NO134895B - - Google Patents
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- Publication number
- NO134895B NO134895B NO5181/69A NO518169A NO134895B NO 134895 B NO134895 B NO 134895B NO 5181/69 A NO5181/69 A NO 5181/69A NO 518169 A NO518169 A NO 518169A NO 134895 B NO134895 B NO 134895B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- denotes
- group
- ethyl
- coffee
- Prior art date
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- 235000016213 coffee Nutrition 0.000 claims abstract description 25
- 235000013353 coffee beverage Nutrition 0.000 claims abstract description 25
- 235000021539 instant coffee Nutrition 0.000 claims abstract description 11
- 235000013361 beverage Nutrition 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- -1 methyl- Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 150000003216 pyrazines Chemical class 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 2
- 239000000796 flavoring agent Substances 0.000 abstract description 26
- 235000019634 flavors Nutrition 0.000 abstract description 9
- 238000000034 method Methods 0.000 description 70
- 238000009835 boiling Methods 0.000 description 55
- 150000001875 compounds Chemical class 0.000 description 48
- 239000000047 product Substances 0.000 description 45
- 239000000203 mixture Substances 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 235000013355 food flavoring agent Nutrition 0.000 description 17
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 14
- LCZUOKDVTBMCMX-UHFFFAOYSA-N 2,5-Dimethylpyrazine Chemical compound CC1=CN=C(C)C=N1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 239000001934 2,5-dimethylpyrazine Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- HJFZAYHYIWGLNL-UHFFFAOYSA-N 2,6-Dimethylpyrazine Chemical group CC1=CN=CC(C)=N1 HJFZAYHYIWGLNL-UHFFFAOYSA-N 0.000 description 6
- LNIMMWYNSBZESE-UHFFFAOYSA-N 2-Ethyl-3-methylpyrazine, 9CI Chemical compound CCC1=NC=CN=C1C LNIMMWYNSBZESE-UHFFFAOYSA-N 0.000 description 6
- KANZWHBYRHQMKZ-UHFFFAOYSA-N 2-ethenylpyrazine Chemical compound C=CC1=CN=CC=N1 KANZWHBYRHQMKZ-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004157 Nitrosyl chloride Substances 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 6
- 235000019392 nitrosyl chloride Nutrition 0.000 description 6
- IAEGWXHKWJGQAZ-UHFFFAOYSA-N trimethylpyrazine Chemical compound CC1=CN=C(C)C(C)=N1 IAEGWXHKWJGQAZ-UHFFFAOYSA-N 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- WAVOLMBVDCRBGR-UHFFFAOYSA-N 2,5-Diethylpyrazine Chemical compound CCC1=CN=C(CC)C=N1 WAVOLMBVDCRBGR-UHFFFAOYSA-N 0.000 description 4
- QDWOWLUANUBTGE-UHFFFAOYSA-N 2,6-Diethylpyrazine Chemical compound CCC1=CN=CC(CC)=N1 QDWOWLUANUBTGE-UHFFFAOYSA-N 0.000 description 4
- WHMWOHBXYIZFPF-UHFFFAOYSA-N 2-ethyl-3,(5 or 6)-dimethylpyrazine Chemical compound CCC1=NC(C)=CN=C1C WHMWOHBXYIZFPF-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- GFHPSQFCHUIFTO-UHFFFAOYSA-N 2-(chloromethyl)pyrazine Chemical compound ClCC1=CN=CC=N1 GFHPSQFCHUIFTO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 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 description 3
- VQFGDOHENLRPFB-UHFFFAOYSA-N Pyrazinemethanethiol Chemical compound SCC1=CN=CC=N1 VQFGDOHENLRPFB-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 235000020374 simple syrup Nutrition 0.000 description 3
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 description 2
- OXQOBQJCDNLAPO-UHFFFAOYSA-N 2,3-Dimethylpyrazine Chemical compound CC1=NC=CN=C1C OXQOBQJCDNLAPO-UHFFFAOYSA-N 0.000 description 2
- RJIREWQSLPRZFG-UHFFFAOYSA-N 2,5-Diethyl-3-methylpyrazine Chemical compound CCC1=CN=C(CC)C(C)=N1 RJIREWQSLPRZFG-UHFFFAOYSA-N 0.000 description 2
- ARRSOXMGLBJPNV-UHFFFAOYSA-N 2,5-Dimethyl-3-propylpyrazine Chemical compound CCCC1=NC(C)=CN=C1C ARRSOXMGLBJPNV-UHFFFAOYSA-N 0.000 description 2
- NKCSNDPVROOLKT-UHFFFAOYSA-N 2,5-dibutyl-3,6-dimethylpyrazine Chemical compound CCCCC1=NC(C)=C(CCCC)N=C1C NKCSNDPVROOLKT-UHFFFAOYSA-N 0.000 description 2
- UBPAZHYSJHMHIM-UHFFFAOYSA-N 2,5-dihexyl-3,6-dimethylpyrazine Chemical compound CCCCCCC1=NC(C)=C(CCCCCC)N=C1C UBPAZHYSJHMHIM-UHFFFAOYSA-N 0.000 description 2
- QFPSKYGXQMHPCZ-UHFFFAOYSA-N 2,5-dimethyl-3,6-bis(2-methylpropyl)pyrazine Chemical compound CC(C)CC1=NC(C)=C(CC(C)C)N=C1C QFPSKYGXQMHPCZ-UHFFFAOYSA-N 0.000 description 2
- JXTZDCLXNAWYRS-UHFFFAOYSA-N 2,5-dimethyl-3,6-di(propan-2-yl)pyrazine Chemical compound CC(C)C1=NC(C)=C(C(C)C)N=C1C JXTZDCLXNAWYRS-UHFFFAOYSA-N 0.000 description 2
- KQFKBERASRQXOG-UHFFFAOYSA-N 2,5-dimethyl-3,6-dipentylpyrazine Chemical compound CCCCCC1=NC(C)=C(CCCCC)N=C1C KQFKBERASRQXOG-UHFFFAOYSA-N 0.000 description 2
- UNTGFIAQBXNWEA-UHFFFAOYSA-N 2,5-dimethyl-3,6-dipropylpyrazine Chemical compound CCCC1=NC(C)=C(CCC)N=C1C UNTGFIAQBXNWEA-UHFFFAOYSA-N 0.000 description 2
- WWAYKGYKYHEINT-UHFFFAOYSA-N 2,5-dimethyl-3-(3-methylbutyl)pyrazine Chemical compound CC(C)CCC1=NC(C)=CN=C1C WWAYKGYKYHEINT-UHFFFAOYSA-N 0.000 description 2
- UYLKDZXJEKFFHJ-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfanylmethyl)furan Chemical compound C=1C=COC=1CSCC1=CC=CO1 UYLKDZXJEKFFHJ-UHFFFAOYSA-N 0.000 description 2
- KZXOOWGVLDEHDT-UHFFFAOYSA-N 2-Ethenyl-6-methylpyrazine Chemical compound CC1=CN=CC(C=C)=N1 KZXOOWGVLDEHDT-UHFFFAOYSA-N 0.000 description 2
- JZBCTZLGKSYRSF-UHFFFAOYSA-N 2-Ethyl-3,5-dimethylpyrazine Chemical compound CCC1=NC=C(C)N=C1C JZBCTZLGKSYRSF-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- WZHWPZQQPWKEAV-UHFFFAOYSA-N 2-chloro-3-methylpyrazine Chemical compound CC1=NC=CN=C1Cl WZHWPZQQPWKEAV-UHFFFAOYSA-N 0.000 description 2
- OXCKCFJIKRGXMM-UHFFFAOYSA-N 2-ethyl-5-methylpyrazine Chemical compound CCC1=CN=C(C)C=N1 OXCKCFJIKRGXMM-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- MRWLZECVHMHMGI-UHFFFAOYSA-N 3,5-Diethyl-2-methylpyrazine Chemical compound CCC1=CN=C(C)C(CC)=N1 MRWLZECVHMHMGI-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 229940125890 compound Ia Drugs 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- KVFIJIWMDBAGDP-UHFFFAOYSA-N ethylpyrazine Chemical compound CCC1=CN=CC=N1 KVFIJIWMDBAGDP-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 235000015243 ice cream Nutrition 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- 235000011962 puddings Nutrition 0.000 description 2
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 2
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- JMKUTMOIKCXELD-UHFFFAOYSA-N (1-Methylethenyl)pyrazine Chemical compound CC(=C)C1=CN=CC=N1 JMKUTMOIKCXELD-UHFFFAOYSA-N 0.000 description 1
- UNXOODFFHJDRBC-FPLPWBNLSA-N (3z)-3-hydroxyiminoheptan-2-one Chemical compound CCCC\C(=N\O)C(C)=O UNXOODFFHJDRBC-FPLPWBNLSA-N 0.000 description 1
- PSINWXIDJYEXLO-UHFFFAOYSA-N 2,3-Diethyl-5-methylpyrazine Chemical compound CCC1=NC=C(C)N=C1CC PSINWXIDJYEXLO-UHFFFAOYSA-N 0.000 description 1
- GZXXANJCCWGCSV-UHFFFAOYSA-N 2,3-Diethylpyrazine Chemical compound CCC1=NC=CN=C1CC GZXXANJCCWGCSV-UHFFFAOYSA-N 0.000 description 1
- OGUJUYCURMHXHG-UHFFFAOYSA-N 2,3-dimethyl-5-(3-methylbutyl)pyrazine Chemical compound CC(C)CCC1=CN=C(C)C(C)=N1 OGUJUYCURMHXHG-UHFFFAOYSA-N 0.000 description 1
- WOKWCTYNOKUPRA-UHFFFAOYSA-N 2,5-Diethyl-3,6-dimethylpyrazine Chemical compound CCC1=NC(C)=C(CC)N=C1C WOKWCTYNOKUPRA-UHFFFAOYSA-N 0.000 description 1
- VXFGCYJQMUSZGI-UHFFFAOYSA-N 2,5-dimethyl-3-methylsulfanylpyrazine Chemical compound CSC1=NC(C)=CN=C1C VXFGCYJQMUSZGI-UHFFFAOYSA-N 0.000 description 1
- ZFPJHRHCKRIEAO-UHFFFAOYSA-N 2-(2-ethylsulfanylethyl)pyrazine Chemical compound CCSCCC1=CN=CC=N1 ZFPJHRHCKRIEAO-UHFFFAOYSA-N 0.000 description 1
- NKOCMZJVIOMYFR-UHFFFAOYSA-N 2-(ethylsulfanylmethyl)pyrazine Chemical compound CCSCC1=CN=CC=N1 NKOCMZJVIOMYFR-UHFFFAOYSA-N 0.000 description 1
- RVAGIRWUMWXFKJ-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfanylmethyl)pyrazine Chemical compound C=1C=COC=1CSCC1=CN=CC=N1 RVAGIRWUMWXFKJ-UHFFFAOYSA-N 0.000 description 1
- PNGHTEYYARFCTE-UHFFFAOYSA-N 2-(methylsulfanylmethyl)pyrazine Chemical compound CSCC1=CN=CC=N1 PNGHTEYYARFCTE-UHFFFAOYSA-N 0.000 description 1
- 239000001322 2-(methylsulfanylmethyl)pyrazine Substances 0.000 description 1
- RAFHQTNQEZECFL-UHFFFAOYSA-N 2-Ethyl-6-methylpyrazine Chemical compound CCC1=CN=CC(C)=N1 RAFHQTNQEZECFL-UHFFFAOYSA-N 0.000 description 1
- ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 1
- PGTQKVQDZHXLOP-UHFFFAOYSA-N 2-Isopropyl-5-methylpyrazine Chemical compound CC(C)C1=CN=C(C)C=N1 PGTQKVQDZHXLOP-UHFFFAOYSA-N 0.000 description 1
- QNTVHLKUWSRHIO-UHFFFAOYSA-N 2-Methyl-3-vinylpyrazine Chemical compound CC1=NC=CN=C1C=C QNTVHLKUWSRHIO-UHFFFAOYSA-N 0.000 description 1
- MFPZQZZWAMAHOY-UHFFFAOYSA-N 2-Propanoylthiophene Chemical compound CCC(=O)C1=CC=CS1 MFPZQZZWAMAHOY-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- OFLSKXBALZCMCX-UHFFFAOYSA-N 2-butoxypyridine Chemical compound CCCCOC1=CC=CC=N1 OFLSKXBALZCMCX-UHFFFAOYSA-N 0.000 description 1
- LHDGCKPZCAXIBB-UHFFFAOYSA-N 2-butyl-3,5,6-trimethylpyrazine Chemical compound CCCCC1=NC(C)=C(C)N=C1C LHDGCKPZCAXIBB-UHFFFAOYSA-N 0.000 description 1
- FWENYYUEVHCZQP-UHFFFAOYSA-N 2-butyl-3-methylquinoxaline Chemical compound C1=CC=C2N=C(C)C(CCCC)=NC2=C1 FWENYYUEVHCZQP-UHFFFAOYSA-N 0.000 description 1
- GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 1
- VHDFVWCWSZQMPV-UHFFFAOYSA-N 2-ethenyl-3-ethylpyrazine Chemical compound CCC1=NC=CN=C1C=C VHDFVWCWSZQMPV-UHFFFAOYSA-N 0.000 description 1
- 239000001908 2-ethyl-5-methylpyrazine Substances 0.000 description 1
- FNTBXHXRHAFYJT-UHFFFAOYSA-N 2-ethylsulfanylpyridine Chemical compound CCSC1=CC=CC=N1 FNTBXHXRHAFYJT-UHFFFAOYSA-N 0.000 description 1
- NQYDAYMNHSBYCZ-UHFFFAOYSA-N 2-hexyl-3,5,6-trimethylpyrazine Chemical compound CCCCCCC1=NC(C)=C(C)N=C1C NQYDAYMNHSBYCZ-UHFFFAOYSA-N 0.000 description 1
- JNTPZUQXSKDCSR-UHFFFAOYSA-N 2-methyl-3-(2-methylpropyl)quinoxaline Chemical compound C1=CC=C2N=C(C)C(CC(C)C)=NC2=C1 JNTPZUQXSKDCSR-UHFFFAOYSA-N 0.000 description 1
- VLQBSKLZRSUMTJ-UHFFFAOYSA-N 2-methylsulfanylpyridine Chemical compound CSC1=CC=CC=N1 VLQBSKLZRSUMTJ-UHFFFAOYSA-N 0.000 description 1
- QKVWBAMZPUHCMO-UHFFFAOYSA-N 2-pyrazin-2-ylethanethiol Chemical compound SCCC1=CN=CC=N1 QKVWBAMZPUHCMO-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- ARBPVCYTFYHIPO-UHFFFAOYSA-N 3,6-dimethyl-1h-pyrazine-2-thione Chemical compound CC1=CN=C(C)C(=S)N1 ARBPVCYTFYHIPO-UHFFFAOYSA-N 0.000 description 1
- IEDDVCWDHHBMLW-UHFFFAOYSA-N 3-(furan-2-ylmethylsulfanyl)-2,5-dimethylpyrazine Chemical compound CC1=CN=C(C)C(SCC=2OC=CC=2)=N1 IEDDVCWDHHBMLW-UHFFFAOYSA-N 0.000 description 1
- UWJKKFNWVRAFPM-UHFFFAOYSA-N 3-butyl-2,5-dimethylpyrazine Chemical compound CCCCC1=NC(C)=CN=C1C UWJKKFNWVRAFPM-UHFFFAOYSA-N 0.000 description 1
- NNBALVIZMGWZHS-UHFFFAOYSA-N 3-chloro-2,5-dimethylpyrazine Chemical compound CC1=CN=C(C)C(Cl)=N1 NNBALVIZMGWZHS-UHFFFAOYSA-N 0.000 description 1
- KKWRXTVMYYRSMZ-UHFFFAOYSA-N 3-hydroxyimino-4-methylpentan-2-one Chemical compound CC(C)C(=NO)C(C)=O KKWRXTVMYYRSMZ-UHFFFAOYSA-N 0.000 description 1
- UUMIQEVZUUGRSH-UHFFFAOYSA-N 3-hydroxyimino-5-methylhexan-2-one Chemical compound CC(C)CC(=NO)C(C)=O UUMIQEVZUUGRSH-UHFFFAOYSA-N 0.000 description 1
- GRLLMEXCXJTHGF-UHFFFAOYSA-N 3-hydroxyiminohexan-2-one Chemical compound CCCC(=NO)C(C)=O GRLLMEXCXJTHGF-UHFFFAOYSA-N 0.000 description 1
- DCVKYISODMBDSI-UHFFFAOYSA-N 3-hydroxyiminononan-2-one Chemical compound CCCCCCC(=NO)C(C)=O DCVKYISODMBDSI-UHFFFAOYSA-N 0.000 description 1
- CVRXVGUWTKLMFD-UHFFFAOYSA-N 3-hydroxyiminooctan-2-one Chemical compound CCCCCC(=NO)C(C)=O CVRXVGUWTKLMFD-UHFFFAOYSA-N 0.000 description 1
- STLFJVQEKULVQV-UHFFFAOYSA-N 3-iodo-2,5-dimethylpyrazine Chemical compound CC1=CN=C(C)C(I)=N1 STLFJVQEKULVQV-UHFFFAOYSA-N 0.000 description 1
- GXYTVESNLKXDNK-UHFFFAOYSA-N 3-sulfanylfuran-2-carbaldehyde Chemical compound SC=1C=COC=1C=O GXYTVESNLKXDNK-UHFFFAOYSA-N 0.000 description 1
- QLFGSURDJTUOHL-UHFFFAOYSA-N 5-chloropyrazine Chemical compound ClC1=C=NC=C[N]1 QLFGSURDJTUOHL-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000012550 Pimpinella anisum Nutrition 0.000 description 1
- 240000004760 Pimpinella anisum Species 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- HAGDYFOWOREHFB-UHFFFAOYSA-N [S].C1=CN=CC=N1 Chemical class [S].C1=CN=CC=N1 HAGDYFOWOREHFB-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000008373 coffee flavor Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GHTQTHLNYUEMQK-UHFFFAOYSA-N lithium;pyrrol-1-ide Chemical compound [Li]N1C=CC=C1 GHTQTHLNYUEMQK-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- SJIIDWBFRZACDQ-UHFFFAOYSA-N pyridin-2-ylmethanethiol Chemical compound SCC1=CC=CC=N1 SJIIDWBFRZACDQ-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- OBPVWAWDKHSWNC-UHFFFAOYSA-N s-(3,6-dimethylpyrazin-2-yl) ethanethioate Chemical compound CC(=O)SC1=NC(C)=CN=C1C OBPVWAWDKHSWNC-UHFFFAOYSA-N 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 235000019220 whole milk chocolate Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Tea And Coffee (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO5181/69A NO134895C (enrdf_load_stackoverflow) | 1965-04-30 | 1969-12-31 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45234265A | 1965-04-30 | 1965-04-30 | |
| US54306966A | 1966-04-18 | 1966-04-18 | |
| NO162820A NO134889C (enrdf_load_stackoverflow) | 1965-04-30 | 1966-04-29 | |
| NO5181/69A NO134895C (enrdf_load_stackoverflow) | 1965-04-30 | 1969-12-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134895B true NO134895B (enrdf_load_stackoverflow) | 1976-09-27 |
| NO134895C NO134895C (enrdf_load_stackoverflow) | 1977-01-05 |
Family
ID=27484029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO5181/69A NO134895C (enrdf_load_stackoverflow) | 1965-04-30 | 1969-12-31 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO134895C (enrdf_load_stackoverflow) |
-
1969
- 1969-12-31 NO NO5181/69A patent/NO134895C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO134895C (enrdf_load_stackoverflow) | 1977-01-05 |
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