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IE34530B1 - Tetrahydroisohumulones - Google Patents

Tetrahydroisohumulones

Info

Publication number
IE34530B1
IE34530B1 IE119970A IE119970A IE34530B1 IE 34530 B1 IE34530 B1 IE 34530B1 IE 119970 A IE119970 A IE 119970A IE 119970 A IE119970 A IE 119970A IE 34530 B1 IE34530 B1 IE 34530B1
Authority
IE
Ireland
Prior art keywords
chloride
acylating
cis
tetrahydroisohumulones
trans
Prior art date
Application number
IE119970A
Other versions
IE34530L (en
Original Assignee
Guinness Son & Co Ltd A
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 Guinness Son & Co Ltd A filed Critical Guinness Son & Co Ltd A
Publication of IE34530L publication Critical patent/IE34530L/en
Publication of IE34530B1 publication Critical patent/IE34530B1/en

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
    • 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. [GB1266716A]
IE119970A 1969-09-26 1970-09-15 Tetrahydroisohumulones IE34530B1 (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number Publication Date
IE34530L IE34530L (en) 1971-03-26
IE34530B1 true IE34530B1 (en) 1975-06-11

Family

ID=10445289

Family Applications (1)

Application Number Title Priority Date Filing Date
IE119970A IE34530B1 (en) 1969-09-26 1970-09-15 Tetrahydroisohumulones

Country Status (2)

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

Families Citing this family (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
CN102307465A (en) * 2008-12-10 2012-01-04 麦特普罗泰欧米克斯有限公司 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
CA2853974C (en) 2010-10-30 2020-11-10 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

Also Published As

Publication number Publication date
GB1266716A (en) 1972-03-15
IE34530L (en) 1971-03-26

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