CA1190564A - Aromatic musks - Google Patents

Aromatic musks

Info

Publication number: CA1190564A
Authority: CA; Canada
Prior art keywords: compound; compounds; methyl; ethyl; hydrogen
Prior art date: 1982-07-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000431610A

Other languages

English (en)

French (fr)

Inventor

Teodosij J. Zazula

Brian J. Willis

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

Fritzsche Dodge and Olcott Inc

Original Assignee

Fritzsche Dodge and Olcott Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-07-02

Filing date

1983-06-30

Publication date

1985-07-16

1983-06-30 Application filed by Fritzsche Dodge and Olcott Inc filed Critical Fritzsche Dodge and Olcott Inc

1985-07-16 Application granted granted Critical

1985-07-16 Publication of CA1190564A publication Critical patent/CA1190564A/en

Status Expired legal-status Critical Current

Links

241000402754 Erythranthe moschata Species 0.000 title abstract description 28
125000003118 aryl group Chemical group 0.000 title description 2
239000000203 mixture Substances 0.000 claims abstract description 93
150000001875 compounds Chemical class 0.000 claims abstract description 64
238000000034 method Methods 0.000 claims abstract description 31
239000003205 fragrance Substances 0.000 claims abstract description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
230000008569 process Effects 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
239000002304 perfume Substances 0.000 claims abstract description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
230000002708 enhancing effect Effects 0.000 claims description 2
230000001035 methylating effect Effects 0.000 claims 2
239000000463 material Substances 0.000 abstract description 10
239000000543 intermediate Substances 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000003921 oil Substances 0.000 description 19
235000019198 oils Nutrition 0.000 description 19
239000000243 solution Substances 0.000 description 18
239000002904 solvent Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 15
238000005160 1H NMR spectroscopy Methods 0.000 description 14
101150041968 CDC13 gene Proteins 0.000 description 14
238000004821 distillation Methods 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000012267 brine Substances 0.000 description 12
238000006170 formylation reaction Methods 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 11
230000022244 formylation Effects 0.000 description 11
239000004615 ingredient Substances 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 10
238000007069 methylation reaction Methods 0.000 description 10
230000009965 odorless effect Effects 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
235000009508 confectionery Nutrition 0.000 description 9
230000011987 methylation Effects 0.000 description 9
238000001228 spectrum Methods 0.000 description 8
239000000126 substance Substances 0.000 description 8
WPUPOYSDTDHCGJ-UHFFFAOYSA-N 1-methoxy-3,5,5,8,8-pentamethyl-6,7-dihydronaphthalene-2-carbaldehyde Chemical compound CC1(C)CCC(C)(C)C2=C1C(OC)=C(C=O)C(C)=C2 WPUPOYSDTDHCGJ-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
239000000344 soap Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000047 product Substances 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
239000003599 detergent Substances 0.000 description 5
230000001747 exhibiting effect Effects 0.000 description 5
239000004312 hexamethylene tetramine Substances 0.000 description 5
235000010299 hexamethylene tetramine Nutrition 0.000 description 5
238000002329 infrared spectrum Methods 0.000 description 5
229960004011 methenamine Drugs 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
230000003595 spectral effect Effects 0.000 description 5
UBVLFUVQJXMTAE-UHFFFAOYSA-N 1-methoxy-3,4,5,5,8,8-hexamethyl-6,7-dihydronaphthalene-2-carbaldehyde Chemical compound CC1(C)CCC(C)(C)C2=C1C(OC)=C(C=O)C(C)=C2C UBVLFUVQJXMTAE-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
SUAUILGSCPYJCS-UHFFFAOYSA-N Musk ambrette Chemical compound COC1=C([N+]([O-])=O)C(C)=C([N+]([O-])=O)C=C1C(C)(C)C SUAUILGSCPYJCS-UHFFFAOYSA-N 0.000 description 4
241000220317 Rosa Species 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
229940126214 compound 3 Drugs 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
-1 mp 133-134C Chemical compound 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
QDUGNCUWOVVCAF-UHFFFAOYSA-N 1-hydroxy-3,4,5,5,8,8-hexamethyl-6,7-dihydronaphthalene-2-carbaldehyde Chemical compound CC1(C)CCC(C)(C)C2=C1C(O)=C(C=O)C(C)=C2C QDUGNCUWOVVCAF-UHFFFAOYSA-N 0.000 description 3
ZGCGRJAPSIJUHV-UHFFFAOYSA-N 1-hydroxy-3,5,5,8,8-pentamethyl-6,7-dihydronaphthalene-2-carbaldehyde Chemical compound CC1(C)CCC(C)(C)C2=C1C(O)=C(C=O)C(C)=C2 ZGCGRJAPSIJUHV-UHFFFAOYSA-N 0.000 description 3
FACFHHMQICTXFZ-UHFFFAOYSA-N 2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethanamine Chemical compound N1=C2C=CC=CN2C(CCN)=C1C1=CC=CC=C1 FACFHHMQICTXFZ-UHFFFAOYSA-N 0.000 description 3
PSWDQTMAUUQILQ-UHFFFAOYSA-N 2-[(6-methoxy-4-methylquinazolin-2-yl)amino]-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound N1=C(C)C2=CC(OC)=CC=C2N=C1NC1=NC(=O)C(C)=C(C)N1 PSWDQTMAUUQILQ-UHFFFAOYSA-N 0.000 description 3
AATJYTRZUXEXMD-UHFFFAOYSA-N 3-ethyl-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-1-ol Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(CC)=CC=2O AATJYTRZUXEXMD-UHFFFAOYSA-N 0.000 description 3
240000002505 Pogostemon cablin Species 0.000 description 3
235000011751 Pogostemon cablin Nutrition 0.000 description 3
OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229940125796 compound 3d Drugs 0.000 description 3
239000002537 cosmetic Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
229940067137 musk ketone Drugs 0.000 description 3
XMWRWTSZNLOZFN-UHFFFAOYSA-N musk xylene Chemical group CC1=C(N(=O)=O)C(C)=C(N(=O)=O)C(C(C)(C)C)=C1N(=O)=O XMWRWTSZNLOZFN-UHFFFAOYSA-N 0.000 description 3
229940093932 potassium hydroxide Drugs 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
238000011084 recovery Methods 0.000 description 3
230000001953 sensory effect Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
240000008772 Cistus ladanifer Species 0.000 description 2
244000061408 Eugenia caryophyllata Species 0.000 description 2
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
241001263323 Maclura tinctoria Species 0.000 description 2
235000010672 Monarda didyma Nutrition 0.000 description 2
244000179970 Monarda didyma Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
240000000513 Santalum album Species 0.000 description 2
235000008632 Santalum album Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
244000028419 Styrax benzoin Species 0.000 description 2
235000000126 Styrax benzoin Nutrition 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
235000016639 Syzygium aromaticum Nutrition 0.000 description 2
244000284012 Vetiveria zizanioides Species 0.000 description 2
235000007769 Vetiveria zizanioides Nutrition 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
235000000484 citronellol Nutrition 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
238000001816 cooling Methods 0.000 description 2
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
230000005923 long-lasting effect Effects 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 2
235000012141 vanillin Nutrition 0.000 description 2
VEPOHXYIFQMVHW-PVJVQHJQSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;(2s,3s)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.O1CCN(C)[C@@H](C)[C@@H]1C1=CC=CC=C1 VEPOHXYIFQMVHW-PVJVQHJQSA-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
UNAJREJGSQDJGU-ZRDIBKRKSA-N (e)-2-methyl-1-(2,6,6-trimethylcyclohex-2-en-1-yl)pent-1-en-3-one Chemical compound CCC(=O)C(\C)=C\C1C(C)=CCCC1(C)C UNAJREJGSQDJGU-ZRDIBKRKSA-N 0.000 description 1
JZQOJFLIJNRDHK-UZPJXDOOSA-N (e)-4-[(1s,5r)-2,5,6,6-tetramethylcyclohex-2-en-1-yl]but-3-en-2-one Chemical compound C[C@@H]1CC=C(C)[C@H](\C=C\C(C)=O)C1(C)C JZQOJFLIJNRDHK-UZPJXDOOSA-N 0.000 description 1
DTWVMISUVINXEV-UHFFFAOYSA-N 1,5,6,7,8-pentamethyl-1,2,3,4-tetrahydronaphthalene Chemical compound CC1C=2C(=C(C(=C(C2CCC1)C)C)C)C DTWVMISUVINXEV-UHFFFAOYSA-N 0.000 description 1
RUGOHWJNHDFSTO-UHFFFAOYSA-N 1-hydroxy-4,5,5,8,8-pentamethyl-6,7-dihydronaphthalene-2-carbaldehyde Chemical compound CC1(C)CCC(C)(C)C2=C1C(C)=CC(C=O)=C2O RUGOHWJNHDFSTO-UHFFFAOYSA-N 0.000 description 1
JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
HSTAGCWQAIXJQM-UHFFFAOYSA-N 2,5-dichloro-2,5-dimethylhexane Chemical compound CC(C)(Cl)CCC(C)(C)Cl HSTAGCWQAIXJQM-UHFFFAOYSA-N 0.000 description 1
RRFNCPBJVPQIPP-UHFFFAOYSA-N 2,5-dichlorohexane Chemical compound CC(Cl)CCC(C)Cl RRFNCPBJVPQIPP-UHFFFAOYSA-N 0.000 description 1
ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 description 1
CEWXLFYSFOQBPC-UHFFFAOYSA-N 3,4,5,5,8,8-hexamethyl-6,7-dihydronaphthalen-1-ol Chemical compound CC1(C)CCC(C)(C)C=2C1=C(C)C(C)=CC=2O CEWXLFYSFOQBPC-UHFFFAOYSA-N 0.000 description 1
FRYUFVBGUAOIDZ-UHFFFAOYSA-N 3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-1-ol Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C)=CC=2O FRYUFVBGUAOIDZ-UHFFFAOYSA-N 0.000 description 1
RFQMOUZUNUTNTD-UHFFFAOYSA-N 3-ethyl-1-hydroxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbaldehyde Chemical compound CC1(C)CCC(C)(C)C2=C1C(O)=C(C=O)C(CC)=C2 RFQMOUZUNUTNTD-UHFFFAOYSA-N 0.000 description 1
XNBRQQXYRGHBGG-UHFFFAOYSA-N 3-ethyl-1-methoxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbaldehyde Chemical compound CC1(C)CCC(C)(C)C2=C1C(OC)=C(C=O)C(CC)=C2 XNBRQQXYRGHBGG-UHFFFAOYSA-N 0.000 description 1
YXOVIGZJPGLNGM-UHFFFAOYSA-N 5-methyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1CCCC2=C1C=CC=C2C YXOVIGZJPGLNGM-UHFFFAOYSA-N 0.000 description 1
NXJRGBYAAGIJBX-UHFFFAOYSA-N 6-(chloromethyl)-5-methoxy-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalene Chemical compound CC1(C)CCC(C)(C)C2=C1C(OC)=C(CCl)C(C)=C2 NXJRGBYAAGIJBX-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000195940 Bryophyta Species 0.000 description 1
235000005241 Cistus ladanifer Nutrition 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
235000018958 Gardenia augusta Nutrition 0.000 description 1
239000005792 Geraniol Substances 0.000 description 1
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 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
239000004869 Labdanum Substances 0.000 description 1
244000178870 Lavandula angustifolia Species 0.000 description 1
235000010663 Lavandula angustifolia Nutrition 0.000 description 1
235000015511 Liquidambar orientalis Nutrition 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
239000004870 Styrax Substances 0.000 description 1
235000008411 Sumatra benzointree Nutrition 0.000 description 1
206010042618 Surgical procedure repeated Diseases 0.000 description 1
AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 description 1
244000290333 Vanilla fragrans Species 0.000 description 1
235000009499 Vanilla fragrans Nutrition 0.000 description 1
235000012036 Vanilla tahitensis Nutrition 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
HMKKIXGYKWDQSV-KAMYIIQDSA-N alpha-Amylcinnamaldehyde Chemical compound CCCCC\C(C=O)=C\C1=CC=CC=C1 HMKKIXGYKWDQSV-KAMYIIQDSA-N 0.000 description 1
QUMXDOLUJCHOAY-UHFFFAOYSA-N alpha-methylbenzyl acetate Natural products CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 1
230000004075 alteration Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000003321 amplification Effects 0.000 description 1
235000001053 badasse Nutrition 0.000 description 1
239000002585 base Substances 0.000 description 1
229960002130 benzoin Drugs 0.000 description 1
229940007550 benzyl acetate Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
229940117916 cinnamic aldehyde Drugs 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229960000956 coumarin Drugs 0.000 description 1
235000001671 coumarin Nutrition 0.000 description 1
JRUYYVYCSJCVMP-UHFFFAOYSA-N coumarin 30 Chemical compound C1=CC=C2N(C)C(C=3C4=CC=C(C=C4OC(=O)C=3)N(CC)CC)=NC2=C1 JRUYYVYCSJCVMP-UHFFFAOYSA-N 0.000 description 1
KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 1
230000002950 deficient Effects 0.000 description 1
239000002781 deodorant agent Substances 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
229940073505 ethyl vanillin Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000002979 fabric softener Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 1
229940113087 geraniol Drugs 0.000 description 1
HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
244000056931 lavandin Species 0.000 description 1
235000009606 lavandin Nutrition 0.000 description 1
239000001102 lavandula vera Substances 0.000 description 1
235000018219 lavender Nutrition 0.000 description 1
229930007744 linalool Natural products 0.000 description 1
UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
235000011929 mousse Nutrition 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
239000012437 perfumed product Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229940067107 phenylethyl alcohol Drugs 0.000 description 1
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000013042 solid detergent Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000013589 supplement Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003760 tallow Substances 0.000 description 1
UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 description 1
229940098465 tincture Drugs 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- 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
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/18—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving halogen atoms of halogenated compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
- C07C47/57—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups polycyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
- 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
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fats And Perfumes (AREA)

CA000431610A 1982-07-02 1983-06-30 Aromatic musks Expired CA1190564A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US39484782A	1982-07-02	1982-07-02
US394,847		1982-07-02
US06/494,674 US4476040A (en)	1982-07-02	1983-05-13	Aromatic musks
US494,674		1983-05-13

Publications (1)

Publication Number	Publication Date
CA1190564A true CA1190564A (en)	1985-07-16

Family

ID=27014890

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000431610A Expired CA1190564A (en)	1982-07-02	1983-06-30	Aromatic musks

Country Status (14)

Country	Link
US (1)	US4476040A (2)
EP (1)	EP0098546B1 (2)
AU (1)	AU553475B2 (2)
BR (1)	BR8303536A (2)
CA (1)	CA1190564A (2)
DE (1)	DE3360241D1 (2)
DK (1)	DK160088C (2)
EG (1)	EG16416A (2)
ES (2)	ES523776A0 (2)
GR (1)	GR78587B (2)
IE (1)	IE55166B1 (2)
IL (1)	IL69116A0 (2)
MX (1)	MX162511A (2)
PL (2)	PL145357B1 (2)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3814180A1 (de) *	1988-04-27	1989-11-09	Basf Ag	Verfahren zur herstellung von tetralinderivaten und neue tetralinderivate
US5401720A (en) *	1993-06-18	1995-03-28	Union Camp Corporation	Alkyl tetralin aldehyde compounds

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB760667A (en) *	1953-12-14	1956-11-07	Givaudan & Cie Sa	Substituted tetrahydronaphthalenes
US2997503A (en) *	1955-01-28	1961-08-22	Givaudan Corp	Process of preparing substituted tetrahydronaphthalenes
GB786397A (en) *	1955-01-28	1957-11-20	Givaudan & Cie Sa	Improvements in and relating to substituted tetrahydronaphthalene aldehydes
US2800511A (en) *	1955-01-28	1957-07-23	Givaudan Corp	Substituted tetrahydronaphthalene aldehydes
US2802880A (en) *	1957-01-25	1957-08-13	Firmenich & Cie	Hydroxy-octahydronaphthalenes
US2912462A (en) *	1957-10-22	1959-11-10	Trubeck Lab	Substituted bicyclic decanols and decanones
US3808277A (en) *	1971-01-18	1974-04-30	Syntex Corp	2-methoxymethylene-6-methoxy-1-tetralone
US3910853A (en) *	1974-07-29	1975-10-07	Fritzsche Dodge & Olcott Inc	1,1,4,4-Tetra methyl-alkyl-nitriles-tetrahydronaphthalene perfume compositions

1983
- 1983-05-13 US US06/494,674 patent/US4476040A/en not_active Expired - Lifetime
- 1983-06-29 IL IL69116A patent/IL69116A0/xx not_active IP Right Cessation
- 1983-06-29 GR GR71798A patent/GR78587B/el unknown
- 1983-06-30 MX MX197896A patent/MX162511A/es unknown
- 1983-06-30 CA CA000431610A patent/CA1190564A/en not_active Expired
- 1983-07-01 BR BR8303536A patent/BR8303536A/pt not_active IP Right Cessation
- 1983-07-01 DK DK304283A patent/DK160088C/da active
- 1983-07-01 ES ES523776A patent/ES523776A0/es active Granted
- 1983-07-01 EP EP83106438A patent/EP0098546B1/en not_active Expired
- 1983-07-01 IE IE1557/83A patent/IE55166B1/en not_active IP Right Cessation
- 1983-07-01 DE DE8383106438T patent/DE3360241D1/de not_active Expired
- 1983-07-01 PL PL1983261804A patent/PL145357B1/pl unknown
- 1983-07-01 PL PL1983242780A patent/PL141581B1/pl unknown
- 1983-07-02 EG EG407/83A patent/EG16416A/xx active
- 1983-07-04 AU AU16530/83A patent/AU553475B2/en not_active Ceased
1985
- 1985-01-02 ES ES539324A patent/ES539324A0/es active Granted

Also Published As

Publication number	Publication date
MX162511A (es)	1991-05-15
EG16416A (en)	1989-06-30
PL141581B1 (en)	1987-08-31
DK160088C (da)	1991-06-24
IE55166B1 (en)	1990-06-20
AU553475B2 (en)	1986-07-17
PL242780A1 (en)	1984-07-02
PL145357B1 (en)	1988-09-30
EP0098546B1 (en)	1985-06-05
ES8504656A1 (es)	1985-04-16
IL69116A0 (en)	1983-10-31
EP0098546A1 (en)	1984-01-18
GR78587B (2)	1984-09-27
DK304283A (da)	1984-01-03
IE831557L (en)	1984-01-02
US4476040A (en)	1984-10-09
ES8603367A1 (es)	1985-12-16
DE3360241D1 (en)	1985-07-11
DK160088B (da)	1991-01-28
AU1653083A (en)	1984-01-05
ES523776A0 (es)	1985-04-16
BR8303536A (pt)	1984-02-14
ES539324A0 (es)	1985-12-16
DK304283D0 (da)	1983-07-01

Legal Events

Date	Code	Title	Description
2002-07-17	MKEC	Expiry (correction)
2003-06-30	MKEX	Expiry

Publication	Publication Date	Title
KR940007118B1 (ko)	1994-08-06	출발 물질로서 1종 이상의 카로티노이드를 기재로 하는 향미료 및 향료의 제조 방법
MXPA06005893A (es)	2006-06-27	Compuestos fragantes de almizcle.
US3962148A (en)	1976-06-08	Odorant compositions containing 4,4,6-trimethyl-2-cyclohexenone
US4308179A (en)	1981-12-29	Perfumed compositions
US4490284A (en)	1984-12-25	1,1-Di(C1 -C6 -alkyl)-2-phenyl-ethane derivatives as perfuming ingredients
US4880775A (en)	1989-11-14	Poly-alkylated benzodioxin musk compositions
US4097396A (en)	1978-06-27	Soaps and detergents containing alpha-oxy(oxo)sulfides as perfumes
CA1190564A (en)	1985-07-16	Aromatic musks
US4605778A (en)	1986-08-12	Process for the preparation of aromatic musks
US4041084A (en)	1977-08-09	Tricyclic alcohols
US4311852A (en)	1982-01-19	Oxygen containing derivatives of tricyclo[6.2.1.02,7 ]undecane
US4139484A (en)	1979-02-13	Process for altering, modifying or enhancing the aroma of detergents with substituted bicyclooctene derivatives
JPS62898B2 (2)	1987-01-10
US3981924A (en)	1976-09-21	Diels-Alder adduct product
JPH02188550A (ja)	1990-07-24	新規な発香化合物
JPS648631B2 (2)	1989-02-14
US5504066A (en)	1996-04-02	Pentene derivatives, their production and use
JPH05262757A (ja)	1993-10-12	環状イソロンギホラノン−ケタール類、その製法及び使用法
US4129569A (en)	1978-12-12	Cyclic oxazo derivatives
US4221679A (en)	1980-09-09	Norbornyl-substituted pyran perfumes
US4197246A (en)	1980-04-08	Novel norcamphanyl-substituted pyrans, method for their synthesis and use thereof in perfumery
US4392993A (en)	1983-07-12	Alicyclic unsaturated compounds, their preparation and use of same as perfume ingredients
US4485828A (en)	1984-12-04	Use of substituted methyl isopropyl cyclohexenones in augmenting or enhancing the aroma or taste of smoking tobacco compositions and smoking tobacco article components
US4483786A (en)	1984-11-20	Nitrile musk composition
US3996170A (en)	1976-12-07	6-N-Butyl alpha pyrone perfumes