US3887603A - Menthol-release compounds - Google Patents
Menthol-release compounds Download PDFInfo
- Publication number
- US3887603A US3887603A US384048A US38404873A US3887603A US 3887603 A US3887603 A US 3887603A US 384048 A US384048 A US 384048A US 38404873 A US38404873 A US 38404873A US 3887603 A US3887603 A US 3887603A
- Authority
- US
- United States
- Prior art keywords
- menthol
- menthyl
- column
- read
- carbonate
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 title abstract description 68
- 229940041616 menthol Drugs 0.000 title abstract description 66
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 title abstract description 65
- 239000000126 substance Substances 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 abstract description 25
- 239000000178 monomer Substances 0.000 abstract description 21
- 239000003795 chemical substances by application Substances 0.000 abstract description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 18
- 230000000391 smoking effect Effects 0.000 abstract description 15
- 239000000796 flavoring agent Substances 0.000 abstract description 11
- 235000019634 flavors Nutrition 0.000 abstract description 10
- 125000002723 alicyclic group Chemical group 0.000 abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 abstract description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract description 7
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 241000208125 Nicotiana Species 0.000 description 34
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000779 smoke Substances 0.000 description 13
- -1 carbonate ester Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000004342 Benzoyl peroxide Substances 0.000 description 8
- 235000019400 benzoyl peroxide Nutrition 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000012937 correction Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000000197 pyrolysis Methods 0.000 description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 230000009965 odorless effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QPJULHNSANGKPH-UHFFFAOYSA-N 2-methyl-3-phenylhex-5-en-3-ol Chemical compound C=CCC(O)(C(C)C)C1=CC=CC=C1 QPJULHNSANGKPH-UHFFFAOYSA-N 0.000 description 2
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 244000131522 Citrus pyriformis Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000000935 solvent evaporation Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000019505 tobacco product Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WWJLTUYUCTYFGG-UHFFFAOYSA-N (1-methyl-4-propan-2-ylcyclohexyl) carbonochloridate Chemical compound CC(C)C1CCC(C)(OC(Cl)=O)CC1 WWJLTUYUCTYFGG-UHFFFAOYSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- BELRNEPYFJNSPN-UHFFFAOYSA-N 2-phenylpent-4-en-2-ol Chemical compound C=CCC(O)(C)C1=CC=CC=C1 BELRNEPYFJNSPN-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- NHEPUTZWBISVJH-UHFFFAOYSA-N 3-methylhept-6-en-3-ol Chemical compound CCC(C)(O)CCC=C NHEPUTZWBISVJH-UHFFFAOYSA-N 0.000 description 1
- RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- RXOKYEACVSJHAW-UHFFFAOYSA-N CC(CC=COC(O)=O)C1=CC=CC=C1 Chemical compound CC(CC=COC(O)=O)C1=CC=CC=C1 RXOKYEACVSJHAW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 101100042848 Rattus norvegicus Smok gene Proteins 0.000 description 1
- 241001464377 Resia Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- QFEHNMKROHXPFO-GTYQWKCWSA-N bis[(1s,2r,5s)-5-methyl-2-propan-2-ylcyclohexyl] carbonate Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(=O)O[C@@H]1[C@@H](C(C)C)CC[C@H](C)C1 QFEHNMKROHXPFO-GTYQWKCWSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- HFNQLYDPNAZRCH-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O.OC(O)=O HFNQLYDPNAZRCH-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
Definitions
- the present polymeric, menthol-release agents may vary greatly in molecular weight.
- the number of monomeric units may range from 2 to 100 yielding molecular weights of from about 550 to 30,000. All such polymers are useful within the scope of this invention, however, it is preferred that polymerization be controlled through modification of the catalyst concentration, temperature, time of reaction, etc. in order to obtain reaction products having from about 6 to about 40 monomeric units or molecular weights of from about 1600 to about 12,000.
- Theidistilled 8116, 120 mole was added Via a Syringe to the product showed a yield of 77 percent and possessed a cold, stirred solution over a period of 10 minutes. An boilingpoint in the range 67 80C at 20 mm which is evolution Of butane was noted during the addition. The the and pressure given cologne and Clerc lemon yellow solution was then stirred at room temper- Soc hi France, 195 5 836 f hi compound 1R ature for 2 hours. Because the gas evolution had not d NMR d h d a pure product ceased, the solution was warmed to about C and 35 Carbonate held there for 45 minutes.
- Fraction 4 subjected to NMR analysis showed a 45 to 50 percent content of the mixed menthyl methylphenylbutenyl carbonate. Its odor was light and pleasant but non-menthol-like. On heating it gave a menthol odor.
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Manufacture Of Tobacco Products (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US384048A US3887603A (en) | 1973-07-30 | 1973-07-30 | Menthol-release compounds |
| CA203,842A CA1051453A (en) | 1973-07-30 | 1974-07-02 | Menthol-release compounds |
| AU70895/74A AU486017B2 (en) | 1973-07-30 | 1974-07-05 | Menthol-release compounds |
| NL7409553A NL7409553A (nl) | 1973-07-30 | 1974-07-15 | Menthol ontwikkelende stoffen. |
| GB3117874A GB1444295A (en) | 1973-07-30 | 1974-07-15 | Menthol-release compounds |
| JP49080829A JPS5230509B2 (de) | 1973-07-30 | 1974-07-16 | |
| SU742052277A SU650481A3 (ru) | 1973-07-30 | 1974-07-29 | Способ получени полимерного соединени ,выдел ющего ментол |
| DE2436472A DE2436472B2 (de) | 1973-07-30 | 1974-07-29 | Kohlensäure-alkenyl-menthylester-Oligomere und -Polymere sowie diese enthaltendes Tabakerzeugnis |
| CH1048974A CH593635A5 (de) | 1973-07-30 | 1974-07-30 | |
| US05/559,574 US4002179A (en) | 1973-07-30 | 1975-03-18 | Smoking compositions incorporating a menthol-release agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US384048A US3887603A (en) | 1973-07-30 | 1973-07-30 | Menthol-release compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/559,574 Division US4002179A (en) | 1973-07-30 | 1975-03-18 | Smoking compositions incorporating a menthol-release agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3887603A true US3887603A (en) | 1975-06-03 |
Family
ID=23515813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US384048A Expired - Lifetime US3887603A (en) | 1973-07-30 | 1973-07-30 | Menthol-release compounds |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3887603A (de) |
| JP (1) | JPS5230509B2 (de) |
| CA (1) | CA1051453A (de) |
| CH (1) | CH593635A5 (de) |
| DE (1) | DE2436472B2 (de) |
| GB (1) | GB1444295A (de) |
| NL (1) | NL7409553A (de) |
| SU (1) | SU650481A3 (de) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119106A (en) * | 1975-10-22 | 1978-10-10 | Philip Morris, Incorporated | Flavorant-release resin compositions |
| US4125484A (en) * | 1976-02-27 | 1978-11-14 | Shell Oil Company | Tertiary alcohols |
| US4912253A (en) * | 1988-06-06 | 1990-03-27 | Shin-Etsu Chemical Co., Ltd. | Method for the preparation of an unsaturated alcohol or ester thereof |
| US5098886A (en) * | 1991-03-17 | 1992-03-24 | Narula Anubhav P S | Substituted and unsubstituted alkyl cyclohexylmenthyl and cyclohexenylmethyl carbonates and perfumery uses thereof |
| US20030192562A1 (en) * | 2000-11-06 | 2003-10-16 | Nobukazu Higashi | Tobacco odor deodorizing perfume composition, tobacco odor deodorant, cigarette low in sidestream smoke odor, and tobacco package |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5614453Y2 (de) * | 1975-10-21 | 1981-04-04 | ||
| JPS53160566U (de) * | 1977-05-23 | 1978-12-15 | ||
| JPS6312275Y2 (de) * | 1979-03-28 | 1988-04-08 | ||
| US8632792B2 (en) * | 2008-04-01 | 2014-01-21 | Takasago International Corporation | Cooling sensation agent composition and sensory stimulation agent composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419543A (en) * | 1964-10-01 | 1968-12-31 | Liggett & Myers Inc | Carbonate esters of flavorants |
-
1973
- 1973-07-30 US US384048A patent/US3887603A/en not_active Expired - Lifetime
-
1974
- 1974-07-02 CA CA203,842A patent/CA1051453A/en not_active Expired
- 1974-07-15 GB GB3117874A patent/GB1444295A/en not_active Expired
- 1974-07-15 NL NL7409553A patent/NL7409553A/xx not_active Application Discontinuation
- 1974-07-16 JP JP49080829A patent/JPS5230509B2/ja not_active Expired
- 1974-07-29 DE DE2436472A patent/DE2436472B2/de active Granted
- 1974-07-29 SU SU742052277A patent/SU650481A3/ru active
- 1974-07-30 CH CH1048974A patent/CH593635A5/xx not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419543A (en) * | 1964-10-01 | 1968-12-31 | Liggett & Myers Inc | Carbonate esters of flavorants |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119106A (en) * | 1975-10-22 | 1978-10-10 | Philip Morris, Incorporated | Flavorant-release resin compositions |
| US4127601A (en) * | 1975-10-22 | 1978-11-28 | Philip Morris, Incorporated | α-Substituted vinyl menthyl carbonates |
| US4125484A (en) * | 1976-02-27 | 1978-11-14 | Shell Oil Company | Tertiary alcohols |
| US4912253A (en) * | 1988-06-06 | 1990-03-27 | Shin-Etsu Chemical Co., Ltd. | Method for the preparation of an unsaturated alcohol or ester thereof |
| US5098886A (en) * | 1991-03-17 | 1992-03-24 | Narula Anubhav P S | Substituted and unsubstituted alkyl cyclohexylmenthyl and cyclohexenylmethyl carbonates and perfumery uses thereof |
| US20030192562A1 (en) * | 2000-11-06 | 2003-10-16 | Nobukazu Higashi | Tobacco odor deodorizing perfume composition, tobacco odor deodorant, cigarette low in sidestream smoke odor, and tobacco package |
| US7481891B2 (en) * | 2000-11-06 | 2009-01-27 | Japan Tobacco Inc. | Cigarette wrapper consisting of mandarin orange essential oil |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2436472B2 (de) | 1979-11-29 |
| GB1444295A (en) | 1976-07-28 |
| AU7089574A (en) | 1976-01-08 |
| SU650481A3 (ru) | 1979-02-28 |
| NL7409553A (nl) | 1975-02-03 |
| CA1051453A (en) | 1979-03-27 |
| DE2436472A1 (de) | 1975-02-27 |
| DE2436472C3 (de) | 1980-08-14 |
| JPS5039789A (de) | 1975-04-12 |
| CH593635A5 (de) | 1977-12-15 |
| JPS5230509B2 (de) | 1977-08-09 |
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