DE2558657C2 - - Google Patents
Info
- Publication number
- DE2558657C2 DE2558657C2 DE19752558657 DE2558657A DE2558657C2 DE 2558657 C2 DE2558657 C2 DE 2558657C2 DE 19752558657 DE19752558657 DE 19752558657 DE 2558657 A DE2558657 A DE 2558657A DE 2558657 C2 DE2558657 C2 DE 2558657C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- formula
- compounds
- saturated
- solution
- 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.)
- Expired
Links
- 239000003205 fragrance Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LXHFVSWWDNNDPW-UHFFFAOYSA-N 4-methylheptanoic acid Chemical compound CCCC(C)CCC(O)=O LXHFVSWWDNNDPW-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KZNOWILOENIYSH-UHFFFAOYSA-N 3-methyl lauric acid Chemical compound CCCCCCCCCC(C)CC(O)=O KZNOWILOENIYSH-UHFFFAOYSA-N 0.000 description 2
- YKUOQEJKIPNUEA-UHFFFAOYSA-N 3-methyldodec-2-enoic acid Chemical compound CCCCCCCCCC(C)=CC(O)=O YKUOQEJKIPNUEA-UHFFFAOYSA-N 0.000 description 2
- PWKJMPFEQOHBAC-UHFFFAOYSA-N 4-Ethyloctanoic acid Chemical compound CCCCC(CC)CCC(O)=O PWKJMPFEQOHBAC-UHFFFAOYSA-N 0.000 description 2
- RTSYTZNKRVDRRT-UHFFFAOYSA-N 4-ethyloct-2-enoic acid Chemical compound CCCCC(CC)C=CC(O)=O RTSYTZNKRVDRRT-UHFFFAOYSA-N 0.000 description 2
- 235000019501 Lemon oil Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 244000272264 Saussurea lappa Species 0.000 description 2
- 235000006784 Saussurea lappa Nutrition 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000010501 lemon oil Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 2
- WZZXDQPNKLAUNI-BQYQJAHWSA-N (e)-3-methyldec-4-enoic acid Chemical compound CCCCC\C=C\C(C)CC(O)=O WZZXDQPNKLAUNI-BQYQJAHWSA-N 0.000 description 1
- JUAHIVUUUQRPLE-AATRIKPKSA-N (e)-4-ethylhex-2-enoic acid Chemical compound CCC(CC)\C=C\C(O)=O JUAHIVUUUQRPLE-AATRIKPKSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GSYMWZIKZUHBKV-UHFFFAOYSA-N 1-bromo-2-methylpentane Chemical compound CCCC(C)CBr GSYMWZIKZUHBKV-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- DMUXSGAKEXSNGN-UHFFFAOYSA-N 2-ethyloctanoic acid Chemical compound CCCCCCC(CC)C(O)=O DMUXSGAKEXSNGN-UHFFFAOYSA-N 0.000 description 1
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 1
- ZDIXEQISPGRDEB-UHFFFAOYSA-N 3-Methyl-nonanoic acid Chemical compound CCCCCCC(C)CC(O)=O ZDIXEQISPGRDEB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RKCOKGBXTJRVPG-UHFFFAOYSA-N 3-ethyl-5-methylhept-2-enoic acid Chemical compound CCC(C)CC(CC)=CC(O)=O RKCOKGBXTJRVPG-UHFFFAOYSA-N 0.000 description 1
- FMFKZGSTQPJPHU-UHFFFAOYSA-N 3-ethyl-5-methylheptanoic acid Chemical compound CCC(C)CC(CC)CC(O)=O FMFKZGSTQPJPHU-UHFFFAOYSA-N 0.000 description 1
- UOOWECZOWUNYLA-CMDGGOBGSA-N 3-methyl-2-nonenoic acid Chemical compound CCCCCC\C(C)=C\C(O)=O UOOWECZOWUNYLA-CMDGGOBGSA-N 0.000 description 1
- HHGZJCMMPUJXIF-UHFFFAOYSA-N 4,5-dimethylhexanoic acid Chemical compound CC(C)C(C)CCC(O)=O HHGZJCMMPUJXIF-UHFFFAOYSA-N 0.000 description 1
- ZZKRZEYDDVQQPA-UHFFFAOYSA-N 4-ethyl-5-methylhex-2-enoic acid Chemical compound CCC(C(C)C)C=CC(O)=O ZZKRZEYDDVQQPA-UHFFFAOYSA-N 0.000 description 1
- ZAHVNAWPDWVHOM-UHFFFAOYSA-N 4-ethyl-5-methylhexanoic acid Chemical compound CCC(C(C)C)CCC(O)=O ZAHVNAWPDWVHOM-UHFFFAOYSA-N 0.000 description 1
- KJYXVWHRKCNYKU-UHFFFAOYSA-N 4-ethyl-hexanoic acid Chemical compound CCC(CC)CCC(O)=O KJYXVWHRKCNYKU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001090476 Castoreum Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 238000006680 Reformatsky reaction Methods 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- PEJYPKLIARMXGD-UHFFFAOYSA-N ethyl 2-hydroxy-2-methyldodecanoate Chemical compound CCCCCCCCCCC(C)(O)C(=O)OCC PEJYPKLIARMXGD-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000012437 perfumed product Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7500220A NL7500220A (nl) | 1975-01-08 | 1975-01-08 | Vertakte carbonzuren. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2558657A1 DE2558657A1 (de) | 1976-07-15 |
| DE2558657C2 true DE2558657C2 (US08063081-20111122-C00044.png) | 1987-10-15 |
Family
ID=19822957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752558657 Granted DE2558657A1 (de) | 1975-01-08 | 1975-12-30 | Verzweigtkettige carbonsaeuren als duftstoffe |
Country Status (6)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2757559C2 (de) * | 1977-12-23 | 1986-10-30 | Henkel KGaA, 4000 Düsseldorf | Verwendung der 3,5,5-Trimethylhexansäureester als Riechstoffe sowie diese enthaltende Riechstoffkompositionen |
| DE3278403D1 (en) * | 1981-09-09 | 1988-06-01 | Givaudan & Cie Sa | Perfuming and/or flavouring compositions containing unsaturated acids |
| JPS5859908A (ja) * | 1981-10-06 | 1983-04-09 | Soda Koryo Kk | 不飽和脂肪酸を含有する香料組成物 |
| DE3248463A1 (de) * | 1982-12-29 | 1984-07-12 | Haarmann & Reimer Gmbh, 3450 Holzminden | Alkoxyessigsaeuren, ein verfahren zu ihrer herstellung und ihre verwendung |
| WO2023213386A1 (en) * | 2022-05-04 | 2023-11-09 | Symrise Ag | A fragrance mixture (v) |
-
1975
- 1975-01-08 NL NL7500220A patent/NL7500220A/xx not_active Application Discontinuation
- 1975-12-30 DE DE19752558657 patent/DE2558657A1/de active Granted
-
1976
- 1976-01-07 GB GB48576A patent/GB1503241A/en not_active Expired
- 1976-01-07 JP JP51000967A patent/JPS5191340A/ja active Pending
- 1976-01-07 CH CH12776A patent/CH624844A5/de not_active IP Right Cessation
- 1976-01-07 FR FR7600276A patent/FR2297240A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5191340A (US08063081-20111122-C00044.png) | 1976-08-10 |
| GB1503241A (en) | 1978-03-08 |
| NL7500220A (nl) | 1976-07-12 |
| CH624844A5 (en) | 1981-08-31 |
| DE2558657A1 (de) | 1976-07-15 |
| FR2297240A1 (fr) | 1976-08-06 |
| FR2297240B1 (US08063081-20111122-C00044.png) | 1979-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: A61K 7/46 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |