WO2010058235A1 - Procédé de préparation d'oxycaroténoïdes - Google Patents

Procédé de préparation d'oxycaroténoïdes Download PDF

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Publication number
WO2010058235A1
WO2010058235A1 PCT/IB2008/003141 IB2008003141W WO2010058235A1 WO 2010058235 A1 WO2010058235 A1 WO 2010058235A1 IB 2008003141 W IB2008003141 W IB 2008003141W WO 2010058235 A1 WO2010058235 A1 WO 2010058235A1
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WO
WIPO (PCT)
Prior art keywords
accordance
zeaxanthin
astaxanthin
although
oxidation
Prior art date
Application number
PCT/IB2008/003141
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English (en)
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WO2010058235A8 (fr
Inventor
Danilo Vizcarra Gonzales
Mario David Torres Cardona
Original Assignee
Innova Andina S.A.
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.)
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Publication date
Application filed by Innova Andina S.A. filed Critical Innova Andina S.A.
Priority to JP2011536957A priority Critical patent/JP2012509307A/ja
Priority to MX2011005264A priority patent/MX2011005264A/es
Priority to CN2008801319854A priority patent/CN102272098A/zh
Priority to PCT/IB2008/003141 priority patent/WO2010058235A1/fr
Priority to PE2009001252A priority patent/PE20100745A1/es
Priority to CL2009002105A priority patent/CL2009002105A1/es
Publication of WO2010058235A1 publication Critical patent/WO2010058235A1/fr
Publication of WO2010058235A8 publication Critical patent/WO2010058235A8/fr

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • 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

Definitions

  • Astaxanthin occurs naturally in different seaweed, bacteria, fungi and some animals, frequently forming some type of complex with proteins; also in plants such as the Adonis annua L. and also found in some birds, such as flamingoes, quails, and other species. In addition it can be found in its free form or as a mono- or di-ester derivative.
  • This carotenoid has generally been used for the pigmentation of some salmonids that do not synthesize it de novo, which confers the pink tonalities that the market prefers. It has also found applications in the pigmentation of crustaceans, although in these its immunostimulant and antioxidant activities have been most appreciated; this affects their health remarkably and therefore lead to better survival rates when they are cultivated intensively.
  • Other oxicarotenoids like canthaxanthin, echinenone and adonixanthin, are actually used for the same purposes. It has been demonstrated that astaxanthin exhibits anti-oxidant activity superior to that of most carotenoids (J. Agric. Food Chem. 48, 1150) and thus it is also currently being used successfully for human consumption.
  • the potent antioxidant property of astaxanthin has been implicated in its various biological activities demonstrated in both experimental animals and clinical studies. Astaxanthin has considerable potential and promising applications in human health and nutrition. The most significant activities of astaxanthin, includes its antioxidative and anti-inflammatory properties, its effects on cancer, diabetes, the immune system and ocular health, the promotion of human health, including the antihypertensive and neuroprotective potentials and the effects of dietary astaxanthin on blood pressure, stroke, and vascular dementia (J Nat Prod., 69,443).
  • Synthetic astaxanthin is an identical molecule to that produced in living organisms and it consists of a mixture 1:2:1 of isomers (3S,3S ' ), (3R,3R') and (3R.3R) respectively.
  • the process described herein includes an additional step, which consists of protecting the zeaxanthin's hydroxyl groups first, and then proceeding with a step of simultaneous de-protection and oxidation that, under the technique mentioned, produces a high yield of astaxanthin including the usage of a catalyst and a phase transfer agent for the oxidation step improvement. If the protecting groups step is omitted then echinenone, adonixanthin and other carotenoids are obtained.
  • Zeaxanthin Some of the major natural sources (Sajilata et al.) for obtaining zeaxanthin as a raw material for the process that is described herein are yellow corn, orange pepper, orange juice, honeydew, mango, genetically altered marigolds and chicken egg yolk. Zeaxanthin comprise about 90% of the total carotenoids in the anthers of Delonix regia (GuI Mohr) flowers. Zeaxanthin is also the major carotenoid in cold-pressed marionberry, boysenberry, red raspberry, and blueberry seed oils. Zeaxanthin has also been identified in extracts from apricots, peaches, cantaloupe, and a variety of pink grapefruit (Ruby seedless).
  • Flavobacterium sp. is reported to produce zeaxanthin as essentially its only carotenoid.
  • the pigment formed by Flavobacterium consists of 95% to 99% zeaxanthin.
  • Flavobacterium produced zeaxanthin is identical to zeaxanthin from Zea mays.. Erwinia herbicola, a nonphotosynthetic bacterium, is yellow-colored due to accumulation of polar carotenoids, primarily mono- and diglucosides of zeaxanthin.
  • the green alga Neospongiococcum excentricum is shown to produce up to 0.65% xanthophylls (dry mass ,basis).
  • a zeaxanthin-overproducing mutant strain zea 7 generated from Dunaliella salina may be considered for commercial exploitation.
  • Zeaxanthin is a natural constituet of the outer membrane of Synechocystis sp. PCC6714 .
  • the microalgae Microcystis aeruginosa is reported to produce the bioactive carotenoid zeaxanthin.
  • the blue-green alga Spirulina has zeaxanthin as one of its carotenoids.
  • Zeaxanthinibacter enoshimensis is a zeaxanthin-producing marine bacterium of the family Flavobacteriaceae, isolated from the seawater off Enoshima island in Japan.
  • Mesoflavibacter zeaxanthinifaciens is another novel zeaxanthin-producing marine bacterium of the family Flavobacteriaceae.
  • the carotenoids of the red algae Corallina officinalis, C. elongate, and Jania sp. are reportedly composed of /3-carotene, zeaxanthin, fucoxanthin, 9_-c/sfucoxanthin, fucoxanthinol, 9_-c/s-fucoxanthinol, and 2 epimeric mutatoxanthins.
  • Prochloron sp. , and Pleurochloris commutata are some of the other microbial sources of zeaxanthin.
  • zeaxanthin prepared synthetically. It is composed of trans- zeaxanthin and minor quantities of c/s-zeaxanthin, 12 ' -apo-zeaxanthinal, diatoxanthin, and parasiloxanthin.
  • the zeaxanthin prepared by synthetic processes suffer from several disadvantages; they typically require numerous reaction steps, and each step has a less than 100% yield, so that the final yield of zeaxanthin at the end of the multistep processing tends to be relatively poor.
  • chemical synthesis tends to yield undesirable S-S and S-
  • Lutein from natural sources is usually accompanied by (3R,3'R)-zeaxanthin and always has the (3R, 3'R, 6'R) chirality and zeaxanthin prepared from lutein necessarily has the
  • the present invention describes the utilization of silyl ethers as protective groups for zeaxanthin, such as -O-Si(CH 3 ) 3 , -O-Si(CH 2 -CH 3 )3, -O-Si(isopropyl) 3 , -O- Si(CH 2 CH 3 ) 2 (isopropyl), -O-Si(CH 3 ) 2 (tert-butyl), -O-Si(CH 3 ) 2 (n-hexyl), etc.
  • the protective groups can be converted by hydrolysis into a hydroxyl group again.
  • silyl derivatives are put under a process of de-protection and oxidation by which, in a single step procedure, the astaxanthin is produced in high yield if a catalyst and a phase transfer agent are used.
  • Some of the preferred oxidation systems are iodobenzoic acid, nickel peroxide, the Jones reagent, the Collins reagent, pyridinium chlorochromate (PCC), bipyridinium chlorochromate, benzyl-trimethyl-ammonium chlorochromate, pyridinium fluorochromate, pyridinium dichromate, trimethylsilyl chlorochromate, chromic acid, HOBr, HOCI, N-bromosuccinimide, hypochlorites like tert-butyl hypochlorite, sodium or calcium hypochlorite, tetrabutylammonium hypochlorite, N-chlorosuccinimide, perchlorates, bromates, chlorates, iodates and periodates, manganese dioxide, potassium permanganate, 2,3-dichloro-5,6-di-cyanoquinone, p-chloranil, silver oxide, silver carbonate, lead tetraacetate
  • TMS-O trimethylsiloxy
  • terf-butyldiphenyl - triethyl -
  • tert- butyldimethylsiloxy triethyl -
  • commercial silylating equivalent mixtures have been preferred for protecting the hydroxyls in zeaxanthin.
  • the process is carried out under very soft reaction conditions with temperatures that range from -30 0 C to room temperature, and in the presence of a halogenated catalyst such as salts of iodine and bromine; selenium dioxide, vanadium pentoxide and osmium tetraoxide, eerie ammonium nitrate, eerie sulphate, ruthenium tetroxide, ruthenium trichloride or mixtures thereof, which are also appropriate.
  • a halogenated catalyst such as salts of iodine and bromine; selenium dioxide, vanadium pentoxide and osmium tetraoxide, eerie ammonium nitrate, eerie sulphate, ruthenium tetroxide, ruthenium trichloride or mixtures thereof, which are also appropriate.
  • a fundamental objective of this invention is to provide a procedure for obtaining astaxanthin with yields of 70 % or greater from zeaxanthin, so that it is possible to have a product economically more accessible and of equal quality compared to those that are now circulating in the world market.
  • the astaxanthin thus prepared is useful in aquaculture, poultry farming and as a nutraceutic in human consumption; mainly in the pigmentation of salmonids, crustaceans and other aquatic species.
  • Another objective of this invention is to provide a procedure to obtain several oxicarotenoids like adonixanthin, ⁇ -cryptoxanthin and canthaxanthin when isozeaxanthin is used.
  • Scheme 1 shows how the transformation of zeaxanthin to astaxanthin takes place when its hydroxyl groups are protected.
  • the zeaxanthin used may be 100 % pure or in the form of a product that contains more than 400 g of carotenoid for each kilogram of concentrate containing more of 90 % of zeaxanthin. These normally come from natural sources, so frequently the pigment comes in a greasy matrix that does not interfere in the overall process.
  • a solvent which preferably would be pyridine, although halogenated solvents such as methylene chloride, carbon tetrachloride and chloroform are also suitable.
  • the carotenoid is made to react with trimethyl-chlorosilane or any commercial silylating mixture at room temperature.
  • the mixture that contains the zeaxanthin trimethyl-silylether will be kept under the same conditions as initially in order to continue with the process of deprotection and oxidation.
  • a minimum amount of the catalyst is added to the mixture from the reaction previously described and then the pyridinium chloro-chromate, which is the oxidant that is preferred, is added.
  • the mixture of pigment with solvent is shaken vigorously in a sealed reactor so that the inner atmosphere can be controlled, whether in atmospheric conditions or in the absence of oxygen.
  • the temperature of the process is kept between -30 0 C and room temperature or between -15 0 C and 15 0 C, although it is preferable to carry it out between 0 0 C and 10 0 C, both in its group protection stage and in its oxidation stage.
  • the catalyst is used in amounts that range from 0.1 to 2 % of the weight of pigment, although it is preferable to use from 0.5 to 1.0 %, previously dissolved in a portion of the solvent. In the case of oxidant, up to 10 parts of this have been used to each part of zeaxanthin, although it is preferable to use between 3 and 5 parts of oxidant to each part of carotenoid.
  • the phase transfer agent is used in amounts that range from 0.01 % to 1 % of the weight of xanthophylls. Both the group protection and the oxidation stage are carried out with between 15 min and 5 hours of reaction, although under favorable conditions it is possible to carry it out in between 1 and 3 hours.
  • the protective or silylant agent is used in the amount of 10 parts to each part of zeaxanthin, although it is preferable to use 3 to 6 parts.
  • the organic phase is decanted and washing twice with aqueous bicarbonate 2 % first then with deionized water.
  • 100 mg of alpha-tocopherol, 50 mg of BHT and 100 ml of soy oil are added to the organic phase, then it is evaporated to recover the solvent and an oil suspension of astaxanthin containing 50 g of the pigment per kilogram.
  • the suspension is homogenizated using an Ultra Turrax (IKA T-25) homogenizer obtaining a xanthophylls crystals distribution size from 0.2 to 2 microns, excellent to be formulated in salmonids and crustaceans diets.
  • IKA T-25 Ultra Turrax
  • the solid residue is washed with 50 milliliters of additional pyridine and the washing is joined with the decanting, proceeding to discard the residual solid.
  • the organic phase is evaporated to recover the solvent and then 100 milliliters of ethanol is added to the residue even with less than 10 % of pyridine and evaporation is continued until almost dryness.
  • the residue is washed with 300 milliliters of water at 40 °C acidulated with acetic acid to a pH of 4.5, discarding the wash. An additional washing takes place and again the wash is discarded.
  • the solid obtained contains around 6.1 g of astaxanthin and is mixed with 200 ml of red olein added with 150 mg of BHT, then milling (IKA colloid mill, MK 2000) until obtain a crystal size distribution from 0.2 to 2.0 microns .
  • the obtained suspension is homogenizated using an Ultra Turrax homogenizer (IKA Ultra Turrax T-25).
  • the organic phase is separated and is then washed with 200 milliliters of a watery solution of 10 % sodium thiosulfate first and then 200 milliliters of water.
  • the solvent is recovered and the residue is again dissolved in ethanol and is put under thermal isomerization while the alcohol is recovered.
  • the final residue contains around 4.1 g of astaxanthin, which represents a yield of nearly 70 %.
  • the organic phase is evaporated to recover the solvent and then 100 mililiters of ethanol is added to the residue even with less than 10 % of pyridine and evaporation is continued until almost dryness. Then the residue is washed with 300 milliliters of water at 40 0 C, discarding the wash. An additional washing takes place and again the wash is discarded.
  • the solid obtained contains around 6.1 g of canthaxanthin.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
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Abstract

La présente invention concerne un procédé à haut rendement permettant de préparer de l'astaxanthine (3,3'-dihydroxy-β,β-carotène-4,4'-dione) à partir de dérivés silylés de zéaxanthine (3,3'-dihydroxy-β,β-carotène-3,3'-diol), d'origine synthétique ou naturelle.
PCT/IB2008/003141 2008-11-19 2008-11-19 Procédé de préparation d'oxycaroténoïdes WO2010058235A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2011536957A JP2012509307A (ja) 2008-11-19 2008-11-19 オキシカロテノイドの調製方法
MX2011005264A MX2011005264A (es) 2008-11-19 2008-11-19 Metodo para la preparacion de oxicarotenoides.
CN2008801319854A CN102272098A (zh) 2008-11-19 2008-11-19 氧基类胡萝卜素的制备方法
PCT/IB2008/003141 WO2010058235A1 (fr) 2008-11-19 2008-11-19 Procédé de préparation d'oxycaroténoïdes
PE2009001252A PE20100745A1 (es) 2008-11-19 2009-11-16 Metodo para la preparacion de oxicarotenoides
CL2009002105A CL2009002105A1 (es) 2008-11-19 2009-11-18 Metodo de preparacion de astaxantina a partir de zeaxantina mediante proteccion de los grupos hidroxilos y posterior oxidacion y desproteccion del producto obtenido.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2008/003141 WO2010058235A1 (fr) 2008-11-19 2008-11-19 Procédé de préparation d'oxycaroténoïdes

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WO2010058235A1 true WO2010058235A1 (fr) 2010-05-27
WO2010058235A8 WO2010058235A8 (fr) 2011-07-28

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PCT/IB2008/003141 WO2010058235A1 (fr) 2008-11-19 2008-11-19 Procédé de préparation d'oxycaroténoïdes

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CN (1) CN102272098A (fr)
CL (1) CL2009002105A1 (fr)
MX (1) MX2011005264A (fr)
PE (1) PE20100745A1 (fr)
WO (1) WO2010058235A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102250148A (zh) * 2011-05-17 2011-11-23 北京理工大学 一种相转移氧化剂的制备方法
JP2013023475A (ja) * 2011-07-21 2013-02-04 Toho Earthtech Inc １，３−ジヨードヒダントイン類の製造方法
WO2015067706A1 (fr) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Procédé de purification de l'astaxanthine
WO2015067711A1 (fr) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Procédé de purification d'astaxanthine
WO2015067703A1 (fr) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Procédé pour la purification d'astaxanthine
WO2015067705A1 (fr) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Procédé de purification d'astaxanthine
WO2015067707A1 (fr) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Procédé de purification d'astaxanthine
CN106831520A (zh) * 2017-04-13 2017-06-13 山东天音生物科技有限公司 一种由玉米黄质制备虾青素的方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585885A (en) * 1982-08-20 1986-04-29 Hoffmann-La Roche Inc. Cyclohexenone derivatives and process for making same
EP1253131A1 (fr) * 2001-04-24 2002-10-30 Aventis Animal Nutrition S.A. Procédé de préparation de xanthophylles
ES2223270A1 (es) * 2003-04-10 2005-02-16 Carotenoid Technologies, S.A. Procedimiento para la sintesis de astaxantina.
ES2299304A1 (es) * 2005-07-29 2008-05-16 Carotenoid Technologies, S.A. Procedimiento para la preparacion de astaxantina.

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585885A (en) * 1982-08-20 1986-04-29 Hoffmann-La Roche Inc. Cyclohexenone derivatives and process for making same
EP1253131A1 (fr) * 2001-04-24 2002-10-30 Aventis Animal Nutrition S.A. Procédé de préparation de xanthophylles
ES2223270A1 (es) * 2003-04-10 2005-02-16 Carotenoid Technologies, S.A. Procedimiento para la sintesis de astaxantina.
ES2299304A1 (es) * 2005-07-29 2008-05-16 Carotenoid Technologies, S.A. Procedimiento para la preparacion de astaxantina.

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102250148A (zh) * 2011-05-17 2011-11-23 北京理工大学 一种相转移氧化剂的制备方法
JP2013023475A (ja) * 2011-07-21 2013-02-04 Toho Earthtech Inc １，３−ジヨードヒダントイン類の製造方法
WO2015067706A1 (fr) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Procédé de purification de l'astaxanthine
WO2015067711A1 (fr) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Procédé de purification d'astaxanthine
WO2015067703A1 (fr) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Procédé pour la purification d'astaxanthine
WO2015067705A1 (fr) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Procédé de purification d'astaxanthine
WO2015067707A1 (fr) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Procédé de purification d'astaxanthine
CN106831520A (zh) * 2017-04-13 2017-06-13 山东天音生物科技有限公司 一种由玉米黄质制备虾青素的方法

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Publication number Publication date
CN102272098A (zh) 2011-12-07
CL2009002105A1 (es) 2010-07-02
MX2011005264A (es) 2011-08-03
PE20100745A1 (es) 2010-10-28
JP2012509307A (ja) 2012-04-19
WO2010058235A8 (fr) 2011-07-28

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