NO134732B - - Google Patents
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- Publication number
- NO134732B NO134732B NO4580/71A NO458071A NO134732B NO 134732 B NO134732 B NO 134732B NO 4580/71 A NO4580/71 A NO 4580/71A NO 458071 A NO458071 A NO 458071A NO 134732 B NO134732 B NO 134732B
- Authority
- NO
- Norway
- Prior art keywords
- isohumulones
- beer
- reduced
- humulones
- hops
- Prior art date
Links
- 229930193815 Isohumulone Natural products 0.000 claims description 67
- 235000013405 beer Nutrition 0.000 claims description 46
- 239000000284 extract Substances 0.000 claims description 26
- 235000008694 Humulus lupulus Nutrition 0.000 claims description 24
- 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 claims description 20
- 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 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 14
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- -1 isohexenoyl side chain Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 235000021577 malt beverage Nutrition 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003198 secondary alcohol group Chemical group 0.000 claims description 3
- 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 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 33
- 239000003208 petroleum Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 238000006722 reduction reaction Methods 0.000 description 18
- 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 description 16
- 238000006317 isomerization reaction Methods 0.000 description 15
- 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 12
- 239000002253 acid Substances 0.000 description 10
- 238000000605 extraction Methods 0.000 description 10
- VMSLCPKYRPDHLN-OAQYLSRUSA-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-OAQYLSRUSA-N 0.000 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 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000035943 smell Effects 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 238000013124 brewing process Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- VZMXLSLKOHIKTQ-UHFFFAOYSA-N Humulon Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O VZMXLSLKOHIKTQ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 235000019658 bitter taste Nutrition 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 241000266847 Mephitidae Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011946 reduction process Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000002798 spectrophotometry method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 2
- 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 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- RWECBKPOUYVUPL-UHFFFAOYSA-N Prehumulone Chemical compound CC(C)CCC(=O)C1=C(O)C(O)(CC=C(C)C)C(=O)C(CC=C(C)C)C1=O RWECBKPOUYVUPL-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000000469 ethanolic extract Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000019640 taste Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- LDXMPKMQIKGJFN-OKKPIIHCSA-N (6r)-3,5,6-trihydroxy-2-(2-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one Chemical compound CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@](O)(CC=C(C)C)C1=O LDXMPKMQIKGJFN-OKKPIIHCSA-N 0.000 description 1
- LDXMPKMQIKGJFN-SPLOXXLWSA-N Adhumulone Natural products O=C([C@@H](CC)C)C=1C(=O)[C@@](O)(C/C=C(\C)/C)C(O)=C(C/C=C(\C)/C)C=1O LDXMPKMQIKGJFN-SPLOXXLWSA-N 0.000 description 1
- DRSITEVYZGOOQG-UHFFFAOYSA-N Cohumulone Chemical compound CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O DRSITEVYZGOOQG-UHFFFAOYSA-N 0.000 description 1
- DRSITEVYZGOOQG-HXUWFJFHSA-N Cohumulone Natural products CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@](O)(CC=C(C)C)C1=O DRSITEVYZGOOQG-HXUWFJFHSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 229930186179 lupulin Natural products 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B21—MECHANICAL METAL-WORKING WITHOUT ESSENTIALLY REMOVING MATERIAL; PUNCHING METAL
- B21D—WORKING OR PROCESSING OF SHEET METAL OR METAL TUBES, RODS OR PROFILES WITHOUT ESSENTIALLY REMOVING MATERIAL; PUNCHING METAL
- B21D37/00—Tools as parts of machines covered by this subclass
- B21D37/04—Movable or exchangeable mountings for tools
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B26—HAND CUTTING TOOLS; CUTTING; SEVERING
- B26D—CUTTING; DETAILS COMMON TO MACHINES FOR PERFORATING, PUNCHING, CUTTING-OUT, STAMPING-OUT OR SEVERING
- B26D7/00—Details of apparatus for cutting, cutting-out, stamping-out, punching, perforating, or severing by means other than cutting
- B26D7/26—Means for mounting or adjusting the cutting member; Means for adjusting the stroke of the cutting member
- B26D7/2614—Means for mounting the cutting member
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B26—HAND CUTTING TOOLS; CUTTING; SEVERING
- B26F—PERFORATING; PUNCHING; CUTTING-OUT; STAMPING-OUT; SEVERING BY MEANS OTHER THAN CUTTING
- B26F1/00—Perforating; Punching; Cutting-out; Stamping-out; Apparatus therefor
- B26F1/38—Cutting-out; Stamping-out
- B26F1/44—Cutters therefor; Dies therefor
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14B—MECHANICAL TREATMENT OR PROCESSING OF SKINS, HIDES OR LEATHER IN GENERAL; PELT-SHEARING MACHINES; INTESTINE-SPLITTING MACHINES
- C14B5/00—Clicking, perforating, or cutting leather
- C14B5/02—Stamps or dies for leather articles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B26—HAND CUTTING TOOLS; CUTTING; SEVERING
- B26F—PERFORATING; PUNCHING; CUTTING-OUT; STAMPING-OUT; SEVERING BY MEANS OTHER THAN CUTTING
- B26F1/00—Perforating; Punching; Cutting-out; Stamping-out; Apparatus therefor
- B26F1/38—Cutting-out; Stamping-out
- B26F1/44—Cutters therefor; Dies therefor
- B26F2001/4463—Methods and devices for rule setting, fixation, preparing cutting dies
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T83/00—Cutting
- Y10T83/929—Tool or tool with support
- Y10T83/9457—Joint or connection
- Y10T83/9473—For rectilinearly reciprocating tool
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Forests & Forestry (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Perforating, Stamping-Out Or Severing By Means Other Than Cutting (AREA)
- Mounting, Exchange, And Manufacturing Of Dies (AREA)
- Moulds For Moulding Plastics Or The Like (AREA)
- Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE16877/70A SE338844B (enrdf_load_stackoverflow) | 1970-12-14 | 1970-12-14 |
Publications (2)
Publication Number | Publication Date |
---|---|
NO134732B true NO134732B (enrdf_load_stackoverflow) | 1976-08-30 |
NO134732C NO134732C (enrdf_load_stackoverflow) | 1976-12-08 |
Family
ID=20302925
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO4580/71A NO134732C (enrdf_load_stackoverflow) | 1970-12-14 | 1971-12-13 |
Country Status (11)
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE395644B (sv) * | 1976-02-24 | 1977-08-22 | Sandvik Ab | Anordning for fastsettning av stansknivar i en stodplatta |
CH681874A5 (enrdf_load_stackoverflow) * | 1990-04-10 | 1993-06-15 | Bobst Sa | |
EP0927093B1 (en) * | 1996-09-06 | 2007-08-15 | Ontario Die Company Limited | Cutting knife assembly |
US6658978B1 (en) * | 1999-10-15 | 2003-12-09 | Ontario Die International Inc. | Steel rule die with removable cutting units |
WO2004041489A1 (en) * | 2002-11-07 | 2004-05-21 | Ontario Die International Inc | Method and device for mounting a steel rule cutting die with improved scrap material removal |
CA2458309A1 (en) * | 2003-12-01 | 2005-06-01 | Ontario Die International Inc. | Punch for a braced die |
MXPA06006145A (es) * | 2003-12-01 | 2007-01-26 | Ontario Die Internat Inc | Punzon para un dado con abrazadera. |
DE102009033576A1 (de) * | 2009-07-16 | 2011-01-20 | WINKLER+DüNNEBIER AG | Rotationsstanze |
GB2528044B (en) | 2014-07-04 | 2018-08-22 | Arc Devices Ni Ltd | Non-touch optical detection of vital signs |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3354766A (en) * | 1965-06-14 | 1967-11-28 | Konink Metaalfab Voorheen J N | Tool carrying device for an eccentric press |
US3373643A (en) * | 1966-02-11 | 1968-03-19 | United Shoe Machinery Corp | Apparatus for punching out workpieces |
-
1970
- 1970-12-14 SE SE16877/70A patent/SE338844B/xx unknown
-
1971
- 1971-12-04 IT IT32065/71A patent/IT953145B/it active
- 1971-12-06 AU AU36522/71A patent/AU463423B2/en not_active Expired
- 1971-12-06 AT AT1046071A patent/AT314341B/de not_active IP Right Cessation
- 1971-12-10 US US00206801A patent/US3739676A/en not_active Expired - Lifetime
- 1971-12-13 NO NO4580/71A patent/NO134732C/no unknown
- 1971-12-13 FR FR7144617A patent/FR2118527A5/fr not_active Expired
- 1971-12-13 ES ES1971200877U patent/ES200877Y/es not_active Expired
- 1971-12-13 CA CA129,968A patent/CA942183A/en not_active Expired
- 1971-12-13 DK DK606471A patent/DK132209C/da active
- 1971-12-13 GB GB5782571A patent/GB1329906A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US3739676A (en) | 1973-06-19 |
DE2160933B2 (de) | 1976-02-19 |
CA942183A (en) | 1974-02-19 |
DK132209C (da) | 1976-04-20 |
AU3652271A (en) | 1973-06-14 |
FR2118527A5 (enrdf_load_stackoverflow) | 1972-07-28 |
ES200877U (es) | 1975-11-01 |
AT314341B (de) | 1974-03-25 |
ES200877Y (es) | 1976-02-16 |
DK132209B (da) | 1975-11-10 |
NO134732C (enrdf_load_stackoverflow) | 1976-12-08 |
AU463423B2 (en) | 1975-07-24 |
SE338844B (enrdf_load_stackoverflow) | 1971-09-20 |
IT953145B (it) | 1973-08-10 |
DE2160933A1 (de) | 1972-06-22 |
GB1329906A (en) | 1973-09-12 |
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