JP2018501246A - 1−(3,3−ジメチルシクロヘキサ−1−エンイル)エタノンの新規アセタール、その調製法、さらに香料におけるその使用 - Google Patents
1−(3,3−ジメチルシクロヘキサ−1−エンイル)エタノンの新規アセタール、その調製法、さらに香料におけるその使用 Download PDFInfo
- Publication number
- JP2018501246A JP2018501246A JP2017533198A JP2017533198A JP2018501246A JP 2018501246 A JP2018501246 A JP 2018501246A JP 2017533198 A JP2017533198 A JP 2017533198A JP 2017533198 A JP2017533198 A JP 2017533198A JP 2018501246 A JP2018501246 A JP 2018501246A
- Authority
- JP
- Japan
- Prior art keywords
- enyl
- dimethylcyclohex
- compound
- methyl
- composition
- 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
- 239000002304 perfume Substances 0.000 title claims abstract description 13
- JIYZCVGAWRMUDR-UHFFFAOYSA-N 1-(3,3-dimethylcyclohexen-1-yl)ethanone Chemical compound CC(=O)C1=CC(C)(C)CCC1 JIYZCVGAWRMUDR-UHFFFAOYSA-N 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 8
- 150000001241 acetals Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 239000003205 fragrance Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 16
- -1 acetal derivatives of 1- (3,3-dimethylcyclohex-1-enyl) ethanone Chemical class 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 54
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- BCDNXQILXGVEPG-UHFFFAOYSA-N 2-(3,3-dimethylcyclohexen-1-yl)-2,5,5-trimethyl-1,3-dioxane Chemical compound CC1(C=C(CCC1)C1(OCC(CO1)(C)C)C)C BCDNXQILXGVEPG-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- KVHWYEMJFASNQQ-UHFFFAOYSA-N 2-(3,3-dimethylcyclohexen-1-yl)-2-methyl-1,3-dioxolane Chemical compound CC1(C=C(CCC1)C1(OCCO1)C)C KVHWYEMJFASNQQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 230000001953 sensory effect Effects 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- WBJSUNAMJYSYNW-UHFFFAOYSA-N 2-(3,3-dimethylcyclohexen-1-yl)-2,4-dimethyl-1,3-dioxolane Chemical compound CC1(C=C(CCC1)C1(OCC(O1)C)C)C WBJSUNAMJYSYNW-UHFFFAOYSA-N 0.000 claims description 6
- YAJGAUFUUNHRFU-UHFFFAOYSA-N 2-(3,3-dimethylcyclohexen-1-yl)-5,5-diethyl-2-methyl-1,3-dioxane Chemical compound CC1(C=C(CCC1)C1(OCC(CO1)(CC)CC)C)C YAJGAUFUUNHRFU-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000001371 (5E)-3,5-dimethylocta-1,5,7-trien-3-ol Substances 0.000 claims description 5
- RAEMEFHPGFURGW-UHFFFAOYSA-N 2-(3,3-dimethylcyclohexen-1-yl)-2,5-dimethyl-1,3-dioxane Chemical compound CC1(C=C(CCC1)C1(OCC(CO1)C)C)C RAEMEFHPGFURGW-UHFFFAOYSA-N 0.000 claims description 5
- ZJIQIJIQBTVTDY-SREVYHEPSA-N dehydrolinalool Chemical compound CC(=C)\C=C/CC(C)(O)C=C ZJIQIJIQBTVTDY-SREVYHEPSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- XIXZABWGJIRVKG-UHFFFAOYSA-N 2-(3,3-dimethylcyclohexen-1-yl)-2-methyl-1,3-dioxane Chemical compound CC1(C=C(CCC1)C1(OCCCO1)C)C XIXZABWGJIRVKG-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 claims description 3
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 3
- 238000006359 acetalization reaction Methods 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 claims description 3
- 229950006800 prenderol Drugs 0.000 claims description 3
- 235000013772 propylene glycol Nutrition 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 230000000638 stimulation Effects 0.000 claims description 2
- JOWXBGIZDALBJW-UHFFFAOYSA-N 3h-dioxepine Chemical compound C1OOC=CC=C1 JOWXBGIZDALBJW-UHFFFAOYSA-N 0.000 claims 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 11
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract description 7
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 5
- GPVOTKFXWGURGP-UHFFFAOYSA-N 2,5,5-trimethyl-1,3,4,4a,6,7-hexahydronaphthalen-2-ol Chemical compound C1C(C)(O)CCC2C1=CCCC2(C)C GPVOTKFXWGURGP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- DYYRDODJUTUKHB-UHFFFAOYSA-N 2-(3,3-dimethylcyclohexen-1-yl)-2-methyl-4,7-dihydro-1,3-dioxepine Chemical compound CC1(C=C(CCC1)C1(OCC=CCO1)C)C DYYRDODJUTUKHB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000220317 Rosa Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000000873 masking effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 230000004936 stimulating effect Effects 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NZMDEABOJIQLEP-UHFFFAOYSA-N 1-(5,5-dimethylcyclohexen-1-yl)ethanone Chemical compound CC(=O)C1=CCCC(C)(C)C1 NZMDEABOJIQLEP-UHFFFAOYSA-N 0.000 description 2
- DASQRZJTRKBKPP-UHFFFAOYSA-N 5-butan-2-yl-2-(2,4-dimethylcyclohex-3-en-1-yl)-5-methyl-1,3-dioxane Chemical compound O1CC(C(C)CC)(C)COC1C1C(C)C=C(C)CC1 DASQRZJTRKBKPP-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 239000002386 air freshener Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000008786 sensory perception of smell Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- GPVOTKFXWGURGP-YPMHNXCESA-N (2s,4as)-2,5,5-trimethyl-1,3,4,4a,6,7-hexahydronaphthalen-2-ol Chemical class C([C@@](C1)(O)C)C[C@@H]2C1=CCCC2(C)C GPVOTKFXWGURGP-YPMHNXCESA-N 0.000 description 1
- 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 1
- ZITVKGIRQCDOSX-UHFFFAOYSA-N 1h-cyclopropa[a]naphthalene Chemical compound C1=CC=CC2=C3CC3=CC=C21 ZITVKGIRQCDOSX-UHFFFAOYSA-N 0.000 description 1
- LIKDIQKTNWQVSZ-UHFFFAOYSA-N 2-(3,3-dimethylcyclohexyl)-2,4,4-trimethyl-1,3-dioxolane Chemical compound O1C(C)(C)COC1(C)C1CC(C)(C)CCC1 LIKDIQKTNWQVSZ-UHFFFAOYSA-N 0.000 description 1
- KBOYDGAQQSKFIW-UHFFFAOYSA-N 2-(3,3-dimethylcyclohexyl)-2,4-dimethyl-1,3-dioxolane Chemical compound O1C(C)COC1(C)C1CC(C)(C)CCC1 KBOYDGAQQSKFIW-UHFFFAOYSA-N 0.000 description 1
- BWYHTITWPWGSHN-UHFFFAOYSA-N 3,3-dimethylcyclohexene Chemical compound CC1(C)CCCC=C1 BWYHTITWPWGSHN-UHFFFAOYSA-N 0.000 description 1
- AYHBUKCLFLUGTA-UHFFFAOYSA-N 3a-ethyl-6,6,9a-trimethyl-3,4,5,5a,7,8,9,9b-octahydro-1h-benzo[e][2]benzofuran Chemical compound CC12CCCC(C)(C)C1CCC1(CC)C2COC1 AYHBUKCLFLUGTA-UHFFFAOYSA-N 0.000 description 1
- FNWGJNCOWQXTHL-UHFFFAOYSA-N CC1(C=C(CCC1)C1(OCC(CO1)(C)C)C)C.CC1(C=C(CCC1)C1(OCC(CO1)(C)C)C)C Chemical compound CC1(C=C(CCC1)C1(OCC(CO1)(C)C)C)C.CC1(C=C(CCC1)C1(OCC(CO1)(C)C)C)C FNWGJNCOWQXTHL-UHFFFAOYSA-N 0.000 description 1
- XSDNQVMVCDOVQN-UHFFFAOYSA-N CC1(C=C(CCC1)C1(OCC(CO1)(CC)CC)C)C.CC1(C=C(CCC1)C1(OCC(CO1)(CC)CC)C)C Chemical compound CC1(C=C(CCC1)C1(OCC(CO1)(CC)CC)C)C.CC1(C=C(CCC1)C1(OCC(CO1)(CC)CC)C)C XSDNQVMVCDOVQN-UHFFFAOYSA-N 0.000 description 1
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- MWGWENWWMBKKSH-UHFFFAOYSA-N CC1(C=C(CCC1)C1(OCC(O1)C)C)C.CC1(C=C(CCC1)C1(OCC(O1)C)C)C Chemical compound CC1(C=C(CCC1)C1(OCC(O1)C)C)C.CC1(C=C(CCC1)C1(OCC(O1)C)C)C MWGWENWWMBKKSH-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- 229920002774 Maltodextrin Polymers 0.000 description 1
- 244000270834 Myristica fragrans Species 0.000 description 1
- 235000009421 Myristica fragrans Nutrition 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 244000263375 Vanilla tahitensis Species 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
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- 229940097362 cyclodextrins Drugs 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
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- 230000036541 health Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000001702 nutmeg Substances 0.000 description 1
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
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- 239000002453 shampoo Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 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
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon 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
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/04—Seven-membered rings not condensed with other rings
- C07D321/06—1,3-Dioxepines; Hydrogenated 1,3-dioxepines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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Abstract
Description
R1は水素原子または飽和C1〜C2アルキル基を表し、
点線で示される炭素−炭素結合は存在し、または存在せず、
前記結合が存在しない場合、R2は存在しかつ水素原子または飽和C1〜C2アルキル基を表し、
前記結合が存在する場合は、R2は存在せず;
前記化合物は立体異性体、立体異性体の混合物、またはラセミ混合物の形である。
R1は水素原子または飽和C1〜C2アルキル基を表し;
点線で示される炭素−炭素結合は存在し、または存在せず、
前記結合が存在しない場合、R2は存在しかつ水素原子または飽和C1〜C2アルキル基を表し、
前記結合が存在する場合は、R2は存在せず;
前記化合物は立体異性体、立体異性体の混合物、またはラセミ混合物の形である。
a)酸によるデヒドロリナロールの1−(3,3−ジメチルシクロヘキサ−1−エンイル)エタノンへの環化/転位、および;
b)式Iの化合物を得るためのジオールによる1−(3,3−ジメチルシクロヘキサ−1−エンイル)エタノンのアセタール化。
フラスコ中、デヒドロリナロールの同等物をトルエンに入れる。この溶液を還流する。次に、リン酸(デヒドロリナロールの質量の10%)をゆっくりと滴下する。還流下で20時間撹拌した後、周囲温度にいったん戻し、反応媒体を重炭酸ナトリウムの飽和水溶液に注ぐ。相が分離する。有機相を中性になるまで水で洗浄する。溶剤を硫酸マグネシウム上で乾燥させ、濾過し、蒸発させた後、粗生成物を減圧下で蒸留する:その沸点は53.3パスカルで52℃である。
こうして得た2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−1,3−ジオキソランは、以下のスペクトル特性を示す:
1H-NMR (200 MHz, CDCl3): δ (ppm) 0.94 (s, 6H), 1.34-1.37 (m, 2H), 1.41 (s, 3H), 1.57-1.61 (m, 2H), 1.91 (td, J = 6.2 Hz, 1.6 Hz, 2H), 3.70-3.85 (m, 2H), 3.85-3.95 (m, 2H), 5.56 (s, 1H).
13C-NMR (50 MHz, CDCl3): δ(ppm) 19.85, 23.76, 23.96, 29.92, 31.34, 36.95, 64.18, 109.31, 132.60, 134.75.
MS [e/m (%)]: 196 (M+, 0.2), 181 (100), 109 (21), 87 (82), 73 (14), 43 (32).
IR (film, cm-1): 859m, 946w, 1043s, 1110w, 1187m, 1209m, 1371w, 2933m.
2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,4−ジメチル−1,3−ジオキソランを、エチレングリコールの代わりに1,2−プロパンジオールを用いて、実施例1に記載のプロトコルに従い調製する。比率が62:38である、2つのジアステレオマーの形をした2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,4−ジメチル−1,3−ジオキソランで構成された粗生成物を、減圧下で蒸留する:その沸点は66.7パルカスで49℃である。
こうして得られた2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,4−ジメチル−1,3−ジオキソランは、以下のスペクトル特性を示す。
多い方の異性体(62%):
1H-NMR (200 MHz, CDCl3): δ(ppm) 0.93 (s, 6H), 1.25 (d, J = 6.1 Hz, 3H), 1.33-1.38 (m, 2H), 1.42 (s, 3H), 1.59-1.61 (m, 2H), 1.88-1.95 (m, 2H), 3.37-3.42 (m, 1H), 3.86-3.90 (m, 1H), 4.02-4.08 (m, 1H), 5.55 (s, 1H).
13C-NMR (50 MHz, CDCl3): δ(ppm) 18.99, 19.87, 24.00, 24.71, 29.92, 29.96, 31.31, 36.98, 70.58, 71.48, 109.56, 132.28, 135.11.
MS [e/m (%)]: 210 (M+, 0.3), 195 (100), 137 (24), 109 (34), 101 (998), 93 (10), 91 (14), 81 (11), 79 (15), 76 (15), 67 (16), 43 (64), 41 (16).
少ない方の異性体(32%):
1H-NMR (200 MHz, CDCl3): δ(ppm) 0.94 (s, 6H), 1.22 (d, J = 6.1 Hz, 3H), 1.33-1.38 (m, 2H), 1.39 (s, 3H), 1.59-1.61 (m, 2H), 1.88-1.95 (m, 2H), 3.28-3.33 (m, 1H), 4.00-4.04 (m, 1H), 4.18-4.25 (m, 1H), 5.60 (s, 1H).
13C-NMR (50 MHz, CDCl3): δ(ppm) 18.35, 19.83, 24.00, 24.24, 29.80, 29.87, 31.35, 36.98, 70.92, 72.40, 109.50, 132.54, 136.30.
MS [e/m (%)]: 210 (M+, 0.3), 195 (100), 137 (25), 109 (33), 101 (58), 91 (13), 81 (11), 79 (14), 76 (14), 66 (14), 43 (54), 41 (15).
IR (film, cm-1): 866m, 937w, 953w, 1038s, 1085s, 1187s, 1210s, 1370m, 2930m.
2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5−ジメチル−1,3−ジオキサンを、エチレングリコールの代わりに2−メチル−1,3−プロパンジオールを用いて、実施例1に記載のプロトコルに従い調製する。2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5−ジメチル−1,3−ジオキサンで構成された粗生成物を減圧下で蒸留する:その沸点は26.7パスカルで46℃である。
こうして得られた2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5−ジメチル−1,3−ジオキサンは、以下のスペクトル特性を示す:
1H-NMR (200 MHz, CDCl3): δ(ppm) 0.64 (d, J = 6.7 Hz, 3H), 0.85-1.06 (m, 1H), 0.98 (s, 6H), 1.32 (s, 3H), 1.41-1.43 (m, 2H), 1.61-1.65 (m, 2H), 1.84 (t, J = 6.7 Hz, 1H), 1.97-2.07 (m, 1H), 3.26-3.34 (m, 2H), 3.63-3.68 (m, 2H), 5.56 (s, 1H).
13C-NMR (50 MHz, CDCl3): δ(ppm) 12.60, 20.05, 24.52, 28.69, 28.87, 29.91, 31.82, 37.08, 67.41, 100.23, 132.70, 136.17.
MS [e/m (%)]: 224 (M+, 0.2), 209 (54), 137 (22), 121 (10), 115 (100), 109 (22), 93 (14), 91 (13), 79 (15), 77 (12), 67 (11), 55 (26), 43 (41), 41 (14).
IR (film, cm-1): 860m, 1034m, 1052m, 1100m, 1121m, 1162s, 1181s, 1225m, 1368w, 1457w, 2862w, 2930m, 2952m.
2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5,5−トリメチル−1,3−ジオキサンを、エチレングリコールの代わりにネオペンチルグリコールを用いて、実施例1に記載のプロトコルに従い調製する。2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5,5−トリメチル−1,3−ジオキサンで構成された粗生成物を、減圧下で蒸留する:その沸点は26.7パスカルで68℃である。
こうして得られた2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5,5−トリメチル−1,3−ジオキサンは、以下のスペクトル特性を示す。
1H-NMR (200 MHz, CDCl3): δ(ppm) 0.67 (s, 3H), 0.98 (s, 6H), 1.17 (s, 3H), 1.35 (s, 3H), 1.39-1.43 (m, 2H), 1.61-1.65 (m, 2H), 1.85 (t, J = 6.1 Hz, 2H), 3.25-3.28 (m, 2H), 3.42-3.50 (m, 2H), 5.56 (s, 1H).
13C-NMR (50 MHz, CDCl3): δ(ppm) 20.05, 22.15, 22.70, 24.42, 28.07, 29.51, 29.94, 31.79, 37.09, 71.41, 100.29, 132.63, 135.89.
MS [e/m (%)]: 238 (M+, 0.4), 223 (45), 137 (20), 129 (100), 109 (24), 93 (15), 91 (14), 81 (12), 79 (14), 77 (12), 69 (28), 67 (14), 55 (13), 43 (57), 41 (24).
IR (film, cm-1): 859m, 1013m, 1039m, 1083s, 1121m, 1174s, 1207w, 1239w, 1369w, 1470w, 2864w, 2951m.
2−(3,3−ジメチルシクロヘキサ−1−エンイル)−5,5−ジエチル−2−メチル−1,3−ジオキサンを、エチレングリコールの代わりに2,2−ジエチル−1,3−プロパンジオールを用いて、実施例1に記載のプロトコルに従い調製する。2−(3,3−ジメチルシクロヘキサ−1−エンイル)−5,5−ジエチル−2−メチル−1,3−ジオキサンで構成された粗生成物を、減圧下で蒸留する:その沸点は40.0パスカルで78℃である。
こうして得られた2−(3,3−ジメチルシクロヘキサ−1−エンイル)−5,5−ジエチル−2−メチル−1,3−ジオキサンは、以下のスペクトル特性を示す:
1H-NMR (200 MHz, CDCl3): δ(ppm) 0.72 (t, J = 7.5 Hz, 3H), 0.72 (t, J = 7.6 Hz, 3H), 0.98 (s, 6H), 0.98-1.05 (m, 1H), 1.26-1.32 (m, 1H), 1.32 (s, 3H), 1.32-1.42 (m, 2H), 1.58-1.73 (m, 4H), 1.82-1.87 (m, 2H), 3.36-3.45 (m, 4H), 5.56 (s, 1H).
13C-NMR (50 MHz, CDCl3): δ(ppm) 6.61, 7.50, 20.05, 22.58, 24.42, 24.48, 27.97, 29.93, 31.76, 34.22, 37.10, 68.38, 100.47, 132.79, 135.79.
MS [e/m (%)]: 208 (M+, 0,1), 134 (19), 133 (46), 132 (17), 121 (11), 119 (13), 110 (11), 109 (10), 108 (13), 107 (17), 97 (17), 96 (10), 95 (13), 93 (23), 92 (11), 91 (34), 81 (26), 80 (10), 79 (35), 77 (14), 67 (28), 57 (100), 55 (23), 53 (11), 41 (49), 39 (12).
IR (film, cm-1): 838w, 1365m, 1459m, 1726s, 2715w, 2866m, 2928s, 2951s.
2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−4,7−ジヒドロ−1,3−ジオキセピンを、エチレングリコールの代わりにcis−2−ブテン−1,4−ジオールを用いて、実施例1に記載のプロコルに従い調製する。2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−4,7−ジヒドロ−1,3−ジオキセピンで構成された粗生成物を減圧下で蒸留する:その沸点は53.3パスカルで75℃である。
こうして得られた2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−4,7−ジヒドロ−1,3−ジオキセピンは以下のスペクトル特徴を示す:
1H-NMR (200 MHz, CDCl3): δ(ppm) 0.98 (s, 6H), 1.37-1.41 (m, 2H), 1.38 (s, 3H), 1.58-1.66 (m, 2H), 1.91-1.96 (m, 2H), 4.10-4.26 (m, 4H), 5.65 (t, J = 1.1, 2H), 5.76 (s, 1H).
13C-NMR (50 MHz, CDCl3): δ(ppm) 19.98, 22.41, 24.44, 30.06, 31.55, 37.08, 61.49, 103.40, 129.63, 133.88, 134.33.
MS [e/m (%)]: 222 (M+, 0.1), 207 (15), 154 (33), 152 (22), 137 (58), 109 (62), 93 (14), 91 (14), 81 (18), 79 (16), 77 (14), 70 (10), 69 (13), 67 (27), 55 (14), 53 (13), 43 (100), 42 (19), 41 (38), 39 (29).
IR (film, cm-1): 613m, 625m, 640m, 787m, 877m, 949m, 1049s, 1082s, 1117m, 1153s, 1200w, 1231m, 1280m, 1371m, 1451w, 2861w, 2930m.
以下の表に従い作成したローズコード(コードA)に、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5,5−トリメチル−1,3−ジオキサン(実施例4、コードBおよびC)および2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−1,3−ジオキソラン(実施例1、コードD)を加える。
以下の表に従い作成したアップルコード(コードA)に、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5,5−トリメチル−1,3−ジオキサン(実施例4、コードBおよびC)および2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−1,3−ジオキソラン(実施例1、コードD)を加える。
以下の表に従い作成したウッディアコード(コードA)に、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5,5−トリメチル−1,3−ジオキサンを加える(実施例4、コードB)。
Claims (17)
- 以下の一般式Iの化合物であって:
R1は水素原子または飽和C1〜C2アルキル基を表し、
点線で示される炭素−炭素結合は存在し、または存在せず、
前記結合が存在しない場合、R2は存在しかつ水素原子または飽和C1〜C2アルキル基を表し、
前記結合が存在する場合は、R2は存在せず;
前記化合物は立体異性体、立体異性体の混合物、またはラセミ混合物の形である、化合物。 - 点線で示される前記炭素−炭素結合が存在しない、請求項1に記載の化合物。
- nは0で、mは1である、請求項1に記載の化合物。
- nおよびmは0である、請求項1に記載の化合物。
- R1およびR2は、飽和C1〜C2アルキル基を表す、請求項1〜4の何れか一項に記載の化合物。
- 2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−1,3−ジオキソラン、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,4−ジメチル−1,3−ジオキソラン、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−1,3−ジオキサン、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5−ジメチル−1,3−ジオキサン、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5,5−トリメチル−1,3−ジオキサン、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−5,5−ジエチル−2−メチル−1,3−ジオキサン、および2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−4,7−ジヒドロ−1,3−ジオキセピンから選択される、請求項1〜5の何れか一項に記載の化合物。
- 少なくとも1つの以下の一般式Iの化合物を含む組成物であって、
R1は水素原子または飽和C1〜C2アルキル基を表し、
点線で示される炭素−炭素結合は存在し、または存在せず、
前記結合が存在しない場合、R2は存在しかつ水素原子または飽和C1〜C2アルキル基を表し、
前記結合が存在する場合は、R2は存在せず;
前記化合物は立体異性体、立体異性体の混合物、またはラセミ混合物の形である、組成物。 - 2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−1,3−ジオキソラン、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,4−ジメチル−1,3−ジオキソラン、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−1,3−ジオキサン、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5−ジメチル−1,3−ジオキサン、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2,5,5−トリメチル−1,3−ジオキサン、2−(3,3−ジメチルシクロヘキサ−1−エンイル)−5,5−ジエチル−2−メチル−1,3−ジオキサン、および2−(3,3−ジメチルシクロヘキサ−1−エンイル)−2−メチル−4,7−ジヒドロ−1,3−ジオキセピンから選択される少なくとも1つの化合物を含む、請求項7に記載の組成物。
- 前記化合物は芳香剤であり、前記組成物は少なくとも1つの他の芳香剤をさらに含む、請求項7または8に記載の組成物。
- 一般式Iの前記化合物は、前記組成物の総重量の0.01〜99重量%、特に、前記組成物の総重量の0.1〜30重量%の濃度で存在する、請求項7〜9の何れか一項に記載の組成物。
- 前記組成物が、香水組成物である、請求項7〜10の一項に記載の組成物。
- 請求項1〜6の一項に記載の一般式Iの化合物を調製する方法であって、以下のステップ:
a)酸によるデヒドロリナロールの1−(3,3−ジメチルシクロヘキサ−1−エンイル)エタノンへの環化/転位と;
b)一般式Iの前記化合物を得るための、ジオールによる1−(3,3−ジメチルシクロヘキサ−1−エンイル)エタノンのアセタール化とを含む、方法。 - ステップa)の前記酸は、リン酸およびメタンスルホン酸から選択される、請求項12に記載の方法。
- ステップb)の前記ジオールは、エチレングリコール、ネオペンチルグリコール、1,2−プロパンジオール、2,2−ジエチル−1,3−プロパンジオール、2−メチル−1,3−プロパンジオール、1,3−プロパンジオール、またはcis−2−ブテン−1,4−ジオールから選択される、請求項12または13の一項に記載の方法。
- 少なくとも1つの、請求項1〜6の一項に記載の一般式Iの化合物の、芳香剤としての使用。
- 一般式Iの前記化合物は、少なくとも1つの他の芳香剤、および/または、少なくとも1つの溶剤、および/または、少なくとも1つの添加剤と組み合わせて使用される、請求項15に記載の使用。
- 物質、組成物、またはアイテムの感覚刺激特性を付与し、変更し、または強化するための、請求項15または16の一項に記載の使用。
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FR1462834A FR3030520B1 (fr) | 2014-12-18 | 2014-12-18 | Nouveaux acetals de la 1-(3,3-dimethylcyclohex-1-enyl)ethanone, leur procede de preparation ainsi que leur utilisation en parfumerie |
FR1462834 | 2014-12-18 | ||
PCT/FR2015/053495 WO2016097569A1 (fr) | 2014-12-18 | 2015-12-14 | Nouveaux acétals de la 1-(3,3-diméthylcyclohex-1-ènyl) éthanone, leur procédé de préparation ainsi que leur utilisation en parfumerie |
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CL (1) | CL2017001560A1 (ja) |
DK (1) | DK3233820T3 (ja) |
ES (1) | ES2739617T3 (ja) |
FR (1) | FR3030520B1 (ja) |
MX (1) | MX2017006761A (ja) |
PH (1) | PH12017501111A1 (ja) |
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PT (1) | PT3233820T (ja) |
RU (1) | RU2718916C2 (ja) |
SA (1) | SA115370153B1 (ja) |
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EP3763352A1 (en) * | 2019-07-09 | 2021-01-13 | Basf Se | 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde and derivatives and their use as aroma chemicals |
CN116018346A (zh) * | 2020-09-18 | 2023-04-25 | 西姆莱斯有限公司 | Seco-龙涎缩醛 |
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US3144465A (en) | 1961-01-12 | 1964-08-11 | Firmenich & Cie | Internal ketals from dihydro-gammaionone, dihydro-gamma-irone and 5, 5, 9-trimethyl-2-methylene-1-(3'-oxobutyl-1')-decahydronaphthalene |
DE1643710B1 (de) | 1967-12-12 | 1971-06-09 | Basf Ag | Verfahren zur Herstellung von Acetylenmonoalkoholen |
CH586551A5 (ja) * | 1974-01-29 | 1977-04-15 | Firmenich & Cie | |
IT1058547B (it) * | 1976-03-26 | 1982-05-10 | Snam Progetti | Procedimento di ciclizzazione del deidrolinalolo e prodotti ottenuti con tale procedimento |
CH597118A5 (ja) | 1976-07-28 | 1978-03-31 | Firmenich & Cie | |
SU644773A1 (ru) * | 1977-08-01 | 1979-01-30 | Всесоюзный научно-исследовательский институт синтетических и натуральных душистых веществ | Этиленацеталь -толилпропинового альдегида в виде смеси о- и п-изомеров в качестве душистого вещества |
GB8701961D0 (en) | 1987-01-29 | 1987-03-04 | Unilever Plc | Perfumery materials |
US5166412A (en) | 1990-08-28 | 1992-11-24 | Firmenich S.A. | Esters and their use in perfumery |
DE4138732A1 (de) | 1991-11-19 | 1993-05-27 | Dragoco Gerberding Co Gmbh | Cyclische isolongifolanon-ketale, ihre herstellung und ihre verwendung |
SG74666A1 (en) * | 1997-10-21 | 2000-08-22 | Givaudan Roure Int | Beta-ketoester |
EP1056739B1 (en) * | 1998-02-24 | 2003-05-02 | The Procter & Gamble Company | Novel cyclic pro-perfumes having modifiable fragrance raw material alcohol release rate |
DE10022417A1 (de) * | 2000-05-09 | 2001-11-15 | Cognis Deutschland Gmbh | Cyclische Ketale |
US7468447B1 (en) | 2007-11-19 | 2008-12-23 | International Flavors & Fragrances Inc. | Regiospecific Furan Compounds and Their Use in Fragrances |
WO2010122451A1 (en) * | 2009-04-21 | 2010-10-28 | Firmenich Sa | Acetals as perfuming ingredients |
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EP3233820A1 (fr) | 2017-10-25 |
DK3233820T3 (da) | 2019-08-19 |
PH12017501111B1 (en) | 2017-11-27 |
PL3233820T3 (pl) | 2019-10-31 |
JP6663916B2 (ja) | 2020-03-13 |
FR3030520B1 (fr) | 2016-12-23 |
PT3233820T (pt) | 2019-07-24 |
US10723971B2 (en) | 2020-07-28 |
CA2969389C (en) | 2023-02-14 |
CN107406405A (zh) | 2017-11-28 |
EP3233820B1 (fr) | 2019-05-15 |
RU2017120058A3 (ja) | 2019-01-23 |
CN107406405B (zh) | 2021-02-02 |
CA2969389A1 (en) | 2016-06-23 |
PH12017501111A1 (en) | 2017-11-27 |
CL2017001560A1 (es) | 2017-12-29 |
WO2016097569A1 (fr) | 2016-06-23 |
RU2718916C2 (ru) | 2020-04-15 |
RU2017120058A (ru) | 2019-01-23 |
BR112017013160A2 (pt) | 2018-01-02 |
SA115370153B1 (ar) | 2019-12-05 |
MX2017006761A (es) | 2017-09-08 |
KR102574982B1 (ko) | 2023-09-05 |
ES2739617T3 (es) | 2020-02-03 |
US20170342343A1 (en) | 2017-11-30 |
KR20170097713A (ko) | 2017-08-28 |
BR112017013160B1 (pt) | 2021-07-20 |
FR3030520A1 (fr) | 2016-06-24 |
ZA201704635B (en) | 2018-12-19 |
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