NO134891B - - Google Patents
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- Publication number
- NO134891B NO134891B NO1709/68A NO170968A NO134891B NO 134891 B NO134891 B NO 134891B NO 1709/68 A NO1709/68 A NO 1709/68A NO 170968 A NO170968 A NO 170968A NO 134891 B NO134891 B NO 134891B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- denotes
- coffee
- group
- prepared
- Prior art date
Links
- 239000000796 flavoring agent Substances 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 235000016213 coffee Nutrition 0.000 claims description 20
- 235000013353 coffee beverage Nutrition 0.000 claims description 20
- 235000013355 food flavoring agent Nutrition 0.000 claims description 16
- 235000021539 instant coffee Nutrition 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 235000013361 beverage Nutrition 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 20
- 240000007154 Coffea arabica Species 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 238000009835 boiling Methods 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 8
- 235000019634 flavors Nutrition 0.000 description 7
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 5
- BTBFUBUCCJKJOZ-UHFFFAOYSA-N 1-(2-Furanylmethyl)-1H-pyrrole Chemical compound C1=CC=CN1CC1=CC=CO1 BTBFUBUCCJKJOZ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- NZFLWVDXYUGFAV-UHFFFAOYSA-N 1-methyl-2-acetylpyrrole Chemical compound CC(=O)C1=CC=CN1C NZFLWVDXYUGFAV-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000020374 simple syrup Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GNFLFHZJXXFDRA-UHFFFAOYSA-N 1,2-dimethylpyrrole Chemical compound CC1=CC=CN1C GNFLFHZJXXFDRA-UHFFFAOYSA-N 0.000 description 1
- BOMRWYWTTXXRQX-UHFFFAOYSA-N 1-(1,5-dimethylpyrrol-2-yl)ethanone Chemical compound CC(=O)C1=CC=C(C)N1C BOMRWYWTTXXRQX-UHFFFAOYSA-N 0.000 description 1
- SZYIVZGXCXFXDN-UHFFFAOYSA-N 1-(1-methylpyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C=CN(C)C=1 SZYIVZGXCXFXDN-UHFFFAOYSA-N 0.000 description 1
- PYBJPTHZYBWJON-UHFFFAOYSA-N 1-(furan-2-ylmethyl)pyrrole-2-carbaldehyde Chemical compound O=CC1=CC=CN1CC1=CC=CO1 PYBJPTHZYBWJON-UHFFFAOYSA-N 0.000 description 1
- DTVPJDHHPRORAV-UHFFFAOYSA-N 1-(thiophen-2-ylmethyl)pyrrole-2-carbaldehyde Chemical compound O=CC1=CC=CN1CC1=CC=CS1 DTVPJDHHPRORAV-UHFFFAOYSA-N 0.000 description 1
- DVLGEHCERRWDIX-UHFFFAOYSA-N 1-Ethyl-1H-pyrrole-2-carboxaldehyde Chemical compound CCN1C=CC=C1C=O DVLGEHCERRWDIX-UHFFFAOYSA-N 0.000 description 1
- AYCBWOMKZDMMQR-UHFFFAOYSA-N 1-[1-(furan-2-ylmethyl)pyrrol-2-yl]ethanone Chemical compound CC(=O)C1=CC=CN1CC1=CC=CO1 AYCBWOMKZDMMQR-UHFFFAOYSA-N 0.000 description 1
- NLGTYVNFESLLTE-UHFFFAOYSA-N 1-butylpyrrole-3-carbaldehyde Chemical compound CCCCN1C=CC(C=O)=C1 NLGTYVNFESLLTE-UHFFFAOYSA-N 0.000 description 1
- VPUAYOJTHRDUTK-UHFFFAOYSA-N 1-ethylpyrrole Chemical compound CCN1C=CC=C1 VPUAYOJTHRDUTK-UHFFFAOYSA-N 0.000 description 1
- FSLCAYGKDDIJGZ-UHFFFAOYSA-N 1-methyl-2-[1-[1-(1-methylpyrrol-2-yl)ethylsulfanyl]ethyl]pyrrole Chemical compound C=1C=CN(C)C=1C(C)SC(C)C1=CC=CN1C FSLCAYGKDDIJGZ-UHFFFAOYSA-N 0.000 description 1
- ASQHVNJHHSQFLT-UHFFFAOYSA-N 1-pentan-2-ylpyrrole-2-carbaldehyde Chemical compound CCCC(C)N1C=CC=C1C=O ASQHVNJHHSQFLT-UHFFFAOYSA-N 0.000 description 1
- GASSRVLUAXPFEW-UHFFFAOYSA-N 1-pentylpyrrole-2-carbaldehyde Chemical compound CCCCCN1C=CC=C1C=O GASSRVLUAXPFEW-UHFFFAOYSA-N 0.000 description 1
- SKQQLXFCQFGFTE-UHFFFAOYSA-N 1-pentylpyrrole-3-carbaldehyde Chemical compound CCCCCN1C=CC(C=O)=C1 SKQQLXFCQFGFTE-UHFFFAOYSA-N 0.000 description 1
- GANBJDIOIDQSGI-UHFFFAOYSA-N 2-(chloromethyl)furan Chemical compound ClCC1=CC=CO1 GANBJDIOIDQSGI-UHFFFAOYSA-N 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-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
- 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
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 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
Landscapes
- Seasonings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO1709/68A NO134891C (he) | 1965-04-30 | 1968-05-02 |
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 (he) | 1965-04-30 | 1966-04-29 | |
| NO1709/68A NO134891C (he) | 1965-04-30 | 1968-05-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134891B true NO134891B (he) | 1976-09-27 |
| NO134891C NO134891C (he) | 1977-01-05 |
Family
ID=27483980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1709/68A NO134891C (he) | 1965-04-30 | 1968-05-02 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO134891C (he) |
-
1968
- 1968-05-02 NO NO1709/68A patent/NO134891C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO134891C (he) | 1977-01-05 |
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