WO2009063100A1 - Extraction of carotenoids using a single-phase ternary blend of ethanol:hexane:water. - Google Patents
Extraction of carotenoids using a single-phase ternary blend of ethanol:hexane:water. Download PDFInfo
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- WO2009063100A1 WO2009063100A1 PCT/ES2007/000683 ES2007000683W WO2009063100A1 WO 2009063100 A1 WO2009063100 A1 WO 2009063100A1 ES 2007000683 W ES2007000683 W ES 2007000683W WO 2009063100 A1 WO2009063100 A1 WO 2009063100A1
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- extraction
- carotenoids
- hexane
- solvents
- carotenoid
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0288—Applications, solvents
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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
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- 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
Definitions
- the presented invention can be applied to any process of separation and purification of carotenoids from any raw material, such as the extraction of beta-carotene from plant matter and / or microalgae, or lutein from flowers of
- the object of the present invention is a method of extracting carotenoids ("carotenes” as defined in Order SCO / 4223/2004) by using a biocompatible ternary mixture ethanol-water-hexane as an extractant.
- This composition can be varied within certain margins while retaining its effectiveness. extractor, as seen in the triangular diagram of composition, being important that the mixture of the three solvents form a single homogeneous phase.
- the use of the proposed ternary mixture is applicable to any raw material, and is based on biocompatible solvents.
- the method consists in the use of a ternary mixture of solvents in a single phase, which, when brought into contact with the raw material in an appropriate manner, quantitatively extracts the carotenoids present therein.
- the proposed method solves the problem of the use of complex extraction systems for the recovery of carotenoids from animal and / or plant biomass, such as hexane extraction in multiple contact in countercurrent.
- the methods currently available for the proposed purpose involve handling large amounts of solvent and large equipment per unit of product due to the low efficiency of the solvents used.
- this extractive phase provides a high recovery of carotenoids, up to 100%, in a wide range of operating conditions, and has a high selectivity towards these substances, allowing to obtain extracts of carotenoids with few impurities and very concentrated in these substances.
- the proposed ternary mixture can be applied to any current extraction process with carotenoid solvents, without it being necessary to greatly modify the extraction process itself, but significantly improving yields by increasing the amount of product obtained per unit of matter used premium
- the invention therefore, can be applied in both the chemical and food, nutraceutical and / or pharmacological industries.
- the present invention can be included in the field of the processes of extraction of compounds intended for food that are included in current Spanish legislation.
- the present invention consists of a carotenoid extraction process by employing a single phase composed of ethanol, hexane and water, applicable to a wide range of materials containing these carotenoids, which has been successfully tested in microalgae, and which is applicable to any conveniently disintegrated material containing these substances.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the extraction of carotenoids using ternary blends. An extracting blend for separating out carotenoids has been developed, which can be used with any raw material, based on biocompatible solvents. The invention comprises the use of a single-phase ternary blend of solvents which, when placed in contact with the raw material in a suitable manner, quantitatively extracts the carotenoids contained therein. The proposed invention solves the problem of the use of complex extraction systems for the recovery of carotenoids from animal and/or plant biomass, such as extraction with hexane in countercurrent multiple contact. The solvents currently used for the stated purpose do not dissolve the compounds of interest very well, so that it is necessary to use high quantities of solvent and equipment of great size per product unit due to the poor efficiency of the solvents used.
Description
Extracción de carotenoides mediante el uso de la mezcla ternaria en una sola fase de etanol:hexano:agua. Carotenoid extraction by using the ternary mixture in a single phase of ethanol: hexane: water.
Sector de la técnicaTechnical sector
5 La invención presentada se puede aplicar a cualquier proceso de separación y purificación de carotenoides a partir de cualquier materia prima, tales como la extracción de betacaroteno a partir de materia vegetal y/o microalgas, o de luteina a partir de flores deThe presented invention can be applied to any process of separation and purification of carotenoids from any raw material, such as the extraction of beta-carotene from plant matter and / or microalgae, or lutein from flowers of
10 caléndula y/o microalgas. Actualmente se comercializan diversos tipos de carotenoides como los mencionados anteriormente tanto para su uso en acuicultura, como alimentación animal, e incluso nutracéutica y/o farmacología. La invención presentada, al ser aplicada a10 marigold and / or microalgae. Various types of carotenoids are currently marketed, such as those mentioned above, both for use in aquaculture, as animal feed, and even nutraceutical and / or pharmacology. The invention presented, when applied to
15 estos procesos extractivos permite mejorar los rendimientos de extracción y reducir por tanto el coste de los mismos.15 These extractive processes make it possible to improve extraction yields and therefore reduce their cost.
Estado de la técnicaState of the art
20 El objeto de la presente invención es un método de extracción de carotenoides ("carotenos" según definición recogida en la Orden SCO/4223/2004) mediante el uso de una mezcla ternaria biocompatible etanol-agua-hexano como agente extractante. Esta composición puede variarse 5 dentro de ciertos márgenes conservando su eficacia
extractora, como se observa en el diagrama triangular de composición, siendo lo importante que la mezcla de los tres disolventes forme una única fase homogénea.The object of the present invention is a method of extracting carotenoids ("carotenes" as defined in Order SCO / 4223/2004) by using a biocompatible ternary mixture ethanol-water-hexane as an extractant. This composition can be varied within certain margins while retaining its effectiveness. extractor, as seen in the triangular diagram of composition, being important that the mixture of the three solvents form a single homogeneous phase.
El empleo de la mezcla ternaria propuesta es aplicable a cualquier materia prima, y está basado en disolventes biocompatibles. El método consiste en la utilización de una mezcla ternaria de disolventes en una única fase, que puesta en contacto con la materia prima de forma adecuada, extrae de forma cuantitativa los carotenoides presentes en la misma. El método propuesto resuelve el problema del uso de complejos sistemas de extracción para la recuperación de carotenoides de biomasa animal y/o vegetal, tales como extracción con hexano en contacto múltiple en contracorriente. Los métodos existentes actualmente para el fin planteado implican el manejo de elevadas cantidades de disolvente y equipos de gran tamaño por unidad de producto debido a la baja eficiencia de los disolventes utilizados. La utilización de esta fase extractora proporciona una elevada recuperación de carotenoides, de hasta el 100%, en una amplia gama de condiciones de operación, y presenta como ventaja una elevada selectividad hacia estas sustancias, permitiendo obtener unos extractos de
carotenoides con pocas impurezas y muy concentrados en estas sustancias.The use of the proposed ternary mixture is applicable to any raw material, and is based on biocompatible solvents. The method consists in the use of a ternary mixture of solvents in a single phase, which, when brought into contact with the raw material in an appropriate manner, quantitatively extracts the carotenoids present therein. The proposed method solves the problem of the use of complex extraction systems for the recovery of carotenoids from animal and / or plant biomass, such as hexane extraction in multiple contact in countercurrent. The methods currently available for the proposed purpose involve handling large amounts of solvent and large equipment per unit of product due to the low efficiency of the solvents used. The use of this extractive phase provides a high recovery of carotenoids, up to 100%, in a wide range of operating conditions, and has a high selectivity towards these substances, allowing to obtain extracts of carotenoids with few impurities and very concentrated in these substances.
Actualmente los procesos utilizados se basan en el uso de disolventes orgánicos como hexano o etanol, en forma de compuestos puros, o bien en el uso de compuestos en estado supercritico, como C02 supercritico, a elevadas presiones. En ambos casos resulta dificil modificar la capacidad extractante de dichas fases por lo que los rendimientos de recuperación de producto son reducidos. El uso de la mezcla ternaria propuesta permite ajustar la polaridad de la fase extractante de forma que se incrementa la solubilidad en ella de compuestos de interés como los carotenoides, incrementando de forma notable los rendimientos de extracción. Las mezcla ternaria propuesta puede ser aplicada a cualquier proceso actual de extracción con disolventes de carotenoides, sin que sea necesario modificar en gran medida el proceso de extracción en si, pero mejorando de forma notable los rendimientos aumentando la cantidad de producto obtenida por unidad de materia prima utilizada. La invención, por tanto, puede ser aplicada tanto en la industria química como alimentaria, nutraceutica y/o farmacológica.
La presente invención se puede englobar en el campo de los procesos de extracción de compuestos con destino a alimentación que se encuentran recogidos en la legislación española vigente. En concreto, se pueden citar como antecedentes los disolventes de extracción permitidos para carotenoides (mencionados como "carotenos en los textos legales") recogidos en la Orden SCO/4223/2004 de 16 de Diciembre, que modifica a la SCO/1052/2002 de 7 de Mayo, al RD 2107/1996 y al RD 2001/1995 de 7 de Diciembre en la que se recogen hexano y etanol como disolventes permitidos, entre otros fines, para la recuperación de "carotenos" (ElβOa) incluyendo licopeno (E160d) , luteína (E161b) y cantaxantina (Elβlg) de plantas y de algas (anexo en la Orden SCO/4223/2004) .Currently the processes used are based on the use of organic solvents such as hexane or ethanol, in the form of pure compounds, or on the use of compounds in a supercritical state, such as supercritical CO2, at high pressures. In both cases it is difficult to modify the extractant capacity of these phases, so the product recovery yields are reduced. The use of the proposed ternary mixture allows the polarity of the extractant phase to be adjusted so that the solubility in it of compounds of interest such as carotenoids is increased, notably increasing the extraction yields. The proposed ternary mixture can be applied to any current extraction process with carotenoid solvents, without it being necessary to greatly modify the extraction process itself, but significantly improving yields by increasing the amount of product obtained per unit of matter used premium The invention, therefore, can be applied in both the chemical and food, nutraceutical and / or pharmacological industries. The present invention can be included in the field of the processes of extraction of compounds intended for food that are included in current Spanish legislation. Specifically, the extraction solvents allowed for carotenoids (mentioned as "carotenes in legal texts") included in Order SCO / 4223/2004 of December 16, which modifies SCO / 1052/2002 of May 7, to RD 2107/1996 and RD 2001/1995 of December 7 in which hexane and ethanol are collected as solvents allowed, among other purposes, for the recovery of "carotenes" (ElβOa) including lycopene (E160d) , lutein (E161b) and cantaxanthin (Elβlg) of plants and algae (annexed in Order SCO / 4223/2004).
Estos disolventes son también utilizados para la extracción de carotenoides a partir de restos de crustáceos, etc. Estos disolventes son usados por separado en etapas sucesivas. Resulta difícil encontrar referencias en bibliografía a procesos de extracción de carotenoides de aplicación industrial, refiriéndose en la inmensa mayoría de los trabajos publicados a extracciones destinadas a técnicas analíticas.
Descripción de la invenciónThese solvents are also used for the extraction of carotenoids from crustacean remains, etc. These solvents are used separately in successive stages. It is difficult to find references in the literature for carotenoid extraction processes of industrial application, referring in the vast majority of published works to extractions for analytical techniques. Description of the invention
La presente invención consiste en un proceso de extracción de carotenoides mediante el empleo de una fase única compuesta por etanol, hexano y agua, aplicable a una amplia gama de materiales que contienen estos carotenoides, que ha sido ensayada con éxito en microalgas, y que es aplicable a cualquier material convenientemente disgregado que contenga estas sustancias.The present invention consists of a carotenoid extraction process by employing a single phase composed of ethanol, hexane and water, applicable to a wide range of materials containing these carotenoids, which has been successfully tested in microalgae, and which is applicable to any conveniently disintegrated material containing these substances.
La extracción de carotenoides y otras sustancias liposolubles viene realizándose con la utilización de diversos disolventes como fase extractora entre los que cabe destacar el hexano. Sin embargo, la baja solubilidad de algunas de estas sustancias en hexano obliga a realizar extracciones múltiples, que conllevan el contacto reiterado del material de extracción y del hexano (extractante) lo que conlleva una elevada utilización de disolvente y una complicación del equipo. Esto es especialmente importante en el caso de los carotenoides y particularmente en el caso de carotenoides oxigenados como la luteina o zeaxantina, que pueden requerir hasta 10 etapas de contacto para una extracción completa con hexano.
El procedimiento descrito consigue mediante la utilización de la fase propuesta una recuperación de carotenoides muy elevada, y que en el caso de la luteina y zeaxantina en una única etapa de extracción con la fase descrita se consigue una recuperación de las sustancias de interés equivalente a 8 etapas de extracción con hexano.The extraction of carotenoids and other fat-soluble substances has been carried out with the use of various solvents as an extractor phase, among which hexane can be highlighted. However, the low solubility of some of these substances in hexane makes it necessary to perform multiple extractions, which entail repeated contact with the extraction material and hexane (extractant), which leads to a high use of solvent and a complication of the equipment. This is especially important in the case of carotenoids and particularly in the case of oxygenated carotenoids such as lutein or zeaxanthin, which may require up to 10 contact stages for complete extraction with hexane. The procedure described achieves a very high recovery of carotenoids through the use of the proposed phase, and that in the case of lutein and zeaxanthin in a single extraction stage with the described phase, a recovery of substances of interest equivalent to 8 is achieved. extraction stages with hexane.
Breve descripción de los dibujos A continuación se pasa a describir de manera breve un modo de realización de la invención, como ejemplo ilustrativo y no limitativo de ésta. Para una mejor comprensión del modo de realización, se incluye la figura 1: Diagrama triangular para el sistema etanol-hexano - aguaBRIEF DESCRIPTION OF THE DRAWINGS The following briefly describes an embodiment of the invention, as an illustrative and non-limiting example thereof. For a better understanding of the embodiment, Figure 1 is included: Triangular diagram for the ethanol-hexane-water system
Descripción de una realización preferidaDescription of a preferred embodiment
La invención ahora será descrita, por la manera del ejemplo, como medios de la ilustración y no han de ser interpretados como limitativos.The invention will now be described, by way of example, as means of the illustration and should not be construed as limiting.
Ejemplo 1:Example 1:
Asi, para la extracción de los carotenoides contenidos en 1 kg de biomasa seca de microalgas basta
con tomar la biomasa y molturarla adecuadamente, añadirleThus, for the extraction of the carotenoids contained in 1 kg of dry biomass of microalgae it is enough with taking the biomass and grinding it properly, add
10 L de la mezcla monofásica compuesta por etanol-hexano- agua en proporciones de 77:17:6, mezclarlo de forma adecuada durante 5 minutos para maximizar el contacto entre las fases, y finalmente decantar el material biológico para retirar el sobrenadante con más del 90% de los carotenoides contenidos en la biomasa. La mezcla monofásica utilizada puede ser llevada a sequedad para obtener finalmente un concentrado de carotenoides, o bien ser sometida posteriormente a procesos de extracción con otros disolventes o incluso procesos cromatográficos para purificar de toda la mezcla de carotenoides uno o varios de ellos en concreto.
10 L of the single-phase mixture composed of ethanol-hexane-water in proportions of 77: 17: 6, mix it properly for 5 minutes to maximize the contact between the phases, and finally decant the biological material to remove the supernatant with more than 90% of the carotenoids contained in the biomass. The monophasic mixture used can be taken to dryness to finally obtain a carotenoid concentrate, or be subsequently subjected to extraction processes with other solvents or even chromatographic processes to purify one or several of them in particular from the entire carotenoid mixture.
Claims
1.- Extracción de carotenoides mediante el uso de mezclas ternarias caracterizado por una sola fase compuesta por etanolrhexano ragua1.- Extraction of carotenoids through the use of ternary mixtures characterized by a single phase composed of ragua ethanol rhexane
2.- Extracción de carotenoides mediante el uso de mezclas ternarias según reivindicación 1 caracterizado por utilizar etanol y hexano para que se forme con el agua de constitución del material que va a ser extraído una fase extractante2. Carotenoid extraction by using ternary mixtures according to claim 1 characterized by using ethanol and hexane to form with the water of constitution of the material to be extracted an extractant phase
3.- Extracción de carotenoides mediante el uso de mezclas ternarias según reivindicación 1 y 2 caracterizado por extraer carotenoides específicos como la luteina, zeaxantina, betacaroteno, astaxantina, violaxantina, asi como de sus esteres, de cualquier material3. Carotenoid extraction by using ternary mixtures according to claim 1 and 2 characterized by extracting specific carotenoids such as lutein, zeaxanthin, beta-carotene, astaxanthin, violaxanthin, as well as their esters, from any material
4.- Extracción de carotenoides mediante el uso de mezclas ternarias según reivindicaciones 1-3 caracterizado porque la extracción se realiza a partir de biomasa animal y vegetal4. Carotenoid extraction by using ternary mixtures according to claims 1-3 characterized in that the extraction is carried out from animal and plant biomass
5.- Extracción de carotenoides mediante el uso de mezclas ternarias según reivindicaciones 1-3 caracterizado porque la extracción se realiza a partir de biomasa animal 5.- Extraction of carotenoids through the use of ternary mixtures according to claims 1-3 characterized in that the extraction is carried out from animal biomass
6.- Extracción de carotenoides mediante el uso de mezclas ternarias según reivindicaciones 1-3 caracterizado porque la extracción se realiza a partir de biomasa vegetal6. Extraction of carotenoids through the use of ternary mixtures according to claims 1-3 characterized in that the extraction is carried out from plant biomass
7.- Extracción de carotenoides mediante el uso de mezclas ternarias según reivindicaciones 1-3 caracterizado mezcla monofásica compuesta por etanol- hexano-agua en proporciones de 77:17:67. Carotenoid extraction by using ternary mixtures according to claims 1-3 characterized by a single-phase mixture composed of ethanol-hexane-water in proportions of 77: 17: 6
8.- Uso de la extracción de carotenoides según reivindicaciones 1-7, para fines industriales8. Use of carotenoid extraction according to claims 1-7, for industrial purposes
9.- Uso de la extracción de carotenoides según reivindicaciones 1-7, para fines alimentarios9. Use of carotenoid extraction according to claims 1-7, for food purposes
10.- Uso de la extracción de carotenoides según reivindicaciones 1-7, para fines nutracéuticos10. Use of carotenoid extraction according to claims 1-7, for nutraceutical purposes
11,- Uso de la extracción de carotenoides según reivindicaciones 1-7, para fines farmacológicos 11, - Use of carotenoid extraction according to claims 1-7, for pharmacological purposes
12.- Uso de la extracción de carotenoides según reivindicaciones 1-9, para fines nutracéuticos12. Use of carotenoid extraction according to claims 1-9, for nutraceutical purposes
13.- Uso de la extracción de carotenoides según reivindicaciones 1-9, para fines farmacológicos 13.- Use of carotenoid extraction according to claims 1-9, for pharmacological purposes
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200703145A ES2319950B1 (en) | 2007-11-13 | 2007-11-13 | CAROTENOID EXTRACTION THROUGH THE USE OF TERNARY MIXTURES. |
| ESP200703145 | 2007-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2009063100A1 true WO2009063100A1 (en) | 2009-05-22 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/ES2007/000683 WO2009063100A1 (en) | 2007-11-13 | 2007-11-13 | Extraction of carotenoids using a single-phase ternary blend of ethanol:hexane:water. |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES2319950B1 (en) |
| WO (1) | WO2009063100A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2694600A1 (en) * | 2017-06-21 | 2018-12-21 | Universidad de Córdoba | Procedure for the extraction of carotenoids using nanostructured liquid phases (Machine-translation by Google Translate, not legally binding) |
| CN111153843A (en) * | 2020-01-10 | 2020-05-15 | 中国科学院兰州化学物理研究所 | Method for separating lycium barbarum pigment monomers |
| CN111153842A (en) * | 2018-11-08 | 2020-05-15 | 南京农业大学 | Method for preparing high-purity lycium barbarum zeaxanthin dipalmitate by using high-speed counter-current chromatography |
| CN111675640A (en) * | 2020-07-27 | 2020-09-18 | 中国科学院兰州化学物理研究所 | Method for separating and preparing high-purity zeaxanthin |
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| JPH0741687A (en) * | 1993-07-24 | 1995-02-10 | Food Design Gijutsu Kenkyu Kumiai | Production of concentrated natural red pigment oil for food and concentrated natural red pigment oil for food |
| US5453565A (en) * | 1990-07-20 | 1995-09-26 | Unilever Patent Holdings B.V. | Astaxanthin from flowers of the genus adonis |
| JPH09191890A (en) * | 1996-01-22 | 1997-07-29 | Kawasaki Steel Corp | Yellow pigment composition containing docosahexaenoic acid and its production |
| WO1998023567A1 (en) * | 1996-11-29 | 1998-06-04 | Cargill, Incorporated | Improved processes for recovering xanthophylls from corn gluten meal |
| WO2000013654A2 (en) * | 1998-09-04 | 2000-03-16 | I.B.R. Israeli Biotechnology Research, Ltd. | A carotenoid composition containing phytoene and phytofluene |
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- 2007-11-13 WO PCT/ES2007/000683 patent/WO2009063100A1/en active Application Filing
- 2007-11-13 ES ES200703145A patent/ES2319950B1/en active Active
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| US5453565A (en) * | 1990-07-20 | 1995-09-26 | Unilever Patent Holdings B.V. | Astaxanthin from flowers of the genus adonis |
| JPH0741687A (en) * | 1993-07-24 | 1995-02-10 | Food Design Gijutsu Kenkyu Kumiai | Production of concentrated natural red pigment oil for food and concentrated natural red pigment oil for food |
| JPH09191890A (en) * | 1996-01-22 | 1997-07-29 | Kawasaki Steel Corp | Yellow pigment composition containing docosahexaenoic acid and its production |
| WO1998023567A1 (en) * | 1996-11-29 | 1998-06-04 | Cargill, Incorporated | Improved processes for recovering xanthophylls from corn gluten meal |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2694600A1 (en) * | 2017-06-21 | 2018-12-21 | Universidad de Córdoba | Procedure for the extraction of carotenoids using nanostructured liquid phases (Machine-translation by Google Translate, not legally binding) |
| WO2018234603A1 (en) * | 2017-06-21 | 2018-12-27 | Universidad de Córdoba | Method for extracting carotenoids using nanostructured liquid phases |
| CN111153842A (en) * | 2018-11-08 | 2020-05-15 | 南京农业大学 | Method for preparing high-purity lycium barbarum zeaxanthin dipalmitate by using high-speed counter-current chromatography |
| CN111153843A (en) * | 2020-01-10 | 2020-05-15 | 中国科学院兰州化学物理研究所 | Method for separating lycium barbarum pigment monomers |
| CN111153843B (en) * | 2020-01-10 | 2021-04-13 | 中国科学院兰州化学物理研究所 | Method for separating lycium barbarum pigment monomers |
| CN111675640A (en) * | 2020-07-27 | 2020-09-18 | 中国科学院兰州化学物理研究所 | Method for separating and preparing high-purity zeaxanthin |
| CN111675640B (en) * | 2020-07-27 | 2021-06-22 | 中国科学院兰州化学物理研究所 | Method for separating and preparing high-purity zeaxanthin |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2319950A1 (en) | 2009-05-14 |
| ES2319950B1 (en) | 2010-02-15 |
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