CA1144095A - Extraits de houblon, et methode de preparation connexe - Google Patents

Extraits de houblon, et methode de preparation connexe

Info

Publication number: CA1144095A
Authority: CA; Canada
Prior art keywords: reduced; organic phase; aqueous; isohumulone; hop
Prior art date: 1981-07-09
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

CA000381373A

Other languages

English (en)

Inventor

Patrick Ting

Henry Goldstein

Walter Fly

Etzer Chicoye

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.)

Miller Brewing Co

Original Assignee

Miller Brewing Co

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.)

1981-07-09

Filing date

1981-07-09

Publication date

1983-04-05

1981-07-09 Application filed by Miller Brewing Co filed Critical Miller Brewing Co

1981-07-09 Priority to CA000381373A priority Critical patent/CA1144095A/fr

1983-04-05 Application granted granted Critical

1983-04-05 Publication of CA1144095A publication Critical patent/CA1144095A/fr

Status Expired legal-status Critical Current

Links

239000000284 extract Substances 0.000 title claims abstract description 46
238000000034 method Methods 0.000 title claims abstract description 38
238000002360 preparation method Methods 0.000 title claims abstract description 12
229930193815 Isohumulone Natural products 0.000 claims abstract description 45
239000012074 organic phase Substances 0.000 claims abstract description 42
QARXXMMQVDCYGZ-UHFFFAOYSA-N isohumulone Chemical compound CC(C)CC(=O)C1=C(O)C(O)(C(=O)CC=C(C)C)C(CC=C(C)C)C1=O QARXXMMQVDCYGZ-UHFFFAOYSA-N 0.000 claims abstract description 40
239000008346 aqueous phase Substances 0.000 claims abstract description 37
239000000203 mixture Substances 0.000 claims abstract description 23
238000000926 separation method Methods 0.000 claims abstract description 17
239000003960 organic solvent Substances 0.000 claims abstract description 15
235000021577 malt beverage Nutrition 0.000 claims abstract description 11
239000011541 reaction mixture Substances 0.000 claims abstract description 10
RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 claims abstract description 7
VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 claims abstract description 7
238000010438 heat treatment Methods 0.000 claims abstract description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 47
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
239000002253 acid Substances 0.000 claims description 35
150000007513 acids Chemical class 0.000 claims description 35
239000000654 additive Substances 0.000 claims description 25
230000000996 additive effect Effects 0.000 claims description 24
235000008694 Humulus lupulus Nutrition 0.000 claims description 18
239000000243 solution Substances 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 11
239000000470 constituent Substances 0.000 claims description 10
239000000463 material Substances 0.000 claims description 8
239000004215 Carbon black (E152) Substances 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
150000002430 hydrocarbons Chemical class 0.000 claims description 6
239000012670 alkaline solution Substances 0.000 claims description 4
239000000287 crude extract Substances 0.000 claims description 4
-1 reduced isohumulone Chemical class 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
239000012071 phase Substances 0.000 abstract description 13
235000013405 beer Nutrition 0.000 abstract description 8
239000005454 flavour additive Substances 0.000 abstract 1
235000013355 food flavoring agent Nutrition 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
229910002092 carbon dioxide Inorganic materials 0.000 description 10
239000007787 solid Substances 0.000 description 10
206010001497 Agitation Diseases 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000013019 agitation Methods 0.000 description 8
239000012279 sodium borohydride Substances 0.000 description 8
229910000033 sodium borohydride Inorganic materials 0.000 description 8
238000010908 decantation Methods 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000013124 brewing process Methods 0.000 description 5
239000001569 carbon dioxide Substances 0.000 description 5
238000005119 centrifugation Methods 0.000 description 5
238000000605 extraction Methods 0.000 description 5
OLHLJBVALXTBSQ-UHFFFAOYSA-N Lupulone Natural products CC(C)CC(=O)C1C(=O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O OLHLJBVALXTBSQ-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
LSDULPZJLTZEFD-UHFFFAOYSA-N lupulone Chemical class CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O LSDULPZJLTZEFD-UHFFFAOYSA-N 0.000 description 4
238000005191 phase separation Methods 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
229940032330 sulfuric acid Drugs 0.000 description 4
VMSLCPKYRPDHLN-UHFFFAOYSA-N (R)-Humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000000638 solvent extraction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
235000013361 beverage Nutrition 0.000 description 2
235000019636 bitter flavor Nutrition 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
QHRQNLXYMFCGPB-UHFFFAOYSA-N 3,4-dihydroxy-2-(2-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one Chemical compound CCC(C)C(=O)C1=C(O)C(O)(C(=O)CC=C(C)C)C(CC=C(C)C)C1=O QHRQNLXYMFCGPB-UHFFFAOYSA-N 0.000 description 1
KKXFYHZSOIALRM-UHFFFAOYSA-N 3,4-dihydroxy-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)-2-(2-methylpropanoyl)cyclopent-2-en-1-one Chemical compound CC(C)C(=O)C1=C(O)C(O)(C(=O)CC=C(C)C)C(CC=C(C)C)C1=O KKXFYHZSOIALRM-UHFFFAOYSA-N 0.000 description 1
QRDZSRWEULKVNW-UHFFFAOYSA-N 6-hydroxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical compound C1=C(O)C=C2C(C(=O)O)=CC(=O)NC2=C1 QRDZSRWEULKVNW-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
239000012223 aqueous fraction Substances 0.000 description 1
WPVSVIXDXMNGGN-UHFFFAOYSA-N beta-bitter acid Natural products CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O WPVSVIXDXMNGGN-UHFFFAOYSA-N 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
150000001639 boron compounds Chemical class 0.000 description 1
239000003518 caustics Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000000727 fraction Substances 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000011368 organic material Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)

CA000381373A 1981-07-09 1981-07-09 Extraits de houblon, et methode de preparation connexe Expired CA1144095A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000381373A CA1144095A (fr)	1981-07-09	1981-07-09	Extraits de houblon, et methode de preparation connexe

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000381373A CA1144095A (fr)	1981-07-09	1981-07-09	Extraits de houblon, et methode de preparation connexe

Publications (1)

Publication Number	Publication Date
CA1144095A true CA1144095A (fr)	1983-04-05

Family

ID=4120394

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000381373A Expired CA1144095A (fr)	1981-07-09	1981-07-09	Extraits de houblon, et methode de preparation connexe

Country Status (1)

Country	Link
CA (1)	CA1144095A (fr)

1981
- 1981-07-09 CA CA000381373A patent/CA1144095A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-04-05	MKEX	Expiry

Publication	Publication Date	Title
US4324810A (en)	1982-04-13	Hop extracts and method of preparation
US5073396A (en)	1991-12-17	Beer flavored with a non-acidic hop-flavor fraction
US5155276A (en)	1992-10-13	Process for the isomerization of humulone in a carbon dioxide-hops extract and a process for the isolation of isohumulone from it
US4767640A (en)	1988-08-30	Light stable hop extracts and method of preparation
US4298626A (en)	1981-11-03	Production of an iso-α-acid preparation from hops
US4590296A (en)	1986-05-20	Process for separation of beta-acids from extract containing alpha-acids and beta-acids
US4644084A (en)	1987-02-17	Preparation of tetrahydroisohumulones
EP0442621B1 (fr)	1996-05-15	Procédé pour préparation d'acides tetrahydroisoalpha et hexahydroisoalpha
US5041300A (en)	1991-08-20	Hop flavor which is odor forming impurity free
US4778691A (en)	1988-10-18	Removal of deleterious odor-forming impurities from hop flavors
US4666731A (en)	1987-05-19	Separation of the constituents of CO2 hop extracts
US3364265A (en)	1968-01-16	Hop constituents and method of making same
US3875316A (en)	1975-04-01	Preparation of isomerized hop extracts
CZ278141B6 (en)	1993-09-15	Process for preparing isomerized hop product
US4247483A (en)	1981-01-27	Production of iso-α-acids
AU664916B2 (en)	1995-12-07	Production of isomerized hop extract
EP0679419B1 (fr)	2000-02-02	Extraction du houblon
EP0161806B1 (fr)	1988-07-06	Méthode pour augmenter l'amertume de la bière
US4160787A (en)	1979-07-10	Process for extracting bitter flavoring principles from hops
US3607298A (en)	1971-09-21	Hop concentrates
US4759941A (en)	1988-07-26	Anactinic hopping materials and method of preparation
CA1144095A (fr)	1983-04-05	Extraits de houblon, et methode de preparation connexe
EP0339147B1 (fr)	1994-03-02	Produits de houblonnage anactiniques et méthode pour leur préparation
US3892808A (en)	1975-07-01	Hop extracts
US4507329A (en)	1985-03-26	Mixed solvent extraction of hops