DE2350178C2 - Cycloaliphatische Ketone, deren Herstellung und Riech- und/oder Geschmacksstoffkomposition auf deren Basis - Google Patents
Cycloaliphatische Ketone, deren Herstellung und Riech- und/oder Geschmacksstoffkomposition auf deren BasisInfo
- Publication number
- DE2350178C2 DE2350178C2 DE2350178A DE2350178A DE2350178C2 DE 2350178 C2 DE2350178 C2 DE 2350178C2 DE 2350178 A DE2350178 A DE 2350178A DE 2350178 A DE2350178 A DE 2350178A DE 2350178 C2 DE2350178 C2 DE 2350178C2
- Authority
- DE
- Germany
- Prior art keywords
- trimethyl
- cyclohexen
- butanone
- general formula
- fragrance
- 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
- 239000000203 mixture Substances 0.000 title description 14
- 239000000796 flavoring agent Substances 0.000 title description 5
- 235000019634 flavors Nutrition 0.000 title description 5
- 239000003205 fragrance Substances 0.000 title description 5
- 150000002576 ketones Chemical class 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 6
- 244000018633 Prunus armeniaca Species 0.000 description 5
- 235000009827 Prunus armeniaca Nutrition 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 235000009508 confectionery Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 244000235659 Rubus idaeus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 235000021013 raspberries Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- IKDIJXDZEYHZSD-UHFFFAOYSA-N 2-phenylethyl formate Chemical compound O=COCCC1=CC=CC=C1 IKDIJXDZEYHZSD-UHFFFAOYSA-N 0.000 description 2
- 239000004641 Diallyl-phthalate Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 206010013911 Dysgeusia Diseases 0.000 description 2
- 241001632576 Hyacinthus Species 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- -1 heterocyclic amine Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 235000013995 raspberry juice Nutrition 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 239000001278 2-(5-ethenyl-5-methyloxolan-2-yl)propan-2-ol Substances 0.000 description 1
- MJQVZIANGRDJBT-VAWYXSNFSA-N 2-Phenylethyl 3-phenyl-2-propenoate Chemical compound C=1C=CC=CC=1/C=C/C(=O)OCCC1=CC=CC=C1 MJQVZIANGRDJBT-VAWYXSNFSA-N 0.000 description 1
- UFOUDYPOSJJEDJ-UHFFFAOYSA-N 2-Phenylpropionaldehyde dimethyl acetal Chemical compound COC(OC)C(C)C1=CC=CC=C1 UFOUDYPOSJJEDJ-UHFFFAOYSA-N 0.000 description 1
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
- IKOVXTPCICEGQK-UHFFFAOYSA-N 3-sulfanyl-1-(2,6,6-trimethylcyclohexen-1-yl)butan-1-one Chemical compound CC(S)CC(=O)C1=C(C)CCCC1(C)C IKOVXTPCICEGQK-UHFFFAOYSA-N 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- MGYMHQJELJYRQS-UHFFFAOYSA-N Ascaridole Chemical compound C1CC2(C)OOC1(C(C)C)C=C2 MGYMHQJELJYRQS-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- 241001090476 Castoreum Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- 244000004281 Eucalyptus maculata Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- BRHDDEIRQPDPMG-UHFFFAOYSA-N Linalyl oxide Chemical compound CC(C)(O)C1CCC(C)(C=C)O1 BRHDDEIRQPDPMG-UHFFFAOYSA-N 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropyl alcohol Natural products CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 240000004760 Pimpinella anisum Species 0.000 description 1
- 235000012550 Pimpinella anisum Nutrition 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- MGYMHQJELJYRQS-ZJUUUORDSA-N ascaridole Natural products C1C[C@]2(C)OO[C@@]1(C(C)C)C=C2 MGYMHQJELJYRQS-ZJUUUORDSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940115397 bornyl acetate Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940005667 ethyl salicylate Drugs 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000008369 fruit flavor Substances 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JDQVBGQWADMTAM-UHFFFAOYSA-N phenethyl isobutyrate Chemical compound CC(C)C(=O)OCCC1=CC=CC=C1 JDQVBGQWADMTAM-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 235000013997 pineapple juice Nutrition 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Natural products C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/204—Aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Seasonings (AREA)
- Dairy Products (AREA)
- Confectionery (AREA)
- Detergent Compositions (AREA)
- Meat, Egg Or Seafood Products (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1518972A CH571484A5 (OSRAM) | 1972-10-17 | 1972-10-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2350178A1 DE2350178A1 (de) | 1974-04-25 |
| DE2350178C2 true DE2350178C2 (de) | 1982-09-23 |
Family
ID=4407093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2350178A Expired DE2350178C2 (de) | 1972-10-17 | 1973-10-05 | Cycloaliphatische Ketone, deren Herstellung und Riech- und/oder Geschmacksstoffkomposition auf deren Basis |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3900520A (OSRAM) |
| JP (2) | JPS5821619B2 (OSRAM) |
| BE (1) | BE806183A (OSRAM) |
| BR (1) | BR7307750D0 (OSRAM) |
| CH (1) | CH571484A5 (OSRAM) |
| DE (1) | DE2350178C2 (OSRAM) |
| ES (1) | ES419672A1 (OSRAM) |
| FR (1) | FR2202885B1 (OSRAM) |
| GB (1) | GB1382000A (OSRAM) |
| NL (1) | NL7313529A (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107209A (en) * | 1977-03-03 | 1978-08-15 | International Flavors & Fragrances Inc. | 1-[3-(Methylthio)butyryl]-2,6,6-trimethyl-cyclohexene and the 1,3-cyclohexadiene analog |
| US4292447A (en) * | 1978-12-15 | 1981-09-29 | International Flavors & Fragrances Inc. | Process for hydrogenation of 2,6,6-trimethyl cyclohexene derivatives, products produced thereby and organoleptic uses of said products |
| US4360032A (en) * | 1978-12-15 | 1982-11-23 | International Flavors & Fragrances Inc. | Use of hydrogenated derivatives of 2,6,6-trimethyl-cyclohexene derivatives in augmenting or enhancing the aroma or taste of smoking tobacco and smoking tobacco articles |
| DE3007232A1 (de) * | 1980-02-27 | 1981-09-10 | Henkel KGaA, 4000 Düsseldorf | Verwendung von 2-phenyl-2(2)-propen-1-yl-carbonsaeureestern als riechstoffe, deren herstellung sowie diese enthaltende riechstoffkompositionen |
| JPS60184907U (ja) * | 1984-05-19 | 1985-12-07 | 林 恭隆 | 内外装用石材 |
| JPH01102326U (OSRAM) * | 1987-12-26 | 1989-07-11 | ||
| JPH0352144U (OSRAM) * | 1989-09-27 | 1991-05-21 | ||
| JPH0466250U (OSRAM) * | 1990-10-19 | 1992-06-10 | ||
| PL209377B1 (pl) * | 2001-12-13 | 2011-08-31 | Firmenich & Cie | Kompozycja zapachowa lub wyrób perfumowany, sposób poprawiania, zwiększania lub modyfikowania zapachu kompozycji zapachowej lub wyrobu perfumowanego, sposób perfumowania powierzchni, sposób intensyfikowania lub przedłużania efektu dyfundowania składnika zapachowego na powierzchni, oraz związek stanowiący składnik czynny |
| EP1622576B1 (en) | 2003-05-07 | 2007-04-25 | Firmenich Sa | Sprayable perfume with an improved tenacity |
| WO2004105713A1 (en) * | 2003-06-02 | 2004-12-09 | Firmenich Sa | Compounds for a controlled release of active molecules |
| US7695097B2 (en) * | 2005-10-11 | 2010-04-13 | Silverbrook Research Pty Ltd | Printhead maintenance station having roller pad |
| BR112017017430B1 (pt) * | 2015-02-25 | 2022-07-05 | Firmenich S.A. | Composição aromatizante sinergética |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2586306A (en) * | 1949-10-26 | 1952-02-19 | Gen Aniline & Film Corp | Synthesis of vitamin a and intermediates therefor |
-
1972
- 1972-10-17 CH CH1518972A patent/CH571484A5/xx not_active IP Right Cessation
-
1973
- 1973-10-02 NL NL7313529A patent/NL7313529A/xx not_active Application Discontinuation
- 1973-10-05 DE DE2350178A patent/DE2350178C2/de not_active Expired
- 1973-10-05 BR BR7750/73A patent/BR7307750D0/pt unknown
- 1973-10-09 US US404582A patent/US3900520A/en not_active Expired - Lifetime
- 1973-10-15 FR FR7336692A patent/FR2202885B1/fr not_active Expired
- 1973-10-16 ES ES419672A patent/ES419672A1/es not_active Expired
- 1973-10-16 JP JP48115417A patent/JPS5821619B2/ja not_active Expired
- 1973-10-17 BE BE136778A patent/BE806183A/xx unknown
- 1973-10-17 GB GB4838573A patent/GB1382000A/en not_active Expired
-
1981
- 1981-12-24 JP JP56215959A patent/JPS5818056B2/ja not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| US3900520A (en) | 1975-08-19 |
| DE2350178A1 (de) | 1974-04-25 |
| BE806183A (fr) | 1974-04-17 |
| FR2202885A1 (OSRAM) | 1974-05-10 |
| JPS57144959A (en) | 1982-09-07 |
| BR7307750D0 (pt) | 1974-08-29 |
| FR2202885B1 (OSRAM) | 1976-10-01 |
| CH571484A5 (OSRAM) | 1976-01-15 |
| JPS5821619B2 (ja) | 1983-05-02 |
| ES419672A1 (es) | 1976-03-16 |
| JPS4975557A (OSRAM) | 1974-07-20 |
| GB1382000A (en) | 1975-01-29 |
| NL7313529A (OSRAM) | 1974-04-19 |
| JPS5818056B2 (ja) | 1983-04-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH524581A (de) | Verfahren zur Herstellung eines mercapto-substituierten Terpenoids | |
| DE2350178A1 (de) | Neue cycloaliphatische ketone | |
| DE1807568B2 (de) | Cycloaliphatische ungesättigte Ketone, Verfahren zu deren Herstellung und deren Verwendung als Riech- und Geschmacksstoffe | |
| DE2405568B2 (de) | Cycloaliphatische verbindungen und deren verwendung als riech- und geschmacksstoffe | |
| DE2440025C3 (de) | S-Acetyl^.e-dimethylen-lOJO-dimethylbicyclo [7.2.O1·9!-undecan und l-Acetyl-ll-methylen- 4,7,7,trimethylcycloundeca^^-dien, Verfahren zu deren Herstellung und ihre Verwendung als Riech- und Geschmacksstoffe | |
| DE2839814A1 (de) | Bicyclische ketonderivate, deren herstellung und verwendung | |
| DE2120413C3 (de) | Trans-2,4,4-trimethyl-1-crotonoylcyclohex-2-en-Verbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Riech- bzw. Aromastoffe | |
| DE2840823C2 (de) | Trans, trans- δ -Damascon, dessen Gemische mit mehr als 50% trans, trans- δ -Damascon und cis, trans- δ -Damascon sowie deren Verwendung als Würzstoffe | |
| DE2159924C3 (de) | Jonon- und Ironderivate, Verfahren zu ihrer Herstellung und Riech- und/oder Geschmackstoffkompositionen | |
| DE2951508A1 (de) | Ungesaettigte alicyclische aether und ihre verwendung als parfuem- und aromabestandteile | |
| DE2721002C3 (de) | Cyclopentanonderivate und diese enthaltende Riechstoff- und Geschmacksstoffkompositionen | |
| DE2244680C2 (de) | Cycloaliphatische Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als geschmacks- oder geruchsmodifizierende Zusätze | |
| DE2504618C3 (de) | Spiranderivate, Verfahren zu deren Herstellung, und die Verwendung dieser Verbindungen als Riech- bzw Aromastoffe | |
| DE2508060A1 (de) | Cycloaliphatische ungesaettigte ketone als geschmack- und riechstoffe | |
| DE2452083A1 (de) | Heterocyclische verbindung, verfahren zu deren herstellung, und diese enthaltende riechstoff- oder aroma-zusammensetzungen | |
| EP0513627A1 (de) | Tetrahydro-alpha-pyronderivat, Verfahren zu seiner Herstellung und dieses enthaltende Riech- und/oder Geschmackstoffkompositionen | |
| DE2750206A1 (de) | Norbornan-derivate, verfahren zu deren herstellung und deren verwendung als organoleptische stoffe | |
| CH577276A5 (en) | Cyclohexenyl- or cyclohexadienyl-mercaptobutanones - used as aroma and/or taste agents in foodstuffs drinks, perfumes, cosmetics,soaps, etc | |
| DE2163521A1 (OSRAM) | ||
| DE2152015C3 (de) | Mercapto-p-menthanderivate, deren Herstellung und Verwendung | |
| US3979422A (en) | Cycloaliphatic ketones, process for making same and odorant and flavoring compositions containing same | |
| CH628217A5 (en) | Process for altering organoleptic properties of products | |
| CH619140A5 (en) | Perfume or flavouring. | |
| DE2934881C1 (de) | Aliphatische polyungesaettigte Ester und ihre Verwendung als Parfuemierungs- und Aromabestandteil | |
| DE2330516A1 (de) | 3,4,7-trimethyl-2-oxo-1,6-dioxa-spiro eckige klammer auf 4,5 eckige klammer zu dec-3-ene, verfahren zu deren herstellung und deren verwendung als riech- und aromabzw. geschmacksstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |