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WO1998003480A1 - PROCEDE DE RECUPERATION DE β-CAROTENE CRISTALLIN A PARTIR D'UNE SOURCE NATURELLE - Google Patents

PROCEDE DE RECUPERATION DE β-CAROTENE CRISTALLIN A PARTIR D'UNE SOURCE NATURELLE Download PDF

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Publication number
WO1998003480A1
WO1998003480A1 PCT/EP1997/003961 EP9703961W WO9803480A1 WO 1998003480 A1 WO1998003480 A1 WO 1998003480A1 EP 9703961 W EP9703961 W EP 9703961W WO 9803480 A1 WO9803480 A1 WO 9803480A1
Authority
WO
WIPO (PCT)
Prior art keywords
carotene
crystals
solvent
crude
preparation
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/EP1997/003961
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English (en)
Inventor
Mieke Sibeyn
Robertus Mattheus De Pater
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.)
DSM Delft BV
Original Assignee
Gist Brocades BV
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 Gist Brocades BV filed Critical Gist Brocades BV
Priority to AU36961/97A priority Critical patent/AU3696197A/en
Priority to JP10506580A priority patent/JP2000515742A/ja
Priority to EP97933695A priority patent/EP0912506A1/fr
Publication of WO1998003480A1 publication Critical patent/WO1998003480A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P23/00—Preparation of compounds containing a cyclohexene ring having an unsaturated side chain containing at least ten carbon atoms bound by conjugated double bonds, e.g. carotenes
    • 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

  • the present invention relates to the field of the recovery of carotenoids from a natural source.
  • ⁇ - carotene crystals with a high purity (96% or higher) are produced by chemical synthesis.
  • ⁇ - carotene mostly is in the form of an oily extract (palm oil, algal oil) .
  • -5-carotene crystals from natural sources, such as vegetables (for example carrots) or micro-organisms (for example algae (Dunaliella) or fungi [Blakeslea)
  • the currently available processes to obtain relatively pure crystals from said natural sources have important disadvantages.
  • Current processes for the purification of ff-carotene crystals from a natural source typically comprise an extraction step and additional purification steps.
  • organic solvents such as ethyl acetate, butyl acetate or hexane
  • vegetable oils such as ethyl acetate, butyl acetate or hexane
  • supercritical fluids such as propane, ethylene, CO 2 .
  • ?-carotene preparation a further purification of the extract is necessary.
  • Several purification processes have been described, among which chromatography, adsorption/desorption processes and crystallization or precipitation.
  • the ?-carotene crystals which are directly crystallized from the extract obtained after solvent extraction of a suitable natural source, e.g . by evaporation of the solvent, typically do not have the desired high purity, e.g . a purity compared to that of synthetic ?-carotene. In such cases recrystallizations are required (NL 641 1 1 84, US 4,439, 629) .
  • the present invention discloses a process for the preparation of ⁇ - carotene crystals with a purity of at least 90% from a natural source. Said process comprises the following steps:
  • the ⁇ -carotene extract obtained after solvent extraction of a natural source is washed with water prior to crystallization of /?-carotene.
  • the method of the invention provides a crystalline ?-carotene preparation from a natural source with a purity of > 95% .
  • the method of the invention can be conveniently used to increase the ⁇ - carotene content of any impure crystalline S-carotene preparation. Detailed description of the invention
  • the present invention discloses a process for the recovery of highly pure yS-carotene crystals from a natural source with a high yield.
  • highly pure ?-carotene crystals are recovered from crude /?-carotene crystals using a simple and convenient solvent treatment.
  • the process of the invention comprises a treatment of a crude / ff-carotene crystal preparation with a solvent in which J-carotene has a low solubility.
  • the crude ?-carotene crystals which are subjected to the process of the invention are obtained by conventional extraction and crystallization technology.
  • the extraction of -5-carotene from a natural source is carried out with organic solvents, vegetable oils or supercritical fluids.
  • the subsequent crystallization or precipitation is performed by methods as cooling, evaporation of the solvent or addition of an antisolvent, followed by filtering off the crystals.
  • the /J-carotene content of the crude crystals mainly depends on the natural source which is used for isolation, whereas the applied crystallization procedure additionally can influence the same. Typically, said ⁇ S-carotene content varies between 60 and 90% .
  • the solvent treatment of the crude crystals according to the invention significantly increases the ?-carotene content of the crystals.
  • the crystals obtained after solvent treatment have a /?-carotene content of > 90%, preferably a ?-carotene content of > 92%, more preferably a ?-carotene content of > 94% .
  • crude ?-carotene crystals are treated with a solvent in which ff-carotene has a low solubility.
  • the solvent treatment of the invention comprises the steps of stirring the crude ?-carotene crystals in said solvent during a time period sufficient to enable dissolution of impurities, filtering off the crystals and washing the crystals several times with fresh solvent. Optionally, the treatment is repeated one or more times. After the final washing step, residual solvent is evaporated.
  • Solvents which are suitable to use in the treatment according to the mvention are solvents in which ff-carotene has a low solubility, i.e. a solubility of at most 1 g/l at 25 °C.
  • the solvent is water or an organic solvent.
  • the pH of the water is not a critical factor for the treatment of the invention, although it is preferred that the pH is below 7. More preferably, the pH of the water is 4-6.
  • the organic solvent preferably is a lower alcohol or a lower acyl ester thereof, wherein lower is understood to comprise a straight or branched chain of 1 to 5 carbon atoms, or acetone. More preferably, the organic solvent is ethanol or ethylacetate.
  • the solvent in which ⁇ -carotene has a low solubility is applied in a sufficient amount to remove a substantial amount of impurities.
  • the solvent to crystal ratio is > 5 ml solvent per gram crystal, more preferably > 5- 1 0 ml per gram crystal, most preferably 20-40 ml per gram crystal . It is understood that the upper limit of the volume of solvent per gram crystals is not a technical limit but is determined by economical criteria.
  • the time which is necessary for dissolution of the impurities in the solvent is dependent on the temperature at which the stirring is performed .
  • the stirring is performed at a temperature below the boiling point of the solvent.
  • the stirring is performed at a temperature of 20 to
  • the solubility of ?-carotene in the solvent which is used also may influence the temperature of the stirring process.
  • the stirring preferably is performed at an elevated temperature, e.g. 50°C, whereas when using a solvent in which 9-carotene has a relatively high solubility, e.g . ethylacetate, the stirring temperature may be choosen in the lower range, e.g . 20 to 25 °C.
  • a stirring temperature at a more elevated level, e.g. 50 °C, and to cool the mixture after stirring to a lower temperature, e.g. a temperature of 5 to 20 ° C, to prevent relatively high losses of ⁇ -carotene.
  • a suitable stirring time is for instance about 30 minutes.
  • the present invention also envisages the option to subsequently treat crude ⁇ -carotene crystals with two or more different solvents in which ⁇ - carotene has a low solubility.
  • the amount of water used is not very critical, although it may be relevant to choose said amount such that a good phase separation is obtained .
  • the present invention provides a simple and convenient method to increase the ?-carotene content of ⁇ -carotene crystals.
  • the solvent treatment of the invention is advantageously applied to any crystalline ⁇ -carotene preparation obtainable from a natural source (plant or a microbial), of which the purity is not as high as desired.
  • the method of the present invention is applicable to a crude crystal preparation of a natural carotenoid other than ?-carotene.
  • the method of the invention is applied to /?-carotene crystals obtainable from a microbial source, more preferably from algae or fungi (including yeasts), even more preferably from fungi of the order Mucorales, most preferably from Blakeslea trispora.
  • a microbial source more preferably from algae or fungi (including yeasts), even more preferably from fungi of the order Mucorales, most preferably from Blakeslea trispora.
  • highly pure, natural ⁇ - carotene crystals are obtainable from microbial biomass, e.g . from Blakeslea trispora.
  • Said highly pure, natural, crystalline ?-carotene preparation has a purity of > 95 %, preferably > 96% , more preferably > 97%, even more preferably > 98%, most preferably > 99% .
  • Due to the natural origin of the highly pure, crystalline ⁇ -carotene preparation said preparation may also contain a small amount of other carotenoids, such as -/-carotene.
  • the content of y-carotene thereby may vary from about 0.5 to about 1 .5% .
  • a preferred process comprises the steps of washing an ethylacetate extract obtained from Blakeslea trispora with water prior to crystallization, crystallization of ?-carotene from said washed extract to obtain crude crystals and subsequent treatment of said crude crystals with two different solvents, i.e. firstly with ethylacetate and secondly with ethanol, both solvent treatments occurring at a temperature of 50 °C.
  • the method of the invention enables the manufacture of a crystalline -5-carotene preparation from a natural source which has an extremely high purity, i.e. a purity which is not obtained using conventional technology, i.e. a purity which is > 95% .
  • the highly purified ?-carotene crystals obtained by the process of the invention are suitable for food, pharmaceutical and cosmetic applications.
  • the natural ⁇ -carotene crystals typically are applied as a oily suspension, e.g . a 30% (w/v) suspension of crystals in a vegetable oil, such as soybean oil.
  • the ?-carotene content of crystals is analyzed spectrophotometrically (FCC Ill/Monographs) or with proton-NMR.
  • Example 1 The extract obtained in Example 1 was concentrated to a S-carotene concentration of 1 2 g/l by evaporating the solvent at 50°C under vacuum.
  • the concentrate was cooled to 20 °C and kept at 20°C during 2 hours under stirring.
  • the crystals were filtered and washed with two cake-volumes of ethyl acetate, yielding 0.7 gram of crude crystal with a purity of 91 .9% .
  • Subsequently the dried crude crystals were stirred for 30 minutes in 35 ml of ethanol at 50°C. After cooling to room temperature, the crystals were filtered off, washed with 2 cake volumes of ethanol and dried under vacuum at room temperature. 0.65 gram of crystals with a purity of 97.0% were obtained.
  • An extract containing 1 .7 g/l of ?-carotene was prepared as described in Example 1 .
  • This extract was concentrated to a ?-carotene concentration of 1 0 g/l by evaporating the solvent at 50°C under vacuum.
  • the concentrate was cooled to 5 °C and kept at 5 °C during two hours under stirring .
  • the crystals were filtered and washed with two cake-volumes of ethyl acetate, yielding 0.8 gram of crude crystal with a purity of 94.1 % .
  • Example 4 The extract obtained in Example 4 was concentrated to a ?-carotene concentration of 1 0 g/l by evaporating the solvent at 50°C under vacuum. The concentrate was cooled to 5 °C and kept at 5 ° C during 2 hours under stirring.
  • the ethyl acetate extract was subsequently mixed with demineralized water of 50 °C in a volumetric ratio of 1 0/1 (extract/water) . After stirring during 1 5 minutes at 50°C, the layers were separated. The ethyl acetate layer was then concentrated to a ?-carotene content of 6 g/l by evaporation .
  • the concentrate was cooled to 5 °C, causing crystallization of ⁇ - carotene. After two hours at 5°C under stirring, the crystals were filtered and washed with two cake volumes of ethyl acetate, yielding 6.4 kg of wet crystals (dry matter 60.2%) .
  • the wet crystals were stirred in 75 I of ethanol at
  • the concentrate was cooled to 5 °C, causing crystallization of ⁇ - carotene. After two hours at 5 °C under stirring, the crystals were filtered and washed with two cake volumes of ethyl acetate, yielding 24 kg of wet crystals (dry matter 55%) .
  • the wet crystals were subsequently stirred in 450 I of ethyl acetate at 50°C during 30 minutes.
  • the suspension was then allowed to cool to 5 ° C, the crystals were filtered and subsequently washed with two cake volumes of ethyl acetate and finally one cake volume of ethanol. 23 kg of wet crystals were obtained. Next the crystals were stirred in 450 I of ethanol (95 %) at 50°C during

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Procédé permettant de récupérer des cristaux de β-carotène extrêmement purs à partir d'une préparation de cristaux bruts obtenue à partir d'une source naturelle. Pour enlever les impuretés, on remue les cristaux bruts dans un solvant dans lequel le β-carotène présente une faible solubilité, puis on récupère les cristaux par filtrage et on les lave avec du solvant neuf. Le procédé de la présente invention permet d'obtenir une préparation cristalline naturelle de β-carotène à pureté extrêmement élevée, comparable à celle du β-carotène synthétique.
PCT/EP1997/003961 1996-07-19 1997-07-18 PROCEDE DE RECUPERATION DE β-CAROTENE CRISTALLIN A PARTIR D'UNE SOURCE NATURELLE Ceased WO1998003480A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU36961/97A AU3696197A (en) 1996-07-19 1997-07-18 Process for the recovery of crystalline beta-carotene from natural source
JP10506580A JP2000515742A (ja) 1996-07-19 1997-07-18 天然原料からの結晶β―カロチンの回収方法
EP97933695A EP0912506A1 (fr) 1996-07-19 1997-07-18 PROCEDE DE RECUPERATION DE $g(b)-CAROTENE CRISTALLIN A PARTIR D'UNE SOURCE NATURELLE

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
EP96202035 1996-07-19
EP96202035.0 1996-07-19
EP96202334.7 1996-08-22
EP96202334 1996-08-22
EP96202852 1996-10-15
EP96202852.8 1996-10-15

Publications (1)

Publication Number Publication Date
WO1998003480A1 true WO1998003480A1 (fr) 1998-01-29

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PCT/EP1997/003961 Ceased WO1998003480A1 (fr) 1996-07-19 1997-07-18 PROCEDE DE RECUPERATION DE β-CAROTENE CRISTALLIN A PARTIR D'UNE SOURCE NATURELLE

Country Status (4)

Country Link
EP (1) EP0912506A1 (fr)
JP (1) JP2000515742A (fr)
AU (1) AU3696197A (fr)
WO (1) WO1998003480A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998050574A1 (fr) * 1997-05-02 1998-11-12 Dsm N.V. Isolement de cristaux carotenoides a partir d'une biomasse microbienne
DE19821009A1 (de) * 1998-05-11 1999-11-18 Siegfried Peter Verfahren zur Extraktion von Carotinen aus Fetten und Ölen biologischen Ursprungs
RU2152929C1 (ru) * 1999-07-12 2000-07-20 Открытое акционерное общество "Белгородвитамины" СПОСОБ ОЧИСТКИ ТЕХНИЧЕСКОГО β-КАРОТИНА
WO2001012832A1 (fr) * 1999-08-12 2001-02-22 Vitatene, S.A. Procede pour l'obtention de lycopene
GB2358862A (en) * 1999-12-21 2001-08-08 Fermentron Ltd Extracting carotenoids
WO2002010429A1 (fr) * 2000-07-19 2002-02-07 Vitatene, S.A. Procede de production de $g(b)-carotene
WO2002004415A3 (fr) * 2000-07-12 2002-05-10 Univ Maryland Procede de purification et de cristallisation de carotenoides d'huile palmitique
JP2003520847A (ja) * 2000-01-27 2003-07-08 デーエスエム・ナムローゼ・フェンノートシャップ カロテノイド結晶の単離
WO2003056028A1 (fr) 2001-12-31 2003-07-10 Vitatene, S.A. Procede ameliore de production de lycopene par fermentation de souches selectionnees de blakeslea trispora, formulations et utilisations du lycopene obtenu
EP1480936A4 (fr) * 2001-07-19 2004-12-22 Ranbaxy Lab Ltd Procede servant a preparer acitretine
WO2004063359A3 (fr) * 2003-01-09 2005-01-27 Basf Ag Procede pour realiser des carotinoides ou leur precurseurs au moyen d'organismes genetiquement modifies de l'espece blakeslea, carotinoide ou precurseurs obtenus selon ce procede et utilisation associee
US7173145B2 (en) 2001-11-29 2007-02-06 University Of Maryland, College Park Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants
US7438412B2 (en) 2000-01-03 2008-10-21 Novartis Ag Colored contact lens with a more natural appearance
WO2011145113A2 (fr) 2010-05-17 2011-11-24 Dynadis Biotech India Pvt Ltd Procédé de production de cristaux de bêta-carotène et de lycopène de haute pureté à partir de biomasse fongique
EP2017262B1 (fr) * 2006-03-28 2015-08-19 Nippon Oil Corporation Procede de production de carotenoide
EP3351596A1 (fr) * 2011-06-30 2018-07-25 E. & J. Gallo Winery Colorant cristallin naturel et procédé de production

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4969370B2 (ja) 2007-08-29 2012-07-04 Ｊｘ日鉱日石エネルギー株式会社 カロテノイドの製造方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3268606A (en) * 1963-09-27 1966-08-23 Upjohn Co Beta-carotene process
GB1064645A (en) * 1963-07-19 1967-04-05 Basf Ag Production in pure form of compounds of the carotenoid and vitamin-a series
CN1092063A (zh) * 1993-03-04 1994-09-14 孙景茂 从胡萝卜中提取天然β胡萝卜素的工艺

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1064645A (en) * 1963-07-19 1967-04-05 Basf Ag Production in pure form of compounds of the carotenoid and vitamin-a series
US3268606A (en) * 1963-09-27 1966-08-23 Upjohn Co Beta-carotene process
CN1092063A (zh) * 1993-03-04 1994-09-14 孙景茂 从胡萝卜中提取天然β胡萝卜素的工艺

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 9716, Derwent World Patents Index; AN 97-166034, XP002044040, "Extracting natural beta-carotene from carrot" *

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6812001B2 (en) 1997-05-02 2004-11-02 Dsm N.V. Isolation of carotenoid crystals from microbial biomass
WO1998050574A1 (fr) * 1997-05-02 1998-11-12 Dsm N.V. Isolement de cristaux carotenoides a partir d'une biomasse microbienne
US6407306B1 (en) 1998-05-11 2002-06-18 Siegfried Peter Process for extracting carotenes from carotene-containing materials
DE19821009A1 (de) * 1998-05-11 1999-11-18 Siegfried Peter Verfahren zur Extraktion von Carotinen aus Fetten und Ölen biologischen Ursprungs
WO1999058611A3 (fr) * 1998-05-11 2000-03-16 Siegfried Peter Procede d'extraction de carotenes de matieres contenant de la carotene
RU2152929C1 (ru) * 1999-07-12 2000-07-20 Открытое акционерное общество "Белгородвитамины" СПОСОБ ОЧИСТКИ ТЕХНИЧЕСКОГО β-КАРОТИНА
WO2001012832A1 (fr) * 1999-08-12 2001-02-22 Vitatene, S.A. Procede pour l'obtention de lycopene
ES2157166A1 (es) * 1999-08-12 2001-08-01 Antibioticos Sau Procedimiento para la obtencion de licopeno.
GB2358862A (en) * 1999-12-21 2001-08-08 Fermentron Ltd Extracting carotenoids
US6818239B2 (en) 1999-12-21 2004-11-16 Fermentron Ltd. Processes for extracting carotenoids and for preparing feed materials
GB2358862B (en) * 1999-12-21 2004-07-21 Fermentron Ltd Processes for Extracting Carotenoids from Biomass Carotenoid Sources
US7438412B2 (en) 2000-01-03 2008-10-21 Novartis Ag Colored contact lens with a more natural appearance
US7015014B2 (en) 2000-01-27 2006-03-21 Dsm Ip Assets B.V. Isolation of carotenoid crystals
JP2003520847A (ja) * 2000-01-27 2003-07-08 デーエスエム・ナムローゼ・フェンノートシャップ カロテノイド結晶の単離
WO2002004415A3 (fr) * 2000-07-12 2002-05-10 Univ Maryland Procede de purification et de cristallisation de carotenoides d'huile palmitique
US7119238B2 (en) 2000-07-12 2006-10-10 University Of Maryland Process for purification and crystallization of palm oil carotenoids
WO2002010429A1 (fr) * 2000-07-19 2002-02-07 Vitatene, S.A. Procede de production de $g(b)-carotene
ES2168971A1 (es) * 2000-07-19 2002-06-16 Antibioticos Sau Procedimiento de produccion de beta-caroteno.
US8859228B2 (en) 2000-07-19 2014-10-14 Dsm Ip Assets B.V. Method for the production of beta-carotene
US7129365B2 (en) 2001-07-19 2006-10-31 Ranbaxy Laboratories Limited Process for the preparation of acitretin
EP1480936A4 (fr) * 2001-07-19 2004-12-22 Ranbaxy Lab Ltd Procede servant a preparer acitretine
US7173145B2 (en) 2001-11-29 2007-02-06 University Of Maryland, College Park Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants
WO2003056028A1 (fr) 2001-12-31 2003-07-10 Vitatene, S.A. Procede ameliore de production de lycopene par fermentation de souches selectionnees de blakeslea trispora, formulations et utilisations du lycopene obtenu
EP2143800A1 (fr) 2001-12-31 2010-01-13 Vitatene, S.A. Formulations de lycopène et utilisations associées
WO2004063359A3 (fr) * 2003-01-09 2005-01-27 Basf Ag Procede pour realiser des carotinoides ou leur precurseurs au moyen d'organismes genetiquement modifies de l'espece blakeslea, carotinoide ou precurseurs obtenus selon ce procede et utilisation associee
EP2017262B1 (fr) * 2006-03-28 2015-08-19 Nippon Oil Corporation Procede de production de carotenoide
WO2011145113A2 (fr) 2010-05-17 2011-11-24 Dynadis Biotech India Pvt Ltd Procédé de production de cristaux de bêta-carotène et de lycopène de haute pureté à partir de biomasse fongique
WO2011145113A3 (fr) * 2010-05-17 2012-01-19 Dynadis Biotech India Pvt Ltd Procédé de production de cristaux de bêta-carotène et de lycopène de haute pureté à partir de biomasse fongique
US9682932B2 (en) 2010-05-17 2017-06-20 Dynadis Biotech India Private Limited Process for production of high purity beta-carotene and lycopene crystals from fungal biomass
EP3351596A1 (fr) * 2011-06-30 2018-07-25 E. & J. Gallo Winery Colorant cristallin naturel et procédé de production

Also Published As

Publication number Publication date
JP2000515742A (ja) 2000-11-28
EP0912506A1 (fr) 1999-05-06
AU3696197A (en) 1998-02-10

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