IL24764A - Method of producing hydroxy-flavan 3,4-diols - Google Patents
Method of producing hydroxy-flavan 3,4-diolsInfo
- Publication number
- IL24764A IL24764A IL24764A IL2476465A IL24764A IL 24764 A IL24764 A IL 24764A IL 24764 A IL24764 A IL 24764A IL 2476465 A IL2476465 A IL 2476465A IL 24764 A IL24764 A IL 24764A
- Authority
- IL
- Israel
- Prior art keywords
- solution
- hydroxyflavan
- aqueous solution
- ethyl acetate
- vegetable material
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- JYAAVRVRJWAIQQ-UHFFFAOYSA-N 2-phenyl-3,4-dihydrochromene-2,3,4-triol Chemical class O1C2=CC=CC=C2C(O)C(O)C1(O)C1=CC=CC=C1 JYAAVRVRJWAIQQ-UHFFFAOYSA-N 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- JGDWYKQLFQQIDH-UHFFFAOYSA-N 2-phenyl-3,4-dihydrochromen-2-ol Chemical compound C1CC2=CC=CC=C2OC1(O)C1=CC=CC=C1 JGDWYKQLFQQIDH-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 235000003276 Apios tuberosa Nutrition 0.000 claims description 2
- 244000105624 Arachis hypogaea Species 0.000 claims description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
- 235000010744 Arachis villosulicarpa Nutrition 0.000 claims description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 claims description 2
- 241000018646 Pinus brutia Species 0.000 claims description 2
- 235000011613 Pinus brutia Nutrition 0.000 claims description 2
- QOLIPNRNLBQTAU-UHFFFAOYSA-N flavan Chemical compound C1CC2=CC=CC=C2OC1C1=CC=CC=C1 QOLIPNRNLBQTAU-UHFFFAOYSA-N 0.000 claims description 2
- 229920001864 tannin Polymers 0.000 claims description 2
- 235000018553 tannin Nutrition 0.000 claims description 2
- 239000001648 tannin Substances 0.000 claims description 2
- 239000005418 vegetable material Substances 0.000 claims 8
- 238000001704 evaporation Methods 0.000 claims 2
- 230000008020 evaporation Effects 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000013329 compounding Methods 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000008569 process Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229940093797 bioflavonoids Drugs 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 description 1
- 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 1
- 241000700198 Cavia Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 229920000473 Phlobaphene Polymers 0.000 description 1
- 241001236212 Pinus pinaster Species 0.000 description 1
- 235000005105 Pinus pinaster Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 1
- 235000012734 epicatechin Nutrition 0.000 description 1
- -1 ethyl ion Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/13—Coniferophyta (gymnosperms)
- A61K36/15—Pinaceae (Pine family), e.g. pine or cedar
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61J—CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE
- A61J1/00—Containers specially adapted for medical or pharmaceutical purposes
- A61J1/05—Containers specially adapted for medical or pharmaceutical purposes for collecting, storing or administering blood, plasma or medical fluids ; Infusion or perfusion containers
- A61J1/10—Bag-type containers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M5/00—Devices for bringing media into the body in a subcutaneous, intra-vascular or intramuscular way; Accessories therefor, e.g. filling or cleaning devices, arm-rests
- A61M5/14—Infusion devices, e.g. infusing by gravity; Blood infusion; Accessories therefor
-
- 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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Alternative & Traditional Medicine (AREA)
- Biomedical Technology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Anesthesiology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR998508A FR1427100A (fr) | 1964-12-14 | 1964-12-14 | Procédé pour l'obtention d'hydroxyflavanne-3-4-diols |
| FR9054 | 1965-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL24764A true IL24764A (en) | 1970-06-17 |
Family
ID=26162367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL24764A IL24764A (en) | 1964-12-14 | 1965-12-10 | Method of producing hydroxy-flavan 3,4-diols |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3436407A (fr) |
| FR (2) | FR1427100A (fr) |
| GB (1) | GB1092269A (fr) |
| IL (1) | IL24764A (fr) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2092743A1 (en) * | 1970-06-15 | 1972-01-28 | Aquitaine Invest Pharma | Complete extraction of total flavanol gomers from plats -peripheral - venous activity |
| US4510115A (en) * | 1982-11-03 | 1985-04-09 | Baxter Travenol Laboratories, Inc. | Method for forming layered thermoplastic articles |
| US4698360B1 (en) * | 1985-04-09 | 1997-11-04 | D Investigations Pharmacologiq | Plant extract with a proanthocyanidins content as therapeutic agent having radical scavenger effect and use thereof |
| FR2643073B1 (fr) * | 1989-02-15 | 1991-08-16 | Expansion Rech Phytochimie | Procede de preparation d'extraits polyphenoliques de type flavane-3-ol purifies et extraits obtenus |
| FR2722498B1 (fr) | 1994-07-12 | 1996-10-11 | Berkem Sa | Procede de preparation d'extraits contenant des composes polyphenoliques oligomeres de type catechique a partir de xources vegetales et extraits obtenus |
| FR2725447B1 (fr) | 1994-10-11 | 1996-12-27 | Sanofi Sa | Procede d'obtention d'oligomeres procyanidoliques |
| FR2734478B1 (fr) * | 1995-05-23 | 1997-07-11 | Berkem Sa | Composition cosmetique ou pharmaceutique utilisable par voie topique ou orale ayant des proprietes antiradicalaires et un pouvoir filtrant vis-a-vis des uv |
| US5719178A (en) * | 1995-11-20 | 1998-02-17 | Paul; Julie Chasen | Methods and compositions for treating attention-deficit/hyperactivity disorder |
| JPH09175982A (ja) * | 1995-12-28 | 1997-07-08 | Nikka Uisukii Kk | 化粧品 |
| FR2749303B1 (fr) * | 1996-05-30 | 1998-08-07 | Berkem Sa | Procede d'extraction de polyphenols catechiques a partir de potentilles extrait obtenu et son utilisation |
| US6569446B1 (en) | 1996-09-20 | 2003-05-27 | The Howard Foundation | Solubilization of flavonols |
| US6238673B1 (en) | 1996-09-20 | 2001-05-29 | The Howard Foundation | Method of producing high flavonol content polyphenol compositions |
| GB2317561B (en) * | 1996-09-20 | 2000-12-06 | Howard Foundation | Improvements in or relating to food supplements |
| AU4310697A (en) * | 1996-09-20 | 1998-04-14 | Howard Foundation, The | Method of producing polyphenol-containing compositions |
| US5817299A (en) * | 1996-11-01 | 1998-10-06 | E-L Management Corp. | Non-chemical sunscreen composition |
| US6544581B1 (en) | 1999-06-22 | 2003-04-08 | Canandaigua Wine Company, Inc. | Process for extraction, purification and enrichment of polyphenolic substances from whole grapes, grape seeds and grape pomace |
| WO2001011988A2 (fr) * | 1999-08-13 | 2001-02-22 | Dry Creek Nutrition, Inc. | Nouvelles compositions polymeres polyphenoliques, isolement de ces compositions, et modification et amelioration des qualites organoleptiques de produits comestibles |
| FR2822466B1 (fr) | 2001-03-23 | 2004-07-02 | Diana Ingredients | Fraction phenolique riche en phloridzine et son utilisation en tant qu'agent cosmetique, alimentaire ou nutraceutique |
| FR2836336B1 (fr) | 2002-02-26 | 2004-08-27 | Diana Ingredients | Utilisation dans un traitement cosmetique d'une fraction phenolique riche en dihydrochalcones |
| WO2005070443A1 (fr) * | 2004-01-21 | 2005-08-04 | Toyo Shinyaku Co., Ltd. | Extrait d'écorce d'arbre |
| WO2006113700A1 (fr) * | 2005-04-16 | 2006-10-26 | Unitel Technologies, Inc. | Produit polyphenolique concentre et procede de fabrication correspondant |
| JP2007306872A (ja) * | 2006-05-19 | 2007-11-29 | Suntory Ltd | プロアントシアニジン含有茶飲料 |
| US9084434B2 (en) | 2006-09-27 | 2015-07-21 | Little Calumet Holdings Llc | Probiotic oral dosage forms |
| US8114445B2 (en) * | 2008-11-07 | 2012-02-14 | Reliv International Inc. | Dietary supplement for promoting wellness and weight loss and methods of administering the same |
| CN102573834B (zh) | 2009-08-12 | 2015-04-29 | 贺发研究Ip(Pyc)公司 | 用于治疗动脉粥样硬化等心血管功能失调疾病的如碧萝芷或葡萄籽的原花色甙元和积雪草的复合制剂 |
| WO2011161655A1 (fr) | 2010-06-25 | 2011-12-29 | Horphag Research (Ip) Pre Ltd | Composition destinée à améliorer le bien-être sexuel |
| CN108299371A (zh) * | 2018-05-07 | 2018-07-20 | 黑龙江中医药大学 | 一种从蓝莓叶提取原花青素的方法 |
| AU2021291337A1 (en) | 2020-06-18 | 2023-01-05 | Horphag Research Ip (Pyc) Ltd. | Procyanidins for the treatment of endothelial dysfunction triggered by COVID-19 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744919A (en) * | 1952-09-09 | 1956-05-08 | Ervin F Kurth | Producing pure dihydroquercetin |
| US2870165A (en) * | 1956-06-20 | 1959-01-20 | Rayonier Inc | Process for recovering flavonoids from bark |
| US3131198A (en) * | 1961-07-24 | 1964-04-28 | Weyerhaeuser Co | Processing of aqueous extracts of bark |
| US3266903A (en) * | 1963-01-25 | 1966-08-16 | Jurd Leonard | Methods of using flavylium compounds for food coloring |
-
1964
- 1964-12-14 FR FR998508A patent/FR1427100A/fr not_active Expired
-
1965
- 1965-03-12 FR FR954A patent/FR1419521A/fr not_active Expired
- 1965-12-03 GB GB51398/65A patent/GB1092269A/en not_active Expired
- 1965-12-10 US US513118A patent/US3436407A/en not_active Expired - Lifetime
- 1965-12-10 IL IL24764A patent/IL24764A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3436407A (en) | 1969-04-01 |
| FR1427100A (fr) | 1966-02-04 |
| FR4482M (fr) | 1966-10-03 |
| FR1419521A (fr) | 1965-11-26 |
| GB1092269A (en) | 1967-11-22 |
| DE1492155A1 (de) | 1969-12-18 |
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