CA1054441A - Flavour modification - Google Patents
Flavour modificationInfo
- Publication number
- CA1054441A CA1054441A CA253,491A CA253491A CA1054441A CA 1054441 A CA1054441 A CA 1054441A CA 253491 A CA253491 A CA 253491A CA 1054441 A CA1054441 A CA 1054441A
- Authority
- CA
- Canada
- Prior art keywords
- flavour
- compound
- preparation
- alkyl
- ppm
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 80
- 235000019634 flavors Nutrition 0.000 title claims abstract description 76
- 238000012986 modification Methods 0.000 title description 3
- 230000004048 modification Effects 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 49
- 241000208125 Nicotiana Species 0.000 claims abstract description 19
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims abstract description 19
- -1 bicyclic compound Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 58
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 50
- 230000000694 effects Effects 0.000 claims description 37
- 238000001816 cooling Methods 0.000 claims description 30
- 239000003607 modifier Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000000051 modifying effect Effects 0.000 claims description 9
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 210000000653 nervous system Anatomy 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical class CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- YCTDZYMMFQCTEO-UHFFFAOYSA-N 3-octene Chemical class CCCCC=CCC YCTDZYMMFQCTEO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000004936 stimulating effect Effects 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002253 acid Substances 0.000 abstract description 7
- 150000001408 amides Chemical class 0.000 abstract description 7
- 150000002148 esters Chemical class 0.000 abstract description 6
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 23
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 18
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000002619 bicyclic group Chemical group 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 229940041616 menthol Drugs 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 235000019640 taste Nutrition 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 235000009508 confectionery Nutrition 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000005979 Citrus limon Nutrition 0.000 description 3
- 244000131522 Citrus pyriformis Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- 244000269722 Thea sinensis Species 0.000 description 3
- 244000299461 Theobroma cacao Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000003264 margarine Substances 0.000 description 3
- 235000013310 margarine Nutrition 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 230000008447 perception Effects 0.000 description 3
- 235000014347 soups Nutrition 0.000 description 3
- 235000013616 tea Nutrition 0.000 description 3
- DEOUZFWSQWEPGE-UHFFFAOYSA-N 2-methylheptanamide Chemical compound CCCCCC(C)C(N)=O DEOUZFWSQWEPGE-UHFFFAOYSA-N 0.000 description 2
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 2
- OUJMZCPIRVTFCV-UHFFFAOYSA-N 4-methylpent-2-enoyl chloride Chemical compound CC(C)C=CC(Cl)=O OUJMZCPIRVTFCV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000219104 Cucurbitaceae Species 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 206010013911 Dysgeusia Diseases 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000001890 Ribes hudsonianum Species 0.000 description 2
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 2
- 235000001466 Ribes nigrum Nutrition 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000015218 chewing gum Nutrition 0.000 description 2
- 229940112822 chewing gum Drugs 0.000 description 2
- 235000019219 chocolate Nutrition 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 108091005708 gustatory receptors Proteins 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 2
- 235000013923 monosodium glutamate Nutrition 0.000 description 2
- 239000004223 monosodium glutamate Substances 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- ZQMPWXFHAUDENN-UHFFFAOYSA-N n,n'-bis(2-methylphenyl)ethane-1,2-diamine Chemical compound CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 235000019600 saltiness Nutrition 0.000 description 2
- 235000019614 sour taste Nutrition 0.000 description 2
- 235000020354 squash Nutrition 0.000 description 2
- 230000009967 tasteless effect Effects 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 235000020097 white wine Nutrition 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
- WQFGPARDTSBVLU-UHFFFAOYSA-N (1R,2S,3S,4R)-p-Menthane-2,3-diol Chemical compound CC(C)C1CCC(C)C(O)C1O WQFGPARDTSBVLU-UHFFFAOYSA-N 0.000 description 1
- XXZAOMJCZBZKPV-WEDXCCLWSA-N (1r,3s,4r)-3-chloro-4,7,7-trimethylbicyclo[2.2.1]heptane Chemical compound C1C[C@@]2(C)[C@@H](Cl)C[C@@H]1C2(C)C XXZAOMJCZBZKPV-WEDXCCLWSA-N 0.000 description 1
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
- INANBEZVOZRFOA-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl)methanol Chemical compound CC(C)C1CCC(C)CC1CO.CC(C)C1CCC(C)CC1CO INANBEZVOZRFOA-UHFFFAOYSA-N 0.000 description 1
- HOMYCSGLOGENFE-UHFFFAOYSA-N 2,4,6-trimethylhept-2-en-4-ol Chemical compound CC(C)CC(C)(O)C=C(C)C HOMYCSGLOGENFE-UHFFFAOYSA-N 0.000 description 1
- QSVYJSJPLCSACO-UHFFFAOYSA-N 2,4,6-trimethylheptan-4-ol Chemical compound CC(C)CC(C)(O)CC(C)C QSVYJSJPLCSACO-UHFFFAOYSA-N 0.000 description 1
- OXXDGKNPRNPMLS-UHFFFAOYSA-N 2-Hydroxy-3-methyl-4H-pyran-4-one Natural products CC1=C(O)OC=CC1=O OXXDGKNPRNPMLS-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- GBSXCHLYXIBMCZ-UHFFFAOYSA-N 2-ethyl-n,n-dimethylbutanamide Chemical compound CCC(CC)C(=O)N(C)C GBSXCHLYXIBMCZ-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- QKDCLUARMDUUKN-XMMPIXPASA-N 6-ethyl-3-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]-5-[(3r)-1-prop-2-enoylpyrrolidin-3-yl]oxypyrazine-2-carboxamide Chemical compound N1=C(O[C@H]2CN(CC2)C(=O)C=C)C(CC)=NC(C(N)=O)=C1NC(C=C1)=CC=C1N(CC1)CCC1N1CCN(C)CC1 QKDCLUARMDUUKN-XMMPIXPASA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 235000016795 Cola Nutrition 0.000 description 1
- 235000011824 Cola pachycarpa Nutrition 0.000 description 1
- XXZAOMJCZBZKPV-UHFFFAOYSA-N DL-bornyl chloride Natural products C1CC2(C)C(Cl)CC1C2(C)C XXZAOMJCZBZKPV-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 241000048448 Rhoicissus tridentata Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- SLIUELDPAPMQIB-IDIVVRGQSA-N [Na].[Na].[C@@H]1([C@H](O)[C@H](O)[C@@H](COP(=O)(O)O)O1)N1C=NC=2C(O)=NC=NC12 Chemical compound [Na].[Na].[C@@H]1([C@H](O)[C@H](O)[C@@H](COP(=O)(O)O)O1)N1C=NC=2C(O)=NC=NC12 SLIUELDPAPMQIB-IDIVVRGQSA-N 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 235000020140 chocolate milk drink Nutrition 0.000 description 1
- 235000011967 chocolate pudding Nutrition 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 235000019506 cigar Nutrition 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000013409 condiments Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- PVBRXXAAPNGWGE-LGVAUZIVSA-L disodium 5'-guanylate Chemical compound [Na+].[Na+].C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O PVBRXXAAPNGWGE-LGVAUZIVSA-L 0.000 description 1
- 239000004193 disodium 5'-ribonucleotide Substances 0.000 description 1
- 235000013896 disodium guanylate Nutrition 0.000 description 1
- 235000013890 disodium inosinate Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000008369 fruit flavor Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- QAOXMQCWUWZZNC-UHFFFAOYSA-N gamma-Methyl-alpha-butylen-alpha-carbonsaeure Natural products CC(C)C=CC(O)=O QAOXMQCWUWZZNC-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 235000020278 hot chocolate Nutrition 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- KLVRKNJSKXACLQ-UHFFFAOYSA-N n,n,2-triethylbutanamide Chemical compound CCC(CC)C(=O)N(CC)CC KLVRKNJSKXACLQ-UHFFFAOYSA-N 0.000 description 1
- ZZUWAVJHDTWSFC-UHFFFAOYSA-N n,n-diethyl-2,2-dimethylpropanamide Chemical compound CCN(CC)C(=O)C(C)(C)C ZZUWAVJHDTWSFC-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 229930004008 p-menthane Natural products 0.000 description 1
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane group Chemical class C1(CCC(CC1)C(C)C)C CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000020095 red wine Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 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
- 239000000126 substance Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic 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
- A23L27/203—Alicyclic 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
- A23L27/204—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
- A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
-
- 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
- A24B15/345—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring containing condensed rings
-
- 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
- A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/13—Monohydroxylic alcohols containing saturated rings
- C07C31/137—Monohydroxylic alcohols containing saturated rings polycyclic with condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
- Manufacture Of Tobacco Products (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cigarettes, Filters, And Manufacturing Of Filters (AREA)
- General Preparation And Processing Of Foods (AREA)
- Non-Alcoholic Beverages (AREA)
- Medicinal Preparation (AREA)
- Confectionery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23947/75A GB1502680A (en) | 1975-06-03 | 1975-06-03 | Compositions for application to or consumption by the human body and containing compounds having a physiological cooling effect |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1054441A true CA1054441A (en) | 1979-05-15 |
Family
ID=10203902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA253,491A Expired CA1054441A (en) | 1975-06-03 | 1976-05-27 | Flavour modification |
Country Status (14)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7810966A (nl) | 1978-11-03 | 1980-05-07 | Naarden International Nv | Parfumcomposities en geparfumeerde produkten, die een bicyclisch monoterpeenzuur als parfumgrondstof bevat- ten. |
| NL8003068A (nl) * | 1980-05-28 | 1982-01-04 | Naarden & Shell Aroma Chem | Parfumcomposities en geparfumeerde materialen en voorwerpen die esters van bicyclische monoterpeenzuren als grondstof bevatten. |
| NL8601541A (nl) * | 1986-06-13 | 1988-01-04 | Naarden International Nv | Cyclohexaan-, cyclohexeen- en cyclohexadieen-, bicyclo-2.2.1 heptaan- en bicyclo2.2.1hepteencarbonzure alkylesters, alsmede parfumcomposities en geparfumeerde produkten die een of meer van deze verbindingen als parfumgrondstof bevatten. |
| HU200103B (en) * | 1987-04-01 | 1990-04-28 | Biogal Gyogyszergyar | Process for producing pharmaceutical compositions for treating lack of epithelium |
| RU2214721C2 (ru) | 1997-09-18 | 2003-10-27 | Вм. Ригли Дж. Компани | Способ производства жевательной резинки с физиологическими охлаждающими агентами (варианты), жевательная резинка по этому способу, композиция охлаждающего ароматизирующего вещества, жевательная резинка, включающая эту композицию, покрытая жевательная резинка (варианты), способ усиления вкусового воздействия покрытой жевательной резинки, способ покрытия жевательной резинки, композиция жевательной резинки |
| US6455080B1 (en) | 1997-12-29 | 2002-09-24 | Wm. Wrigley Jr., Company | Chewing gum containing controlled release acyclic carboxamide and method of making |
| US6627233B1 (en) | 1997-09-18 | 2003-09-30 | Wm. Wrigley Jr. Company | Chewing gum containing physiological cooling agents |
| DK1541044T3 (da) | 2002-09-19 | 2012-05-14 | Japan Tobacco Inc | Cigaretfilter |
| NZ545747A (en) * | 2003-08-06 | 2010-06-25 | Senomyx Inc | T1R hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds |
| US20060045953A1 (en) * | 2004-08-06 | 2006-03-02 | Catherine Tachdjian | Aromatic amides and ureas and their uses as sweet and/or umami flavor modifiers, tastants and taste enhancers |
| CA2597134C (en) | 2005-02-04 | 2015-05-26 | Senomyx, Inc. | Compounds comprising linked heteroaryl moieties and their use as novel umami flavor modifiers, tastants and taste enhancers for comestible compositions |
| AR055329A1 (es) | 2005-06-15 | 2007-08-15 | Senomyx Inc | Amidas bis-aromaticas y sus usos como modificadores de sabor dulce, saborizantes, y realzadores de sabor |
| WO2007022651A1 (en) * | 2005-08-22 | 2007-03-01 | Givaudan Sa | Substituted bicyclo [2.2.2] oct/5-ene compounds and their use as cooling agents |
| EP2559424A1 (en) | 2005-10-05 | 2013-02-20 | Kraft Foods Global Brands LLC | Cooling composition comprising trimethyl isopropyl butanamide |
| EP2478777B1 (en) | 2005-12-23 | 2014-07-09 | Intercontinental Great Brands LLC | Composition providing a cooling sensation substantially similar to that provided by menthol |
| ES2640453T3 (es) | 2006-04-21 | 2017-11-03 | Senomyx, Inc. | Procesos para preparar composiciones saborizantes sólidas |
| EP2167024B1 (en) * | 2007-06-13 | 2012-01-11 | Givaudan SA | Cooling compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250815A (en) * | 1962-02-05 | 1966-05-10 | Universal Oil Prod Co | Bicyclo (2.2.1) heptyl carbinols |
| FR1472947A (fr) * | 1964-06-22 | 1967-03-17 | Du Pont | Bicyclo [2, 2, 2]-octènes et leur préparation |
-
1975
- 1975-06-03 GB GB23947/75A patent/GB1502680A/en not_active Expired
-
1976
- 1976-05-26 ZA ZA763155A patent/ZA763155B/xx unknown
- 1976-05-26 ZA ZA763156A patent/ZA763156B/xx unknown
- 1976-05-27 CA CA253,491A patent/CA1054441A/en not_active Expired
- 1976-05-28 DE DE19762623868 patent/DE2623868A1/de active Pending
- 1976-05-31 AU AU14468/76A patent/AU1446876A/en not_active Expired
- 1976-05-31 IT IT23816/76A patent/IT1060882B/it active
- 1976-05-31 IT IT23815/76A patent/IT1060764B/it active
- 1976-05-31 AU AU14469/76A patent/AU503510B2/en not_active Expired
- 1976-06-01 NL NL7605914A patent/NL7605914A/xx not_active Application Discontinuation
- 1976-06-01 BR BR3484/76A patent/BR7603484A/pt unknown
- 1976-06-01 DE DE19762624504 patent/DE2624504A1/de not_active Withdrawn
- 1976-06-01 LU LU75062A patent/LU75062A1/xx unknown
- 1976-06-01 LU LU75061A patent/LU75061A1/xx unknown
- 1976-06-01 NL NL7605913A patent/NL7605913A/xx unknown
- 1976-06-01 JP JP51064033A patent/JPS51148040A/ja active Pending
- 1976-06-01 JP JP51064032A patent/JPS51148074A/ja active Pending
- 1976-06-02 DK DK242876A patent/DK242876A/da unknown
- 1976-06-02 FR FR7616608A patent/FR2312971A1/fr active Granted
- 1976-06-02 IE IE1182/76A patent/IE43232B1/en unknown
- 1976-06-02 FR FR7616607A patent/FR2391722A1/fr active Granted
- 1976-06-02 DK DK242776A patent/DK242776A/da unknown
- 1976-06-03 BE BE2055081A patent/BE842517A/xx not_active IP Right Cessation
- 1976-06-03 BE BE2055080A patent/BE842516A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU75061A1 (enrdf_load_stackoverflow) | 1977-01-21 |
| FR2312971A1 (fr) | 1976-12-31 |
| AU503510B2 (en) | 1979-09-06 |
| IE43232B1 (en) | 1981-01-14 |
| FR2391722B1 (enrdf_load_stackoverflow) | 1979-08-17 |
| LU75062A1 (enrdf_load_stackoverflow) | 1977-01-21 |
| JPS51148074A (en) | 1976-12-18 |
| NL7605913A (nl) | 1976-12-07 |
| AU1446876A (en) | 1977-12-08 |
| BE842516A (fr) | 1976-12-03 |
| FR2391722A1 (fr) | 1978-12-22 |
| IT1060882B (it) | 1982-09-30 |
| BR7603484A (pt) | 1977-01-04 |
| GB1502680A (en) | 1978-03-01 |
| IT1060764B (it) | 1982-09-30 |
| AU1446976A (en) | 1977-12-08 |
| NL7605914A (nl) | 1976-12-07 |
| ZA763156B (en) | 1977-04-27 |
| BE842517A (fr) | 1976-12-03 |
| DE2623868A1 (de) | 1976-12-16 |
| JPS51148040A (en) | 1976-12-18 |
| ZA763155B (en) | 1977-04-27 |
| FR2312971B3 (enrdf_load_stackoverflow) | 1979-02-23 |
| DK242776A (da) | 1976-12-04 |
| DK242876A (da) | 1976-12-04 |
| IE43232L (en) | 1976-12-03 |
| DE2624504A1 (de) | 1976-12-23 |
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