GB1266716A - - Google Patents

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Publication number
GB1266716A
GB1266716A GB1266716DA GB1266716A GB 1266716 A GB1266716 A GB 1266716A GB 1266716D A GB1266716D A GB 1266716DA GB 1266716 A GB1266716 A GB 1266716A
Authority
GB
United Kingdom
Prior art keywords
chloride
acylating
cis
trans
tetrahydroisohumulones
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.)
Expired
Application number
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 filed Critical
Publication of GB1266716A publication Critical patent/GB1266716A/en
Expired legal-status Critical Current

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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
    • C12C5/00—Other raw materials for the preparation of beer
    • C12C5/02—Additives for beer
    • C12C5/026—Beer flavouring preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
    • C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/296—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with lead derivatives
    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • 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
    • 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
    • C12C5/008—Hop surrogates
    • 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
    • C12C9/00—Methods specially adapted for the making of beerwort
    • C12C9/02—Beerwort treatment; Boiling with hops; Hop extraction
    • C12C9/025—Preparation of hop extracts ; Isomerisation of these extracts; Treatment of beerwort with these extracts; Surrogates of the hop
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Zoology (AREA)
  • General Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Saccharide Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,266,716. Tetrahydroisohumulones. ARTHUR GUINNESS SON & CO. (DUBLIN) Ltd. 14 Sept., 1970 [26 Sept., 1969], No. 47524/69. Heading C2C. The invention comprises crystalline (Œ) cis and (Œ) trans tetrahydroisohumulone. The cis and trans isomers of (Œ) tetrahydroisohumulone are prepared by acylating phloroglucinol with isovaleryl chloride and aluminium chloride to 2,4,6-trihydroxyisovalerophenone, reducing by the Clemmensen procedure to isopentylphloroglucinol, acylating with isovaleryl chloride and aluminium chloride to 2,4,6-trihydroxy-3-isopentylisovalerophenone, reducing by the Clemmensen procedure to diisopentylphloroglucinol, acylating with isovalenyl chloride and aluminium chloride to tetrahydro-4-desoxyhumulone, oxidizing to (Œ) tetrahydrohumulone and isomerizing to a mixture of (Œ) cis and (Œ) trans tetrahydroisohumulones.
GB1266716D 1969-09-26 1969-09-26 Expired GB1266716A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4752469 1969-09-26

Publications (1)

Publication Number Publication Date
GB1266716A true GB1266716A (en) 1972-03-15

Family

ID=10445289

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1266716D Expired GB1266716A (en) 1969-09-26 1969-09-26

Country Status (2)

Country Link
GB (1) GB1266716A (en)
IE (1) IE34530B1 (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4503256A (en) * 1981-07-02 1985-03-05 Noristan Limited Phlorophenone derivatives, processes for preparing such compounds, uses and pharmaceutical compositions of phlorophenone compounds
US4590296A (en) * 1984-01-25 1986-05-20 Miller Brewing Company Process for separation of beta-acids from extract containing alpha-acids and beta-acids
US4644084A (en) * 1984-01-25 1987-02-17 Miller Brewing Company Preparation of tetrahydroisohumulones
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
EP2364083A1 (en) * 2008-12-10 2011-09-14 Metaproteomics, LLC A method for the purification of substituted cyclopent-2-en-1-one congeners and substituted 1,3-cyclopentadione congeners from a complex mixture using countercurrent separation
WO2011146873A1 (en) * 2010-05-21 2011-11-24 Miller Brewing International, Inc. Preparation of hop acids and their derivatives
EP2632448A1 (en) * 2010-10-30 2013-09-04 KinDex Therapeutics, LLC Cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(-3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives, substantially enantiomerically pure compositions and methods

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4503256A (en) * 1981-07-02 1985-03-05 Noristan Limited Phlorophenone derivatives, processes for preparing such compounds, uses and pharmaceutical compositions of phlorophenone compounds
US4590296A (en) * 1984-01-25 1986-05-20 Miller Brewing Company Process for separation of beta-acids from extract containing alpha-acids and beta-acids
US4644084A (en) * 1984-01-25 1987-02-17 Miller Brewing Company Preparation of tetrahydroisohumulones
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
EP2364083A4 (en) * 2008-12-10 2012-10-31 Metaproteomics Llc A method for the purification of substituted cyclopent-2-en-1-one congeners and substituted 1,3-cyclopentadione congeners from a complex mixture using countercurrent separation
EP2364083A1 (en) * 2008-12-10 2011-09-14 Metaproteomics, LLC A method for the purification of substituted cyclopent-2-en-1-one congeners and substituted 1,3-cyclopentadione congeners from a complex mixture using countercurrent separation
WO2011146873A1 (en) * 2010-05-21 2011-11-24 Miller Brewing International, Inc. Preparation of hop acids and their derivatives
US8871978B2 (en) 2010-05-21 2014-10-28 Millercoors Llc Preparation of hop acids and their derivatives
US9567280B2 (en) 2010-05-21 2017-02-14 Millercoors Llc Preparation of hop acids and their derivatives
EP2632448A1 (en) * 2010-10-30 2013-09-04 KinDex Therapeutics, LLC Cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(-3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives, substantially enantiomerically pure compositions and methods
EP2632448A4 (en) * 2010-10-30 2014-03-19 Kindex Therapeutics Llc Cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(-3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives, substantially enantiomerically pure compositions and methods
US8829056B2 (en) 2010-10-30 2014-09-09 Kindex Pharmaceuticals, Inc. Cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl) cyclopent-2-en-1-one derivatives, substantially enantiomerically pure compositions and methods
AU2011320140B2 (en) * 2010-10-30 2016-12-01 Kindex Pharmaceuticals, Inc. Cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(-3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives, substantially enantiomerically pure compositions and methods
AU2011320140C1 (en) * 2010-10-30 2019-12-12 Kindex Pharmaceuticals, Inc. Cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(-3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives, substantially enantiomerically pure compositions and methods

Also Published As

Publication number Publication date
IE34530L (en) 1971-03-26
IE34530B1 (en) 1975-06-11

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees