BR112015021402B1 - Método para isolar frações azuis de antocianina - Google Patents
Método para isolar frações azuis de antocianina Download PDFInfo
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- BR112015021402B1 BR112015021402B1 BR112015021402-9A BR112015021402A BR112015021402B1 BR 112015021402 B1 BR112015021402 B1 BR 112015021402B1 BR 112015021402 A BR112015021402 A BR 112015021402A BR 112015021402 B1 BR112015021402 B1 BR 112015021402B1
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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
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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
- A23L2/70—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter
- A23L2/78—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter by ion-exchange
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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
- 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
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
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- A—HUMAN NECESSITIES
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- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
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- 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, e.g. ion-exchange, ion-pair, ion-suppression or ion-exclusion
- B01D15/361—Ion-exchange
- B01D15/362—Cation-exchange
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- 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
- B01D15/42—Selective adsorption, e.g. chromatography characterised by the development mode, e.g. by displacement or by elution
- B01D15/424—Elution mode
- B01D15/426—Specific type of solvent
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
-
- 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
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| WO2014152417A2 (en) | 2013-03-15 | 2014-09-25 | Mars, Incorporated | Method of isolating blue anthocyanin fractions |
| CN104961783B (zh) * | 2015-04-17 | 2018-07-10 | 浙江惠松制药有限公司 | 一种有效提取花青素和花色苷的方法 |
| RU2721836C2 (ru) * | 2015-06-30 | 2020-05-22 | Марс, Инкорпорейтед | Композиции красителей и способы их использования |
| CN110248551A (zh) | 2016-12-29 | 2019-09-17 | 马斯公司 | 包含碳酸钙粒子的食用型油墨配制物 |
| US12302921B2 (en) | 2018-06-28 | 2025-05-20 | Mars, Incorporated | Edible ink formulations including calcium carbonate |
| US20210259274A1 (en) | 2018-06-28 | 2021-08-26 | Wm. Wrigley Jr. Company | Titanium free opacifying compositions |
| BR112021003771A2 (pt) | 2018-08-31 | 2021-05-25 | Mars, Incorporated | composições de corantes à base de antocianina e seus métodos de uso |
| AU2020357887A1 (en) | 2019-10-01 | 2022-04-07 | Mars, Incorporated | Enzymatic treatment of anthocyanins |
| EP3939437A1 (en) * | 2020-07-17 | 2022-01-19 | GNT Group B.V. | A composition comprising spirulina extract |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3361631A (en) | 1963-09-30 | 1968-01-02 | Sandoz Ag | Method of sugar coating pharmaceutical tablets |
| DE1482489A1 (de) | 1965-01-13 | 1970-03-12 | Boehringer Mannheim Gmbh | Vollautomatisches Dragierverfahren |
| NL6601426A (enExample) | 1965-02-12 | 1966-08-15 | ||
| US4172902A (en) | 1978-05-26 | 1979-10-30 | The United States Of America As Represented By The Secretary Of Agriculture | Stable foods and beverages containing the anthocyanin, peonidin 3-(dicaffeylsophoroside)-5-glucoside |
| JPS6025181B2 (ja) | 1982-10-04 | 1985-06-17 | フロイント産業株式会社 | パンコ−チング装置 |
| US4681766A (en) | 1986-01-07 | 1987-07-21 | Warner-Lambert Company | Coatings for chewing gums containing gum arabic and a soluble calcium salt |
| JPH083047B2 (ja) | 1986-06-21 | 1996-01-17 | サントリー株式会社 | 天然青色系色素組成物及びそれを用いた着色剤 |
| DK0719093T3 (da) | 1993-09-15 | 2000-06-05 | Wrigley W M Jun Co | Tyggegummi med hårdt overtræk og forbedret holdbarhed og med blandede polyocoatinger |
| JPH07188572A (ja) | 1993-12-27 | 1995-07-25 | Kyodo Nyugyo Kk | マロ−由来の天然色素 |
| DE876109T1 (de) | 1996-01-22 | 2001-07-05 | Chr. Hansen A/S, Hoersholm | In wasser dispergierbare zusammensetzungen, die ein natuerliches hydrophobes pigment enthalten, verfahren zu ihrer herstellung und ihre verwendung |
| US6541048B2 (en) | 1999-09-02 | 2003-04-01 | Wm. Wrigley Jr. Company | Coated chewing gum products containing an acid blocker and process of preparing |
| AU5248800A (en) | 2000-03-16 | 2001-09-24 | San-Ei Gen F.F.I., Inc. | Fading inhibitors |
| CA2410366C (en) | 2000-05-26 | 2009-08-11 | San-Ei Gen F.F.I., Inc. | Deodorized colorant of brassicaceae plant |
| US6572900B1 (en) | 2000-06-09 | 2003-06-03 | Wm. Wrigley, Jr. Company | Method for making coated chewing gum products including a high-intensity sweetener |
| EP1279703B1 (en) | 2001-07-26 | 2006-04-19 | Chr. Hansen A/S | Food colouring substances based on Anthocyanin |
| US6881430B2 (en) | 2001-07-26 | 2005-04-19 | Chr. Hansen A/S | Food coloring substances and method for their preparation |
| JP4590034B2 (ja) | 2002-01-31 | 2010-12-01 | 三菱商事フードテック株式会社 | 硬質糖衣製剤、糖衣液及び硬質糖衣製剤の製造方法 |
| JP4134906B2 (ja) | 2002-02-01 | 2008-08-20 | 三栄源エフ・エフ・アイ株式会社 | 精製紫トウモロコシ色素及びその調製方法 |
| DE10227151B4 (de) | 2002-06-18 | 2007-03-15 | Wild Flavors Berlin Gmbh & Co. Kg | Extrakt aus Nebenprodukten der Nussverarbeitung, Verfahren zu dessen Herstellung und dessen Verwendung |
| FR2842993B1 (fr) * | 2002-07-31 | 2006-02-17 | Mars Inc | Nouvelle composition de confiserie |
| US7378118B2 (en) | 2002-08-14 | 2008-05-27 | Wm. Wrigley Jr. Company | Methods for manufacturing coated confectionary products |
| US20040105919A1 (en) | 2002-12-02 | 2004-06-03 | Mars, Incorporated | Processing system having a process injection apparatus |
| WO2005007088A2 (en) * | 2003-07-03 | 2005-01-27 | Unibar Corporation | Stabilized anthocyanin extract from garcinia indica |
| US7279189B2 (en) | 2004-07-02 | 2007-10-09 | Colormaker, Inc. | Stabilized natural blue and green colorants |
| CA2573490A1 (en) | 2004-07-10 | 2006-01-26 | The Research Foundation Of State University Of New York | Production of flavonoids by recombinant microorganisms |
| JP5598830B2 (ja) | 2004-10-29 | 2014-10-01 | サントリーホールディングス株式会社 | アントシアニンの３’位への芳香族アシル基転移酵素をコードする遺伝子を用いたアントシアニン色素の安定化ならびに青色化方法 |
| EP1828331B1 (en) | 2004-12-22 | 2019-01-30 | Colarôme Inc. | Natural water-insoluble encapsulation compositions and processes for preparing same |
| RU2302423C2 (ru) * | 2005-06-10 | 2007-07-10 | Закрытое акционерное общество "Научно-производственное объединение "ТЕХКОН" | Способ выделения биологически активных антоцианов |
| WO2008111589A1 (ja) * | 2007-03-12 | 2008-09-18 | National University Corporation Kagawa University | 精製アントシアニンの製造方法 |
| FR2914311B1 (fr) | 2007-03-28 | 2011-02-11 | Diana Naturals | Modification de la nuance colorante d'anthocyanes pour l'obtention de substances colorantes |
| EP2070422A1 (en) | 2007-12-05 | 2009-06-17 | Südzucker Aktiengesellschaft Mannheim/Ochsenfurt | Confectionery products promoting dental health |
| CA2714084C (en) * | 2008-02-06 | 2015-09-29 | The Ohio State University Research Foundation | High-purity fractionation of anthocyanins from fruits and vegetables |
| US8575334B2 (en) | 2008-02-06 | 2013-11-05 | The Ohio State University Research Foundation | High-purity fractionation of anthocyanins from fruits and vegetables |
| US8557319B2 (en) | 2008-03-28 | 2013-10-15 | Wild Flavors, Inc. | Stable natural color process, products and use thereof |
| FR2930557B1 (fr) | 2008-04-29 | 2013-08-30 | Lvmh Rech | Matieres colorantes d'origine vegetale et leur utilisation pour colorer des compositions, en particulier des compositions cosmetiques |
| US20090298952A1 (en) | 2008-05-07 | 2009-12-03 | Brimmer Karen S | Platable soluble dyes |
| JP5833449B2 (ja) | 2008-12-18 | 2015-12-16 | ダイアナプラントサイエンシズ インコーポレイテッド | グルコシノレート混入が減少した天然物を生成するための植物細胞培養 |
| US8765180B2 (en) | 2009-01-07 | 2014-07-01 | Chr. Hansen A/S | Composition comprising calcium carbonate as a white pigment |
| US8962327B2 (en) | 2009-04-03 | 2015-02-24 | Dianaplantsciences, S.A.S. | Methods for creating color variation in anthocyanins produced by cell culture |
| GB0908397D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leeds | Natural hair dyes |
| CA2781256C (en) | 2009-11-25 | 2017-11-07 | Sensient Colors Inc. | Natural blue-shade colorants and methods of making and using same |
| JP2012067241A (ja) | 2010-09-27 | 2012-04-05 | Riken Vitamin Co Ltd | クチナシ青色素の製造方法 |
| US9427007B2 (en) | 2010-11-05 | 2016-08-30 | Chr. Hansen Natural Colors A/S | Multiple emulsions for colorants |
| US20130165531A1 (en) | 2011-06-13 | 2013-06-27 | E.P.C. (Beijing) Plant Pharmaceutical Technology Co., Ltd. | Anthocyanin based colorant compositions |
| EP2545787B1 (de) | 2011-07-11 | 2016-04-13 | RUDOLF WILD GmbH & CO. KG | Anthocyanhaltige Zusammensetzung |
| MX2014000460A (es) | 2011-07-15 | 2014-02-20 | Nestec Sa | Encapsulado azul de grado alimetario y proceso para su produccion. |
| WO2013106179A1 (en) | 2011-12-19 | 2013-07-18 | Sensient Colors Llc | Color compositions and methods of making color compositions comprising starch as a matrix |
| US20130184359A1 (en) | 2012-01-13 | 2013-07-18 | Karim Nafisi-Movaghar | Processes for Extracting Colors from Hibiscus Plants |
| CA2881192A1 (en) | 2012-08-09 | 2014-02-13 | Nestec S.A. | Anthocyanin colouring composition |
| WO2014152417A2 (en) | 2013-03-15 | 2014-09-25 | Mars, Incorporated | Method of isolating blue anthocyanin fractions |
| RU2636761C2 (ru) | 2013-03-15 | 2017-11-28 | Марс, Инкорпорейтед | Стабилизация натуральных синих антоциансодержащих красителей и приготовленных продуктов |
| CN105339437A (zh) | 2013-03-15 | 2016-02-17 | 马斯公司 | 含花青素苷的天然蓝色着色剂 |
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2014
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| EP2986675A2 (en) | 2016-02-24 |
| BR112015021402A2 (enExample) | 2017-08-22 |
| AU2014239875A1 (en) | 2015-11-05 |
| GB2527453A (en) | 2015-12-23 |
| MX362026B (es) | 2019-01-04 |
| HK1215040A1 (zh) | 2016-08-12 |
| JP2016519177A (ja) | 2016-06-30 |
| EP2986675B1 (en) | 2016-10-05 |
| RU2015144064A (ru) | 2017-04-27 |
| GB201517443D0 (en) | 2015-11-18 |
| GB2527453B (en) | 2017-03-15 |
| RU2629257C2 (ru) | 2017-08-28 |
| US10119029B2 (en) | 2018-11-06 |
| JP5981675B2 (ja) | 2016-08-31 |
| CA2904650A1 (en) | 2014-09-25 |
| MX2015011349A (es) | 2016-06-06 |
| CN105229084B (zh) | 2017-09-01 |
| AU2014239875B2 (en) | 2016-02-04 |
| WO2014152417A3 (en) | 2014-11-20 |
| US20170204269A1 (en) | 2017-07-20 |
| US9598581B2 (en) | 2017-03-21 |
| BR112015021402A8 (pt) | 2021-09-08 |
| CN105229084A (zh) | 2016-01-06 |
| CA2904650C (en) | 2016-07-12 |
| US20160017150A1 (en) | 2016-01-21 |
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Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 14/03/2014, OBSERVADAS AS CONDICOES LEGAIS. |