JPH0421652B2 - - Google Patents
Info
- Publication number
- JPH0421652B2 JPH0421652B2 JP15066984A JP15066984A JPH0421652B2 JP H0421652 B2 JPH0421652 B2 JP H0421652B2 JP 15066984 A JP15066984 A JP 15066984A JP 15066984 A JP15066984 A JP 15066984A JP H0421652 B2 JPH0421652 B2 JP H0421652B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- fragrance
- formula
- dcpd
- solvent
- 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
- 239000003205 fragrance Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- -1 2-formylpropyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000003965 capillary gas chromatography Methods 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- NCWQJOGVLLNWEO-UHFFFAOYSA-N methylsilicon Chemical compound [Si]C NCWQJOGVLLNWEO-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 1
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 1
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 description 1
- YXVSKJDFNJFXAJ-UHFFFAOYSA-N 4-cyclohexyl-2-methylbutan-2-ol Chemical compound CC(C)(O)CCC1=CC=CC=C1 YXVSKJDFNJFXAJ-UHFFFAOYSA-N 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- IETKMTGYQIVLRF-UHFFFAOYSA-N carbon monoxide;rhodium;triphenylphosphane Chemical compound [Rh].[O+]#[C-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IETKMTGYQIVLRF-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- GVRWIAHBVAYKIZ-UHFFFAOYSA-N dec-3-ene Chemical compound CCCCCCC=CCC GVRWIAHBVAYKIZ-UHFFFAOYSA-N 0.000 description 1
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000001148 ferula galbaniflua oil terpeneless Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15066984A JPS6130546A (ja) | 1984-07-20 | 1984-07-20 | ８−〔２′（又は３′）−ホルミルプロポキシ〕トリシクロ〔５．２．１．０↑２’↑６〕デカ−３（又は４）−エン及びこれを含有する香料組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15066984A JPS6130546A (ja) | 1984-07-20 | 1984-07-20 | ８−〔２′（又は３′）−ホルミルプロポキシ〕トリシクロ〔５．２．１．０↑２’↑６〕デカ−３（又は４）−エン及びこれを含有する香料組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6130546A JPS6130546A (ja) | 1986-02-12 |
| JPH0421652B2 true JPH0421652B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-04-13 |
Family
ID=15501886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15066984A Granted JPS6130546A (ja) | 1984-07-20 | 1984-07-20 | ８−〔２′（又は３′）−ホルミルプロポキシ〕トリシクロ〔５．２．１．０↑２’↑６〕デカ−３（又は４）−エン及びこれを含有する香料組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6130546A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018168075A1 (ja) | 2017-03-14 | 2018-09-20 | 株式会社村田製作所 | 正極、電池、電池パック、電子機器、電動車両、蓄電装置および電力システム |
-
1984
- 1984-07-20 JP JP15066984A patent/JPS6130546A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018168075A1 (ja) | 2017-03-14 | 2018-09-20 | 株式会社村田製作所 | 正極、電池、電池パック、電子機器、電動車両、蓄電装置および電力システム |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6130546A (ja) | 1986-02-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6255276B1 (en) | Odorant compositions containing macrocycles and processes for manufacturing the same | |
| US4266075A (en) | Bicyclic aldehyde derivatives, their use as perfuming and flavoring ingredients and process for their preparation | |
| US3716498A (en) | Novel fragrance compositions | |
| GB1591098A (en) | Substituted cyclohexanones as falvour and fragrance materials | |
| US3953377A (en) | Ethyl-2-trans-4-cis undecadienoate, ethyl-2-trans-4-cis dodecadienoate and ethyl-2-decadienoate perfume compositions | |
| US4076749A (en) | Substituted acetonaphthones, processes for preparing same, uses of same in perfumery, and intermediates used in said processes | |
| US4395370A (en) | Branched chain alkenyl methyl carbonates, uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles and formate intermediates useful in preparing same | |
| US3929677A (en) | Perfume compositions and perfurme articles containing one isomer of an octahydrotetramethyl acetonaphthone | |
| US4007137A (en) | Process for producing mixture containing 4-(4-methyl-4-hydroxyamyl)Δ3 -cyclohexenecarboxaldehyde, product produced, and its perfume uses | |
| TWI403498B (zh) | ６，８，１０-十一碳三烯-３或４-酮及香料組成物 | |
| US4229324A (en) | Tricyclo-α,β-unsaturated aldehyde | |
| ES2320207T3 (es) | Compuestos organicos. | |
| JP2602811B2 (ja) | トリメチルシクロペンテン誘導体、その製造法および芳香組成物 | |
| US3996169A (en) | Perfume uses of tricyclic alcohols and processes | |
| JPS648040B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPH0421652B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CH637359A5 (fr) | Derives de 8-exo-hydroxymethyl-endo-tricyclo(5.2.1.o(2,6))-decane. | |
| US6180814B1 (en) | Nitriles and aldehydes derived from 3-isopropenyl-1,2-dimethyl-1-cyclopentanol and their use in perfumery | |
| US4104202A (en) | Perfume compositions and process for preparing same | |
| US4661285A (en) | Balsamic fragrance composition and process for preparation | |
| EP0882697B1 (fr) | Composés parfumants à odeur boisée, fruitée | |
| US5002929A (en) | Derivatives of trimethylbicyclo-[4.3.0]-nonane, useful as perfumes | |
| US4014823A (en) | π-Tricyclene-9-alkanone perfumes | |
| US3816534A (en) | 14-oxobicyclo(10.4.0)hexadec-1(12)-ene,14-oxobicyclo(10.4.0)hexadec-12-ene,14-oxobicyclo(10.4.0)-hexadecane and process for their preparation | |
| EP0282798B1 (fr) | Alcools aliphatiques bicycliques et leur utilisation à titre d'ingrédients parfumants |