CN1534013A - Preparation method of water soluble curcumin composition salt - Google Patents
Preparation method of water soluble curcumin composition salt Download PDFInfo
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- CN1534013A CN1534013A CNA031120539A CN03112053A CN1534013A CN 1534013 A CN1534013 A CN 1534013A CN A031120539 A CNA031120539 A CN A031120539A CN 03112053 A CN03112053 A CN 03112053A CN 1534013 A CN1534013 A CN 1534013A
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- curcumine
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing the water-soluble composite curcumin salt, which has the greatly increased biological utilization rate, is disclosed.
Description
(1) technical field:
The present invention relates to a kind of preparation method of water-soluble curcumine composite salt.
(2) background technology:
Curcumine (Curcumin) is a kind of phenols pigment composition that extraction separation obtains from plant turmeric (Curcuma longa) foundation, and pharmacological action is comparatively widely arranged.Mainly show anti-oxidant, cholagogic, antibiotic, antitumor, reducing blood-fat, inhibition platelet aggregation, strengthen aspects such as fibrinolytic.But because curcumine is insoluble in water, so its bioavailability is not high.
The preparation method who the purpose of this invention is to provide a kind of water-soluble curcumine composite salt soluble in water.
(3) summary of the invention:
The invention provides a kind of water-soluble curcumine composite salt and preparation method thereof, this method comprises that (general formula is HOOC (CH with following formula (II) curcumine and organic dibasic acid
2)
nThe monounsaturated dicarboxylic acid of COOH and structural formula are the butene dioic acid of HOOCCH=CHCOOH), under the situation that organic solvent exists, reacted in 4 hours in 56 ℃ of reflux, with products therefrom in 56 ℃ of basic aminoacidss with following formula [(III) arginine, (IV) Methionin, (V) Histidine], reflux reaction in 1 hour, cool off then, filter, reduce pressure, promptly got a kind of composite salt in 3 hours, be water-soluble curcumine composite salt 45 ℃ of dryings.
Owing to adopt aforesaid method that curcumine is made for water-soluble curcumine composite salt, therefore improved the curcumine bioavailability greatly, have that use range is wide, the availability advantages of higher.
(4) embodiment:
Reaction principle of the present invention is as follows:
(general formula is HOOC (CH for curcumine and organic dibasic acid
2)
nThe monounsaturated dicarboxylic acid of COOH and structural formula are the butene dioic acid of HOOCCH=CHCOOH), under the situation that organic solvent exists, reacted in 4 hours in 56 ℃ of reflux, with products therefrom in 56 ℃ with arginine or basic aminoacidss such as Methionin or Histidine, reflux reaction in 1 hour, cool off then, filter, reduce pressure, promptly got a kind of composite salt in 3 hours, be water-soluble curcumine composite salt 45 ℃ of dryings.
Concrete reaction is as follows:
Wherein when n=0, promptly HOOCCOOH is a hexanodioic acid
HOOCCH during n=1
2COOH is a propanedioic acid
HOOCCH during n=2
2CH
2COOH is a Succinic Acid
HOOCCH during n=3
2CH
2CH
2COOH is a pentanedioic acid
HOOCCH during n=4
2CH
2CH
2CH
2COOH is a hexanodioic acid
Then above-mentioned product is formed Water Soluble Compound salt with the basic aminoacids reaction respectively
Wherein when n=0, promptly HOOCCOOH is a hexanodioic acid
HOOCCH during n=1
2COOH is a propanedioic acid
HOOCCH during n=2
2CH
2COOH is a Succinic Acid
HOOCCH during n=3
2CH
2CH
2COOH is a pentanedioic acid
HOOCCH during n=4
2CH
2CH
2CH
2COOH is a hexanodioic acid
Embodiment 1:
Get curcumine 1.78 grams, Succinic Acid 1 gram adds in the flask, adds 100ml acetone again, 2 dense H
2SO
4, reflux 4 hours, 56 ℃ add arginine 1.7 grams in above-mentioned reaction system, reflux 1 hour, cold filtration, decompression, 45 ℃ of dryings 3 hours, 3.5 gram products.
Embodiment 2:
Get curcumine 2 grams, Succinic Acid 1.4 grams add acetone 50ml, normal hexane 50ml, 2 dense H
2SO
4, reflux 4 hours is filtered drying under reduced pressure and is got 3 gram black precipitates, adds 1.8 gram arginine again, and reflux is filtered drying under reduced pressure and is got 3.8 gram yellow crystal products.
Embodiment 3:
Curcumine 2 grams, butene dioic acid 1.3 grams add in the 100ml acetone thermal backflow 2 hours.Add 2 gram arginine, thermal backflow 2 hours will be filtered thing and be placed 30 ℃ of drying under reduced pressure to get the yellow product of 3.7 grams.
Embodiment 4:
Curcumine 2 grams, Succinic Acid 1.8 grams add in the 100ml acetone thermal backflow 2 hours.Add 1.6 gram Methionins, thermal backflow 2 hours will be filtered thing and be placed 30 ℃ of drying under reduced pressure to get the yellow product of 3.1 grams.
Embodiment 5:
Get curcumine 1.8 grams, hexanodioic acid 1.4 grams add in the flask, add 100ml acetone again, 2 dense H
2SO
4, reflux 4 hours adds Histidine 1.5 grams in above-mentioned reaction system, reflux 1 hour, cold filtration, decompression, 45 ℃ of dryings 3 hours, 3.1 gram products.
Embodiment 6:
Get curcumine 1.3 grams, propanedioic acid 0.8 gram adds in the flask, adds 100ml acetone again, 2 dense H
2SO
4, reflux 4 hours adds arginine 1.3 grams in above-mentioned reaction system, reflux 1 hour, cold filtration, decompression, 45 ℃ of dryings 3 hours, 2.8 gram products.
Claims (1)
1, a kind of water-soluble curcumine composite salt and preparation method thereof, this method comprise that (general formula is HOOC (CH with following formula (II) curcumine and organic dibasic acid
2)
nThe monounsaturated dicarboxylic acid of COOH and structural formula are the butene dioic acid of HOOCCH=CHCOOH), under the situation that organic solvent exists, reacted in 4 hours in 56 ℃ of reflux, with products therefrom in 56 ℃ of basic aminoacidss with following formula [(III) arginine, (IV) Methionin, (V) Histidine], reflux reaction in 1 hour, cool off then, filter, reduce pressure, promptly got a kind of composite salt in 3 hours, be water-soluble curcumine composite salt 45 ℃ of dryings.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031120539A CN1312106C (en) | 2003-03-28 | 2003-03-28 | Preparation method of water soluble curcumin composition salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031120539A CN1312106C (en) | 2003-03-28 | 2003-03-28 | Preparation method of water soluble curcumin composition salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1534013A true CN1534013A (en) | 2004-10-06 |
| CN1312106C CN1312106C (en) | 2007-04-25 |
Family
ID=34283605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB031120539A Expired - Fee Related CN1312106C (en) | 2003-03-28 | 2003-03-28 | Preparation method of water soluble curcumin composition salt |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1312106C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009144220A1 (en) * | 2008-05-29 | 2009-12-03 | Universite Libre De Bruxelles | Water soluble curcumin compositions for use in anti-cancer and anti-inflammatory therapy |
| WO2011106691A2 (en) * | 2010-02-26 | 2011-09-01 | Research Foundation Of The City University Of New York | Curcumin derivatives |
| WO2017162511A1 (en) * | 2016-03-25 | 2017-09-28 | Biopteq Sprl | Curcumin purification |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8383865B2 (en) | 2007-04-17 | 2013-02-26 | Codman & Shurtleff, Inc. | Curcumin derivatives |
| EP2749552B1 (en) | 2007-04-17 | 2015-11-18 | Codman & Shurtleff, Inc. | Curcumin-resveratrol hybrids |
| US7745670B2 (en) | 2008-06-27 | 2010-06-29 | Codman & Shurtleff, Inc. | Curcumin-Resveratrol hybrid molecule |
| US7985776B2 (en) | 2008-06-27 | 2011-07-26 | Codman & Shurtleff, Inc. | Iontophoretic delivery of curcumin and curcumin analogs for the treatment of Alzheimer's Disease |
| US7723515B1 (en) | 2009-01-26 | 2010-05-25 | Codman & Shurtleff, Inc. | Methylene blue—curcumin analog for the treatment of alzheimer's disease |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10114649A (en) * | 1996-10-15 | 1998-05-06 | Dokutaazu Kosumeteikusu:Kk | Improver for aqueous body fluid and composition for oral administration comprising the same |
| DE19956848A1 (en) * | 1999-11-26 | 2001-05-31 | Basf Ag | Curcumin formulations |
| KR20020073847A (en) * | 2001-03-16 | 2002-09-28 | 주식회사 바이오시너젠 | Composition for preventing or treating dementia comprising curcumin or extract of curcuma aromatica |
-
2003
- 2003-03-28 CN CNB031120539A patent/CN1312106C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009144220A1 (en) * | 2008-05-29 | 2009-12-03 | Universite Libre De Bruxelles | Water soluble curcumin compositions for use in anti-cancer and anti-inflammatory therapy |
| US8772265B2 (en) | 2008-05-29 | 2014-07-08 | Universite Libre De Bruxelles | Water soluble curcumin compositions for use in anti-cancer and anti-inflammatory therapy |
| WO2011106691A2 (en) * | 2010-02-26 | 2011-09-01 | Research Foundation Of The City University Of New York | Curcumin derivatives |
| WO2011106691A3 (en) * | 2010-02-26 | 2011-12-15 | Research Foundation Of The City University Of New York | Curcumin derivatives |
| WO2017162511A1 (en) * | 2016-03-25 | 2017-09-28 | Biopteq Sprl | Curcumin purification |
| US10336677B2 (en) | 2016-03-25 | 2019-07-02 | Biopteq Sprl | Curcumin purification |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1312106C (en) | 2007-04-25 |
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| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
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| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20070425 Termination date: 20100328 |