CA1050043A - Cycloaliphatic unsaturated esters as flavour and odour agents - Google Patents
Cycloaliphatic unsaturated esters as flavour and odour agentsInfo
- Publication number
- CA1050043A CA1050043A CA220,557A CA220557A CA1050043A CA 1050043 A CA1050043 A CA 1050043A CA 220557 A CA220557 A CA 220557A CA 1050043 A CA1050043 A CA 1050043A
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- composition
- endocyclic
- formula
- dimethyl
- 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
- 239000000796 flavoring agent Substances 0.000 title claims description 39
- 150000002148 esters Chemical class 0.000 title claims description 19
- 239000003795 chemical substances by application Substances 0.000 title abstract description 9
- 235000019634 flavors Nutrition 0.000 title description 36
- 239000002304 perfume Substances 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000005466 alkylenyl group Chemical group 0.000 claims abstract description 4
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 126
- 150000001875 compounds Chemical class 0.000 claims description 50
- 235000013361 beverage Nutrition 0.000 claims description 35
- 238000002360 preparation method Methods 0.000 claims description 11
- -1 safranic acid ester Chemical class 0.000 claims description 9
- POIARNZEYGURDG-FNORWQNLSA-N beta-damascenone Chemical compound C\C=C\C(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-FNORWQNLSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 241000208125 Nicotiana Species 0.000 claims description 6
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 6
- DQULFYWMEOPFTK-UHFFFAOYSA-N ethyl 2-ethylidene-6,6-dimethylcyclohex-3-ene-1-carboxylate Chemical compound CCOC(=O)C1C(=CC)C=CCC1(C)C DQULFYWMEOPFTK-UHFFFAOYSA-N 0.000 claims description 5
- 229930007850 β-damascenone Natural products 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- BGTBFNDXYDYBEY-FNORWQNLSA-N 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one Chemical compound C\C=C\C(=O)C1=C(C)CCCC1(C)C BGTBFNDXYDYBEY-FNORWQNLSA-N 0.000 claims description 4
- DENWLZJDZOQUGW-UHFFFAOYSA-N ethyl 6,6-dimethyl-2-propylidenecyclohex-3-ene-1-carboxylate Chemical compound CCOC(=O)C1C(=CCC)C=CCC1(C)C DENWLZJDZOQUGW-UHFFFAOYSA-N 0.000 claims description 4
- 235000013355 food flavoring agent Nutrition 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- GCGZDUFEEQNVPR-UHFFFAOYSA-N 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-1-one Chemical compound CC1=CCCC(C)(C)C1C(=O)CC=C GCGZDUFEEQNVPR-UHFFFAOYSA-N 0.000 claims 1
- KEKWJMVAZROFBL-UHFFFAOYSA-N 2,6,6-trimethylcyclohexa-1,3-diene-1-carboxylic acid Chemical class CC1=C(C(O)=O)C(C)(C)CC=C1 KEKWJMVAZROFBL-UHFFFAOYSA-N 0.000 abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 38
- ZANQMOGWQBCGBN-UHFFFAOYSA-N ethyl 2,6,6-trimethylcyclohexa-2,4-diene-1-carboxylate Chemical compound CCOC(=O)C1C(C)=CC=CC1(C)C ZANQMOGWQBCGBN-UHFFFAOYSA-N 0.000 description 26
- 238000007792 addition Methods 0.000 description 19
- 235000019441 ethanol Nutrition 0.000 description 17
- 241000220225 Malus Species 0.000 description 16
- 230000004048 modification Effects 0.000 description 16
- 238000012986 modification Methods 0.000 description 16
- 240000007651 Rubus glaucus Species 0.000 description 11
- 235000011034 Rubus glaucus Nutrition 0.000 description 11
- 235000009122 Rubus idaeus Nutrition 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 241000220317 Rosa Species 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000019502 Orange oil Nutrition 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- NMGSDTSOSIPXTN-UHFFFAOYSA-N cyclohexa-1,2-diene Chemical compound C1CC=C=CC1 NMGSDTSOSIPXTN-UHFFFAOYSA-N 0.000 description 4
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- 239000010502 orange oil Substances 0.000 description 4
- 229940067107 phenylethyl alcohol Drugs 0.000 description 4
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 244000269722 Thea sinensis Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- ISAVZKCNNYFIKH-UHFFFAOYSA-N ethyl 2-ethyl-6,6-dimethyl-4-oxocyclohex-2-ene-1-carboxylate Chemical compound CCOC(=O)C1C(CC)=CC(=O)CC1(C)C ISAVZKCNNYFIKH-UHFFFAOYSA-N 0.000 description 3
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 3
- 239000001298 pelargonium graveolens oil Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000019505 tobacco product Nutrition 0.000 description 3
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (+)-β-citronellol Chemical compound OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 2
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 2
- HVGZQCSMLUDISR-UHFFFAOYSA-N 2-Phenylethyl propanoate Chemical compound CCC(=O)OCCC1=CC=CC=C1 HVGZQCSMLUDISR-UHFFFAOYSA-N 0.000 description 2
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 2
- VCHQSPDXMJAXJI-UHFFFAOYSA-N 2-o-(3,7-dimethyloct-6-enyl) 1-o-ethyl oxalate Chemical compound CCOC(=O)C(=O)OCCC(C)CCC=C(C)C VCHQSPDXMJAXJI-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- XVSZRAWFCDHCBP-UHFFFAOYSA-N 3-methylbutyl hexanoate Chemical compound CCCCCC(=O)OCCC(C)C XVSZRAWFCDHCBP-UHFFFAOYSA-N 0.000 description 2
- XKWSWANXMRXDES-UHFFFAOYSA-N 3-methylbutyl octanoate Chemical compound CCCCCCCC(=O)OCCC(C)C XKWSWANXMRXDES-UHFFFAOYSA-N 0.000 description 2
- OSMLMQQJZVENMX-UHFFFAOYSA-N 6-butyl-2,4-dimethyl-3,6-dihydro-2h-pyran Chemical compound CCCCC1OC(C)CC(C)=C1 OSMLMQQJZVENMX-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 2
- 239000005770 Eugenol Substances 0.000 description 2
- 239000005792 Geraniol Substances 0.000 description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
- DRFSOBZVMGLICQ-SGMGOOAPSA-N Guaiol acetate Chemical compound C1([C@H](CC[C@H](C2)C(C)(C)OC(C)=O)C)=C2[C@@H](C)CC1 DRFSOBZVMGLICQ-SGMGOOAPSA-N 0.000 description 2
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 2
- 241000109329 Rosa xanthina Species 0.000 description 2
- 235000004789 Rosa xanthina Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940007550 benzyl acetate Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- TVQGDYNRXLTQAP-UHFFFAOYSA-N ethyl heptanoate Chemical compound CCCCCCC(=O)OCC TVQGDYNRXLTQAP-UHFFFAOYSA-N 0.000 description 2
- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 2
- 229960002217 eugenol Drugs 0.000 description 2
- 235000021554 flavoured beverage Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 2
- 229940113087 geraniol Drugs 0.000 description 2
- 239000010648 geranium oil Substances 0.000 description 2
- 235000019717 geranium oil Nutrition 0.000 description 2
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 2
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229930002839 ionone Natural products 0.000 description 2
- 150000002499 ionone derivatives Chemical class 0.000 description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000010666 rose oil Substances 0.000 description 2
- 235000019719 rose oil Nutrition 0.000 description 2
- 229930007790 rose oxide Natural products 0.000 description 2
- 239000010668 rosemary oil Substances 0.000 description 2
- 229940058206 rosemary oil Drugs 0.000 description 2
- SGAWOGXMMPSZPB-UHFFFAOYSA-N safranal Chemical compound CC1=C(C=O)C(C)(C)CC=C1 SGAWOGXMMPSZPB-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 description 2
- 239000010678 thyme oil Substances 0.000 description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
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- 235000018285 (S)-(-)-citronellol Nutrition 0.000 description 1
- CRIGTVCBMUKRSL-FNORWQNLSA-N 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enone Chemical compound C\C=C\C(=O)C1C(C)=CCCC1(C)C CRIGTVCBMUKRSL-FNORWQNLSA-N 0.000 description 1
- LUKGUNZAFFVUIY-UHFFFAOYSA-N 1-(2-ethyl-6,6-dimethylcyclohex-2-en-1-yl)butan-1-one Chemical compound C(CCC)(=O)C1C(=CCCC1(C)C)CC LUKGUNZAFFVUIY-UHFFFAOYSA-N 0.000 description 1
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 1
- FACFHHMQICTXFZ-UHFFFAOYSA-N 2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethanamine Chemical compound N1=C2C=CC=CN2C(CCN)=C1C1=CC=CC=C1 FACFHHMQICTXFZ-UHFFFAOYSA-N 0.000 description 1
- BFDKCZMYQOSTJG-UHFFFAOYSA-N 2-[4-(trifluoromethylsulfanyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(SC(F)(F)F)C=C1 BFDKCZMYQOSTJG-UHFFFAOYSA-N 0.000 description 1
- PDGPIBIURNPBSE-UHFFFAOYSA-N 2-phenylethyl pentanoate Chemical compound CCCCC(=O)OCCC1=CC=CC=C1 PDGPIBIURNPBSE-UHFFFAOYSA-N 0.000 description 1
- PANBRUWVURLWGY-UHFFFAOYSA-N 2-undecenal Chemical compound CCCCCCCCC=CC=O PANBRUWVURLWGY-UHFFFAOYSA-N 0.000 description 1
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 1
- OGKKCSAGHUIPND-UHFFFAOYSA-N 5-methyl-1-phenylhexa-1,4-dien-3-one Chemical compound CC(C)=CC(=O)C=CC1=CC=CC=C1 OGKKCSAGHUIPND-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000717739 Boswellia sacra Species 0.000 description 1
- SGYVCFIGWBOWST-UHFFFAOYSA-N C(C=CC)(=O)C1C(CCCC1(C)C)=CC Chemical compound C(C=CC)(=O)C1C(CCCC1(C)C)=CC SGYVCFIGWBOWST-UHFFFAOYSA-N 0.000 description 1
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- 241000984090 Cistus Species 0.000 description 1
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- 241000118816 Cryptantha crassisepala Species 0.000 description 1
- 238000005773 Enders reaction Methods 0.000 description 1
- 239000001293 FEMA 3089 Substances 0.000 description 1
- 239000004863 Frankincense Substances 0.000 description 1
- 235000015164 Iris germanica var. florentina Nutrition 0.000 description 1
- 240000004101 Iris pallida Species 0.000 description 1
- 235000015265 Iris pallida Nutrition 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- 244000170064 Myrciaria floribunda Species 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- 235000011203 Origanum Nutrition 0.000 description 1
- 241001529744 Origanum Species 0.000 description 1
- LQKRYVGRPXFFAV-UHFFFAOYSA-N Phenylmethylglycidic ester Chemical compound CCOC(=O)C1OC1(C)C1=CC=CC=C1 LQKRYVGRPXFFAV-UHFFFAOYSA-N 0.000 description 1
- 240000004978 Rosa x damascena Species 0.000 description 1
- 244000178231 Rosmarinus officinalis Species 0.000 description 1
- 235000016477 Taralea oppositifolia Nutrition 0.000 description 1
- 241001358109 Taralea oppositifolia Species 0.000 description 1
- 244000125380 Terminalia tomentosa Species 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 244000158526 Thymus praecox ssp arcticus Species 0.000 description 1
- 235000005158 Thymus praecox ssp. arcticus Nutrition 0.000 description 1
- KGDJMNKPBUNHGY-RMKNXTFCSA-N [(e)-3-phenylprop-2-enyl] propanoate Chemical compound CCC(=O)OC\C=C\C1=CC=CC=C1 KGDJMNKPBUNHGY-RMKNXTFCSA-N 0.000 description 1
- 230000001944 accentuation Effects 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- JKRWZLOCPLZZEI-UHFFFAOYSA-N alpha-Trichloromethylbenzyl acetate Chemical compound CC(=O)OC(C(Cl)(Cl)Cl)C1=CC=CC=C1 JKRWZLOCPLZZEI-UHFFFAOYSA-N 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- 229940062909 amyl salicylate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 229940115397 bornyl acetate Drugs 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000010633 clary sage oil Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010636 coriander oil Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004862 elemi Substances 0.000 description 1
- NYNCZOLNVTXTTP-UHFFFAOYSA-N ethyl 2-(1,3-dioxoisoindol-2-yl)acetate Chemical compound C1=CC=C2C(=O)N(CC(=O)OCC)C(=O)C2=C1 NYNCZOLNVTXTTP-UHFFFAOYSA-N 0.000 description 1
- VETUECHAQXXHGT-UHFFFAOYSA-N ethyl 2-ethyl-6,6-dimethylcyclohexa-1,3-diene-1-carboxylate Chemical compound CCOC(=O)C1=C(CC)C=CCC1(C)C VETUECHAQXXHGT-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000001902 eugenia caryophyllata l. bud oil Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- YDZCHDQXPLJVBG-UHFFFAOYSA-N hex-1-enyl acetate Chemical compound CCCCC=COC(C)=O YDZCHDQXPLJVBG-UHFFFAOYSA-N 0.000 description 1
- OUELFZXZSSFEGX-UHFFFAOYSA-N hexan-1-ol hex-5-en-1-ol Chemical compound C(CCCC=C)O.C(CCCCC)O OUELFZXZSSFEGX-UHFFFAOYSA-N 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000001851 juniperus communis l. berry oil Substances 0.000 description 1
- 239000001748 laurus nobilis l. leaf oil Substances 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229940067137 musk ketone Drugs 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000008601 oleoresin Substances 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
- PBKYSIMDORTIEU-UHFFFAOYSA-N pentan-3-yl acetate Chemical compound CCC(CC)OC(C)=O PBKYSIMDORTIEU-UHFFFAOYSA-N 0.000 description 1
- TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 description 1
- 239000012437 perfumed product Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000017509 safranal Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 239000001962 taste-modifying agent Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- A—HUMAN NECESSITIES
- 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
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Toxicology (AREA)
- Wood Science & Technology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Manufacture Of Tobacco Products (AREA)
- Seasonings (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA311,144A CA1061097A (en) | 1974-02-22 | 1978-09-12 | Cycloaliphatic unsaturated esters as flavour and odour agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB816674A GB1456152A (en) | 1974-02-22 | 1974-02-22 | Cycloaliphatic unsaturated esters as flavou' and odour agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050043A true CA1050043A (en) | 1979-03-06 |
Family
ID=9847056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA220,557A Expired CA1050043A (en) | 1974-02-22 | 1975-02-21 | Cycloaliphatic unsaturated esters as flavour and odour agents |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5728684B2 (en, 2012) |
| BE (1) | BE825841A (en, 2012) |
| CA (1) | CA1050043A (en, 2012) |
| CH (1) | CH619140A5 (en, 2012) |
| DE (1) | DE2508059A1 (en, 2012) |
| ES (1) | ES434933A1 (en, 2012) |
| FR (2) | FR2262018B1 (en, 2012) |
| GB (1) | GB1456152A (en, 2012) |
| NL (1) | NL179474B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0056109B1 (fr) * | 1981-01-13 | 1986-01-15 | Firmenich Sa | Utilisation de 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle à titre d'ingrédient parfumant |
| JP5317190B2 (ja) * | 2009-03-09 | 2013-10-16 | 長谷川香料株式会社 | サフラン酸エチルを含有する香料素材及び香料組成物 |
| EP3102662B1 (en) * | 2014-02-04 | 2021-07-28 | Chr. Hansen A/S | Production of cider with pichia kluyveri yeast |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH549951A (fr) * | 1971-08-17 | 1974-06-14 | Firmenich & Cie | Utilisation de composes alicycliques oxygenes comme agents aromatisants. |
-
1974
- 1974-02-22 GB GB816674A patent/GB1456152A/en not_active Expired
-
1975
- 1975-02-21 CA CA220,557A patent/CA1050043A/en not_active Expired
- 1975-02-21 NL NLAANVRAGE7502124,A patent/NL179474B/xx not_active IP Right Cessation
- 1975-02-21 JP JP2108575A patent/JPS5728684B2/ja not_active Expired
- 1975-02-21 ES ES434933A patent/ES434933A1/es not_active Expired
- 1975-02-21 BE BE153617A patent/BE825841A/xx unknown
- 1975-02-21 DE DE19752508059 patent/DE2508059A1/de active Granted
- 1975-02-21 FR FR7505556A patent/FR2262018B1/fr not_active Expired
- 1975-02-21 CH CH217875A patent/CH619140A5/de not_active IP Right Cessation
-
1979
- 1979-06-21 FR FR7915993A patent/FR2427323A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL7502124A (nl) | 1975-08-26 |
| FR2262018A1 (en, 2012) | 1975-09-19 |
| ES434933A1 (es) | 1976-12-16 |
| GB1456152A (en) | 1976-11-17 |
| DE2508059A1 (de) | 1975-09-04 |
| FR2427323A1 (fr) | 1979-12-28 |
| FR2427323B1 (en, 2012) | 1981-08-14 |
| NL179474B (nl) | 1986-04-16 |
| CH619140A5 (en) | 1980-09-15 |
| JPS5728684B2 (en, 2012) | 1982-06-18 |
| DE2508059C2 (en, 2012) | 1987-05-27 |
| JPS50117946A (en, 2012) | 1975-09-16 |
| BE825841A (fr) | 1975-08-21 |
| FR2262018B1 (en, 2012) | 1982-07-02 |
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