CN100390227C - Composition of beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene and preparation process thereof - Google Patents
Composition of beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene and preparation process thereof Download PDFInfo
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Abstract
The present invention relates to a composition of beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene. The composition contains lycopene oleoresin or high-purity lycopene, beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin, wherein the quality proportion between the lycopene and mixed cyclodextrin is from 1: 3 to 30, the quality proportion between the beta-cyclodextrin in the mixed cyclodextrin and the hydroxypropyl-beta-cyclodextrin is from 99: 1 to 1: 99, and the composition is in a form of a red solid inclusion compound. A preparation method for the composition comprises the following steps: the lycopene oleoresin is added to a suspension or solution of the mixed cyclodextrin and water to be mixed and stirred in the presence of nitrogen; cooling, filtration, washing and vacuum drying are carried out, or drying under reduced pressure is directly carried out after stirring and cooling to obtain an inclusion compound. The composition overcomes the problems of high proportion of cyclodextrin, no ways of actual use, and influence on successor use after organic cosolvents are added in the prior art and obtains an inclusion compound of the cyclodextrin and lycopene; the obtained inclusion compound has the advantages of stable content, long shelf life and portability.
Description
Technical field
The present invention relates to the inclusion compound of the multiple mixture of lycopene oleo-resinous and beta-cyclodextrin and derivative thereof, and the preparation method of this inclusion compound.
Background technology
Lyeopene is a kind of natural pigment that is present in the red vegetables and fruits, be a kind of hydro carbons carotenoid, molecular weight 536.85, contain 11 conjugation carbon-to-carbon double bonds and 2 unconjugated double bonds, studies show that in a large number Lyeopene is very competent to the removing of the quencher of singlet oxygen and free radical, can form by blocking nitrosamine formation, the inducing cell differentiation, increase immunizing power, suppress cell proliferation, reduce dna damage, play especially heart of preventing cancer and multiple disease, prostate gland, the effect of mammary gland and other important organ organ diseases, along with people's going deep into to Lyeopene research, find that superior antioxidant property and the hypotoxicity of Lyeopene causes it to have plurality kinds of health care or therapeutic action, have important use and be worth and extensive market prospects.Lyeopene is water-soluble hardly, the oral absorption difficulty, and bioavailability is low.These unfavorable factors have restricted the widespread use of Lyeopene, and existing now many researchs and technological invention are in order to address these problems.The technological method of development mainly contains at present: the powdered solid of lycopene oleo-resinous solution, lycopene microcapsuleization, solid material absorption Lyeopene, Lyeopene/cyclodextrin inclusion technique method etc.But, take in the practical application simple and easy to do technological method keep Lyeopene raw material and formulation products stable, improve technical problem such as Lyeopene bioavailability and still have much room for improvement.
Cyclodextrin inclusion technique is that present development and application is applied to one of important technology ten thousand methods of indissoluble active compound faster, insoluble compound can form the inclusion compound of multiple molecule proportioning with cyclodextrin, object forms inclusion compound among entering (inclusion in) host compound with molecularity in this system, therefore, cyclodextrin inclusion compound can improve the solvability of object and dissolution rate, enhancing guest molecule stability.Utilize cyclodextrin and Lyeopene to form inclusion compound, Lyeopene a part or whole part is by inclusion, make it not be subject to the influence of temperature, oxygenant, illumination and obtain enough stability, and the raising that Lyeopene solubleness obtains in various degree behind the inclusion will help improving the bioavailability that absorbs and improve formulation products.
King Luo Xin etc. can be self-assembled into the supramolecule of nanoscale in the aqueous solution with UV method research inference beta-cyclodextrin and Lyeopene.After adopting aqua-solution method or grinding the stirring of merging aqua-solution method, filtering solids, concentrate, precipitation, dryly obtain the yellow solid crystallization by filtrate, but prepared yellow crystal does not carry out structural characterization, do not make clear and definite in detail composition identification and analysis and content of lycopene and measure (the uv-visible absorption spectra research of Lyeopene and beta-cyclo dextrin included compound, spectroscopy and spectroscopic analysis, 2004,24 (2): 183-186).Graciette Matioli etc. studied α-, β-and inclusion (the Microencapsulation of lycopene with cyclodextrins of γ-Huan Hujing and Lyeopene, Ci ê nc.Tecnol.Aliment.Campinas 23 (supl): 102-105dez.2003), prepared 50: 1 cyclodextrin of molecular ratio: the Lyeopene inclusion compound.Find in three kinds of cyclodextrin, β under 50: 1 conditions of molecular ratio-and γ-two kind of cyclodextrin can form inclusion compound with Lyeopene, stability test proves, 200: 1 γ-Huan Hujing of mass ratio: the inclusion compound of Lyeopene preparation is best, and its inclusion compound is Lyeopene is dissolved in preparation in the aqueous solution that acetone adds cyclodextrin again and gets.(the preparation of Lyeopene Benexate Hydrochloride such as Sun Xinhu, Food Additives Used in China, 2002 (5): 8-11) and (preparation of Lyeopene Benexate Hydrochloride such as Li Wei, food science and technology, 2002 (10): 39-41) studied the Lyeopene inclusion of beta-cyclodextrin, people's conclusion basically identicals such as its experimental technique, product composition and preparation method and Graciette Matioli, and particularly point out, lycopene oleo-resinous and beta-cyclodextrin are difficult to prepare inclusion compound.Beta-cyclodextrin in the inclusion compound of preparation gained: the molecular ratio of Lyeopene reaches more than 50: 1, and its mass ratio surpasses 105: 1, and the content of lycopene of inclusion compound is low excessively, and practical application is restricted.In addition, this inclusion compound and preparation method's defective also is, has used acetone, tetrahydrofuran (THF) etc. to be not useable for the organic solvent of food and medicinal use in the preparation process, is difficult to adopt usual way to be dispeled behind these organic solvent inclusions.
(U.S.Pat.No.5 such as Leuenberger, 221,735) with 10～10, the alpha-cylodextrin of 000 times of amount or hydroxypropyl-beta-cyclodextrin or methyl-beta-cyclodextrin mix with water, be mixed with the lycopene solution of 8～12% concentration with 1: 30～10: 1 organic solvent dissolution Lyeopenes, the mixture of cyclodextrin and water is joined, in the lycopene solution, through mixing under 60 ℃～90 ℃ conditions, cool off, filtering, get the inclusion complex in solution (16 times alpha-cylodextrin makes the Lyeopene solubilising to 2 μ g/ml) that filtrate prepares the Lyeopene cyclodextrin.What this method prepared is the inclusion compound of dissolved state, and its shortcoming is: the inclusion compound of solution state is difficult for preserving; Need in the preparation to use a large amount of cyclodextrin, and the price of these cyclodextrin is far above common and commonly used beta-cyclodextrin; Add organic solvents such as different carbon chain alcohols such as methyl alcohol～hexanol or chloroform in the preparation, these organism very easily form inclusion compound with cyclodextrin, cause the organic solvent high-content to residue in (inclusion compound of high residue organic solvent is not useable for food and medicinal use) in the inclusion complex in solution.These effects limit the practical application of Lyeopene cyclodextrin inclusion compound.
Although studying a high proportion of cyclodextrin (comprising beta-cyclodextrin, alpha-cylodextrin, hydroxypropyl-beta-cyclodextrin, methyl-beta-cyclodextrin etc.) at present shows with the Lyeopene exercising result, both are mixed in the water, and inclusion can take place, but organic solvent and the loaded down with trivial details preparation process of crossing a high proportion of cyclodextrin and adding hydrotropy make this technology be difficult to promote the market application.Therefore need development a kind of simple and practical Lyeopene inclusion compound technology of preparing and method.
Summary of the invention
When the objective of the invention is to overcome the cyclodextrin inclusion compound of prior art for preparing Lyeopene, cyclodextrin ratios is too high, can't the actual difficult point of using, and need in the preparation process to add the organic solvent of hydrotropy and the problem that influences follow-up use; Provide a kind of not with an organic solvent, and reduce the cyclodextrin inclusion compound of the Lyeopene of cyclodextrin ratios and the preparation method of this inclusion compound significantly.
The present invention adopts the different ratios beta-cyclodextrin to mix with hydroxypropyl-beta-cyclodextrin, and the hybrid ring dextrin less with mass fraction can prepare solid clathrates with lycopene oleo-resinous.The inclusion compound of gained can make Lyeopene solubleness increase by 50～110 times, and stability is significantly improved, and hybrid ring dextrin cost is starkly lower than and adopts single hydroxypropyl-beta-cyclodextrin; The more single beta-cyclodextrin of preparation method is easy.The solid clathrates granularity of preparation is fine and smooth evenly, colourity is good and have the favorable mechanical processing characteristics, can conveniently make various oral preparations.
Concrete scheme of the present invention is as follows:
Plant the inclusion compound of beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene, contain lycopene oleo-resinous or high purity Lyeopene, beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin in the inclusion compound, wherein the mass ratio of lycopene oleo-resinous or high purity Lyeopene and hybrid ring dextrin is 1: 3～30, the beta-cyclodextrin in the hybrid ring dextrin and the mass ratio of hydroxypropyl-beta-cyclodextrin are 99: 1～1: 99 (being hydroxypropyl-beta-cyclodextrin content 1%～99%), and its form is the red solid inclusion compound.
The ratio of beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin in the above scheme, the application recommend to adopt 4: 1 (being that hydroxypropyl-beta-cyclodextrin content is 20% hybrid ring dextrin).
Described lycopene oleo-resinous raw material is lycopene oleo-resinous commonly used.As: the lycopene oleo-resinous that contains Lyeopene 6%, 10%, 15% or 95%.
Because the lycopene concentration difference that adopts raw material to contain, the proportional range of Lyeopene is between 0.19%～23.7% in the described inclusion compound that obtains.
This inclusion compound is that beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin are obtained the hybrid ring dextrin according to the mixed of 99: 1～1: 99 scope, again hybrid ring dextrin and water are mixed with suspensoid or solution, the mass ratio of hybrid ring dextrin and water is 1: 1～5, the lycopene oleo-resinous that adds mass ratio 1/3～1/30 amount then, logical rare gas element mixes stirring down, cooling, filtration, washing, vacuum-drying, or the direct drying under reduced pressure in stirring cooling back obtains inclusion compound.Content of lycopene in its solid clathrates: 0.19%～23.75% (6% lycopene oleo-resinous of 1/30 amount obtains containing the solid clathrates of Lyeopene 0.19%, and 25% lycopene oleo-resinous of 1/3 amount obtains containing the solid clathrates of Lyeopene 6.25%).
Described rare gas element recommends to adopt nitrogen.
Above inclusion compound solid can be used as that raw material adds auxiliary material commonly used, vehicle is made tablet, capsule etc., when making various formulation, adds various auxiliary materials by the prior art of pharmacy or protective foods.
More particularly: described Lyeopene/mixing Preparation methods of cyclodextrin inclusion complexes, step is as follows:
Beta-cyclodextrin is mixed with the preferred proportion of hydroxypropyl-beta-cyclodextrin according to 4: 1, and it is standby that preparation becomes the hybrid ring dextrin;
1 part of hybrid ring dextrin is mixed with 1～5 times of amount pure water, the lycopene oleo-resinous (containing Lyeopene 6%～25%) that adds cyclodextrin mass ratio 1/3～1/30 amount, add the ethanol of lycopene oleo-resinous equivalent or do not add ethanol, mix, lead under 30 ℃～40 ℃ conditions of nitrogen insulation and stirred 1～24 hour, cooling, filter, get the solid washing, vacuum-drying promptly gets the dark red solid inclusion compound.
The hybrid ring dextrin is mixed with 1～3 times of amount pure water, the solid Lyeopene (content 70%～95%) that adds mass ratio 1/3～1/10 amount, mix, grind under the room temperature 1～12 hour when system is jelly, vacuum-drying promptly gets dark red solid inclusion compound (content of lycopene 6.3%～23.75%).
Above preparation method more optimize and more specifically step be:
The hybrid ring dextrin is mixed with 1～3 times of amount pure water, be incubated 30 ℃, add the lycopene oleo-resinous of mass ratio 1/5～1/6 amount, the leaching solids is cooled off, spends the night, crossed to logical nitrogen insulated and stirred 12 hours, and washing, vacuum-drying promptly get the red solid inclusion compound.
The hybrid ring dextrin is mixed with 1～2 times of amount pure water, make into suspensoid, the solid Lyeopene (content is more than 70%) that adds mass ratio 1/4～1/5 amount mixes, grinds under the room temperature 5 hours when obtaining even red jelly, and vacuum-drying promptly gets fluffy dark red solid inclusion compound.
Beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin are products commonly used on the market.Under the aqueous conditions, UV discovers (seeing accompanying drawing 1～2), Lyeopene can form inclusion compound fast with beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin, adopt the Hildebrand-Benesi method to measure the inclusion constant K a (seeing accompanying drawing 3～4) of lycopene/beta-cyclodextrin, Lyeopene/hydroxypropyl-beta-cyclodextrin, different concns lycopene oleo-resinous and beta-cyclodextrin form the inclusion constant such as the following table of inclusion compound
Lyeopene/cyclodextrin encapsulated constant K a (274nm)
Test shows, hydroxypropyl-beta-cyclodextrin has than bigger inclusion constant of beta-cyclodextrin and stronger inclusion performance; Lyeopene purity is high more, and inclusion constant K a is big more, and inclusion compound is stable more.Results suggest: use the cyclodextrin technology and can prepare stable inclusion compound, and hydroxypropyl-beta-cyclodextrin is than the easier inclusion compound for preparing of beta-cyclodextrin, inclusion compound is also more stable.Market 6% and 15% lycopene oleo-resinous commonly used has enough big inclusion constant (Ka=416～876M
-1).
Test is found, though lycopene oleo-resinous has solubleness preferably in alcohol organic solvent, but, because beta-cyclodextrin is insoluble to alcohol organic solvent (certain dissolving is only arranged) in methyl alcohol, therefore, add alcohol organic solvent in the inclusion of lycopene oleo-resinous and beta-cyclodextrin to preparation process influence and not obvious.Owing to deliquescent reason, do not add organic solvent and prepare the preparation process that lycopene oleo-resinous/Benexate Hydrochloride needs the long period.Hydroxypropyl-beta-cyclodextrin not only has good consistency and water-soluble with beta-cyclodextrin, and solubleness preferably arranged in alcohol organic solvent, alcohol organic solvent has good dissolution dispersity energy to lycopene oleo-resinous, therefore, be added with in hydroxypropyl-beta-cyclodextrin and the alcoholic acid inclusion system each thing and have mutually preferably that mutual solubility extremely helps accelerating inclusion speed.Evidence, add hydroxypropyl-beta-cyclodextrin and small amount of ethanol in lycopene oleo-resinous and the beta-cyclodextrin inclusion compound process simultaneously and can prepare required inclusion compound at short notice, also can comparatively fast obtain inclusion compound when not adding ethanol preparation, and inclusion compound solid granularity exquisiteness and colourity are evenly significantly better than Benexate Hydrochloride.Hydroxypropyl-beta-cyclodextrin solubility property good (dissolving each other) with water, the inclusion ability is strong, and Lyeopene is had stronger solublization, but its deficiency is the price height and has stronger water absorbability.Beta-cyclodextrin is cheap, and water absorbability is little, therefore, adopts the mixture of hydroxypropyl-beta-cyclodextrin and beta-cyclodextrin to prepare the deficiency that inclusion compound can overcome the single cyclodextrin of use, obtains good result.
Single cyclodextrin and hybrid ring dextrin are to the solublization of Lyeopene experiment: with 1 part of 15% lycopene oleo-resinous (Chinese Xinjiang) respectively with 5 parts of beta-cyclodextrins, or with 5 parts of hydroxypropyl-beta-cyclodextrins, or prepare serial inclusion compound respectively with 5 parts of hybrid ring dextrin, each inclusion compound is got 2 and is restrained that supersound process reaches balance in 100 ml waters, measure Lyeopene solubleness in the solution, get the hybrid ring dextrin and the solubleness relation of different ratios hydroxypropyl-beta-cyclodextrin, representative data is seen accompanying drawing 5 and following table:
Increase hydroxypropyl-beta-cyclodextrin content in the hybrid ring dextrin, the Lyeopene solubleness of inclusion compound obviously increases, though tomato red have highest solubility in the single hydroxypropyl-beta-cyclodextrin, the rising product cost of hydroxypropyl-beta-cyclodextrin content is fast rise (present hydroxypropyl-beta-cyclodextrin price is about 40 times of beta-cyclodextrin) also.Further analyze and find, the degree that the adding hydroxypropyl-beta-cyclodextrin increases Lyeopene solubleness (is solubilising degree Y, be Lyeopene poor solubility in solubleness and the beta-cyclodextrin in the hybrid ring dextrin) variant with the ascensional range of hybrid ring dextrin price, the relative beta-cyclodextrin price of hydroxypropyl-beta-cyclodextrin risen 40 times (X=40), its solubleness (Y) 8.29 μ g/ml that risen, its Y/X is cost performance, be the solubleness increasing amount that unit price rises and produces, cost performance and hydroxypropyl-beta-cyclodextrin relation with contents see the following form and accompanying drawing 6:
The result shows that the hybrid ring dextrin that contains hydroxypropyl-beta-cyclodextrin 20% has the highest cost performance, mixes can reach the solubilizing effect stronger than beta-cyclodextrin with a small amount of hydroxypropyl-beta-cyclodextrin.Two kinds of cyclodextrin synergistic results, the strong and cost of solublization increases few, and is significant to the control product cost, has good technical and economic benefit.
The Lyeopene solid clathrates of 3 parts of hybrid ring dextrin (1: 1) and 1 part of 6% lycopene oleo-resinous preparation, illumination and high temperature test comparing result such as following table (ultraviolet method mensuration content)
* resin caking coking
With 0 day content was 100.0%, and lycopene oleo-resinous is merely able to measure 5 days data, and the coking caking took place in the time of 10 days; 60 ℃ of humid test content of inclusion compound descend to some extent; Illumination and 40 ℃ of humid tests, the content of lycopene of solid clathrates changes less.Test of long duration, the solid clathrates room temperature lucifuge of Brown Glass Brown glass bottles and jars only packing was deposited 12 months, and content has decline (reaching 99.3%) slightly, and the lycopene oleo-resinous content that the same terms is deposited is 51.7%, and inclusion compound stability significantly is better than oleo-resinous.
It is too high that the present invention has overcome in the prior art cyclodextrin ratios, can't the actual difficult point of using, and need in the preparation process to add the organic solvent of hydrotropy and the problem that influences follow-up use; Provide not with an organic solvent, and reduced the cyclodextrin inclusion compound of the Lyeopene of cyclodextrin ratios significantly, and the preparation method of this inclusion compound.
Product of the present invention is a solid state Lyeopene inclusion inclusion compound, the solid clathrates granularity is fine and smooth evenly, colourity is good and have the favorable mechanical processing characteristics, have good consistency with other auxiliary materials (or vehicle), easy grinding and processing, easily preparation becomes various solid preparations.
Lyeopene component and stable content, cyclodextrin and Lyeopene form inclusion compound, and the Lyeopene composition of inclusion is constant, stable content significantly is better than Lyeopene raw materials such as oleo-resinous, and preservation, portable is grown, is easy to shelf life of products.
Lyeopene inclusion compound solvability and good dispersity, the preparation oral preparations helps improving bioavailability.
The solublization of hybrid ring dextrin significantly is better than beta-cyclodextrin, and price significantly is lower than hydroxypropyl-beta-cyclodextrin, helps reducing cost.
Preparation cycle is short, and the preparation of hybrid ring cyclodextrin inclusion compound is easier than single beta-cyclodextrin, operates simpler.
The inventive point of innovation and creation:
Form specific inclusion compound by beta-cyclodextrin/hydroxypropyl-beta-cyclodextrin/Lyeopene, its inclusion compound form is the inclusion compound of Lyeopene and hybrid ring dextrin.Such inclusion compound has the solubleness height, and the characteristics that stability is strong and cheap have high using value.
Lyeopene or lycopene oleo-resinous under water participation condition (available or without the organic solvent hydrotropy) stir or grind preparation with the hybrid ring dextrin become inclusion compound.Easy and simple to handle, processing condition are simple, the fugitive rate height of preparation cycle.
Inclusion compound stable in properties, light and the thermostability of preparation are strong, easily storage, easily processing.
The solid clathrates solvability is good, dispersion is fast, helps improving the Lyeopene bioavailability.
By the solid preparation stable content of inclusion compound preparation, outward appearance is good, portable, and the disintegration stripping is fast, good absorption, and product is easy to carry, preserves and uses.
The preparation of hybrid ring cyclodextrin inclusion compound and stability, solvability, outward appearance, economy etc. all are better than single Benexate Hydrochloride.
Description of drawings:
Fig. 1 is the 265～280nm uv-absorbing scintigram of Lyeopene under the different concns hydroxypropyl-beta-cyclodextrin of constant density in lycopene oleo-resinous (content 15%) aqueous solution.Along with hydroxypropyl-beta-cyclodextrin concentration rises, the Lyeopene uv-absorbing progressively increases (265～280nm cyclodextrin does not have uv-absorbing).
Fig. 2 is the 225～482nm uv-absorbing scintigram of Lyeopene under the different concns beta-cyclodextrin of constant density in lycopene oleo-resinous (content 6%) aqueous solution.Along with beta-cyclodextrin concentration rises, the Lyeopene uv-absorbing progressively increases (225～482nm cyclodextrin does not have uv-absorbing).
Fig. 3 is Hildebrand-Benesi equation and curve in hydroxypropyl-beta-cyclodextrin/lycopene oleo-resinous (content 50%) inclusion constant of UV mensuration.Method: the lycopene oleo-resinous of content 50% joins in the pH6.86 mixed phosphate salt buffer and is made into dilute solution, 274nm scan uv-absorbing A
0, with this dilute solution preparation hydroxypropyl-beta-cyclodextrin solution, the cyclodextrin soln of getting certain volume joins and changes cyclodextrin concentration C in the dilute solution
1～C
n(lycopene concentration is constant) gets the absorption A under the different cyclodextrin concentrations
1～A
n, calculate Δ A=A
n-A
0, with 1/ Δ A 1/C is mapped, promptly get the Hildebrand-Benesi equation, by the intercept/slope inclusion constant K a:1179M of straight line formula
-1
Fig. 4 is Hildebrand-Benesi equation and curve in beta-cyclodextrin/lycopene oleo-resinous (content 6%) inclusion constant of UV mensuration.Method: the lycopene oleo-resinous of content 6% joins in the pH6.86 mixed phosphate salt buffer and is made into dilute solution, 274nm scan uv-absorbing A
0, with this dilute solution preparation beta-cyclodextrin solution, the cyclodextrin soln of getting certain volume joins and changes cyclodextrin concentration C in the dilute solution
1～C
n(lycopene concentration is constant) gets the absorption A under the different cyclodextrin concentrations
1～A
n, calculate Δ A=A
n-A
0, with 1/ Δ A 1/C is mapped, promptly get the Hildebrand-Benesi equation, by the intercept/slope inclusion constant K a:416M of straight line formula
-1
Fig. 5 is the solubleness of hybrid ring cyclodextrin inclusion compound Lyeopene in water of hydroxypropyl-beta-cyclodextrin, beta-cyclodextrin and different ratios hydroxypropyl-beta-cyclodextrin.
Fig. 6 is a hydroxypropyl-beta-cyclodextrin relation with contents in cost performance (Y/X) and the hybrid ring dextrin.Y=solubilising degree; X=price rising multiple.
Embodiment
Embodiment 2,800 gram beta-cyclodextrins are mixed with 200 gram hydroxypropyl-beta-cyclodextrins, and preparation becomes the hybrid ring dextrin that contains hydroxypropyl-beta-cyclodextrin 20%, mixes 1000 ml pure waters, stir, make into suspensoid, add the Lyeopene raw material of 100 gram content 70% under the room temperature, thorough mixing, when changing even red mashed prod into by look red and white, the system that is ground to ground again 1 hour, 40 ℃ of vacuum-dryings get fluffy dark red solid inclusion compound, contain 6.36% Lyeopene in the solid.
Embodiment 3, substantially the same manner as Example 1, but 5 gram beta-cyclodextrins are mixed with 495 gram hydroxypropyl-beta-cyclodextrins, and preparation becomes the hybrid ring dextrin that contains hydroxypropyl-beta-cyclodextrin 99.0%, and add 125 milliliters of ethanol (with lycopene oleo-resinous equivalent), the preparation inclusion compound.
Embodiment 5, substantially the same manner as Example 1, but 250 gram beta-cyclodextrins are mixed with 250 gram hydroxypropyl-beta-cyclodextrins, preparation becomes the hybrid ring dextrin that contains hydroxypropyl-beta-cyclodextrin 50.0%, add 100 and restrain the lycopene oleo-resinous that contains Lyeopene 6%, stirred 24 hours under 40 ℃ of conditions.
Embodiment 7, and is substantially the same manner as Example 1, but adds the lycopene oleo-resinous that 167 grams contain Lyeopene 25%, stirs 48 hours under 30 ℃ of conditions, contains 6.26% Lyeopene in the solid clathrates of preparation.
Embodiment 9, and is substantially the same manner as Example 1, but adds the lycopene oleo-resinous that 125 grams contain Lyeopene 15%, contains 3.0% Lyeopene in the solids inclusion compound.
Embodiment 11, and is substantially the same manner as Example 2, grinds the preparation inclusion compound but add 100 milliliters of ethanol thorough mixing.Contain 23.7% Lyeopene in the solid clathrates.
Embodiment 13, and is substantially the same manner as Example 2, mixes with 990 gram hydroxypropyl-beta-cyclodextrins but add 10 gram beta-cyclodextrins, and preparation becomes the hybrid ring dextrin that contains hydroxypropyl-beta-cyclodextrin 99%.
Embodiment 15, substantially the same manner as Example 2, but adding 500 gram beta-cyclodextrins mixes with 500 gram hydroxypropyl-beta-cyclodextrins, preparation becomes the hybrid ring dextrin that contains hydroxypropyl-beta-cyclodextrin 50%, mixes 2000 ml pure waters, adds the Lyeopene raw material of 200 gram content 70%, thorough mixing, ground 10 hours, system transition ground 1 hour when being even red mashed prod again, contained 11.7% Lyeopene in the solid clathrates.
Embodiment 17, and is substantially the same manner as Example 2, but adds the Lyeopene raw material of 330 gram content 70%, and thorough mixing ground 10 hours, and system transition ground 1 hour when being even red mashed prod again, contained 17.36% Lyeopene in the solid clathrates.
Embodiment 18, and is substantially the same manner as Example 2, but adds the Lyeopene raw material of 100 gram content 95%, and thorough mixing grinds, and system transition ground 1 hour when being even red mashed prod again, contained 8.63% Lyeopene in the solid clathrates.
Embodiment 19, and is substantially the same manner as Example 2, but the water yield that adds is 5000 ml pure waters.
Claims (8)
1. the inclusion of beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene, it is characterized in that, contain lycopene oleo-resinous or high purity Lyeopene in the inclusion compound, also contain beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin, wherein the mass ratio of lycopene oleo-resinous or high purity Lyeopene and hybrid ring dextrin is 1: 3～30, the beta-cyclodextrin in the hybrid ring dextrin and the mass ratio of hydroxypropyl-beta-cyclodextrin are 99: 1～1: 99, and its form is the red solid inclusion compound.
2. according to the inclusion of described beta-cyclodextrin of claim 1 and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene, it is characterized in that the ratio of described beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin is 4: 1.
3. according to the inclusion compound of described beta-cyclodextrin of claim 1 and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene, it is characterized in that the content of Lyeopene is 0.19%～23.7% in the described inclusion compound.
4. according to the inclusion compound of claim 1 or 2 or 3 described beta-cyclodextrins and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene, it is characterized in that described lycopene oleo-resinous raw material is: the lycopene oleo-resinous that contains Lyeopene 6%, 10%, 15% or 95%.
5. the preparation method of the inclusion compound of described beta-cyclodextrin of claim 1 and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene, it is characterized in that, step is: beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin are obtained the hybrid ring dextrin according to the mixed of 99: 1～1: 99 scope, again hybrid ring dextrin and water are mixed with suspensoid or solution, the mass ratio of hybrid ring dextrin and water is 1: 1～5, the lycopene oleo-resinous that adds mass ratio 1/3～1/30 amount then, logical rare gas element mixes stirring down, cooling, filter, washing, vacuum-drying, or direct drying under reduced pressure obtains inclusion compound after stirring cooling.
6. according to the preparation method of the inclusion compound of described beta-cyclodextrin of claim 5 and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene, it is characterized in that in the described hybrid ring dextrin, the mass ratio of beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin is 4: 1.
7. according to the preparation method of the inclusion compound of claim 5 or 6 described beta-cyclodextrins and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene, it is characterized in that described rare gas element is a nitrogen.
8. according to the preparation method of the inclusion compound of described beta-cyclodextrin of claim 7 and hydroxypropyl-beta-cyclodextrin mixed inclusion lycopene, it is characterized in that, the red inclusion compound for preparing is the solid preparation that is used for protective foods, or as foodstuff additive or food dye.
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| SI2690951T1 (en) * | 2011-03-27 | 2016-02-29 | Cellresin Technologies, Llc | Cyclodextrin compositions, articles, and methods |
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| CN105434406B (en) * | 2014-08-22 | 2018-03-27 | 南京生矶坊生物工程有限公司 | A kind of All-cislycopene preparation with strengthen immunity and preparation method thereof |
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