CN1197786A - Oil-soluble tea polyphenol and its preparation - Google Patents
Oil-soluble tea polyphenol and its preparation Download PDFInfo
- Publication number
- CN1197786A CN1197786A CN 97118872 CN97118872A CN1197786A CN 1197786 A CN1197786 A CN 1197786A CN 97118872 CN97118872 CN 97118872 CN 97118872 A CN97118872 A CN 97118872A CN 1197786 A CN1197786 A CN 1197786A
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- CN
- China
- Prior art keywords
- oil
- acid
- soluble tea
- tea polyphenol
- polyphenol
- 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
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 20
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 20
- 241001122767 Theaceae Species 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 239000000047 product Substances 0.000 claims abstract description 9
- 239000000706 filtrate Substances 0.000 claims abstract description 8
- 238000005917 acylation reaction Methods 0.000 claims abstract description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 7
- 229930195729 fatty acid Natural products 0.000 claims abstract description 7
- 239000000194 fatty acid Substances 0.000 claims abstract description 7
- 238000004821 distillation Methods 0.000 claims abstract description 5
- 239000006227 byproduct Substances 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 31
- 244000269722 Thea sinensis Species 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- -1 fatty acid carboxylic acid halides Chemical class 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- 150000002632 lipids Chemical class 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 6
- 235000019198 oils Nutrition 0.000 claims description 6
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 6
- 229960004232 linoleic acid Drugs 0.000 claims description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- 239000005642 Oleic acid Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 4
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- 244000208060 Lawsonia inermis Species 0.000 claims description 2
- 235000021314 Palmitic acid Nutrition 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 229940022682 acetone Drugs 0.000 claims description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 229940043232 butyl acetate Drugs 0.000 claims description 2
- 239000003240 coconut oil Substances 0.000 claims description 2
- 235000019864 coconut oil Nutrition 0.000 claims description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 2
- 229940093499 ethyl acetate Drugs 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 229960002969 oleic acid Drugs 0.000 claims description 2
- 235000021313 oleic acid Nutrition 0.000 claims description 2
- 229940098695 palmitic acid Drugs 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 229960004274 stearic acid Drugs 0.000 claims description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 abstract description 5
- 238000001914 filtration Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 230000010933 acylation Effects 0.000 abstract 1
- 230000003064 anti-oxidating effect Effects 0.000 abstract 1
- 230000006837 decompression Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000004519 grease Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Fatty acid with 9-24 carbon atoms is acylated by adding acylating agent at 30-120 deg.c; and tea polyphenol solution in organic solvent is mixed with the above said acylation product at 40-80 deg.c and through filtration, reduced pressure distillation of the filtrate to remove organic solvent and side product and to obtain oil-soluble tea polyphenol. The said product can be dissolved in oil completely at any proportion and is stable and has obvious anti-oxidation and fresh-keeping effect.
Description
The present invention relates to a kind of tea-polyphenol and preparation method thereof.
Existing oil-soluble tea polyphenol is gone up by society at present, is actually the compound of tea-polyphenol and emulsifying agent.Because emulsified body in use can produce breakdown of emulsion, comes across in the grease so most of tea-polyphenol can become nebulous floating matter, this makes the visual appearance of oil product descend greatly.
The purpose of this invention is to provide a kind of tea-polyphenol and method for making that is dissolved in the grease.
The objective of the invention is to realize by following proposal:
The organic aliphatic acid that contains 8～24 carbon atoms is warmed to 30～120 ℃, and the ratio of splashing into is the acylating agent of 1: 1～1.5 mol ratios, carries out acylation reaction; Be solute with the tea-polyphenol then, organic solvent is a solvent, as reaction medium, its solution is warmed to 40～80 ℃, and the ratio of splashing into is the synthetics of the above-mentioned acylation reaction of 1: 1～5 weight ratios; 2～10 hours reaction times, reaction product after filtration, filtrate decompression is distilled into thickness oily matter.
Organic aliphatic acid is meant that a kind of or any kind that stearic acid, Palmiticacid, oleic acid, linolic acid, linolenic acid, palmitinic acid, coconut oil, oleic acid etc. contain in the lipid acid of 8～24 carbon atoms is mixed with arbitrary proportion; The optimal selection of organic aliphatic acid is the unsaturated organic aliphatic acid that contains 16～22 carbon atoms.Acylating agent is meant any in phosphorus trichloride, phosphorus pentachloride, sulfur oxychloride, aceticanhydride, the ketene; The optimal selection of acylating agent is a phosphorus trichloride.Organic solvent is meant any in methylene dichloride, ethylene dichloride, methyl acetate, ethyl acetate, propyl acetate, butylacetate, acetone, the sherwood oil; The optimal selection of organic solvent is an ethyl acetate.
A kind of method of producing oil-soluble tea polyphenol that is exclusively used in the steps include:
1. when the organic aliphatic acid that contains 8～24 carbon atoms being warmed to 30～120 ℃, the ratio of splashing into is the acylating agent of 1: 1～1.5 mol ratios, carries out acylation reaction, synthetic fatty acid carboxylic acid halides or anhydride ester derivs;
2. be solute with the tea-polyphenol, organic solvent is as solvent, and promptly reaction medium is warmed to 40～80 ℃ to its solution, and the ratio of splashing into is the above-mentioned lipid acid carboxylic acid halides or the anhydride ester derivs of 1: 1～5 weight ratios, synthetic oil-soluble tea polyphenol;
3. filter, remove filter residue;
4. filtrate is removed organic solvent and byproduct through underpressure distillation, and remaining henna thickness oily matter is synthetic oil-soluble tea polyphenol product.
Oil-soluble tea polyphenol of the present invention can any ratio be dissolved in the grease fully, and in the oil product course of processing, do not have any material and separate out, stable performance, prolonged preservation does not have precipitation, keeps original greasy color; The antioxygen fresh-keeping effect is obvious; And no side effects.
Embodiment one:
Linolic acid 100g is heated to 45 ℃, drips phosphorus pentachloride 75g, and insulation reaction 6 hours is not emitted to there being hydrogenchloride.Decompression steams phosphorus oxychloride, gets linolic acid acyl chlorides 106g.
Get tea-polyphenol 60g, be dissolved in the 300g ethyl acetate, be heated to 60 ℃, drip above-mentioned linolic acid acyl chlorides 106g, drip off insulation reaction and do not emit to there being hydrogenchloride.Cold filtration, filtrate decompression steam ethyl acetate and promptly get brown oil-soluble tea polyphenol.
Embodiment two:
100g soy(a)-bean oil fatty acid (fatty acid mixt that contains 16～18 carbon atoms) is mixed with the 37g aceticanhydride, be warming up to 110 ℃, steam byproduct of reaction acetic acid under the decompression, get soybean oil fatty acid anhydrides 97g.
Get tea-polyphenol 35g, be dissolved in the 170g ethyl acetate, feed a small amount of dry hydrogen chloride, be warming up to 78 ℃, drip above-mentioned soybean oil fatty acid anhydrides 97g, finished insulation reaction 8 hours, cold filtration, filtrate decompression boils off ethyl acetate, promptly gets oil-soluble tea polyphenol.
Embodiment three:
Get 80 grammeter oil extracted from rice husks acid, be heated to 50 ℃, in 1 hour, drip 20 gram phosphorus trichlorides, drip off insulation 1 hour, vacuum extracts remaining phosphorus trichloride, and static several minutes, upper strata oily matter is told, get 84 gram lipid acid acyl chlorides.
Get 60 gram tea-polyphenol with 240 gram acetic acid ethyl dissolutions, be heated to 60 ℃, in three hours, drip above-mentioned lipid acid acyl chlorides.Reaction finishes, and product is filtered, and discards filter residue.Filtrate steams ethyl acetate and hydrogenchloride with underpressure distillation, will steam condensation of gas, alkali cleaning, dried recovered ethyl acetate.Get the about 150g of product.This product can be dissolved in the grease with arbitrary proportion.
Claims (8)
1. an oil-soluble tea polyphenol is characterized in: contain the organic aliphatic acid of 8～24 carbon atoms, in the time of 30～120 ℃, splash into the acylating agent that carries out acylation reaction of 1: 1～1.5 mol ratios; With the tea-polyphenol is solute, and organic solvent is molten Ji, and its solution splashes into the synthetics of the above-mentioned acylation reaction of 1: 1～5 weight ratios in the time of 40～80 ℃; Its filtrate of underpressure distillation becomes thickness oily matter.
2. oil-soluble tea polyphenol according to claim 1 is characterized in that: described organic aliphatic acid is meant that a kind of or any kind that stearic acid, Palmiticacid, oleic acid, linolic acid, linolenic acid, palmitinic acid, coconut oil, oleic acid contain in the lipid acid of 8～24 carbon atoms is mixed with arbitrary proportion.
3. oil-soluble tea polyphenol according to claim 1 and 2 is characterized in that: the optimal selection of described organic aliphatic acid is the unsaturated organic aliphatic acid that contains 16～22 carbon atoms.
4. oil-soluble tea polyphenol according to claim 1 is characterized in that: described acylating agent is meant any in phosphorus trichloride, phosphorus pentachloride, sulfur oxychloride, aceticanhydride, the ketene.
5. according to claim 1 or 4 described oil-soluble tea polyphenols, it is characterized in that: the optimal selection of described acylating agent is a phosphorus trichloride.
6. oil-soluble tea polyphenol according to claim 1 is characterized in that: described organic solvent is meant any in methylene dichloride, ethylene dichloride, methyl acetate, ethyl acetate, propyl acetate, butylacetate, acetone, the sherwood oil.
7. according to claim 1 or 6 described oil-soluble tea polyphenols, it is characterized in that: the optimal selection of described organic solvent is an ethyl acetate.
8. one kind is exclusively used in the method for producing the described oil-soluble tea polyphenol of claim 1, the steps include:
1. the organic aliphatic acid that contains 8～24 carbon atoms is warmed to 30～120 ℃, drips the acylating agent of 1: 1～1.5 mol ratios, carry out acylation reaction, synthetic fatty acid carboxylic acid halides or anhydride ester derivs;
2. tea-polyphenol is a solute, organic solvent be reaction medium as solvent, its solution is warmed to 40～80 ℃, drip the above-mentioned lipid acid carboxylic acid halides or the anhydride ester derivs of 1: 1～5 weight ratios, the synthetic oil-soluble tea polyphenol of reaction;
3. filter, remove filter residue;
4. filtrate is removed organic solvent and byproduct through underpressure distillation, and remaining henna thickness oily matter is product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN97118872A CN1067675C (en) | 1997-11-06 | 1997-11-06 | Oil-soluble tea polyphenol and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN97118872A CN1067675C (en) | 1997-11-06 | 1997-11-06 | Oil-soluble tea polyphenol and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1197786A true CN1197786A (en) | 1998-11-04 |
| CN1067675C CN1067675C (en) | 2001-06-27 |
Family
ID=5175028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97118872A Expired - Fee Related CN1067675C (en) | 1997-11-06 | 1997-11-06 | Oil-soluble tea polyphenol and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1067675C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1106370C (en) * | 2000-09-05 | 2003-04-23 | 四川东方绝缘材料股份有限公司 | Preparation of oil soluble tea polyphenol derivative used as edible oil antioxidant |
| US8076484B2 (en) | 2005-08-11 | 2011-12-13 | Georgia Health Science University Research Institute, Inc. | Modified green tea polyphenol formulations |
| CN102835465A (en) * | 2012-09-24 | 2012-12-26 | 合肥工业大学 | Preparation method of edible oil with tea polyphenol ester |
| US9446017B2 (en) | 2005-08-11 | 2016-09-20 | Augusta University Research Institute, Inc. | Compositions and methods for treating herpes simplex virus |
| CN112206265A (en) * | 2020-09-30 | 2021-01-12 | 华南理工大学 | Tea polyphenol modification method for improving inhibition rate of non-enzymatic glycosylation reaction and application of modified tea polyphenol |
| CN117378671A (en) * | 2023-12-12 | 2024-01-12 | 山东凯欣绿色食品股份有限公司 | Canned green tea and fruit and preparation method thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101049206B1 (en) * | 2011-01-12 | 2011-07-14 | 한국식품연구원 | Preparation method of fat-soluble tea polyphenol |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1080824A (en) * | 1993-04-13 | 1994-01-19 | 吴文 | A kind of food preservative |
-
1997
- 1997-11-06 CN CN97118872A patent/CN1067675C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1106370C (en) * | 2000-09-05 | 2003-04-23 | 四川东方绝缘材料股份有限公司 | Preparation of oil soluble tea polyphenol derivative used as edible oil antioxidant |
| US8076484B2 (en) | 2005-08-11 | 2011-12-13 | Georgia Health Science University Research Institute, Inc. | Modified green tea polyphenol formulations |
| US9446017B2 (en) | 2005-08-11 | 2016-09-20 | Augusta University Research Institute, Inc. | Compositions and methods for treating herpes simplex virus |
| CN102835465A (en) * | 2012-09-24 | 2012-12-26 | 合肥工业大学 | Preparation method of edible oil with tea polyphenol ester |
| CN112206265A (en) * | 2020-09-30 | 2021-01-12 | 华南理工大学 | Tea polyphenol modification method for improving inhibition rate of non-enzymatic glycosylation reaction and application of modified tea polyphenol |
| CN117378671A (en) * | 2023-12-12 | 2024-01-12 | 山东凯欣绿色食品股份有限公司 | Canned green tea and fruit and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1067675C (en) | 2001-06-27 |
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