CN102309766A - Method for improving water solubility of xanthohumol - Google Patents
Method for improving water solubility of xanthohumol Download PDFInfo
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- CN102309766A CN102309766A CN201110122090A CN201110122090A CN102309766A CN 102309766 A CN102309766 A CN 102309766A CN 201110122090 A CN201110122090 A CN 201110122090A CN 201110122090 A CN201110122090 A CN 201110122090A CN 102309766 A CN102309766 A CN 102309766A
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- xanthohumol
- cyclodextrin
- clathrate
- water miscible
- diluted alcohol
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Abstract
The invention relates to a method for improving water solubility of xanthohumol, belonging to the field of fine chemical industry. The method comprises the following steps: dissolving xanthohumol and cyclodextrin in diluted alcohol; recovering alcohol by reduced-pressure distillation; filtering to obtain an aqueous solution of a cyclodextrin-xanthohumol clathrate compound; and drying to obtain a cyclodextrin-xanthohumol clathrate compound powder product. By the method provided by the invention, the water solubility of xanthohumol is improved, and the solubility of the formed cyclodextrin-xanthohumol clathrate compound in water at the room temperature is more than 10%, thereby creating conditions for wide application of xanthohumol.
Description
Technical field
The invention belongs to field of fine chemical, be specifically related to the method that xanthohumol character is improved.
Background technology
Xanthohumol is a kind of composition in the Flos lupuli (Flos Humuli Lupuli), and it induces carcinogen to separate the catalytic activity of toxenzyme through suppressing procarcinogen to the enzymatic activity that carcinogen changes, thereby forbids that cancerous cell growth in early days plays the effect of effective prophylaxis of cancer; Xanthohumol also has the effect of anticancer amplification; Prevention, treatment diabetes and arteriosclerotic effect; Has antioxidation; Have estrogenic effect and can improve climacteric syndrome, thereby cause the very big attention of research worker, have a extensive future in fields such as food, medicine, health product, cosmetics.
Xanthohumol is prone to be dissolved in ethanol, dimethyl sulfoxine, methanol, the ethyl acetate isopolarity organic solvent, but in water, does not dissolve, and this extensive use for xanthohumol forms obstacle.Be to make the medicated beer that is rich in xanthohumol in the Chinese patent 200580039733.5 of TA-XAN company application; The Fructus Hordei Germinatus (parched to brown) medicated beer of xanthohumol is rich in preparation earlier; Fructus Hordei Germinatus (parched to brown) medicated beer is added in the medicated beer, Fructus Hordei Germinatus (parched to brown) medicated beer contains xanthohumol less than 1500 mg/litre, and manufacture process is loaded down with trivial details again.The solution that proposes to above problem the present invention is to improve its dissolubility in water through the embedding xanthohumol.
Cyclodextrin is under the enzyme effect, and by the α-1 that starch generates, the 4-glycosidic bond connects, joins end to end, by the oligosaccharide that 6～12 glucose units are formed, and it can comprise complex with some ions or organic molecule formation.Utilize the ability of the hydrophobic cavity generation inclusion complex of cyclodextrin; Can make many active component and cyclodextrin generation complex in the food industry, reach stable, reduce oxidation, passivation heliosensitivity and thermal sensitivity by the inclusion complex physico-chemical property; Strengthen water-soluble, reduce volatile purpose.Cyclodextrin can increase dissolubility and the dissolution velocity of the bad medicine of some water solublity in water effectively, thereby processes injection like the dissolubility that prostaglandin-cyclodextrin clathrate can increase principal agent.It can also improve the stability and the bioavailability of medicine (like intestinal recovering particles volatile oil); Reduce the bad smell or the bitterness of medicine (like Herba Andrographis); Reduce the stimulation and the toxic and side effects of medicine (like diclofenac sodium); And make medicine (example hydrochloric acid berberine) slow release and improve dosage form.In cosmetics are made, utilize the ability of the hydrophobic cavity generation inclusion complex of cyclodextrin, cyclodextrin can be made emulsifying agent and quality improver.Cyclodextrin is used with surfactant can reduce the stimulation of surfactant to skin in shampoo and the cleaning agent for kitchen; Utilize cyclodextrin can also remove the oil stain on the fabric; In dyeing, the use cyclodextrin can significantly reduce the initial dyeing rate of dyestuff, improves the tinctorial yield of level-dyeing property and fiber.
Summary of the invention
The technical problem that the present invention will solve provides a kind of water miscible method of xanthohumol of improving.
The scheme of technical solution problem of the present invention is to use the cyclodextrin embedding xanthohumol, forms cyclodextrin-xanthohumol clathrate, because clathrate dissolubility in water is bigger, thereby reaches the object of the invention.
The method for preparing cyclodextrin-xanthohumol clathrate is carried out according to following steps:
1, under 30-70 ℃ of heating condition, xanthohumol and cyclodextrin are dissolved in the Diluted Alcohol, the distilling under reduced pressure recovered alcohol filters the aqueous solution that obtains cyclodextrin-xanthohumol clathrate; Said xanthohumol is meant the xanthohumol product of xanthohumol content at 10%-99%; Cyclodextrin is meant alpha-cyclodextrin or beta-schardinger dextrin-or gamma-cyclodextrin or hydroxypropyl; Diluted Alcohol is meant the ethanol of percent by volume 10-50%; The ratio of xanthohumol and cyclodextrin is mol ratio 1/1-1/10; The Diluted Alcohol consumption is xanthohumol and cyclodextrin gross weight 10-40 a times;
2, the aqueous solution of cyclodextrin-xanthohumol clathrate obtains cyclodextrin-xanthohumol clathrate powder-product through drying, and described drying can be spray drying or lyophilization.
The preferred hydroxypropyl of cyclodextrin wherein;
The ethanol of the preferred volume percentage ratio 20-40% of Diluted Alcohol;
The preferred proportion of xanthohumol and cyclodextrin is mol ratio 1/1-1/5;
The 20-30 that preferred Diluted Alcohol consumption is xanthohumol and cyclodextrin gross weight doubly;
Method provided by the invention has been improved the water solublity of xanthohumol, and the dissolubility under the xanthohumol of formation-cyclodextrin clathrate room temperature in water is greater than 10%, for condition has been created in its extensive use.
The specific embodiment
Embodiment 1
The xanthohumol (containing 0.01 mole of xanthohumol) and hydroxypropyl 150 grams (0.1 mole) of 35 grams 10% are dissolved in 4000 grams, 50% ethanol; The distilling under reduced pressure recovered alcohol filters the aqueous solution that obtains cyclodextrin-xanthohumol clathrate.
2. the aqueous solution of cyclodextrin-xanthohumol clathrate obtains cyclodextrin-xanthohumol clathrate powder-product through spray drying, shallow green powder 180 grams.
Embodiment 2
The xanthohumol (containing 0.01 mole of xanthohumol) and hydroxypropyl 30 grams (0.02 mole) of 7 grams 50% are dissolved in 1000 grams, 30% ethanol; The distilling under reduced pressure recovered alcohol filters the aqueous solution that obtains cyclodextrin-xanthohumol clathrate.
2. the aqueous solution of cyclodextrin-xanthohumol clathrate obtains cyclodextrin-xanthohumol clathrate powder-product through spray drying, buff powder 36 grams.
Embodiment 3
The xanthohumol (containing 0.01 mole of xanthohumol) and hydroxypropyl 15 grams (0.01 mole) of 3.6 grams 98% are dissolved in 250 grams, 20% ethanol gradually; The distilling under reduced pressure recovered alcohol filters the aqueous solution that obtains cyclodextrin-xanthohumol clathrate.
2. the aqueous solution lyophilization of cyclodextrin-xanthohumol clathrate obtains cyclodextrin-xanthohumol clathrate powder-product, buff powder 19 grams.Dissolubility under its clathrate room temperature in water is 15%.
Claims (5)
1. one kind is improved the water miscible method of xanthohumol, it is characterized in that adopting following steps to accomplish:
(1) under 30-70 ℃ of heating condition, xanthohumol and cyclodextrin are dissolved in the Diluted Alcohol, the distilling under reduced pressure recovered alcohol filters the aqueous solution that obtains cyclodextrin-xanthohumol clathrate; Said xanthohumol is meant the xanthohumol product of xanthohumol content at 10%-99%; Cyclodextrin is meant alpha-cyclodextrin or beta-schardinger dextrin-or gamma-cyclodextrin or hydroxypropyl; Diluted Alcohol is meant the ethanol of percent by volume 10-50%; The ratio of xanthohumol and cyclodextrin is mol ratio 1/1-1/10; The Diluted Alcohol consumption is xanthohumol and cyclodextrin gross weight 10-40 a times;
(2) aqueous solution of cyclodextrin-xanthohumol clathrate obtains cyclodextrin-xanthohumol clathrate powder-product through drying, and described drying can be spray drying or lyophilization.
2. the water miscible method of xanthohumol of improving according to claim 1, it is characterized in that: cyclodextrin is a hydroxypropyl.
3. the water miscible method of xanthohumol of improving according to claim 1 is characterized in that: the ethanol of selecting percent by volume 20-40% for use of Diluted Alcohol.
4. the water miscible method of xanthohumol of improving according to claim 1, it is characterized in that: the ratio of xanthohumol and cyclodextrin is mol ratio 1/1-1/5.
5. the water miscible method of xanthohumol of improving according to claim 1 is characterized in that: the Diluted Alcohol consumption is xanthohumol and cyclodextrin gross weight 20-30 a times.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110122090A CN102309766A (en) | 2011-05-12 | 2011-05-12 | Method for improving water solubility of xanthohumol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110122090A CN102309766A (en) | 2011-05-12 | 2011-05-12 | Method for improving water solubility of xanthohumol |
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| Publication Number | Publication Date |
|---|---|
| CN102309766A true CN102309766A (en) | 2012-01-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110122090A Pending CN102309766A (en) | 2011-05-12 | 2011-05-12 | Method for improving water solubility of xanthohumol |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009108379A1 (en) * | 2008-02-27 | 2009-09-03 | Flaxan Gmbh & Co. Kg | Novel compositions containing xanthohumol-cyclodextrin complexes |
| WO2009126320A1 (en) * | 2008-04-11 | 2009-10-15 | Betal, Llc | Xanthohumol compositions and methods for treating skin diseases or disorders |
-
2011
- 2011-05-12 CN CN201110122090A patent/CN102309766A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009108379A1 (en) * | 2008-02-27 | 2009-09-03 | Flaxan Gmbh & Co. Kg | Novel compositions containing xanthohumol-cyclodextrin complexes |
| WO2009126320A1 (en) * | 2008-04-11 | 2009-10-15 | Betal, Llc | Xanthohumol compositions and methods for treating skin diseases or disorders |
Non-Patent Citations (1)
| Title |
|---|
| 朱盛山: "《药物新剂型》", 31 August 2003, 化学工业出版社 * |
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Application publication date: 20120111 |