JPS6284194A - 香気性にすぐれかつ感作性の低いイランイラン油の製造法 - Google Patents
香気性にすぐれかつ感作性の低いイランイラン油の製造法Info
- Publication number
- JPS6284194A JPS6284194A JP22534185A JP22534185A JPS6284194A JP S6284194 A JPS6284194 A JP S6284194A JP 22534185 A JP22534185 A JP 22534185A JP 22534185 A JP22534185 A JP 22534185A JP S6284194 A JPS6284194 A JP S6284194A
- Authority
- JP
- Japan
- Prior art keywords
- ylang
- oil
- essential oil
- distilled
- compound
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000796 flavoring agent Substances 0.000 title description 2
- 235000019634 flavors Nutrition 0.000 title 1
- 230000035945 sensitivity Effects 0.000 title 1
- 239000000341 volatile oil Substances 0.000 claims description 70
- 239000003921 oil Substances 0.000 claims description 42
- 240000007436 Cananga odorata Species 0.000 claims description 41
- 239000000126 substance Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000005292 vacuum distillation Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 39
- 239000003205 fragrance Substances 0.000 description 21
- 230000008313 sensitization Effects 0.000 description 13
- ITDOFWOJEDZPCF-AATRIKPKSA-N 2-methoxy-4-[7-methoxy-3-methyl-5-[(e)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol Chemical class O1C=2C(OC)=CC(\C=C\C)=CC=2C(C)C1C1=CC=C(O)C(OC)=C1 ITDOFWOJEDZPCF-AATRIKPKSA-N 0.000 description 12
- 206010070834 Sensitisation Diseases 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 238000009835 boiling Methods 0.000 description 9
- 230000002688 persistence Effects 0.000 description 8
- 230000001235 sensitizing effect Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 6
- ITDOFWOJEDZPCF-UHFFFAOYSA-N dl-Dehydrodiisoeugenol Natural products O1C=2C(OC)=CC(C=CC)=CC=2C(C)C1C1=CC=C(O)C(OC)=C1 ITDOFWOJEDZPCF-UHFFFAOYSA-N 0.000 description 6
- ITDOFWOJEDZPCF-CWTRNNRKSA-N Dehydro-diisoeugenol Natural products COC1=CC(=CC=2[C@H]([C@@H](OC=21)C1=CC(=C(C=C1)O)OC)C)C=CC ITDOFWOJEDZPCF-CWTRNNRKSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- 206010070835 Skin sensitisation Diseases 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 231100000370 skin sensitisation Toxicity 0.000 description 2
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- 235000007571 Cananga odorata Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical class COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 231100000458 skin sensitization testing Toxicity 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22534185A JPS6284194A (ja) | 1985-10-08 | 1985-10-08 | 香気性にすぐれかつ感作性の低いイランイラン油の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22534185A JPS6284194A (ja) | 1985-10-08 | 1985-10-08 | 香気性にすぐれかつ感作性の低いイランイラン油の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6284194A true JPS6284194A (ja) | 1987-04-17 |
| JPH0226669B2 JPH0226669B2 (en:Method) | 1990-06-12 |
Family
ID=16827823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22534185A Granted JPS6284194A (ja) | 1985-10-08 | 1985-10-08 | 香気性にすぐれかつ感作性の低いイランイラン油の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6284194A (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01254628A (ja) * | 1988-04-05 | 1989-10-11 | Shiseido Co Ltd | 意識水準を鎮静させる吸入投与用組成物 |
| JPH01254629A (ja) * | 1988-04-05 | 1989-10-11 | Shiseido Co Ltd | 意識水準を高揚させる効果をもつ室内用芳香剤 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5898400A (ja) * | 1981-12-07 | 1983-06-11 | 高砂香料工業株式会社 | 低感作性イランイラン油の製造法 |
-
1985
- 1985-10-08 JP JP22534185A patent/JPS6284194A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5898400A (ja) * | 1981-12-07 | 1983-06-11 | 高砂香料工業株式会社 | 低感作性イランイラン油の製造法 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01254628A (ja) * | 1988-04-05 | 1989-10-11 | Shiseido Co Ltd | 意識水準を鎮静させる吸入投与用組成物 |
| JPH01254629A (ja) * | 1988-04-05 | 1989-10-11 | Shiseido Co Ltd | 意識水準を高揚させる効果をもつ室内用芳香剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0226669B2 (en:Method) | 1990-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| R371 | Transfer withdrawn |
Free format text: JAPANESE INTERMEDIATE CODE: R371 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| EXPY | Cancellation because of completion of term |