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WO1999020587A8 - Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants - Google Patents

Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants

Info

Publication number
WO1999020587A8
WO1999020587A8 PCT/US1998/022229 US9822229W WO9920587A8 WO 1999020587 A8 WO1999020587 A8 WO 1999020587A8 US 9822229 W US9822229 W US 9822229W WO 9920587 A8 WO9920587 A8 WO 9920587A8
Authority
WO
WIPO (PCT)
Prior art keywords
lutein
zeaxanthin
plants
carotenoids
berries
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/US1998/022229
Other languages
French (fr)
Other versions
WO1999020587A1 (en
Inventor
Frederick Khachik
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.)
OFFICE OF TECHNOLOGY LIAISON
TECHNOLOGY LIAISON OFF OF
Original Assignee
OFFICE OF TECHNOLOGY LIAISON
TECHNOLOGY LIAISON OFF OF
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 OFFICE OF TECHNOLOGY LIAISON, TECHNOLOGY LIAISON OFF OF filed Critical OFFICE OF TECHNOLOGY LIAISON
Priority to AU12719/99A priority Critical patent/AU1271999A/en
Priority to US09/529,815 priority patent/US6262284B1/en
Publication of WO1999020587A1 publication Critical patent/WO1999020587A1/en
Publication of WO1999020587A8 publication Critical patent/WO1999020587A8/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0096—Purification; Precipitation; Filtration
    • 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
    • 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
    • A23L5/44—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 using carotenoids or xanthophylls
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

A process for simultaneously extracting, saponifying, and isolating lutein and zeaxanthin, and a mixture of several rare carotenoids in high purity from plants without the use of harmful organic solvents. Lutein crystals containing 5 % zeaxanthin were obtained from the dried petals of Marigold flowers Tagete erecta while zeaxanthin was isolated and purified from the berries of Lycium Chinese Mill (LCM berries). Similarly, this process has been employed to isolate and purify a mixture of lutein, beta-carotene, neoxanthin, violaxanthin, and lutein epoxide from green plants, preferably, kale, collard green, and spinach. These plants, to a lesser extent, also serve as a source of several rare carotenoids such as alpha-cryptoxanthin (Marigolds) and beta-cryptoxanthin (LCM berries). The purified carotenoids isolated by this process are free from impurities and serve as a safe source of nutritional supplement for human consumption as well as providing a suitable and effective color additive for human foods.
PCT/US1998/022229 1997-10-21 1998-10-21 Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants Ceased WO1999020587A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU12719/99A AU1271999A (en) 1997-10-21 1998-10-21 Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants
US09/529,815 US6262284B1 (en) 1998-10-21 1998-10-21 Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US6257297P 1997-10-21 1997-10-21
US60/062,572 1997-10-21
US7836098P 1998-03-18 1998-03-18
US60/078,360 1998-03-18

Publications (2)

Publication Number Publication Date
WO1999020587A1 WO1999020587A1 (en) 1999-04-29
WO1999020587A8 true WO1999020587A8 (en) 1999-08-26

Family

ID=26742423

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/022229 Ceased WO1999020587A1 (en) 1997-10-21 1998-10-21 Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants

Country Status (2)

Country Link
AU (1) AU1271999A (en)
WO (1) WO1999020587A1 (en)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6191293B1 (en) 1998-04-20 2001-02-20 Inexa, Industria Extractora C.A. Trans-xanthophyll ester concentrates of enhanced purity and methods of making same
CA2396167C (en) 2000-01-27 2010-01-26 Dsm N.V. Isolation of carotenoid crystals
US6818798B1 (en) 2000-05-03 2004-11-16 University Of Maryland, College Park Process for making a (3R,3′R)-zeaxanthin precursor
US6329557B1 (en) 2000-06-09 2001-12-11 Prodemex, S.A. De C.V. Purification of xanthophylls from marigold extracts that contain high levels of chlorophylls
US7119238B2 (en) 2000-07-12 2006-10-10 University Of Maryland Process for purification and crystallization of palm oil carotenoids
DE60108879T2 (en) 2000-07-27 2006-04-06 University Of Maryland College Park PROCESS FOR THE PREPARATION OF RARE CAROTINOIDES BASED ON TRADING LUTINE
JP2002218994A (en) * 2001-01-26 2002-08-06 Fuji Chem Ind Co Ltd Purification of crude xanthophylls
WO2002060864A1 (en) * 2001-01-30 2002-08-08 Sabinsa Corporation Process of obtaining compositions of stable lutein and lutein derivatives
US6784351B2 (en) * 2001-06-29 2004-08-31 Ball Horticultural Company Targetes erecta marigolds with altered carotenoid compositions and ratios
US7575766B2 (en) * 2001-06-29 2009-08-18 Ball Horticultural Company Tagetes erecta with altered carotenoid compositions and ratios
WO2003048284A1 (en) 2001-11-29 2003-06-12 University Of Maryland Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants
CA2474646C (en) 2002-02-06 2011-04-26 University Of Maryland, College Park Method for production of .beta.-cryptoxanthin and .alpha.-cryptoxanthin from commercially available lutein
US6737535B2 (en) 2002-06-05 2004-05-18 Kancor Flavours And Extracts Limited Trans-lutein enriched xanthophyll ester concentrate and a process for its preparation
EP1371641A1 (en) * 2002-06-10 2003-12-17 Adisseo France S.A.S. Process for the formation and isolation of carotenoid crystals
US6743953B2 (en) 2002-08-26 2004-06-01 Kancor Flavours & Extracts Ltd. Process for the preparation of xanthophyll crystals
US7351424B2 (en) 2004-07-22 2008-04-01 Bio Lut S.A. De C.V. Enhanced purity trans-lutein-ester compositions and methods of making same
EP1974049A2 (en) 2004-12-17 2008-10-01 Metanomics GmbH Process for the control of production of fine chemicals
ATE483684T1 (en) * 2005-04-25 2010-10-15 Katra Phytochem Private Ltd ISOLATION AND PURIFICATION OF CAROTENOIDS FROM MARIGOLD FLOWERS
CN100368395C (en) * 2006-05-17 2008-02-13 浙江医药股份有限公司新昌制药厂 Method for separating and purifying high-content lutein fatty acid ester from marigold oleoresin
CN101402597A (en) * 2008-10-31 2009-04-08 南京泛成生物化工有限公司 Xanthophyll extraction process
CN102174005A (en) * 2011-01-25 2011-09-07 石河子大学医学院第一附属医院 Method for extracting lutein from marigold dried flowers
TWI466709B (en) * 2011-07-20 2015-01-01 Nat Univ Chung Hsing From the original berry Wolfberry a liquid - liquid freezing method for separation of high purity theaflavins palmitate Maize
CN102558008A (en) * 2011-09-08 2012-07-11 黑龙江省嘉宝生物技术开发有限公司 Preparation method for lutein
CN103091446B (en) * 2013-01-31 2015-12-23 甘肃省农垦农业研究院 Lutein ester saponification degree rapid assay methods
CN103275088A (en) * 2013-05-30 2013-09-04 湖南炎帝生物工程有限公司 Method for separating chlorophyll a and carotinoid from nostoc
CN104803901A (en) * 2014-01-27 2015-07-29 中国科学院大连化学物理研究所 Method for preparing zeaxanthin through in situ enrichment
CN103992256B (en) * 2014-05-17 2016-09-07 昆明涞章医药科技有限公司 A kind of method preparing high-purity lutein ester from pot marigold
CN105503681A (en) * 2014-09-25 2016-04-20 赵军 Preparation method of high purity Chinese wolfberry zeaxanthin palmitate
CN104447467A (en) * 2014-10-30 2015-03-25 蒋小春 Method for extracting carotenoid from lycium chinense
CN105017116A (en) * 2015-07-31 2015-11-04 江西恩泉油脂有限公司 Saponifying technique of lutein extract
CN107082756B (en) * 2017-03-17 2018-11-23 晨光生物科技集团股份有限公司 A kind of industrial production process of lutein crystal
CN114401775B (en) * 2019-07-26 2023-11-07 卡利亚里大学 Isolation of color body carotenoids from fruits
CN110563625B (en) * 2019-09-29 2020-07-31 山东天音生物科技有限公司 Method for separating and purifying zeaxanthin from marigold oleoresin
CN110835315A (en) * 2019-10-28 2020-02-25 百瑞源枸杞股份有限公司 Preparation method of lycium ruthenicum red pigment
KR102161387B1 (en) * 2019-12-09 2020-09-29 대한켐텍 주식회사 A composition comprising lutein for improving skin condition and a fuctional food comprising the composition

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4048203A (en) * 1976-12-06 1977-09-13 Thomas Philip Purification of lutein-fatty acid esters from plant materials
US5382714A (en) * 1994-03-17 1995-01-17 The Catholic University Of America Process for isolation, purification, and recrystallization of lutein from saponified marigold oleoresin and uses thereof
US5648564A (en) * 1995-12-21 1997-07-15 Kemin Industries, Inc. Process for the formation, isolation and purification of comestible xanthophyll crystals from plants

Also Published As

Publication number Publication date
WO1999020587A1 (en) 1999-04-29
AU1271999A (en) 1999-05-10

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