CN105669812A - Method of separating sitosterol from extraction waste of fructus aurantii immaturus - Google Patents
Method of separating sitosterol from extraction waste of fructus aurantii immaturus Download PDFInfo
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- CN105669812A CN105669812A CN201511013964.0A CN201511013964A CN105669812A CN 105669812 A CN105669812 A CN 105669812A CN 201511013964 A CN201511013964 A CN 201511013964A CN 105669812 A CN105669812 A CN 105669812A
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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Abstract
The invention relates to a method of separating sitosterol from extraction waste of fructus aurantii immaturus, wherein the method includes the steps of: extraction, column chromatography, elution, concentration, purification and drying to prepare the sitosterol. In the method, through the extraction, column chromatography and re-crystallization purification, the sitosterol in high purity is separated from the extraction waste of fructus aurantii immaturus. The purity of the sitosterol separated and extracted from the extraction waste of the fructus aurantii immaturus is higher than 98%, thereby achieving waste recycling and having high economic and environmental protective benefit.
Description
Technical field
The present invention relates to a kind of method separating sitosterol from Fructus Aurantii Immaturus extraction garbage.
Background technology
Sitosterol is the material that a class has strong physiologically active, there are reduction cholesterol, blood fat reducing, antitumor, prevent and treat the physiological active functionses such as heart disease, it is the important raw materials for production of steroid drugs and vitamin D3, and has purposes widely in daily-use chemical industry, cosmetics, growth of animal agent etc. Along with the demand in steroidal market in recent years increases severely, supply falls short of demand especially for phytosterin compound demand, and price is also rise year by year. Sitosterol is widely present in the plant of the natures such as Oryza glutinosa, Semen Tritici aestivi, Semen Maydis, Brassica campestris L, but seldom has industrial utility value owing to content is low. Industrial is all much extract from some enrichment waste materials, so yield is subject to a definite limitation.
Current Fructus Aurantii Immaturus is industrially mainly used in extracting Hesperidin, and existing extracting method is roughly divided into water extraction and alcohol extraction two kinds. Wherein water extraction pollutes relatively big, and alcohol extraction has pollution little, and extraction ratio is high, the advantage of good product quality, will certainly will replace extraction process by water gradually. In Fructus Aurantii Immaturus alcohol extraction process, mass efficient material is extracted, separate the waste liquid after Hesperidin concentrated after have mass efficient material collection in waste liquid. Find that the sitosterol in waste liquid has good value by analysis.
Summary of the invention
It is an object of the invention to provide a kind of method of extracting and developing high-purity sitosterol from Fructus Aurantii Immaturus extraction garbage.
In Fructus Aurantii Immaturus industrialized production, often only extract Hesperidin and the Neosynephrine of the inside, all the other effective ingredient are ignored, wherein containing 3-5% Sitosterolum in garbage, 3%-4 Pericarpium Citri tangerinae element, 0.3-0.5% Nobiletin, and these effective ingredient are all the products that some added values are significantly high, directly abandon and cause very big waste. Present invention solves the technical problem that and be, the Neosynephrine mother solution during Fructus Aurantii Immaturus is produced is easily separated, and separates wherein Sitosterolum, it is achieved refuse reclamation, has higher economical and environmentally friendly benefit.
The method separating sitosterol from Fructus Aurantii Immaturus extraction garbage of the present invention includes step:
(A) offal treatment: take Fructus Aurantii Immaturus and separate the concentrated solution of Hesperidin after alcohol extraction, this effluent solution is further concentrated to concentration 1.02-1.12g/cm3, it is preferable that 1.05-1.10g/cm3;
(B) extracting: the garbage processed adds standing after organic stirring solvent extracts, and separates organic layer, optionally water layer repeats aforesaid operations one or many with organic solvent again, is merged by the extract of organic facies, stands;
(C) chromatography: extract peroxidating aluminum or silica gel column chromatography are adsorbed, crosses eluting after post completes, collects the eluent containing sitosterol;
(D) eluent concentration, crystallization, dry: the eluent containing sitosterol has been concentrated into crystallization; Concentrated solution is lowered the temperature, stands crystallization, crystallization sucking filtration, dry to obtain crude product;
(E) refining: the crude product that step (D) produces adds ethanol, it is heated to reflux dissolving, filters, filtrate is concentrated into original volume 1/3-1/12, it is preferable that 1/5-1/10;
(F) secondary crystallization, dry: concentrated solution stirring cooling, stands crystallization; Crystallization sucking filtration, washing, drain, then dry, it is thus achieved that product.
In the present invention, it is after Fructus Aurantii Immaturus alcohol extraction Neosynephrine, will extract slag alcohol aqueous slkali and extract, then adjust pH to acid, precipitate out Hesperidin that Fructus Aurantii Immaturus separates the concentrated solution of Hesperidin after alcohol extraction, and mother liquor concentrations reclaims the concentration residual liquid obtained after alcohol.
Further, it is obtained as below that described Fructus Aurantii Immaturus separates the concentrated solution of Hesperidin after alcohol extraction: pulverized by Fructus Aurantii Immaturus, crosses 60 orders, 2-4 times amount 50-80% methanol or soak with ethanol, repeats 1-3 time, and extracting solution merging concentrates to obtain Neosynephrine; Extract 2-6 times of 60-90% methanol of slag or ethanol aqueous slkali (alkali consumption is the 2-5% of solvent load) circulation immersion 12-16 hour, repeat 1-2 time, extracting solution merges, hydrochloric acid adjusts PH to 4-5, precipitates out a large amount of solid, stands 6-10 hour, filter, obtaining Hesperidin, mother liquor concentrations reclaims alcohol, and concentration residual liquid is that Fructus Aurantii Immaturus extracts garbage.
In a preferred embodiment, the concentration in step (A) is to concentrate at 95-100 DEG C of normal pressure.
Preferably, in step (B), extraction organic solvent is selected from ethers (such as petroleum ether, diisobutyl ether, n-butyl ether) or hydro carbons (including chain hydro carbons, ring-type hydro carbons, for instance normal hexane, hexamethylene).
In a preferred embodiment, the extraction of step (B) is to heat to 60-65 DEG C at the effluent solution processed, add organic solvent such as ethers (such as petroleum ether, diisobutyl ether, n-butyl ether) or hydro carbons (includes chain hydro carbons, ring-type hydro carbons, such as normal hexane, hexamethylene) stir extraction 30 minutes ~ 2 hours, preferably about 60 minutes, stand 15 minutes ~ 1 hour, preferably about 30 minutes, separate organic layer, water layer repeats aforesaid operations 2-3 time with organic solvent again, the extract of organic facies is merged, stand 1 ~ 4 hour, it is preferable that about 2 hours.
In a preferred embodiment, the chromatography of step (C) includes adsorbing extract peroxidating aluminum or silica gel column chromatography, cross after post completes with the petroleum ether ethyl acetate mixture of 9:1 or 95:5 cyclohexane ethyl acetate mixed solvent eluting, collect the eluent containing sitosterol.
In a preferred embodiment, the eluent concentration of step (D), crystallization, dry include the eluent containing sitosterol has been concentrated into crystallization; Concentrated solution is cooled to 20-25 DEG C, stands crystallization 8 hours, crystallization sucking filtration, and 80 DEG C dry to obtain crude product.
In a preferred embodiment, refining the including of step (E): the crude product that step (D) produces adds crude product weight 6-10 times, it is preferable that the 90-95% ethanol of 8 times, is heated to reflux 1-2h and dissolves, filter, and filtrate 80-90 DEG C is concentrated into original volume 1/5-1/10.
In a preferred embodiment, concentrated solution stirring is cooled to 5-10 DEG C by the secondary crystallization of step (F), dry including, and stands crystallization 12-24h; Crystallization sucking filtration, washing with alcohol, drain; Crystallization 75 DEG C-95 DEG C after sucking filtration, it is preferable that about 85 DEG C of drying, obtain product.
Advantages of the present invention
Neosynephrine mother solution in Fructus Aurantii Immaturus production is easily separated by the present invention, separates wherein Sitosterolum, and its purity is more than 98 mass %, it is achieved refuse reclamation, has higher economical and environmentally friendly benefit.
Accompanying drawing explanation
Fig. 1 is the ultraviolet spectra collection of illustrative plates of embodiment 1 gained crystallization.
Fig. 2 is the infared spectrum of the sitosterol of bibliographical information.
Fig. 3 is the infared spectrum of embodiment 1 gained crystallization.
Fig. 4 (a) is the high-efficient liquid phase chromatogram of sitosterol standard control; Fig. 4 (b) is the high-efficient liquid phase chromatogram of embodiment 1 gained sitosterol sample; Fig. 4 (c) is the high-efficient liquid phase chromatogram of sitosterol aggregate sample (embodiment 1 gained sample+standard substance).
Detailed description of the invention
For make those skilled in the art clearly with clear and definite technical scheme, special provide following preferred embodiment, but the technological thought of the present invention be not limited to following example.
Preparation example
Being pulverized by Fructus Aurantii Immaturus, cross 60 orders, by 70% soak with ethanol of the 3 of Fructus Aurantii Immaturus times of weight, repeat 3 times, extracting solution merging concentrates to obtain Neosynephrine; Extract the slag 5 times of 70% ethanol aqueous slkali about 4 mass % of etoh solvent consumption (the alkali sodium hydroxide concentration be) circulation immersion 15 hours, repeat 2 times, extracting solution merges, and hydrochloric acid adjusts PH to 4, precipitates out a large amount of solid, stand 8 hours, filtering, obtain Hesperidin, mother liquor concentrations reclaims alcohol, concentration residual liquid is that Fructus Aurantii Immaturus extracts garbage, for following example.
Embodiment one
Take 2000ml Fructus Aurantii Immaturus and extract garbage, 100 DEG C of normal pressure concentrations, obtain concentration 1.08g/cm3Concentrated solution 850ml, is cooled to 65 DEG C by concentrated solution, adds petroleum ether 850ml stirring solvent and extracts 60 minutes, stands 30 minutes, divide and take petroleum ether extraction layer in 65 DEG C of water-baths; Water layer repeats extracting operation 2 times with 850ml petroleum ether again, petroleum ether extraction liquid will be had to merge, stand 2 hours. And 600g chromatographic silica gel wet method appropriate with petroleum ether fills post. Extract is joined in silicagel column, controlled post speed, extract is crossed after post completes with the petroleum ether of 9:1: ethyl acetate mixture mixed solvent eluting, and detection is sent out in eluent crystallization to be had and collect eluent during sitosterol and can't check sitosterol to eluent, collects eluent 8500ml altogether. Eluent containing sitosterol is heated and has been concentrated into crystallization; Concentrated solution is cooled to 25 DEG C, stands crystallization 8 hours, crystallization, sucking filtration, and 80 DEG C dry to obtain crude product 25.2g. Taking 95% ethanol 202g and add 25.2g crude product, agitating heating refluxes 1 hour, filtered while hot, when filtrate 85 DEG C is concentrated into original volume 1/5, stops heating, is cooled to 10 DEG C, and insulation stands 12 hours. Crystal solution sucking filtration, filter cake washing with alcohol, drain and flow out to without filtrate. Crystallization after sucking filtration, in 85 DEG C of drying, obtains product 18.5g, HPLC detection level 98.3%.
Products obtained therefrom thin layer detects, the not aobvious fluorescence of ultraviolet condition, the heating colour developing of sulphuric acid vanillin. Take crystallization and be dissolved in acetic anhydride, add concentrated sulfuric acid solution and present red in blue color change, tentatively judge that list of references report infers that this crystallization is cupreol containing steroidal ring. Ultraviolet spectra collection of illustrative plates is as shown in Figure 1 for TU-1901 dual-beam ultraviolet-uisible spectrophotometer (Beijing Pu Xi all purpose instrument company limited).
Sequence number peak bottom wavelength (nm) Abs annotates
1 peak 282.000.881
2 peak 271.000.835
3 peak 208.001.843
1 paddy 276.000.723
Infrared discriminating: IR-Prestige21 type infrared scanner, BrK tabletting detects, and infared spectrum is as it is shown on figure 3, consistent with Fig. 2 infared spectrum of bibliographical information. Contrast consistent with cupreol according to physicochemical property, fusing point, infrared spectrum, it is determined that for cupreol.
Embodiment two
Take 2000ml Fructus Aurantii Immaturus and extract garbage, 100 DEG C of normal pressure concentrations, obtain concentration 1.07g/cm3Concentrated solution 920ml, is cooled to 65 DEG C by concentrated solution, adds petroleum ether 920ml stirring solvent and extracts 60 minutes, stands 30 minutes, divide and take petroleum ether extraction layer in 65 DEG C of water-baths; Water layer repeats extracting operation 3 times with 920ml petroleum ether again, petroleum ether extraction liquid will be had to merge, stand 2 hours. And 600g chromatographic silica gel wet method appropriate with petroleum ether fills post. Extract is joined in silicagel column, controlled post speed, extract is crossed after post completes with the petroleum ether of 9:1: ethyl acetate mixture mixed solvent eluting, and detection is sent out in eluent crystallization to be had and collect eluent during sitosterol and can't check sitosterol to eluent, collects eluent 9000ml altogether. Eluent containing sitosterol is heated and has been concentrated into crystallization; Concentrated solution is cooled to 20 DEG C, stands crystallization 8 hours, crystallization, sucking filtration, and 80 DEG C dry to obtain crude product 26.4g. Taking 95% ethanol 212g and add 26.4g crude product, agitating heating refluxes 2 hours, filtered while hot, when filtrate 85 DEG C is concentrated into original volume 1/10, stops heating, is cooled to 5 DEG C, and insulation stands 24 hours. Crystal solution sucking filtration, filter cake washing with alcohol, drain and flow out to without filtrate. Crystallization after sucking filtration, in 85 DEG C of drying, obtains product 19.1g, HPLC detection level 98.0%.
Embodiment three
Take 2000ml Fructus Aurantii Immaturus and extract garbage, 100 DEG C of normal pressure concentrations, obtain concentration 1.08g/cm3Concentrated solution 820ml, is cooled to 60 DEG C by concentrated solution, adds hexamethylene 820ml stirring solvent and extracts 60 minutes, stands 30 minutes, divide and take hexamethylene extract layer in 65 DEG C of water-baths; Water layer repeats extracting operation 3 times with 820ml hexamethylene again, hexamethylene extract will be had to merge, stand 2 hours. And 600g chromatographic silica gel wet method appropriate with hexamethylene fills post. Extract is joined in silicagel column, controlled post speed, extract is crossed after post completes with the hexamethylene of 95:5: ethyl acetate mixture mixed solvent eluting, and detection is sent out in eluent crystallization to be had and collect eluent during sitosterol and can't check sitosterol to eluent, collects eluent 7300ml altogether. Eluent containing sitosterol is heated and has been concentrated into crystallization; Concentrated solution is cooled to 20 DEG C, stands crystallization 8 hours, crystallization, sucking filtration, and 80 DEG C dry to obtain crude product 23.8g. Taking 95% ethanol 190g and add 23.8g crude product, agitating heating refluxes 1 hour, filtered while hot, when filtrate 85 DEG C is concentrated into original volume 1/10, stops heating, is cooled to 5 DEG C, and insulation stands 24 hours. Crystal solution sucking filtration, filter cake washing with alcohol, drain and flow out to without filtrate. Crystallization after sucking filtration, in 85 DEG C of drying, obtains product 17.8g, HPLC detection level 98.1%.
Claims (9)
1. extract, from Fructus Aurantii Immaturus, the method separating sitosterol garbage, comprise the following steps:
(A) offal treatment: take Fructus Aurantii Immaturus and separate the concentrated solution of Hesperidin after alcohol extraction, this effluent solution is being concentrated into concentration 1.02-1.12g/cm3, it is preferable that 1.05-1.10g/cm3;
(B) extracting: the garbage processed adds standing after organic stirring solvent extracts, and separates organic layer, optionally water layer repeats aforesaid operations one or many with organic solvent again, is merged by the extract of organic facies, stands;
(C) chromatography: extract peroxidating aluminum or silica gel column chromatography are adsorbed, crosses eluting after post completes, collects the eluent containing sitosterol;
(D) eluent concentration, crystallization, dry: the eluent containing sitosterol has been concentrated into crystallization; Concentrated solution is lowered the temperature, stands crystallization, crystallization sucking filtration, dry to obtain crude product;
(E) refining: the crude product that step (D) produces adds ethanol, it is heated to reflux dissolving, filters, filtrate is concentrated into original volume 1/3-1/12, it is preferable that 1/5-1/10;
(F) secondary crystallization, dry: concentrated solution stirring cooling, stands crystallization; Crystallization sucking filtration, washing, drain, then dry, it is thus achieved that product.
2. method according to claim 1, wherein, it is by after Fructus Aurantii Immaturus alcohol extraction Neosynephrine that Fructus Aurantii Immaturus separates the concentrated solution of Hesperidin after alcohol extraction, extract slag alcohol aqueous slkali to extract, then adjusting pH to acid, precipitate out Hesperidin, mother liquor concentrations reclaims the concentration residual liquid obtained after alcohol.
3. method according to claim 1 and 2, wherein, the concentration in step (A) is to concentrate at 95-100 DEG C of normal pressure.
4. the method according to any one of claim 1-3, wherein, in step (B), extraction organic solvent is selected from ethers (such as petroleum ether, diisobutyl ether, n-butyl ether) or hydro carbons (including chain hydro carbons, ring-type hydro carbons, for instance normal hexane, hexamethylene).
5. the method according to any one of claim 1-4, wherein, the extraction of step (B) is to heat to 60-65 DEG C at the effluent solution processed, add organic solvent such as ethers (such as petroleum ether, diisobutyl ether, n-butyl ether) or hydro carbons (such as normal hexane, hexamethylene) stirring extracts 30 minutes ~ 2 hours, preferably about 60 minutes, stand 15 minutes ~ 1 hour, preferably about 30 minutes, separate organic layer, water layer repeats aforesaid operations 2-3 time with organic solvent again, the extract of organic facies is merged, stand 1 ~ 4 hour, it is preferable that about 2 hours.
6. the method according to any one of claim 1-5, wherein, the chromatography of step (C) includes adsorbing extract peroxidating aluminum or silica gel column chromatography, cross after post completes with the petroleum ether ethyl acetate mixture of 9:1 or 95:5 cyclohexane ethyl acetate mixed solvent eluting, collect the eluent containing sitosterol.
7. the method according to any one of claim 1-6, wherein, the eluent concentration of step (D), crystallization, dry includes the eluent containing sitosterol has been concentrated into crystallization; Concentrated solution is cooled to 20-25 DEG C, stands crystallization 8 hours, crystallization sucking filtration, and 80 DEG C dry to obtain crude product.
8. the method according to any one of claim 1-7, wherein, refining the including of step (E): the crude product that step (D) produces adds crude product weight 6-10 times, the preferably 90-95% ethanol of 8 times, being heated to reflux 1-2h to dissolve, filter, filtrate 80-90 DEG C is concentrated into original volume 1/5-1/10.
9. the method according to any one of claim 1-8, wherein, concentrated solution stirring is cooled to 5-10 DEG C by the secondary crystallization of step (F), dry including, and stands crystallization 12-24h; Crystallization sucking filtration, washing with alcohol, drain; Crystallization 75 DEG C-95 DEG C after sucking filtration, it is preferable that about 85 DEG C of drying, obtain product.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116003366A (en) * | 2022-12-30 | 2023-04-25 | 陕西嘉禾药业有限公司 | Method for preparing nobiletin from immature bitter orange |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101475622A (en) * | 2009-01-19 | 2009-07-08 | 浙江工业大学 | Method for extracting phytosterin from residues after extracting vitamin E |
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- 2015-12-31 CN CN201511013964.0A patent/CN105669812A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101475622A (en) * | 2009-01-19 | 2009-07-08 | 浙江工业大学 | Method for extracting phytosterin from residues after extracting vitamin E |
Non-Patent Citations (2)
| Title |
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| 李敏: "枳壳化学成分的研究", 《吉林大学硕士学位论文》 * |
| 董丽荣: "枸橼果实化学成分研究", 《精细化工》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116003366A (en) * | 2022-12-30 | 2023-04-25 | 陕西嘉禾药业有限公司 | Method for preparing nobiletin from immature bitter orange |
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Application publication date: 20160615 |