * | 1987-11-05 | 1989-05-12 | Meiji Seito Kk | ギムネマシルベスタ抽出物を含有する糖組成物並びにその製法 |
| JPH0775536A (ja) * | 1993-06-17 | 1995-03-20 | Oomiya Yakugyo Kk | ケルセチン配糖体を含有する清涼飲料水 |
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- 2011-02-08 EP EP11704154A patent/EP2533651A1/en not_active Withdrawn
- 2011-02-08 JP JP2012552150A patent/JP2013530677A/ja active Pending
- 2011-02-08 WO PCT/US2011/024036 patent/WO2011097620A1/en not_active Ceased
- 2011-02-08 US US13/022,727 patent/US20110195161A1/en not_active Abandoned
- 2011-02-08 CN CN2011800086134A patent/CN103079411A/zh active Pending
- 2011-02-08 KR KR1020127023543A patent/KR20120125524A/ko not_active Ceased
- 2011-02-08 CA CA2789102A patent/CA2789102A1/en not_active Abandoned
- 2011-02-08 AU AU2011213602A patent/AU2011213602B2/en active Active
- 2011-02-08 MX MX2012009166A patent/MX342797B/es active IP Right Grant
- 2011-02-08 BR BRBR112012020316-9A patent/BR112012020316A2/pt not_active Application Discontinuation
- 2011-02-08 MY MYPI2012003572A patent/MY161487A/en unknown
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2012
- 2012-08-02 IL IL221256A patent/IL221256A0/en unknown
- 2012-08-06 ZA ZA2012/05923A patent/ZA201205923B/en unknown
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2015
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| JPS57182301A (en) * | 1981-01-23 | 1982-11-10 | Wellcome Found | Composite body of sugar-containing compound and cycloamlose and manufacture |
| JPS6098957A (ja) * | 1983-11-02 | 1985-06-01 | Sanraku Inc | 新規なステビオサイド類甘味料及びその製造法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016165298A (ja) * | 2012-03-26 | 2016-09-15 | ペプシコ, インコーポレイテッドPepsiCo Inc. | 水中のレバウディオサイドｄの溶解度を向上させる方法 |
| 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 |
| JP2019004905A (ja) * | 2018-09-10 | 2019-01-17 | アナリティコン ディスカバリー ゲーエムベーハー | 甘味料または甘味増強剤として使用される新規なトリペルテングリコシド |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103079411A (zh) | 2013-05-01 |
| IL221256A0 (en) | 2012-10-31 |
| JP2016073295A (ja) | 2016-05-12 |
| WO2011097620A1 (en) | 2011-08-11 |
| RU2586161C2 (ru) | 2016-06-10 |
| BR112012020316A2 (pt) | 2015-09-01 |
| AU2011213602B2 (en) | 2016-06-23 |
| ZA201205923B (en) | 2015-08-26 |
| EP2533651A1 (en) | 2012-12-19 |
| RU2012137253A (ru) | 2014-03-20 |
| AU2011213602A1 (en) | 2012-09-20 |
| MY161487A (en) | 2017-04-14 |
| KR20120125524A (ko) | 2012-11-15 |
| RU2586161C9 (ru) | 2016-10-27 |
| CA2789102A1 (en) | 2011-08-11 |
| MX342797B (es) | 2016-10-13 |
| MX2012009166A (es) | 2012-08-23 |
| US20110195161A1 (en) | 2011-08-11 |
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