CH563725A5 - Synthetic flavour - modifying agents for coffee and other beverages and foods - Google Patents
Synthetic flavour - modifying agents for coffee and other beverages and foodsInfo
- Publication number
- CH563725A5 CH563725A5 CH1341970A CH1341970A CH563725A5 CH 563725 A5 CH563725 A5 CH 563725A5 CH 1341970 A CH1341970 A CH 1341970A CH 1341970 A CH1341970 A CH 1341970A CH 563725 A5 CH563725 A5 CH 563725A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrazine
- methyl
- taste
- coffee
- dimethyl
- Prior art date
Links
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 19
- 235000019634 flavors Nutrition 0.000 title claims abstract description 18
- 235000013305 food Nutrition 0.000 title claims description 14
- 235000013361 beverage Nutrition 0.000 title claims description 11
- 239000003795 chemical substances by application Substances 0.000 title abstract description 5
- 235000013353 coffee beverage Nutrition 0.000 title description 25
- 235000016213 coffee Nutrition 0.000 title description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000003216 pyrazines Chemical class 0.000 claims abstract description 4
- 150000003222 pyridines Chemical class 0.000 claims abstract description 4
- -1 alkyl radicals Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000002708 enhancing effect Effects 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 235000021539 instant coffee Nutrition 0.000 abstract description 6
- 244000299461 Theobroma cacao Species 0.000 abstract description 4
- 235000009508 confectionery Nutrition 0.000 abstract description 3
- 244000269722 Thea sinensis Species 0.000 abstract description 2
- 235000009470 Theobroma cacao Nutrition 0.000 abstract description 2
- 235000013339 cereals Nutrition 0.000 abstract description 2
- 235000013312 flour Nutrition 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 235000015203 fruit juice Nutrition 0.000 abstract 1
- 150000002240 furans Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 235000013372 meat Nutrition 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 description 48
- 239000000047 product Substances 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- 240000007154 Coffea arabica Species 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- LCZUOKDVTBMCMX-UHFFFAOYSA-N 2,5-Dimethylpyrazine Chemical group CC1=CN=C(C)C=N1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000001934 2,5-dimethylpyrazine Substances 0.000 description 9
- WAVOLMBVDCRBGR-UHFFFAOYSA-N 2,5-Diethylpyrazine Chemical compound CCC1=CN=C(CC)C=N1 WAVOLMBVDCRBGR-UHFFFAOYSA-N 0.000 description 8
- LNIMMWYNSBZESE-UHFFFAOYSA-N 2-Ethyl-3-methylpyrazine, 9CI Chemical compound CCC1=NC=CN=C1C LNIMMWYNSBZESE-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- IAEGWXHKWJGQAZ-UHFFFAOYSA-N trimethylpyrazine Chemical compound CC1=CN=C(C)C(C)=N1 IAEGWXHKWJGQAZ-UHFFFAOYSA-N 0.000 description 8
- 241000723382 Corylus Species 0.000 description 7
- 235000007466 Corylus avellana Nutrition 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- HJFZAYHYIWGLNL-UHFFFAOYSA-N 2,6-Dimethylpyrazine Chemical group CC1=CN=CC(C)=N1 HJFZAYHYIWGLNL-UHFFFAOYSA-N 0.000 description 6
- WHMWOHBXYIZFPF-UHFFFAOYSA-N 2-ethyl-3,(5 or 6)-dimethylpyrazine Chemical compound CCC1=NC(C)=CN=C1C WHMWOHBXYIZFPF-UHFFFAOYSA-N 0.000 description 6
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-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
- 244000309464 bull Species 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
- 239000011701 zinc Substances 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OXQOBQJCDNLAPO-UHFFFAOYSA-N 2,3-Dimethylpyrazine Chemical compound CC1=NC=CN=C1C OXQOBQJCDNLAPO-UHFFFAOYSA-N 0.000 description 4
- RJIREWQSLPRZFG-UHFFFAOYSA-N 2,5-Diethyl-3-methylpyrazine Chemical compound CCC1=CN=C(CC)C(C)=N1 RJIREWQSLPRZFG-UHFFFAOYSA-N 0.000 description 4
- ARRSOXMGLBJPNV-UHFFFAOYSA-N 2,5-Dimethyl-3-propylpyrazine Chemical compound CCCC1=NC(C)=CN=C1C ARRSOXMGLBJPNV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QDWOWLUANUBTGE-UHFFFAOYSA-N 2,6-Diethylpyrazine Chemical compound CCC1=CN=CC(CC)=N1 QDWOWLUANUBTGE-UHFFFAOYSA-N 0.000 description 4
- KZXOOWGVLDEHDT-UHFFFAOYSA-N 2-Ethenyl-6-methylpyrazine Chemical compound CC1=CN=CC(C=C)=N1 KZXOOWGVLDEHDT-UHFFFAOYSA-N 0.000 description 4
- JZBCTZLGKSYRSF-UHFFFAOYSA-N 2-Ethyl-3,5-dimethylpyrazine Chemical compound CCC1=NC=C(C)N=C1C JZBCTZLGKSYRSF-UHFFFAOYSA-N 0.000 description 4
- JASFBLBUHWKFBZ-UHFFFAOYSA-N 2-Methyl-5-vinylpyrazine Chemical compound CC1=CN=C(C=C)C=N1 JASFBLBUHWKFBZ-UHFFFAOYSA-N 0.000 description 4
- OXCKCFJIKRGXMM-UHFFFAOYSA-N 2-ethyl-5-methylpyrazine Chemical compound CCC1=CN=C(C)C=N1 OXCKCFJIKRGXMM-UHFFFAOYSA-N 0.000 description 4
- MRWLZECVHMHMGI-UHFFFAOYSA-N 3,5-Diethyl-2-methylpyrazine Chemical compound CCC1=CN=C(C)C(CC)=N1 MRWLZECVHMHMGI-UHFFFAOYSA-N 0.000 description 4
- 235000001543 Corylus americana Nutrition 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000013736 caramel Nutrition 0.000 description 4
- KVFIJIWMDBAGDP-UHFFFAOYSA-N ethylpyrazine Chemical compound CCC1=CN=CC=N1 KVFIJIWMDBAGDP-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- GZXXANJCCWGCSV-UHFFFAOYSA-N 2,3-Diethylpyrazine Chemical compound CCC1=NC=CN=C1CC GZXXANJCCWGCSV-UHFFFAOYSA-N 0.000 description 3
- NKCSNDPVROOLKT-UHFFFAOYSA-N 2,5-dibutyl-3,6-dimethylpyrazine Chemical compound CCCCC1=NC(C)=C(CCCC)N=C1C NKCSNDPVROOLKT-UHFFFAOYSA-N 0.000 description 3
- UBPAZHYSJHMHIM-UHFFFAOYSA-N 2,5-dihexyl-3,6-dimethylpyrazine Chemical compound CCCCCCC1=NC(C)=C(CCCCCC)N=C1C UBPAZHYSJHMHIM-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- KQFKBERASRQXOG-UHFFFAOYSA-N 2,5-dimethyl-3,6-dipentylpyrazine Chemical compound CCCCCC1=NC(C)=C(CCCCC)N=C1C KQFKBERASRQXOG-UHFFFAOYSA-N 0.000 description 3
- UNTGFIAQBXNWEA-UHFFFAOYSA-N 2,5-dimethyl-3,6-dipropylpyrazine Chemical compound CCCC1=NC(C)=C(CCC)N=C1C UNTGFIAQBXNWEA-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 239000007795 chemical reaction product 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
- 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
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 230000002787 reinforcement Effects 0.000 description 3
- 235000020374 simple syrup Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JMKUTMOIKCXELD-UHFFFAOYSA-N (1-Methylethenyl)pyrazine Chemical compound CC(=C)C1=CN=CC=N1 JMKUTMOIKCXELD-UHFFFAOYSA-N 0.000 description 2
- QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical class C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 description 2
- PSINWXIDJYEXLO-UHFFFAOYSA-N 2,3-Diethyl-5-methylpyrazine Chemical compound CCC1=NC=C(C)N=C1CC PSINWXIDJYEXLO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- WOKWCTYNOKUPRA-UHFFFAOYSA-N 2,5-Diethyl-3,6-dimethylpyrazine Chemical compound CCC1=NC(C)=C(CC)N=C1C WOKWCTYNOKUPRA-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- PGTQKVQDZHXLOP-UHFFFAOYSA-N 2-Isopropyl-5-methylpyrazine Chemical compound CC(C)C1=CN=C(C)C=N1 PGTQKVQDZHXLOP-UHFFFAOYSA-N 0.000 description 2
- ZHMIODDNZRIENW-UHFFFAOYSA-N 2-Methyl-3-(2-methylpropyl)pyrazine Chemical compound CC(C)CC1=NC=CN=C1C ZHMIODDNZRIENW-UHFFFAOYSA-N 0.000 description 2
- QNTVHLKUWSRHIO-UHFFFAOYSA-N 2-Methyl-3-vinylpyrazine Chemical compound CC1=NC=CN=C1C=C QNTVHLKUWSRHIO-UHFFFAOYSA-N 0.000 description 2
- LHDGCKPZCAXIBB-UHFFFAOYSA-N 2-butyl-3,5,6-trimethylpyrazine Chemical compound CCCCC1=NC(C)=C(C)N=C1C LHDGCKPZCAXIBB-UHFFFAOYSA-N 0.000 description 2
- IRSIKJPEFMMRHD-UHFFFAOYSA-N 2-butyl-3-methylpyrazine Chemical compound CCCCC1=NC=CN=C1C IRSIKJPEFMMRHD-UHFFFAOYSA-N 0.000 description 2
- FWENYYUEVHCZQP-UHFFFAOYSA-N 2-butyl-3-methylquinoxaline Chemical compound C1=CC=C2N=C(C)C(CCCC)=NC2=C1 FWENYYUEVHCZQP-UHFFFAOYSA-N 0.000 description 2
- VHDFVWCWSZQMPV-UHFFFAOYSA-N 2-ethenyl-3-ethylpyrazine Chemical compound CCC1=NC=CN=C1C=C VHDFVWCWSZQMPV-UHFFFAOYSA-N 0.000 description 2
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- 239000001908 2-ethyl-5-methylpyrazine Substances 0.000 description 2
- NQYDAYMNHSBYCZ-UHFFFAOYSA-N 2-hexyl-3,5,6-trimethylpyrazine Chemical compound CCCCCCC1=NC(C)=C(C)N=C1C NQYDAYMNHSBYCZ-UHFFFAOYSA-N 0.000 description 2
- QPYWBTXBGYJXPF-UHFFFAOYSA-N 2-hexyl-3-methylpyrazine Chemical compound CCCCCCC1=NC=CN=C1C QPYWBTXBGYJXPF-UHFFFAOYSA-N 0.000 description 2
- QMXAEKJJOCHFOV-UHFFFAOYSA-N 2-methyl-3-pentylpyrazine Chemical compound CCCCCC1=NC=CN=C1C QMXAEKJJOCHFOV-UHFFFAOYSA-N 0.000 description 2
- LNSYLBDZKBWDNL-UHFFFAOYSA-N 2-methyl-3-propan-2-ylpyrazine Chemical compound CC(C)C1=NC=CN=C1C LNSYLBDZKBWDNL-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
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- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F5/00—Coffee; Coffee substitutes; Preparations thereof
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- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
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- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
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- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
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- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C07C45/72—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 by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/12—Ketones containing more than one keto group
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- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C—CHEMISTRY; METALLURGY
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Seasonings (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US45234265A | 1965-04-30 | 1965-04-30 | |
US54306966A | 1966-04-18 | 1966-04-18 | |
CH625166A CH529516A (de) | 1965-04-30 | 1966-04-29 | Verwendung von schwefelhaltigen Verbindungen als geschmacksverändernde Zusätze zu Nahrungsmitteln und Getränken |
Publications (1)
Publication Number | Publication Date |
---|---|
CH563725A5 true CH563725A5 (en) | 1975-07-15 |
Family
ID=27175453
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1341970A CH563725A5 (en) | 1965-04-30 | 1966-04-29 | Synthetic flavour - modifying agents for coffee and other beverages and foods |
CH1341770A CH566111A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-04-30 | 1966-04-29 | |
CH1341870A CH564317A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-04-30 | 1966-04-29 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1341770A CH566111A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-04-30 | 1966-04-29 | |
CH1341870A CH564317A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-04-30 | 1966-04-29 |
Country Status (1)
Country | Link |
---|---|
CH (3) | CH563725A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0159754A3 (en) * | 1984-04-24 | 1988-10-12 | THE PROCTER & GAMBLE COMPANY | Soluble coffee composition |
EP1384716A1 (en) * | 2002-07-25 | 2004-01-28 | Nestec S.A. | Preparation of ethenylpyrazines |
-
1966
- 1966-04-29 CH CH1341970A patent/CH563725A5/de not_active IP Right Cessation
- 1966-04-29 CH CH1341770A patent/CH566111A5/xx not_active IP Right Cessation
- 1966-04-29 CH CH1341870A patent/CH564317A5/xx not_active IP Right Cessation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0159754A3 (en) * | 1984-04-24 | 1988-10-12 | THE PROCTER & GAMBLE COMPANY | Soluble coffee composition |
EP1384716A1 (en) * | 2002-07-25 | 2004-01-28 | Nestec S.A. | Preparation of ethenylpyrazines |
Also Published As
Publication number | Publication date |
---|---|
CH564317A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-31 |
CH566111A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-15 |
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Legal Events
Date | Code | Title | Description |
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PL | Patent ceased | ||
PL | Patent ceased |