CN113372314B - High-purity furandiene crystal and preparation method thereof - Google Patents
High-purity furandiene crystal and preparation method thereof Download PDFInfo
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- 239000013078 crystal Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 230000002829 reductive effect Effects 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 230000004580 weight loss Effects 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 238000002076 thermal analysis method Methods 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000002474 experimental method Methods 0.000 claims description 4
- 230000001360 synchronised effect Effects 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- 229910002483 Cu Ka Inorganic materials 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 230000000630 rising effect Effects 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 10
- 239000003208 petroleum Substances 0.000 abstract description 5
- 238000004440 column chromatography Methods 0.000 abstract description 4
- 238000001953 recrystallisation Methods 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- VMDXHYHOJPKFEK-IAVOFVOCSA-N furanodiene Chemical compound C1\C(C)=C\CC\C(C)=C\CC2=C1OC=C2C VMDXHYHOJPKFEK-IAVOFVOCSA-N 0.000 description 7
- ZTKVJHVJKDVVES-UHFFFAOYSA-N furanodiene Natural products CC1CCC=C(/C)Cc2occ(C)c2CC1 ZTKVJHVJKDVVES-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- 240000009138 Curcuma zedoaria Species 0.000 description 4
- 235000003405 Curcuma zedoaria Nutrition 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000001812 curcuma zedoaria berg. rosc. Substances 0.000 description 4
- 235000019509 white turmeric Nutrition 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000010681 turmeric oil Substances 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 235000003392 Curcuma domestica Nutrition 0.000 description 1
- 244000008991 Curcuma longa Species 0.000 description 1
- 230000010190 G1 phase Effects 0.000 description 1
- 208000032612 Glial tumor Diseases 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 206010023825 Laryngeal cancer Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001772 anti-angiogenic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004709 cell invasion Effects 0.000 description 1
- 230000012292 cell migration Effects 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 235000003373 curcuma longa Nutrition 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 206010023841 laryngeal neoplasm Diseases 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a high-purity furandiene crystal and a preparation method thereof. Compared with the powdered furandiene obtained by traditional column chromatography extraction and concentration and furandiene obtained by petroleum ether recrystallization, the furandiene crystal prepared by the method has high purity and higher stability.
Description
Technical Field
The invention relates to a high-purity furandiene crystal and a preparation method thereof, belonging to the field of pharmaceutical chemistry.
Background
The zedoary turmeric oil is obtained by steam distillation of the material of the zedoary turmeric, and is received in 2015 edition of Chinese pharmacopoeia, and contains more than twenty chemical components such as various sesquiterpenes.
Furanodiene is one of the main active ingredients of zedoary turmeric oil, and has analgesic, antibacterial, antiviral, antiinflammatory, and liver protecting effects. Patent CN 200710169718.3 discloses the treatment of laryngeal cancer, leukemia, glioma, ascites carcinoma, cervical cancer and the like using furanodiene. Whereas recent studies have shown that: furanadine has anti-angiogenic effect, and exerts its killing effect by inhibiting vascular endothelial cell growth, invasion, migration and lumen formation. Report of the latest literature: furanadine can exert an anti-tumor effect by inducing apoptosis, self-moving and blocking the G1 phase of the 95-d lung cancer cells, and can exert a synergistic anti-tumor effect by cell cycle blocking effect and taxol, which is probably one of the mechanisms for inhibiting tumor growth.
Therefore, the furanodiene is extracted from the zedoary turmeric oil, and the high-purity furanodiene crystal is prepared, so that the stability can be improved, and a solid foundation can be laid for clinical popularization and application of furanodiene pharmaceutical preparations and derivative products.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a high-purity furandiene crystal and a preparation method thereof, and the furandiene prepared by the method has single crystal form and high stability.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows: a high purity furandiene crystal has a structural formula shown in formula I, and has characteristic peak at 13.580±0.2°,14.058±0.2°, 15.221±0.2°,17.086±0.2°,19.046±0.2°,19.642±0.2°,21.081±0.2°, 22.057±0.2°,24.287±0.2°,24.641±0.2°,26.426±0.2°,27.516±0.2°, 28.220±0.2°,30.078±0.2°,30.459±0.2° by X-ray powder diffraction pattern expressed by diffraction angle of 2θ+ -0.2 ° using Cu-Ka radiation
The synchronous thermal analysis experiment of the furandiene crystal has the following characteristics: the DSC graph shows that the two obvious endothermic processes are carried out, wherein the first initial point is 67.0+/-1 ℃, the end point is 78.8+/-1 ℃, the second initial point is 175.9+/-1 ℃, and the end point is 223.4+/-1 ℃; the TG pattern shows a weight loss process, the weight loss point is 184.7+/-1 ℃, and the weight loss is 98.68%; the test conditions of the synchronous thermal analysis experiment are as follows: the temperature rising rate is 10 ℃/min at 25-300 ℃.
The invention provides a preparation method of the furandiene crystal, which comprises the following steps:
(1) Adding the crude furandiene into an alcohol solvent, and heating to dissolve under stirring to obtain furandiene dissolution liquid;
(2) Cooling the furandiene solution obtained in the step (1) to 0-20 ℃, stirring and crystallizing for 5-8 hours, and separating out solid matters;
(3) Carrying out suction filtration on the solid matters separated out in the step (2) to obtain the solid matters after suction filtration;
(4) And (3) drying the solid obtained after the suction filtration in the step (3) under reduced pressure to obtain the high-purity furandiene crystal.
As a preferred embodiment of the production method of the present invention, in the step (1), the alcohol solvent is a lower alcohol.
Preferably, the lower alcohol is at least one of isopropanol, butanol, propanol, ethanol and methanol.
More preferably, the lower alcohol is ethanol. The ethanol is adopted as a solvent to recrystallize the crude furandiene, so that the obtained furandiene has higher purity, single crystal form and high product stability.
As a preferred embodiment of the preparation method of the present invention, in the step (1), the temperature is raised to 60 to 80 ℃ to dissolve.
As a preferred embodiment of the preparation method of the present invention, in the step (1), the volume weight ratio of the solvent to the furandiene crude product is (10-20): 1.
Preferably, the volume weight ratio of the solvent to the furandiene crude product is (10-15): 1. the smaller the volume to weight ratio of solvent to crude furandiene, the more mass of solid is recrystallized.
As a preferred embodiment of the preparation method of the present invention, in the step (2), the temperature is reduced to 5-20 ℃, and the crystallization is carried out for 5-8 hours under stirring.
Preferably, in the step (2), the temperature is reduced to 5-10 ℃. The lower the temperature, the more advantageous the crystallization.
As a preferred embodiment of the preparation method of the present invention, in the step (4), the temperature of the reduced pressure drying is 30 to 50℃and the pressure is-0.095 to-0.1 MPa.
Preferably, the temperature of the reduced pressure drying is 30 to 40 ℃. The lower the temperature of the reduced pressure drying, the higher the stability of the crystals obtained after drying.
Compared with the prior art, the invention has the beneficial effects that: compared with the furandiene obtained by column chromatography separation and the furandiene obtained by petroleum ether recrystallization, the furandiene prepared by the method has higher purity, single crystal form and high product stability.
Drawings
FIG. 1 is an HPLC chart of furandiene prepared in example 1.
FIG. 2 is a 1 H-NMR spectrum of furandiene prepared in example 1.
FIG. 3 is a 13 C-NMR spectrum of furandiene prepared in example 1.
FIG. 4 is an X-ray powder diffraction pattern of furandiene prepared in example 1.
FIG. 5 is a graphic representation of a simultaneous thermal analysis (TG-DSC) of furandienes prepared in example 1.
Detailed Description
For a better description of the objects, technical solutions and advantages of the present invention, the present invention will be further described with reference to the accompanying drawings and specific examples. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art.
Example 1
20G of the crude furandiene product is added into a 250mL three-necked flask, 200mL of absolute ethyl alcohol is added, and the temperature is raised to 75 ℃ and the mixture is stirred and dissolved. Cooling the obtained furandiene solution to 5 ℃, controlling the temperature to 5-10 ℃, stirring and crystallizing for 8 hours. Vacuum filtering, vacuum drying at 30-50 deg.c and pressure-0.095-0.1 MPa to obtain white crystal 16.10g and HPLC purity of 99.70%. The HPLC spectrum of furandiene prepared in this example is shown in FIG. 1, 1 H-NMR spectrum is shown in FIG. 2, 13 C-NMR spectrum is shown in FIG. 3, X-ray powder diffraction spectrum is shown in FIG. 4, and simultaneous thermal analysis (TG-DSC) spectrum is shown in FIG. 5.
As can be seen from FIG. 4, using Cu-Ka radiation, the X-ray powder diffraction pattern of the furandiene crystal, expressed as diffraction angles of 2θ.+ -. 0.2 °, has a characteristic peak at 13.580±0.2°,14.058±0.2°,15.221±0.2°, 17.086±0.2°,19.046±0.2°,19.642±0.2°,21.081±0.2°,22.057±0.2°, 24.287±0.2°,24.641±0.2°,26.426±0.2°,27.516±0.2°,28.220±0.2°, 30.078±0.2°,30.459±0.2°. As can be seen from fig. 5, the DSC profile shows two distinct endothermic processes, a first starting point 67.0±1 ℃, an ending point 78.8±1 ℃, a second starting point 175.9±1 ℃, and an ending point 223.4±1 ℃; the TG pattern shows a weight loss process, the weight loss point is 184.7+/-1 ℃, and the weight loss is 98.68%; the test conditions of the synchronous thermal analysis experiment are as follows: the temperature rising rate is 10 ℃/min at 25-300 ℃.
m.p.72～74℃;1H-NMR(CDCl3)：δ1.27(s,3H),δ1.60(s, 3H),δ2.26～2.07(m,4H),δ3.09～3.08(d,2H),δ3.43～3.56 (d,2H),δ4.75～4.73(t,1H),δ4.96～4.93(dd,1H),δ7.07 (s,1H).13C-NMR(CDCl3)：δ149.67(C15),δ135.94(C1),δ 134.32(C12),δ128.98～128.80(C7),δ127.55(C11),δ121.85 (C6),δ118.84(C2),δ77.23～76.80(C4),δ40.89(C14),δ39.45 (C9),δ26.81(C10),δ24.33(C5),δ16.45(C8),δ16.20(C13),δ8.90(C3).
Example 2
20G of the crude furandiene product is added into a 250mL three-necked flask, 400mL of isopropanol is added, and the temperature is raised to 60 ℃ and the solution is stirred. Cooling the obtained furandiene solution to 0 ℃, controlling the temperature to 0-5 ℃, stirring and crystallizing for 5 hours. Vacuum filtering, vacuum drying at 30-50 deg.c and pressure of-0.095 to-0.1 MPa to obtain white crystal 15.60g and HPLC purity of 99.42%. The spectrum of furandiene prepared in this example is the same as that of example 1.
Example 3
20G of crude furandiene product is added into a 250mL three-neck flask, 300mL of butanol is added, and the temperature is raised to 80 ℃ and the mixture is stirred and dissolved. Cooling the obtained furandiene solution to 20 ℃, controlling the temperature to 15-20 ℃, stirring and crystallizing for 6 hours. Vacuum filtering, vacuum drying at 30-50 deg.c and pressure of-0.095 to-0.1 MPa to obtain white crystal 15.23g and HPLC purity of 99.35%. The spectrum of furandiene prepared in this example is the same as that of example 1.
Example 4
20G of the crude furandiene product is added into a 250mL three-necked flask, 200mL of isopropanol is added, and the temperature is raised to 75 ℃ and the mixture is stirred and dissolved. Cooling the obtained furandiene solution to 5 ℃, controlling the temperature to 5-10 ℃, stirring and crystallizing for 8 hours. Vacuum filtering, vacuum drying at 30-50 deg.c and pressure of-0.095 to-0.1 MPa to obtain white crystal 15.31g and HPLC purity of 99.24%. The spectrum of furandiene prepared in this example is the same as that of example 1.
Comparative example 1
Separating and purifying the furandiene crude product by 5g column chromatography (chromatographic column filler is 200-300 meshes of silica gel, ethyl acetate and petroleum ether system developing agent, and performing dry sample loading), and collecting the developing agent in the furandiene outflow period. The collected single component furanodiene sample was concentrated under reduced pressure to give 2.22g of powder with an HPLC purity of 97.31%.
Comparative example 2
20G of crude furanodiene is added into a 250mL three-neck flask, 200mL of petroleum ether is added, and the temperature is raised to 75 ℃ and the mixture is stirred and dissolved. Cooling the obtained furandiene solution to 5 ℃, controlling the temperature to 5-10 ℃, stirring and crystallizing for 8 hours. Vacuum filtering, vacuum drying at 30-50 deg.c and pressure of-0.095 to-0.1 MPa to obtain white crystal 8.01g and HPLC purity of 97.45%.
Effect example 1
The furandiene prepared in example 1 and comparative examples 1 to 2 was subjected to stability test, and the added impurities were detected by HPLC, and the crystal modification was determined by X-ray powder diffraction and DSC. The test results are shown in Table 1.
TABLE 1
As is clear from Table 1, the furandiene crystals prepared by the method of the present invention were stable and no added impurities were present during the stability lofting period. The furandiene crystal obtained by column chromatography separation and the furandiene crystal obtained by petroleum ether recrystallization are amorphous powder, and have low purity and low stability.
Finally, it should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the scope of the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the technical solution of the present invention may be modified or substituted equally without departing from the spirit and scope of the technical solution of the present invention.
Claims (8)
1. A high-purity furandiene crystal having a structural formula as shown in formula I, characterized in that the crystal has an X-ray powder diffraction pattern having a characteristic peak at 13.580±0.2°,14.058±0.2°,15.221±0.2°,17.086±0.2°,19.046±0.2°,19.642±0.2°,21.081±0.2°,22.057±0.2°,24.287±0.2°,24.641±0.2°,26.426±0.2°,27.516±0.2°,28.220±0.2°,30.078±0.2°,30.459±0.2° and expressed as a diffraction angle of 2θ.+ -. 0.2 ℃ using Cu-Ka radiation
2. The furandiene crystal according to claim 1, characterized in that the simultaneous thermal analysis of said crystal has the following characteristics: the DSC graph shows that the two obvious endothermic processes are carried out, wherein the first initial point is 67.0+/-1 ℃, the end point is 78.8+/-1 ℃, the second initial point is 175.9+/-1 ℃, and the end point is 223.4+/-1 ℃; the TG pattern shows a weight loss process, the weight loss point is 184.7+/-1 ℃, and the weight loss is 98.68%; the test conditions of the synchronous thermal analysis experiment are as follows: the temperature rising rate is 10 ℃/min at 25-300 ℃.
3. The method for producing a furandiene crystal according to any one of claims 1 to 2, comprising the steps of:
(1) Adding the crude furandiene into an alcohol solvent, and heating to dissolve under stirring to obtain furandiene dissolution liquid; the alcohol solvent is lower alcohol; the lower alcohol is at least one of isopropanol, butanol, propanol, ethanol and methanol;
(2) Cooling the furandiene solution obtained in the step (1) to 0-20 ℃, stirring and crystallizing for 5-8 hours, and separating out solid matters;
(3) Carrying out suction filtration on the solid matters separated out in the step (2) to obtain the solid matters after suction filtration;
(4) And (3) drying the solid obtained after the suction filtration in the step (3) under reduced pressure to obtain the high-purity furandiene crystal.
4. A method of preparing as claimed in claim 3 wherein the lower alcohol is ethanol.
5. The method according to claim 3, wherein in the step (1), the temperature is raised to 60 to 80 ℃ to dissolve.
6. The process according to claim 3, wherein in the step (1), the volume/weight ratio of the solvent to the crude furandiene is (10 to 20): 1.
7. The method according to claim 3, wherein in the step (2), the temperature is reduced to 5-20 ℃, and the mixture is stirred and crystallized for 5-8 hours.
8. The method according to claim 3, wherein in the step (4), the temperature of the reduced pressure drying is 30 to 50℃and the pressure is-0.095 to-0.1 MPa.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101538259A (en) * | 2009-04-17 | 2009-09-23 | 杭州民生药业集团有限公司 | Crystal form A of zedoary root cyclic diolefine, preparation method thereof and application thereof in preparing anti-tumor drugs |
| CN106860876A (en) * | 2017-03-14 | 2017-06-20 | 胡江宇 | Oil of zedoary turmeric sustained release inclusion compound and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101538259A (en) * | 2009-04-17 | 2009-09-23 | 杭州民生药业集团有限公司 | Crystal form A of zedoary root cyclic diolefine, preparation method thereof and application thereof in preparing anti-tumor drugs |
| CN106860876A (en) * | 2017-03-14 | 2017-06-20 | 胡江宇 | Oil of zedoary turmeric sustained release inclusion compound and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 蓬莪术环二烯的晶体结构研究;张慧;烟台大学学报（自然科学与工程版）;第23卷(第1期);第38-41页 * |
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