CA2151256A1 - Production of odor-free tetrahydroisohumulates - Google Patents

Production of odor-free tetrahydroisohumulates

Info

Publication number
CA2151256A1
CA2151256A1 CA002151256A CA2151256A CA2151256A1 CA 2151256 A1 CA2151256 A1 CA 2151256A1 CA 002151256 A CA002151256 A CA 002151256A CA 2151256 A CA2151256 A CA 2151256A CA 2151256 A1 CA2151256 A1 CA 2151256A1
Authority
CA
Canada
Prior art keywords
odor
alkali metal
produced
free
thih
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.)
Granted
Application number
CA002151256A
Other languages
French (fr)
Other versions
CA2151256C (en
Inventor
Larry J. Stegink
James A. Guzinski
Paul H. Todd, Jr.
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kalamazoo Holdings Inc
Original Assignee
Larry J. Stegink
James A. Guzinski
Paul H. Todd, Jr.
Kalamazoo Holdings, Inc.
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.)
Filing date
Publication date
Application filed by Larry J. Stegink, James A. Guzinski, Paul H. Todd, Jr., Kalamazoo Holdings, Inc. filed Critical Larry J. Stegink
Publication of CA2151256A1 publication Critical patent/CA2151256A1/en
Application granted granted Critical
Publication of CA2151256C publication Critical patent/CA2151256C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • 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
    • C07C49/707—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a three- to five-membered ring

Abstract

The present application discloses a novel and advantageous method for the preparation of essentially odor-free alkali metal tetrahydroisohumulate (THIH) which proceeds through isomerization of the essential alkali metal tetrahydrohumulate (THH) intermediate, which is in turn produced by the hydrogenation with two moles of hydrogen of a starting alkali metal humulate (H) at a pH of at least 10, the intermediate THH being thus produced with relative ease and in high yields and purity, which high yields and purity carry over to the ultimate end product, namely, to the essentially aroma-, odor-, and impurity-free THIN, which end product accordingly does not require steam- stripping or other cleanup procedure as is conventional for THIH
produced from other sources or by other procedure.
CA002151256A 1992-12-31 1993-12-27 Production of odor-free tetrahydroisohumulates Expired - Lifetime CA2151256C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US999,599 1992-12-31
US07/999,599 US5296637A (en) 1992-12-31 1992-12-31 Production of odor-free tetrahydroisohumulates from alpha acids via their tetrahydrohumulates and subsequent isomerization
PCT/US1993/012582 WO1994015899A1 (en) 1992-12-31 1993-12-27 Production of odor-free tetrahydroisohumulates

Publications (2)

Publication Number Publication Date
CA2151256A1 true CA2151256A1 (en) 1994-07-21
CA2151256C CA2151256C (en) 2001-12-11

Family

ID=25546516

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002151256A Expired - Lifetime CA2151256C (en) 1992-12-31 1993-12-27 Production of odor-free tetrahydroisohumulates

Country Status (4)

Country Link
US (1) US5296637A (en)
EP (1) EP0677036B1 (en)
CA (1) CA2151256C (en)
WO (1) WO1994015899A1 (en)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5523489A (en) * 1995-02-07 1996-06-04 Miller Brewing Company Preparation of tetrahydroisohumulones
US5600012A (en) * 1995-04-06 1997-02-04 John I. Haas, Inc. Process for producing tetrahydroisoalpha acids
US6020019A (en) * 1996-03-26 2000-02-01 Miller Brewing Company Hydrogenation of hop soft resins using CO2
DE19620171A1 (en) * 1996-05-20 1997-11-27 Nigu Chemie Gmbh Process for the catalytic hydrogenation of terpenoids
US5965777A (en) * 1996-10-29 1999-10-12 Cultor Food Service, Inc. Process to remove catalyst poisons from hop extracts
US5874633A (en) * 1996-10-30 1999-02-23 Miller Brewing Company Concentrated single phase aqueous solutions of tetrahydroiso-α-acids and methods of preparing the same
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
US6198004B1 (en) 1999-06-10 2001-03-06 Haas Hop Products, Inc. Process for hydrogenation of isoalpha acids
US6303824B1 (en) 1999-11-11 2001-10-16 Miller Brewing Company Method of hydrogenating iso-α acids in a buffered solution
US7344746B1 (en) 1999-11-18 2008-03-18 S.S. Steiner, Inc. Process for the hydrogenation of hop resin acids
US6583322B1 (en) 2000-02-25 2003-06-24 Kalamazoo Holdings, Inc. Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same
US20040219240A1 (en) * 2001-06-20 2004-11-04 Babish John G. Anti-inflammatory pharmaceutical compositions for reducing inflammation and the treatment or prevention of gastric toxicity
US7815944B2 (en) * 2001-06-20 2010-10-19 Metaproteomics, Llc Anti-inflammatory pharmaceutical compositions for reducing inflammation and the treatment of prevention of gastric toxicity
US20040115290A1 (en) * 2001-06-20 2004-06-17 Tripp Matthew L. Modulation of inflammation by hops fractions and derivatives
US7901713B2 (en) * 2001-06-20 2011-03-08 Metaproteomics, Llc Inhibition of COX-2 and/or 5-LOX activity by fractions isolated or derived from hops
US8168234B2 (en) 2001-06-20 2012-05-01 Metaproteomics, Llc Compositions that treat or inhibit pathological conditions associated with inflammatory response
US7901714B2 (en) * 2001-06-20 2011-03-08 Metaproteomics, Llp Treatment modalities for autoimmune diseases
US7718198B2 (en) * 2001-06-20 2010-05-18 Metaproteomics, Llc Treatment modalities for autoimmune diseases
US8142819B2 (en) 2002-10-21 2012-03-27 Metaproteomics, Llc Synergistic compositions that treat or inhibit pathological conditions associated with inflammatory response
US8206753B2 (en) * 2001-06-20 2012-06-26 Metaproteomics, Llc Anti-inflammatory botanical products for the treatment of metabolic syndrome and diabetes
US7270835B2 (en) * 2001-06-20 2007-09-18 Metaproteomics, Llc Compositions that treat or inhibit pathological conditions associated with inflammatory response
US7205151B2 (en) * 2001-06-20 2007-04-17 Metaproteomics, Llc Complex mixtures exhibiting selective inhibition of cyclooxygenase-2
US7279185B2 (en) * 2001-10-26 2007-10-09 Metaproteonics, Llc Curcuminoid compositions exhibiting synergistic inhibition of the expression and/or activity of cyclooxygenase-2
US20090263522A1 (en) * 2001-10-26 2009-10-22 Babish John G Curcuminoid Compositions Exhibiting Synergistic Inhibition Of The Expression And/Or Activity Of Cyclooxygenase-2
US8158160B2 (en) 2001-11-13 2012-04-17 Eric Hauser Kuhrts Anti-inflammatory cyclooxygenase inhibitors
US7413758B2 (en) * 2002-03-26 2008-08-19 Millercoors Llc Preparation of light stable hop products
US7258887B2 (en) * 2002-03-26 2007-08-21 Miller Brewing Company Preparation of light stable hops
KR20050071605A (en) * 2002-10-21 2005-07-07 메타프로테오믹스, 엘엘씨 Compositions that treat or inhibit pathological conditions associated with inflammatory response
KR20060105429A (en) * 2003-05-22 2006-10-11 메타프로테오믹스, 엘엘씨 Anti-inflammatory pharmaceutical compositions for reducing inflammation and the treatment or prevention of gastric toxicity
US20050192356A1 (en) * 2004-02-27 2005-09-01 Babish John G. Synergistic anti-inflammatory pharmaceutical compositions and methods of use
US7914831B2 (en) 2004-02-27 2011-03-29 Metaproteomics, Llc Synergistic anti-inflammatory pharmaceutical compositions and related methods using curcuminoids or methylxanthines
WO2007021694A2 (en) * 2005-08-09 2007-02-22 Metaproteomics, Llc Protein kinase modulation by hops and acacia products
NZ568860A (en) * 2005-12-09 2012-09-28 Metaproteomics Llc Protein kinase modulation by hops and acacia products
US20080051466A1 (en) * 2006-06-20 2008-02-28 Metaproteomics, Llc Isoalpha acid based protein kinase modulation cancer treatment
WO2007149482A2 (en) * 2006-06-20 2007-12-27 Metaproteomics, Llc Xanthohumol based protein kinase modulation cancer treatment
AU2008229110A1 (en) * 2007-03-19 2008-09-25 Metaproteomics, Llc Methods and compositions for promoting bone and joint health
US8241674B2 (en) 2007-05-11 2012-08-14 Metaproteomics, Llc Methods and compositions for heavy metal detoxification
EP2229178A4 (en) * 2007-12-10 2011-03-09 Metaproteomics Llc Substituted 1,3-cyclopentadione multi-target protein kinase modulators of cancer, angiogenesis and the inflammatory pathways associated therewith
AU2009231723B2 (en) * 2008-04-02 2014-04-17 Metaproteomics, Llc. Substituted 1,3-cyclopentadione attenuated endothelial inflammation and endothelial-monocyte interactions
WO2011059486A1 (en) 2009-11-13 2011-05-19 Kalamazoo Holdings, Inc. Process for the preparation of tetrahydroisohumulone compositions
US9222064B1 (en) 2014-08-18 2015-12-29 Hop Ting Resources, LLC Solvent-free processes for making light stable ISO-alpha-acids derivatives from both hop alpha-acids and beta-acids resins

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4002683A (en) * 1971-05-03 1977-01-11 Kalsec, Inc. Process for isomerizing alpha acids to iso-alpha acids
US3923897A (en) * 1973-04-02 1975-12-02 Kalamazoo Spice Extract Co Production of hoplike beverage bittering materials
US4234516A (en) * 1975-06-02 1980-11-18 Atlantic Research Institute Limited Method of isomerizing humulone to isohumulone by catalytic acceleration with metal salts
US4007683A (en) 1976-05-11 1977-02-15 Dickerson Henry R Auxiliary drive and sprocket adapter for ink fountain roller
ZA792350B (en) * 1978-05-26 1980-05-28 Brewing Patents Ltd Production of iso-alpha acids
US4666731A (en) * 1984-02-28 1987-05-19 Kalamazoo Holdings, Inc. Separation of the constituents of CO2 hop extracts
US4778691A (en) * 1987-04-03 1988-10-18 Kalamazoo Holdings, Inc. Removal of deleterious odor-forming impurities from hop flavors
US5013572A (en) * 1990-01-31 1991-05-07 Pfizer Inc. Steam stripping of odor forming impurities from hop flavors
US5013571A (en) * 1990-01-31 1991-05-07 Pfizer Inc. Methods for making tetrahydroisoalpha and hexahydroisoalpha acids

Also Published As

Publication number Publication date
EP0677036A1 (en) 1995-10-18
WO1994015899A1 (en) 1994-07-21
EP0677036B1 (en) 1998-10-07
US5296637A (en) 1994-03-22
EP0677036A4 (en) 1996-01-10
CA2151256C (en) 2001-12-11

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Effective date: 20131227