CN106729744A - A kind of preparation method of Co-Q10 hydroxypropyl beta cyclodextrin clathrate - Google Patents
A kind of preparation method of Co-Q10 hydroxypropyl beta cyclodextrin clathrate Download PDFInfo
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- CN106729744A CN106729744A CN201611218017.XA CN201611218017A CN106729744A CN 106729744 A CN106729744 A CN 106729744A CN 201611218017 A CN201611218017 A CN 201611218017A CN 106729744 A CN106729744 A CN 106729744A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
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Abstract
The invention discloses a kind of preparation method of Co-Q10 hydroxypropyl beta cyclodextrin clathrate, by Co-Q10 absolute ethyl alcohol ultrasonic dissolution, the ethanol solution of Co-Q10 is obtained；By in the ethanol solution instillation hydroxypropyl beta cyclodextrin aqueous solution of CoQ10, stirred in drop, continue constant temperature stirring after dripping, room temperature is naturally cooled to, is refrigerated, suction filtration, add equivalent distilled water suction filtration, lucifuge is volatilized naturally, is rinsed with 3 suction filtrations of petroleum ether point, obtains Co-Q10 hydroxypropyl beta cyclodextrin clathrate.The inventive method, agitated method prepares products therefrom, can obtain the inclusion product of Co-Q10 inclusion rate higher, improves the stability of Co-Q10；Substantially increase solubility of the Co-Q10 in hydrophilic solution, it can be added in cosmetics and water-soluble liquid medicine as raw material.
Description
Technical field
The invention belongs to inclusion compound technical field, and in particular to a kind of system of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion
Preparation Method.
Background technology
Co-Q10 (CoenzymeQ10, CoQ10), also known as ubiquinone, is a kind of fat-soluble quinones chemical combination for being present in nature
Thing.The entitled CoQ10 of chemistry, is the important composition portion of function of human body energy manufacture
Point, it is widely present in the eukaryotic of majority, especially in mitochondria, it is one of important composition of respiratory chain, and
Contents of the CoQ10 on mitochondrial inner membrane is significantly larger than the content of respiratory chain other components, just because of its fat-soluble feature makes
It has mobility very high on mitochondrial inner membrane, so that its is particularly suitable as a kind of mobility electron transit mediator.
All there is CoQ10 in most cells in human body, show through numerous studies and report, appropriate supplement CoQ10 can be from root
Improve cell viability on source, promote body actively to carry out self-regeneration and adjustment, lift cellular energy levels, improve human immunity
The work(such as power, anti-oxidant enhancing, confrontation radical damage, anti-aging, enhancing human activity, antitumor, protection skin and heart
Energy.But, because CoQ10 hydrophobicitys are strong, relative molecular mass is larger, see the factors such as photo-labile limit its cosmetics,
The application and development in the field such as medicine and food.Therefore, generally improve CoQ10's using some special embeddings and inclusion technique
Stability, widens its range of application, such as micro-capsule, nano liposomes, cyclodextrin encapsulated, solid lipid nano granule technology.
HP-β-CD (HP- β-CD) is tool excellent pharmaceutic adjuvant with broad prospects for development.Its water solubility is very high
(≤75g/100mL), to alkali, light and heat stabilization.HP- β-CD are hardly decomposed metabolism in human body, also do not accumulate, orally
Gastrointestinal absorption is little after HP- β-CD, and distribution is little in blood and urine, and the overwhelming majority is excreted with excrement, and parenteral route is given
Also substantially excreted with urine during medicine, it is safe.Compared with beta-schardinger dextrin, biology is almost not involved in renal toxicity is low
Metabolism in vivo, does not accumulate, hemolytic and the low advantage of excitant.After research shows insoluble drug by HP- β-cdinclusions, not only
The solubility of medicine can be increased, drug bioavailability and stability can also be improved.At present, Japan, the U.S., Europe are just by this
One emerging auxiliary material is widely applied in pharmaceutical preparation and cosmetics, and many new medicinal preparations occurs, and China is also accumulating
Pole development and utilization this multi-functional emerging auxiliary material.
Research on application HP- β-CD to include CoQ10 yet there are no relevant report, and the present invention is exactly applied
The superior function such as the water solubility of HP- β-CD is high, security is high, solves the problems, such as that Co-Q10 solubility in water is small, and improve auxiliary
The stability and bioavailability of enzyme Q10, so as to widen Co-Q10 in cosmetics and the range of application of field of medicaments.
The content of the invention
It is an object of the invention to provide a kind of preparation method of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion, the method is carried
Co-Q10 high dissolubility and bioavilability in aqueous, solves CoQ10 insoluble problems in hydrophilic solution.
The technical solution adopted in the present invention is, a kind of preparation method of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion,
Specifically include following steps：
Step 1, by Co-Q10 absolute ethyl alcohol ultrasonic dissolution, obtains the ethanol solution of Co-Q10；
Step 2, by the ethanol solution instillation HP-β-CD aqueous solution of CoQ10, stirs in drop, drips
Continue constant temperature stirring afterwards, naturally cool to room temperature, refrigerate, suction filtration adds equivalent distilled water suction filtration, and lucifuge is volatilized naturally, use
3 suction filtrations of petroleum ether point are rinsed, and obtain Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion.
The features of the present invention is also resided in：
The concentration of Co-Q10 is 0.2-0.6g/L in the ethanol solution of Co-Q10 in step 1.
HP-β-CD concentration is 0.4-0.6g/ml in the HP-β-CD aqueous solution in step 2.
HP- β-CD and Co-Q10 mass ratio are 10-30 in step 2:1.
Temperature is maintained at during the ethanol solution of CoQ10 is instilled into the HP-β-CD aqueous solution in step 2
30-70 DEG C, constant temperature stirring 60-180min is continued after dripping.
Refrigerated storage temperature is 0-10 DEG C in step 2, and the time is 1-10h.
The beneficial effects of the invention are as follows the preparation method of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion of the present invention, through stirring
Mix process prepares products therefrom, can obtain the inclusion product of Co-Q10 inclusion rate higher, improves the stability of Co-Q10.
Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion prepared by preparation method of the present invention, can substantially increase Co-Q10 and exist
Solubility in hydrophilic solution, it can be added in cosmetics and water-soluble liquid medicine as raw material.Solve coenzyme
Undissolved problems of the Q10 in hydrophilic solution, greatly improves the scope of application of Co-Q10, is that Co-Q10 is being eaten
Product, medicine and cosmetic field have widened application idea, have important practical significance.
Brief description of the drawings
Fig. 1 is the microscope scanning figure of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion prepared by preparation method of the present invention；
Fig. 2 is the microscope scanning figure of HP-β-CD；
Fig. 3 is the physical mixed of Co-Q10, Co-Q10 and HP-β-CD prepared by preparation method of the present invention
Thing, Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion, the differential heating scan analysis of four kinds of materials of HP-β-CD
(DSC) spectrogram is determined；
A- Co-Q10s in figure；B- Co-Q10s and HP-β-CD physical mixture；C- inclusion compounds；D- hydroxypropyls-
Beta-schardinger dextrin；
Fig. 4 is infrared spectrum analysis (IR) spectrogram of Co-Q10；
Fig. 5 is infrared spectrum analysis (IR) spectrogram of HP-β-CD；
Fig. 6 is infrared spectrum analysis (IR) spectrogram of Co-Q10 and HP-β-CD physical mixture；
Fig. 7 is infrared spectrum analysis (IR) spectrum of the Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion that the present invention is prepared
Figure.
Specific embodiment
The present invention is described in detail with reference to the accompanying drawings and detailed description.
The preparation method of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion of the present invention, specifically includes following steps：
Step 1, by Co-Q10 absolute ethyl alcohol ultrasonic dissolution, obtains the ethanol solution of Co-Q10；The ethanol of Co-Q10
The concentration of Co-Q10 is 0.2-0.6g/L in solution.
Step 2, it is 0.4-0.6g/ml that the ethanol solution of CoQ10 is instilled into HP-β-CD concentration, hydroxypropyl-
(wherein HP- β-CD are 10-30 with Co-Q10 mass ratio in the beta-schardinger dextrin aqueous solution：1), temperature is maintained at 30-70 DEG C in drop
Stirring, continues constant temperature stirring 60-180min after dripping, naturally cool to room temperature, in 0-10 DEG C of refrigerator cold-storage 1-10h, suction filtration,
Add equivalent distilled water suction filtration, lucifuge is volatilized naturally, rinsed with points of 3 times suction filtrations of petroleum ether, obtain Co-Q10 hydroxy propyl-Beta-
Cyclodextrin inclusion compound.
Co-Q10 hydroxy propyl-Beta-ring that HP-β-CD and the present invention are obtained is compared in observation under inverted microscope
Cyclodextrin inclusion compound, as a result as depicted in figs. 1 and 2, find Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion volume substantially than HP- β-
CD increases, and illustrates that Co-Q10 is included in the inner chamber of HP-β-CD.
Differential heating scan analysis (DSC) of the Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion that the present invention is obtained is used
METTLER STAR System types differential thermal analyzer is determined, N2Air-flow protection, empty aluminium crucible is used as reference substance, sweep limits 20
~180 DEG C, 10 DEG C/min of heating rate is determined.Result is as shown in Figure 3.DSC measurement results show：HP-β-CD exists
80.20 DEG C have a somewhat recessed widthization endothermic peak, and now HP-β-CD is amorphous state；Co-Q10 is at 54.12 DEG C
There is sharp fusing point endothermic peak, Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion is only shown in the range of temperature of the measurement at 90.35 DEG C
The fusing point absworption peak of Co-Q10 is had no to HP-β-CD amorphous state absworption peak, shows there is new material to generate, led to
Cross the heat endurance that clathration improves Co-Q10.
By HP-β-CD, Co-Q10 HP-β-CD physical mixture, Co-Q10 hydroxy propyl-Beta-ring
FTIS (BRUKER T-27 types, Brooker are used after cyclodextrin inclusion compound and Co-Q10 difference KBr compressing tablets
Germany), 4000~400cm of spectral region- 1, resolution ratio 4.000cm- 1, scanning times 10 times.Measurement result is as shown in figs. 4-7.
The results of FT-IR shows：There is strong saturation C-H stretching vibration peaks in Co-Q10,2850cm has at 2963/cm
There is strong ketone group characteristic absorption peak in middle intensity saturation C-O stretching vibration peaks, 1647/cm, 1610/cm has strong benzoquinones feature to inhale
Peak is received, 1264/cm, 1287/cm have a strong benzoquinones ring C-O out-of-plane bending vibrations peak, and the characteristic peak of HP-β-CD
Near 1000/cm.Co-Q10 HP-β-CD physical mixture is included for Co-Q10 HP-β-CD
The characteristic peak of the superposition Co-Q10 of thing has embodiment, and the characteristic absorption peak of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion is equal
Disappear, show that Co-Q10 molecule is included in HP- β-CD inner chamber.
Precision weighs Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion and Co-Q10 and uses water and Co-Q10 petroleum ether respectively
Be settled in transparent measuring bottle, irradiated under daylight, respectively 1,2,4,6,10,14,18,24h point in time sampling, the aqueous solution utilizes stone
Determined by ultraviolet spectrophotometry Co-Q10 content is used after oily ether extraction, is determined respectively and counting loss amount and loss late, determined
Result is shown in as shown in table 1.The petroleum ether solution of Co-Q10 loss late under the natural daylight irradiation of 24 hours is 51.16%, and
The inclusion compound of Co-Q10 24 hourly loss rates under same experiment condition are 3.53%, as a result show Co-Q10 by hydroxypropyl
Its optical stability is improve after group-beta-cyclodextrin inclusion.
The inclusion compound of table 1 and the stability comparative test result of Co-Q10 is not included
Embodiment 1
Step 1, by Co-Q10 absolute ethyl alcohol ultrasonic dissolution, obtains the ethanol solution of Co-Q10；The ethanol of Co-Q10
The concentration of Co-Q10 is 0.2g/L in solution.
Step 2, it is 0.5g/ml that the ethanol solution of CoQ10 is instilled into HP-β-CD concentration, hydroxy propyl-Beta-ring
(wherein HP- β-CD are 10 with Co-Q10 mass ratio in dextrin in aqueous solution：1), temperature is maintained at 70 DEG C and is stirred in drop, is added dropwise
Continue constant temperature stirring 120min after complete, naturally cool to room temperature, in 0 DEG C of refrigerator cold-storage 1h, suction filtration adds equivalent distilled water and takes out
Filter, lucifuge is volatilized naturally, is rinsed with 3 suction filtrations of petroleum ether point, obtains Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion.
Embodiment 2
Step 1, by Co-Q10 absolute ethyl alcohol ultrasonic dissolution, obtains the ethanol solution of Co-Q10；The ethanol of Co-Q10
The concentration of Co-Q10 is 0.3g/L in solution.
Step 2, it is 0.6g/ml that the ethanol solution of CoQ10 is instilled into HP-β-CD concentration, hydroxy propyl-Beta-ring
(wherein HP- β-CD are 20 with Co-Q10 mass ratio in dextrin in aqueous solution：1), temperature is maintained at 60 DEG C and is stirred in drop, is added dropwise
Continue constant temperature stirring 180min after complete, naturally cool to room temperature, in 2 DEG C of refrigerator cold-storage 8h, suction filtration adds equivalent distilled water and takes out
Filter, lucifuge is volatilized naturally, is rinsed with 3 suction filtrations of petroleum ether point, obtains Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion.
Embodiment 3
Step 1, by Co-Q10 absolute ethyl alcohol ultrasonic dissolution, obtains the ethanol solution of Co-Q10；The ethanol of Co-Q10
The concentration of Co-Q10 is 0.5g/L in solution.
Step 2, it is 0.4g/ml that the ethanol solution of CoQ10 is instilled into HP-β-CD concentration, hydroxy propyl-Beta-ring
(wherein HP- β-CD are 30 with Co-Q10 mass ratio in dextrin in aqueous solution：1), temperature is maintained at 40 DEG C and is stirred in drop, is added dropwise
Continue constant temperature stirring 90min after complete, naturally cool to room temperature, in 5 DEG C of refrigerator cold-storage 3h, suction filtration adds equivalent distilled water and takes out
Filter, lucifuge is volatilized naturally, is rinsed with 3 suction filtrations of petroleum ether point, obtains Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion.
Embodiment 4
Step 1, by Co-Q10 absolute ethyl alcohol ultrasonic dissolution, obtains the ethanol solution of Co-Q10；The ethanol of Co-Q10
The concentration of Co-Q10 is 0.6g/L in solution；
Step 2, it is 0.5g/ml that the ethanol solution of CoQ10 is instilled into HP-β-CD concentration, hydroxy propyl-Beta-ring
(wherein HP- β-CD are 25 with Co-Q10 mass ratio in dextrin in aqueous solution：1), temperature is maintained at 30 DEG C and is stirred in drop, is added dropwise
Continue constant temperature stirring 60min after complete, naturally cool to room temperature, in 10 DEG C of refrigerator cold-storage 10h, suction filtration adds equivalent distilled water
Suction filtration, lucifuge is volatilized naturally, is rinsed with 3 suction filtrations of petroleum ether point, obtains Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion.
Claims (6)
1. a kind of preparation method of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion, it is characterised in that specifically include following steps：
Step 1, by Co-Q10 absolute ethyl alcohol ultrasonic dissolution, obtains the ethanol solution of Co-Q10；
Step 2, by the ethanol solution instillation HP-β-CD aqueous solution of CoQ10, stirs in drop, drips follow-up
Continuous constant temperature stirring, naturally cools to room temperature, refrigerates, and suction filtration adds equivalent distilled water suction filtration, and lucifuge is volatilized naturally, uses oil
3 suction filtrations of ether point are rinsed, and obtain Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion.
2. the preparation method of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion according to claim 1, it is characterised in that step
The concentration of Co-Q10 is 0.2-0.6g/L in the ethanol solution of Co-Q10 in rapid 1.
3. the preparation method of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion according to claim 1, it is characterised in that step
HP-β-CD concentration is 0.4-0.6g/ml in the HP-β-CD aqueous solution in rapid 2.
4. the preparation method of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion according to claim 1, it is characterised in that step
HP- β-CD and Co-Q10 mass ratio are 10-30 in rapid 2：1.
5. the preparation method of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion according to claim 1, it is characterised in that step
Temperature is maintained at 30-70 DEG C during the ethanol solution of CoQ10 is instilled into the HP-β-CD aqueous solution in rapid 2, is added dropwise
Continue constant temperature stirring 60-180min after complete.
6. the preparation method of Co-Q10 hydroxypropyl-beta-cyclodextrin inclusion according to claim 1, it is characterised in that step
Refrigerated storage temperature is 0-10 DEG C in rapid 2, and the time is 1-10h.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108143659A (en) * | 2018-02-27 | 2018-06-12 | 广州芸美生物科技有限公司 | The hydrogen-rich water composition and its production technology of a kind of beauty and skin care and its application in cosmetics |
| CN110075000A (en) * | 2019-04-19 | 2019-08-02 | 山东省药学科学院 | A kind of hydroxytyrosol inclusion compound and its preparation method and application |
| CN111374965A (en) * | 2018-12-28 | 2020-07-07 | 上海融澈水性材料有限公司 | Water-soluble coenzyme Q10 clathrate compound with high stability and preparation method thereof |
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| CN101053556A (en) * | 2006-04-14 | 2007-10-17 | 沈阳市万嘉生物技术研究所 | Water soluble coenzyme Q10 hydroxyl-beta-cyclodextrin inclusion compound and its preparation method |
| CN102127172A (en) * | 2010-12-30 | 2011-07-20 | 云南师范大学 | Water-soluble coenzyme Q 10 compound and preparation method thereof |
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Patent Citations (2)
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| CN101053556A (en) * | 2006-04-14 | 2007-10-17 | 沈阳市万嘉生物技术研究所 | Water soluble coenzyme Q10 hydroxyl-beta-cyclodextrin inclusion compound and its preparation method |
| CN102127172A (en) * | 2010-12-30 | 2011-07-20 | 云南师范大学 | Water-soluble coenzyme Q 10 compound and preparation method thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108143659A (en) * | 2018-02-27 | 2018-06-12 | 广州芸美生物科技有限公司 | The hydrogen-rich water composition and its production technology of a kind of beauty and skin care and its application in cosmetics |
| CN108143659B (en) * | 2018-02-27 | 2021-04-06 | 广州芸美生物科技有限公司 | Hydrogen-rich water composition for beautifying and protecting skin, production process thereof and application thereof in cosmetics |
| CN111374965A (en) * | 2018-12-28 | 2020-07-07 | 上海融澈水性材料有限公司 | Water-soluble coenzyme Q10 clathrate compound with high stability and preparation method thereof |
| CN111374965B (en) * | 2018-12-28 | 2024-01-16 | 上海融澈水性材料有限公司 | Water-soluble coenzyme Q10 inclusion compound with high stability and preparation method thereof |
| CN110075000A (en) * | 2019-04-19 | 2019-08-02 | 山东省药学科学院 | A kind of hydroxytyrosol inclusion compound and its preparation method and application |
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Application publication date: 20170531 |