HRP20180042T1 - Postupak za dobivanje ksantohumola - Google Patents
Postupak za dobivanje ksantohumola Download PDFInfo
- Publication number
- HRP20180042T1 HRP20180042T1 HRP20180042TT HRP20180042T HRP20180042T1 HR P20180042 T1 HRP20180042 T1 HR P20180042T1 HR P20180042T T HRP20180042T T HR P20180042TT HR P20180042 T HRP20180042 T HR P20180042T HR P20180042 T1 HRP20180042 T1 HR P20180042T1
- Authority
- HR
- Croatia
- Prior art keywords
- salt
- water
- xanthohumol
- mixture
- transition metal
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 16
- YKGCBLWILMDSAV-GOSISDBHSA-N Isoxanthohumol Natural products O(C)c1c2C(=O)C[C@H](c3ccc(O)cc3)Oc2c(C/C=C(\C)/C)c(O)c1 YKGCBLWILMDSAV-GOSISDBHSA-N 0.000 title claims 7
- FUSADYLVRMROPL-UHFFFAOYSA-N demethylxanthohumol Natural products CC(C)=CCC1=C(O)C=C(O)C(C(=O)C=CC=2C=CC(O)=CC=2)=C1O FUSADYLVRMROPL-UHFFFAOYSA-N 0.000 title claims 7
- ORXQGKIUCDPEAJ-YRNVUSSQSA-N xanthohumol Chemical compound COC1=CC(O)=C(CC=C(C)C)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1 ORXQGKIUCDPEAJ-YRNVUSSQSA-N 0.000 title claims 7
- UVBDKJHYMQEAQV-UHFFFAOYSA-N xanthohumol Natural products OC1=C(CC=C(C)C)C(OC)=CC(OC)=C1C(=O)C=CC1=CC=C(O)C=C1 UVBDKJHYMQEAQV-UHFFFAOYSA-N 0.000 title claims 7
- 235000008209 xanthohumol Nutrition 0.000 title claims 7
- 239000000203 mixture Substances 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 229910052723 transition metal Inorganic materials 0.000 claims 5
- -1 transition metal salt Chemical class 0.000 claims 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000000605 extraction Methods 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 235000008694 Humulus lupulus Nutrition 0.000 claims 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical class [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000003841 chloride salts Chemical class 0.000 claims 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 150000002823 nitrates Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/86—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/215—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Extraction Or Liquid Replacement (AREA)
- Medicines Containing Plant Substances (AREA)
- Compounds Of Unknown Constitution (AREA)
- Jellies, Jams, And Syrups (AREA)
Claims (15)
1. Postupak za dobivanje ksantohumola, naznačen time:
(a) da se ekstrakt koji sadrži ksantohumol miješa s vodom;
(b) da se otopina soli prijelaznog metala dodaje toj smjesi; te
(c) da se dobiveni talog sakuplja i suši.
2. Postupak prema zahtjevu 1, naznačen time da se u koraku b) koncentracija soli u smjesi postavlja na vrijednost od 0,001M do 10M.
3. Postupak prema zahtjevu 2, naznačen time da se u koraku b) koncentracija soli u smjesi postavlja na vrijednost od 0,001M do 0,05M.
4. Postupak prema bilo kojem od zahtjeva 1-3, naznačen time da se nakon dodavanja soli u koraku b:
b1) ta otopina zalužni do vrijednosti pH koja je veća od 7;
b2) da se prvi talog odfiltrira, a da se filtrat zakiseli do vrijednosti pH koja je ispod 7;
b3) da se zakiseljeni filtrat koncentrira da se dobije talog ksantohumola.
5. Postupak prema zahtjevu 4, naznačen time da se u koraku b1) otopina zalužni do pH vrijednosti od 7,5 do 10,5.
6. Postupak prema bilo kojem od zahtjeva 1-5, naznačen time da se ekstrakt koji sadrži ksantohumol dobiva ekstrakcijom iz već prethodno iskorištenog hmelja za ekstrakciju, hmelja, granulirane biljke hmelja ili smjese tih sastojaka pomiješane s organskim otapalom koje je mješljivo s vodom, gdje se spomenuto otapalo koristi u količini od 0,1 do 10 litara po 1 kg sirovinskog materijala.
7. Postupak prema zahtjevu 6, naznačen time da je korišteno organsko vodo-mješljivo otapalo odabrano od ketona i alkohola ili njihove smjese.
8. Postupak prema zahtjevu 7, naznačen time da je korišteno organsko vodo-mješljivo otapalo aceton, metanol, etanol, propanol ili njihova smjesa.
9. Postupak prema bilo kojem od zahtjeva 1-8, naznačen time da se ekstrakcija izvodi u temperaturnom opsegu od 5 do 65°C.
10. Postupak prema bilo kojem od zahtjeva 1-9, naznačen time da se ekstrakt koji sadrži ksantohumol miješa s vodom u omjeru od 0,1 do 5 litara vode na 1 litru spomenutog ekstrakta.
11. Postupak prema zahtjevu 10, naznačen time, da se ekstrakt koji sadrži ksantohumol miješa s vodom u omjeru od 1 do 3 litre vode na 1 litru spomenutog ekstrakta.
12. Postupak prema bilo kojem od zahtjeva 1-11, naznačen time da je u koraku b) koncentracija soli prijelaznih metala odabrana u opsegu od 0,01M do 0,05M.
13. Postupak prema bilo kojem od zahtjeva 1-12, naznačen time da je korištena sol prijelaznog metala upravo bakar(II) sol ili cink(II) sol.
14. Postupak prema bilo kojem od zahtjeva 1-12, naznačen time da je korištena sol prijelaznog metala kloridna sol, nitratna sol ili sulfatna sol.
15. Postupak prema bilo kojem od zahtjeva 1-14, naznačen time da je korištena sol prijelaznog metala bakar(II) klorid, bakar(II) sulfat ili cink(II) klorid ili cink(II) sulfat.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL405540A PL223580B1 (pl) | 2013-10-04 | 2013-10-04 | Sposób otrzymywania ksantohumolu o wysokiej czystości |
| EP14792560.6A EP3052466B1 (en) | 2013-10-04 | 2014-09-16 | Process for the preparation of xanthohumol |
| PCT/IB2014/001872 WO2015049561A1 (en) | 2013-10-04 | 2014-09-16 | Process for the preparation of xanthohumol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20180042T1 true HRP20180042T1 (hr) | 2018-02-09 |
Family
ID=51844768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20180042TT HRP20180042T1 (hr) | 2013-10-04 | 2018-01-09 | Postupak za dobivanje ksantohumola |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US9556097B2 (hr) |
| EP (1) | EP3052466B1 (hr) |
| JP (1) | JP6396479B2 (hr) |
| KR (1) | KR102308524B1 (hr) |
| CN (1) | CN105829275B (hr) |
| AU (1) | AU2014330867B2 (hr) |
| BR (1) | BR112016007460B1 (hr) |
| CA (1) | CA2926619C (hr) |
| CL (1) | CL2016000784A1 (hr) |
| CY (1) | CY1119888T1 (hr) |
| DK (1) | DK3052466T3 (hr) |
| ES (1) | ES2657042T3 (hr) |
| HR (1) | HRP20180042T1 (hr) |
| HU (1) | HUE037941T2 (hr) |
| IL (1) | IL244755B (hr) |
| LT (1) | LT3052466T (hr) |
| ME (1) | ME02981B (hr) |
| MX (1) | MX362188B (hr) |
| PL (1) | PL223580B1 (hr) |
| PT (1) | PT3052466T (hr) |
| RS (1) | RS56756B1 (hr) |
| RU (1) | RU2655926C2 (hr) |
| SI (1) | SI3052466T1 (hr) |
| UA (1) | UA116913C2 (hr) |
| WO (1) | WO2015049561A1 (hr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL242648B1 (pl) * | 2017-06-30 | 2023-04-03 | Bioactive Tech Spolka Z Ograniczona Odpowiedzialnoscia | Sposób otrzymywania ksantohumolu |
| US11026897B2 (en) | 2018-08-10 | 2021-06-08 | Metagenics, Inc. | Composition of curcumagalactomannoside and hops extract |
| EP4104818A1 (en) | 2021-06-17 | 2022-12-21 | Skeye Pharma GbR | Ophthalmic composition comprising xanthohumol |
| EP4104817A1 (en) | 2021-06-17 | 2022-12-21 | Skeye Pharma GbR | Ophthalmic composition comprising astragaloside iv |
| EP4302767B1 (en) | 2022-07-04 | 2024-10-02 | Skeye Pharma GmbH | Ophthalmic composition comprising eriocitrin for treating dry eye syndrome |
| PL441690A1 (pl) * | 2022-07-08 | 2024-01-15 | Innox Spółka Z Ograniczoną Odpowiedzialnością | Sposób izolacji i oczyszczania ksantohumolu |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1274678A (en) | 1968-11-19 | 1972-05-17 | Bush Boake Allen Ltd | Hop extracts |
| CN1260122A (zh) * | 1999-01-08 | 2000-07-19 | 仲伟德 | 一种以植物为原料的杀菌剂农药 |
| DE19939350B4 (de) | 1999-08-19 | 2005-04-07 | Plantextrakt Gmbh & Co. Kg | Hopfenextrakt und Verfahren zu dessen Herstellung |
| DE10139479A1 (de) | 2001-08-10 | 2003-02-27 | Schwabe Willmar Gmbh & Co | Hopfenextrakte, Verfahren zu ihrer Herstellung und Verwendung |
| DE10256031A1 (de) | 2002-11-30 | 2004-06-09 | Nateco 2 Gmbh & Co. Kg | Verfahren zur Herstellung eines Xanthohumol-angereicherten Hopfenextraktes und dessen Verwendung |
| EP1543834A1 (en) | 2003-12-16 | 2005-06-22 | Biodynamics | Production of hop extracts having oestrogenic and antiproliferative bioactivity |
| DE102006018988B3 (de) * | 2006-04-25 | 2007-08-09 | Nateco2 Gmbh & Co. Kg | Verfahren zur Herstellung eines Xanthohumol-haltigen Pulvers hoher Reinheit und dessen Verwendung |
| RU2344167C2 (ru) * | 2007-03-12 | 2009-01-20 | Общество с ограниченной ответственностью "Дары Кубани" | Хмелевый экстракт |
| US7833552B2 (en) * | 2007-08-15 | 2010-11-16 | Flaxan Gmbh & Co. Kg | Xanthohumol-enriched hop extract |
| US8142821B2 (en) | 2007-08-15 | 2012-03-27 | Flazan GmbH & Co. KG | Xanthohumol-enriched hop extract |
| CN101440029A (zh) | 2008-11-04 | 2009-05-27 | 中国食品发酵工业研究院 | 一种从啤酒花中提取黄腐酚的方法 |
| CN101433592B (zh) | 2008-12-12 | 2011-06-08 | 桂林莱茵生物科技股份有限公司 | 含黄腐酚的啤酒花提取物的制备方法 |
| PL214468B1 (pl) | 2009-05-15 | 2013-08-30 | Univ Przyrodniczy We Wroclawiu | Sposób otrzymywania ksantohumolu |
| CN101811950B (zh) | 2010-05-07 | 2013-01-30 | 玉门拓璞科技开发有限责任公司 | 高纯度黄腐酚的工业化生产方法 |
-
2013
- 2013-10-04 PL PL405540A patent/PL223580B1/pl unknown
-
2014
- 2014-09-16 DK DK14792560.6T patent/DK3052466T3/en active
- 2014-09-16 US US15/027,004 patent/US9556097B2/en active Active
- 2014-09-16 MX MX2016004128A patent/MX362188B/es active IP Right Grant
- 2014-09-16 CA CA2926619A patent/CA2926619C/en active Active
- 2014-09-16 LT LTEP14792560.6T patent/LT3052466T/lt unknown
- 2014-09-16 CN CN201480054359.5A patent/CN105829275B/zh active Active
- 2014-09-16 BR BR112016007460-2A patent/BR112016007460B1/pt active IP Right Grant
- 2014-09-16 KR KR1020167010538A patent/KR102308524B1/ko active IP Right Grant
- 2014-09-16 AU AU2014330867A patent/AU2014330867B2/en active Active
- 2014-09-16 EP EP14792560.6A patent/EP3052466B1/en active Active
- 2014-09-16 UA UAA201604939A patent/UA116913C2/uk unknown
- 2014-09-16 ES ES14792560.6T patent/ES2657042T3/es active Active
- 2014-09-16 HU HUE14792560A patent/HUE037941T2/hu unknown
- 2014-09-16 RU RU2016115081A patent/RU2655926C2/ru active
- 2014-09-16 WO PCT/IB2014/001872 patent/WO2015049561A1/en active Application Filing
- 2014-09-16 ME MEP-2018-11A patent/ME02981B/me unknown
- 2014-09-16 JP JP2016546186A patent/JP6396479B2/ja active Active
- 2014-09-16 RS RS20180034A patent/RS56756B1/sr unknown
- 2014-09-16 SI SI201430570T patent/SI3052466T1/en unknown
- 2014-09-16 PT PT147925606T patent/PT3052466T/pt unknown
-
2016
- 2016-03-27 IL IL24475516A patent/IL244755B/en active IP Right Grant
- 2016-04-04 CL CL2016000784A patent/CL2016000784A1/es unknown
-
2018
- 2018-01-09 HR HRP20180042TT patent/HRP20180042T1/hr unknown
- 2018-01-22 CY CY20181100075T patent/CY1119888T1/el unknown
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