CA2400177A1 - Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same - Google Patents

Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same Download PDF

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Publication number
CA2400177A1
CA2400177A1 CA002400177A CA2400177A CA2400177A1 CA 2400177 A1 CA2400177 A1 CA 2400177A1 CA 002400177 A CA002400177 A CA 002400177A CA 2400177 A CA2400177 A CA 2400177A CA 2400177 A1 CA2400177 A1 CA 2400177A1
Authority
CA
Canada
Prior art keywords
trans
high ratio
cis isomers
dihydro
isoalpha acids
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
CA002400177A
Other languages
French (fr)
Other versions
CA2400177C (en
Inventor
Khalil Shahlai
Randall H. Mennett
Paul H. Todd
James A. Guzinski
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
Kalamazoo Holdings, Inc.
Khalil Shahlai
Randall H. Mennett
Paul H. Todd
James A. Guzinski
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 Kalamazoo Holdings, Inc., Khalil Shahlai, Randall H. Mennett, Paul H. Todd, James A. Guzinski filed Critical Kalamazoo Holdings, Inc.
Publication of CA2400177A1 publication Critical patent/CA2400177A1/en
Application granted granted Critical
Publication of CA2400177C publication Critical patent/CA2400177C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C12C3/04—Conserving; Storing; Packing
    • C12C3/08—Solvent extracts from hops
    • C12C3/085—Extraction of hops with beerwort
    • 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

Abstract

This invention describes heretofore unknown forms of dihydro (DHIA) and hexahydro (HHIA) isoalpha acids having a high ratio of trans to cis isomers and a process for their production. Also, non-precipitating clear 5, 10, 20 % and higher aqueous solutions thereof, since they are soluble at room temperature in soft water. This is due to the high ratio of trans to cis isomers. Unlike prior art essentially all cis isomer products, they remain haze free both at a neutral pH in water and at 1 % to 2 % and higher concentrations. This invention has the advantage over the prior art in that DHIA and HHIA can be provided as stable, non-separating liquids, at practical concentrations in the range of 5 % to about 40 %, which do not require heating to about 50°
to 90 °C and above with stirring to effect dissolution of precipitates. The high trans products described herein can be admixed with isoalpha- and tetrahydro-isoalpha acids.
CA002400177A 2000-02-25 2001-02-20 Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same Expired - Lifetime CA2400177C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/512,944 US6583322B1 (en) 2000-02-25 2000-02-25 Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same
US09/512,944 2000-02-25
PCT/US2001/005339 WO2001062697A1 (en) 2000-02-25 2001-02-20 Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same

Publications (2)

Publication Number Publication Date
CA2400177A1 true CA2400177A1 (en) 2001-08-30
CA2400177C CA2400177C (en) 2007-09-18

Family

ID=24041262

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002400177A Expired - Lifetime CA2400177C (en) 2000-02-25 2001-02-20 Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same

Country Status (6)

Country Link
US (2) US6583322B1 (en)
EP (1) EP1263704B1 (en)
AT (1) ATE361908T1 (en)
CA (1) CA2400177C (en)
DE (1) DE60128331D1 (en)
WO (1) WO2001062697A1 (en)

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US7205151B2 (en) * 2001-06-20 2007-04-17 Metaproteomics, Llc Complex mixtures exhibiting selective inhibition of cyclooxygenase-2
US7718198B2 (en) * 2001-06-20 2010-05-18 Metaproteomics, Llc Treatment modalities for autoimmune diseases
US7666449B2 (en) * 2001-06-20 2010-02-23 Metaproteomics, Llc Anti-inflammatory pharmaceutical compositions for reducing inflammation and the treatment or prevention of gastric toxicity
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
US8142819B2 (en) * 2002-10-21 2012-03-27 Metaproteomics, Llc Synergistic compositions that treat or inhibit pathological conditions associated with inflammatory response
US20040115290A1 (en) * 2001-06-20 2004-06-17 Tripp Matthew L. Modulation of inflammation by hops fractions and derivatives
US8206753B2 (en) * 2001-06-20 2012-06-26 Metaproteomics, Llc Anti-inflammatory botanical products for the treatment of metabolic syndrome and diabetes
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
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
US7279185B2 (en) 2001-10-26 2007-10-09 Metaproteonics, Llc 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
EP1558271A4 (en) * 2002-10-21 2006-01-11 Metaproteomics Llc Compositions that treat or inhibit pathological conditions associated with inflammatory response
GB0306568D0 (en) * 2003-03-21 2003-04-30 Unilever Plc Compositions of natural products and use thereof
JP2007527407A (en) * 2003-05-22 2007-09-27 メタプロテオミクス， エルエルシー Anti-inflammatory pharmaceutical composition for reducing inflammation and for treating or preventing gastrointestinal toxicity
AU2003903501A0 (en) * 2003-07-07 2003-07-24 Commonwealth Scientific And Industrial Research Organisation A method of forming a reflective authentication device
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
MX2007005697A (en) * 2004-11-13 2007-10-08 Metaproteomics Llc Compositions exhibiting inhibition of cyclooxygenase-2.
WO2006065131A1 (en) * 2004-11-22 2006-06-22 Universiteit Leiden, Faculteit Van Wiskunde En Natuurwetenschappen Method of improving the stability of hop extracts and hop flavoured beverages
WO2007021694A2 (en) * 2005-08-09 2007-02-22 Metaproteomics, Llc Protein kinase modulation by hops and acacia products
AU2006321727A1 (en) * 2005-12-09 2007-06-14 Metaproteomics, Llc Protein kinase modulation by hops and Acacia products
WO2007149482A2 (en) * 2006-06-20 2007-12-27 Metaproteomics, Llc Xanthohumol based protein kinase modulation cancer treatment
US20080051466A1 (en) * 2006-06-20 2008-02-28 Metaproteomics, Llc Isoalpha acid based protein kinase modulation cancer treatment
MX2009010049A (en) * 2007-03-19 2010-03-04 Metaproteomics Llc Methods and compositions for promoting bone and joint health.
KR20100029201A (en) * 2007-05-11 2010-03-16 메타프로테오믹스, 엘엘씨 Methods and compositions for heavy metal detoxification
MX2010006425A (en) * 2007-12-10 2010-08-31 Metaproteomics Llc Substituted 1,3-cyclopentadione multi-target protein kinase modulators of cancer, angiogenesis and the inflammatory pathways associated therewith.
JP2011516492A (en) * 2008-04-02 2011-05-26 メタプロテオミクス， エルエルシー Attenuation of endothelial inflammation and endothelium-monocyte interaction by substituted 1,3-cyclopentadione
US9796955B2 (en) * 2010-05-24 2017-10-24 S.S. Steiner, Inc. Natural and stable solutions of alpha-acids and their use for the improvement of foam quality of beer

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Also Published As

Publication number Publication date
CA2400177C (en) 2007-09-18
US20020007084A1 (en) 2002-01-17
EP1263704B1 (en) 2007-05-09
ATE361908T1 (en) 2007-06-15
US6521796B2 (en) 2003-02-18
DE60128331D1 (en) 2007-06-21
EP1263704A4 (en) 2004-08-25
WO2001062697A1 (en) 2001-08-30
US6583322B1 (en) 2003-06-24
EP1263704A1 (en) 2002-12-11

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Effective date: 20210222