CN1166661C - 制备表棓儿茶素没食子酸酯的方法 - Google Patents
制备表棓儿茶素没食子酸酯的方法 Download PDFInfo
- Publication number
- CN1166661C CN1166661C CNB001226940A CN00122694A CN1166661C CN 1166661 C CN1166661 C CN 1166661C CN B001226940 A CNB001226940 A CN B001226940A CN 00122694 A CN00122694 A CN 00122694A CN 1166661 C CN1166661 C CN 1166661C
- Authority
- CN
- China
- Prior art keywords
- egcg
- water
- mixture
- volume
- catechin
- 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.)
- Expired - Lifetime
Links
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 title claims abstract description 130
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 title claims abstract description 129
- 229940030275 epigallocatechin gallate Drugs 0.000 title claims abstract description 126
- 238000004519 manufacturing process Methods 0.000 title description 3
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims abstract description 69
- 235000005487 catechin Nutrition 0.000 claims abstract description 69
- 239000011347 resin Substances 0.000 claims abstract description 41
- 229920005989 resin Polymers 0.000 claims abstract description 40
- 229940094952 green tea extract Drugs 0.000 claims abstract description 31
- 235000020688 green tea extract Nutrition 0.000 claims abstract description 31
- 230000001172 regenerating effect Effects 0.000 claims abstract description 14
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 68
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims description 67
- 229950001002 cianidanol Drugs 0.000 claims description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 23
- 239000003960 organic solvent Substances 0.000 claims description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 17
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 229920001429 chelating resin Polymers 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- 229920000571 Nylon 11 Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 235000006226 Areca catechu Nutrition 0.000 claims description 2
- 239000004760 aramid Substances 0.000 claims description 2
- 229920003235 aromatic polyamide Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 244000080767 Areca catechu Species 0.000 claims 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001765 catechin Chemical class 0.000 abstract description 4
- 239000012156 elution solvent Substances 0.000 abstract 1
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 68
- 238000004128 high performance liquid chromatography Methods 0.000 description 42
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 36
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 34
- 229960001948 caffeine Drugs 0.000 description 34
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 34
- 239000002994 raw material Substances 0.000 description 33
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 18
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 description 18
- 229940074391 gallic acid Drugs 0.000 description 18
- 235000004515 gallic acid Nutrition 0.000 description 18
- 229940092665 tea leaf extract Drugs 0.000 description 18
- 244000269722 Thea sinensis Species 0.000 description 14
- 230000000694 effects Effects 0.000 description 12
- 150000008442 polyphenolic compounds Chemical class 0.000 description 12
- 235000013824 polyphenols Nutrition 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- 238000007872 degassing Methods 0.000 description 9
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 235000013305 food Nutrition 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 6
- 235000009569 green tea Nutrition 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000000935 solvent evaporation Methods 0.000 description 6
- 235000013616 tea Nutrition 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000011552 falling film Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229930014124 (-)-epigallocatechin gallate Natural products 0.000 description 3
- 235000004911 (-)-epigallocatechin gallate Nutrition 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- VFSWRBJYBQXUTE-UHFFFAOYSA-N epi-Gallocatechin 3-O-gallate Natural products Oc1ccc2C(=O)C(OC(=O)c3cc(O)c(O)c(O)c3)C(Oc2c1)c4cc(O)c(O)c(O)c4 VFSWRBJYBQXUTE-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000003627 anti-cholesterol Effects 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 230000002790 anti-mutagenic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000006200 vaporizer Substances 0.000 description 2
- GDSOZVZXVXTJMI-SNAWJCMRSA-N (e)-1-methylbut-1-ene-1,2,4-tricarboxylic acid Chemical compound OC(=O)C(/C)=C(C(O)=O)\CCC(O)=O GDSOZVZXVXTJMI-SNAWJCMRSA-N 0.000 description 1
- 244000235603 Acacia catechu Species 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 241000208199 Buxus sempervirens Species 0.000 description 1
- 101150096839 Fcmr gene Proteins 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 229920003692 Grilamid® L Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 235000006468 Thea sinensis Nutrition 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F3/00—Tea; Tea substitutes; Preparations thereof
- A23F3/16—Tea extraction; Tea extracts; Treating tea extract; Making instant tea
- A23F3/20—Removing unwanted substances
- A23F3/205—Using flocculating or adsorbing agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pyrane Compounds (AREA)
- Tea And Coffee (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99116032 | 1999-08-16 | ||
| EP99116032.6 | 1999-08-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1286252A CN1286252A (zh) | 2001-03-07 |
| CN1166661C true CN1166661C (zh) | 2004-09-15 |
Family
ID=8238779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB001226940A Expired - Lifetime CN1166661C (zh) | 1999-08-16 | 2000-08-16 | 制备表棓儿茶素没食子酸酯的方法 |
Country Status (11)
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2275463T3 (es) * | 1999-08-16 | 2007-06-16 | Dsm Ip Assets B.V. | Proceso para la produccion de galato de epigalocatequina. |
| KR20030010011A (ko) * | 2001-07-25 | 2003-02-05 | (주)엔바이오솔루션 | 녹차로부터 얻어진 에피갈로카테킨 갈레이트의 추출방법 |
| KR100497003B1 (ko) * | 2002-08-30 | 2005-06-23 | 주식회사 바이오랜드 | 안구표면 질환 치료용 양막을 보존하기 위한 양막보존액 조성물 |
| US20050008712A1 (en) * | 2003-07-08 | 2005-01-13 | Debasis Bagchi | Compositions incorporating high-caffeine green tea extract and related methods for promoting healthy body weight |
| KR20060121866A (ko) | 2003-09-09 | 2006-11-29 | 디에스엠 아이피 어셋츠 비.브이. | 산화에 민감한 물질 하나 이상을 함유하는 경구 활성을갖는 본질적으로 무수성의 국소 작용제 |
| US7303773B2 (en) | 2003-10-21 | 2007-12-04 | The Procter & Gamble Company | Process for enriching extracts of natural theanine |
| EP1690457B1 (en) * | 2003-12-02 | 2010-08-11 | Kao Corporation | Package drink |
| US7935478B2 (en) * | 2004-02-02 | 2011-05-03 | Core Dynamics Limited | Biological material and methods and solutions for preservation thereof |
| EP1781116A4 (en) * | 2004-06-04 | 2009-07-29 | Horizon Science Pty Ltd | NATURAL SWEETENER |
| US8021697B2 (en) * | 2005-06-03 | 2011-09-20 | Horizon Science Pty. Ltd. | Substances having body mass redistribution properties |
| JP2008545766A (ja) * | 2005-06-07 | 2008-12-18 | ディーエスエム アイピー アセッツ ビー．ブイ． | （−）−エピガロカテキンガレートの新規使用 |
| KR100659138B1 (ko) | 2005-09-16 | 2006-12-19 | (주)아모레퍼시픽 | 유효성분으로 갈로카테킨 갈레이트를 함유하는 보습용피부외용제 조성물 |
| DE102005056652A1 (de) * | 2005-11-25 | 2007-05-31 | Südzucker AG Mannheim/Ochsenfurt | Präparat enthaltend eine polyphenolhaltige Zusammensetzung und Isomaltulose |
| JP4807563B2 (ja) | 2005-12-06 | 2011-11-02 | 株式会社 伊藤園 | 容器詰め飲料及びその製造方法 |
| ES2280141B1 (es) * | 2006-02-27 | 2008-10-01 | Natraceutical, S.A. | "proceso para la obtencion de polvo de cacao rico en polifenoles y bajo contenido en materia grasa y polvo de cacao obtenido". |
| US9808023B2 (en) | 2006-03-02 | 2017-11-07 | Kao Corporation | Process for producing purified tea extract |
| AU2007299581B2 (en) * | 2006-09-19 | 2011-04-28 | Poly Gain Pte Ltd | Extracts derived from sugar cane and a process for their manufacture |
| US8518458B2 (en) | 2006-09-21 | 2013-08-27 | Immune Guard, LLC | Tea-derived compositions and methods of using same for cardiovascular health |
| US8465782B2 (en) | 2006-09-21 | 2013-06-18 | Immune Guard, LLC | Methods and materials for reducing risk of cold and/or flu |
| CN101134941B (zh) * | 2007-07-27 | 2013-03-06 | 东华大学 | 米曲霉高效制备egcg水解酶及生产egc和没食子酸的方法 |
| JP4866815B2 (ja) * | 2007-09-05 | 2012-02-01 | 花王株式会社 | 精製緑茶抽出物の製造法 |
| CN101492440B (zh) * | 2008-01-24 | 2012-10-03 | 上海新康制药厂 | 茶多酚中主要儿茶素成分分离纯化方法及其糖苷酶活性 |
| EP2263332A2 (en) * | 2008-03-12 | 2010-12-22 | Hypres Inc. | Digital radio-frequency tranceiver system and method |
| JP5307649B2 (ja) * | 2009-02-20 | 2013-10-02 | 花王株式会社 | 精製茶抽出物の製造方法 |
| TR200907338A1 (tr) * | 2009-09-28 | 2011-04-21 | Yedi̇tepe Üni̇versi̇tesi̇ | Doğal bileşenler içeren bir film şeridi. |
| CN101703130B (zh) * | 2009-12-03 | 2012-05-02 | 应维强 | 绿茶提取物的生产工艺 |
| JP5858697B2 (ja) * | 2010-12-15 | 2016-02-10 | オルガノ株式会社 | ガレート型カテキンの精製方法及び精製装置 |
| CN102558129B (zh) * | 2010-12-15 | 2015-02-18 | 奥加诺株式会社 | 没食子酸酯型儿茶素的提纯方法以及提纯装置 |
| US9572852B2 (en) | 2011-02-08 | 2017-02-21 | The Product Makers (Australia) Pty Ltd | Sugar extracts |
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| CN106168608A (zh) * | 2016-08-25 | 2016-11-30 | 江苏天晟药业股份有限公司 | 一种茶多酚中egcg含量的检测方法 |
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- 2000-08-11 ES ES00117410T patent/ES2275463T3/es not_active Expired - Lifetime
- 2000-08-11 EP EP06024103A patent/EP1767097A3/en not_active Ceased
- 2000-08-11 DE DE60031921T patent/DE60031921T2/de not_active Expired - Lifetime
- 2000-08-11 EP EP00117410A patent/EP1077211B1/en not_active Expired - Lifetime
- 2000-08-11 AT AT00117410T patent/ATE346059T1/de not_active IP Right Cessation
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- 2005-11-09 US US11/272,122 patent/US7312199B2/en not_active Expired - Lifetime
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| DE60031921T2 (de) | 2007-09-20 |
| JP2001097968A (ja) | 2001-04-10 |
| CA2315886A1 (en) | 2001-02-16 |
| BR0003578A (pt) | 2002-06-18 |
| US20030083270A1 (en) | 2003-05-01 |
| US20060069046A1 (en) | 2006-03-30 |
| CA2315886C (en) | 2010-05-25 |
| BR0003578B1 (pt) | 2014-04-08 |
| BRPI0003578C1 (pt) | 2021-05-25 |
| EP1077211B1 (en) | 2006-11-22 |
| CN1286252A (zh) | 2001-03-07 |
| EP1767097A2 (en) | 2007-03-28 |
| ATE346059T1 (de) | 2006-12-15 |
| US7012149B2 (en) | 2006-03-14 |
| EP1767097A3 (en) | 2007-04-04 |
| IN190860B (US07585860-20090908-C00112.png) | 2003-08-30 |
| KR20010050080A (ko) | 2001-06-15 |
| KR100847171B1 (ko) | 2008-07-17 |
| BRPI0003578B8 (pt) | 2016-05-10 |
| US7312199B2 (en) | 2007-12-25 |
| KR20080059115A (ko) | 2008-06-26 |
| JP4643808B2 (ja) | 2011-03-02 |
| EP1077211A3 (en) | 2001-03-28 |
| DE60031921D1 (de) | 2007-01-04 |
| ES2275463T3 (es) | 2007-06-16 |
| EP1077211A2 (en) | 2001-02-21 |
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