CA1108162A - Thiatetrahydrofuran-4-ones, 2-acyl-5-substitues procede e preparation et utilisation comme organoleptique - Google Patents

Thiatetrahydrofuran-4-ones, 2-acyl-5-substitues procede e preparation et utilisation comme organoleptique

Info

Publication number: CA1108162A
Authority: CA; Canada
Prior art keywords: methyl; same; hydrogen; substituted; different
Prior art date: 1977-07-28
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

Application number

CA303,418A

Other languages

English (en)

Inventor

Donald A. Withycombe

Ira Katz

Braja D. Mookherjee

Alfred E. Goossens

William J. Evers

Manfred H. Vock

Joaquin F. Vinals

Jacob Kiwala

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

International Flavors and Fragrances Inc

Original Assignee

International Flavors and Fragrances Inc

Priority date (The priority date 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 date listed.)

1977-07-28

Filing date

1978-05-16

Publication date

1981-09-01

1977-07-28 Priority claimed from US05/819,888 external-priority patent/US4092333A/en

1977-07-28 Priority claimed from US05/819,957 external-priority patent/US4092334A/en

1977-07-28 Priority claimed from US05/819,889 external-priority patent/US4096158A/en

1978-05-16 Application filed by International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc

1981-09-01 Application granted granted Critical

1981-09-01 Publication of CA1108162A publication Critical patent/CA1108162A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 39
239000001257 hydrogen Substances 0.000 claims abstract description 54
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 51
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 43
150000001875 compounds Chemical class 0.000 claims abstract description 31
239000000539 dimer Substances 0.000 claims abstract description 24
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
-1 C1-C9 alkyl Chemical group 0.000 claims abstract description 10
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
230000003190 augmentative effect Effects 0.000 claims abstract description 4
230000002708 enhancing effect Effects 0.000 claims abstract description 4
230000000447 dimerizing effect Effects 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 91
235000002637 Nicotiana tabacum Nutrition 0.000 claims description 73
238000006243 chemical reaction Methods 0.000 claims description 58
239000000796 flavoring agent Substances 0.000 claims description 58
235000019634 flavors Nutrition 0.000 claims description 57
239000000463 material Substances 0.000 claims description 42
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 29
ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 claims description 21
230000000391 smoking effect Effects 0.000 claims description 21
125000005594 diketone group Chemical group 0.000 claims description 20
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 16
235000013305 food Nutrition 0.000 claims description 13
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 12
235000015218 chewing gum Nutrition 0.000 claims description 12
229940112822 chewing gum Drugs 0.000 claims description 10
239000002671 adjuvant Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 8
XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 claims description 8
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 8
229940126601 medicinal product Drugs 0.000 claims description 8
239000000606 toothpaste Substances 0.000 claims description 8
IAEGWXHKWJGQAZ-UHFFFAOYSA-N trimethylpyrazine Chemical compound CC1=CN=C(C)C(C)=N1 IAEGWXHKWJGQAZ-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
CKOYRRWBOKMNRG-UHFFFAOYSA-N Furfuryl acetate Chemical compound CC(=O)OCC1=CC=CO1 CKOYRRWBOKMNRG-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229940034610 toothpaste Drugs 0.000 claims description 6
HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
229940043353 maltol Drugs 0.000 claims description 4
229940107700 pyruvic acid Drugs 0.000 claims description 4
HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 claims description 3
LGBXNZSSTFWRFS-UHFFFAOYSA-N 2-Furanylmethyl propanoate Chemical compound CCC(=O)OCC1=CC=CO1 LGBXNZSSTFWRFS-UHFFFAOYSA-N 0.000 claims description 3
ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 claims description 3
OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 2
239000002304 perfume Substances 0.000 claims description 2
241000208125 Nicotiana Species 0.000 claims 6
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 3
125000004432 carbon atom Chemical group C* 0.000 claims 2
241000551547 Dione <red algae> Species 0.000 claims 1
239000003599 detergent Substances 0.000 claims 1
150000002241 furanones Chemical class 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
230000000051 modifying effect Effects 0.000 claims 1
239000000344 soap Substances 0.000 claims 1
239000002904 solvent Substances 0.000 abstract description 14
235000019640 taste Nutrition 0.000 abstract description 14
239000007795 chemical reaction product Substances 0.000 abstract description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 10
150000001335 aliphatic alkanes Chemical class 0.000 abstract description 6
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 4
230000002378 acidificating effect Effects 0.000 abstract description 3
125000005350 hydroxycycloalkyl group Chemical group 0.000 abstract description 3
125000005188 oxoalkyl group Chemical group 0.000 abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
244000061176 Nicotiana tabacum Species 0.000 description 67
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 23
239000004615 ingredient Substances 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
239000000243 solution Substances 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 13
235000019504 cigarettes Nutrition 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 11
239000000341 volatile oil Substances 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
239000007788 liquid Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
235000013736 caramel Nutrition 0.000 description 9
238000009472 formulation Methods 0.000 description 9
TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical group CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
230000001055 chewing effect Effects 0.000 description 8
239000008373 coffee flavor Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
GQCBHHWLIWZIIT-UHFFFAOYSA-N 5-acetyl-2-(furan-2-ylmethylsulfanyl)-2,5-dimethyloxolan-3-one Chemical compound O1C(C(=O)C)(C)CC(=O)C1(C)SCC1=CC=CO1 GQCBHHWLIWZIIT-UHFFFAOYSA-N 0.000 description 7
108010010803 Gelatin Proteins 0.000 description 7
RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 7
235000009508 confectionery Nutrition 0.000 description 7
239000008273 gelatin Substances 0.000 description 7
229920000159 gelatin Polymers 0.000 description 7
235000019322 gelatine Nutrition 0.000 description 7
235000011852 gelatine desserts Nutrition 0.000 description 7
239000000376 reactant Substances 0.000 description 7
KVFQMAZOBTXCAZ-UHFFFAOYSA-N 3,4-Hexanedione Chemical compound CCC(=O)C(=O)CC KVFQMAZOBTXCAZ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 6
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
239000012071 phase Substances 0.000 description 6
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 5
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 5
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
235000020357 syrup Nutrition 0.000 description 5
239000006188 syrup Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
235000019505 tobacco product Nutrition 0.000 description 5
ZRKCXPIUZAYNFE-UHFFFAOYSA-N 2,5-diethyl-2,5-dimethyloxolan-3-one Chemical compound CCC1(C)CC(=O)C(C)(CC)O1 ZRKCXPIUZAYNFE-UHFFFAOYSA-N 0.000 description 4
HJFZAYHYIWGLNL-UHFFFAOYSA-N 2,6-Dimethylpyrazine Chemical compound CC1=CN=CC(C)=N1 HJFZAYHYIWGLNL-UHFFFAOYSA-N 0.000 description 4
VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 4
IGJQUJNPMOYEJY-UHFFFAOYSA-N 2-acetylpyrrole Chemical compound CC(=O)C1=CC=CN1 IGJQUJNPMOYEJY-UHFFFAOYSA-N 0.000 description 4
OACYKCIZDVVNJL-UHFFFAOYSA-N 3-Methyl-1,2-cyclopentanedione Chemical compound CC1CCC(=O)C1=O OACYKCIZDVVNJL-UHFFFAOYSA-N 0.000 description 4
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 4
DBERHVIZRVGDFO-UHFFFAOYSA-N Acetoxyacetone Chemical compound CC(=O)COC(C)=O DBERHVIZRVGDFO-UHFFFAOYSA-N 0.000 description 4
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 4
235000001453 Glycyrrhiza echinata Nutrition 0.000 description 4
235000006200 Glycyrrhiza glabra Nutrition 0.000 description 4
235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
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 4
229930006000 Sucrose Natural products 0.000 description 4
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
235000009470 Theobroma cacao Nutrition 0.000 description 4
244000299461 Theobroma cacao Species 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000006471 dimerization reaction Methods 0.000 description 4
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-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
238000010438 heat treatment Methods 0.000 description 4
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 4
229940010454 licorice Drugs 0.000 description 4
CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
230000005923 long-lasting effect Effects 0.000 description 4
CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 4
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 4
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000005720 sucrose Substances 0.000 description 4
UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
229940088594 vitamin Drugs 0.000 description 4
229930003231 vitamin Natural products 0.000 description 4
235000013343 vitamin Nutrition 0.000 description 4
239000011782 vitamin Substances 0.000 description 4
LFWLUDLUCDRDAF-UHFFFAOYSA-N 5-methyl-1h-pyrrole-2-carbaldehyde Chemical compound CC1=CC=C(C=O)N1 LFWLUDLUCDRDAF-UHFFFAOYSA-N 0.000 description 3
244000215068 Acacia senegal Species 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 3
240000004670 Glycyrrhiza echinata Species 0.000 description 3
229920000084 Gum arabic Polymers 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
235000003228 Lactuca sativa Nutrition 0.000 description 3
240000008415 Lactuca sativa Species 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
235000010489 acacia gum Nutrition 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
235000019568 aromas Nutrition 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
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239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
235000019155 vitamin A Nutrition 0.000 description 1
239000011719 vitamin A Substances 0.000 description 1
235000019164 vitamin B2 Nutrition 0.000 description 1
239000011716 vitamin B2 Substances 0.000 description 1
235000019158 vitamin B6 Nutrition 0.000 description 1
239000011726 vitamin B6 Substances 0.000 description 1
235000019166 vitamin D Nutrition 0.000 description 1
239000011710 vitamin D Substances 0.000 description 1
150000003710 vitamin D derivatives Chemical class 0.000 description 1
229940045997 vitamin a Drugs 0.000 description 1
229940011671 vitamin b6 Drugs 0.000 description 1
229940046008 vitamin d Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
229930007850 β-damascenone Natural products 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen 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
- A23L27/205—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
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
- A24B15/406—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms in a five-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/64—Sulfur atoms
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Polymers & Plastics (AREA)
Food Science & Technology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Nutrition Science (AREA)
Toxicology (AREA)
General Chemical & Material Sciences (AREA)
Fats And Perfumes (AREA)
Seasonings (AREA)
Confectionery (AREA)
Manufacture Of Tobacco Products (AREA)
Furan Compounds (AREA)

CA303,418A 1977-07-28 1978-05-16 Thiatetrahydrofuran-4-ones, 2-acyl-5-substitues procede e preparation et utilisation comme organoleptique Expired CA1108162A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US05/819,888 US4092333A (en)	1977-07-28	1977-07-28	2-Acyl-5-substituted thiatetrahydrofuran-4-ones
US819,889		1977-07-28
US819,888		1977-07-28
US05/819,957 US4092334A (en)	1977-07-28	1977-07-28	5-Acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones
US05/819,889 US4096158A (en)	1977-07-28	1977-07-28	Process for preparing 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones
US819,957		1986-01-12

Publications (1)

Publication Number	Publication Date
CA1108162A true CA1108162A (fr)	1981-09-01

Family

ID=27420134

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA303,418A Expired CA1108162A (fr)	1977-07-28	1978-05-16	Thiatetrahydrofuran-4-ones, 2-acyl-5-substitues procede e preparation et utilisation comme organoleptique

Country Status (3)

Country	Link
JP (1)	JPS5424866A (fr)
CA (1)	CA1108162A (fr)
GB (1)	GB1603392A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9034106B2 (en) *	2010-03-26	2015-05-19	Philip Morris Usa Inc.	Smoking article including alkanoylated glycoside
JP7648351B2 (ja) *	2020-08-26	2025-03-18	日本たばこ産業株式会社	たばこ充填材およびたばこ製品

1978
- 1978-05-16 CA CA303,418A patent/CA1108162A/fr not_active Expired
- 1978-05-25 GB GB22793/78A patent/GB1603392A/en not_active Expired
- 1978-07-07 JP JP8349378A patent/JPS5424866A/ja active Pending

Also Published As

Publication number	Publication date
GB1603392A (en)	1981-11-25
JPS5424866A (en)	1979-02-24

Legal Events

Date	Code	Title	Description
1998-09-01	MKEX	Expiry

Publication	Publication Date	Title
US4126708A (en)	1978-11-21	Flavoring with 2-acyl-5-substituted thiatetrahydrofuran-4-ones
US3879425A (en)	1975-04-22	Ethylene acetal of 3-phenyl-4-pentenal
US4096158A (en)	1978-06-20	Process for preparing 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones
US3716543A (en)	1973-02-13	C10-c13 hydrocarbyl substituted pyridine compounds
US3914227A (en)	1975-10-21	Certain cycloalkyl pyrazinyl ketones
US4143173A (en)	1979-03-06	Flavoring with 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones
US4010286A (en)	1977-03-01	Flavoring with 4-methyl-1-oxaspiro[5.5]undecane
US4084009A (en)	1978-04-11	Flavoring with a hydroxy cyclohexenone derivative
US4093752A (en)	1978-06-06	Flavoring with 2,4,6-triisobutyl-1,3,5-trioxane
US4070491A (en)	1978-01-24	2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the organoleptic properties of foodstuffs and tobacco using one or more of said pyrans
CA1108162A (fr)	1981-09-01	Thiatetrahydrofuran-4-ones, 2-acyl-5-substitues procede e preparation et utilisation comme organoleptique
US3928645A (en)	1975-12-23	Enhancing red-berry flavor with 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butanone and 4-(6,6-dimethyl-2-methylene-3-cyclohexen-1-yl)-2-butanone
US3917870A (en)	1975-11-04	Enhancing grape flavor with 2-phenyl-3-carboethoxyfuran and bis (cyclohexyl) disulfide
US4031140A (en)	1977-06-21	4- AND 5-Phenyl pentenal acetals
US3862340A (en)	1975-01-21	Flavoring with 5-phenyl pentenals
US4170236A (en)	1979-10-09	Isobutyl substituted heterocyclic compounds and uses for augmenting or enhancing the organoleptic properties of smoking compositions
US4191785A (en)	1980-03-04	Flavoring with mixtures of 2,4,6-triisobutyl-1,3,5-trioxane and 2-isobutyl-dialkyl oxazolines
US4115406A (en)	1978-09-19	2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the organoleptic properties of foodstuffs and tobacco using one or more of said pyrans
US4192782A (en)	1980-03-11	Use of certain spiropyran derivatives for augmenting, enhancing or modifying the organoleptic properties of perfumes and colognes
US4036886A (en)	1977-07-19	Processes for producing 4- and 5-phenyl pentenals
US4186103A (en)	1980-01-29	Use of spiropyran derivatives in augmenting, enhancing or modifying the aroma of detergents
US4240447A (en)	1980-12-23	Use for preparing smoking tobacco compositions of spiropyran derivatives
US4207905A (en)	1980-06-17	Isobutyl substituted heterocyclic compounds for augmenting or enhancing the organoleptic properties of smoking tobaccos and smoking tobacco articles
US4157350A (en)	1979-06-05	Process for preparing 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione and intermediates
US3898283A (en)	1975-08-05	Novel chemical intermediates used in producing 4- and 5-phenyl-pentenals