CN105087738A - Method for preparing natural astaxanthin through microemulsion phase biotransformation - Google Patents
Method for preparing natural astaxanthin through microemulsion phase biotransformation Download PDFInfo
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- CN105087738A CN105087738A CN201510578753.5A CN201510578753A CN105087738A CN 105087738 A CN105087738 A CN 105087738A CN 201510578753 A CN201510578753 A CN 201510578753A CN 105087738 A CN105087738 A CN 105087738A
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- astaxanthin
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Abstract
The invention provides a method for preparing natural astaxanthin through microemulsion phase biotransformation. The natural astaxanthin is prepared from astaxanthin ester, and the method comprises the following steps: preparing an organic phase containing a substrate and an enzyme-containing microemulsion, so that the oil-soluble substrate and water-soluble enzyme are uniformly dispersed in a reaction system; fully contacting, and enzymatically hydrolyzing under a certain condition so that the astaxanthin ester is enzymatically hydrolyzed into astaxanthin and fatty acid; and after enzymolysis, separating a reaction product so as to obtain natural astaxanthin. According to the method for preparing the natural astaxanthin disclosed by the invention, enzymolysis transformation rate reaches more than 60%; and the method is mild in reaction condition, low in energy consumption, environment-friendly and relatively good in application prospect.
Description
Technical field
The invention belongs to active substance preparing technical field, be specifically related to a kind of method utilizing microemulsion phase bio-transformation to prepare natural astaxanthin.
Background technology
Astaxanthin (Astaxanthin) has another name called astaxanthin, Astaxanthin, and chemical name is 3,3 '-dihydroxyl-β, β-carotene-4,4 '-diketone, and molecular formula is C
40h
52o
4, relative molecular mass is 596.86, is extensively present in marine animal and plant body, as shrimp, crab, wild salmon, rainbow trout, micro-algae etc., is a kind of natural carotenoid.Its chemical structure is connected with conjugated double bond form by four isoprene units, the six-membered ring structure be made up of Liang Ge isoprene unit at two ends.The chemical structure of astaxanthin uniqueness, makes it have the functions such as excellent anti-oxidant, anticancer and enhancing body is immune.
At occurring in nature, astaxanthin mainly exists with the form of astaxanthin ester, and the acquisition of natural astaxanthin is mainly obtained by being hydrolyzed to astaxanthin ester.Traditional method for hydrolysis has saponification method, namely utilize highly basic the hydrolysis of the fatty acid chain of astaxanthin ester to be fallen, but this technique alkali charge is large, easily cause environmental pollution, meanwhile, the astaxanthin that saponification obtains very easily is oxidized to astacin and/or half astacin under alkaline environment, produces by product.In addition, although utilize the method for lipase enzymolysis to prepare astaxanthin have certain suitability, traditional reaction system causes enzymolysis low conversion rate, and requires higher to the specificity of enzyme, is difficult to realize industrial applications.
Summary of the invention
The object of this invention is to provide a kind of method utilizing microemulsion phase bio-transformation to prepare natural astaxanthin, namely be raw material with astaxanthin ester, by preparation containing the organic phase of substrate with containing enzyme microemulsion, the then method of enzyme-squash techniqued natural astaxanthin, thus make up the deficiencies in the prior art.
Method of the present invention, includes following step:
1) preparation is containing the organic phase of substrate
Be raw material with astaxanthin ester, add the carrier oil that mass ratio is 1:1 ~ 20, fully mix, astaxanthin ester is dissolved in the middle of carrier oil uniformly as oil phase; Then in oil phase, add emulsifying agent and/or the assistant for emulsifying agent mixture of 1 ~ 10 times of volume, homogeneous makes system be uniformly dispersed, and obtains the organic phase containing substrate;
Wherein used carrier oil is one or more in straight-chain fatty acid ester, glycerin fatty acid ester;
Emulsifying agent used is the mixture of one or more in sorbitol fatty acid ester emulsifying agent, phosphatide emulsifier, sugared lipid emulsifiers;
Assistant for emulsifying agent is the mixture of one or more in ethanol, butanols, propylene glycol, polyoxyethylene glycol, glycerine and polyglycerol ester;
2) preparation is containing enzyme microemulsion
Lipase is dissolved in damping fluid, obtains enzyme liquid; To step 1) obtain containing adding enzyme liquid in substrate organic phase, homogeneous obtains containing enzyme microemulsion;
3) enzymolysis
By step 2) prepare carry out enzyme digestion reaction containing enzyme microemulsion, enzymatic hydrolysis condition is 30 DEG C ~ 70 DEG C, pH5.0 ~ 8.0, and enzymolysis time is 1h ~ 20h;
4) product separation
After enzymolysis completes, in enzymolysis product, add carrier oil make hydrolysis obtain oil-soluble free astaxanthin to separate from emulsification system, collect oil phase, through concentrating under reduced pressure, obtain natural astaxanthin product.
Described lipase is the mixture of one or more in candiyeast esterase, aspergillus esterase, pseudomonas esterase and head mold esterase.
The present invention utilizes microemulsion phase bio-transformation to prepare the method for astaxanthin, process is passed through to carry out Testing and appraisal into thin-layer chromatography (TLC), LC-MS to converted product, and result shows the method that the invention provides the natural free astaxanthin of a kind of preparation newly.Adopt method of the present invention, the astaxanthin monomer rate of recovery reaches as high as more than 80%.Present method is simple to operate, and reaction conditions is gentle, and energy consumption is low, environmental friendliness, has good application prospect.
Embodiment
Below adopt embodiment to describe embodiments of the present invention in detail, to the present invention, how utilisation technology means solve technical problem whereby, and the implementation procedure reaching technique effect can fully understand and implement according to this.
Astaxanthin detection method:
HPLC analyzes
Accurately take 2.0mg sample, add 10ml chromatographic pure dichloromethane and dissolve, through 0.22 μm of organic membrane filter, then carry out HPLC-MS analysis.Detecting instrument: 1100 series of high efficiency liquid chromatographs, joins diode-array detector (DAD, Agilent company of the U.S.); Chromatographic column is DevelosilC30-UG (4.6mm × 250mm, 5 μm); Mobile phase A: methyl alcohol; Mobile phase B: methyl tertiary butyl ether; Linear gradient elution: 0-15min:B is 0%; 15-22min:B rises to 22% by 0%; 22-48min:B maintains 22%; 48-56min:B rises to 40% by 22%; 56-76min:B is 40%.Flow velocity is 1.0ml/min; Determined wavelength: 476nm; Column temperature: 35 DEG C; DAD full wavelength scanner scope: 200 ~ 800nm; Sample size is 10 μ L.By integral area, with astaxanthin standard solution drawing standard curve, astaxanthin is carried out quantitatively, and then calculate the rate of recovery of astaxanthin monomer.
Embodiment 1
(1) preparation is containing substrate organic phase
With antarctic krill astaxanthin ester for raw material, add the ethyl acetate that mass ratio is 1:2, fully mix, astaxanthin ester is dissolved in the middle of carrier oil, uniformly as oil phase.Then in oil phase, add emulsifying agent and assistant for emulsifying agent mixture, the then homogeneous of 2 times of volumes, system is uniformly dispersed, obtain the organic phase containing substrate.Emulsifying agent used is: tween 80; Assistant for emulsifying agent is: ethanol; Wherein the volume ratio of emulsifying agent and assistant for emulsifying agent is: 1:0.5.
(2) preparation is containing enzyme microemulsion
Lipase is dissolved in the phosphate buffered saline buffer of pH7, obtains enzyme liquid; What obtain to step (1) contains in substrate organic phase the enzyme liquid adding 5 times, homogeneous, obtains containing enzyme microemulsion.
(3) enzymolysis
That step (2) is prepared carries out enzyme digestion reaction containing enzyme microemulsion under certain condition, and reaction conditions is: enzymatic hydrolysis condition is 40 DEG C, pH5.5, and enzymolysis time is 12h.
(4) product separation
After enzymolysis completes, in system, add ethyl acetate, until breakdown of emulsion, make hydrolysis obtain oil-soluble free astaxanthin to separate from emulsification system, collect oil phase, through concentrating under reduced pressure, obtain natural astaxanthin product, detect through HPLC, the rate of recovery of free astaxanthin monomer is 70.8%.
Embodiment 2
(1) preparation is containing substrate organic phase
With Haematocoocus Pluvialls source astaxanthin ester for raw material, add the ethyl butyrate that mass ratio is 1:4, fully mix, astaxanthin ester is dissolved in the middle of carrier oil, uniformly as oil phase.Then in oil phase, add emulsifying agent and assistant for emulsifying agent mixture, the then homogeneous of 3 times of volumes, system is uniformly dispersed, obtain the organic phase containing substrate.Emulsifying agent used is: polysorbate60; Assistant for emulsifying agent is: poly(oxyethylene glycol) 400; Wherein the volume ratio of emulsifying agent and assistant for emulsifying agent is: 1:0.5.
(2) preparation is containing enzyme microemulsion
Lipase is dissolved in pH7.5 phosphate buffered saline buffer, obtains enzyme liquid; What obtain to step (1) contains in substrate organic phase the enzyme liquid adding 8 times, homogeneous, obtains containing enzyme microemulsion.
(3) enzymolysis
That step (2) is prepared carries out enzyme digestion reaction containing enzyme microemulsion under certain condition, and reaction conditions is: enzymatic hydrolysis condition is 40 DEG C, pH60, and enzymolysis time is 10h.
(4) product separation
After enzymolysis completes, in system, add carrier oil, until breakdown of emulsion, make hydrolysis obtain oil-soluble free astaxanthin to separate from emulsification system, collect oil phase, through concentrating under reduced pressure, obtain natural astaxanthin product, detect through HPLC, the rate of recovery of free astaxanthin monomer is 82.3%.
Embodiment 3
(1) preparation is containing substrate organic phase
With antarctic krill astaxanthin ester for raw material, add the tributyrin that mass ratio is 1:3, fully mix, astaxanthin ester is dissolved in the middle of carrier oil, uniformly as oil phase.Then in oil phase, add emulsifying agent and assistant for emulsifying agent mixture, the then homogeneous of 4 times of volumes, system is uniformly dispersed, obtain the organic phase containing substrate.Emulsifying agent used is: fatty acid mono glycidol; Assistant for emulsifying agent is: propylene glycol; Wherein the volume ratio of emulsifying agent and assistant for emulsifying agent is: 1:0.8.
(2) preparation is containing enzyme microemulsion
Lipase is dissolved in pH7 phosphate buffered saline buffer, obtains enzyme liquid; What obtain to step (1) contains in substrate organic phase the enzyme liquid adding 10 times, homogeneous, obtains containing enzyme microemulsion.
(3) enzymolysis
That step (2) is prepared carries out enzyme digestion reaction containing enzyme microemulsion under certain condition, and reaction conditions is: enzymatic hydrolysis condition is 45 DEG C, pH6.5, and enzymolysis time is 18h.
(4) product separation
After enzymolysis completes, in system, add carrier oil, until breakdown of emulsion, make hydrolysis obtain oil-soluble free astaxanthin to separate from emulsification system, collect oil phase, through concentrating under reduced pressure, obtain natural astaxanthin product, detect through HPLC, the rate of recovery of free astaxanthin monomer is 78.5%.
Embodiment 4
(1) preparation is containing substrate organic phase
With Haematocoocus Pluvialls source astaxanthin ester for raw material, add the triolein that mass ratio is 1:8, fully mix, astaxanthin ester is dissolved in the middle of carrier oil, uniformly as oil phase.Then in oil phase, add emulsifying agent and assistant for emulsifying agent mixture, the then homogeneous of 5 times of volumes, system is uniformly dispersed, obtain the organic phase containing substrate.Emulsifying agent used is: lauric monoglyceride; Assistant for emulsifying agent is: propyl carbinol; Wherein the volume ratio of emulsifying agent and assistant for emulsifying agent is: 1:0.6.
(2) preparation is containing enzyme microemulsion
Lipase is dissolved in pH7 phosphate buffered saline buffer, obtains enzyme liquid; What obtain to step (1) contains in substrate organic phase the enzyme liquid adding 12 times, homogeneous, obtains containing enzyme microemulsion.
(3) enzymolysis
That step (2) is prepared carries out enzyme digestion reaction containing enzyme microemulsion under certain condition, and reaction conditions is: enzymatic hydrolysis condition is 60 DEG C, pH7.0, and enzymolysis time is 15h.
(4) product separation
After enzymolysis completes, in system, add carrier oil, until breakdown of emulsion, make hydrolysis obtain oil-soluble free astaxanthin to separate from emulsification system, collect oil phase, through concentrating under reduced pressure, obtain natural astaxanthin product, detect through HPLC, the rate of recovery of free astaxanthin monomer is 80.6%.
Embodiment 5
(1) preparation is containing substrate organic phase
With prawn source astaxanthin ester for raw material, add the Semen Maydis oil that mass ratio is 1:6, fully mix, astaxanthin ester is dissolved in the middle of carrier oil, uniformly as oil phase.Then in oil phase, add emulsifying agent and assistant for emulsifying agent mixture, the then homogeneous of 2.5 times of volumes, system is uniformly dispersed, obtain the organic phase containing substrate.Emulsifying agent used is: propylene glycol fatty acid ester; Assistant for emulsifying agent is: ethanol; Wherein the volume ratio of emulsifying agent and assistant for emulsifying agent is: 1:0.4.
(2) preparation is containing enzyme microemulsion
Lipase is dissolved in pH7.5 phosphate buffered saline buffer, obtains enzyme liquid; What obtain to step (1) contains in substrate organic phase the enzyme liquid adding 3 times, homogeneous, obtains containing enzyme microemulsion.
(3) enzymolysis
That step (2) is prepared carries out enzyme digestion reaction containing enzyme microemulsion under certain condition, and reaction conditions is: enzymatic hydrolysis condition is 65 DEG C, pH7.5, and enzymolysis time is 6h.
(4) product separation
After enzymolysis completes, in system, add carrier oil, until breakdown of emulsion, make hydrolysis obtain oil-soluble free astaxanthin to separate from emulsification system, collect oil phase, through concentrating under reduced pressure, obtain natural astaxanthin product, detect through HPLC, the rate of recovery of free astaxanthin monomer is 76.4%.
Comparative example:
With Haematocoocus Pluvialls source astaxanthin ester for raw material, being distributed in ethanol/water system, through fully stirring, system being uniformly dispersed, then the lipase enzyme amount identical with embodiment 2 is added, carry out enzymolysis at identical conditions, enzymolysis terminates rear separated product, analyzes the content of wherein astaxanthin.
Comparative test result:
| Experimental group | The rate of recovery (%) of free astaxanthin |
| Embodiment 2 | 83.2 |
| Comparative example | 34.6 |
Comparing result shows, by utilizing microemulsion phase of the present invention to carry out bio-transformation to astaxanthin ester, can significantly improve the rate of recovery of free astaxanthin.
The above is only preferred embodiment of the present invention, and be not restriction the present invention being made to other form, any those skilled in the art may utilize the technology contents of above-mentioned announcement to be changed or be modified as the Equivalent embodiments of equivalent variations.But everyly do not depart from technical solution of the present invention content, any simple modification, equivalent variations and the remodeling done above embodiment according to technical spirit of the present invention, still belong to the protection domain of technical solution of the present invention.
Claims (6)
1. utilize microemulsion phase bio-transformation to prepare a method for natural astaxanthin, it is characterized in that, described method includes following step:
1) preparation is containing the organic phase of substrate
Be raw material with astaxanthin ester, add the carrier oil that mass ratio is 1:1 ~ 20, fully mix, astaxanthin ester is dissolved in the middle of carrier oil uniformly as oil phase; Then in oil phase, add emulsifying agent and/or the assistant for emulsifying agent mixture of 1 ~ 10 times of volume, homogeneous makes system be uniformly dispersed, and obtains the organic phase containing substrate;
2) preparation is containing enzyme microemulsion
Lipase is dissolved in damping fluid, obtains enzyme liquid; To step 1) obtain containing adding enzyme liquid in substrate organic phase, homogeneous obtains containing enzyme microemulsion;
3) enzymolysis
By step 2) prepare carry out enzyme digestion reaction containing enzyme microemulsion, enzymatic hydrolysis condition is 30 DEG C ~ 70 DEG C, pH5.0 ~ 8.0, and enzymolysis time is 1h ~ 20h;
4) product separation
After enzymolysis completes, in enzymolysis product, add carrier oil make hydrolysis obtain oil-soluble free astaxanthin to separate from emulsification system, collect oil phase, through concentrating under reduced pressure, obtain natural astaxanthin product.
2. the method for claim 1, is characterized in that, described carrier oil is one or more in straight-chain fatty acid ester and glycerin fatty acid ester.
3. the method for claim 1, is characterized in that, described emulsifying agent and the volume ratio of assistant for emulsifying agent are 1:1.
4. the method as described in claim 1 or 3, is characterized in that, described emulsifying agent is one or more in sorbitol fatty acid ester emulsifying agent, phosphatide emulsifier, sugared lipid emulsifiers.
5. the method as described in claim 1 or 3, is characterized in that, described assistant for emulsifying agent is one or more in ethanol, butanols, propylene glycol, polyoxyethylene glycol, glycerine and polyglycerol ester.
6. the method for claim 1, is characterized in that, described lipase is one or more in candiyeast esterase, aspergillus esterase, pseudomonas esterase and head mold esterase.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106834554A (en) * | 2017-03-01 | 2017-06-13 | 四川金象赛瑞化工股份有限公司 | A kind of method that hemicellulose continuous hydrolysis prepare xylose |
| CN108179053A (en) * | 2018-01-26 | 2018-06-19 | 日照职业技术学院 | A kind of preparation method of high quality Antarctic krill oil |
| CN110179684A (en) * | 2019-07-01 | 2019-08-30 | 日照职业技术学院 | It is a kind of can efficient absorption natural astaxanthin eye cream and preparation method thereof |
| CN112941049A (en) * | 2021-02-24 | 2021-06-11 | 中国海洋大学 | Lipase and application thereof in hydrolyzing astaxanthin ester |
| CN113185438A (en) * | 2021-04-28 | 2021-07-30 | 云南爱尔康生物技术有限公司 | Preparation method of high-purity astaxanthin ester from haematococcus pluvialis |
| CN115299606A (en) * | 2022-09-14 | 2022-11-08 | 云南龙布瑞生物科技有限公司 | Method for separating and purifying endogenous pigment from fresh microalgae cells |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101892281A (en) * | 2010-07-28 | 2010-11-24 | 中国农业大学 | Method for preparing astaxanthin monomer |
| CN104877944A (en) * | 2015-06-14 | 2015-09-02 | 中国海洋大学 | Astaxanthin esterase production strain and application of strain in preparation of free astaxanthin |
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2015
- 2015-09-12 CN CN201510578753.5A patent/CN105087738A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101892281A (en) * | 2010-07-28 | 2010-11-24 | 中国农业大学 | Method for preparing astaxanthin monomer |
| CN104877944A (en) * | 2015-06-14 | 2015-09-02 | 中国海洋大学 | Astaxanthin esterase production strain and application of strain in preparation of free astaxanthin |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106834554A (en) * | 2017-03-01 | 2017-06-13 | 四川金象赛瑞化工股份有限公司 | A kind of method that hemicellulose continuous hydrolysis prepare xylose |
| CN108179053A (en) * | 2018-01-26 | 2018-06-19 | 日照职业技术学院 | A kind of preparation method of high quality Antarctic krill oil |
| CN108179053B (en) * | 2018-01-26 | 2021-07-20 | 日照职业技术学院 | Preparation method of high-quality euphausia superba oil |
| CN110179684A (en) * | 2019-07-01 | 2019-08-30 | 日照职业技术学院 | It is a kind of can efficient absorption natural astaxanthin eye cream and preparation method thereof |
| CN112941049A (en) * | 2021-02-24 | 2021-06-11 | 中国海洋大学 | Lipase and application thereof in hydrolyzing astaxanthin ester |
| CN112941049B (en) * | 2021-02-24 | 2022-07-08 | 中国海洋大学 | Lipase and application thereof in hydrolyzing astaxanthin ester |
| CN113185438A (en) * | 2021-04-28 | 2021-07-30 | 云南爱尔康生物技术有限公司 | Preparation method of high-purity astaxanthin ester from haematococcus pluvialis |
| CN115299606A (en) * | 2022-09-14 | 2022-11-08 | 云南龙布瑞生物科技有限公司 | Method for separating and purifying endogenous pigment from fresh microalgae cells |
| CN115299606B (en) * | 2022-09-14 | 2024-02-02 | 云南龙布瑞生物科技有限公司 | Method for separating and purifying endogenous pigment from fresh microalgae cells |
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