CN115215918A - Oryzanol monohydrate crystal form and preparation method thereof - Google Patents
Oryzanol monohydrate crystal form and preparation method thereof Download PDFInfo
- Publication number
- CN115215918A CN115215918A CN202210982223.7A CN202210982223A CN115215918A CN 115215918 A CN115215918 A CN 115215918A CN 202210982223 A CN202210982223 A CN 202210982223A CN 115215918 A CN115215918 A CN 115215918A
- Authority
- CN
- China
- Prior art keywords
- oryzanol
- monohydrate
- crystal form
- crystalline form
- preparing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000004682 monohydrates Chemical class 0.000 title claims abstract description 37
- 239000013078 crystal Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000008213 purified water Substances 0.000 claims abstract description 13
- 238000001035 drying Methods 0.000 claims abstract description 12
- 238000002425 crystallisation Methods 0.000 claims abstract description 10
- 230000008025 crystallization Effects 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- XZEUYTKSAYNYPK-UHFFFAOYSA-N 3beta-29-Norcycloart-24-en-3-ol Natural products C1CC2(C)C(C(CCC=C(C)C)C)CCC2(C)C2CCC3C(C)C(O)CCC33C21C3 XZEUYTKSAYNYPK-UHFFFAOYSA-N 0.000 claims abstract description 4
- RRTBTJPVUGMUNR-UHFFFAOYSA-N Cycloartanol Natural products C12CCC(C(C(O)CC3)(C)C)C3C2(CC)CCC2(C)C1(C)CCC2C(C)CCCC(C)C RRTBTJPVUGMUNR-UHFFFAOYSA-N 0.000 claims abstract description 4
- HVXLSFNCWWWDPA-UHFFFAOYSA-N Isocycloartenol Natural products C1CC(O)C(C)(C)C2C31CC13CCC3(C)C(C(CCCC(C)=C)C)CCC3(C)C1CC2 HVXLSFNCWWWDPA-UHFFFAOYSA-N 0.000 claims abstract description 4
- HXQRIQXPGMPSRW-UHZRDUGNSA-N Pollinastanol Natural products O[C@@H]1C[C@H]2[C@@]3([C@]4([C@H]([C@@]5(C)[C@@](C)([C@H]([C@H](CCCC(C)C)C)CC5)CC4)CC2)C3)CC1 HXQRIQXPGMPSRW-UHZRDUGNSA-N 0.000 claims abstract description 4
- ONQRKEUAIJMULO-YBXTVTTCSA-N cycloartenol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@@H](CCC=C(C)C)C)CC[C@@]3(C)[C@@H]1CC2 ONQRKEUAIJMULO-YBXTVTTCSA-N 0.000 claims abstract description 4
- YNBJLDSWFGUFRT-UHFFFAOYSA-N cycloartenol Natural products CC(CCC=C(C)C)C1CCC2(C)C1(C)CCC34CC35CCC(O)C(C)(C)C5CCC24C YNBJLDSWFGUFRT-UHFFFAOYSA-N 0.000 claims abstract description 4
- FODTZLFLDFKIQH-UHFFFAOYSA-N cycloartenol trans-ferulate Natural products C1=C(O)C(OC)=CC(C=CC(=O)OC2C(C3CCC4C5(C)CCC(C5(C)CCC54CC53CC2)C(C)CCC=C(C)C)(C)C)=C1 FODTZLFLDFKIQH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 230000002124 endocrine Effects 0.000 claims description 3
- 210000005036 nerve Anatomy 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000000932 sedative agent Substances 0.000 claims description 2
- 230000001624 sedative effect Effects 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 241000209094 Oryza Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 4
- 229940114124 ferulic acid Drugs 0.000 description 4
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 4
- 235000001785 ferulic acid Nutrition 0.000 description 4
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 ferulic acid ester Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000019774 Rice Bran oil Nutrition 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000008165 rice bran oil Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 208000001407 Vascular Headaches Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 210000000467 autonomic pathway Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001272 neurogenic effect Effects 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- 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)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention relates to the technical field of medicine preparation, in particular to a monohydrate crystal form of oryzanol and a preparation method thereof. The structural formula is shown as the following formula I:
the A is phytosterol taking cycloartenol as a main body. The preparation method comprises the following steps: putting the oryzanol into a reaction kettle, adding an organic solvent, controlling the temperature, stirring until the oryzanol is completely dissolved, adding purified water into the solution, uniformly stirring, cooling, continuously stirring until crystallization, filtering, washing, and drying under reduced pressure to obtain the oryzanol monohydrate crystal form. The crystal form of the oryzanol monohydrate prepared by the invention has the advantages of high yield, stable crystal form, high solubility, difficult moisture absorption, cheap and easily available raw materials, less three wastes, environmental protection, good controllability and suitability for large-scale industrial production.
Description
Technical Field
The invention relates to the technical field of medicine preparation, in particular to a monohydrate crystal form of oryzanol and a preparation method thereof.
Background
Chemical name of oryzanol: mixture of ferulic acid ester with cycloartenyl as main component and molecular formula of C 40 H 58 O 4 Molecular weight 602.8861, formula:
Oryzanol is the combined lipid of ferulic acid and phytosterol, and can be extracted from grain oil such as rice bran oil and germ oil. The appearance is color crystal powder, has no smell and special fragrance, can be dissolved in various oils and fats under heating, and is not dissolved in water. The oryzanol is mainly present in the raw bran oil and oil residue thereof, and the content of the oryzanol in the rice bran layer is 0.3-0.5%. The oryzanol is dissolved in the oil when Wen Yazha is added to the rice bran, and the content of the oryzanol in the raw bran oil is about 2 to 3 percent. The content of the rice bran oil is slightly different with different climatic conditions of rice planting, rice varieties and process conditions of oil extraction of the rice bran, and the rice bran of the rice in the frigid zone contains higher oryzanol content than the rice in the tropical zone; high-temperature squeezing and solvent leaching to obtain oil, wherein the content of oryzanol in the crude oil is higher than that in the low-temperature squeezing. In many vegetable oil materials, such as corn germ oil, wheat germ oil, highland barley bran oil, rapeseed oil and the like, the content of oryzanol in the raw bran oil is the highest, so the oryzanol is mostly extracted from the raw bran oil. Oryzanol is often adopted clinically to improve the vegetative nerve function and endocrine regulation, and in addition, the oryzanol also has various physiological effects of oxidation resistance, aging resistance and the like.
The pharmacological and clinical effects of oryzanol are identified and confirmed in China to be autonomic nerve dysfunction, female climacteric syndrome, periodic psychosis, dysmenorrhea, premenstrual tension syndrome, vascular headache, arrhythmia, functional dyspepsia, infantile neurogenic pollakisuria, head trauma syndrome and the like, and the market prospect is very wide.
Oryzanol is a natural mixture consisting of ferulic acid ester mainly comprising cycloartenyl and ferulic acid ester of sterol. The crystal form of the oryzanol monohydrate crystal form is different due to different solvents, dissolution temperature and pH value during precipitation, the solubility and stability of the oryzanol in different crystal forms are different, and at present, no research related to the oryzanol crystal form exists in China.
Disclosure of Invention
The present invention is directed to solving at least one of the technical problems of the prior art, and therefore, an aspect of the present invention is to provide a crystalline monohydrate form of oryzanol, having the following structural formula i:
the A is phytosterol taking cycloartenol as a main body.
Preferably, the water content of the oryzanol monohydrate crystal form is 2.0-3.0%.
Preferably, the crystalline form of oryzanol monohydrate has an X-ray powder diffraction spectrum with diffraction peaks at 2 Θ values of 3.370, 6.760, 8.540, 10.740, 13.011, 13.230, 14.510, 16.370, 16.840, 17.270, 17.520, 18.520, 18.980, 21.390, 21.790, 24.240, 25.410.
Preferably, the X-ray powder diffraction pattern of the monohydrated crystal form of oryzanol is shown in fig. 1.
Preferably, the oryzanol monohydrate crystal form is used for preparing sedative sleep-aiding medicines for improving the vegetative nerve function and endocrine regulation.
Another object of the present invention is to provide a method for preparing a crystalline form of oryzanol monohydrate, comprising the steps of:
s1, putting oryzanol into a reaction kettle, adding an organic solvent, controlling the temperature, stirring until the oryzanol is completely dissolved, adding purified water into the solution, stirring uniformly, cooling, and continuously stirring until crystallization;
and S2, filtering, washing and drying the crystal obtained in the S1 under reduced pressure to obtain the oryzanol monohydrate crystal form.
Preferably, the organic solvent in S1 is one of C1 to C4 alcohols, ketones, or esters.
Preferably, the temperature in the step S1 is controlled to be 20-50 ℃, and the mixture is stirred until the oryzanol is completely dissolved, wherein the temperature is from room temperature to the reflux temperature of the solvent; cooling to-10-50 ℃ for crystallization, wherein the crystallization time is 2h.
Preferably, the mass ratio of the oryzanol to the solvent in the S1 is 1:1-20; the mass ratio of the solvent to the purified water in the S1 is 1.
Preferably, the S2 is washed with purified water; and in the S2, a double-cone rotary vacuum drier is used for drying, the drying temperature is 60-70 ℃, the pressure is reduced to 0.08-0.09 MPa, and the drying time is 8-12 h. The invention has the following beneficial effects:
the crystal form of the oryzanol monohydrate prepared by the invention has high yield, stable crystal form and high solubility, and is not easy to cause dampness.
The method has the advantages of cheap and easily-obtained raw materials, less three wastes, environmental protection, no use of heavy metal catalyst, no drug safety risk caused by excessive heavy metal in the finished product, no high-temperature high-pressure reaction, mild reaction conditions, simple required equipment, convenience in operation, good controllability and suitability for large-scale industrial production.
Additional aspects and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention.
Drawings
The above and/or additional aspects and advantages of the present invention will become apparent and readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings of which:
fig. 1 is an X-ray powder diffraction pattern of a crystalline monohydrate form of oryzanol of the present invention.
Detailed Description
In order that the above objects, features and advantages of the present invention can be more clearly understood, the present invention will be described in further detail with reference to the accompanying drawings and specific embodiments. It should be noted that the embodiments and features of the embodiments of the present application may be combined with each other without conflict.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, however, the present invention may be practiced otherwise than as specifically described and, therefore, the scope of the present invention is not limited by the specific embodiments disclosed below.
Example one
Putting 20g of oryzanol into a 250ml four-mouth bottle, adding 100ml of acetone, controlling the temperature to be 30 ℃ and stirring until the oryzanol is completely dissolved, adding 50ml of purified water into the solution, stirring uniformly, cooling to 10 ℃, continuously stirring until crystallization lasts for 2 hours, filtering, washing with 20g of purified water, putting into a reduced-pressure oven, reducing the pressure to 0.08MPa at 60 ℃, and drying for 8 hours to obtain 19.5g of oryzanol monohydrate crystal form with the yield of 95%.
Example two
Putting 20g of oryzanol into a 250ml four-mouth bottle, adding 100ml of methanol, controlling the temperature to be 50 ℃, stirring until the oryzanol is completely dissolved, adding 50ml of purified water into the solution, stirring uniformly, cooling to 0 ℃, continuously stirring until crystallization lasts for 2 hours, filtering, washing with 20g of purified water, putting into a reduced-pressure oven for 65 ℃, reducing the pressure to 0.09MPa, and drying for 10 hours to obtain 19.5g of oryzanol monohydrate crystal form, wherein the yield is 95%.
EXAMPLE III
Putting 20g of oryzanol into a 250ml four-mouth bottle, adding 100ml of ethyl acetate, controlling the temperature at 40 ℃, stirring until the oryzanol is completely dissolved, adding 50ml of purified water into the solution, stirring uniformly, cooling to 10 ℃, continuously stirring until crystallization lasts for 2 hours, filtering, washing with 20g of purified water, putting into a reduced-pressure oven at 70 ℃, reducing the pressure to 0.09MPa, and drying for 12 hours to obtain 19.5g of oryzanol monohydrate crystal form, wherein the yield is 95%.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and it is obvious to those skilled in the art that various modifications and variations can be made in the present invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A crystalline monohydrate form of oryzanol characterized by: the structural formula of the monohydrate crystal form of the oryzanol is shown as the following formula I:
the A is phytosterol taking cycloartenol as a main body.
2. The crystalline form of oryzanol monohydrate of claim 1, characterized in that: the water content of the oryzanol monohydrate crystal form is 2.0-3.0%.
3. The crystalline form of oryzanol monohydrate of claim 1, characterized in that: the X-ray powder diffraction spectrum of the monohydrate form of oryzanol has diffraction peaks at 2 theta values of 3.370, 6.760, 8.540, 10.740, 13.011, 13.230, 14.510, 16.370, 16.840, 17.270, 17.520, 18.520, 18.980, 21.390, 21.790, 24.240, 25.410.
4. The crystalline form of oryzanol monohydrate of claim 1, characterized in that: the X-ray powder diffraction pattern of the oryzanol monohydrate crystal form is shown in figure 1.
5. The crystalline form of oryzanol monohydrate of claim 1, characterized in that: the application of the oryzanol monohydrate crystal form in preparing sedative sleep-aiding medicines for improving the vegetative nerve function and endocrine regulation.
6. A preparation method of a monohydrate crystal form of oryzanol is characterized by comprising the following steps: the method comprises the following steps:
s1, putting oryzanol into a reaction kettle, adding an organic solvent, controlling the temperature, stirring until the oryzanol is completely dissolved, adding purified water into the solution, stirring uniformly, cooling, and continuously stirring until crystallization;
and S2, filtering, washing and drying the crystal obtained in the S1 under reduced pressure to obtain the oryzanol monohydrate crystal form.
7. The method for preparing the crystalline form of oryzanol monohydrate of claim 6, wherein the crystalline form of oryzanol monohydrate is selected from the group consisting of: the organic solvent in S1 is one of C1-C4 alcohols, ketones or esters.
8. The method for preparing the monohydrate crystal form of oryzanol as claimed in claim 6, wherein the method comprises the following steps: the temperature in the S1 is controlled to be 20-50 ℃, and the mixture is stirred until the oryzanol is completely dissolved; cooling to-10-50 ℃ for crystallization, wherein the crystallization time is 2h.
9. The method for preparing the crystalline form of oryzanol monohydrate of claim 6, wherein the crystalline form of oryzanol monohydrate is selected from the group consisting of: the mass ratio of the oryzanol to the solvent in the S1 is 1:1-20; the mass ratio of the solvent to the purified water in the S1 is 1.
10. The method for preparing the crystalline form of oryzanol monohydrate of claim 6, wherein the crystalline form of oryzanol monohydrate is selected from the group consisting of: washing with purified water in the S2; and in the S2, a double-cone rotary vacuum drier is used for drying, the drying temperature is 60-70 ℃, the pressure is reduced to 0.08-0.09 MPa, and the drying time is 8-12 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210982223.7A CN115215918A (en) | 2022-08-16 | 2022-08-16 | Oryzanol monohydrate crystal form and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210982223.7A CN115215918A (en) | 2022-08-16 | 2022-08-16 | Oryzanol monohydrate crystal form and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115215918A true CN115215918A (en) | 2022-10-21 |
Family
ID=83615594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210982223.7A Pending CN115215918A (en) | 2022-08-16 | 2022-08-16 | Oryzanol monohydrate crystal form and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115215918A (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008130449A2 (en) * | 2006-11-20 | 2008-10-30 | Satori Pharmaceuticals, Inc. | Modulators of amyloid-beta production |
| CN101313908A (en) * | 2007-05-31 | 2008-12-03 | 北京世纪博康医药科技有限公司 | Composition for treating autonomic nerve disorder, preparation and uses thereof |
| CN101480403A (en) * | 2008-12-17 | 2009-07-15 | 北京世纪博康医药科技有限公司 | Medicament composition and preparation method thereof |
| CN101596200A (en) * | 2008-06-02 | 2009-12-09 | 北京世纪博康医药科技有限公司 | A kind of composite preparation of cycloartenyl ferulate and purifying process |
| CN102058606A (en) * | 2011-01-11 | 2011-05-18 | 北京世纪博康医药科技有限公司 | Oryzanol medicinal composition |
| CN102311479A (en) * | 2010-07-08 | 2012-01-11 | 黑龙江万禾园油脂有限公司 | Method for extracting oryzanol by non-polar solvent extraction method |
| CN111620775A (en) * | 2020-06-04 | 2020-09-04 | 浙江得乐康食品股份有限公司 | Method for preparing cycloartenyl ferulate by selectively hydrolyzing oryzanol |
-
2022
- 2022-08-16 CN CN202210982223.7A patent/CN115215918A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008130449A2 (en) * | 2006-11-20 | 2008-10-30 | Satori Pharmaceuticals, Inc. | Modulators of amyloid-beta production |
| CN101313908A (en) * | 2007-05-31 | 2008-12-03 | 北京世纪博康医药科技有限公司 | Composition for treating autonomic nerve disorder, preparation and uses thereof |
| CN101596200A (en) * | 2008-06-02 | 2009-12-09 | 北京世纪博康医药科技有限公司 | A kind of composite preparation of cycloartenyl ferulate and purifying process |
| CN101480403A (en) * | 2008-12-17 | 2009-07-15 | 北京世纪博康医药科技有限公司 | Medicament composition and preparation method thereof |
| CN102311479A (en) * | 2010-07-08 | 2012-01-11 | 黑龙江万禾园油脂有限公司 | Method for extracting oryzanol by non-polar solvent extraction method |
| CN102058606A (en) * | 2011-01-11 | 2011-05-18 | 北京世纪博康医药科技有限公司 | Oryzanol medicinal composition |
| CN111620775A (en) * | 2020-06-04 | 2020-09-04 | 浙江得乐康食品股份有限公司 | Method for preparing cycloartenyl ferulate by selectively hydrolyzing oryzanol |
Non-Patent Citations (2)
| Title |
|---|
| HONG-FENG LUO 等: "Cytotoxic Hydroxylated Triterpene Alcohol Ferulates from Rice Bran", J.NAT.PROD. * |
| 张江帅 等: "谷维素提取及纯化方法研究进展", 粮油与油脂 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101607977B (en) | Method for extracting and purifying natural phytosterol from oil deodorization distillate residual oil and technique thereof | |
| CN105254603B (en) | The synthesis technique of SMIA | |
| CN100999698B (en) | Greasy of containing glycerin ester type conjugate linolic acid and production process thereof | |
| CN101701029A (en) | Method for extracting natural phytosterin from residual oil of vegetable fat deodorizing distillate | |
| WO2015018206A1 (en) | Method for preparing functional grease rich in phytosterol ester and diglyceride | |
| CN101845473A (en) | Method for effectively synthesizing phytosterol ester | |
| CN107827947B (en) | Method for extracting high-purity sterol from residual oil containing sterol ester | |
| CN104072259A (en) | Special high yield long-acting slow release compound fertilizer for sugarcane planting in dryland | |
| CN101774997B (en) | Method for completely and continuously extracting natural vitamin E and phytosterol | |
| CN101942007A (en) | Method for extracting phytosterol from waste residues generated in biodiesel production and product thereof | |
| CN115215918A (en) | Oryzanol monohydrate crystal form and preparation method thereof | |
| CN102559394A (en) | Low-calorie edible vegetable oil preparation technology | |
| CN104450209A (en) | Method for reducing acid value of crude rice bran oil through solid super acid catalysis | |
| CN102321068A (en) | Method for preparing strontium ranelate | |
| CN107573237B (en) | Method for preparing high-purity gossypol acetate in cotton oil refining process | |
| CN107722099A (en) | A kind of method that high-purity stigmasterol is prepared from phytosterols oletate | |
| CN108531538A (en) | A kind of method that enzyme process prepares phytosterin ester | |
| CN108018127A (en) | A kind of preparation method of unsaturation mono-fatty acid glyceride | |
| CN104072256B (en) | A kind of long-acting sustained-release complex fertilizer improving sesame quality | |
| CN101455399B (en) | Linoleate preparation method using highland barley bran oil | |
| CN111635347B (en) | Preparation method of high-color-value deodorized lutein ester | |
| CN104177467A (en) | Efficient synthesis and separation method of phytosterol ester | |
| CN110669089A (en) | Synthesis method of 6-ketoestradiol | |
| CN102964411B (en) | Synthesis method of androstane-4,6-diene-17 alpha-methyl-17 beta-alcohol-3-ketone | |
| CN105624215B (en) | Novel method for synthesizing calcipotriol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20221021 |
|
| RJ01 | Rejection of invention patent application after publication |