CA1055412A - Preparation of a water soluble isomerised hop extract - Google Patents
Preparation of a water soluble isomerised hop extractInfo
- Publication number
- CA1055412A CA1055412A CA218,974A CA218974A CA1055412A CA 1055412 A CA1055412 A CA 1055412A CA 218974 A CA218974 A CA 218974A CA 1055412 A CA1055412 A CA 1055412A
- Authority
- CA
- Canada
- Prior art keywords
- isohumulone
- solution
- complex
- water
- alkali metal
- 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
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000000284 extract Substances 0.000 title description 10
- 229930193815 Isohumulone Natural products 0.000 claims abstract description 105
- 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 87
- 239000000243 solution Substances 0.000 claims abstract description 75
- 229910052751 metal Inorganic materials 0.000 claims abstract description 57
- 239000002184 metal Substances 0.000 claims abstract description 57
- 150000001339 alkali metal compounds Chemical class 0.000 claims abstract description 26
- 235000013361 beverage Nutrition 0.000 claims abstract description 26
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 17
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 15
- -1 alkali metal salt Chemical class 0.000 claims abstract description 14
- 239000012736 aqueous medium Substances 0.000 claims abstract description 12
- 235000013305 food Nutrition 0.000 claims abstract description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 239000002198 insoluble material Substances 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims description 53
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 28
- 239000011777 magnesium Substances 0.000 claims description 28
- 229910052749 magnesium Inorganic materials 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 235000013405 beer Nutrition 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 19
- 235000019832 sodium triphosphate Nutrition 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 16
- 229910052708 sodium Inorganic materials 0.000 claims description 14
- 239000011734 sodium Substances 0.000 claims description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 13
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- 239000011591 potassium Substances 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 8
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 7
- 238000013019 agitation Methods 0.000 claims description 7
- 229960001484 edetic acid Drugs 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 6
- 235000008694 Humulus lupulus Nutrition 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 8
- 239000011575 calcium Substances 0.000 claims 8
- 229910052791 calcium Inorganic materials 0.000 claims 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 159000000007 calcium salts Chemical class 0.000 claims 2
- 235000021554 flavoured beverage Nutrition 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 2
- 229910052748 manganese Inorganic materials 0.000 claims 2
- 239000011572 manganese Substances 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- 239000004565 water dispersible tablet Substances 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000000843 powder Substances 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000006317 isomerization reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 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 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 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 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 241000042812 Divales Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 235000019636 bitter flavor Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
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
- C12C3/12—Isomerised products from hops
-
- 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
- C12C3/06—Powder or pellets from hops
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Non-Alcoholic Beverages (AREA)
- Seasonings (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPB644374 | 1974-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055412A true CA1055412A (en) | 1979-05-29 |
Family
ID=3765843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA218,974A Expired CA1055412A (en) | 1974-02-04 | 1975-01-29 | Preparation of a water soluble isomerised hop extract |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3956513A (en, 2012) |
| JP (1) | JPS5653973B2 (en, 2012) |
| AT (1) | AT346796B (en, 2012) |
| AU (1) | AU476799B2 (en, 2012) |
| BE (1) | BE824927A (en, 2012) |
| BR (1) | BR7500719A (en, 2012) |
| CA (1) | CA1055412A (en, 2012) |
| CH (1) | CH610873A5 (en, 2012) |
| CS (1) | CS202034B2 (en, 2012) |
| DD (3) | DD121133A5 (en, 2012) |
| DE (1) | DE2504374C3 (en, 2012) |
| DK (1) | DK144130C (en, 2012) |
| ES (2) | ES434401A1 (en, 2012) |
| FR (1) | FR2259544B1 (en, 2012) |
| GB (1) | GB1452871A (en, 2012) |
| IE (1) | IE40575B1 (en, 2012) |
| IT (1) | IT1029414B (en, 2012) |
| NL (1) | NL176186C (en, 2012) |
| PH (1) | PH11469A (en, 2012) |
| PL (1) | PL100835B1 (en, 2012) |
| SE (1) | SE430260B (en, 2012) |
| ZA (1) | ZA75570B (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4511587A (en) * | 1982-01-07 | 1985-04-16 | The University Of Tasmania | Enzyme inactivated hops |
| JPS61181569U (en, 2012) * | 1985-05-01 | 1986-11-12 | ||
| US4956195A (en) * | 1987-04-03 | 1990-09-11 | Kalamazoo Holdings, Inc. | Hop flavors wherein deleterious odor-forming impurities have been removed |
| US5041300A (en) * | 1987-04-03 | 1991-08-20 | Kalamazoo Holdings, Inc. | Hop flavor which is odor forming impurity free |
| US5478580A (en) * | 1994-01-21 | 1995-12-26 | Coors Brewing Company | Method for the production of a purified iso-alpha-acid concentrate from hop extract |
| GB9509109D0 (en) * | 1995-05-04 | 1995-06-28 | British American Tobacco Co | Stabilisation of flavours |
| 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 |
| US20030031757A1 (en) * | 2001-08-03 | 2003-02-13 | Kraft Food Holdings, Inc. | Stable and bioavailable iron fortified beverages |
| US7456222B2 (en) * | 2002-05-17 | 2008-11-25 | Sequella, Inc. | Anti tubercular drug: compositions and methods |
| EP1970366A4 (en) * | 2005-12-08 | 2010-07-28 | Kirin Holdings Kk | CLATCH OF AN ISOHUMULIN COMPOUND AND COMPOSITION THAT CONTAINS THIS |
| EP2055766A1 (en) * | 2007-10-29 | 2009-05-06 | Inbev S.A. | Process for bittering a fermented beverage with hops |
| US8980953B2 (en) | 2009-06-12 | 2015-03-17 | Kirin Holdings Kabushiki Kaisha | Alkaline decomposition product of hop extract and use thereof |
| CN103327832B (zh) * | 2011-01-24 | 2016-08-10 | 富士胶片株式会社 | 经口用组合物 |
| GB201318568D0 (en) * | 2013-10-21 | 2013-12-04 | Ifast Nv | Method for extraction and dissolution of hop acids in aqueous media |
| US20200222449A1 (en) * | 2019-02-01 | 2020-07-16 | Thermolife International, Llc | Enhanced Nitrate Compositions and Methods of Use |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3607300A (en) * | 1965-11-17 | 1971-09-21 | Bush Boake Allen Ltd | Preparation of isohumulone containing hop extract |
| DE1618059B1 (de) * | 1967-05-02 | 1971-07-15 | Atlantic Res Inst Ltd | Verfahren zur Herstellung von Isohumulon |
| GB1362695A (en) * | 1970-09-17 | 1974-08-07 | Carlton & United Breweries | Isomerised hop extract |
| FR2174974B1 (en, 2012) * | 1972-03-07 | 1977-09-02 | Carlton & United Breweries |
-
1974
- 1974-02-04 AU AU77846/75A patent/AU476799B2/en not_active Expired
-
1975
- 1975-01-28 ZA ZA00750570A patent/ZA75570B/xx unknown
- 1975-01-28 US US05/544,705 patent/US3956513A/en not_active Expired - Lifetime
- 1975-01-29 BE BE152833A patent/BE824927A/xx not_active IP Right Cessation
- 1975-01-29 FR FR7502761A patent/FR2259544B1/fr not_active Expired
- 1975-01-29 CA CA218,974A patent/CA1055412A/en not_active Expired
- 1975-01-30 IE IE181/75A patent/IE40575B1/xx unknown
- 1975-01-30 IT IT47934/75A patent/IT1029414B/it active
- 1975-01-31 CH CH118475A patent/CH610873A5/xx not_active IP Right Cessation
- 1975-01-31 SE SE7501084A patent/SE430260B/xx not_active IP Right Cessation
- 1975-01-31 PH PH16758A patent/PH11469A/en unknown
- 1975-02-01 PL PL1975177755A patent/PL100835B1/pl unknown
- 1975-02-03 ES ES434401A patent/ES434401A1/es not_active Expired
- 1975-02-03 JP JP1421375A patent/JPS5653973B2/ja not_active Expired
- 1975-02-03 GB GB457675A patent/GB1452871A/en not_active Expired
- 1975-02-03 DK DK36275A patent/DK144130C/da not_active IP Right Cessation
- 1975-02-03 DE DE2504374A patent/DE2504374C3/de not_active Expired
- 1975-02-03 CS CS75683A patent/CS202034B2/cs unknown
- 1975-02-04 BR BR719/75A patent/BR7500719A/pt unknown
- 1975-02-04 DD DD183990A patent/DD121133A5/xx unknown
- 1975-02-04 DD DD7500194527A patent/DD129289A5/xx unknown
- 1975-02-04 DD DD194528A patent/DD127568A5/xx unknown
- 1975-02-04 AT AT81575A patent/AT346796B/de not_active IP Right Cessation
- 1975-02-04 NL NLAANVRAGE7501322,A patent/NL176186C/xx not_active IP Right Cessation
-
1976
- 1976-10-30 ES ES452899A patent/ES452899A1/es not_active Expired
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