DE2338848A1 - Phenylpentenale und diese enthaltende materialien - Google Patents
Phenylpentenale und diese enthaltende materialienInfo
- Publication number
- DE2338848A1 DE2338848A1 DE19732338848 DE2338848A DE2338848A1 DE 2338848 A1 DE2338848 A1 DE 2338848A1 DE 19732338848 DE19732338848 DE 19732338848 DE 2338848 A DE2338848 A DE 2338848A DE 2338848 A1 DE2338848 A1 DE 2338848A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- pentenal
- acetal
- carbon
- hydrogen
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims description 59
- YPAJRUMMODCONM-UHFFFAOYSA-N 2-Phenyl-2-pentenal Chemical compound CCC=C(C=O)C1=CC=CC=C1 YPAJRUMMODCONM-UHFFFAOYSA-N 0.000 title claims description 19
- -1 thiazole 2 (n-pentyl) thiazole Chemical compound 0.000 claims description 160
- 239000000203 mixture Substances 0.000 claims description 137
- 239000000796 flavoring agent Substances 0.000 claims description 95
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 94
- 235000019634 flavors Nutrition 0.000 claims description 93
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 88
- 235000019640 taste Nutrition 0.000 claims description 88
- 150000001241 acetals Chemical class 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
- 238000002360 preparation method Methods 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 235000019441 ethanol Nutrition 0.000 claims description 45
- 235000013305 food Nutrition 0.000 claims description 41
- PBWQZEMADHTUIF-UHFFFAOYSA-N 2-phenylpent-4-enal Chemical compound C=CCC(C=O)C1=CC=CC=C1 PBWQZEMADHTUIF-UHFFFAOYSA-N 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 29
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 28
- 230000000391 smoking effect Effects 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000002304 perfume Substances 0.000 claims description 26
- DTCCTIQRPGSLPT-UHFFFAOYSA-N beta-Aethyl-acrolein Natural products CCC=CC=O DTCCTIQRPGSLPT-UHFFFAOYSA-N 0.000 claims description 24
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 23
- 240000003768 Solanum lycopersicum Species 0.000 claims description 23
- XYUWGADPPOLCNU-UHFFFAOYSA-N 3-phenylpent-2-enal Chemical compound O=CC=C(CC)C1=CC=CC=C1 XYUWGADPPOLCNU-UHFFFAOYSA-N 0.000 claims description 21
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- 239000003205 fragrance Substances 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 18
- DCEMFJJXTBOOAO-QHHAFSJGSA-N (e)-5-phenylpent-2-enal Chemical compound O=C\C=C\CCC1=CC=CC=C1 DCEMFJJXTBOOAO-QHHAFSJGSA-N 0.000 claims description 16
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 16
- 239000004615 ingredient Substances 0.000 claims description 16
- 235000019505 tobacco product Nutrition 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- XQTAGXUFCZLHIQ-UHFFFAOYSA-N 3-Phenyl-4-pentenal Chemical compound O=CCC(C=C)C1=CC=CC=C1 XQTAGXUFCZLHIQ-UHFFFAOYSA-N 0.000 claims description 13
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 235000013355 food flavoring agent Nutrition 0.000 claims description 11
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 10
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 claims description 10
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 10
- 229940043353 maltol Drugs 0.000 claims description 10
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910003002 lithium salt Inorganic materials 0.000 claims description 9
- 159000000002 lithium salts Chemical class 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 9
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 9
- 235000012141 vanillin Nutrition 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229940067107 phenylethyl alcohol Drugs 0.000 claims description 8
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 7
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 7
- QURFFFCYNQXLCU-UHFFFAOYSA-N Pentyl 3-methylbutanoate Chemical compound CCCCCOC(=O)CC(C)C QURFFFCYNQXLCU-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 6
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims description 5
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 229940043350 citral Drugs 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 5
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims description 5
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000344 soap Substances 0.000 claims description 5
- YURDCJXYOLERLO-LCYFTJDESA-N (2E)-5-methyl-2-phenylhex-2-enal Chemical compound CC(C)C\C=C(\C=O)C1=CC=CC=C1 YURDCJXYOLERLO-LCYFTJDESA-N 0.000 claims description 4
- NRBHDAVENYHNHY-UHFFFAOYSA-N 1,1-dimethoxypent-4-en-2-ylbenzene Chemical compound COC(OC)C(CC=C)C1=CC=CC=C1 NRBHDAVENYHNHY-UHFFFAOYSA-N 0.000 claims description 4
- CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 claims description 4
- CMPVUVUNJQERIT-UHFFFAOYSA-N 2-isobutylthiazole Chemical compound CC(C)CC1=NC=CS1 CMPVUVUNJQERIT-UHFFFAOYSA-N 0.000 claims description 4
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 claims description 4
- ZIJQBRWQRGNPAP-UHFFFAOYSA-N 5,5-dimethoxypent-1-en-3-ylbenzene Chemical compound COC(OC)CC(C=C)C1=CC=CC=C1 ZIJQBRWQRGNPAP-UHFFFAOYSA-N 0.000 claims description 4
- YURDCJXYOLERLO-UHFFFAOYSA-N 5-Methyl-2-phenyl-2-hexenal Natural products CC(C)CC=C(C=O)C1=CC=CC=C1 YURDCJXYOLERLO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002781 deodorant agent Substances 0.000 claims description 4
- 239000003599 detergent Substances 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- CFNJLPHOBMVMNS-UHFFFAOYSA-N pentyl butyrate Chemical compound CCCCCOC(=O)CCC CFNJLPHOBMVMNS-UHFFFAOYSA-N 0.000 claims description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims description 4
- MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 claims description 3
- ULRYRAHIBWLZKC-XYOKQWHBSA-N (2Z)-4-Methyl-2-phenyl-2-pentenal Chemical compound CC(C)\C=C(/C=O)C1=CC=CC=C1 ULRYRAHIBWLZKC-XYOKQWHBSA-N 0.000 claims description 3
- RUROFEVDCUGKHD-UHFFFAOYSA-N 3-bromoprop-1-enylbenzene Chemical compound BrCC=CC1=CC=CC=C1 RUROFEVDCUGKHD-UHFFFAOYSA-N 0.000 claims description 3
- RJRBLBXGWOVSBQ-UHFFFAOYSA-N 5,5-diethoxypent-1-en-3-ylbenzene Chemical compound CCOC(OCC)CC(C=C)C1=CC=CC=C1 RJRBLBXGWOVSBQ-UHFFFAOYSA-N 0.000 claims description 3
- AYWJSCLAAPJZEF-UHFFFAOYSA-N Butyl 3-methylbutanoate Chemical compound CCCCOC(=O)CC(C)C AYWJSCLAAPJZEF-UHFFFAOYSA-N 0.000 claims description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims description 2
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 claims description 2
- ICSFEGRQBPWRJB-UHFFFAOYSA-N 3-phenylpent-3-enal Chemical compound O=CCC(=CC)C1=CC=CC=C1 ICSFEGRQBPWRJB-UHFFFAOYSA-N 0.000 claims description 2
- QUMXDOLUJCHOAY-UHFFFAOYSA-N alpha-methylbenzyl acetate Natural products CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 claims description 2
- MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 claims description 2
- 241000208125 Nicotiana Species 0.000 claims 2
- FINHMKGKINIASC-UHFFFAOYSA-N Tetramethylpyrazine Chemical compound CC1=NC(C)=C(C)N=C1C FINHMKGKINIASC-UHFFFAOYSA-N 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- CQCAYWAIRTVXIY-UHFFFAOYSA-N 2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC=O)C1=CC=CC=C1 CQCAYWAIRTVXIY-UHFFFAOYSA-N 0.000 claims 1
- RCSBILYQLVXLJG-UHFFFAOYSA-N 2-Propenyl hexanoate Chemical compound CCCCCC(=O)OCC=C RCSBILYQLVXLJG-UHFFFAOYSA-N 0.000 claims 1
- CKJGUVNPOIXVAP-UHFFFAOYSA-N 2-phosphanylideneacetaldehyde Chemical class O=CC=P CKJGUVNPOIXVAP-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000001649 bromium compounds Chemical class 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 235000013573 potato product Nutrition 0.000 claims 1
- 244000061176 Nicotiana tabacum Species 0.000 description 86
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 80
- 238000006243 chemical reaction Methods 0.000 description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 36
- 235000017803 cinnamon Nutrition 0.000 description 36
- 244000299461 Theobroma cacao Species 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- 150000001299 aldehydes Chemical class 0.000 description 27
- 239000003921 oil Substances 0.000 description 27
- 235000019198 oils Nutrition 0.000 description 27
- 235000009470 Theobroma cacao Nutrition 0.000 description 24
- 239000002585 base Substances 0.000 description 22
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 235000009508 confectionery Nutrition 0.000 description 20
- 239000007787 solid Substances 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 15
- 235000013311 vegetables Nutrition 0.000 description 15
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 14
- 150000001336 alkenes Chemical group 0.000 description 13
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 13
- 235000014347 soups Nutrition 0.000 description 13
- DTCCTIQRPGSLPT-ONEGZZNKSA-N (E)-2-pentenal Chemical compound CC\C=C\C=O DTCCTIQRPGSLPT-ONEGZZNKSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 12
- 239000012346 acetyl chloride Substances 0.000 description 12
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- KFYPPNXDGOVEDR-UHFFFAOYSA-N 4-phenylpent-4-enal Chemical compound O=CCCC(=C)C1=CC=CC=C1 KFYPPNXDGOVEDR-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 11
- 235000019219 chocolate Nutrition 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 230000002378 acidificating effect Effects 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- AVKOGSJSRXORKB-UHFFFAOYSA-N 4-phenylpent-2-enal Chemical compound O=CC=CC(C)C1=CC=CC=C1 AVKOGSJSRXORKB-UHFFFAOYSA-N 0.000 description 9
- 239000002262 Schiff base Substances 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- BHUURXZEJNOOBQ-WEVVVXLNSA-N (e)-5-phenylpent-4-enal Chemical compound O=CCC\C=C\C1=CC=CC=C1 BHUURXZEJNOOBQ-WEVVVXLNSA-N 0.000 description 8
- 150000004753 Schiff bases Chemical class 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 150000002081 enamines Chemical class 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- DCEMFJJXTBOOAO-UHFFFAOYSA-N 5-phenylpent-2-enal Chemical class O=CC=CCCC1=CC=CC=C1 DCEMFJJXTBOOAO-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 235000002595 Solanum tuberosum Nutrition 0.000 description 6
- 244000061456 Solanum tuberosum Species 0.000 description 6
- 241000219793 Trifolium Species 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 235000019504 cigarettes Nutrition 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 229940100595 phenylacetaldehyde Drugs 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- 235000019220 whole milk chocolate Nutrition 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 235000019506 cigar Nutrition 0.000 description 5
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 5
- 235000020971 citrus fruits Nutrition 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 235000021056 liquid food Nutrition 0.000 description 5
- 239000001627 myristica fragrans houtt. fruit oil Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Inorganic materials [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 5
- 235000013599 spices Nutrition 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 5
- 235000020234 walnut Nutrition 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- GTDCDFKGLIWDJX-UHFFFAOYSA-N 4-phenylpent-3-enal Chemical compound O=CCC=C(C)C1=CC=CC=C1 GTDCDFKGLIWDJX-UHFFFAOYSA-N 0.000 description 4
- GKGWRZZDWNGZGR-UHFFFAOYSA-N 5-methyl-2-(4-methylphenyl)hex-2-enal Chemical compound CC(CC=C(C=O)C1=CC=C(C=C1)C)C GKGWRZZDWNGZGR-UHFFFAOYSA-N 0.000 description 4
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000016068 Berberis vulgaris Nutrition 0.000 description 4
- 241000335053 Beta vulgaris Species 0.000 description 4
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Classifications
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- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- 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
- A23L27/204—Aromatic compounds
-
- 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
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
-
- 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
-
- 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
- A24B15/301—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—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
- C07C45/67—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
- C07C45/68—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
- C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- General Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Fats And Perfumes (AREA)
- Confectionery (AREA)
- Fish Paste Products (AREA)
- Manufacture Of Tobacco Products (AREA)
- Seasonings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27692272A | 1972-08-01 | 1972-08-01 | |
| US00276921A US3805804A (en) | 1972-08-01 | 1972-08-01 | Method of improved tobacco product containing phenyl-pentenals |
| US283632A US3862340A (en) | 1972-08-25 | 1972-08-25 | Flavoring with 5-phenyl pentenals |
| US00283651A US3852482A (en) | 1972-08-25 | 1972-08-25 | Process of altering the flavor of a tomato soup mix with 2-phenyl-4-pentenal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2338848A1 true DE2338848A1 (de) | 1974-02-14 |
Family
ID=27501177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732338848 Pending DE2338848A1 (de) | 1972-08-01 | 1973-07-31 | Phenylpentenale und diese enthaltende materialien |
Country Status (8)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3004661A1 (de) * | 1980-02-08 | 1981-08-13 | Henkel KGaA, 4000 Düsseldorf | Verwendung alkylsubstituierter 1,3-dioxolane als riechstoffe, sowie diese enthaltende riechstoffkompositionen |
| CN112710743B (zh) * | 2020-10-29 | 2022-08-19 | 山东海科新源材料科技股份有限公司 | 碳酸酯溶剂中杂质的分离与检测方法及其应用 |
-
1973
- 1973-07-17 AU AU58187/73A patent/AU469154B2/en not_active Expired
- 1973-07-26 GB GB3564373A patent/GB1437018A/en not_active Expired
- 1973-07-30 IT IT51715/73A patent/IT1047923B/it active
- 1973-07-30 NL NL7310549A patent/NL7310549A/xx not_active Application Discontinuation
- 1973-07-30 CH CH1109473A patent/CH583526A5/xx not_active IP Right Cessation
- 1973-07-31 DE DE19732338848 patent/DE2338848A1/de active Pending
- 1973-08-01 JP JP48086695A patent/JPS4980277A/ja active Pending
- 1973-08-01 FR FR7328261A patent/FR2225102A1/fr not_active Withdrawn
-
1974
- 1974-08-22 FR FR7428898A patent/FR2241263A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT1047923B (it) | 1980-10-20 |
| NL7310549A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-05 |
| GB1437018A (en) | 1976-05-26 |
| FR2241263A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-03-21 |
| FR2225102A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-11-08 |
| CH583526A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-01-14 |
| AU469154B2 (en) | 1976-02-05 |
| JPS4980277A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-08-02 |
| AU5818773A (en) | 1975-01-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |