JPS61266497A - 低接触感作原性モス油及びその製造法 - Google Patents
低接触感作原性モス油及びその製造法Info
- Publication number
- JPS61266497A JPS61266497A JP10682785A JP10682785A JPS61266497A JP S61266497 A JPS61266497 A JP S61266497A JP 10682785 A JP10682785 A JP 10682785A JP 10682785 A JP10682785 A JP 10682785A JP S61266497 A JPS61266497 A JP S61266497A
- Authority
- JP
- Japan
- Prior art keywords
- oil
- treatment
- oakmoss
- moss
- sensitization
- 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 description 4
- 238000011282 treatment Methods 0.000 claims description 134
- 206010070834 Sensitisation Diseases 0.000 claims description 68
- 230000008313 sensitization Effects 0.000 claims description 68
- 239000003513 alkali Substances 0.000 claims description 35
- 238000004440 column chromatography Methods 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 31
- 238000005227 gel permeation chromatography Methods 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 26
- 230000001235 sensitizing effect Effects 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 238000009826 distribution Methods 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 217
- 235000019198 oils Nutrition 0.000 description 217
- 238000012360 testing method Methods 0.000 description 70
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
- 238000005984 hydrogenation reaction Methods 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000000926 separation method Methods 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 18
- 230000001953 sensory effect Effects 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 231100000202 sensitizing Toxicity 0.000 description 15
- 241000218645 Cedrus Species 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 230000006698 induction Effects 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003205 fragrance Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 206010015150 Erythema Diseases 0.000 description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 231100000321 erythema Toxicity 0.000 description 6
- 238000005194 fractionation Methods 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 5
- 210000003491 skin Anatomy 0.000 description 5
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 208000026935 allergic disease Diseases 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- OVYTZAASVAZITK-UHFFFAOYSA-M sodium;ethanol;hydroxide Chemical compound [OH-].[Na+].CCO OVYTZAASVAZITK-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 2
- YLOYKYXNDHOHHT-UHFFFAOYSA-N Atranorin Chemical compound CC1=C(O)C(C(=O)OC)=C(C)C=C1OC(=O)C1=C(C)C=C(O)C(C=O)=C1O YLOYKYXNDHOHHT-UHFFFAOYSA-N 0.000 description 2
- 241000195940 Bryophyta Species 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 206010012442 Dermatitis contact Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000019571 color Nutrition 0.000 description 2
- 208000010247 contact dermatitis Diseases 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000011929 mousse Nutrition 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000039 preparative column chromatography Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- WXIWFYPSEZFDBC-UHFFFAOYSA-N Baeomycessaeure-methylester Natural products COC(=O)c1c(C)cc(OC(=O)c2c(C)cc(OC)c(C=O)c2O)c(C)c1O WXIWFYPSEZFDBC-UHFFFAOYSA-N 0.000 description 1
- 241001133489 Cetrariastrum Species 0.000 description 1
- 241000543381 Cliftonia monophylla Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000004873 Evernia prunastri Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000005265 Lupinus mutabilis Species 0.000 description 1
- 235000008755 Lupinus mutabilis Nutrition 0.000 description 1
- 241000590428 Panacea Species 0.000 description 1
- 235000019095 Sechium edule Nutrition 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- CLXBGZHFHKNPHQ-UHFFFAOYSA-N atranorin Natural products COC(=O)c1c(C)cc(OC(=O)c2c(C)c(O)cc(C=O)c2O)c(C)c1O CLXBGZHFHKNPHQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- -1 platinum metals Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000458 skin sensitization testing Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10682785A JPS61266497A (ja) | 1985-05-21 | 1985-05-21 | 低接触感作原性モス油及びその製造法 |
| EP86106811A EP0202647B1 (en) | 1985-05-21 | 1986-05-20 | A process of obtaining a hypo-allergenic moss oil |
| DE8686106811T DE3682821D1 (de) | 1985-05-21 | 1986-05-20 | Verfahren zur herstellung eines hypoallergenischen moosoeles. |
| CA000509504A CA1273363A (en) | 1985-05-21 | 1986-05-20 | Hypo-allergenic moss oil and production process thereof |
| US06/864,934 US4663080A (en) | 1985-05-21 | 1986-05-20 | Hypo-allergenic moss oil and production process thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10682785A JPS61266497A (ja) | 1985-05-21 | 1985-05-21 | 低接触感作原性モス油及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61266497A true JPS61266497A (ja) | 1986-11-26 |
| JPH0532440B2 JPH0532440B2 (enrdf_load_stackoverflow) | 1993-05-17 |
Family
ID=14443598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10682785A Granted JPS61266497A (ja) | 1985-05-21 | 1985-05-21 | 低接触感作原性モス油及びその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61266497A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61266498A (ja) * | 1985-05-21 | 1986-11-26 | 株式会社資生堂 | 低接触感作原性モス油の製造法 |
| JPS6213497A (ja) * | 1985-07-12 | 1987-01-22 | 株式会社資生堂 | 低接触感作原性モス油及びその製造法 |
| JP2014076984A (ja) * | 2012-09-19 | 2014-05-01 | Kansai Univ | 美白剤 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5764608A (en) * | 1980-10-06 | 1982-04-19 | Shiseido Co Ltd | Preparation of low contact sensitinogenic jasmine oil |
-
1985
- 1985-05-21 JP JP10682785A patent/JPS61266497A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5764608A (en) * | 1980-10-06 | 1982-04-19 | Shiseido Co Ltd | Preparation of low contact sensitinogenic jasmine oil |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61266498A (ja) * | 1985-05-21 | 1986-11-26 | 株式会社資生堂 | 低接触感作原性モス油の製造法 |
| JPS6213497A (ja) * | 1985-07-12 | 1987-01-22 | 株式会社資生堂 | 低接触感作原性モス油及びその製造法 |
| JP2014076984A (ja) * | 2012-09-19 | 2014-05-01 | Kansai Univ | 美白剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0532440B2 (enrdf_load_stackoverflow) | 1993-05-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |