US20080108544A1 - Substituted hydrogenated naphthalene derivatives and their use in fragrance formulations - Google Patents
Substituted hydrogenated naphthalene derivatives and their use in fragrance formulations Download PDFInfo
- Publication number
- US20080108544A1 US20080108544A1 US11/556,801 US55680106A US2008108544A1 US 20080108544 A1 US20080108544 A1 US 20080108544A1 US 55680106 A US55680106 A US 55680106A US 2008108544 A1 US2008108544 A1 US 2008108544A1
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- United States
- Prior art keywords
- compound
- hydrogen
- group
- fragrance
- ppm
- Prior art date
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- Granted
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- 239000003205 fragrance Substances 0.000 title claims description 39
- 239000000203 mixture Substances 0.000 title claims description 22
- 238000009472 formulation Methods 0.000 title claims description 5
- 150000002790 naphthalenes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000001033 ether group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 239000002304 perfume Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 3
- 239000003643 water by type Substances 0.000 claims description 3
- 239000002386 air freshener Substances 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 238000004851 dishwashing Methods 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 238000005201 scrubbing Methods 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims 2
- 239000004744 fabric Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 10
- MFGWMAAZYZSWMY-UHFFFAOYSA-N (2-naphthyl)methanol Chemical compound C1=CC=CC2=CC(CO)=CC=C21 MFGWMAAZYZSWMY-UHFFFAOYSA-N 0.000 description 23
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 0 [1*]C(C)(C)C1([2*])CC2=c(cCCC2(C)C)cC1C.[1*]C(C)(C)C1([2*])CC2C(CCCC2(C)C)CC1C Chemical compound [1*]C(C)(C)C1([2*])CC2=c(cCCC2(C)C)cC1C.[1*]C(C)(C)C1([2*])CC2C(CCCC2(C)C)CC1C 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- -1 2-ethyl-propyl Chemical group 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 150000005829 chemical entities Chemical class 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229930002839 ionone Natural products 0.000 description 2
- 150000002499 ionone derivatives Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000002470 solid-phase micro-extraction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YBUIAJZFOGJGLJ-SWRJLBSHSA-N 1-cedr-8-en-9-ylethanone Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=C(C(C)=O)C2 YBUIAJZFOGJGLJ-SWRJLBSHSA-N 0.000 description 1
- FEWIGMWODIRUJM-UHFFFAOYSA-N 4-hexen-3-one Chemical compound CCC(=O)C=CC FEWIGMWODIRUJM-UHFFFAOYSA-N 0.000 description 1
- 235000011468 Albizia julibrissin Nutrition 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 241000205585 Aquilegia canadensis Species 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- QKKSNZVRCDPKTC-UHFFFAOYSA-N CC(CC(CCC=C(C)C)=CC1)C1(C)C(C)=O Chemical compound CC(CC(CCC=C(C)C)=CC1)C1(C)C(C)=O QKKSNZVRCDPKTC-UHFFFAOYSA-N 0.000 description 1
- FVUGZKDGWGKCFE-UHFFFAOYSA-N CC(CC1=C(C2)C(C)(C)CCC1)C2(C)C(C)=O Chemical compound CC(CC1=C(C2)C(C)(C)CCC1)C2(C)C(C)=O FVUGZKDGWGKCFE-UHFFFAOYSA-N 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 235000009917 Crataegus X brevipes Nutrition 0.000 description 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 description 1
- 235000009685 Crataegus X maligna Nutrition 0.000 description 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 description 1
- 235000009486 Crataegus bullatus Nutrition 0.000 description 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 description 1
- 235000009682 Crataegus limnophila Nutrition 0.000 description 1
- 240000000171 Crataegus monogyna Species 0.000 description 1
- 235000004423 Crataegus monogyna Nutrition 0.000 description 1
- 235000002313 Crataegus paludosa Nutrition 0.000 description 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 description 1
- 241000612152 Cyclamen hederifolium Species 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000919496 Erysimum Species 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 240000001972 Gardenia jasminoides Species 0.000 description 1
- 244000215562 Heliotropium arborescens Species 0.000 description 1
- 241001632576 Hyacinthus Species 0.000 description 1
- PMGCQNGBLMMXEW-UHFFFAOYSA-N Isoamyl salicylate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1O PMGCQNGBLMMXEW-UHFFFAOYSA-N 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 240000006568 Lathyrus odoratus Species 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- 241000218378 Magnolia Species 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 235000014749 Mentha crispa Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 244000078639 Mentha spicata Species 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 240000005852 Mimosa quadrivalvis Species 0.000 description 1
- 241000234479 Narcissus Species 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 240000002505 Pogostemon cablin Species 0.000 description 1
- 235000011751 Pogostemon cablin Nutrition 0.000 description 1
- 244000014047 Polianthes tuberosa Species 0.000 description 1
- 235000016067 Polianthes tuberosa Nutrition 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 241001128140 Reseda Species 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 244000297179 Syringa vulgaris Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 244000263375 Vanilla tahitensis Species 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229930186364 cyclamen Natural products 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- USKZHEQYENVSMH-UHFFFAOYSA-N hepta-1,3,5-triene Chemical compound CC=CC=CC=C USKZHEQYENVSMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/05—Alcohols containing rings other than six-membered aromatic rings
- C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/162—Unsaturated ethers containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- 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
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
- C11B9/0053—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms both rings being six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
Definitions
- the present invention relates to new chemical entities and the incorporation and use of the new chemical entities as fragrance materials.
- the present invention provides novel chemicals, and the use of the chemicals to enhance the fragrance of perfumes, toilet waters, colognes, personal products and the like.
- the present invention is directed to the use of the novel chemicals to enhance fragrance in perfumes, toilet waters, colognes, personal products and the like.
- R is hydrogen
- Another embodiment of the invention is a method for enhancing a perfume composition by incorporating an olfactory acceptable amount of the compound provided above.
- R is selected from the group consisting of hydrogen, a straight, branched or cyclic alkyl that may or may not be unsaturated, alkenyl groups, an acetyl group, a substituted acetyl groups, an alkoxy ether group or alkyl substituted alkoxy ether moieties with each R, other than hydrogen comprising from 1 to 10 carbon atoms and more preferably 1 to 4 carbon atoms, alkoxy ether groups and alkyl substituted alkoxy ether moieties such as, but not limited to, CH 2 —O—CH 2 —R 5 wherein R 3 is a C1-C4 alkyl group as well as double bond containing alkyl groups;
- Suitable straight hydrocarbon moieties include alkanes such as but not limited to methyl, ethyl, propyl, butyl, pentyl, hexyl, and the like.
- Suitable branched hydrocarbon moieties include alkanes such as but not limited to isopropyl, sec-butyl, tert-butyl, diethyl, 2-ethyl-propyl, and the like.
- Suitable cyclic hydrocarbon moieties include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, and the like.
- Suitable alkenes containing double bonds include ethene, propene, 1-butene, 2-butene, penta-1-3-deine, hepta-1,3,5-triene and the like.
- novel compounds of the present invention are represented by the following structures:
- Structure I is 2-Naphthalenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,2,3,8,8-pentamethyl-,acetate.
- Structure II is 2-Naphthalenemethanol,1,2,3,4,5,6,7,8,-octahydro-alpha,2,3,8,8-pentamethyl.
- Structure III is Naphthalenemethanol, 1,2,3,4,5,6,7,8-octahydro-7-(1-methoxyethyl)-1,1,6,7-tetramethyl.
- Structure IV is 2-Naphthalenemethanol,1,2,3,4,5,6,7,8-octahydro-alpha, alpha,2,3,8,8-hexamethyl.
- Structure V is Naphthalene,7-[1-(ethoxymethoxy)ethyl]-1,2,3,4,5,6,7, 8-octahydro-1,1,6-trimethyl.
- Structure VI is Napthalene,1,2,3,4,5,6,7,8-octahydro-7-[1-(methoxymethoxy)ethyl]-1,1,6,7-tertramethyl-.
- the compounds of the present invention may be prepared from the corresponding myrcene and methyl pentenone via a Diels-Alder reaction followed by cyclization with an acid as delineated in the following sequence.
- Iso E super is a registered fragrance ingredient from International Flavors & Fragrances Inc.
- the starting materials for the above reactions are available from the International Flavors & Fragrances Inc.
- fragrance compounds of Structure I -VII impart naturalness to the fragrance formulations and are well suited for use as fragrance ingredients.
- the use of the compounds of the present invention is widely applicable in current perfumery products, including the preparation of perfumes and colognes, the perfuming of personal care products such as soaps, shower gels, and hair care products as well as air fresheners and cosmetic preparations.
- the present invention can also be used to perfume cleaning agents, such as, but not limited to detergents, dishwashing materials, scrubbing compositions, window cleaners and the like.
- the compounds of the present invention can be used alone or in combination with other perfuming compositions, solvents, adjuvants and the like.
- the nature and variety of the other ingredients that can also be employed are known to those with skill in the art.
- fragrances can be employed in the present invention, the only limitation being the compatibility with the other components being employed.
- Suitable fragrances include but are not limited to fruits such as almond, apple, cherry, grape, pear, pineapple, orange, strawberry, raspberry; musk, flower scents such as lavender-like, rose-like, iris-like, carnation-like.
- Other pleasant scents include herbal and woodland scents derived from pine, spruce and other forest smells.
- Fragrances may also be derived from various oils, such as essential oils, or from plant materials such as peppermint, spearmint and the like.
- fragrances provided in this treatise are acacia, cassie, chypre, cyclamen, fern, gardenia, hawthorn, heliotrope, honeysuckle, hyacinth, jasmine, lilac, lily, magnolia, mimosa, narcissus, freshly-cut hay, orange blossom, orchid, reseda, sweet pea, trefle, tuberose, vanilla, violet, wallflower, and the like.
- Olfactory effective amount is understood to mean the amount of compound in perfume compositions the individual component will contribute to its particular olfactory characteristics, but the olfactory effect of the perfume composition will be the sum of the effects of each of the perfumes or fragrance ingredients.
- the compounds of the invention can be used to alter the aroma characteristics of the perfume composition, or by modifying the olfactory reaction contributed by another ingredient in the composition. The amount will vary depending on many factors including other ingredients, their relative amounts and the effect that is desired.
- the level of compound of the invention employed in the perfumed article varies from about 0.005 to about 10 weight percent, preferably from about 0.5 to about 8 and most preferably from about 1 to about 7 weight percent.
- other agents can be used in conjunction with the fragrance.
- Well known materials such as surfactants, emulsifiers, polymers to encapsulate the fragrance can also be employed without departing from the scope of the present invention.
- the compounds of the invention can range widely from 0.005 to about 70 weight percent of the perfumed composition, preferably from about 0. 1 to about 50 and most preferably from about 0.2 to about 25 weight percent. Those with skill in the art will be able to employ the desired level of the compounds of the invention to provide the desired fragrance and intensity.
- the product had woody, sweet, buttery and ionone fragrance notes.
- the NMR spectrum of the 2-Naphthalenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,2,3,8,8-pentamethyl,acetate is as follows: 0.7 ppm-1.0 ppm (m, 15H); 1.1 ppm-1.2 ppm (m, 5H); 1.3 ppm (m, 1H); 1.4 ppm (d, 3H); 1.5 ppm -2.0 ppm(m, 6H); 2.1 ppm (s, 3H); 4.9 ppm(m,1H).
- the product had fatty, woody and ambery fragrance notes.
- the product has a very nice ambery character, woody, vertofix, IsoE, musky and patchouli fragrance notes.
- the NMR spectrum of the 2-Naphthalenemethanol,1,2,3,4,5,6,7,8-octahydro-alpha, alpha,2,3,8,8-hexamethyl is as follows: 0.8 ppm (s, 3H); 0.9 ppm (s, 9H); 1.1 ppm (s, 3H); 1.2 ppm (s, 3H); 1.5-2.1 ppm (m, 10H); 4.8-5.25 ppm (m, 1H).
- the product has fatty and woody fragrance notes.
- the NMR spectrum of the 2-Naphthalenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,2,3,8,8-pentamethyl is as follows: 0.65-0.9 ppm (ms, 12H); 1.1 ppm (d, 3H); 1.4-2.1 ppm (m, 7H); 3.75 ppm (m, 1H); 5.1-5.2 ppm (m, 1H).
- the product had woody, ionone, less ambery fragrance notes.
- the NMR spectrum of the Naphthalene,7-[1-(ethoxymethoxy)ethyl]-1,2,3,4,5,6,7,8-octahydro-1,1,6-trimethyl is as follows: 0.6 ppm to 0.6 ppm (ms, 10H); 0.9 ppm (m, 4H); 1.0 ppm (s, 2H); 1.1 ppm-1.2 ppm (m, 6H); 1.3-1.5 ppm (m, 4H); 1.6 ppm (s, H); 1.7-1.9(m,3H); 2.1 ppm (s, H); 3.5 ppm-3.7 ppm (bs, 3H); 4.6 ppm (d, H); 4.8 ppm (d, H).
- the product had sweet, woody, buttery and grisalva fragrance notes.
- the NMR spectrum of the Naphthalene,7-[1-(ethoxymethoxy)ethyl]-1,2,3,4,5,6,7,8-octahydro-1,1,6-trimethyl is as follows: 0.7 ppm -0.9 ppm (ms, 10H); 1.0 ppm (m, 4H); 1.1 ppm -1.2 ppm (m, 5H); 1.3 ppm -1.4 ppm (m, 4H); 1.5-1.7 ppm (m, 6H); 1.8 ppm -1.9 ppm (m,3H); 2.1 ppm (s, H); 3.4 ppm (s, 3H); 3.6 ppm (s, H); 4.6 ppm (d, H); 4.8 ppm (d, H).
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Abstract
Description
- The present invention relates to new chemical entities and the incorporation and use of the new chemical entities as fragrance materials.
- There is an ongoing need in the fragrance industry to provide new chemicals to give perfumers and other persons ability to create new fragrances for perfumes, colognes and personal care products. Those with skill in the art appreciate how differences in the chemical structure of the molecule can result in significant differences in the odor, notes and characteristics of a molecule. These variations and the ongoing need to discover and use the new chemicals in the development of new fragrances allows perfumers to apply the new compounds in creating new fragrances.
- The present invention provides novel chemicals, and the use of the chemicals to enhance the fragrance of perfumes, toilet waters, colognes, personal products and the like. In addition, the present invention is directed to the use of the novel chemicals to enhance fragrance in perfumes, toilet waters, colognes, personal products and the like.
- More specifically, the present invention is directed to the novel compounds, represented by Formula I and II set forth below:
- wherein R is hydrogen,
- a straight, branched or cyclic hydrocarbon moiety consisting of less than 10, most preferably less than 4 carbon atoms and containing single and/or double bonds,
- an acetyl group and substituted acetyl groups including cyclic groups, such as cyclopropyl acyl group,
- alkoxy ether groups and alkyl substituted alkoxy ether moieties such as, but not limited to, CH2—O—CH2—R5 wherein R3 is a C1-C4 alkyl group as well as double bond containing alkyl groups;
- R1, R2 and R3 may be independently selected from hydrogen, a C1-C4 alkyl group such as methyl and ethyl;
- and when one of the dashed lines is a double bond and the other dashed line is a single bond.
- Another embodiment of the invention is a method for enhancing a perfume composition by incorporating an olfactory acceptable amount of the compound provided above.
- These and other embodiments of the present invention will be apparent by reading the following specification.
- R is selected from the group consisting of hydrogen, a straight, branched or cyclic alkyl that may or may not be unsaturated, alkenyl groups, an acetyl group, a substituted acetyl groups, an alkoxy ether group or alkyl substituted alkoxy ether moieties with each R, other than hydrogen comprising from 1 to 10 carbon atoms and more preferably 1 to 4 carbon atoms, alkoxy ether groups and alkyl substituted alkoxy ether moieties such as, but not limited to, CH2—O—CH2—R5 wherein R3 is a C1-C4 alkyl group as well as double bond containing alkyl groups;
- R1, R2 and R3 may be independently selected from hydrogen, a C1-C4 alkyl group such as methyl and ethyl; and
- in which one of the dashed lines is a double bond and the other dashed line is a single bond.
- Suitable straight hydrocarbon moieties include alkanes such as but not limited to methyl, ethyl, propyl, butyl, pentyl, hexyl, and the like. Suitable branched hydrocarbon moieties include alkanes such as but not limited to isopropyl, sec-butyl, tert-butyl, diethyl, 2-ethyl-propyl, and the like. Suitable cyclic hydrocarbon moieties include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, and the like. Suitable alkenes containing double bonds include ethene, propene, 1-butene, 2-butene, penta-1-3-deine, hepta-1,3,5-triene and the like.
- In a preferred embodiment of the invention, the novel compounds of the present invention are represented by the following structures:
- Those with the skill in the art will appreciate that the following compounds:
- Structure I is 2-Naphthalenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,2,3,8,8-pentamethyl-,acetate.
- Structure II is 2-Naphthalenemethanol,1,2,3,4,5,6,7,8,-octahydro-alpha,2,3,8,8-pentamethyl.
- Structure III is Naphthalenemethanol, 1,2,3,4,5,6,7,8-octahydro-7-(1-methoxyethyl)-1,1,6,7-tetramethyl.
- Structure IV is 2-Naphthalenemethanol,1,2,3,4,5,6,7,8-octahydro-alpha, alpha,2,3,8,8-hexamethyl.
- Structure V is Naphthalene,7-[1-(ethoxymethoxy)ethyl]-1,2,3,4,5,6,7, 8-octahydro-1,1,6-trimethyl.
- Structure VI is Napthalene,1,2,3,4,5,6,7,8-octahydro-7-[1-(methoxymethoxy)ethyl]-1,1,6,7-tertramethyl-.
- Structure VII 2-Naphthalenemethanol, 1,23,4,5,6,7,8,9,10-decahydro-alpha,2,3,8,8-pentamethyl.
- Structure VIII 2-Naphthalenemethanol, 1,2,3,4,5,6,7,8,9,10-decahydro-alpha,alpha,2,3,8,8-hexamethyl.
- The compounds of the present invention may be prepared from the corresponding myrcene and methyl pentenone via a Diels-Alder reaction followed by cyclization with an acid as delineated in the following sequence. Iso E super is a registered fragrance ingredient from International Flavors & Fragrances Inc.
- The starting materials for the above reactions are available from the International Flavors & Fragrances Inc.
- Those with skill in the art will recognize that some of the compounds of the present invention have a number of chiral centers, thereby providing numerous isomers of the claimed compounds. It is intended herein that the compounds described herein include isomeric mixtures of such compounds, as well as those isomers that may be separated using techniques known to those having skill in the art. Suitable techniques include chromatography such as HPLC, and particularly gel chromatography and solid phase microextraction (“SPME”).
- We have discovered that the fragrance compounds of Structure I -VII impart naturalness to the fragrance formulations and are well suited for use as fragrance ingredients.
- The use of the compounds of the present invention is widely applicable in current perfumery products, including the preparation of perfumes and colognes, the perfuming of personal care products such as soaps, shower gels, and hair care products as well as air fresheners and cosmetic preparations. The present invention can also be used to perfume cleaning agents, such as, but not limited to detergents, dishwashing materials, scrubbing compositions, window cleaners and the like.
- In these preparations, the compounds of the present invention can be used alone or in combination with other perfuming compositions, solvents, adjuvants and the like. The nature and variety of the other ingredients that can also be employed are known to those with skill in the art.
- Many types of fragrances can be employed in the present invention, the only limitation being the compatibility with the other components being employed. Suitable fragrances include but are not limited to fruits such as almond, apple, cherry, grape, pear, pineapple, orange, strawberry, raspberry; musk, flower scents such as lavender-like, rose-like, iris-like, carnation-like. Other pleasant scents include herbal and woodland scents derived from pine, spruce and other forest smells. Fragrances may also be derived from various oils, such as essential oils, or from plant materials such as peppermint, spearmint and the like.
- A list of suitable fragrances is provided in U.S. Pat. No. 4,534,891, the contents of which are incorporated by reference as if set forth in its entirety. Another source of suitable fragrances is found in Perfumes Cosmetics and Soaps, Second Edition, edited by W. A. Poucher, 1959. Among the fragrances provided in this treatise are acacia, cassie, chypre, cyclamen, fern, gardenia, hawthorn, heliotrope, honeysuckle, hyacinth, jasmine, lilac, lily, magnolia, mimosa, narcissus, freshly-cut hay, orange blossom, orchid, reseda, sweet pea, trefle, tuberose, vanilla, violet, wallflower, and the like.
- Olfactory effective amount is understood to mean the amount of compound in perfume compositions the individual component will contribute to its particular olfactory characteristics, but the olfactory effect of the perfume composition will be the sum of the effects of each of the perfumes or fragrance ingredients. Thus the compounds of the invention can be used to alter the aroma characteristics of the perfume composition, or by modifying the olfactory reaction contributed by another ingredient in the composition. The amount will vary depending on many factors including other ingredients, their relative amounts and the effect that is desired.
- The level of compound of the invention employed in the perfumed article varies from about 0.005 to about 10 weight percent, preferably from about 0.5 to about 8 and most preferably from about 1 to about 7 weight percent. In addition to the compounds other agents can be used in conjunction with the fragrance. Well known materials such as surfactants, emulsifiers, polymers to encapsulate the fragrance can also be employed without departing from the scope of the present invention.
- Another method of reporting the level of the compounds of the invention in the perfumed composition, i.e., the compounds as a weight percentage of the materials added to impart the desired fragrance. The compounds of the invention can range widely from 0.005 to about 70 weight percent of the perfumed composition, preferably from about 0. 1 to about 50 and most preferably from about 0.2 to about 25 weight percent. Those with skill in the art will be able to employ the desired level of the compounds of the invention to provide the desired fragrance and intensity.
- The following examples are provided as specific embodiments of the present invention. Other modifications of this invention will be readily apparent to those skilled in the art. Such modifications are understood to be within the scope of this invention. As used herein all percentages are weight percent unless otherwise noted, ppm is understood to stand for parts per million and g is understood to be grams. IFF as used in the examples is understood to mean International Flavors & Fragrances Inc., New York, N.Y., USA.
- To a dry 2 L multi-neck round bottom flask fitted with an air stirrer, nitrogen inlet condenser and an addition funnel 452 g of Iso E Alcohol, 1000 ml of toluene and 15 g of pyridine were added and stirred. Then 400 g of acetic anhydride was added dropwise at a rate of 2 moles an hour. The mixture was aged for 2 hours and then quenched with 100 ml of cold water followed by 1 liter of 10% Na2CO3.
- The product had woody, sweet, buttery and ionone fragrance notes.
- The NMR spectrum of the 2-Naphthalenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,2,3,8,8-pentamethyl,acetate is as follows: 0.7 ppm-1.0 ppm (m, 15H); 1.1 ppm-1.2 ppm (m, 5H); 1.3 ppm (m, 1H); 1.4 ppm (d, 3H); 1.5 ppm -2.0 ppm(m, 6H); 2.1 ppm (s, 3H); 4.9 ppm(m,1H).
- To a dry 2 L multi-neck round bottom flask fitted with an air stirrer, nitrogen inlet condenser and an addition funnel 22 g of NaH and 650 ml of THF (tetrahydrofuran) and heat to 60° C. Then add the 50 ml of THF with 120 g of Iso E Alcohol to the addition funnel dropwise. Then 78 g of CH3I was added dropwise and then cooled. The mixture was aged for 2 hours and then quenched with 100 ml of cold water followed by 1 liter of 10% Na2CO3.
- The product had fatty, woody and ambery fragrance notes.
- The NMR spectrum of the Naphthalene, 1,2,3,4,5,6,7,8-octahydro-7-(1-methoxyethyl)-1,1,6,7-tetramethyl: 0.6 ppm (d, 2H); 0.7 ppm (s, H); 0.8 ppm (s, 3H); 0.9 ppm (s, 3H); 1.0 ppm (m, 1.1 ppm (m, 4H); 1.2 ppm (s, H); 1.5 ppm (m, 4H); 1.6 ppm (s, 3H); 2.1 ppm (s, H); 3.3 ppm (m, 3H).
- To a dry 2 L multi-neck, 3 necked reaction flask equipped with a mechanical stirrer, nitrogen inlet addition funnel and a cooling bath, was charged methyl lithium (800 ml, 1.6 in ether) and cooled it to 0° C., Iso E Super (374 g) was added at 0° C. in 1 hour and aged the reaction for 1 hour. The reaction mixture was quenched with 10% acetic acid solution. Transferred the contents to a separating funnel, separated the aqueous layer and washed the organic layer with saturated sodium bicarbohydrate solution (1200ml), concentrated the organic layer and washed it over to give 194 g of the product.
- The product has a very nice ambery character, woody, vertofix, IsoE, musky and patchouli fragrance notes.
- The NMR spectrum of the 2-Naphthalenemethanol,1,2,3,4,5,6,7,8-octahydro-alpha, alpha,2,3,8,8-hexamethyl is as follows: 0.8 ppm (s, 3H); 0.9 ppm (s, 9H); 1.1 ppm (s, 3H); 1.2 ppm (s, 3H); 1.5-2.1 ppm (m, 10H); 4.8-5.25 ppm (m, 1H).
- To a dry 2 L multi-neck, 3 necked reaction flask equipped with a mechanical stirrer, nitrogen inlet addition funnel and a cooling bath, was charged with NaBH4 and solvent at 30 C and then Iso E Super was added and the temperature was increased to 45 C then cooled over the duration of the feed. The mixture was aged for 1 hour and then heated to reflux at 78 C and aged for 9 hours. Then 200 ml of IPA/H2O and heated to reflux at 85 C and aged for 15 hours and allow the mixtures to settle over two days. The layers were separated and washed with organic with brine (200 ml) settle and separate to give a 99% yield.
- The product has fatty and woody fragrance notes.
- The NMR spectrum of the 2-Naphthalenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,2,3,8,8-pentamethyl is as follows: 0.65-0.9 ppm (ms, 12H); 1.1 ppm (d, 3H); 1.4-2.1 ppm (m, 7H); 3.75 ppm (m, 1H); 5.1-5.2 ppm (m, 1H).
- To a dry 2 L multi-neck, 3 necked reaction flask equipped with a mechanical stirrer, nitrogen inlet addition funnel and a cooling bath, was charged with alcohol, (ETO)2CH2, BF3OEt2 and CH3ONa and then heated to 80 C. The mixture was then distilled and then cooled and quenched with CH3ONa and washed base out with 100 ml water.
- The product had woody, ionone, less ambery fragrance notes.
- The NMR spectrum of the Naphthalene,7-[1-(ethoxymethoxy)ethyl]-1,2,3,4,5,6,7,8-octahydro-1,1,6-trimethyl is as follows: 0.6 ppm to 0.6 ppm (ms, 10H); 0.9 ppm (m, 4H); 1.0 ppm (s, 2H); 1.1 ppm-1.2 ppm (m, 6H); 1.3-1.5 ppm (m, 4H); 1.6 ppm (s, H); 1.7-1.9(m,3H); 2.1 ppm (s, H); 3.5 ppm-3.7 ppm (bs, 3H); 4.6 ppm (d, H); 4.8 ppm (d, H).
- To a dry 2 L multi-neck, 3 necked reaction flask equipped with a mechanical stirrer, nitrogen inlet addition funnel and a cooling bath, was charged with 236 g of Iso E Alcohol, 456 g of dimethoxy methane and 7.1 g of BF3OEt2. The mixture was then distilled and then cooled and quenched with CH3ONa and washed base out with 100 ml water.
- The product had sweet, woody, buttery and grisalva fragrance notes.
- The NMR spectrum of the Naphthalene,7-[1-(ethoxymethoxy)ethyl]-1,2,3,4,5,6,7,8-octahydro-1,1,6-trimethyl is as follows: 0.7 ppm -0.9 ppm (ms, 10H); 1.0 ppm (m, 4H); 1.1 ppm -1.2 ppm (m, 5H); 1.3 ppm -1.4 ppm (m, 4H); 1.5-1.7 ppm (m, 6H); 1.8 ppm -1.9 ppm (m,3H); 2.1 ppm (s, H); 3.4 ppm (s, 3H); 3.6 ppm (s, H); 4.6 ppm (d, H); 4.8 ppm (d, H).
Claims (15)
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US11/556,801 US7375062B1 (en) | 2006-11-06 | 2006-11-06 | Substituted hydrogenated naphthalene derivatives and their use in fragrance formulations |
EP07254376.2A EP1925607B1 (en) | 2006-11-06 | 2007-11-06 | Substituted hydrogenated naphthalene derivatives and their use in fragrance formulations |
CN2007101667703A CN101234967B (en) | 2006-11-06 | 2007-11-06 | Substituted hydrogenated naphthalene derivatives and use thereof in fragrance formulations |
ES07254376.2T ES2496969T3 (en) | 2006-11-06 | 2007-11-06 | Substituted hydrogenated naphthalene derivatives and their use in fragrance formulations |
US12/101,374 US7678756B2 (en) | 2006-11-06 | 2008-04-11 | Substituted hydrogenated naphthalene derivatives and their use in fragrance formulations |
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WO2013024363A1 (en) | 2011-08-17 | 2013-02-21 | Dow Global Technologies Llc | Biorenewable biodegradable surfactants |
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Citations (2)
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US5084440A (en) * | 1989-01-27 | 1992-01-28 | Givaudan Corporation | Acetals and ketals of oxo-tetralins and oxo-indanes |
US5332725A (en) * | 1992-10-26 | 1994-07-26 | Givaudan-Roure Corporation | Odorants |
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US3076022A (en) * | 1959-04-15 | 1963-01-29 | Givaudan Corp | Myrcene-methyl isopropenyl ketone adducts, derivatives thereof |
US3911018A (en) * | 1973-02-27 | 1975-10-07 | Int Flavors & Fragrances Inc | Novel process and products produced by said process |
US4534891A (en) | 1982-11-12 | 1985-08-13 | International Flavors & Fragrances Inc. | Branched C13 -alk-1-en-5-ones and use thereof in perfumery |
EP0595197B1 (en) * | 1992-10-26 | 1997-04-02 | Givaudan-Roure (International) S.A. | Enol ethers and odorant compositions containing them |
US20040131648A1 (en) * | 2002-10-24 | 2004-07-08 | The Procter & Gamble Company | Nuclear hormone receptor compounds, products and methods employing same |
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2006
- 2006-11-06 US US11/556,801 patent/US7375062B1/en not_active Expired - Fee Related
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2007
- 2007-11-06 EP EP07254376.2A patent/EP1925607B1/en not_active Not-in-force
- 2007-11-06 ES ES07254376.2T patent/ES2496969T3/en active Active
- 2007-11-06 CN CN2007101667703A patent/CN101234967B/en not_active Expired - Fee Related
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US5084440A (en) * | 1989-01-27 | 1992-01-28 | Givaudan Corporation | Acetals and ketals of oxo-tetralins and oxo-indanes |
US5332725A (en) * | 1992-10-26 | 1994-07-26 | Givaudan-Roure Corporation | Odorants |
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US20090227685A1 (en) | 2009-09-10 |
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ES2496969T3 (en) | 2014-09-22 |
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US7678756B2 (en) | 2010-03-16 |
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