WO2009012070A1 - Process for producing a proanthocyanidin extract - Google Patents

Process for producing a proanthocyanidin extract Download PDF

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Publication number
WO2009012070A1
WO2009012070A1 PCT/US2008/069294 US2008069294W WO2009012070A1 WO 2009012070 A1 WO2009012070 A1 WO 2009012070A1 US 2008069294 W US2008069294 W US 2008069294W WO 2009012070 A1 WO2009012070 A1 WO 2009012070A1
Authority
WO
WIPO (PCT)
Prior art keywords
proanthocyanin
stream
concentrated
enriched
reduced
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.)
Ceased
Application number
PCT/US2008/069294
Other languages
English (en)
French (fr)
Inventor
Harold L. Mantius
Lawrence Rose
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ocean Spray Cranberries Inc
Original Assignee
Ocean Spray Cranberries Inc
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 Ocean Spray Cranberries Inc filed Critical Ocean Spray Cranberries Inc
Priority to JP2010516172A priority Critical patent/JP2010533648A/ja
Priority to AU2008276266A priority patent/AU2008276266A1/en
Priority to CN200880024498A priority patent/CN101796044A/zh
Priority to CA2692688A priority patent/CA2692688C/en
Priority to EP08781419.0A priority patent/EP2175731A4/en
Publication of WO2009012070A1 publication Critical patent/WO2009012070A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
    • A23L19/03—Products from fruits or vegetables; Preparation or treatment thereof consisting of whole pieces or fragments without mashing the original pieces
    • 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
    • A23L19/00—Products from fruits or vegetables; 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof containing fruit or vegetable juices
    • A23L2/08—Concentrating or drying of juices
    • A23L2/082—Concentrating or drying of juices by membrane processes
    • A23L2/085—Concentrating or drying of juices by membrane processes by osmosis, reverse osmosis, electrodialysis
    • 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
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof containing fruit or vegetable juices
    • A23L2/08—Concentrating or drying of juices
    • A23L2/082—Concentrating or drying of juices by membrane processes
    • A23L2/087—Concentrating or drying of juices by membrane processes by ultrafiltration, microfiltration
    • 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
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof containing fruit or vegetable juices
    • A23L2/08—Concentrating or drying of juices
    • A23L2/10—Concentrating or drying of juices by heating or contact with dry gases
    • 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
    • A23L2/385—Concentrates of non-alcoholic beverages
    • 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
    • A23L2/385—Concentrates of non-alcoholic beverages
    • A23L2/39—Dry compositions
    • A23L2/395—Dry compositions in a particular shape or form
    • 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
    • A23L2/72—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter by filtration
    • A23L2/74—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter by filtration using membranes, e.g. osmosis, ultrafiltration
    • 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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
    • A23L5/51—Concentration
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
    • B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
    • B01D61/025—Reverse osmosis; Hyperfiltration
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
    • B01D61/14—Ultrafiltration; Microfiltration
    • B01D61/145—Ultrafiltration
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • 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

Definitions

  • proanthocyanidins also called condensed tannins or procyanidins
  • the selective capture and dry weight concentration of proanthocyanidin compounds (PACs) may thus open up novel opportunities in the field of product application ⁇ e.g., retail beverages, lozenges, etc. ⁇ relative to delivering those unique benefits.
  • a method which uses an Ultrafiltration (UF) membrane system to fractionate a PAC-containing liquid feedstock ⁇ e.g., cranberry juice] into a PAC-reduced permeate stream and PAC-enriched retentate stream.
  • a PAC-containing liquid feedstock e.g., cranberry juice
  • PAC-enriched retentate stream a substantial fraction of the higher molecular weight PACs (and/or relatively high molecular weight aggregates of PACs) present are selectively retained in the retentate, with the remaining array of constituent lower molecular weight soluble solids ⁇ e.g., sugars, acids, anthocyanins, etc. ⁇ preferentially passing through the membrane as permeate.
  • constituent lower molecular weight soluble solids e.g., sugars, acids, anthocyanins, etc.
  • extracts can be manufactured to virtually any preset, specified PAC dry weight content ⁇ e.g., at 5%, 10%, 15%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, and 98% ⁇ .
  • the selective fractionation of PACs based on molecular weight, with the lower molecular weight fraction passing through the membrane as permeate, and the higher molecular weight fraction retained as retentate may also result in an extract of enhanced bioactivity per unit weight of PACs.
  • the method described herein can also be used to provide a clarified PAC extract potentially well suited for use in retail beverage formulations ⁇ e.g., low calorie isotonic beverages ⁇ , due to a substantial removal of bitter lower molecular weight non- PAC phenolic compounds into the PAC-reduced permeate stream.
  • a PAC-enriched fruit or vegetable extract can be used for a variety of purposes.
  • an extract having a high dry weight concentration of PACs can be combined with water, juices or other beverages to provide a beverage with enhanced health benefits.
  • An extract having a high dry weight concentration of PACs can be dried and combined with other ingredients to provide a pill or capsule that is useful as a dietary supplement.
  • a PAC -enriched fruit or vegetable extract can also be used to enhance the health benefits of various foods. For example, such an extract could be applied to dried fruits, for example dried cranberries, to create a dried fruit with enhanced health benefits.
  • a method comprising: (a) providing a volume of proanthocyanin-containing liquid feedstock; (b) passing the proanthocyanin-containing liquid feedstock to an ultrafiltration feed tank; (c) filtering the material in the ultrafiltration feed tank through an ultrafiltration membrane system to fractionate the material into a proanthocyanin-reduced permeate stream and a proanthocyanin-enriched retentate stream; (d) collecting the proanthocyanin-reduced permeate stream; and (e) passing the proanthocyanin-enriched retentate stream to the ultrafiltration feed tank until the volume of proanthocyanin-containing liquid feedstock is exhausted and thereafter collecting the proanthocyanin-enriched retentate stream.
  • the proanthocyanin-containing liquid feedstock is a fruit juice or a fruit juice fraction.
  • the fruit juice or fruit juice fraction is substantially free of insoluble fruit solids
  • the fruit juice or fruit juice fraction is cranberry juice or a cranberry juice fraction
  • the method further comprises concentrating the proanthocyanin-reduced permeate stream to create a concentrated proanthocyanin-reduced permeate;
  • the proanthocyanin-reduced permeate stream is concentrated by reverse osmosis;
  • the proanthocyanin-reduced permeate stream is concentrated by evaporation;
  • the proanthocyanin-reduced permeate stream is concentrated by reverse osmosis and evaporation;
  • the method further comprises concentrating the collected proanthocyanin- enriched retentate stream to create a concentrated proanthocyanin-enriched retentate;
  • the proanthocyanin-enriched retentate stream is concentrated by reverse
  • FIG. 1 a flow diagram is shown of one embodiment of a UF membrane system modified batch process for preparing a PAC-enriched fruit or vegetable extract.
  • the process begins with a clarified ⁇ 5 NTU ⁇ PAC-containing liquid feedstock ⁇ e.g., 2 Brix cranberry juice ⁇ .
  • the clarified PAC- containing liquid feedstock 20 from a clarified PAC-containing liquid feedstock supply 10 is fed to a UF feed tank 30.
  • the clarified PAC-containing liquid feedstock in the UF feed tank is then pumped to a UF membrane system 40 ⁇ using a Koch Membrane Systems model # 3838K328-NYT spiral wound UF membrane with a 5000 mol. wt.
  • the continuous processing of the clarified PAC-containing liquid feedstock supply thus results in a continuous accumulation of PACs in the liquid contents of UF feed tank and UF membrane system ⁇ the aggregate PAC-enriched retentate stream ⁇ .
  • the aggregate PAC-enriched retentate stream can then be diafiltered with water 110 to further increase the PAC dry weight, content of the liquid extract through the systematic removal of residual lower molecular weight soluble solids ⁇ e.g., sugars, acids, etc. ⁇ as permeate.
  • the aggregate PAC-enriched liquid retentate 120 ⁇ with a PAC dry wt. content of at least 5%, 10%, 15%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 90% ⁇ is collected in a PAC- enriched retentate holding tank 130, and sequentially pumped to a concentrator 140 then a dryer 150.
  • the resultant product constituting a PAC-enriched extract powder is finally transferred to a PAC-enriched bulk powder storage container 160.
  • a suitable ultrafilter for use in the methods of the invention can have a molecular weight cutoff of about 2,000-10,000 Dalton, about 3,000 Dalton, about 4000 Dalton, about 5000 Dalton, about 6000 Dalton, about 7000 Dalton, about 8000 Dalton, or about 9000 Dalton on propylene glycol.
  • These undissolved solids can include higher molecular weight PACs and/or aggregates of lower molecule weight PACs.
  • These undissolved solids can be separated from liquid in which the are suspended by centrifugation using, for example, a decanter centrifuge or a disk centrifuge.
  • PAC-reduced permeate by utilizing resin technology (e.g., employing Amberlite® XAD7HP or Amberlite® TM FPX66 resin) to selectively remove and recover anthocyanins and/or phenolic compounds as another phytochemically distinct extract fraction(s).
  • resin technology e.g., employing Amberlite® XAD7HP or Amberlite® TM FPX66 resin
  • This fraction can be combined with a fraction that is relatively high in PACs, e.g., the PAC-enriched retentate, to obtain material that is high in PACs, anthocyanins and/or phenolic compounds and relatively low in sugars and acids.
  • PACs e.g., the PAC-enriched retentate
  • the system may be operated in batch, modified batch or feed and bleed mode under variable temperature, pressure and flow conditions.
  • the system may contain membranes in configurations other than spiral wound (i.e. tubular or hollow fiber), of varying polymer composition (for example PTFE, PVDF, etc.) or inorganic membrane structures with varied composition (for example ceramic, carbon, or stainless steel etc.) and support media.
  • membranes other than ultrafiltration membranes may be employed such as reverse osmosis or nanofiltration membranes or charged membranes or charge- specific membranes may be employed in any manner previously described.
  • controlled atmosphere e.g., N 2 or CO 2
  • Different diafiltration media e.g., acidified water
  • Countercurrently extracted fruit juice can be prepared as described in U.S. Patent Nos. 5,320,861 and 5,419,251 , hereby incorporated by reference. Briefly, frozen whole raw cranberries are provided to a cleaning stage to remove debris such as twigs, leaves, etc. and then conveyed to a sorting stage which sorts fruit to a selected size. The size-selected fruit is then conveyed to a slicing stage that slices the berries to expose the inner flesh of the fruit, unprotected by the skin. The whole cranberries are preferably cut to provide slices between 6 to 8 millimeters in width.
  • the cleaned, sized and sliced frozen cranberries are then defrosted using hot water (e.g., at about 130°F) to a temperature of less than 75°F (e.g., 65°F) and conveyed to the solid input of an extractor stage which employs a countercurrent extractor described in detail in U.S. Patent No. 5,320,861.
  • the liquid input to the extractor is typically derived from a fruit-derived water supply.
  • the liquid output of the extractor stage is a high-quality extract mixture of fruit-derived water and fruit juice, which is collected for further treatment and use in the methods of the invention.
  • the extracted fruit can be used as a fruit feed stock to produce additional juice that can be used in the methods of the invention.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Nanotechnology (AREA)
  • Preparation Of Fruits And Vegetables (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Cosmetics (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pyrane Compounds (AREA)
PCT/US2008/069294 2007-07-13 2008-07-07 Process for producing a proanthocyanidin extract Ceased WO2009012070A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2010516172A JP2010533648A (ja) 2007-07-13 2008-07-07 プロアントシアニジン抽出物を生成するためのプロセス
AU2008276266A AU2008276266A1 (en) 2007-07-13 2008-07-07 Process for producing a proanthocyanidin extract
CN200880024498A CN101796044A (zh) 2007-07-13 2008-07-07 制备原花色素提取物的方法
CA2692688A CA2692688C (en) 2007-07-13 2008-07-07 Process for producing a proanthocyanidin extract
EP08781419.0A EP2175731A4 (en) 2007-07-13 2008-07-07 PROCESS FOR PREPARING A PROANTHOCYANIDINE EXTRACT

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US94960407P 2007-07-13 2007-07-13
US60/949,604 2007-07-13

Publications (1)

Publication Number Publication Date
WO2009012070A1 true WO2009012070A1 (en) 2009-01-22

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/069294 Ceased WO2009012070A1 (en) 2007-07-13 2008-07-07 Process for producing a proanthocyanidin extract

Country Status (7)

Country Link
US (3) US9023413B2 (https=)
EP (1) EP2175731A4 (https=)
JP (1) JP2010533648A (https=)
CN (1) CN101796044A (https=)
AU (1) AU2008276266A1 (https=)
CA (1) CA2692688C (https=)
WO (1) WO2009012070A1 (https=)

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US20110059193A1 (en) * 2008-05-05 2011-03-10 Tournay Biotechnologies, Sas Method for obtaining an extract of cranberry marc that can be used in particular in the prevention and treatment of conditions such as caries, gingivitis or sore throats
CN103509834A (zh) * 2013-10-16 2014-01-15 合肥工业大学 一种高生物利用度蓝莓花青素的制备方法
EP2797436A4 (en) * 2012-01-01 2015-11-25 Kambouris Gillian Anne PLANT BASED BEVERAGES AND MANUFACTURING METHOD THEREFOR
US10709751B2 (en) 2014-05-30 2020-07-14 Shaklee Corporation Chardonnay grape seed extract
EP4578916A1 (en) * 2011-06-30 2025-07-02 E. & J. Gallo Winery Natural crystalline colorant and process for production

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PL2792254T3 (pl) * 2009-04-16 2017-06-30 Ocean Spray Cranberries, Inc. Ekstrakcja związków fenolowych i ich zastosowanie w kompozycjach z kwasem fumarowym
WO2011088420A1 (en) * 2010-01-15 2011-07-21 Ocean Spray Cranberries, Inc. Process for extracting compound from cranberry leaves and related products
US9215885B2 (en) * 2010-09-16 2015-12-22 Ocean Spray Cranberries, Inc. Sequential extraction process
US8404293B2 (en) * 2010-09-23 2013-03-26 Graceland Fruit, Inc. Method for separating and concentrating bioactive phenolics
US9107447B2 (en) 2011-10-12 2015-08-18 Ocean Spray Cranberries, Inc. Xyloglucan extraction process
MX387797B (es) * 2014-05-30 2025-03-19 Shaklee Corp Extracto de semilla de uva chardonnay.
CN104592011B (zh) * 2015-02-13 2016-05-11 宁波杰顺生物科技有限公司 一种蔓越莓中奎宁酸提取物的制备方法
CN104840508B (zh) * 2015-05-22 2019-03-19 南京林业大学 黑荆树叶提取物及其制备方法与应用
CN105294636B (zh) * 2015-11-16 2018-11-27 大兴安岭林格贝寒带生物科技股份有限公司 一种制备低聚原花青素的方法
TW201919491A (zh) * 2017-08-31 2019-06-01 美商優鮮沛蔓越莓公司 整合性水果之浸漬、萃取及酸移除
CN108191805A (zh) * 2018-03-06 2018-06-22 云南华测检测认证有限公司 一种从重瓣玫瑰中提取天然原花青素的方法
EP3860361B1 (en) * 2018-10-02 2022-04-13 West Invest S.A. Process for producing purified pac`s and sugar from fruit juice, and compositions comprising same
US20240324643A1 (en) * 2023-03-27 2024-10-03 E. & J. Gallo Winery Grape seed extracts and related systems and methods of manufacture

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110059193A1 (en) * 2008-05-05 2011-03-10 Tournay Biotechnologies, Sas Method for obtaining an extract of cranberry marc that can be used in particular in the prevention and treatment of conditions such as caries, gingivitis or sore throats
EP4578916A1 (en) * 2011-06-30 2025-07-02 E. & J. Gallo Winery Natural crystalline colorant and process for production
EP3936574B1 (en) * 2011-06-30 2025-10-29 E. & J. Gallo Winery Natural crystalline colorant derived from purple carrot
EP4659848A3 (en) * 2011-06-30 2026-04-08 E. & J. Gallo Winery Natural crystalline colorant derived from purple carrot
EP2797436A4 (en) * 2012-01-01 2015-11-25 Kambouris Gillian Anne PLANT BASED BEVERAGES AND MANUFACTURING METHOD THEREFOR
CN103509834A (zh) * 2013-10-16 2014-01-15 合肥工业大学 一种高生物利用度蓝莓花青素的制备方法
CN103509834B (zh) * 2013-10-16 2015-07-08 合肥工业大学 一种高生物利用度蓝莓花青素的制备方法
US10709751B2 (en) 2014-05-30 2020-07-14 Shaklee Corporation Chardonnay grape seed extract

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US9226520B2 (en) 2016-01-05
US20090035432A1 (en) 2009-02-05
CA2692688A1 (en) 2009-01-22
JP2010533648A (ja) 2010-10-28
US9420812B2 (en) 2016-08-23
US20150313267A1 (en) 2015-11-05
US9023413B2 (en) 2015-05-05
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US20150208700A1 (en) 2015-07-30

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