DE2752972A1 - 2-Acetyl-1,3-dioxan derivs. used as perfume components - e.g. for perfume compsns., cosmetics, detergents, textile treatment agents and tobacco - Google Patents
2-Acetyl-1,3-dioxan derivs. used as perfume components - e.g. for perfume compsns., cosmetics, detergents, textile treatment agents and tobaccoInfo
- Publication number
- DE2752972A1 DE2752972A1 DE19772752972 DE2752972A DE2752972A1 DE 2752972 A1 DE2752972 A1 DE 2752972A1 DE 19772752972 DE19772752972 DE 19772752972 DE 2752972 A DE2752972 A DE 2752972A DE 2752972 A1 DE2752972 A1 DE 2752972A1
- Authority
- DE
- Germany
- Prior art keywords
- acetyl
- perfume
- tobacco
- dioxane
- detergents
- 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- Withdrawn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
- ZNTAGWCDEVPITB-UHFFFAOYSA-N 1-(1,3-dioxan-2-yl)ethanone Chemical compound CC(=O)C1OCCCO1 ZNTAGWCDEVPITB-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 241000208125 Nicotiana Species 0.000 title abstract description 8
- 235000002637 Nicotiana tabacum Nutrition 0.000 title abstract description 8
- 239000002304 perfume Substances 0.000 title abstract description 7
- 239000003795 chemical substances by application Substances 0.000 title abstract description 3
- 239000002537 cosmetic Substances 0.000 title abstract description 3
- 239000003599 detergent Substances 0.000 title abstract description 3
- 239000004753 textile Substances 0.000 title abstract description 3
- 239000003205 fragrance Substances 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims description 12
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 abstract description 2
- -1 2-acetyl-5,5-diethyl-1,3-dioxane Chemical compound 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- ULVSHNOGEVXRDR-UHFFFAOYSA-N 1,1-dimethoxypropan-2-one Chemical compound COC(OC)C(C)=O ULVSHNOGEVXRDR-UHFFFAOYSA-N 0.000 description 2
- MJBLBGCUTIKTJT-UHFFFAOYSA-N 1-(5,5-dimethyl-4-propan-2-yl-1,3-dioxan-2-yl)ethanone Chemical compound CC(C)C1OC(C(C)=O)OCC1(C)C MJBLBGCUTIKTJT-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001414 (2E)-2-(phenylmethylidene)octanal 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
- 150000000185 1,3-diols Chemical class 0.000 description 1
- HEHWDXVAFUFHNP-UHFFFAOYSA-N 1-(5,5-dimethyl-1,3-dioxan-2-yl)ethanone Chemical compound CC(=O)C1OCC(C)(C)CO1 HEHWDXVAFUFHNP-UHFFFAOYSA-N 0.000 description 1
- FACFHHMQICTXFZ-UHFFFAOYSA-N 2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethanamine Chemical compound N1=C2C=CC=CN2C(CCN)=C1C1=CC=CC=C1 FACFHHMQICTXFZ-UHFFFAOYSA-N 0.000 description 1
- MUEWGQPDSSHYTJ-UHFFFAOYSA-N 2-butyl-1,3-dioxane Chemical compound CCCCC1OCCCO1 MUEWGQPDSSHYTJ-UHFFFAOYSA-N 0.000 description 1
- LNEMDIUSUQPKIP-UHFFFAOYSA-N 2-phenyl-1,3-dioxane Chemical compound O1CCCOC1C1=CC=CC=C1 LNEMDIUSUQPKIP-UHFFFAOYSA-N 0.000 description 1
- QDCJIPFNVBDLRH-UHFFFAOYSA-N 5,5-dimethyl-1,3-dioxane Chemical compound CC1(C)COCOC1 QDCJIPFNVBDLRH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 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
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000443 aerosol Substances 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
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- JRUYYVYCSJCVMP-UHFFFAOYSA-N coumarin 30 Chemical compound C1=CC=C2N(C)C(C=3C4=CC=C(C=C4OC(=O)C=3)N(CC)CC)=NC2=C1 JRUYYVYCSJCVMP-UHFFFAOYSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940019836 cyclamen aldehyde Drugs 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229940067137 musk ketone Drugs 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 238000003420 transacetalization reaction Methods 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
"Verwendung von 2-Acetyl-1,3-dioxanen als Riechstoffe sowie"Use of 2-acetyl-1,3-dioxanes as fragrances as well
diese enthaltende Riechstorfkompositioner." Es wurde gefunden, daß 2-Acetyl-1,3-dioxane der allgemeinen Formel in der R1 - R6 Wasserstoff, einen Alkylrest mit 1 - 4 Kohlenstoffatomen oder einen Phenylrest darstellen, wobei nicht mehr als zwei der Reste R1 - R6 in einem Molekül ein Phenylrest ßein können, in vorteilhafter Weise als Riechstoffe der verschiedensten Geruchsnoten verwendet werden können.odoriferous peat compositions containing these. "It has been found that 2-acetyl-1,3-dioxanes of the general formula in which R1 - R6 represent hydrogen, an alkyl radical with 1-4 carbon atoms or a phenyl radical, where no more than two of the radicals R1 - R6 in one molecule can be a phenyl radical, can advantageously be used as fragrances of the most varied odor notes.
Die Herstellung der erfindungsgemäß als Riechstoffe zu verwendenden 2-Acetyl-1,3-dioxane der angegebenen Struktur erfolgt nach üblichen Methoden der organischen Chemie durch Umacetalisierung von 1,1-Dimethoxyaceton mit dem entsprechenden Diol in Gegenwart eines sauren Katalysators gemäß nachstehendem Schema. Als saurer Katalysator kann p-Toluolsulfonsäure, Schwefelsäure, Phosphorsäure oder ein Kationenaustauscher in der Säureform dienen. The 2-acetyl-1,3-dioxanes of the stated structure to be used as fragrances according to the invention are prepared by customary methods of organic chemistry by transacetalization of 1,1-dimethoxyacetone with the corresponding diol in the presence of an acidic catalyst according to the following scheme. The acidic catalyst used can be p-toluenesulfonic acid, sulfuric acid, phosphoric acid or a cation exchanger in the acid form.
Bei der beschriebenen Darstellungsweise treten in einigen Fällen Isomerengemische auf, deren Trennung aber nicht erforderlich ist, vielmehr können derartige Isomerengemische als Riechstoffe bzw. Komponenten von Riechstoffkompositionen Verwendung finden.In the case of the method of representation described, mixtures of isomers occur in some cases on, the separation of which is not necessary, rather such isomer mixtures can find use as fragrances or components of fragrance compositions.
Weitere Möglichkeiten zur Herstellung von Acetalen von α-Ketoaldehyden werden in der amerikanischen Patentschrift 2 751 343 sowie in der deutschen Auslegeschrift 1 254 138 beschrieben, ohne daß hieraus ein Hinweis auf die Riechstoffeigenschaften derartiger Produkte entnommen werden konnte.Further possibilities for the production of acetals from α-ketoaldehydes are in the American patent specification 2,751,343 and in the German Auslegeschrift 1 254 138 without any reference to the properties of the fragrance such products could be taken.
Als erfindungsgemäß zu verwendende 2-Acetyl-1,3-dioxane sind zum Beispiel 2-Acetyl-1,3-dioxan, 2-Acetyl-5,5-dimethyl-1, 3-dioxan, 2-Acetyl-5,5-diäthyl-1,3-dioxan, 2-Acetyl-5-methyl-5-propyl-1 3-dioxan, 2-Acetyl-5-Athyl-5-n-butyl-1,3-dioxan, 2-Acetyl-5-methyl-5-phenyl-1,3-dioxan, 2-Acetyl-4,6-dimethyl-1,3-dioxan, 2-Acetl-4,4,6-trimethyl-1,3-dioxan, 2-Acetyl-4-isopropyl-5,5-dimethyl-1,3-dioxan, 2-Acetyl-4,6-diphenyl-1,3-dioxan zu nennen.2-Acetyl-1,3-dioxanes to be used according to the invention are, for example 2-acetyl-1,3-dioxane, 2-acetyl-5,5-dimethyl-1,3-dioxane, 2-acetyl-5,5-diethyl-1,3-dioxane, 2-acetyl-5-methyl-5-propyl-1 3-dioxane, 2-acetyl-5-ethyl-5-n-butyl-1,3-dioxane, 2-acetyl-5-methyl-5-phenyl-1 , 3-dioxane, 2-acetyl-4,6-dimethyl-1,3-dioxane, 2-acetyl-4,4,6-trimethyl-1,3-dioxane, 2-acetyl-4-isopropyl-5,5-dimethyl-1, 3-dioxane, Mention should be made of 2-acetyl-4,6-diphenyl-1,3-dioxane.
Die erfindungsgemäß zu verwendenden 2-Acetyl-i,3-dioxane sind wertvolle Riechstoffe mit charakteristischen Duftnoten, die von blumig, frisch metallisch bis zur Tabaknote reichen. Ein besonderer Vorteil der errindungsgemaßen Riechstoffe ist ihre sehr gute Kombinationsflhigkeit zu neuartigen Geruchsnuancen.The 2-acetyl-i, 3-dioxanes to be used according to the invention are valuable Fragrances with characteristic scents ranging from floral to fresh metallic up to the tobacco note. A particular advantage of the fragrances according to the invention is their very good ability to combine with novel odor nuances.
Die erfindungsgemäß als Riechstofre zu verwendenden 2-Acetyl-1,3-dioxane können mit anderen Riechstoffen in den verschiedensten Mengenverhältnissen zu neuen Riechstoffkompositionen gemischt werden. Im allgemeinen wird sich der Anteil der 2-Acetyl-1,3-dioxane in den Riechstoffkompositionen in den Mengen von 1 - 50 Gewichtsprozent, bezogen auf die gesamte Komposition, bewegen. Derartige Kompositionen können direkt als ParfUm oder auch zur Parfümierung von Kosmetika wie Cremes, Lotionen, Duftwässern, Aerosolen, Toiletteseifen, technischen Artikeln, wie Wasch- und Reinigungsmitteln, Desinfektionsmitteln, Textilbehandlungsmitteln und Tabak dienen.The 2-acetyl-1,3-dioxanes to be used as fragrances according to the invention can be used with other fragrances in the most varied of proportions to create new ones Fragrance compositions are mixed. In general, the proportion of 2-acetyl-1,3-dioxane in the fragrance compositions in amounts of 1 - 50 percent by weight, in relation to the entire composition, move. Such compositions can be directly as Perfume or for perfuming cosmetics such as creams, lotions, scented waters, Aerosols, toilet soaps, technical articles such as detergents and cleaning agents, Disinfectants, textile treatment agents and tobacco are used.
Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn jedoch hierauf zu beschränken.The following examples are intended to illustrate the subject matter of the invention in greater detail explain without, however, restricting it to this.
B e i s p i e 1 e Die Herstellung der in nachstehender Tabelle aufgeführten 2-Acetyl-1,3-dioxane erfolgte gemäß folgender allgemeiner Arbeitsweise. 1 Mol (118 g) 1,1-Dimethoxyaceton, 1,1 Mol des entsprechenden 1,3-Diols und eine Spatelspitze p-Toluolsulfonsäure wurden zunächst bei ca. 100°C 1/2 Stunde verrührt. Example 1 e The manufacture of the items listed in the table below 2-Acetyl-1,3-dioxane was carried out according to the following general procedure. 1 mole (118 g) 1,1-dimethoxyacetone, 1.1 moles of the corresponding 1,3-diol and a spatula tip p-Toluenesulfonic acid was initially stirred at about 100 ° C. for 1/2 hour.
Anschließend wurde während ca. 3 Stunden das entstandene Methanol langsam abdestilliert. Das erhaltene Rohprodukt wurde mit Sodalösung gewaschen und anschließend fraktioniert destilliert.The methanol formed was then used for about 3 hours slowly distilled off. The obtained crude product was washed with soda solution and then fractionally distilled.
Die erhaltenen Verbindungen wiesen folgende charakteristische NMR-Signale auf: 2,1 - 2,5 ppm Singulett 3 Protonen der Acetylmethylgruppe 6 = 4,4 - 4,75 ppm Singulett 1 Proton in 2-Stellung des Dioxanringes.The compounds obtained had the following characteristic NMR signals on: 2.1 - 2.5 ppm singlet 3 protons of the acetylmethyl group 6 = 4.4 - 4.75 ppm Singlet 1 proton in position 2 of the dioxane ring.
T a b e l l e
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772752972 DE2752972A1 (en) | 1977-11-28 | 1977-11-28 | 2-Acetyl-1,3-dioxan derivs. used as perfume components - e.g. for perfume compsns., cosmetics, detergents, textile treatment agents and tobacco |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772752972 DE2752972A1 (en) | 1977-11-28 | 1977-11-28 | 2-Acetyl-1,3-dioxan derivs. used as perfume components - e.g. for perfume compsns., cosmetics, detergents, textile treatment agents and tobacco |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2752972A1 true DE2752972A1 (en) | 1979-05-31 |
Family
ID=6024783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772752972 Withdrawn DE2752972A1 (en) | 1977-11-28 | 1977-11-28 | 2-Acetyl-1,3-dioxan derivs. used as perfume components - e.g. for perfume compsns., cosmetics, detergents, textile treatment agents and tobacco |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2752972A1 (en) |
-
1977
- 1977-11-28 DE DE19772752972 patent/DE2752972A1/en not_active Withdrawn
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