CN117024261A - Extraction method of coenzyme Q10 - Google Patents
Extraction method of coenzyme Q10 Download PDFInfo
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- CN117024261A CN117024261A CN202311012756.3A CN202311012756A CN117024261A CN 117024261 A CN117024261 A CN 117024261A CN 202311012756 A CN202311012756 A CN 202311012756A CN 117024261 A CN117024261 A CN 117024261A
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- 235000017471 coenzyme Q10 Nutrition 0.000 title claims abstract description 78
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 title claims abstract description 78
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 229940110767 coenzyme Q10 Drugs 0.000 title claims abstract description 76
- 238000000605 extraction Methods 0.000 title claims abstract description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 86
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 72
- 238000003756 stirring Methods 0.000 claims abstract description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000003208 petroleum Substances 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000000243 solution Substances 0.000 claims abstract description 35
- 239000012074 organic phase Substances 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000011259 mixed solution Substances 0.000 claims abstract description 30
- 239000000284 extract Substances 0.000 claims abstract description 24
- 238000001914 filtration Methods 0.000 claims abstract description 21
- 239000012071 phase Substances 0.000 claims abstract description 19
- 238000001816 cooling Methods 0.000 claims abstract description 17
- 238000000855 fermentation Methods 0.000 claims abstract description 15
- 230000004151 fermentation Effects 0.000 claims abstract description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 238000000967 suction filtration Methods 0.000 claims description 14
- 239000000469 ethanolic extract Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 238000009776 industrial production Methods 0.000 abstract description 3
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000010009 beating Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 241000233866 Fungi Species 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 238000001471 micro-filtration Methods 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 208000015606 cardiovascular system disease Diseases 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The application belongs to the technical field of biological pharmacy, and discloses a coenzyme Q10 extraction method, which comprises the steps of slowly adding coenzyme Q10 fermentation liquor into mixed liquor of petroleum ether and ethyl acetate, stirring, standing and layering to obtain aqueous phase and organic phase, concentrating the organic phase, repeatedly extracting with ethanol, and merging the extracting solutions to obtain mixed liquor containing coenzyme Q10; slowly adding petroleum ether into the mixed solution, stirring, standing to separate an organic phase and a water phase, concentrating the organic phase to obtain an extract, adding active carbon into the extract after dissolving the extract, stirring, and suction-filtering to obtain a decolorized solution, and cooling and suction-filtering the decolorized solution to obtain a coenzyme Q10 finished product. The extraction method has simple process and simple and convenient operation, can effectively reduce the operation cost, greatly shortens the production period, and lays a foundation for realizing large-scale industrial production.
Description
Technical Field
The application belongs to the technical field of biological pharmacy, and particularly relates to a method for extracting coenzyme Q10.
Background
Coenzyme Q10 is a fat-soluble antioxidant, has the functions of improving human immunity, enhancing antioxidation, delaying aging, enhancing human vitality and the like, is widely used for cardiovascular system diseases in medicine and is widely used for nutritional health-care products and food additives at home and abroad. The preparation method of the coenzyme Q10 mainly comprises three methods of animal and plant tissue extraction, chemical synthesis and microbial fermentation; wherein the animal and plant tissue extraction method has complicated conditions and high cost; the chemical synthesis method needs to separate cis-trans isomers, the addition of the separation components is less, and the microbial fermentation method is widely applied due to the advantages of low production cost, no isomer and the like.
The patent with publication number CN 115677468A discloses a purifying method of coenzyme Q10, which adopts plate and frame filtration, fungus dreg drying and other processes, the production equipment is difficult to match, the requirement on continuous operation equipment is high, the production process period is long, and new environmental protection problems are easy to occur in the steps of fungus dreg drying and the like.
The Chinese patent with the authority of CN107337593B relates to a preparation method of a pure product of coenzyme Q10, which comprises the following process steps: firstly, carrying out ceramic membrane microfiltration and spray drying on coenzyme Q10 fermentation liquor to obtain a crude product, then leaching the crude product with acetone, carrying out phase separation and reduced pressure concentration on the obtained leaching liquor to obtain coenzyme Q10 extraction concentrated liquor, then carrying out petroleum ether extraction, silica gel column chromatography and reduced pressure distillation concentration on eluent, finally adding coenzyme Q10 seed crystal for crystallization, and carrying out reduced pressure drying to obtain the pure product of coenzyme Q10. The application adopts ceramic membrane microfiltration and spray drying method to crush mycelium, then acetone reflux extraction and ceramic membrane filter separation are carried out, mycelium cell wall breaking and separation are carried out, and coenzyme Q10 is enriched. The crude extract of the coenzyme Q10 mainly contains coenzyme Q homologues with different numbers of isoamylene units on side chains, the coenzyme Q homologues have very similar properties to the coenzyme Q10, the separation difficulty of the coenzyme Q10 by a silica gel column chromatography technology is high, the solvent consumption is high, the time consumption is long, and the efficiency is low.
The application comprises the following steps:
the technical problems to be solved by the application are as follows: the extraction method of the coenzyme Q10 overcomes the defects in the prior art, has simple process, simple and convenient operation and low operation cost, can effectively reduce energy consumption and shorten production period, and lays a foundation for large-scale industrial production.
In order to solve the technical problems, the technical scheme of the application is as follows:
a method for extracting coenzyme Q10, comprising the following steps:
a. extraction: slowly adding a mixed solution of petroleum ether and ethyl acetate into the coenzyme Q10 fermentation broth according to the volume ratio of 5:1-3, continuously stirring at the same time, stirring for 1-3 hours at the rotating speed of 200-400 rpm, standing for 20-40 min, and separating an organic phase from a water phase after layering;
b. concentrating the organic phase in the step a at the temperature of 40-70 ℃ and the vacuum degree of-0.10 Mpa to-0.09 Mpa until no condensed water flows out to obtain a concentrated solution, repeatedly extracting the concentrated solution with ethanol for 3-5 times, adding ethanol under stirring at the rotating speed of 300-600 rpm each time, stirring for 1-3 hours at the temperature of 40-60 ℃ after the addition, filtering after the stirring is finished, filtering out ethanol extract, cooling to 8-12 ℃ to obtain mixed solution containing coenzyme Q10, and mixing the mixed solution obtained each time; the total addition amount of the ethanol is 1 to 3 times of the volume of the concentrated solution;
c. slowly adding petroleum ether into the mixed solution containing coenzyme Q10 obtained in the step b, wherein the volume ratio of the petroleum ether to the mixed solution is 1-3:1, continuously stirring in the adding process, stirring at the rotating speed of 300-800 rpm until the mixed solution is clear, standing for 1-3 h, separating an organic phase and a water phase, and controlling the titer of the water phase to be 0.5g/L;
d. concentrating the organic phase obtained in the step c at the temperature of 40-60 ℃ and the vacuum degree of-0.10 Mpa to-0.09 Mpa until no condensed water flows out to obtain extract;
e. and d, dissolving the extract obtained in the step d at 40-70 ℃, adding 0.1-0.5% of active carbon after dissolving and clarifying, stirring for 30min at 40-70 ℃ and 400-800 rpm, carrying out suction filtration to obtain decolorized solution, cooling the decolorized solution to 20-25 ℃ at 3-5 ℃/h, and carrying out suction filtration to obtain a coenzyme Q10 finished product.
Preferably, in the step a, the volume ratio of the coenzyme Q10 fermentation liquor to the mixed liquor of petroleum ether and ethyl acetate is 5:2, and the volume ratio of petroleum ether to ethyl acetate in the mixed liquor of petroleum ether and ethyl acetate is 10:3-5; stirring at 300rpm for 2h, and then standing for 30min.
Further, the volume ratio of petroleum ether to ethyl acetate in the petroleum ether and ethyl acetate mixed solution is 10:4.
Preferably, the organic phase in the step b is concentrated under the conditions of 55 ℃ and the vacuum degree of-0.095 Mpa; concentrating until no condensed water flows out to obtain concentrated solution, repeatedly extracting the concentrated solution with ethanol for 4 times, adding ethanol under stirring at 400rpm each time, stirring at 50deg.C for 2 hr after the addition, filtering after stirring, filtering to obtain ethanol extract, and cooling to 10deg.C; the total addition amount of ethanol is 2 times of the volume of the concentrated solution.
Preferably, in the step c, the volume ratio of the petroleum ether to the mixed solution is 2:1, and the petroleum ether and the mixed solution are continuously stirred in the adding process, stirred at the rotating speed of 500rpm until the petroleum ether and the mixed solution are clear, and then are kept stand for 2 hours.
Preferably, the organic phase in step d is concentrated at a temperature of 50℃and a vacuum of-0.095 MPa.
Preferably, the extract in the step e is dissolved at 55 ℃, 0.3% active carbon is added after dissolution and clarification, stirring is carried out for 30min at 55 ℃ and 600rpm, the decolorized solution is obtained by suction filtration, the decolorized solution is cooled to 22.5 ℃ at 4 ℃/h, and suction filtration is carried out.
Due to the adoption of the technical scheme, the application has the beneficial effects that:
1. the process adopted by the application eliminates the steps of plate frame filtration, fungus dreg drying, fungus dreg leaching and the like in the traditional process, thereby not only simplifying equipment, but also shortening production period, and simultaneously avoiding new pollution to the environment in the fungus dreg leaching process.
2. The solvent used in the application is ethyl acetate, petroleum ether and ethanol, and has the advantages of few types, low dosage and low harm to the environment.
3. The application adopts the ethanol crystallization mode to purify the coenzyme Q10 crude product, improves the quality of the coenzyme Q10 while ensuring the crystallization yield, and obtains the product with good crystal form and the content of more than or equal to 99.5 percent.
In a word, the extraction method has simple process and simple and convenient operation, can effectively reduce the operation cost, greatly shortens the production period, has low energy consumption because the used equipment is conventional equipment, and lays a foundation for realizing large-scale industrial production.
Detailed Description
The technical scheme of the application is further described below by combining examples:
example 1:
a. extraction: taking 1000L of coenzyme Q10 fermentation liquor, slowly adding 200L of mixed liquor of petroleum ether and ethyl acetate in a volume ratio of 5:1 (wherein the volume ratio of petroleum ether to ethyl acetate is 10:3), continuously stirring at the same time, stirring for 3 hours at 200rpm, standing for 40min, and separating an organic phase from a water phase after layering;
b. concentrating the organic phase in the step a at 40 ℃ under the condition of vacuum degree of-0.10 Mpa until no condensed water flows out to obtain a concentrated solution, adding ethanol under the stirring of 300rpm, extracting for 3 times, stirring for 3 hours at 40 ℃, filtering out an ethanol extract, mixing the three ethanol extracts, and cooling to 8 ℃ to obtain a mixed solution containing coenzyme Q10;
c. slowly adding petroleum ether into the coenzyme Q10 mixed solution, wherein the volume ratio of the petroleum ether to the mixed solution is 1:1, continuously stirring in the adding process, stirring at a rotating speed of 300rpm until the mixture is clear, standing for 3 hours, separating an organic phase from a water phase, and controlling the titer of the water phase to be 0.5g/L;
d. concentrating the organic phase obtained in the step c at 40 ℃ and vacuum degree of-0.10 Mpa until no condensed water flows out to obtain extract;
e. dissolving the extract obtained in the step d at 40 ℃, adding 0.1% active carbon after dissolving and clarifying, stirring for 30min at 40 ℃ and 400rpm, carrying out suction filtration to obtain a decolorized solution, cooling the decolorized solution to 25 ℃ at 3 ℃/h, and carrying out suction filtration to obtain 2160 g of finished product of coenzyme Q10, wherein the content of the coenzyme Q10 is 99.6%.
Example 2:
a. extraction: taking 1000L of coenzyme Q10 fermentation liquor, slowly adding 600L of mixed liquor of petroleum ether and ethyl acetate in a volume ratio of 5:3 (wherein the volume ratio of petroleum ether to ethyl acetate is 10:5), continuously stirring at the same time, stirring for 1h at 400rpm, standing for 20min, and separating an organic phase from a water phase after layering;
b. concentrating the organic phase in the step a at 70 ℃ under the condition of vacuum degree of-0.09 Mpa until no condensed water flows out to obtain a concentrated solution, adding ethanol under the stirring of 600rpm, extracting for 5 times, stirring for 1h at 60 ℃, filtering out an ethanol extract, mixing and cooling the ethanol extract for five times to 12 ℃ to obtain a mixed solution containing coenzyme Q10;
c. slowly adding petroleum ether into the obtained mixed solution containing coenzyme Q10, wherein the volume ratio of petroleum ether to the mixed solution is 3:1, continuously stirring in the adding process, stirring at 800rpm until the mixed solution is clear, standing for 1h, separating an organic phase from a water phase, and controlling the titer of the water phase to be 0.5g/L;
d. concentrating the organic phase obtained in the step c at 60 ℃ and vacuum degree of-0.09 Mpa until no condensed water flows out to obtain extract;
e. and d, dissolving the extract obtained in the step d at 70 ℃, adding 0.5% of activated carbon after dissolving and clarifying, stirring for 30min at 70 ℃ and 800rpm, carrying out suction filtration to obtain a decolorized solution, cooling the decolorized solution to 25 ℃ at 5 ℃/h, and carrying out suction filtration to obtain 2220 g of a finished product of coenzyme Q10, wherein the content of the coenzyme Q10 is 99.5%.
Example 3:
a. extraction: taking 1000L of coenzyme Q10 fermentation liquor, slowly adding 400L of mixed liquor of petroleum ether and ethyl acetate in a volume ratio of 5:2 (wherein the volume ratio of petroleum ether to ethyl acetate is 10:4), continuously stirring at 300rpm for 2 hours, standing for 30min, and separating an organic phase from a water phase after layering;
b. concentrating the organic phase in the step a at 55 ℃ and the vacuum degree of-0.095 Mpa until no condensed water flows out to obtain a concentrated solution, adding ethanol under the stirring of 400rpm, extracting for 4 times, stirring for 2 hours at 50 ℃, filtering out an ethanol extract, mixing the four ethanol extracts, and cooling to 10 ℃ to obtain a mixed solution containing coenzyme Q10;
c. slowly adding petroleum ether into the mixed solution of the coenzyme Q10, wherein the volume ratio of the petroleum ether to the mixed solution is 2:1, continuously stirring in the adding process, stirring at 500rpm until the mixture is clear, standing for 2 hours, separating an organic phase from a water phase, and controlling the titer of the water phase to be 0.5g/L;
d. concentrating the organic phase obtained in the step c at 50 ℃ and vacuum degree of-0.095 Mpa until no condensed water flows out to obtain extract;
e. and d, dissolving the extract obtained in the step d at 55 ℃, adding 0.3% of active carbon after dissolving and clarifying, stirring for 30min at 55 ℃ and 600rpm, carrying out suction filtration to obtain a decolorized solution, cooling the decolorized solution to 22.5 ℃ at 4 ℃/h, and carrying out suction filtration to obtain 2430 g of a finished product of the coenzyme Q10, wherein the content of the coenzyme Q10 is 99.8%.
Example 4:
and (c) removing the volume ratio of the coenzyme Q10 fermentation liquor to the ethyl acetate and petroleum ether mixed liquor in the extraction of the step a of 5: 2.5. Other process conditions were the same as in example 3, giving a coenzyme Q10 yield of 2280g, wherein the content of coenzyme Q10 was 99.5%.
Example 5
Except that the volume ratio of the coenzyme Q10 fermentation liquor to the ethyl acetate and petroleum ether mixed liquor in the extraction of the step a is 5:1.5. Other process conditions were the same as in example 3, giving a coenzyme Q10 yield of 2265g, wherein the content of coenzyme Q10 was 99.6%.
Example 6
The process conditions were the same as in example 3 except that the volume ratio of the mixed solution and petroleum ether in step c was 1:3, to obtain 2190g of coenzyme Q10 as a final product, wherein the content of coenzyme Q10 was 99.5%.
Comparative example 1: method for extracting coenzyme Q10 in prior art
10kg of wet mycelium with the water content of about 60% is weighed, 10L of prepared sodium sulfite aqueous solution is added, beating is carried out under vigorous stirring, 50L of normal hexane and 1kg of dodecyl trimethyl ammonium chloride are added, and beating extraction is carried out continuously for 6 hours under the temperature condition of 40 ℃ after the addition. Adding 1L saturated sodium chloride solution, stirring thoroughly, transferring to a liquid separating device, standing, removing water phase, washing an organic phase with saturated sodium chloride aqueous solution (1L multiplied by 3), drying the organic phase with anhydrous sodium sulfate, filtering, spin-drying the solvent to obtain extract, separating the extract by 200-300 silica gel column chromatography, separating the silica gel by 10 times of the mass of the extract, eluting with 1% acetone and n-hexane mixed solvent by volume ratio, mixing eluent containing coenzyme Q10, spin-drying the solvent, adding 60 ℃ absolute ethanol to dissolve again, controlling the crystallization temperature to drop by 2 ℃ every hour, slowly cooling to 0 ℃ and maintaining for 3 hours, filtering, washing, and drying to obtain 102.1g of finished product with purity of 99.0%.
Comparative example 2: method II for extracting coenzyme Q10 in prior art
10kg of wet mycelium with the water content of about 50% is weighed, 10L of prepared sodium sulfite aqueous solution is added, beating is carried out under vigorous stirring, 50L of n-hexane and 1kg of dodecyl trimethyl ammonium chloride are added, and beating extraction is carried out continuously for 7 hours under the temperature condition of 30 ℃ after the addition. Adding 1L saturated sodium chloride solution, stirring thoroughly, transferring into a liquid separating device, standing, removing water phase, washing an organic phase with saturated sodium chloride aqueous solution (1L multiplied by 3), drying the organic phase with anhydrous sodium sulfate, filtering, spin-drying the solvent to obtain extract, separating the extract by 200-300 silica gel column chromatography, mixing the mixed solvent of acetone and n-hexane with the mass of silica gel being 10 times of the extract, eluting with the volume ratio of 0.8%, mixing the eluent containing coenzyme Q10, spin-drying the solvent, adding 60 ℃ absolute ethyl alcohol to dissolve again, controlling the crystallization temperature to drop by 2 ℃ every hour, slowly cooling to 0 ℃ and maintaining for 3 hours, obtaining a large amount of crystals, filtering, washing, and drying to obtain 105.1g of finished product with the purity of 98.9%.
Comparative example 3: method III for extracting coenzyme Q10 in prior art
10kg of wet mycelium with the water content of about 70% is weighed, 10L of prepared sodium sulfite aqueous solution is added, beating is carried out under vigorous stirring, 50L of n-hexane and 1kg of dodecyl trimethyl ammonium chloride are added, and beating extraction is carried out continuously for 5 hours under the temperature condition of 50 ℃ after the addition. Adding 1L saturated sodium chloride solution, stirring thoroughly, transferring into a liquid separating device, standing, removing water phase, washing the organic phase with saturated sodium chloride aqueous solution (1L multiplied by 3), drying the organic phase with anhydrous sodium sulfate, filtering, spin-drying the solvent to obtain extract, separating the extract by 200-300 silica gel column chromatography, mixing the mixed solvent of acetone and n-hexane with the mass of silica gel being 10 times of the extract, eluting with the volume ratio of 1.5%, mixing the eluent containing coenzyme Q10, spin-drying the solvent, adding 60 ℃ absolute ethanol to dissolve again, controlling the crystallization temperature to drop by 2 ℃ every hour, slowly cooling to 0 ℃ and maintaining for 3 hours, obtaining a large amount of crystals, filtering, washing, and drying to obtain 103.g of finished product with the purity of 99.1%.
Results and analysis:
the products of examples 1-6 and comparative examples 1-3 were analyzed and the data are shown in Table 1:
TABLE 1 data for the detection of the products of examples 1-6 and comparative examples 1-3
| Yield (%) | Coenzyme Q10 content (%) | |
| Example 1 | 72.0％ | 99.6％ |
| Example 2 | 74.0％ | 99.5％ |
| Example 3 | 81.0％ | 99.8％ |
| Example 4 | 76.0％ | 99.5％ |
| Example 5 | 75.5％ | 99.6％ |
| Example 6 | 73.0％ | 99.5％ |
| Comparative example 1 | 50.6％ | 99.0％ |
| Comparative example 2 | 52.0％ | 98.9％ |
| Comparative example 3 | 51.5％ | 99.1％ |
From the above results, it can be seen that the yield of example 3 of the present application is highest, and the content of coenzyme Q10 is relatively high, so that the reaction conditions are relatively good; using the reaction conditions of example 3, changing the volume ratio of the fermentation liquor to the mixed liquor of ethyl acetate and petroleum ether in the step a, finding that the yield of coenzyme Q10 is obviously reduced, indicating that the volume ratio of the fermentation liquor to the mixed liquor of ethyl acetate and petroleum ether is an important parameter; changing the volume ratio of the mixed liquor and petroleum ether in the step c shows that the yield of coenzyme Q10 is also obviously reduced, which indicates that the volume ratio of the mixed liquor and petroleum ether is also an important parameter.
As can be seen by comparing with the prior art extraction of coenzyme Q10, the yield of coenzyme Q10 of the prior art is much lower than that of the present application, and the content of coenzyme Q10 is also significantly lower than that of the present application.
It is to be understood that these examples are illustrative of the present application and are not intended to limit the scope of the present application. Furthermore, it should be understood that various changes and modifications can be made by one skilled in the art after reading the teachings of the present application, and such equivalents are intended to fall within the scope of the application as defined in the appended claims.
Claims (7)
1. A method for extracting coenzyme Q10, comprising the steps of:
a. extraction: slowly adding a mixed solution of petroleum ether and ethyl acetate into the coenzyme Q10 fermentation broth according to the volume ratio of 5:1-3, continuously stirring at the same time, stirring for 1-3 hours at the rotating speed of 200-400 rpm, standing for 20-40 min, and separating an organic phase from a water phase after layering;
b. concentrating the organic phase in the step a at the temperature of 40-70 ℃ and the vacuum degree of-0.10 Mpa to-0.09 Mpa until no condensed water flows out to obtain a concentrated solution, repeatedly extracting the concentrated solution with ethanol for 3-5 times, adding ethanol under stirring at the rotating speed of 300-600 rpm each time, stirring for 1-3 hours at the temperature of 40-60 ℃ after the addition, filtering after the stirring is finished, filtering out ethanol extract, cooling to 8-12 ℃ to obtain mixed solution containing coenzyme Q10, and mixing the mixed solution obtained each time; the total addition amount of the ethanol is 1 to 3 times of the volume of the concentrated solution;
c. slowly adding petroleum ether into the mixed solution containing coenzyme Q10 obtained in the step b, wherein the volume ratio of the petroleum ether to the mixed solution is 1-3:1, continuously stirring in the adding process, stirring at the rotating speed of 300-800 rpm until the mixed solution is clear, standing for 1-3 h, separating an organic phase and a water phase, and controlling the titer of the water phase to be 0.5g/L;
d. concentrating the organic phase obtained in the step c at the temperature of 40-60 ℃ and the vacuum degree of-0.10 Mpa to-0.09 Mpa until no condensed water flows out to obtain extract;
e. and d, dissolving the extract obtained in the step d at 40-70 ℃, adding 0.1-0.5% of active carbon after dissolving and clarifying, stirring for 30min at 40-70 ℃ and 400-800 rpm, carrying out suction filtration to obtain decolorized solution, cooling the decolorized solution to 20-25 ℃ at 3-5 ℃/h, and carrying out suction filtration to obtain a coenzyme Q10 finished product.
2. The method for extracting coenzyme Q10 according to claim 1, wherein: the volume ratio of the coenzyme Q10 fermentation liquor to the mixed liquor of petroleum ether and ethyl acetate in the step a is 5:2, and the volume ratio of petroleum ether to ethyl acetate in the mixed liquor of petroleum ether and ethyl acetate is 10:3-5; stirring at 300rpm for 2h, and then standing for 30min.
3. The method for extracting coenzyme Q10 according to claim 2, wherein: and a volume ratio of petroleum ether to ethyl acetate in the mixed solution of petroleum ether and ethyl acetate in the step a is 10:4.
4. The method for extracting coenzyme Q10 according to claim 1, wherein: concentrating the organic phase in the step b at 55 ℃ and a vacuum degree of-0.095 Mpa; concentrating until no condensed water flows out to obtain concentrated solution, repeatedly extracting the concentrated solution with ethanol for 4 times, adding ethanol under stirring at 400rpm each time, stirring at 50deg.C for 2 hr after the addition, filtering after stirring, filtering to obtain ethanol extract, and cooling to 10deg.C; the total addition amount of ethanol is 2 times of the volume of the concentrated solution.
5. The method for extracting coenzyme Q10 according to claim 1, wherein: and c, the volume ratio of petroleum ether to the mixed solution in the step is 2:1, stirring is continuously carried out in the adding process, stirring is carried out at a rotating speed of 500rpm until the mixture is clear, and then the mixture is kept stand for 2 hours.
6. The method for extracting coenzyme Q10 according to claim 1, wherein: the organic phase in the step d is concentrated under the conditions of 50 ℃ and 0.095Mpa vacuum degree.
7. The method for extracting coenzyme Q10 according to claim 1, wherein: and e, dissolving the extract in the step at 55 ℃, adding 0.3% active carbon after dissolving and clarifying, stirring for 30min at 55 ℃ and 600rpm, carrying out suction filtration to obtain a decolorized solution, cooling the decolorized solution to 22.5 ℃ at 4 ℃/h, and carrying out suction filtration.
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