JPH0150360B2 - - Google Patents

Info

Publication number: JPH0150360B2
Authority: JP; Japan
Prior art keywords: oil; distilled; essential oil; bergapten; distillation residue
Prior art date: 1982-04-05
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

JP5704482A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58173195A (ja

Inventor

Hiroshi Kakishima

Takashi Abe

Masayoshi Inui

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.)

Kanebo Ltd

Original Assignee

Kanebo Ltd

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.)

1982-04-05

Filing date

1982-04-05

Publication date

1989-10-30

1982-04-05 Application filed by Kanebo Ltd filed Critical Kanebo Ltd

1982-04-05 Priority to JP5704482A priority Critical patent/JPS58173195A/ja

1983-10-12 Publication of JPS58173195A publication Critical patent/JPS58173195A/ja

1989-10-30 Publication of JPH0150360B2 publication Critical patent/JPH0150360B2/ja

Status Granted legal-status Critical Current

Links

BGEBZHIAGXMEMV-UHFFFAOYSA-N 5-methoxypsoralen Chemical compound O1C(=O)C=CC2=C1C=C1OC=CC1=C2OC BGEBZHIAGXMEMV-UHFFFAOYSA-N 0.000 claims description 84
239000000341 volatile oil Substances 0.000 claims description 61
238000004821 distillation Methods 0.000 claims description 49
229960002045 bergapten Drugs 0.000 claims description 42
KGZDKFWCIPZMRK-UHFFFAOYSA-N bergapten Natural products COC1C2=C(Cc3ccoc13)C=CC(=O)O2 KGZDKFWCIPZMRK-UHFFFAOYSA-N 0.000 claims description 42
DBMJZOMNXBSRED-UHFFFAOYSA-N Bergamottin Natural products O1C(=O)C=CC2=C1C=C1OC=CC1=C2OCC=C(C)CCC=C(C)C DBMJZOMNXBSRED-UHFFFAOYSA-N 0.000 claims description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
239000000284 extract Substances 0.000 claims description 22
239000002904 solvent Substances 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
230000009467 reduction Effects 0.000 claims description 14
239000012279 sodium borohydride Substances 0.000 claims description 14
229910000033 sodium borohydride Inorganic materials 0.000 claims description 14
206010034972 Photosensitivity reaction Diseases 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
208000007578 phototoxic dermatitis Diseases 0.000 claims description 13
231100000018 phototoxicity Toxicity 0.000 claims description 13
230000002209 hydrophobic effect Effects 0.000 claims description 11
239000012454 non-polar solvent Substances 0.000 claims description 9
125000001931 aliphatic group Chemical group 0.000 claims description 8
QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
238000005406 washing Methods 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 23
ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical class C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 description 20
235000019441 ethanol Nutrition 0.000 description 19
239000003921 oil Substances 0.000 description 17
235000019198 oils Nutrition 0.000 description 17
235000019501 Lemon oil Nutrition 0.000 description 13
239000010501 lemon oil Substances 0.000 description 13
238000003756 stirring Methods 0.000 description 12
230000007935 neutral effect Effects 0.000 description 11
239000003208 petroleum Substances 0.000 description 11
239000001279 citrus aurantifolia swingle expressed oil Substances 0.000 description 10
238000000034 method Methods 0.000 description 10
VXGRJERITKFWPL-UHFFFAOYSA-N 4',5'-Dihydropsoralen Natural products C1=C2OC(=O)C=CC2=CC2=C1OCC2 VXGRJERITKFWPL-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
231100001085 no phototoxicity Toxicity 0.000 description 9
238000010992 reflux Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
235000019502 Orange oil Nutrition 0.000 description 7
239000012230 colorless oil Substances 0.000 description 7
239000010502 orange oil Substances 0.000 description 7
238000004458 analytical method Methods 0.000 description 5
-1 colognes Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
206010015150 Erythema Diseases 0.000 description 4
230000008859 change Effects 0.000 description 4
231100000321 erythema Toxicity 0.000 description 4
231100001183 nonphototoxic Toxicity 0.000 description 4
231100000760 phototoxic Toxicity 0.000 description 4
230000001953 sensory effect Effects 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
230000002411 adverse Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000002304 perfume Substances 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
241000283977 Oryctolagus Species 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000010651 grapefruit oil Substances 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
SQBBOVROCFXYBN-UHFFFAOYSA-N methoxypsoralen Natural products C1=C2OC(=O)C(OC)=CC2=CC2=C1OC=C2 SQBBOVROCFXYBN-UHFFFAOYSA-N 0.000 description 2
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
FMHHVULEAZTJMA-UHFFFAOYSA-N trioxsalen Chemical compound CC1=CC(=O)OC2=C1C=C1C=C(C)OC1=C2C FMHHVULEAZTJMA-UHFFFAOYSA-N 0.000 description 2
TUTMEHZVWWQNMW-UHFFFAOYSA-N 5-methylfuro[3,2-g]chromen-7-one Chemical compound C1=C2OC=CC2=CC2=C1OC(=O)C=C2C TUTMEHZVWWQNMW-UHFFFAOYSA-N 0.000 description 1
BUNGCZLFHHXKBX-UHFFFAOYSA-N 8-methoxypsoralen Natural products C1=CC(=O)OC2=C1C=C1CCOC1=C2OC BUNGCZLFHHXKBX-UHFFFAOYSA-N 0.000 description 1
241000238876 Acari Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical compound C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 description 1
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001447 alkali salts Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007547 defect Effects 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
239000011888 foil Substances 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000006210 lotion Substances 0.000 description 1
229960004469 methoxsalen Drugs 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
235000021003 saturated fats Nutrition 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Fats And Perfumes (AREA)

JP5704482A 1982-04-05 1982-04-05 光毒性を有しない天然精油の製造法 Granted JPS58173195A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP5704482A JPS58173195A (ja)	1982-04-05	1982-04-05	光毒性を有しない天然精油の製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP5704482A JPS58173195A (ja)	1982-04-05	1982-04-05	光毒性を有しない天然精油の製造法

Publications (2)

Publication Number	Publication Date
JPS58173195A JPS58173195A (ja)	1983-10-12
JPH0150360B2 true JPH0150360B2 (2)	1989-10-30

Family

ID=13044442

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5704482A Granted JPS58173195A (ja)	1982-04-05	1982-04-05	光毒性を有しない天然精油の製造法

Country Status (1)

Country	Link
JP (1)	JPS58173195A (2)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6384457A (ja) *	1986-09-29	1988-04-15	Nagaoka Koryo Kk	光毒性を有しないレモン油の製造法

1982
- 1982-04-05 JP JP5704482A patent/JPS58173195A/ja active Granted

Also Published As

Publication number	Publication date
JPS58173195A (ja)	1983-10-12

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Blackburne et al.	1972	Terpenoid chemistry. XIX. Dehydro-and Dehydroiso-myodesmone, toxic furanoid sesquiterpene ketones from Myoporum deserti
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