CN117756620A - Preparation method of cis-jasmone - Google Patents
Preparation method of cis-jasmone Download PDFInfo
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- CN117756620A CN117756620A CN202311739265.9A CN202311739265A CN117756620A CN 117756620 A CN117756620 A CN 117756620A CN 202311739265 A CN202311739265 A CN 202311739265A CN 117756620 A CN117756620 A CN 117756620A
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- jasmine
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- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 title claims abstract description 45
- XMLSXPIVAXONDL-PLNGDYQASA-N Jasmone Chemical compound CC\C=C/CC1=C(C)CCC1=O XMLSXPIVAXONDL-PLNGDYQASA-N 0.000 title claims abstract description 44
- IVLCENBZDYVJPA-ARJAWSKDSA-N cis-Jasmone Natural products C\C=C/CC1=C(C)CCC1=O IVLCENBZDYVJPA-ARJAWSKDSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 56
- 241000207840 Jasminum Species 0.000 claims abstract description 41
- 235000010254 Jasminum officinale Nutrition 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000000047 product Substances 0.000 claims abstract description 23
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000002791 soaking Methods 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- 239000000706 filtrate Substances 0.000 claims abstract description 12
- 238000005470 impregnation Methods 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 238000002137 ultrasound extraction Methods 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000011347 resin Substances 0.000 claims description 26
- 229920005989 resin Polymers 0.000 claims description 26
- 238000001179 sorption measurement Methods 0.000 claims description 17
- 238000000926 separation method Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 238000011085 pressure filtration Methods 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000003463 adsorbent Substances 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 239000012982 microporous membrane Substances 0.000 claims description 3
- 241000628997 Flos Species 0.000 claims description 2
- 238000000605 extraction Methods 0.000 abstract description 14
- 229930003935 flavonoid Natural products 0.000 abstract description 6
- 150000002215 flavonoids Chemical class 0.000 abstract description 6
- 235000017173 flavonoids Nutrition 0.000 abstract description 6
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 241000196324 Embryophyta Species 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 238000004880 explosion Methods 0.000 abstract description 3
- 238000002386 leaching Methods 0.000 abstract description 3
- 239000003205 fragrance Substances 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 4
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 230000002925 chemical effect Effects 0.000 description 2
- 230000003749 cleanliness Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000013467 fragmentation Methods 0.000 description 2
- 238000006062 fragmentation reaction Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 230000009291 secondary effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 244000024873 Mentha crispa Species 0.000 description 1
- 235000014749 Mentha crispa Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- ZNJFBWYDHIGLCU-HWKXXFMVSA-N jasmonic acid Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-HWKXXFMVSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- XMLSXPIVAXONDL-SNAWJCMRSA-N trans-Jasmone Chemical compound CC\C=C\CC1=C(C)CCC1=O XMLSXPIVAXONDL-SNAWJCMRSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of plant extraction, in particular to a preparation method of cis-jasmone, which comprises the following operation steps: crushing raw materials: crushing flowers, stems and leaves of jasmine flowers for standby; and (3) solvent impregnation: putting crushed jasmine flowers, stems or leaves into a reaction kettle with heating and stirring functions, and adding a solvent for soaking; ultrasonic extraction: in the soaking process, under the condition of heating, ultrasonic wave is started to carry out multiple times of extraction, and the filtrates are combined. The preparation method of cis-jasmone adopts dimethyl carbonate as a solvent, and overcomes the unavoidable problem of organic solvent residue of the existing solvent for extracting total flavonoids of jasmine, so that the method for producing total flavonoids of jasmine by adopting dimethyl carbonate as the solvent does not pollute products and environment, and meets the safety requirements of medicines; the explosion limit of the dimethyl carbonate is 3.8-21.3%, and the dimethyl carbonate is used as a leaching solvent, so that the danger in production is greatly reduced, and the production safety is realized.
Description
Technical Field
The invention relates to the technical field of plant extraction, in particular to a preparation method of cis-jasmone.
Background
The jasmone is a natural substance existing in jasmine, spearmint, bergamot, peppermint, tea and various flowers, the jasmone exists in two different isomer forms around a pentenyl double bond, namely all-cis-jasmone and trans-jasmone, wherein the all-cis-jasmone has fruit fragrance, flower fragrance and jasmine odor, the natural jasmone component is mainly all-cis-jasmone, the synthetic jasmone is all-terrain, and the all-cis-jasmone is still the main component. Cis-jasmone is an important spice with wide application, has fragrance similar to jasmine flower fragrance, is one of important fragrance components of jasmine oil, and is mainly used in high-grade jasmine series cosmetic essence.
The extraction method of cis-jasmone mainly comprises a distillation method, an extraction method and a crystallization method, wherein the distillation method is one of the most commonly used extraction methods, volatile components in jasmine are mainly extracted by distillation, and the extraction method is to soak the jasmine in an organic solvent and then extract the jasmine by extraction. The crystallization rule is to crystallize the extracted jasmone solution to obtain cis-all jasmone with high purity.
The common extraction method generally uses alcohol, ketone and the like as solvents for extracting the jasmone, but because the alcohol, ketone solvents and the jasmone in the jasmine have similar properties, organic solvent residues inevitably exist in the extracted jasmone according to a similar compatibility principle, so that the purity of the jasmone is reduced, and the subsequent use is not facilitated; in addition, in the conventional extraction method for extracting and preparing the jasmone, after the solvent separates the jasmone from the jasmine, the separation of the jasmone from the jasmine impurities is usually realized by means of negative pressure filtration and the like, so that some tiny jasmine impurities are inevitably present in the subsequently separated jasmone, and the purity of the jasmone is further reduced.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of cis-jasmone, which solves the problems in the background art.
In order to achieve the above purpose, the invention is realized by the following technical scheme: the preparation method of cis-jasmone comprises the following operation steps:
crushing raw materials: crushing flowers, stems and leaves of jasmine flowers for standby;
and (3) solvent impregnation: putting crushed jasmine flowers, stems or leaves into a reaction kettle with heating and stirring functions, and adding a solvent for soaking;
ultrasonic extraction: in the soaking process, under the condition of heating, starting ultrasonic waves to extract for a plurality of times, and combining the filtrates;
solvent separation: adding the combined filtrate into a natural chromatographic tank for natural chromatography for 0.5-1 hr, or distilling under reduced pressure to separate solvent, continuously using the solvent in the next batch of production, separating solvent, performing negative pressure filtration, and concentrating under reduced pressure to obtain extract;
purifying active ingredients: the extractum is subjected to macroporous adsorption resin column, eluting with water, then separating and purifying by using ethanol solutions with different concentrations to obtain three sections, and selecting the last section as a target section product;
and then separating and purifying the obtained target segment product by a gel chromatographic column to obtain the jasmine extract (jasmone).
Preferably, the raw material is crushed by an extruder, a crusher or a press roller, and the crushing mesh number is 100-300 meshes.
Preferably, the solvent in the solvent impregnation is dimethyl carbonate, and the liquid-solid ratio in the solvent impregnation is 10-20:1, the soaking time is 10-30min.
Preferably, the ultrasonic extraction specifically comprises: heating to 80-92 deg.C, starting ultrasonic wave, controlling the time to 20-30 min, extracting for 2-4 times, and mixing filtrates.
Preferably, the reduced pressure distillation in the solvent separation is performed under the protection of nitrogen, carbon dioxide and argon to recover the dimethyl carbonate.
Preferably, the macroporous adsorption resin is one or more of AB-8, D101, DA-201, HPD-700, HP-20, HPD-722, HPD-300, HPD-200A, HPD-200B, HPD-100, HPD400, ADS-21, or HPD-850, preferably HPD-100.
Preferably, the purification of the active ingredients is specifically as follows: dissolving the extract with water, filtering, passing the liquid through macroporous adsorbent resin column, eluting with water at a flow rate (BV refers to column volume) of 0.2-1.5BV, and removing impurities by 8-12 BV; eluting with 30vol%, 60vol% and 90vol% ethanol for 15-20BV, and collecting 90vol% eluate for reduced pressure concentration to obtain target section product; the dosage of the macroporous resin is 10-20 times of the mass of the extract; the height-diameter ratio of the macroporous adsorption resin column is 5-10:1.
The macroporous adsorption resin can process a large amount of tobacco extract containing aroma components after alcohol extraction, rapidly remove substances such as polysaccharide, water-soluble pigment and the like, is favorable for further separation and purification of the subsequent aroma components, can realize industrial-grade quantity processing by using the macroporous adsorption resin, and has shorter processing time period.
Preferably, the gel chromatographic column separation and purification specifically comprises: dissolving the obtained target product with ethanol, filtering with 0.6-0.8 μm microporous membrane, adding into gel chromatographic column, eluting with ethanol at flow rate of 2-5 drops/sec, collecting 6-6.5 hr, and concentrating under reduced pressure to obtain the flos Jasmini sambac extract. Concentrating under reduced pressure at 50-65deg.C, such as 50deg.C, 55deg.C, 60deg.C or 65deg.C, etc.; vacuum degree of reduced pressure concentration is-0.08-0.1 Mpa, such as-0.08 Mpa, -0.085Mpa, -0.09Mpa or-0.095 Mpa.
Preferably, the filler of the gel chromatographic column is one or more of SephadexLH-20, sephadexG-25 or SephadexG-10; the dosage of the gel filler is 30-50 times of the mass of the target product; the height-diameter ratio of the gel column is 50-120:1. Such as 60:1, 70:1, 80:1, 90:1, 100:1, 110:1.
The invention provides a preparation method of cis-jasmone, which has the following beneficial effects:
1. the preparation method of cis-jasmone adopts dimethyl carbonate as a solvent, and overcomes the unavoidable problem of organic solvent residue of the existing solvent for extracting total flavonoids of jasmine, so that the method for producing total flavonoids of jasmine by adopting dimethyl carbonate as the solvent does not pollute products and environment, and meets the safety requirements of medicines; the explosion limit of the dimethyl carbonate is 3.8-21.3%, and the dimethyl carbonate is used as a leaching solvent, so that the danger in production is greatly reduced, the production safety is realized, and meanwhile, the dimethyl carbonate has no problem on the health of operators, and is a low-cost green solvent integrating cleanliness and safety.
2. According to the preparation method of cis-jasmone, the macroporous adsorption resin is combined with the gel chromatographic column in a separating way, so that the high-purity jasmone extract (jasmone) can be quickly and efficiently prepared, the preparation process is simple and easy to realize, and the macroporous resin and the gel can be repeatedly applied, so that the preparation method is economical and efficient.
3. According to the preparation method of the cis-jasmone, when jasmine is immersed by the solvent, the dissolution of the effective components of the jasmine is accelerated by the cavitation effect of ultrasonic waves, and meanwhile, the secondary effects of the ultrasonic waves, such as mechanical vibration, diffusion, fragmentation and chemical effects, are utilized, so that the diffusion release of the effective components of the jasmine can be accelerated, the effective components of the jasmine can be fully mixed with the solvent, and the extraction rate of the effective components in the jasmine is improved.
Drawings
FIG. 1 is a schematic diagram of the process flow of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments.
Referring to fig. 1, the present invention provides the following technical solutions: the preparation method of cis-jasmone is characterized by comprising the following steps: the method comprises the following operation steps:
crushing raw materials: crushing flowers, stems and leaves of jasmine flowers for standby;
and (3) solvent impregnation: putting crushed jasmine flowers, stems or leaves into a reaction kettle with heating and stirring functions, and adding a solvent for soaking;
ultrasonic extraction: in the soaking process, under the condition of heating, starting ultrasonic waves to extract for a plurality of times, and combining the filtrates;
solvent separation: adding the combined filtrate into a natural chromatographic tank for natural chromatography for 0.5-1 hr, or distilling under reduced pressure to separate solvent, continuously using the solvent in the next batch of production, separating solvent, performing negative pressure filtration, and concentrating under reduced pressure to obtain extract;
purifying active ingredients: the extractum is subjected to macroporous adsorption resin column, eluting with water, then separating and purifying by using ethanol solutions with different concentrations to obtain three sections, and selecting the last section as a target section product;
and then separating and purifying the obtained target section product by a gel chromatographic column to obtain a jasmine extract (jasmone).
The raw material is crushed by an extruder, a crusher or a press roller, the crushing mesh number is 100-300 meshes, and jasmine flowers, stems or leaves are crushed by the extruder, the crusher or the press roller, so that the jasmine active ingredients can be rapidly extracted, the energy consumption is reduced, and the product yield is higher.
The solvent in the solvent impregnation is dimethyl carbonate, and the liquid-solid ratio in the solvent impregnation is 10-20:1, the dipping time is 10-30min, the raw materials are dipped and extracted after wetting, the technical problems that the solvent is difficult to permeate and the active ingredients are difficult to lead out are solved, the explosion limit of the dimethyl carbonate is 3.8-21.3%, the dimethyl carbonate is used as a leaching solvent, the danger in production is greatly reduced, the production safety is realized, meanwhile, the dimethyl carbonate does not have the problem of health to operators, and the environment-friendly solvent with low price integrates the cleanliness and the safety is provided.
The ultrasonic extraction is specifically as follows: heating to 80-92 deg.C, starting ultrasonic wave, controlling the time to 20-30 min, extracting for 2-4 times, mixing filtrates, utilizing cavitation of ultrasonic wave to accelerate dissolution of effective components of plant, and simultaneously utilizing secondary effect of ultrasonic wave, mechanical vibration, diffusion, fragmentation, chemical effect, etc., to accelerate diffusion release of active components of jasmine and fully mixing with solvent, thereby facilitating complete extraction and product yield reaching 98.6%.
The reduced pressure distillation in the solvent separation is to recover the dimethyl carbonate under the protection of nitrogen, carbon dioxide and argon, and the dimethyl carbonate is adopted as the solvent, so that the problem of organic solvent residue which is unavoidable in the existing solvent for extracting the jasmine total flavonoids is solved, and the dimethyl carbonate is adopted as the solvent for producing the jasmine total flavonoids, so that the product is not polluted, the environment is not polluted, and the safety requirements of medicines are met.
The macroporous adsorption resin is one or more of AB-8, D101, DA-201, HPD-700, HP-20, HPD-722, HPD-300, HPD-200A, HPD-200B, HPD-100, HPD400, ADS-21 or HPD-850, preferably HPD-100, and the high-purity jasmine extract (jasmonate) can be prepared quickly and efficiently by separating and combining the macroporous adsorption resin and a gel chromatographic column, the preparation process is simple and easy to realize, and the macroporous resin and gel can be repeatedly applied, so that the method is economical and efficient.
The purification of the effective components is specifically as follows: dissolving the extract with water, filtering, passing the liquid through macroporous adsorbent resin column, eluting with water at a flow rate (BV refers to column volume) of 0.2-1.5BV, and removing impurities by 8-12 BV; eluting with 30vol%, 60vol% and 90vol% ethanol for 15-20BV, and collecting 90vol% eluate for reduced pressure concentration to obtain target section product; the dosage of macroporous resin is 10-20 times of the mass of the extract; the height-diameter ratio of the macroporous adsorption resin column is 5-10:1.
The macroporous adsorption resin can process a large amount of tobacco extract containing aroma components after alcohol extraction, rapidly remove substances such as polysaccharide, water-soluble pigment and the like, is favorable for further separation and purification of the subsequent aroma components, can realize industrial-grade quantity processing by using the macroporous adsorption resin, and has shorter processing time period.
The gel chromatographic column separation and purification specifically comprises the following steps: dissolving the obtained target product with ethanol, filtering with 0.6-0.8 μm microporous membrane, adding into gel chromatographic column, eluting with ethanol at flow rate of 2-5 drops/sec, collecting 6-6.5 hr, and concentrating under reduced pressure to obtain jasmine extract. Concentrating under reduced pressure at 50-65deg.C, such as 50deg.C, 55deg.C, 60deg.C or 65deg.C, etc.; vacuum degree of reduced pressure concentration is-0.08-0.1 Mpa, such as-0.08 Mpa, -0.085Mpa, -0.09Mpa or-0.095 Mpa.
The filler of the gel chromatographic column is one or more of SephadexLH-20, sephadexG-25 or SephadexG-10; the dosage of the gel filler is 30-50 times of the mass of the target product; the height-diameter ratio of the gel column is 50-120:1. Such as 60:1, 70:1, 80:1, 90:1, 100:1, 110:1.
Embodiment one:
crushing raw materials: crushing flowers, stems and leaves of jasmine flowers by a crusher, wherein the crushing mesh is 200 meshes;
and (3) solvent impregnation: putting crushed jasmine flowers, stems or leaves into a reaction kettle with heating and stirring functions, adding dimethyl carbonate for soaking, wherein the liquid-solid ratio during solvent soaking is 15:1, soaking time is 20min;
ultrasonic extraction: heating to 90deg.C after soaking, starting ultrasonic wave, controlling for 25 min, extracting for 3 times, and mixing filtrates;
solvent separation: distilling the combined filtrate under reduced pressure, taking nitrogen, carbon dioxide and argon as shielding gas, separating out solvent, then carrying out negative pressure filtration, and concentrating under reduced pressure to obtain extract;
purifying active ingredients: dissolving the extract with water, filtering, passing the liquid through a macroporous adsorption resin column mixed by AB-8, D101 and DA-201, eluting with water for 10BV to remove impurities at a flow rate of 1.2BV/h (BV refers to column volume); eluting with 30vol%, 60vol% and 90vol% ethanol for 18BV, and collecting 90vol% eluate for reduced pressure concentration to obtain target segment product; the dosage of macroporous resin is 15 times of the mass of the extract; the height-diameter ratio of the macroporous adsorption resin column is 8:1;
dissolving and filtering the obtained target section product with ethanol, filtering with 0.7 μm microporous filter membrane, adding into gel chromatographic column with filler of SephadexLH-20, and the gel filler amount is 40 times of the target product mass; eluting with ethanol at a flow rate of 4 drops/s at a height-diameter ratio of 100:1, collecting the fraction of 6.2h, and concentrating under reduced pressure to obtain the jasmine extract (jasmone).
In the description of the present invention, it should be noted that, directions or positional relationships indicated by terms such as "center", "upper", "lower", "left", "right", "vertical", "horizontal", "inner", "outer", etc., are based on directions or positional relationships shown in the drawings, are merely for convenience of description and simplification of description, and do not indicate or imply that the apparatus or element to be referred to must have a specific direction, be constructed and operated in the specific direction, and thus should not be construed as limiting the present invention; the terms "first," "second," "third," and the like, are used for descriptive purposes only and are not to be construed as indicating or implying relative importance, and furthermore, unless explicitly specified and limited otherwise, the terms "mounted," "connected," "coupled," and the like are to be construed broadly, and may be fixedly coupled, detachably coupled, or integrally coupled, for example; can be mechanically or electrically connected; can be directly connected or indirectly connected through an intermediate medium, and can be communication between two elements. The specific meaning of the above terms in the present invention will be understood in specific cases by those of ordinary skill in the art. Moreover, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (9)
1. The preparation method of cis-jasmone is characterized by comprising the following steps: the method comprises the following operation steps:
crushing raw materials: crushing flowers, stems and leaves of jasmine flowers for standby;
and (3) solvent impregnation: putting crushed jasmine flowers, stems or leaves into a reaction kettle with heating and stirring functions, and adding a solvent for soaking;
ultrasonic extraction: in the soaking process, under the condition of heating, starting ultrasonic waves to extract for a plurality of times, and combining the filtrates;
solvent separation: adding the combined filtrate into a natural chromatographic tank for natural chromatography for 0.5-1 hr, or distilling under reduced pressure to separate solvent, continuously using the solvent in the next batch of production, separating solvent, performing negative pressure filtration, and concentrating under reduced pressure to obtain extract;
purifying active ingredients: the extractum is subjected to macroporous adsorption resin column, eluting with water, then separating and purifying by using ethanol solutions with different concentrations to obtain three sections, and selecting the last section as a target section product;
and then separating and purifying the obtained target segment product by a gel chromatographic column to obtain the jasmine extract (jasmone).
2. The method for preparing cis-jasmone according to claim 1, wherein: the raw material is crushed by an extruder, a crusher or a press roller, and the crushing mesh number is 100-300 meshes.
3. The method for preparing cis-jasmone according to claim 1, wherein: the solvent in the solvent impregnation is dimethyl carbonate, and the liquid-solid ratio in the solvent impregnation is 10-20:1, the soaking time is 10-30min.
4. The method for preparing cis-jasmone according to claim 1, wherein: the ultrasonic extraction is specifically as follows: heating to 80-92 deg.C, starting ultrasonic wave, controlling the time to 20-30 min, extracting for 2-4 times, and mixing filtrates.
5. A process for the preparation of cis-jasmone according to claim 3, characterized in that: the reduced pressure distillation in the solvent separation is to recover the dimethyl carbonate under the protection of nitrogen, carbon dioxide and argon.
6. The method for preparing cis-jasmone according to claim 1, wherein: the macroporous adsorption resin is one or more of AB-8, D101, DA-201, HPD-700, HP-20, HPD-722, HPD-300, HPD-200A, HPD-200B, HPD-100, HPD400, ADS-21 or HPD-850.
7. The method for preparing cis-jasmone according to claim 6, wherein: the purification of the effective components is specifically as follows: dissolving the extract with water, filtering, passing the liquid through macroporous adsorbent resin column, eluting with water at a flow rate (BV refers to column volume) of 0.2-1.5BV, and removing impurities by 8-12 BV; eluting with 30vol%, 60vol% and 90vol% ethanol for 15-20BV, and collecting 90vol% eluate for reduced pressure concentration to obtain target section product; the dosage of the macroporous resin is 10-20 times of the mass of the extract; the height-diameter ratio of the macroporous adsorption resin column is 5-10:1.
8. The method for preparing cis-jasmone according to claim 7, wherein: the gel chromatographic column separation and purification specifically comprises the following steps: dissolving the obtained target product with ethanol, filtering with 0.6-0.8 μm microporous membrane, adding into gel chromatographic column, eluting with ethanol at flow rate of 2-5 drops/sec, collecting 6-6.5 hr, and concentrating under reduced pressure to obtain the flos Jasmini sambac extract.
9. The method for preparing cis-jasmone according to claim 8, wherein: the filler of the gel chromatographic column is one or more of SephadexLH-20, sephadexG-25 or SephadexG-10; the dosage of the gel filler is 30-50 times of the mass of the target product; the height-diameter ratio of the gel column is 50-120:1.
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