CN114031662A - Preparation method of ergosterol - Google Patents
Preparation method of ergosterol Download PDFInfo
- Publication number
- CN114031662A CN114031662A CN202111567794.6A CN202111567794A CN114031662A CN 114031662 A CN114031662 A CN 114031662A CN 202111567794 A CN202111567794 A CN 202111567794A CN 114031662 A CN114031662 A CN 114031662A
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- China
- Prior art keywords
- ergosterol
- toluene
- concentration
- temperature
- preparation
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- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 title claims abstract description 37
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 title claims abstract description 37
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 title claims abstract description 37
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 title claims abstract description 37
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 20
- 239000003513 alkali Substances 0.000 claims abstract description 13
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011780 sodium chloride Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000007127 saponification reaction Methods 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 7
- 229930003316 Vitamin D Natural products 0.000 abstract description 5
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 abstract description 5
- 239000012847 fine chemical Substances 0.000 abstract description 5
- 239000011710 vitamin D Substances 0.000 abstract description 5
- 235000019166 vitamin D Nutrition 0.000 abstract description 5
- 150000003710 vitamin D derivatives Chemical class 0.000 abstract description 5
- 229940046008 vitamin d Drugs 0.000 abstract description 5
- 238000009776 industrial production Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 239000013064 chemical raw material Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 238000007670 refining Methods 0.000 abstract 1
- 239000011653 vitamin D2 Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a preparation method for producing ergosterol by using yeast in the technical field of fine chemical engineering, which comprises the steps of mixing the yeast with alkali and sodium chloride solution, saponifying, extracting by toluene, washing by water, concentrating, refining and drying in vacuum to obtain the finished product of ergosterol. The preparation method of the ergosterol realizes the industrial production of the ergosterol by utilizing common chemical raw material auxiliary materials such as yeast, alkali, sodium chloride, toluene, active carbon, ethanol and the like and common chemical equipment, has very simple and convenient production process and low production cost, wherein the toluene has slow volatilization speed which is 1/3 times of the volatilization speed of the toluene, and the purity and the yield of the ergosterol are effectively improved by reasonably selecting the proportion of each solution and controlling the temperature, thereby being capable of producing the vitamin D on a large scale2Provides raw material guarantee.
Description
Technical Field
The invention relates to the technical field of fine chemical engineering, in particular to a preparation method of ergosterol.
Background
Ergosterol is the most important phytosterol, is present in yeast and some plants, and when it is irradiated by ultraviolet rays, one of the four carbon rings in the molecule is broken down to become vitamin D2It is an industrial mass production of vitamin D2The main raw materials of (1). Due to vitamin D2Is one of the trace organic compounds necessary for human and animal to maintain normal life activity and health, and vitamin D may be added into medicine, food and feed2To satisfy the need for regular ingestion by a human or animal from the outside. Vitamin D2At present, the annual consumption of the feed additive is 1800 tons all over the world, about 70 percent of the annual consumption is used for the feed additive, the annual demand of China is more than 100 tons, and the vitamin D is used in China2The annual production and sales of about 1 ton, most of which need to be imported, except for technical reasonsThe insufficient supply of the canthasterol raw material is also an important reason for the low yield. "ever in China" fermentation method for producing vitamin D2"set up the national level project of key scientific and technical official customs, utilize waste mycelium of penicillin to extract ergosterol, can extract 4kg ergosterol by each ton of waste mycelium of penicillin theoretically, but the device that can produce ergosterol on a large scale industrially has not been built up yet at present. A manual of fine chemical products (Fine chemical products Manual) 10 th minute book of biochemistry (written by Zhou Zhi, Ding hong, Bai Xiao hong, Bi Xiao Ping, guan Wen Zhi, etc., 11 th edition in 2002, published by chemical industry publishers and fine chemical publishers center at 1 st edition) introduces ergosta 82% -84% ethanol leaching for 18-24, keeps the temperature at 70 ℃ for 3h, continuously stirs, filtering at the temperature of below 30 ℃, vacuum concentrating at the temperature of 70 ℃ to obtain paste, adding 5-10% of water and 3-5 times of diethyl ether into the paste, violently stirring for 2-3 h, and putting the paste in a refrigerator at the temperature of-5 ℃ to separate out ergosterol crystals; the human body can lose consciousness and even die, and is flammable and explosive; the low temperature condition of-5 ℃ increases the cost, so the method is difficult to realize industrial production, and the yield of the ergosterol is low.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a preparation method of ergosterol, the production process of the invention is very simple and convenient, the production cost is low, and the purity and the yield of the ergosterol are effectively improved by reasonably selecting the proportion of each solution and controlling the temperature, so that the vitamin D can be produced on a large scale2Provides raw material guarantee.
In order to achieve the above purpose, the solution adopted by the invention is as follows: the preparation method of ergosterol comprises the following steps:
a. putting alkali and sodium chloride into a saponification pot, adding yeast powder under stirring, wherein the ratio of the yeast powder to the alkali to the sodium chloride is 1 (0.5-0.8) to 0.4-0.6, keeping the temperature at 110-120 ℃ during saponification, and performing saponification reaction for 13-14 h;
b. extracting the saponified solution with toluene at a ratio of 1: 1.6-2 at 70-80 ℃;
c. washing the extracted toluene feed liquid with water to ensure that the toluene feed liquid is clear and transparent;
d. putting the toluene feed liquid into a concentration pot for concentration, controlling the temperature in the concentration pot to be 100-105 ℃, controlling the temperature in a primary concentration pot to be 70-85 ℃, controlling the flow properly, not performing concentration too quickly, performing concentration slowly, stopping performing primary concentration until the total volume is 100-120 liters, cooling, adding ethanol for dissolution, standing and crystallizing to obtain an ergosterol crude product;
e. and (3) dissolving the ergosterol crude product into a mixed solvent (1:3) of toluene and ethanol, filtering by using activated carbon, and drying in vacuum to obtain an ergosterol finished product.
The concentrator in the step d is a membrane concentrator.
The alkali used in the step a is sodium hydroxide and potassium hydroxide, and the temperature of the washing water used in the step c is 110-120 ℃.
The invention has the beneficial effects that: the preparation method of the ergosterol realizes the industrial production of the ergosterol by utilizing common chemical raw material auxiliary materials such as yeast, alkali, sodium chloride, toluene, active carbon, ethanol and the like and common chemical equipment, has very simple and convenient production process and low production cost, wherein the toluene has the characteristics of low price, low boiling point, easy removal of toxicity and the like, and effectively improves the purity and the yield of the ergosterol by reasonably selecting the proportion of each solution and controlling the temperature, thereby being capable of producing the vitamin D on a large scale2Provides raw material guarantee.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The technical solution of the present invention is further defined below with reference to the specific embodiments, but the scope of the claims is not limited to the description.
The preparation method of ergosterol comprises the following steps:
a. putting alkali and sodium chloride into a saponification pot, adding yeast powder under stirring, wherein the ratio of the yeast powder to the alkali to the sodium chloride is 1:0.6:0.6, keeping the temperature at 115 ℃ during saponification, and selecting the saponification reaction time to be 14h in the embodiment to ensure that the saponification reaction is more complete; the reaction fullness can effectively ensure the yield of finished products and the utilization rate of raw materials.
b. Extracting the saponified solution with toluene at a ratio of 1:2 and an extraction temperature of 80 ℃, so that the extraction fullness can be better guaranteed and the yield can be improved;
c. washing the extracted toluene feed liquid with water to ensure that the toluene feed liquid is clear and transparent; the content of the product after reaction is reduced, so that the purity of the finished product is improved;
d. concentrating the toluene liquid in a concentrating pan, controlling the temperature in the concentrating pan to be 105 ℃, controlling the temperature in the primary concentrating pan to be 80 ℃, controlling the flow to be proper, not being suitable for over-quick concentration, slowly performing the primary concentration until the total volume is 110 liters, stopping the primary concentration, cooling, adding ethanol for dissolving, standing and crystallizing to obtain an ergosterol crude product;
e. and (3) dissolving the ergosterol crude product into a mixed solvent (1:3) of toluene and ethanol, filtering by using activated carbon, and drying in vacuum to obtain an ergosterol finished product.
It is preferred. The concentrator in the step d is a membrane concentrator.
Preferably, the alkali used in step a is sodium hydroxide and potassium hydroxide, and the temperature of the washing water used in step c is 120 ℃.
The preparation method of the ergosterol realizes the industrial production of the ergosterol by utilizing common chemical raw material auxiliary materials such as yeast, alkali, sodium chloride, toluene, active carbon, ethanol and the like and common chemical equipment, has very simple and convenient production process and low production cost, wherein the toluene has the characteristics of low price, low boiling point, easy removal of toxicity and the like, and effectively extracts the ergosterol by reasonably selecting the proportion of each solution and controlling the temperatureThe purity and yield of ergosterol are improved, thereby being suitable for mass production of vitamin D2Provides raw material guarantee.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. 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 (3)
1. The preparation method of ergosterol is characterized in that: the method comprises the following steps:
a. putting alkali and sodium chloride into a saponification pot, adding yeast powder under stirring, wherein the ratio of the yeast powder to the alkali to the sodium chloride is 1 (0.5-0.8) to 0.4-0.6, keeping the temperature at 110-120 ℃ during saponification, and performing saponification reaction for 13-14 h;
b. extracting the saponified solution with toluene at a ratio of 1: 1.6-2 at 70-80 ℃;
c. washing the extracted toluene feed liquid with water to ensure that the toluene feed liquid is clear and transparent;
d. putting the toluene feed liquid into a concentration pot for concentration, controlling the temperature in the concentration pot to be 100-105 ℃, controlling the temperature in a primary concentration pot to be 70-85 ℃, controlling the flow properly, not performing concentration too quickly, performing concentration slowly, stopping performing primary concentration until the total volume is 100-120 liters, cooling, adding ethanol for dissolution, standing and crystallizing to obtain an ergosterol crude product;
e. and (3) dissolving the ergosterol crude product into a mixed solvent (1:3) of toluene and ethanol, filtering by using activated carbon, and drying in vacuum to obtain an ergosterol finished product.
2. A process for the preparation of ergosterol according to claim 1, characterized in that: the concentrator in the step d is a membrane concentrator.
3. A process for the preparation of ergosterol according to claim 1, characterized in that: the alkali used in the step a is sodium hydroxide and potassium hydroxide, and the temperature of the washing water used in the step c is 110-120 ℃.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310212788.1A CN116143860A (en) | 2021-12-20 | 2021-12-20 | Method for efficiently extracting ergosterol |
| CN202111567794.6A CN114031662A (en) | 2021-12-20 | 2021-12-20 | Preparation method of ergosterol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111567794.6A CN114031662A (en) | 2021-12-20 | 2021-12-20 | Preparation method of ergosterol |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310212788.1A Division CN116143860A (en) | 2021-12-20 | 2021-12-20 | Method for efficiently extracting ergosterol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114031662A true CN114031662A (en) | 2022-02-11 |
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310212788.1A Pending CN116143860A (en) | 2021-12-20 | 2021-12-20 | Method for efficiently extracting ergosterol |
| CN202111567794.6A Pending CN114031662A (en) | 2021-12-20 | 2021-12-20 | Preparation method of ergosterol |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310212788.1A Pending CN116143860A (en) | 2021-12-20 | 2021-12-20 | Method for efficiently extracting ergosterol |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN116143860A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1733930A (en) * | 2005-08-29 | 2006-02-15 | 勐永药业公司 | Ergosterol preparation method |
| CN1765916A (en) * | 2004-10-25 | 2006-05-03 | 陈国苹 | Ergosterol preparation method |
| CN113045618A (en) * | 2021-03-19 | 2021-06-29 | 河北华旭化工有限公司 | Process for extracting ergosterol from penicillin fermentation mycelium and preparing microecology |
-
2021
- 2021-12-20 CN CN202310212788.1A patent/CN116143860A/en active Pending
- 2021-12-20 CN CN202111567794.6A patent/CN114031662A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1765916A (en) * | 2004-10-25 | 2006-05-03 | 陈国苹 | Ergosterol preparation method |
| CN1733930A (en) * | 2005-08-29 | 2006-02-15 | 勐永药业公司 | Ergosterol preparation method |
| CN113045618A (en) * | 2021-03-19 | 2021-06-29 | 河北华旭化工有限公司 | Process for extracting ergosterol from penicillin fermentation mycelium and preparing microecology |
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| Publication number | Publication date |
|---|---|
| CN116143860A (en) | 2023-05-23 |
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Application publication date: 20220211 |
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