EP1078027A1 - Utilization of bicyclic aldehydes as odoriferous agents - Google Patents
Utilization of bicyclic aldehydes as odoriferous agentsInfo
- Publication number
- EP1078027A1 EP1078027A1 EP99920864A EP99920864A EP1078027A1 EP 1078027 A1 EP1078027 A1 EP 1078027A1 EP 99920864 A EP99920864 A EP 99920864A EP 99920864 A EP99920864 A EP 99920864A EP 1078027 A1 EP1078027 A1 EP 1078027A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- bicyclo
- hydroformylation
- methyl
- oct
- aldehydes
- 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
- -1 bicyclic aldehydes Chemical class 0.000 title claims abstract description 11
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 22
- 239000003205 fragrance Substances 0.000 claims description 25
- LHOQCEAXPLQECM-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropentalene-1-carbaldehyde Chemical compound C1CCC2C(C=O)CCC21 LHOQCEAXPLQECM-UHFFFAOYSA-N 0.000 claims description 11
- 239000002537 cosmetic Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 230000001902 propagating effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 239000010948 rhodium Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012459 cleaning agent Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000008447 perception Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KEHFJHPSOFFXBO-SFYZADRCSA-N (3ar,6ar)-1,2,3,3a,4,6a-hexahydropentalene Chemical compound C1C=C[C@@H]2CCC[C@@H]21 KEHFJHPSOFFXBO-SFYZADRCSA-N 0.000 description 1
- ZAOKSGRIAGOZJA-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropentalene-2-carbaldehyde Chemical compound C1CCC2CC(C=O)CC21 ZAOKSGRIAGOZJA-UHFFFAOYSA-N 0.000 description 1
- WGGHTQJCLFQFTA-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydropentalene Chemical compound C1CC=C2CCCC21 WGGHTQJCLFQFTA-UHFFFAOYSA-N 0.000 description 1
- ABIPLJQFLRXYES-UHFFFAOYSA-N 1,2,3,3a-tetrahydropentalene Chemical class C1=CC=C2CCCC21 ABIPLJQFLRXYES-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 210000000416 exudates and transudate Anatomy 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000000606 toothpaste Substances 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C 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
- C11B9/0003—Compounds of unspecified constitution defined by the chemical reaction for their preparation
Definitions
- the invention relates to the use of special bicyclic aldehydes which are obtainable by partial or complete hydroformylation of - optionally (di) methyl-substituted - bicyclo [3.3.0] oct (adienes) as fragrances.
- "Bicyclo [3.3.0] oct (adi) enen” means both bicyclo [3.3.0] octadienes and bicyclo [3.3.0] octene.
- (di) methyl-substituted it is meant that the bicyclic system can carry either one or two methyl groups as substituents.
- 3,985,769 discloses cyciooctanaldehyde (1), which is described as a raw material for the production of acetals derived therefrom with fragrance properties, with regard to its olfactory properties, which are described as "intensely green”. .CHO
- fragrance industry has a constant need for new fragrances with interesting fragrances to complement the range of naturally available fragrances and make the necessary adjustments to changing fashionable tastes as well as the ever-increasing need for odor-improving products for everyday needs such as To be able to cover cosmetics and cleaning agents.
- a fragrance booster is to be understood as a substance that is able to give the olfactory impressions of the components of a multi-substance system, i.e. a mixture of two or more fragrances to intensify sustainably.
- the invention relates to the use of bicyclic aldehydes, which are obtainable by partial or complete hydroformylation of - optionally (di) methyl-substituted - bicyclo [3.3.0] oct (adienes) as fragrances.
- Another object of the invention is the use of bicyclic aldehydes, which are obtainable by partial or complete hydroformylation of - optionally (di) methyl-substituted - bicyclo [3.3.0] oct (adi) enes as fragrance boosters.
- 3-formyl-bicyclo [3.3.0] octane is particularly preferred.
- aldehydes to be used according to the invention are advantageously prepared by hydroformylation of - optionally (di) methyl-substituted - bicyclo [3.3.0] oct (adi) enes.
- the latter compounds have a bicyclic system as a common framework.
- Hydroformylation is a reaction known to the person skilled in the art, which was discovered in 1938 by von Roelen. Alkenes with carbon monoxide and hydrogen are converted into aldehydes. The reaction is also known as oxo synthesis.
- the odor profile of the hydroformylation products according to the invention is original and new.
- perfume compositions they enhance harmony and charisma as well as adhesion, whereby the dosage is adjusted to the desired fragrance, taking into account the other components of the composition.
- Fragrances do not allow any conclusions to be drawn about the properties in the broadest sense of "structurally analogous" compounds - in the present case, for example, cyciooctanaldehyde (1) - or their mixtures with one another, because neither the mechanism of fragrance perception nor the influence of the chemical structure on fragrance perception have been adequately researched So it cannot normally be predicted whether a changed structure or special mixing ratios of known odoriferous substances will lead to a change in the olfactory properties and whether this change should be assessed positively or negatively.
- the hydroformylation products according to the invention are particularly suitable for modifying and enhancing known compositions.
- their extraordinary olfactory strength should be emphasized, which generally contributes to the refinement of compositions.
- hydroformylation products according to the invention round off and harmonize the olfactory notes of a wide range of known compositions, but without dominating in an unpleasant manner.
- (3) 2-Formyl-bicyclo [3.3.0] octane (3) is particularly suitable for use according to the invention as a fragrance and / or fragrance booster. Accordingly, the use of (3) 2-formyl-bicyclo [3.3.0] octane, for example in room fragrances, is particularly advantageous. In addition, it has been shown that (3) can be used with particular advantages in cleaning agents for strengthening citrus scents. CHO
- the usable proportions of the hydroformylation products according to the invention in fragrance compositions range from 0.001 to 70% by weight, based on the mixture as a whole.
- the hydroformylation products according to the invention and compositions of this type can be used both for perfuming cosmetic preparations such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, toothpastes, mouthwashes, deodorants and in exudate perfumery.
- perfuming technical products as well as detergents and cleaning agents, fabric softeners, textile treatment agents or tobacco.
- compositions are metered into them in an olfactory effective amount, in particular in a concentration in the range from 0.05 to 2% by weight, based on the entire product.
- these values are not intended to represent any limit values, since the experienced perfumer can achieve effects with lower concentrations or build new types of complexes with even higher doses.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19817042 | 1998-04-17 | ||
DE19817042A DE19817042A1 (en) | 1998-04-17 | 1998-04-17 | Bicyclic aldehydes obtained by hydroformylation of bicyclo(3.3.0)oct(adi)enes used as perfumes or perfume boosters |
PCT/EP1999/003206 WO1999054429A1 (en) | 1998-04-17 | 1999-04-08 | Utilization of bicyclic aldehydes as odoriferous agents |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1078027A1 true EP1078027A1 (en) | 2001-02-28 |
EP1078027B1 EP1078027B1 (en) | 2004-12-22 |
Family
ID=7864829
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99920864A Expired - Lifetime EP1078027B1 (en) | 1998-04-17 | 1999-04-08 | Utilization of bicyclic aldehydes as odoriferous agents |
Country Status (7)
Country | Link |
---|---|
US (1) | US6537963B1 (en) |
EP (1) | EP1078027B1 (en) |
JP (1) | JP2002512300A (en) |
DE (2) | DE19817042A1 (en) |
ES (1) | ES2233044T3 (en) |
IL (1) | IL139025A (en) |
WO (1) | WO1999054429A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6271193B1 (en) | 2000-10-11 | 2001-08-07 | International Flavors & Fragrances Inc. | Carbon containing functional group substituted 4,5,6,7-tetrahydro-polyalkylated-4-indanes, isomers thereof, processes for preparing same and uses thereof |
FR2981070B1 (en) | 2011-10-11 | 2014-01-10 | V Mane Fils | NOVEL CYCLOALCANIC ALDEHYDES, PROCESS FOR THEIR PREPARATION AND USE IN PERFUMERY |
WO2020053790A1 (en) | 2018-09-11 | 2020-03-19 | Energizer Brands, Llc | Hearing aid battery with slotted grommet |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3985769A (en) * | 1974-11-15 | 1976-10-12 | Universal Oil Products Company | Acetal derivatives of cyclooctyl carboxaldehydes |
DE2849720A1 (en) * | 1978-11-16 | 1980-05-29 | Henkel Kgaa | NEW ALDEHYDE, THEIR PRODUCTION AND THEIR USE AS A FRAGRANCE |
DE2849742B2 (en) * | 1978-11-16 | 1980-10-16 | Henkel Kgaa, 4000 Duesseldorf | Process for the production of aldehydes and use of the process products as fragrances |
US4524017A (en) * | 1981-02-28 | 1985-06-18 | Nippon Petrochemicals Co., Ltd. | Derivatives of norbornanes having hydrocarbon side chains and perfume compositions containing the same |
JPS5821638A (en) * | 1981-07-31 | 1983-02-08 | Mitsubishi Petrochem Co Ltd | Preparation of dialdehydes |
-
1998
- 1998-04-17 DE DE19817042A patent/DE19817042A1/en not_active Withdrawn
-
1999
- 1999-04-08 IL IL13902599A patent/IL139025A/en not_active IP Right Cessation
- 1999-04-08 ES ES99920864T patent/ES2233044T3/en not_active Expired - Lifetime
- 1999-04-08 EP EP99920864A patent/EP1078027B1/en not_active Expired - Lifetime
- 1999-04-08 DE DE59911332T patent/DE59911332D1/en not_active Expired - Fee Related
- 1999-04-08 WO PCT/EP1999/003206 patent/WO1999054429A1/en active IP Right Grant
- 1999-04-08 US US09/673,376 patent/US6537963B1/en not_active Expired - Fee Related
- 1999-04-08 JP JP2000544762A patent/JP2002512300A/en active Pending
Non-Patent Citations (1)
Title |
---|
See references of WO9954429A1 * |
Also Published As
Publication number | Publication date |
---|---|
ES2233044T3 (en) | 2005-06-01 |
IL139025A0 (en) | 2001-11-25 |
WO1999054429A1 (en) | 1999-10-28 |
DE19817042A1 (en) | 1999-10-21 |
DE59911332D1 (en) | 2005-01-27 |
IL139025A (en) | 2004-02-08 |
JP2002512300A (en) | 2002-04-23 |
EP1078027B1 (en) | 2004-12-22 |
US6537963B1 (en) | 2003-03-25 |
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