WO2021047491A1 - 一种同时分离次大麻二酚和大麻萜酚的方法 - Google Patents

一种同时分离次大麻二酚和大麻萜酚的方法 Download PDF

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WO2021047491A1
WO2021047491A1 PCT/CN2020/113892 CN2020113892W WO2021047491A1 WO 2021047491 A1 WO2021047491 A1 WO 2021047491A1 CN 2020113892 W CN2020113892 W CN 2020113892W WO 2021047491 A1 WO2021047491 A1 WO 2021047491A1
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cannabidiol
phase
mobile phase
hypocannabidiol
cannabidivarin
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PCT/CN2020/113892
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邓力
余琦
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上海同田生物技术有限公司
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Priority to CA3150857A priority Critical patent/CA3150857A1/en
Priority to ES20862649T priority patent/ES2959023T3/es
Priority to JP2022539454A priority patent/JP7261943B2/ja
Priority to EP20862649.9A priority patent/EP4029850B1/en
Priority to US17/642,235 priority patent/US20220315512A1/en
Priority to AU2020344019A priority patent/AU2020344019B2/en
Publication of WO2021047491A1 publication Critical patent/WO2021047491A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
    • B01D15/1892—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns the sorbent material moving as a whole, e.g. continuous annular chromatography, true moving beds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/685—Processes comprising at least two steps in series
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
    • C07C39/19—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
    • 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 invention belongs to the field of cannabidiol processing, and particularly relates to a method for simultaneously separating hypocannabidiol and cannabidiol.
  • Cannabidivarin The molecular formula of Cannabidivarin is C 19 H 26 O 2 .
  • Hypocannabidiol is present in industrial hemp. The industrial hemp is subjected to alcohol extraction, etc. to obtain an extract containing hypocannabidiol.
  • Subcannabidiol (CBDV) can be used for the treatment of neurological disorders.
  • Cannabigerol The molecular formula of Cannabigerol is C 21 H 32 O 2 .
  • Cannabidiol is found in industrial hemp. The industrial hemp is subjected to alcohol extraction, etc. to obtain an extract containing cannabidiol.
  • Cannabidiol (CBG) can be used for the treatment of neurological disorders.
  • High Speed Countercurrent Chromatography (HSCCC) technology is a new separation and purification technology based on the principle of liquid-liquid distribution. It does not require any solid support or carrier. Both the stationary phase and the mobile phase are liquids without irreversible adsorption.
  • the technical problem to be solved by the present invention is to provide a method for the simultaneous separation of cannabidiol and cannabidiol.
  • the method adopts high-speed countercurrent chromatography technology to obtain >98% pure cannabidiol ( CBDV) and cannabidiol (CBG) of >97% purity.
  • the present invention provides a method for simultaneously separating cannabidiol and cannabidiol, including:
  • the solvent system is obtained by mixing n-hexane or n-heptane, methyl tert-butyl ether, acetonitrile or ethanol, and water in a volume ratio of 5-10:1-3:5-10:2-4.
  • the upper and lower two phases obtained by the separate collection are subjected to ultrasonic degassing treatment.
  • the conditions of the high-speed countercurrent chromatography are: the rotation direction is forward rotation, the rotation speed is 800 rpm; the column temperature is 25° C.; the flow rate of the mobile phase is 5 mL/min; and the detection wavelength of the detector is 214 nm.
  • the process conditions for removing the mobile phase are: rotary evaporation and vacuum drying at 55° C. and -0.085 MPa.
  • the solvent system of the present invention is determined by the solubility of cannabidiol and cannabidiol in two-phase immiscible solvents.
  • the present invention uses high-speed countercurrent chromatography technology to simultaneously separate and purify cannabidiol (CBDV) with a purity of >98% and cannabidiol (CBG) with a purity of >97% from the refined oil of the whole spectrum of industrial hemp.
  • the high-speed countercurrent chromatography technology of the present invention has the advantages of no sample loss, no pollution, high efficiency, large preparation volume, and solvent recovery and reuse.
  • the reagents of the solvent system used in the present invention can all be recycled and reused and have good environmental protection functions.
  • n-hexane, n-heptane, acetonitrile, ethanol, and methyl tert-butyl ether are all analytically pure reagents produced by Sinopharm Chemical Reagent Co., Ltd., water is deionized water, and full-spectrum refined oil of industrial hemp is a commercial product;
  • the high-speed counter-current chromatograph is a TBE-300C high-speed counter-current chromatograph produced by Shanghai Tongtian Biotechnology Co., Ltd.
  • Dissolve the refined oil of the whole spectrum of industrial hemp in the upper phase the upper phase is the stationary phase, and the lower phase is the mobile phase; high-speed countercurrent chromatography is used for separation, and the chromatographic conditions are set as follows: forward rotation, rotation speed of 800rpm; column temperature 25°C; The flow rate of the mobile phase is 5mL/min; the detection wavelength of the detector is 214nm; the sample is taken as 0 min, and the mixture of cannabidiol (CBDV) and the mobile phase is obtained within 140-200min; cannabidiol is obtained at 210-280min (CBG) and mobile phase mixed liquid, placed in a rotary evaporator, under the conditions of a water bath temperature of 55 °C, vacuum pressure -0.085MPa, rotary evaporation and vacuum drying, remove the lower phase, get hypocannabidiol (CBDV) and cannabis Terpene phenol (CBG) products.
  • CBDV cannabidiol
  • CBG cannab
  • CBD cannabidiol
  • the upper phase is the stationary phase
  • the lower phase is the mobile phase
  • high-speed countercurrent chromatography is used for separation, and the chromatographic conditions are set as follows: forward rotation, rotation speed of 800rpm; column temperature 25°C;
  • the flow rate of the mobile phase is 5mL/min;
  • the detection wavelength of the detector is 214nm, and the sample injection is 0min.
  • the mixed liquid of cannabidiol (CBDV) and mobile phase is obtained within 100 ⁇ 140min; cannabidiol is obtained at 150 ⁇ 200min (CBG) and mobile phase mixed liquid, placed in a rotary evaporator, under the conditions of a water bath temperature of 55 °C, vacuum pressure -0.085MPa, rotary evaporation and vacuum drying, remove the lower phase, get hypocannabidiol (CBDV) and cannabis Terpene phenol (CBG) products.
  • CBD cannabidiol

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Botany (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Degasification And Air Bubble Elimination (AREA)

Abstract

本发明涉及一种同时分离次大麻二酚和大麻萜酚的方法，包括：将溶剂体系充分震荡，静置，分开收集上、下两相；将市售工业大麻全谱系精制油溶解于上相中，以上相为固定相，下相为流动相，采用高速逆流色谱进行分离，分别得到次大麻二酚与流动相的混合液、大麻萜酚与流动相的混合液，去除流动相，得到次大麻二酚、大麻萜酚。本发明首次利用高速逆流色谱技术从工业大麻全谱系精制油中同时分离纯化得到＞98％纯度的次大麻二酚(CBDV)和＞97％纯度的大麻萜酚(CBG)。

Description

一种同时分离次大麻二酚和大麻萜酚的方法 技术领域
本发明属于大麻酚类加工领域，特别涉及一种同时分离次大麻二酚和大麻萜酚的方法。
背景技术
次大麻二酚(Cannabidivarin)分子式是C 19H 26O 2。次大麻二酚存在于工业大麻中。将工业大麻经过醇浸提等，即可得到含次大麻二酚的浸膏。次大麻二酚(CBDV)可用于神经病症的治疗。
大麻萜酚(Cannabigerol)分子式是C 21H 32O 2。大麻萜酚存在于工业大麻中。将工业大麻经过醇浸提等，即可得到含大麻萜酚的浸膏。大麻萜酚(CBG)可用于神经病症的治疗。
利用高速逆流色谱同时分离次大麻二酚和大麻萜酚与分离大麻二酚的不同在于，采用了不同的溶剂体系，以使得次大麻二酚和大麻萜酚得到更好的分离效果。
高速逆流色谱(HSCCC)技术是一种新的基于液液分配原理的分离纯化技术，它不需要任何固态支撑或载体，固定相和流动相皆为液体，无不可逆吸附。
目前还没有利用高速逆流色谱同时分离次大麻二酚和大麻萜酚的相关技术被公开。
发明内容
本发明所要解决的技术问题是提供一种同时分离次大麻二酚和大麻萜酚的方法，该方法采用高速逆流色谱技术，通过溶剂体系一步同时分离纯化得到＞98％纯度的次大麻二酚(CBDV)和＞97％纯度的大麻萜酚(CBG)。
本发明提供了一种同时分离次大麻二酚和大麻萜酚的方法，包括：
将溶剂体系充分振摇，静置，分开收集上、下两相；将工业大麻全谱系精制油溶解于上相中，以上相为固定相，下相为流动相，采用高速逆流色谱进行分离，分别得到次大麻二酚与流动相的混合液、大麻萜酚与流动相的混合液，去除流动相，得到次大麻二酚、大麻萜酚；
其中，溶剂体系由正己烷或正庚烷、甲基叔丁基醚、乙腈或乙醇、水按体积比为5～10：1～3：5～10：2～4混合而得。
所述分开收集得到的上、下两相进行超声脱气处理。
所述高速逆流色谱的条件为：转向为正转，转速为800rpm；柱温为25℃；流动相的流速为5mL/min；检测器的检测波长为214nm。
所述去除流动相的工艺条件为：在55℃、-0.085MPa条件下进行旋转蒸发真空干燥。
本发明所述溶剂体系由次大麻二酚和大麻萜酚在互不相溶的两相溶剂中的溶解度而定。
有益效果
(1)本发明首次利用高速逆流色谱技术从工业大麻全谱系精制油中同时分离纯化得到＞98％纯度的次大麻二酚(CBDV)和＞97％纯度的大麻萜酚(CBG)。
(2)本发明的高速逆流色谱技术具有无样品损耗、无污染、高效、大制备量，溶剂可回收再利用等优点。
(3)本发明中采用的溶剂体系的试剂皆可回收再利用，具有良好的环保功能。
具体实施方式
下面结合具体实施例，进一步阐述本发明。应理解，这些实施例仅用于说明本发明而不用于限制本发明的范围。此外应理解，在阅读了本发明讲授的内容之后，本领域技术人员可以对本发明作各种改动或修改，这些等价形式同样落于本申请所附权利要求书所限定的范围。
实施例中采用的试剂与仪器如下：
试剂：正己烷、正庚烷、乙腈、乙醇、甲基叔丁基醚均为国药集团化学试剂有限公司生产的分析纯试剂，水为去离子水，工业大麻全谱系精制油为市售产品；
仪器：高速逆流色谱仪为上海同田生物技术股份有限公司生产的TBE-300C型号高速逆流色谱仪。
实施例1
将正己烷、甲基叔丁基醚、乙腈、水按体积比为6：3：6：3混合制得溶剂体系，加入分液漏斗中，充分振摇，静置分相，获得两相混合液，分开收集上相和下相，分别置于超声波振荡器中进行超声脱气处理。将工业大麻全谱系精制油溶解于上相中，以上相为固定相，下相为流动相；采用高速逆流色谱进行分离，其中色谱条件设置为：正转，转速为800rpm；柱温25℃；流动相流速5mL/min；检测器的检测波长为214nm；以进完样为0min计，在140～200min得到次大麻二酚(CBDV)与流动相的混合液；在210～280min得到大麻萜酚(CBG)与流动相的混合液，置于旋转蒸发器中，在水浴温度55℃、真空压强-0.085MPa条件下进行旋转蒸发真空干燥，去除下相，得到次大麻二酚(CBDV)和大麻萜酚(CBG)产品。
通过HPLC对本实施例获得的产品的纯度进行分析，结果显示：次大麻二酚(CBDV) 纯度为98.42％，大麻萜酚(CBG)纯度为97.53％。
实施例2
将正庚烷、甲基叔丁基醚、乙醇、水按体积比为5：3：5：4混合制得溶剂体系，加入分液漏斗中，充分振摇，静置分相，获得两相混合液，分开收集上相和下相，分别置于超声波振荡器中进行超声脱气处理。将工业大麻全谱系精制油溶解于上相中，以上相为固定相，下相为流动相；采用高速逆流色谱进行分离，其中色谱条件设置为：正转，转速为800rpm；柱温25℃；流动相流速5mL/min；检测器的检测波长为214nm，以进完样为0min计，在100～140min得到次大麻二酚(CBDV)与流动相的混合液；在150～200min得到大麻萜酚(CBG)与流动相的混合液，置于旋转蒸发器中，在水浴温度55℃、真空压强-0.085MPa条件下进行旋转蒸发真空干燥，去除下相，得到次大麻二酚(CBDV)和大麻萜酚(CBG)产品。
通过HPLC对本实施例获得的产品的纯度进行分析，结果显示：次大麻二酚(CBDV)纯度为98.32％，大麻萜酚(CBG)纯度为97.15％。

Claims (4)

  1. 一种同时分离次大麻二酚和大麻萜酚的方法，包括：
    将溶剂体系充分振摇，静置，分开收集上、下两相；将工业大麻全谱系精制油溶解于上相中，以上相为固定相，下相为流动相，采用高速逆流色谱进行分离，分别得到次大麻二酚与流动相的混合液、大麻萜酚与流动相的混合液，去除流动相，得到次大麻二酚、大麻萜酚；
    其中，溶剂体系由正己烷或正庚烷、甲基叔丁基醚、乙腈或乙醇、水按体积比为5～10：1～3：5～10：2～4混合而得。
  2. 根据权利要求1所述的一种同时分离次大麻二酚和大麻萜酚的方法，其特征在于：所述分开收集得到的上、下两相进行超声脱气处理。
  3. 根据权利要求1所述的一种同时分离次大麻二酚和大麻萜酚的方法，其特征在于：所述高速逆流色谱的条件为：转向为正转，转速为800rpm；柱温为25℃；流动相的流速为5mL/min；检测器的检测波长为214nm。
  4. 根据权利要求1所述的一种同时分离次大麻二酚和大麻萜酚的方法，其特征在于：所述去除流动相的工艺条件为：在55℃、-0.085MPa条件下进行旋转蒸发真空干燥。
PCT/CN2020/113892 2019-09-11 2020-09-08 一种同时分离次大麻二酚和大麻萜酚的方法 WO2021047491A1 (zh)

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CA3150857A CA3150857A1 (en) 2019-09-11 2020-09-08 Method for simultaneously separating cannabidivarin and cannabigerol
ES20862649T ES2959023T3 (es) 2019-09-11 2020-09-08 Método de separación simultánea de cannabidivarina y cannabigerol
JP2022539454A JP7261943B2 (ja) 2019-09-11 2020-09-08 カンナビジバリンとカンナビゲロールを同時に分離する方法
EP20862649.9A EP4029850B1 (en) 2019-09-11 2020-09-08 Method for simultaneously separating cannabidivarin and cannabigerol
US17/642,235 US20220315512A1 (en) 2019-09-11 2020-09-08 Method for simultaneously separating cannabidivarin and cannabigerol
AU2020344019A AU2020344019B2 (en) 2019-09-11 2020-09-08 Method for simultaneously separating cannabidivarin and cannabigerol

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CN110590511B (zh) * 2019-09-11 2021-05-28 上海同田生物技术股份有限公司 一种同时分离次大麻二酚和大麻萜酚的方法
CN113135885A (zh) * 2021-04-07 2021-07-20 上海同田生物技术有限公司 一种高速逆流色谱分离纯化四氢次大麻酚的方法
CN114478195B (zh) * 2022-04-18 2022-07-29 北京蓝晶微生物科技有限公司 一种从微生物发酵产物中提取大麻萜酚的方法

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