HRP20211363T1 - Priprema kiselina hmelja i njihovih derivata - Google Patents

Priprema kiselina hmelja i njihovih derivata Download PDF

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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
Application number
HRP20211363TT
Other languages
English (en)
Inventor
Patrick L. Ting
Jason Pratt
David S. Ryder
Original Assignee
Coors Brewing Company
Priority date (The priority date 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 date listed.)
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Publication date
Application filed by Coors Brewing Company filed Critical Coors Brewing Company
Publication of HRP20211363T1 publication Critical patent/HRP20211363T1/hr

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/713Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/12Ketones
    • A61K31/122Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78Separation; Purification; Stabilisation; Use of additives
    • C07C45/85Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12CBEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C3/00Treatment of hops
    • C12C3/12Isomerised products from hops
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12CBEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C5/00Other raw materials for the preparation of beer
    • C12C5/02Additives for beer
    • C12C5/026Beer flavouring preparations

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  • 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.
HRP20211363TT 2010-05-21 2011-05-20 Priprema kiselina hmelja i njihovih derivata HRP20211363T1 (hr)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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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