CN1762365A - Beta-carotene clathrate and its preparation method - Google Patents
Beta-carotene clathrate and its preparation method Download PDFInfo
- Publication number
- CN1762365A CN1762365A CN 200510012829 CN200510012829A CN1762365A CN 1762365 A CN1762365 A CN 1762365A CN 200510012829 CN200510012829 CN 200510012829 CN 200510012829 A CN200510012829 A CN 200510012829A CN 1762365 A CN1762365 A CN 1762365A
- Authority
- CN
- China
- Prior art keywords
- beta
- carotene
- clathrate
- hours
- water
- 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.)
- Granted
Links
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention provides a beta-carotene inclusion compound, which comprises beta-carotene and beta-cyclodextrin derivative by the weight ratio of 1:9-50. The preparing process comprises the steps of mixing beta-cyclodextrin derivative with beta-carotene, grinding 1-3 hours, dissolving with right amount of alcohol, agitating, evaporating the dissolvent and dissolving the solid inclusion compound into water, stewing 12-24 hours at a low temperature, decompression concentration, vacuum drying 3-6 hours at 35-50 deg C.
Description
Technical field
The present invention relates to beta-carotene clathrate, specifically clathrate of forming by beta-carotene and beta-cyclodextrin derivative and preparation method thereof.
Background technology
Beta-carotene is a conjugated double bond compound, molecular formula C
40H
56, molecular weight is 536.88.Beta-carotene is aubergine crystallization or crystalline powder, odorless, tasteless, and oxidation easily takes place in chance air, light, dissolves in Carbon bisulfide, benzene, chloroform, hexane and vegetable oil, and is water insoluble.
Beta-carotene plays very important physiological function in vivo.1. beta-carotene is the precursor of vitamin A, and the normal physiological function of keeping human body skin and eyes is had important effect.2. can stimulate immunity of organism, raise immunity.3. be fabulous antioxidant, can remove free radical, reduce the photosensitized oxidation effect, can prevent to form tumor and atherosclerosis.4. can be used for treating early senile dementia, also can be used for the leper.5. connect alternative ability between can strengthening cell and cell stitching.Thereby suppress or reduce the generation of cancer.Beta-carotene not only has great application in the health care medicine of disease preventing and treating, also be widely used in grocery trade, daily cosmetics industry, feed additive.
Cyclodextrin forms clathrate with molecular structure and the many guest molecules of its special " interior hydrophobic, outer hydrophilic ".Cyclodextrin can improve the dissolubility of medicine in water as pharmaceutical carrier, increases medicine stability, improves bioavailability.Application aspect cosmetics can keep its active component, is used for the improvement of technology and quality.In the derivant of beta-schardinger dextrin-, the HP-dissolubility is big, and hemolytic activity is low, and zest is little, and toxic and side effects is low, and is safe.Sulfobutyl ether-beta-schardinger dextrin-is the novel ionizable cyclodextrin derivative of new listing, oral administration safety is similar to HP-, does not have obvious cytotoxicity, and renal function is not had influence, and have higher water solublity, at field of medicaments wide application prospect is arranged.
Because beta-carotene is water insoluble, and contains many unsaturated double-bonds in the structure, poor stability influences its application performance.The most frequently used solution is microcapsule technology and cyclodextrin inclusion technique at present, but the efficient of microencapsulation process and productive rate are all not ideal.Cyclodextrin inclusion technique is commonly used saturated water solution method and polishing.Saturated water solution method though stir through long-time, still floats the medicine that many not enclose are arranged in solution surface, so the actual content of beta-carotene is very low in the clathrate in preparation process.The then dissolubility of the beta-carotene clathrate of polishing preparation is relatively poor.
Summary of the invention
The purpose of this invention is to provide a kind of stability, water solublity beta-carotene clathrate preferably, and preparation method should be simple and easy to do, inclusion rate is high, prepared clathrate purity height, dissolubility is good.
Beta-carotene clathrate provided by the present invention is made up of beta-carotene and beta-cyclodextrin derivative, and the weight ratio of beta-carotene and beta-cyclodextrin derivative is 1: 9～50.
Described beta-cyclodextrin derivative is HP-and sulfobutyl ether-beta-schardinger dextrin-.
The preparation method of beta-carotene clathrate of the present invention the steps include: that (1) is that beta-cyclodextrin derivative is mixed with beta-carotene, under nitrogen protection, adds low amounts of water and makes the mixture moistening, grinds 1～3 hour, gets red paste; (2) add an amount of ethanol or water in the paste and make it to dissolve with alcoholic acid mixture, stirring at low speed is 2～12 hours under the room temperature, and the evaporated under reduced pressure organic solvent also is dissolved in the distilled water stand at low temperature 5～24 hours again with solid clathrates; (3) concentrating under reduced pressure, 35 ℃～50 ℃ vacuum dryings 3～6 hours, solid clathrates.Also concentrate lyophilization or spray drying can be got solid clathrates.
Described preparation method step (2) also can be, adds suitable quantity of water in the paste and makes it dissolving, and stirring at low speed is 2～12 hours under the room temperature, stand at low temperature 5～24 hours.
Compared with prior art, beneficial effect of the present invention is:
(1) heat stability of clathrate is investigated: with beta-carotene, HP-beta-CD inclusion, SBE-beta-CD inclusion respectively 80 ℃ of heating in water bath two hours, the absorbance residual rate is respectively after 30%, 71% and 73%. constant temperature accelerated tests results have proved that beta-carotene is by enclose, and its stability significantly improves.
(2) the anti-photodissociation investigation of clathrate: 20W UV illumination 12 hours, the content of beta-carotene reduces, and peak shape changes, and illustrates that the molecular structure of beta-carotene has suffered destruction.Though the content after the clathrate illumination decreases, beta-carotene does not have degeneration.
(3) the clathrate non-oxidizability is investigated: oxidant is very big to the influence of beta-carotene, and solution colour shoals after the oxidation, and the beta-carotene loss surpasses 80% after two hours, and cyclodextrin derivative can at utmost protect beta-carotene not to be subjected to hydrogen peroxide oxidation.After two hours in the clathrate beta-carotene loss seldom, the loss of HP-beta-CD inclusion and SBE-beta-CD inclusion is 15%.
(4) solubility test of clathrate: beta-carotene is 1.02 * 10
-4G/ml (literature value), HP-beta-CD inclusion are 2.5 * 10
-3G/ml, SBE-beta-CD inclusion are 3.57 * 10
-3G/ml, wherein HP-β-CD, SBE-β-CD distinguishes 25 times and 35 times of solubilisings.
In a word, beta-carotene clathrate of the present invention dissolubility in water significantly improves, and preparation is simple, and the inclusion rate height is convenient to industrialization.
Description of drawings
The uv-visible absorption spectra figure of Fig. 1 beta-carotene hydroxypropyl-beta-cyclodextrin inclusion.Among the figure: 1, the DMF solution of beta-carotene; 2, clathrate DMF solution; 3, clathrate aqueous solution; 4, HP-β-CD aqueous solution.
Fig. 2 hydroxypropyl-beta-cyclodextrin inclusion and beta-carotene, HP-and the two mechanical impurity infrared spectrogram relatively.Among the figure: 1, beta-carotene; 2, HP-β-CD; 3, beta-carotene-HP-beta-CD inclusion; 4, the beta-carotene-HP-β-CD of polishing preparation; 5,1:1 beta-carotene-HP-β-CD player tool mixture.
The specific embodiment
Embodiment 1: the present invention prepares beta-carotene and HP-β-CD solid clathrates
Accurately take by weighing beta-carotene 0.02g, HP-β-CD1g places mortar jointly, drips the 1ml distilled water, under protection of nitrogen gas, grind.Grind after 3 hours, get red paste, with the red paste of 100ml dissolve with ethanol, stirring at low speed is 6 hours under the room temperature, and organic solvent is removed in distilling under reduced pressure, adds distilled water and dissolves stand at low temperature 5 hours again.Behind the concentrating under reduced pressure, 50 ℃ of vacuum dryings 5 hours, the dark red solid clathrate.Adopt ultraviolet visible spectrophotometry to measure the content (w/w)=1.7% of beta-carotene in the clathrate, yield=82%, inclusion rate=95%.
Adopt ultraviolet visible spectrophotometry, institute's enclose material is a beta-carotene in the mensuration clathrate.With the very strong organic solvent DMF of dissolubility extraction clathrate, analyze its absorption spectrum, characteristic absorption peak and beta-carotene are dissolved in full accord among the DMF, and what show institute's enclose in the clathrate is the beta-carotene (see figure 1).
Embodiment 2: the present invention prepares beta-carotene and HP-β-CD solid clathrates
Accurately take by weighing beta-carotene 0.05g, HP-β-CD0.45g places mortar jointly, drips the 1ml distilled water, under protection of nitrogen gas, grind.Grind after 2 hours, get red paste, with the red paste of 50ml dissolve with ethanol, stirring at low speed is 6 hours under the room temperature, and organic solvent is removed in distilling under reduced pressure, adds distilled water and dissolves stand at low temperature 5 hours again.Behind the concentrating under reduced pressure, 50 ℃ of vacuum dryings 5 hours, the dark red solid clathrate.Adopt ultraviolet visible spectrophotometry to measure the content (w/w)=6.21% of beta-carotene in the clathrate, yield=82%, inclusion rate=97%.
Adopt infrared spectrometry, institute's enclose material is a beta-carotene in the mensuration clathrate.The whole feature that shows the infrared spectrum of HP-of the infrared spectrum of clathrate, but the characteristic absorption peak 966cm of beta-carotene
-1(C-H out-of-plane vibration), 1628cm
-1(C=C stretching vibration) disappears, and shows that beta-carotene and cyclodextrin have formed the clathrate (see figure 2).
Embodiment 3: the present invention prepares beta-carotene and SBE-β-CD solid clathrates
Accurately take by weighing beta-carotene 0.02g, SBE-β-CD0.4g places mortar jointly, drips the 1ml distilled water, under protection of nitrogen gas, grind.Grind after 3 hours, get red paste, dissolve red paste with suitable quantity of water, stirring at low speed is 6 hours under the room temperature, stand at low temperature 5 hours.Behind the concentrating under reduced pressure, 35 ℃ of vacuum dryings 5 hours, the dark red solid clathrate.Adopt ultraviolet visible spectrophotometry to measure the content (w/w)=6.4% of beta-carotene in the clathrate, yield=73%, inclusion rate=98.56%.
Claims (4)
1, a kind of beta-carotene clathrate is characterized in that: be made up of beta-carotene and beta-cyclodextrin derivative, the weight ratio of beta-carotene and beta-cyclodextrin derivative is 1: 9～50.
2, a kind of beta-carotene clathrate according to claim 1 is characterized in that: beta-cyclodextrin derivative is HP-and sulfobutyl ether-beta-schardinger dextrin-.
3, the preparation method of a kind of beta-carotene clathrate according to claim 1, it is characterized in that step is: (1) is that beta-cyclodextrin derivative is mixed with beta-carotene, under nitrogen protection, adds low amounts of water and makes the mixture moistening, ground 1～3 hour, and got red paste; (2) add an amount of ethanol or water in the paste and make it to dissolve with alcoholic acid mixture, stirring at low speed is 2～12 hours under the room temperature, and the evaporated under reduced pressure organic solvent also is dissolved in the distilled water stand at low temperature 5～24 hours again with solid clathrates; (3) concentrating under reduced pressure, 35 ℃～50 ℃ vacuum dryings 3～6 hours, solid clathrates.
4, the preparation method of a kind of beta-carotene clathrate according to claim 3 is characterized in that described step (2), adds suitable quantity of water in the paste and makes it dissolving, and stirring at low speed is 2～12 hours under the room temperature, stand at low temperature 5～24 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100128294A CN1316973C (en) | 2005-09-16 | 2005-09-16 | Beta-carotene clathrate and its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100128294A CN1316973C (en) | 2005-09-16 | 2005-09-16 | Beta-carotene clathrate and its preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1762365A true CN1762365A (en) | 2006-04-26 |
| CN1316973C CN1316973C (en) | 2007-05-23 |
Family
ID=36746823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100128294A Expired - Fee Related CN1316973C (en) | 2005-09-16 | 2005-09-16 | Beta-carotene clathrate and its preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1316973C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108085352A (en) * | 2018-01-24 | 2018-05-29 | 江南大学 | A kind of method of two enzymes method control cyclodextrin inclusion compound sustained release |
-
2005
- 2005-09-16 CN CNB2005100128294A patent/CN1316973C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108085352A (en) * | 2018-01-24 | 2018-05-29 | 江南大学 | A kind of method of two enzymes method control cyclodextrin inclusion compound sustained release |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1316973C (en) | 2007-05-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5087086B2 (en) | Drug composition containing inclusion body of cyclodextrin / paclitaxel and method for producing the same | |
| US20110318397A1 (en) | Method for preparing high purity ginsenoside rd using lactobacillus casei and cosmetic composition for anti-wrinkle comprising the high purity ginsenoside rd | |
| US11648208B2 (en) | Nano complex comprising a nano drug delivery matrix; and a ginseng extract or a ginsenoside isolated therefrom | |
| JP5103476B2 (en) | Drug composition containing inclusion body of cyclodextrin docetaxel and method for producing the same | |
| DE19713092A1 (en) | Complexes of gamma-cyclodextrin and retinol or retinol derivatives, as well as processes for their preparation and their use | |
| CN104031174B (en) | Chitosan derivative capable of being specifically absorbed by small intestine as well as preparation method and drug-carrying nanoparticle of derivative | |
| Song et al. | Gallic acid/2-hydroxypropyl-β-cyclodextrin inclusion complexes electrospun nanofibrous webs: Fast dissolution, improved aqueous solubility and antioxidant property of gallic acid | |
| CN101744288B (en) | Clear oral preparation with coenzyme Q10 and preparation method thereof | |
| CN107922452A (en) | A kind of 1,4 oligoglucoses aldehydic acid of oxidized form β and its preparation method and application | |
| EP2727586A1 (en) | Soyasapogenol composition | |
| KR20220084304A (en) | Composition containing ultrafine compound and preparation thereof | |
| CN111920771A (en) | Resveratrol nano-liposome and preparation method and application thereof | |
| CN108998014B (en) | Preparation method and application of graphene quantum dot-based tumor catalysis nanoreactor | |
| CN1316973C (en) | Beta-carotene clathrate and its preparation method | |
| CN111944165B (en) | Polyphenol tyrosinase inhibitor and extraction method and application thereof | |
| KR20100054386A (en) | Trisin inclusion complex, a preparation method thereof, and a cosmetic composition for anti-oxidant and anti-inflammatory comprising the same | |
| CN1861670A (en) | Composition of beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene and preparation process thereof | |
| EP3305303A1 (en) | Chitosan nanofibres containing bioactive compounds | |
| CN107897647B (en) | Green preparation method of water-soluble lutein | |
| KR20100054379A (en) | Rutin inclusion complex, a preparation method thereof, and a cosmetic composition for antiaging comprising the same | |
| CN114224837A (en) | Preparation method of antioxidant liposome | |
| CN113812629A (en) | Preparation method of starch-ellagic acid inclusion compound and application of starch-ellagic acid inclusion compound in antioxidant food | |
| CN110835315A (en) | Preparation method of lycium ruthenicum red pigment | |
| WO2022045371A1 (en) | Composition and manufacturing method for said composition, method for improving fat-soluble component absorbability, method for improving fat-soluble component extraction efficiency, and fat-soluble component | |
| CN115368334B (en) | Method for improving extraction efficiency of total flavonoids of bamboo leaves |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20070523 Termination date: 20091016 |