CN101560150B - Method for extracting shikimic acid from aniseed - Google Patents

Method for extracting shikimic acid from aniseed Download PDF

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Publication number
CN101560150B
CN101560150B CN2009100396703A CN200910039670A CN101560150B CN 101560150 B CN101560150 B CN 101560150B CN 2009100396703 A CN2009100396703 A CN 2009100396703A CN 200910039670 A CN200910039670 A CN 200910039670A CN 101560150 B CN101560150 B CN 101560150B
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Prior art keywords
shikimic acid
anise
temperature
extracting
reverse osmosis
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CN101560150A (en
Inventor
哈成勇
杨少凡
哈启燊
刘新伟
沈敏敏
胡志忠
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Guangzhou Zhongke Detection Technology Service Co Ltd
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Guangzhou Institute of Chemistry of CAS
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/10—Process efficiency
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

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  • Separation Using Semi-Permeable Membranes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a method for extracting shikimic acid from aniseed. The steps are as follows: firstly, supercritical CO2 fluid is used for extracting anise oil from the aniseed; secondly, room temperature water is used for steeping the deoiled aniseed; thirdly, a reverse osmosis membrane device is used for concentrating shikimic acid extract; and the shikimic acid can be obtained after the operations of decolourization and crystallization are carried out. The method has the advantages that the process is simple and stable and is easy to control, and the extraction percentage of the shikimic acid can be more than 9 percent; by adopting the reverse osmosis membrane device for concentration, the method reduces the consumption of energy and time.

Description

A kind of method of from anise, extracting shikimic acid
Technical field
The present invention relates to chemical field, particularly a kind of method of from anise, extracting shikimic acid.
Background technology
(molecular formula is C to shikimic acid 7H 10O 5) be a kind of alcohol acid, can be used for the medicine " Tamiflu " of synthetic treatment bird flu (Tamiflu), mainly from the fruit of anise, extract.The method that tradition is extracted shikimic acid is to get dry anistree fruit, through pulverizing, uses flooding, and rotary evaporation gets medicinal extract, then goes up silicagel column, and gradient elution adds the gac boiling decoloring, filters to get filtrate, and recrystallization obtains shikimic acid.If traditional method is anistree with cold water soak, then since in the anise existence of olium anisi so that extraction efficiency is not high; If anistree with hot-water soak, then because a large amount of non-active ingredients enters extracting solution, bring difficulty to purification step; In addition, rotary evaporation also can consume a large amount of energy.
Summary of the invention
The object of the invention is to overcome the shortcoming that exists in the prior art, a kind of energy-efficient, cost is low, technique is simply extracted shikimic acid from anise method is provided.
Purpose of the present invention is achieved through the following technical solutions:
A kind of method of extracting shikimic acid from anise is to use first supercritical CO 2Olium anisi in the fluid extraction anise; Then be soaked in water and extract anise after the oil removing, obtain the shikimic acid extracting solution; Again with the concentrated shikimic acid extracting solution of reverse osmosis membrane apparatus; Obtain shikimic acid through decolouring, crystallization.
Described supercritical CO 2Olium anisi in the fluid extraction anise is first star aniseed powder to be broken to 20～80 orders before extraction; Extracting pressure is 14～24MPa, 30～45 ℃ of extraction temperature; Flash trapping stage pressure 9MPa, the flash trapping stage temperature 45 C; The second-order separation pressure cycling is pressed, the second-order separation temperature normal temperature.The highest olium anisi oil yield can reach more than 10%; Through above-mentioned supercritical CO 2The anistree powder that extracts the olium anisi processing can extract shikimic acid for the present invention.
Anise after the described extraction oil removing that is soaked in water, anise: the weight ratio of water is 1: 15～20, and soaking temperature is 15～25 ℃, and soaking number of times is 1～5 time, and each soak time is 60～180 minutes.
Described reverse osmosis membrane concentrated extracting solution, reverse osmosis membrane forefront pressure are 1～5Mpa, and 20～45 ℃ of thickening temperatures, the pH value of extracting solution are 3～4, and the shikimic acid extract yield can reach more than 9%.
The present invention adopts supercritical CO 2Olium anisi in the fluid extraction anise, on the one hand so that remove that easier being flooded of water soluble component in the anise puts forward behind the oiliness composition, can open on the other hand anistree cell walls, easier being flooded of water soluble component in the anise puts forward behind the oiliness composition so that remove, and extracts shikimic acid for cold water soak and lays the foundation.
The present invention compared with prior art has following advantage and effect:
(1) technique of the present invention simple, stablize, be easy to control, the shikimic acid extraction yield can reach more than 9%.
(2) the present invention adopts the reverse osmosis membrane apparatus concentrated extracting solution, has reduced the consumption of the energy and time.
Embodiment
Below in conjunction with embodiment the present invention is done further detailed description, but embodiments of the present invention are not limited to this.
Embodiment 1
Take by weighing the anistree 100g of the 20 orders supercritical CO of packing into 2In the fluid extraction equipment, use CO 2The equipment that is filled with is with the air in the remover apparatus.The setting extracting pressure is 14MPa, 30 ℃ of extraction temperature; Flash trapping stage pressure 9MPa, the flash trapping stage temperature 45 C; The second-order separation pressure cycling is pressed, the second-order separation temperature normal temperature; Extraction time is 120min; Olium anisi oil yield 8.5%; From supercritical CO 2Take out anistree powder after the de-oiling in the extraction equipment with 15 ℃ of Aqua pure extracts 2 times, extract 120min at every turn, liquid-solid ratio is 15: 1; United extraction liquid, concentrated with reverse osmosis membrane apparatus, concentrated condition is that the reverse osmosis membrane forefront pressure is 1Mpa, and thickening temperature is 20 ℃, and the PH of extracting solution is 3.0; Extracting solution after concentrated is through decolouring, crystallization, and the shikimic acid yield is 8.8%.
Embodiment 2
Take by weighing the anistree 500g of the 40 orders supercritical CO of packing into 2In the fluid extraction equipment, use CO 2The equipment that is filled with is with the air in the remover apparatus.The setting extracting pressure is 16MPa, 35 ℃ of extraction temperature; Flash trapping stage pressure 9MPa, the flash trapping stage temperature 45 C; The second-order separation pressure cycling is pressed, the second-order separation temperature normal temperature; Extraction time is 120min; Olium anisi oil yield 8.9%; From supercritical CO 2Take out anistree powder after the de-oiling in the extraction equipment with 15 ℃ of Aqua pure extracts 3 times, extract 90min at every turn, liquid-solid ratio is 15: 1; United extraction liquid, concentrated with reverse osmosis membrane apparatus, concentrated condition is that the reverse osmosis membrane forefront pressure is 2Mpa, and thickening temperature is 25 ℃, and the PH of extracting solution is 3.2; Extracting solution after concentrated is through decolouring, crystallization, and the shikimic acid yield is 9.1%.
Embodiment 3
Take by weighing the anistree 1000g of the 40 orders supercritical CO of packing into 2In the fluid extraction equipment, use CO 2The equipment that is filled with is with the air in the remover apparatus.The setting extracting pressure is 18MPa, 35 ℃ of extraction temperature; Flash trapping stage pressure 9MPa, the flash trapping stage temperature 45 C; The second-order separation pressure cycling is pressed, the second-order separation temperature normal temperature; Extraction time is 120min; Olium anisi oil yield 9.9%; From supercritical CO 2Take out anistree powder after the de-oiling in the extraction equipment with 20 ℃ of Aqua pure extracts 5 times, extract 60min at every turn, liquid-solid ratio is 15: 1; United extraction liquid, concentrated with reverse osmosis membrane apparatus, concentrated condition is that the reverse osmosis membrane forefront pressure is 2Mpa, and thickening temperature is 30 ℃, and the PH of extracting solution is 3.4; Extracting solution after concentrated is through decolouring, crystallization, and the shikimic acid yield is 9.2%.
Embodiment 4
Take by weighing the anistree 1500g of the 60 orders supercritical CO of packing into 2In the fluid extraction equipment, use CO 2The equipment that is filled with is with the air in the remover apparatus.The setting extracting pressure is 20MPa, 40 ℃ of extraction temperature; Flash trapping stage pressure 9MPa, the flash trapping stage temperature 45 C; The second-order separation pressure cycling is pressed, the second-order separation temperature normal temperature; Extraction time is 120min; Olium anisi oil yield 10.1%; From supercritical CO 2Take out anistree powder after the de-oiling in the extraction equipment with 20 ℃ of Aqua pure extracts 5 times, extract 60min at every turn, liquid-solid ratio is 20: 1; United extraction liquid, concentrated with reverse osmosis membrane apparatus, concentrated condition is that the reverse osmosis membrane forefront pressure is 3Mpa, and thickening temperature is 35 ℃, and the PH of extracting solution is 3.6; Extracting solution after concentrated is through decolouring, crystallization, and the shikimic acid yield is 9.1%.
Embodiment 5
Take by weighing the anistree 800g of the 60 orders supercritical CO of packing into 2In the fluid extraction equipment, use CO 2The equipment that is filled with is with the air in the remover apparatus.The setting extracting pressure is 22MPa, 45 ℃ of extraction temperature; Flash trapping stage pressure 9MPa, the flash trapping stage temperature 45 C; The second-order separation pressure cycling is pressed, the second-order separation temperature normal temperature; Extraction time is 120min; Olium anisi oil yield 9.3%; From supercritical CO 2Take out anistree powder after the de-oiling in the extraction equipment with 25 ℃ of Aqua pure extracts 4 times, extract 80min at every turn, liquid-solid ratio is 20: 1; United extraction liquid, concentrated with reverse osmosis membrane apparatus, concentrated condition is that the reverse osmosis membrane forefront pressure is 4Mpa, and thickening temperature is 40 ℃, and the PH of extracting solution is 3.8; Extracting solution after concentrated is through decolouring, crystallization, and the shikimic acid yield is 8.9%.
Embodiment 6
Take by weighing the anistree 300g of the 80 orders supercritical CO of packing into 2In the fluid extraction equipment, use CO 2The equipment that is filled with is with the air in the remover apparatus.The setting extracting pressure is 24MPa, 45 ℃ of extraction temperature; Flash trapping stage pressure 9MPa, flash trapping stage temperature 45 C the second-order separation pressure cycling is pressed, the second-order separation temperature normal temperature; Extraction time is 120min; Olium anisi oil yield 9.1%; From supercritical CO 2Take out anistree powder after the de-oiling in the extraction equipment with 25 ℃ of Aqua pure extracts 3 times, extract 90min at every turn, liquid-solid ratio is 20: 1; United extraction liquid, concentrated with reverse osmosis membrane apparatus, concentrated condition is that the reverse osmosis membrane forefront pressure is 5Mpa, and thickening temperature is 45 ℃, and the PH of extracting solution is 4.0; Extracting solution after concentrated is through decolouring, crystallization, and the shikimic acid yield is 8.8%.

Claims (2)

1. method of extracting shikimic acid from anise, it is characterized in that: (1) uses first supercritical CO 2Olium anisi in the fluid extraction anise namely is broken to star aniseed powder first 20～80 orders before extraction; Extracting pressure is 14～24MPa, 30～45 ℃ of extraction temperature; Flash trapping stage pressure 9MPa, the flash trapping stage temperature 45 C; The second-order separation pressure cycling is pressed, the second-order separation temperature normal temperature; (2) then be soaked in water and extract anise after the oil removing, obtain the shikimic acid extracting solution, wherein soaking temperature is 15～25 ℃, and soaking number of times is 1～5 time, and each soak time is 60～180 minutes, and anise: the weight ratio of water is 1: 15～20; (3) again with the concentrated shikimic acid extracting solution of reverse osmosis membrane apparatus; Obtain shikimic acid through decolouring, crystallization.
2. the method for from anise, extracting shikimic acid according to claim 1, it is characterized in that: described reverse osmosis membrane concentrated extracting solution, reverse osmosis membrane forefront pressure are 1～5MPa, 20～45 ℃ of thickening temperatures, the pH value of extracting solution is 3～4.
CN2009100396703A 2009-05-22 2009-05-22 Method for extracting shikimic acid from aniseed Expired - Fee Related CN101560150B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102010055170A1 (en) * 2010-12-20 2012-06-21 Maria Clementine Martin Klosterfrau Vertriebsgesellschaft Mbh Process for the preparation of non-alcoholic vegetable-based compositions and compositions prepared in this way and their use
CN102512532B (en) * 2011-12-15 2013-08-07 孙旭初 Medicine composition for preventing and treating diseases of quail
CN103145550A (en) * 2013-03-27 2013-06-12 张达燕 Method of extracting shikimic acid from star anise
CN109232239A (en) * 2018-09-30 2019-01-18 那坡康正天然植物提取有限责任公司 A kind of extraction process of shikimic acid
CN109485559B (en) * 2018-11-22 2022-02-11 桂林莱茵生物科技股份有限公司 Method for extracting shikimic acid from star anise
CN111233658B (en) * 2020-02-27 2022-06-07 陕西嘉禾生物科技股份有限公司 Method for extracting shikimic acid and quinic acid from folium ginkgo

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1931822A (en) * 2006-09-28 2007-03-21 广西万山香料有限责任公司 Process of extracting shikimic acid from aniseed
CN1931985A (en) * 2006-09-28 2007-03-21 广西万山香料有限责任公司 Process of extracting aniseed oil from aniseed
CN100999461A (en) * 2007-01-13 2007-07-18 红河学院 Extraction separation tech. of octagonal shickimmi oxalic acid
CN101078020A (en) * 2006-05-23 2007-11-28 曹庸 Biological transformation and purification method for illicium plants shikimic acid
CN101371700A (en) * 2008-09-17 2009-02-25 中国科学院广州化学研究所 Method for unitedly extracting anise tree volatile oil and shikimic acid crude extract

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101078020A (en) * 2006-05-23 2007-11-28 曹庸 Biological transformation and purification method for illicium plants shikimic acid
CN1931822A (en) * 2006-09-28 2007-03-21 广西万山香料有限责任公司 Process of extracting shikimic acid from aniseed
CN1931985A (en) * 2006-09-28 2007-03-21 广西万山香料有限责任公司 Process of extracting aniseed oil from aniseed
CN100999461A (en) * 2007-01-13 2007-07-18 红河学院 Extraction separation tech. of octagonal shickimmi oxalic acid
CN101371700A (en) * 2008-09-17 2009-02-25 中国科学院广州化学研究所 Method for unitedly extracting anise tree volatile oil and shikimic acid crude extract

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