JPH0363238A - 芳香性材料および該芳香性材料の製造方法、および該芳香性材料を含む香料 - Google Patents
芳香性材料および該芳香性材料の製造方法、および該芳香性材料を含む香料Info
- Publication number
- JPH0363238A JPH0363238A JP32622089A JP32622089A JPH0363238A JP H0363238 A JPH0363238 A JP H0363238A JP 32622089 A JP32622089 A JP 32622089A JP 32622089 A JP32622089 A JP 32622089A JP H0363238 A JPH0363238 A JP H0363238A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- carbon
- structural formula
- tables
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title description 5
- 125000004122 cyclic group Chemical group 0.000 title 1
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- OGCGGWYLHSJRFY-UHFFFAOYSA-N alpha-campholenaldehyde Chemical compound CC1=CCC(CC=O)C1(C)C OGCGGWYLHSJRFY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 5
- 239000003205 fragrance Substances 0.000 claims description 5
- -1 Acetoacetic acid ester Chemical class 0.000 claims description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 1
- 239000002304 perfume Substances 0.000 abstract description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 abstract description 4
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011780 sodium chloride Substances 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229940125782 compound 2 Drugs 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 235000019645 odor Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000006679 Mentha X verticillata Nutrition 0.000 description 2
- 235000002899 Mentha suaveolens Nutrition 0.000 description 2
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 240000000513 Santalum album Species 0.000 description 2
- 235000008632 Santalum album Nutrition 0.000 description 2
- 229960000846 camphor Drugs 0.000 description 2
- 229930008380 camphor Natural products 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000002085 persistent effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- BAVONGHXFVOKBV-ZJUUUORDSA-N (-)-trans-carveol Natural products CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1 BAVONGHXFVOKBV-ZJUUUORDSA-N 0.000 description 1
- WINCSBAYCULVDU-UHFFFAOYSA-N 1,1,2-trimethylcyclopentane Chemical group CC1CCCC1(C)C WINCSBAYCULVDU-UHFFFAOYSA-N 0.000 description 1
- UENOQWSWMYJKIW-UHFFFAOYSA-N 1,2,2-trimethylcyclohexan-1-ol Chemical compound CC1(C)CCCCC1(C)O UENOQWSWMYJKIW-UHFFFAOYSA-N 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-pentanol Substances CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 241000944022 Amyris Species 0.000 description 1
- 239000004857 Balsam Substances 0.000 description 1
- 101800004637 Communis Proteins 0.000 description 1
- 101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
- 235000019123 Fortunella margarita Nutrition 0.000 description 1
- 244000089759 Fortunella margarita Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 244000018716 Impatiens biflora Species 0.000 description 1
- 241000168482 Tetrataenium canescens Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003788 bath preparation Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 239000001342 boswellia carteri birdw. oil Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229930007646 carveol Natural products 0.000 description 1
- 125000001150 carveol group Chemical group 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000035597 cooling sensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- BAVONGHXFVOKBV-UHFFFAOYSA-N exo-carveol Natural products CC(=C)C1CC=C(C)C(O)C1 BAVONGHXFVOKBV-UHFFFAOYSA-N 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000001683 mentha spicata herb oil Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 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
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000019721 spearmint oil Nutrition 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32622089A JPH0363238A (ja) | 1989-12-18 | 1989-12-18 | 芳香性材料および該芳香性材料の製造方法、および該芳香性材料を含む香料 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32622089A JPH0363238A (ja) | 1989-12-18 | 1989-12-18 | 芳香性材料および該芳香性材料の製造方法、および該芳香性材料を含む香料 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54501355A Division JPH0222052B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-11-02 | 1979-07-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0363238A true JPH0363238A (ja) | 1991-03-19 |
| JPH0466851B2 JPH0466851B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-10-26 |
Family
ID=18185332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32622089A Granted JPH0363238A (ja) | 1989-12-18 | 1989-12-18 | 芳香性材料および該芳香性材料の製造方法、および該芳香性材料を含む香料 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0363238A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2017188314A1 (ja) * | 2016-04-28 | 2018-05-10 | 日本精工株式会社 | 潤滑剤劣化検出装置、潤滑剤劣化状態評価方法 |
-
1989
- 1989-12-18 JP JP32622089A patent/JPH0363238A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2017188314A1 (ja) * | 2016-04-28 | 2018-05-10 | 日本精工株式会社 | 潤滑剤劣化検出装置、潤滑剤劣化状態評価方法 |
| JP2019049540A (ja) * | 2016-04-28 | 2019-03-28 | 日本精工株式会社 | 潤滑剤劣化検出装置、潤滑剤劣化状態評価方法 |
| US10890575B2 (en) | 2016-04-28 | 2021-01-12 | Nsk Ltd. | Lubricant deterioration detection device and lubricant deterioration state evaluation method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0466851B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-10-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6055484B2 (ja) | オクタヒドロ−テトウメチルアセトナフトンの有効な芳香量を必須成分として含有している香料組成物 | |
| DE69527045T2 (de) | Tetrahydrofurane und tetrahydropyrane | |
| US4308179A (en) | Perfumed compositions | |
| JP2610309B2 (ja) | 新規香料 | |
| US4188310A (en) | Substituted cyclic alcohols, methods of preparing and compositions containing same | |
| JP2010500421A (ja) | シクロペンタン／シクロペンテンアルデヒド誘導体またはシクロペンタン／シクロペンテンケトン誘導体および香り物質としてのそれらの使用 | |
| JPS59176207A (ja) | １−ｃ２，６，６−トリメチルシクロヘキシル）−ヘキサン−３−オ−ル異性体混合物の製造法 | |
| US4341666A (en) | Perfuming with oxygen containing derivatives of tricyclo[6.2.1.02,7 ]un | |
| JPS648040B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPH0363238A (ja) | 芳香性材料および該芳香性材料の製造方法、および該芳香性材料を含む香料 | |
| US3996169A (en) | Perfume uses of tricyclic alcohols and processes | |
| DE60209664T2 (de) | Duftstoffzusammensetzung enthaltend 3-(3-Hexenyl)-2-Cyclopentenon | |
| JPS62298558A (ja) | シクロヘキサン−、シクロヘキセン−およびシクロヘキサジエン−ビシクロ〔２．２．１〕ヘプタン−および−ビシクロ〔２．２．１〕ヘプテンカルボン酸エステル、ならびに香料成分としての利用 | |
| DE2143232B2 (de) | 2 (T Hydroxymethylathyl)-5 methyl 5 vinyl tetrahydrofuran und deren Ver wendung als Riechstoff | |
| CA1128537A (en) | Norbornyl-substituted pyrans, method for their synthesis and use thereof in perfumery | |
| US4162266A (en) | Trimethyl-acetyl octalins, process for making and fragrance compositions containing same | |
| DE69604821T2 (de) | Parfümgrundzusammenstellung | |
| JP4859826B2 (ja) | フレグランス組成物の製造に好適な三置換フラン | |
| JPH01207252A (ja) | ４−イソブチルシクロヘキシルメタノールおよびそれを含有する香料組成物 | |
| JPH01160936A (ja) | 新規な発香化合物 | |
| JPS62226943A (ja) | 置換エチル基含有ノルボルネン誘導体およびこれを含む香料組成物 | |
| JPH0222052B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPS625402B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE3443536A1 (de) | Methylsubstituierte bicyclo(2.2.1)heptan-derivate und deren verwendung als riechstoffe | |
| DE2507778A1 (de) | Verwendung von dichlorcyclopropanderivaten als riechstoffe |