HRP20211363T1 - Priprema kiselina hmelja i njihovih derivata - Google Patents
Priprema kiselina hmelja i njihovih derivata Download PDFInfo
- Publication number
- HRP20211363T1 HRP20211363T1 HRP20211363TT HRP20211363T HRP20211363T1 HR P20211363 T1 HRP20211363 T1 HR P20211363T1 HR P20211363T T HRP20211363T T HR P20211363TT HR P20211363 T HRP20211363 T HR P20211363T HR P20211363 T1 HRP20211363 T1 HR P20211363T1
- Authority
- HR
- Croatia
- Prior art keywords
- tetrahydro
- acid
- iso
- cis
- acids
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims 13
- 150000007513 acids Chemical class 0.000 title claims 2
- 238000000034 method Methods 0.000 claims 7
- QRDZSRWEULKVNW-UHFFFAOYSA-N 6-hydroxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical compound C1=C(O)C=C2C(C(=O)O)=CC(=O)NC2=C1 QRDZSRWEULKVNW-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 238000006317 isomerization reaction Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- JIZQRWKUYFNSDM-BTYIYWSLSA-N (4r,5r)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one Chemical compound CC(C)CC[C@H]1C(=O)C(C(=O)CC(C)C)=C(O)[C@@]1(O)C(=O)CCC(C)C JIZQRWKUYFNSDM-BTYIYWSLSA-N 0.000 claims 1
- JIZQRWKUYFNSDM-VFNWGFHPSA-N (4r,5s)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one Chemical compound CC(C)CC[C@@H]1C(=O)C(C(=O)CC(C)C)=C(O)[C@@]1(O)C(=O)CCC(C)C JIZQRWKUYFNSDM-VFNWGFHPSA-N 0.000 claims 1
- WTOFWQARBRVYHI-UHFFFAOYSA-N 3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbutyl)cyclohexa-2,4-dien-1-one Chemical compound CC(C)CCC1=C(O)C(O)(CCC(C)C)C(=O)C(C(=O)CC(C)C)=C1O WTOFWQARBRVYHI-UHFFFAOYSA-N 0.000 claims 1
- GEXOPZHAKQAGLU-UHFFFAOYSA-N Colupulone Natural products CC(C)C(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O GEXOPZHAKQAGLU-UHFFFAOYSA-N 0.000 claims 1
- UNCDMWKTFLUPHZ-UHFFFAOYSA-N colupulone Chemical compound CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O UNCDMWKTFLUPHZ-UHFFFAOYSA-N 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/713—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C3/00—Treatment of hops
- C12C3/12—Isomerised products from hops
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C5/00—Other raw materials for the preparation of beer
- C12C5/02—Additives for beer
- C12C5/026—Beer flavouring preparations
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Food Science & Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Seasonings (AREA)
Claims (7)
1. Postupak za pripremu mješavine hmeljne kiseline, koji obuhvaća:
dovođenje u vezu racemata tetrahidro-α-kiselina s kiralnim aminom kako bi nastao kompleks kiseline hmelja kao talog ili u otopini, pri čemu kompleks kiseline hmelja ima enantiomerni višak (+)-tetrahidro-α-kiselina, gdje je amin (1S, 2R)-(-)-cis-1-amino-indanol.
2. Postupak prema zahtjevu 1, naznačen time što dalje sadrži:
tretiranje kompleksa hmeljne kiseline za pripravu krutine koja ima enantiomerni višak (+)-tetrahidro-α-kiselina veći od 50%.
3. Postupak prema zahtjevu 1, naznačen time što dalje sadrži:
tretiranje kompleksa hmeljne kiseline za pripravu krutine koja ima enantiomerni višak (+)-tetrahidro-α-kiselina veći od 80%.
4. Postupak prema zahtjevu 1, naznačen time što:
racemat tetrahidro-α-kiseline pripravljen je hidrogeniranjem β-kiseline za pripremu desoksi-α-kiseline, te oksidacijom i izomerizacijom hidrogenirane desoksi-α-kiseline za pripremu racemata tetrahidro-α-kiseline, β-kiselina je kolupulon, a desoksi-α-kiselina je tetrahidrodezoksikohumulon.
5. Postupak prema zahtjevu 1, naznačen time što:
tetrahidro-α-kiselina se bira između tetrahidrohumulona, tetrahidrokohumulona i tetrahidroadhumulona.
6. Postupak prema zahtjevu 1, naznačen time što dalje sadrži:
izomeriziranje (+)-tetrahidro-α-kiselina u hmeljne kiseline odabrane iz skupine koju čine (+)-trans-tetrahidro-izo-α-kiseline, (-)-cis-tetrahidro-izo-α-kiseline i smjese toga.
7. Postupak prema zahtjevu 6, naznačen time što:
(+)-trans-tetrahidro-izo-α-kiselina je odabrana od (+)-trans-tetrahidro-izo-humulona, (+)-trans-tetrahidro-izo-kohumulona i (+)-trans-tetrahidro-izo-adhumulona, a (-)-cis-tetrahidro-izo-α-kiselina je odabrana od (-)-cis-tetrahidro-izo-humulona, (-)-cis-tetrahidro-izo-kohumulona i (-) -cis-tetrahidro-izo-adhumulona.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34720110P | 2010-05-21 | 2010-05-21 | |
| PCT/US2011/037398 WO2011146873A1 (en) | 2010-05-21 | 2011-05-20 | Preparation of hop acids and their derivatives |
| EP11726002.6A EP2571974B1 (en) | 2010-05-21 | 2011-05-20 | Preparation of hop acids and their derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20211363T1 true HRP20211363T1 (hr) | 2021-12-24 |
Family
ID=44279020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20211363TT HRP20211363T1 (hr) | 2010-05-21 | 2011-05-20 | Priprema kiselina hmelja i njihovih derivata |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8871978B2 (hr) |
| EP (1) | EP2571974B1 (hr) |
| JP (1) | JP5888705B2 (hr) |
| CN (1) | CN102906243B (hr) |
| ES (1) | ES2886057T3 (hr) |
| HK (1) | HK1178562A1 (hr) |
| HR (1) | HRP20211363T1 (hr) |
| HU (1) | HUE055712T2 (hr) |
| RS (1) | RS62335B1 (hr) |
| WO (1) | WO2011146873A1 (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201402484QA (en) * | 2011-11-22 | 2014-09-26 | Suntory Holdings Ltd | Non-alcohol, beer-taste beverage having substantiality in taste |
| AU2012324005B2 (en) * | 2011-11-22 | 2015-10-22 | Suntory Holdings Limited | Low extract component, beer-taste beverage having adjusted pH |
| CA2855649C (en) * | 2011-11-22 | 2017-04-25 | Suntory Holdings Limited | Non-alcohol beer-taste beverage |
| EP2865744B1 (en) * | 2012-06-20 | 2024-07-31 | Kirin Holdings Kabushiki Kaisha | Beverage containing aqueous medium extract of hops used in oxidation |
| RU2015111684A (ru) | 2012-12-28 | 2017-02-02 | Сантори Холдингз Лимитед | Безалкогольный напиток со вкусом пива, имеющий shimari во вкусе |
| GB201318568D0 (en) | 2013-10-21 | 2013-12-04 | Ifast Nv | Method for extraction and dissolution of hop acids in aqueous media |
| US12098120B2 (en) * | 2021-08-18 | 2024-09-24 | P2 Science, Inc. | Humulus species as industrial chemical feedstocks |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1618059B1 (de) | 1967-05-02 | 1971-07-15 | Atlantic Res Inst Ltd | Verfahren zur Herstellung von Isohumulon |
| GB1266716A (hr) * | 1969-09-26 | 1972-03-15 | ||
| JPS4916128B1 (hr) * | 1970-09-28 | 1974-04-19 | ||
| US3923897A (en) | 1973-04-02 | 1975-12-02 | Kalamazoo Spice Extract Co | Production of hoplike beverage bittering materials |
| US4644084A (en) * | 1984-01-25 | 1987-02-17 | Miller Brewing Company | Preparation of tetrahydroisohumulones |
| US5013571A (en) * | 1990-01-31 | 1991-05-07 | Pfizer Inc. | Methods for making tetrahydroisoalpha and hexahydroisoalpha acids |
| US5523489A (en) | 1995-02-07 | 1996-06-04 | Miller Brewing Company | Preparation of tetrahydroisohumulones |
| US5677469A (en) * | 1995-05-18 | 1997-10-14 | Sepracor, Inc. | Process for resolving chiral acids with 1-aminoindan-2-ols |
| US6020019A (en) | 1996-03-26 | 2000-02-01 | Miller Brewing Company | Hydrogenation of hop soft resins using CO2 |
| US5767319A (en) | 1996-10-30 | 1998-06-16 | Miller Brewing Company | Preparation of tetrahydroiso-α-acids by the hydrogenation of the metal salts of iso-α-acids |
| US6303824B1 (en) | 1999-11-11 | 2001-10-16 | Miller Brewing Company | Method of hydrogenating iso-α acids in a buffered solution |
| JP2004500349A (ja) * | 1999-11-18 | 2004-01-08 | エス・エス・シュタイナー・インコーポレーテッド | ホップ樹脂酸の水素化方法 |
| US7388098B2 (en) | 2000-09-29 | 2008-06-17 | Bristol-Myers Squibb Company | Dynamic resolution of isomers and resolved isomers |
| US7270835B2 (en) | 2001-06-20 | 2007-09-18 | Metaproteomics, Llc | Compositions that treat or inhibit pathological conditions associated with inflammatory response |
| ATE522207T1 (de) * | 2002-02-14 | 2011-09-15 | Kirin Brewery | Zusammensetzungen und nahrungsmittel zur verbesserung des fettstoffwechsels |
| EP2147910A1 (en) | 2008-07-15 | 2010-01-27 | Pronova BioPharma Norge AS | Novel lipid compounds |
| JP5580543B2 (ja) * | 2009-03-11 | 2014-08-27 | サッポロビール株式会社 | 心理状態改善剤 |
-
2011
- 2011-05-20 US US13/112,770 patent/US8871978B2/en active Active
- 2011-05-20 HU HUE11726002A patent/HUE055712T2/hu unknown
- 2011-05-20 EP EP11726002.6A patent/EP2571974B1/en active Active
- 2011-05-20 ES ES11726002T patent/ES2886057T3/es active Active
- 2011-05-20 CN CN201180025040.6A patent/CN102906243B/zh active Active
- 2011-05-20 WO PCT/US2011/037398 patent/WO2011146873A1/en active Application Filing
- 2011-05-20 JP JP2013512101A patent/JP5888705B2/ja active Active
- 2011-05-20 RS RS20211027A patent/RS62335B1/sr unknown
- 2011-05-20 HR HRP20211363TT patent/HRP20211363T1/hr unknown
-
2013
- 2013-05-27 HK HK13106229.5A patent/HK1178562A1/xx unknown
-
2014
- 2014-10-09 US US14/510,570 patent/US9567280B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011146873A1 (en) | 2011-11-24 |
| HUE055712T2 (hu) | 2021-12-28 |
| US8871978B2 (en) | 2014-10-28 |
| RS62335B1 (sr) | 2021-10-29 |
| CN102906243A (zh) | 2013-01-30 |
| EP2571974A1 (en) | 2013-03-27 |
| US9567280B2 (en) | 2017-02-14 |
| EP2571974B1 (en) | 2021-06-23 |
| JP2013526603A (ja) | 2013-06-24 |
| US20110288335A1 (en) | 2011-11-24 |
| ES2886057T3 (es) | 2021-12-16 |
| HK1178562A1 (en) | 2013-09-13 |
| CN102906243B (zh) | 2014-11-12 |
| US20150094496A1 (en) | 2015-04-02 |
| JP5888705B2 (ja) | 2016-03-22 |
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