DE2629000A1 - Verwendung alkylsubstituierter 1,4-dioxane als riechstoffe, sowie diese enthaltende riechstoffkompositionen - Google Patents
Verwendung alkylsubstituierter 1,4-dioxane als riechstoffe, sowie diese enthaltende riechstoffkompositionenInfo
- Publication number
- DE2629000A1 DE2629000A1 DE19762629000 DE2629000A DE2629000A1 DE 2629000 A1 DE2629000 A1 DE 2629000A1 DE 19762629000 DE19762629000 DE 19762629000 DE 2629000 A DE2629000 A DE 2629000A DE 2629000 A1 DE2629000 A1 DE 2629000A1
- Authority
- DE
- Germany
- Prior art keywords
- dioxane
- methyl
- alkyl
- substituted
- dioxanes
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims description 25
- 239000003205 fragrance Substances 0.000 title claims description 17
- 150000000094 1,4-dioxanes Chemical class 0.000 title claims description 16
- 239000000126 substance Substances 0.000 title description 2
- -1 alkyl radical Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- PPMZNKNFXRYHGU-UHFFFAOYSA-N 2-butyl-5-methyl-1,4-dioxane Chemical compound CCCCC1COC(C)CO1 PPMZNKNFXRYHGU-UHFFFAOYSA-N 0.000 claims description 3
- ONIGTGNUBGLUSZ-UHFFFAOYSA-N 2-butyl-6-methyl-1,4-dioxane Chemical compound CCCCC1COCC(C)O1 ONIGTGNUBGLUSZ-UHFFFAOYSA-N 0.000 claims description 3
- GJGHXDNCFWXLHO-UHFFFAOYSA-N 2-decyl-6-methyl-1,4-dioxane Chemical compound CCCCCCCCCCC1COCC(C)O1 GJGHXDNCFWXLHO-UHFFFAOYSA-N 0.000 claims description 3
- YRKZBYMHIFYSPD-UHFFFAOYSA-N 2-hexyl-6-methyl-1,4-dioxane Chemical compound CCCCCCC1COCC(C)O1 YRKZBYMHIFYSPD-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- OOIQUBBMZTWODB-UHFFFAOYSA-N 2,3,4a,5,6,7,8,9,10,10a-decahydrocycloocta[b][1,4]dioxine Chemical compound C1CCCCCC2OCCOC21 OOIQUBBMZTWODB-UHFFFAOYSA-N 0.000 claims description 2
- KEGVAACIFRAGRQ-UHFFFAOYSA-N 2,3,4a,5,6,7,8,9,10,11,12,13,14,14a-tetradecahydrocyclododeca[b][1,4]dioxine Chemical compound C1CCCCCCCCCC2OCCOC21 KEGVAACIFRAGRQ-UHFFFAOYSA-N 0.000 claims description 2
- MSNOXCSKQGUVDN-UHFFFAOYSA-N 2-hexyl-5-methyl-1,4-dioxane Chemical compound CCCCCCC1COC(C)CO1 MSNOXCSKQGUVDN-UHFFFAOYSA-N 0.000 claims description 2
- XNWDFGKFPDNZEA-UHFFFAOYSA-N 5-decyl-2,3-dimethyl-1,4-dioxane Chemical compound CCCCCCCCCCC1COC(C)C(C)O1 XNWDFGKFPDNZEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical class O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 claims 1
- VZTAPYJPDJZGFG-UHFFFAOYSA-N 3-methyl-2,3,4a,5,6,7,8,9,10,10a-decahydrocycloocta[b][1,4]dioxine Chemical compound C1CCCCCC2OC(C)COC21 VZTAPYJPDJZGFG-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000002118 epoxides Chemical group 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000007171 acid catalysis Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XHXUANMFYXWVNG-ADEWGFFLSA-N (-)-Menthyl acetate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RESJVOHCWVTFAF-UHFFFAOYSA-N 2,3-dimethyl-5-octyl-1,4-dioxane Chemical compound CCCCCCCCC1COC(C)C(C)O1 RESJVOHCWVTFAF-UHFFFAOYSA-N 0.000 description 2
- MZJQJNOEIWVZHP-UHFFFAOYSA-N 2-butyl-1,4-dioxane Chemical compound CCCCC1COCCO1 MZJQJNOEIWVZHP-UHFFFAOYSA-N 0.000 description 2
- NEVIBJTYLVDKLM-UHFFFAOYSA-N 2-hexyl-1,4-dioxane Chemical compound CCCCCCC1COCCO1 NEVIBJTYLVDKLM-UHFFFAOYSA-N 0.000 description 2
- HCAWSCPVDPVRAL-UHFFFAOYSA-N 2-methyl-5-octyl-1,4-dioxane Chemical compound CCCCCCCCC1COC(C)CO1 HCAWSCPVDPVRAL-UHFFFAOYSA-N 0.000 description 2
- OPUMBISFQNDYHN-UHFFFAOYSA-N 5-butyl-2,3-dimethyl-1,4-dioxane Chemical compound CCCCC1COC(C)C(C)O1 OPUMBISFQNDYHN-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 150000002012 dioxanes Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (+)-β-citronellol Chemical compound OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- CZCBTSFUTPZVKJ-UWVGGRQHSA-N (2R,4S)-rose oxide Chemical compound C[C@H]1CCO[C@@H](C=C(C)C)C1 CZCBTSFUTPZVKJ-UWVGGRQHSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- 239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 1
- 239000001605 (5-methyl-2-propan-2-ylcyclohexyl) acetate Substances 0.000 description 1
- 239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-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
- 229930004024 (S)-(-)-citronellol Natural products 0.000 description 1
- 235000018285 (S)-(-)-citronellol Nutrition 0.000 description 1
- 150000000180 1,2-diols Chemical class 0.000 description 1
- YQQVFXIBTVUNMC-UHFFFAOYSA-N 2,3-dibutyl-5-hexyl-1,4-dioxane Chemical compound CCCCCCC1COC(CCCC)C(CCCC)O1 YQQVFXIBTVUNMC-UHFFFAOYSA-N 0.000 description 1
- TUMVLPUILFSMBB-UHFFFAOYSA-N 2-butyl-5-ethyl-1,4-dioxane Chemical compound CCCCC1COC(CC)CO1 TUMVLPUILFSMBB-UHFFFAOYSA-N 0.000 description 1
- KWXIRCHYBHARCV-UHFFFAOYSA-N 2-butyl-5-hexyl-1,4-dioxane Chemical compound CCCCCCC1COC(CCCC)CO1 KWXIRCHYBHARCV-UHFFFAOYSA-N 0.000 description 1
- IUIFRVFYPWPOMG-UHFFFAOYSA-N 2-butyl-6-ethyl-1,4-dioxane Chemical compound CCCCC1COCC(CC)O1 IUIFRVFYPWPOMG-UHFFFAOYSA-N 0.000 description 1
- IYAVCNTVGUHYBF-UHFFFAOYSA-N 2-butyl-6-hexyl-1,4-dioxane Chemical compound CCCCCCC1COCC(CCCC)O1 IYAVCNTVGUHYBF-UHFFFAOYSA-N 0.000 description 1
- ZWCODXOSIRERCZ-UHFFFAOYSA-N 2-decyl-1,4-dioxane Chemical compound CCCCCCCCCCC1COCCO1 ZWCODXOSIRERCZ-UHFFFAOYSA-N 0.000 description 1
- ZXISBFCITOXJKG-UHFFFAOYSA-N 2-decyl-5-methyl-1,4-dioxane Chemical compound CCCCCCCCCCC1COC(C)CO1 ZXISBFCITOXJKG-UHFFFAOYSA-N 0.000 description 1
- MYGHMNTYPOBIFO-UHFFFAOYSA-N 2-decyl-6-ethyl-1,4-dioxane Chemical compound CCCCCCCCCCC1COCC(CC)O1 MYGHMNTYPOBIFO-UHFFFAOYSA-N 0.000 description 1
- TYOIQHUEBHPZNO-UHFFFAOYSA-N 2-ethyl-5-octyl-1,4-dioxane Chemical compound CCCCCCCCC1COC(CC)CO1 TYOIQHUEBHPZNO-UHFFFAOYSA-N 0.000 description 1
- NMMJNOWAYLYDCI-UHFFFAOYSA-N 2-ethyl-6-octyl-1,4-dioxane Chemical compound CCCCCCCCC1COCC(CC)O1 NMMJNOWAYLYDCI-UHFFFAOYSA-N 0.000 description 1
- IRTCJFCIQKNFPP-UHFFFAOYSA-N 2-methyl-1,4-dioxane Chemical compound CC1COCCO1 IRTCJFCIQKNFPP-UHFFFAOYSA-N 0.000 description 1
- UBFLMINMRASNFR-UHFFFAOYSA-N 2-methyl-6-octyl-1,4-dioxane Chemical compound CCCCCCCCC1COCC(C)O1 UBFLMINMRASNFR-UHFFFAOYSA-N 0.000 description 1
- NOFHGTFVUKJZTK-UHFFFAOYSA-N 2-octyl-1,4-dioxane Chemical compound CCCCCCCCC1COCCO1 NOFHGTFVUKJZTK-UHFFFAOYSA-N 0.000 description 1
- MVVXHGJTULQNFK-UHFFFAOYSA-N 3-methyl-oxacyclopentadecan-2-one Chemical compound CC1CCCCCCCCCCCCOC1=O MVVXHGJTULQNFK-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
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 1
- YEUBXNCARHFSRE-UHFFFAOYSA-N 5-butyl-2,3-diethyl-1,4-dioxane Chemical compound CCCCC1COC(CC)C(CC)O1 YEUBXNCARHFSRE-UHFFFAOYSA-N 0.000 description 1
- MINIMUZAYBFQJL-UHFFFAOYSA-N 5-hexyl-2,3-dimethyl-1,4-dioxane Chemical compound CCCCCCC1COC(C)C(C)O1 MINIMUZAYBFQJL-UHFFFAOYSA-N 0.000 description 1
- QCJVKUULZGKQDG-UHFFFAOYSA-N 8,8-Dimethoxy-2,6-dimethyl-2-octanol Chemical compound COC(OC)CC(C)CCCC(C)(C)O QCJVKUULZGKQDG-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 240000000467 Carum carvi Species 0.000 description 1
- 235000005747 Carum carvi Nutrition 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- XHXUANMFYXWVNG-UHFFFAOYSA-N D-menthyl acetate Natural products CC(C)C1CCC(C)CC1OC(C)=O XHXUANMFYXWVNG-UHFFFAOYSA-N 0.000 description 1
- 241001071804 Gentianaceae Species 0.000 description 1
- 241000212322 Levisticum officinale Species 0.000 description 1
- 235000015511 Liquidambar orientalis Nutrition 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- UAVFEMBKDRODDE-UHFFFAOYSA-N Vetiveryl acetate Chemical compound CC1CC(OC(C)=O)C=C(C)C2CC(=C(C)C)CC12 UAVFEMBKDRODDE-UHFFFAOYSA-N 0.000 description 1
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- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- 229940011037 anethole Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
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- 235000017803 cinnamon Nutrition 0.000 description 1
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- 238000000354 decomposition reaction Methods 0.000 description 1
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- 239000003599 detergent Substances 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000001186 myroxylon pereirae klotzsch oil Substances 0.000 description 1
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
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- 150000003138 primary alcohols Chemical class 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762629000 DE2629000A1 (de) | 1976-06-28 | 1976-06-28 | Verwendung alkylsubstituierter 1,4-dioxane als riechstoffe, sowie diese enthaltende riechstoffkompositionen |
| NL7706255A NL7706255A (nl) | 1976-06-28 | 1977-06-07 | Werkwijze voor het bereiden van door een of meer alkylgroepen gesubstitueerde 1,4-dioxanen alsmede de toepassing ervan als reukstof. |
| US05/806,616 US4124541A (en) | 1976-06-28 | 1977-06-15 | Dioxa bicyclo dodecane and -hexadecane perfume compositions |
| GB26499/77A GB1539651A (en) | 1976-06-28 | 1977-06-24 | Perfume compositions comprising alkyl substituted 1,4-dioxanes |
| JP7563477A JPS533540A (en) | 1976-06-28 | 1977-06-27 | Scent composed of or containig alkyll substituted 1*44dioxane |
| FR7719867A FR2356414A1 (fr) | 1976-06-28 | 1977-06-28 | Utilisation de 1,4 dioxannes portant des substituants alkyle comme matieres aromatiques et compositions de parfum en contenant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762629000 DE2629000A1 (de) | 1976-06-28 | 1976-06-28 | Verwendung alkylsubstituierter 1,4-dioxane als riechstoffe, sowie diese enthaltende riechstoffkompositionen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2629000A1 true DE2629000A1 (de) | 1978-01-05 |
Family
ID=5981660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762629000 Withdrawn DE2629000A1 (de) | 1976-06-28 | 1976-06-28 | Verwendung alkylsubstituierter 1,4-dioxane als riechstoffe, sowie diese enthaltende riechstoffkompositionen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4124541A (enExample) |
| JP (1) | JPS533540A (enExample) |
| DE (1) | DE2629000A1 (enExample) |
| FR (1) | FR2356414A1 (enExample) |
| GB (1) | GB1539651A (enExample) |
| NL (1) | NL7706255A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2827979A1 (de) * | 1978-06-26 | 1980-01-17 | Henkel Kgaa | 13,15-dioxabicyclo eckige klammer auf 10.5.0 eckige klammer zu heptadecane, deren herstellung und verwendung als riechstoff, sowie diese enthaltende riechstoffkompositionen |
| US4365071A (en) * | 1980-05-20 | 1982-12-21 | The University Of Kentucky Research Foundation | Production of anhydrous 1,4-dioxane |
| JPH0713556B2 (ja) * | 1986-03-31 | 1995-02-15 | 新日本製鐵株式会社 | 高温還元粉排出装置 |
| KR101173707B1 (ko) * | 2004-02-25 | 2012-08-13 | 이데미쓰 고산 가부시키가이샤 | 알킬 아세탈 화합물과 그의 제조방법 및 윤활유 조성물 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2769014A (en) * | 1951-05-17 | 1956-10-30 | Polak & Schwarz S Essencefabri | Process for the preparation of novel perfumes containing an m-dioxane ring |
| US3326746A (en) * | 1962-09-04 | 1967-06-20 | Lever Brothers Ltd | 1, 3-dioxane cleaning compositions |
| CH530460A (de) * | 1970-01-09 | 1972-11-15 | Givaudan & Cie Sa | Riechstoffkompositionen |
| DE2108649C3 (de) * | 1971-02-24 | 1978-12-07 | Basf Ag, 6700 Ludwigshafen | 2-Methyl-2-hepten-6-on-l-al und seine Acetale |
| NL166187C (nl) * | 1973-04-18 | 1981-07-15 | Naarden International Nv | Werkwijze ter bereiding van reukstofcomposities door een 2-gesubstitueerd 4,4,6-trimethyl-1,3-dioxan te mengen met ten minste een andere reukstof en geparfu- meerde voorwerpen. |
| US3952016A (en) * | 1974-03-18 | 1976-04-20 | Lever Brothers Company | 2-Keto-6-substituted dioxane-(1,4) compounds |
| US3966647A (en) * | 1974-03-18 | 1976-06-29 | Lever Brothers Company | Perfume compositions containing monoalkyl-para-dioxanes |
-
1976
- 1976-06-28 DE DE19762629000 patent/DE2629000A1/de not_active Withdrawn
-
1977
- 1977-06-07 NL NL7706255A patent/NL7706255A/xx not_active Application Discontinuation
- 1977-06-15 US US05/806,616 patent/US4124541A/en not_active Expired - Lifetime
- 1977-06-24 GB GB26499/77A patent/GB1539651A/en not_active Expired
- 1977-06-27 JP JP7563477A patent/JPS533540A/ja active Pending
- 1977-06-28 FR FR7719867A patent/FR2356414A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4124541A (en) | 1978-11-07 |
| JPS533540A (en) | 1978-01-13 |
| NL7706255A (nl) | 1977-12-30 |
| FR2356414A1 (fr) | 1978-01-27 |
| FR2356414B1 (enExample) | 1981-07-10 |
| GB1539651A (en) | 1979-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8139 | Disposal/non-payment of the annual fee |