DE2240206C3 - Acetaldehydäthyllinalylacetal, Verfahren zu dessen Herstellung und dessen Verwendung als Riechstoff - Google Patents
Acetaldehydäthyllinalylacetal, Verfahren zu dessen Herstellung und dessen Verwendung als RiechstoffInfo
- Publication number
- DE2240206C3 DE2240206C3 DE2240206A DE2240206A DE2240206C3 DE 2240206 C3 DE2240206 C3 DE 2240206C3 DE 2240206 A DE2240206 A DE 2240206A DE 2240206 A DE2240206 A DE 2240206A DE 2240206 C3 DE2240206 C3 DE 2240206C3
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- acetaldehydäthyllinalylacetal
- fragrance
- production
- 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 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- ZJPKYCLAROITRY-UHFFFAOYSA-N 3-(1-ethoxyethoxy)-3,7-dimethylocta-1,6-diene Chemical compound CCOC(C)OC(C)(C=C)CCC=C(C)C ZJPKYCLAROITRY-UHFFFAOYSA-N 0.000 claims description 7
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 5
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- MMLYERLRGHVBEK-UHFFFAOYSA-N 5,9-dimethyldeca-4,8-dienal Chemical compound CC(C)=CCCC(C)=CCCC=O MMLYERLRGHVBEK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (+)-β-citronellol Chemical compound OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- 229930004024 (S)-(-)-citronellol Natural products 0.000 description 2
- 235000018285 (S)-(-)-citronellol Nutrition 0.000 description 2
- QUMXDOLUJCHOAY-UHFFFAOYSA-N 1-Phenylethyl acetate Chemical compound CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 2
- 240000007436 Cananga odorata Species 0.000 description 2
- 235000007571 Cananga odorata Nutrition 0.000 description 2
- 241000597000 Freesia Species 0.000 description 2
- 239000005792 Geraniol Substances 0.000 description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 2
- SUAUILGSCPYJCS-UHFFFAOYSA-N Musk ambrette Chemical compound COC1=C([N+]([O-])=O)C(C)=C([N+]([O-])=O)C=C1C(C)(C)C SUAUILGSCPYJCS-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 229940007550 benzyl acetate Drugs 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 229940113087 geraniol Drugs 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000001414 (2E)-2-(phenylmethylidene)octanal Substances 0.000 description 1
- 239000001244 (E)-1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one Substances 0.000 description 1
- VPKMGDRERYMTJX-XEHSLEBBSA-N (e)-1-[(1r)-2,6,6-trimethylcyclohex-2-en-1-yl]pent-1-en-3-one Chemical compound CCC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C VPKMGDRERYMTJX-XEHSLEBBSA-N 0.000 description 1
- MKEIDVFLAWJKMY-UHFFFAOYSA-N 1,7-dioxacycloheptadecan-8-one Chemical compound O=C1CCCCCCCCCOCCCCCO1 MKEIDVFLAWJKMY-UHFFFAOYSA-N 0.000 description 1
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 description 1
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 1
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 description 1
- -1 4-tertiary-butylcyclohexyl- Chemical group 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- XGQJZNCFDLXSIJ-UHFFFAOYSA-N Pentadecanal Natural products CCCCCCCCCCCCCCC=O XGQJZNCFDLXSIJ-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- 229940072717 alpha-hexylcinnamaldehyde Drugs 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229940089454 lauryl aldehyde Drugs 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| NL7111071A NL7111071A (OSRAM) | 1971-08-11 | 1971-08-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2240206A1 DE2240206A1 (de) | 1973-02-22 |
| DE2240206B2 DE2240206B2 (de) | 1980-10-16 |
| DE2240206C3 true DE2240206C3 (de) | 1982-01-21 |
Family
ID=19813795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2240206A Expired DE2240206C3 (de) | 1971-08-11 | 1972-08-11 | Acetaldehydäthyllinalylacetal, Verfahren zu dessen Herstellung und dessen Verwendung als Riechstoff |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3948814A (OSRAM) |
| JP (1) | JPS5439450B2 (OSRAM) |
| CH (1) | CH571052A5 (OSRAM) |
| DE (1) | DE2240206C3 (OSRAM) |
| FR (1) | FR2148587B1 (OSRAM) |
| GB (1) | GB1371727A (OSRAM) |
| NL (1) | NL7111071A (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4872285A (OSRAM) * | 1971-12-29 | 1973-09-29 | ||
| US4158096A (en) * | 1978-03-13 | 1979-06-12 | Zoecon Corporation | Intermediates for insect pheromone |
| US4267363A (en) * | 1978-06-26 | 1981-05-12 | Zoecon Corporation | Intermediates for a sex pheramone for yellow scale |
| US4348416A (en) * | 1980-08-07 | 1982-09-07 | International Flavors & Fragrances Inc. | Flavoring with 1-ethoxy-1-ethanol acetate - acetaldehyde mixtures |
| US4296137A (en) * | 1980-08-07 | 1981-10-20 | International Flavors & Fragrances Inc. | Flavoring with 1-ethoxy-1-ethanol acetate |
| US4331571A (en) * | 1980-12-18 | 1982-05-25 | International Flavors & Fragrances Inc. | 1-N-Butoxy-1-ethanol acetate useful for augmenting or enhancing the aroma of perfume materials |
| US4424146A (en) | 1981-10-07 | 1984-01-03 | Fritzsche Dodge & Olcott Inc. | Acetaldehyde ethyl 6-dihydrolinalyl acetal perfume compositions |
| US4383943A (en) * | 1981-10-07 | 1983-05-17 | Fritzsche Dodge & Olcott Inc. | Acetaldehyde ethyl isoeugenyl acetal perfume compositions |
| DE3539467A1 (de) * | 1985-11-07 | 1987-05-14 | Basf Ag | Substituierte 4-methyl-4,7-dihydro-1,3-dioxepine, deren herstellung und verwendung als riechstoffe |
| US5378468A (en) * | 1992-09-22 | 1995-01-03 | The Mennen Company | Composition containing body activated fragrance for contacting the skin and method of use |
| WO2000037117A1 (en) * | 1998-12-22 | 2000-06-29 | Quest International B.V. | Improvements in or relating to reduction of malodour |
| US7763238B2 (en) * | 2002-01-16 | 2010-07-27 | Monell Chemical Senses Center | Olfactory adaptation and cross-adapting agents to reduce the perception of body odors |
-
1971
- 1971-08-11 NL NL7111071A patent/NL7111071A/xx not_active Application Discontinuation
-
1972
- 1972-08-09 CH CH1177872A patent/CH571052A5/xx not_active IP Right Cessation
- 1972-08-09 GB GB3718072A patent/GB1371727A/en not_active Expired
- 1972-08-10 JP JP7955072A patent/JPS5439450B2/ja not_active Expired
- 1972-08-10 US US05/279,297 patent/US3948814A/en not_active Expired - Lifetime
- 1972-08-10 FR FR7228884A patent/FR2148587B1/fr not_active Expired
- 1972-08-11 DE DE2240206A patent/DE2240206C3/de not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2240206A1 (de) | 1973-02-22 |
| NL7111071A (OSRAM) | 1973-02-13 |
| FR2148587B1 (OSRAM) | 1978-11-10 |
| JPS4826940A (OSRAM) | 1973-04-09 |
| FR2148587A1 (OSRAM) | 1973-03-23 |
| US3948814A (en) | 1976-04-06 |
| DE2240206B2 (de) | 1980-10-16 |
| CH571052A5 (OSRAM) | 1975-12-31 |
| JPS5439450B2 (OSRAM) | 1979-11-28 |
| GB1371727A (en) | 1974-10-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) |