DE2617816A1 - Perfume compsns. contg. epoxynitriles - are prepd. from ketones and chloro-acetonitrile and pref. contg. methyl gps. or alicyclic rings - Google Patents

Perfume compsns. contg. epoxynitriles - are prepd. from ketones and chloro-acetonitrile and pref. contg. methyl gps. or alicyclic rings

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Publication number
DE2617816A1
DE2617816A1 DE19762617816 DE2617816A DE2617816A1 DE 2617816 A1 DE2617816 A1 DE 2617816A1 DE 19762617816 DE19762617816 DE 19762617816 DE 2617816 A DE2617816 A DE 2617816A DE 2617816 A1 DE2617816 A1 DE 2617816A1
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Prior art keywords
epoxy
epoxynitriles
methyl
alkyl
contg
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DE19762617816
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German (de)
Inventor
Klaus Dipl Chem Dr Bruns
Jens Dipl Chem Dr Conrad
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to DE19762617816 priority Critical patent/DE2617816A1/en
Publication of DE2617816A1 publication Critical patent/DE2617816A1/en
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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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals

Abstract

Epoxynitriles used as odoriferous substances in new perfume compsns. have formula R1R2 CH-CN (I) (where R1 is 4-10C alkyl; R2 is 1-5 alkyl; or R1 and R2 together with oxirane ring C-atom can form an opt. alkyl-substd. 5-11C carbocyclic ring system). In pref. (I), R2 is Me and R1 and R2 together with oxirane ring-C are closed to an opt. alkyl-substd. alicyclic 6-11C ring. Perfume compsns. pref. contain 1-50 wt. % (I). Compsns. may be used (i) directly as perfumes, (ii) for perfuming cosmetics, e.g. greams, lotions, soaps, (iii) for improving odour of technical prods., e.g. detergents, disinfectans and textile finishing agents. (I) impart interesting fragrance notes, cling well and are capable of combining to new scents. In an example, a tobacco-based perfume compsn. contained 20 wt. % 2,3-epoxy-3,3-hexamethylene propionitrile.

Description

"Verwendung von Epoxynitrilen als Riechstoffe sowie diese"Use of epoxynitriles as fragrances as well as these

enthaltende Riechstoffkompositionen Es wurde gefunden, daß Epoxynitrile der allgemeinen Formel in der R1 einen Alkylrest mit 4 - 10 Kohlenstoffatomen, R2 einen Alkylrest mit 1 - 5 Kohlenstoffatomen darstellen, weiterhin R1 und R2 mit dem Oxiranringkohlenstoffatom zu einem gegebenenfalls alkylsubstituierten carbocyclischen Ringsystem mit 5 - 11 Ringkohlenstoffatomen geschlossen sein können, in vorteilhafter Weise als Riechstoffe verwendet werden können.containing fragrance compositions It has been found that epoxynitriles of the general formula in which R1 represents an alkyl radical with 4-10 carbon atoms, R2 represents an alkyl radical with 1-5 carbon atoms, furthermore R1 and R2 with the oxirane ring carbon atom can be closed to form an optionally alkyl-substituted carbocyclic ring system with 5-11 ring carbon atoms, are advantageously used as odoriferous substances can.

Die Herstellung der erfindungsgemäß als Riechstoffe zu verwendenden Produkte erfolgt nach an sich bekanntem Verfahren durch Kondensation von Ketonen mit Chloracetonitril in Gegenwart von Basen, wie dies z. B. von A. Jonczyk, M. Fedorynski und M. Makosza in Tetrahedron Letters 23, 2395-96 (1972) beschrieben ist: Eine weitere Herstellungsmöglichkeit besteht in der Epoxidation von α,ß-ungesättigten Nitrilen in Gegenwart von Molybdänkatalysatoren nach einem Verfahren wie es z.B. in der britischen Patentschrift 1 226 937 angegeben ist.The products to be used according to the invention as fragrances are prepared by processes known per se by condensation of ketones with chloroacetonitrile in the presence of bases, as described, for example, in US Pat. B. by A. Jonczyk, M. Fedorynski and M. Makosza in Tetrahedron Letters 23, 2395-96 (1972) is described: Another production possibility consists in the epoxidation of α, ß-unsaturated nitriles in the presence of molybdenum catalysts by a process such as that given in British Patent 1,226,937, for example.

Bei den nach den bekannten Verfahren hergestellten Produkten handelt es sich für den Fall, daß R1 und R2 nicht identisch sind, um cis/trans-Isomerengemische. Eine Trennung der Isomeren ist für deren erfindungsgemäße Verwendung als Riechstoffe nicht erforderlich, sondern es kann das anfallende Isomerengemisch eingesetzt werden.The products manufactured according to the known processes are in the event that R1 and R2 are not identical, they are cis / trans isomer mixtures. A separation of the isomers is necessary for their use according to the invention as fragrances not necessary, but the resulting mixture of isomers can be used.

Als erfindungsgemäß zu verwendende Epoxynitrile sind zum Beispiel 2, 3-Epoxy-3, 5-dimethyl-capronsäurenitril, 2,3-Epoxy-3-methyl-önanthsäurenitril, 2,3-Epoxy-3-methyl-caprylsäurenitril, 2,3-Epoxy-3-methyl-pelargonsäurenitril, 2,3-Epoxy-3-thyl-pelargonsurenitril, 2,3-Epoxy-3-propyl-pelargonsäurenitril, 2, 3-Epoxy-3-isopropyl-pelargonsäurenitril, 2,3-Epoxy-3-butyl-pelargonsäurenitril, 2,3-Epoxy-3-pentyl-pelargonsäurenitril, 2,3-Epoxy-3-methyl-caprinsäurenitril, 2,3-Epoxy-3-methyl-laurinsäurenitril, 2,3-Epoxy-3-(4-methyl-pent-3-enyl)-butyronitril, 1-Oxa-2-cyano-spiro(2,5)-octan, 1-Oxa-2-cyano-6-tert.butyl-spiro(2,5)octan, 2, 3-Epoxy-3 , 3-hexamethylen-propionitril, 2 ,3-Epoxy-3, 3-heptamethylen-propionitril, 2,3-Epoxy-3,3-undecamethylen-propionitril zu nennen.Epoxynitriles to be used according to the invention are, for example 2,3-epoxy-3, 5-dimethyl-caproic acid nitrile, 2,3-epoxy-3-methyl-aenanthic acid nitrile, 2,3-epoxy-3-methyl-caprylic acid nitrile, 2,3-epoxy-3-methyl-pelargonic acid nitrile, 2,3-epoxy-3-thyl-pelargonic acid nitrile, 2,3-epoxy-3-propyl-pelargonitrile, 2,3-epoxy-3-isopropyl-pelargonitrile, 2,3-epoxy-3-butyl-pelargonitrile, 2,3-epoxy-3-pentyl-pelargonitrile, 2,3-epoxy-3-methyl-capric acid nitrile, 2,3-epoxy-3-methyl-laurinonitrile, 2,3-epoxy-3- (4-methyl-pent-3-enyl) -butyronitrile, 1-oxa-2-cyano-spiro (2,5) -octane, 1-oxa-2-cyano-6-tert-butyl-spiro (2,5) octane, 2,3-epoxy-3 , 3-hexamethylene-propionitrile, 2,3-epoxy-3, 3-heptamethylene-propionitrile, 2,3-epoxy-3,3-undecamethylene-propionitrile to call.

Besondere Bedeutung kommt dabei den Produkten zu, bei denen gemäß der allgemeinen Formel R2 einen Methylrest darstellt, beziehungsweise bei denen die Reste R1 und R2 zusammen mit dem Oxiranringkohlenstoffatomen zu einem gegebenenfalls alkylsubstituierten alicyclischen Ringsystem mit 6 - 11 Ringkohlenstoffatomen geschlossen sind.The products for which according to of the general formula R2 represents a methyl radical, or where the radicals R1 and R2 together with the oxirane ring carbon atoms to form an optional alkyl-substituted alicyclic ring system with 6-11 ring carbon atoms closed are.

Die erfindungsgemäß zu verwendenden Epoxynitrile stellen wertvolle Riechstoffe für Duftstoffkompositionen dar. Sie verleihen den Kompsitionen interessante Duftnoten und zeichnen sich durch eine ausgeprägte Haftfestigkeit aus.The epoxynitriles to be used according to the invention are valuable Fragrances for fragrance compositions. They give the compositions interesting Fragrance notes and are characterized by a pronounced adhesive strength.

Als besonderer Vorteil ist dabei die sehr gute Kombinationsfähigkeit zu neuartigen Geruchsnuancen anzusehen.A particular advantage is the very good ability to combine to look at novel odor nuances.

Die erfindungsgemäß zu verwendenden Epoxynitrile stellen in der Mehrzahl neue Verbindungen dar. Die Herstellung erfolgt durch Kondensation von Ketonen mit Chloracetonitril in Gegenwart vcn Basen, wie dies in allgemeiner Form von A. Jonczyk, M. Fedorynski und M. Kaosza in Tetrahedron Letters 23, 2395-96 (1972) beschrieben ist. Angaben über Riechstoffeigenschaften oder gar der Hinweis auf eine Verwendungsmöglichkeit der Epoxynitrile als Riechstoffe finden sich jedoch nicht.The epoxynitriles to be used according to the invention are in the majority new compounds. The production takes place by condensation of ketones with Chloroacetonitrile in the presence of bases, as described in general by A. Jonczyk, M. Fedorynski and M. Kaosza in Tetrahedron Letters 23, 2395-96 (1972) is. Information on odor properties or even the indication of a possible use however, there are no epoxynitriles as fragrances.

Die erfindungsgemäß als Riechstoffe zu verwendenden Epoxynitrile können mit anderen Riechstoffen in den verschiedensten Mengenverhältnissen zu neuen Riechstoffkompositionen gemischt werden. Im allgemeinen wird sich å jedoch der Anteil der Epoxynitrile in den Riechstoffkompositionen in den Mengen von 1 - 50 Gewichtsprozent, bezogen auf die gesamte Komposition, bewegen. Derartige Kompositionen können zwar auch direkt als Parfüm,im allgemeinen aber zur Parfümierung von Kosmetika, wie Cremes, Lotionen, Duftwässern, Aerosolen, Toiletteseifen usw. dienen.The epoxynitriles to be used as fragrances according to the invention can with other fragrances in the most varied of proportions to form new fragrance compositions be mixed. In general, however, the proportion of epoxynitriles in the fragrance compositions in amounts of 1 to 50 percent by weight, based on the entire composition, move. Such compositions can also be used directly as a perfume, but generally for perfuming cosmetics such as creams, lotions, Scented waters, Aerosols, toilet soaps, etc. are used.

Sie können aber auch zur Geruchsverbesserung technischer Produkte wie Wasch- und Reinigungsmittel, Desinfektionsmittel, Textilbehandlungsmittel usw. eingesetzt werden.But they can also be used to improve the smell of technical products such as detergents and cleaning agents, disinfectants, textile treatment agents, etc. can be 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 l e Zunächst werden einige der erfindungsgemäß als Riechstoffe zu verwendenden Epoxynitrile näher beschrieben. EXAMPLES First, some of the invention as Fragrances to be used epoxynitriles described in more detail.

Der Herstellung der Epoxynitrile erfolgte nach folgender allgemeiner Arbeitsvorschrift: Eine Lösung von 0,4 Mol des entsprechenden Ketons und 0,6 Mol Chloracetonitril in 100 ml Ather wurde bei 0°C portionsweise mit 0,6 Mol Kalium-tert.butylat versetzt. Nach Beendigung der stark exothermen Reaktion wurde mehrere Stunden bei Raumtemperatur nachgerührt, mit Ather verdünnt, anschließend mit verdünnter Salzsäure und Sodalösung gewaschen, über Magnesiumsulfat getrocknet, eingedampft und der Rückstand im Vakuum fraktioniert.The production of the epoxynitriles was carried out more generally according to the following Working procedure: A solution of 0.4 mol of the corresponding ketone and 0.6 mol Chloracetonitrile in 100 ml of ether was mixed with 0.6 mol of potassium tert-butoxide in portions at 0 ° C offset. After the strongly exothermic reaction had ended, several hours were at Stirred at room temperature, diluted with ether, then with dilute hydrochloric acid Washed and soda solution, dried over magnesium sulfate, evaporated and the residue fractionated in a vacuum.

Auf diese vorstehend beschriebene Weise wurden folgende Epoxynitrile erhalten: Produkt A 2,3-Epoxy-3,5-dimethyl-capronsäurenitril, (CH3)2-CH-CH2- Farbloses öl vom Sdp. 10 mm 77°C, nD20 = 1,4292 mit einem krautigen Geruch, Verdyl-Note.The following epoxynitriles were obtained in the manner described above: Product A 2,3-epoxy-3,5-dimethyl-caproic acid nitrile, (CH3) 2-CH-CH2- Colorless oil with a bp 10 mm 77 ° C, nD20 = 1.4292 with an herbaceous odor, Verdyl note.

Produkt B 2,3-Epoxy-3-methyl-pelargonsurenitril, 20 Farbloses öl vom Sdp. 0,05 mm 83 C, nD =1,4376 Geruch: Geranonitril-Note. Produkt C 2,3-Epoxy-3-methyl-caprinsäurenitril, Farebloses Öl vom Sdp. 0,01 mm 73°C, nD20 = 1,4407 Geruch: Mandarinen-Note.Product B 2,3-epoxy-3-methyl-pelargonsurenitrile, 20 Colorless oil with a bp. 0.05 mm 83 C, nD = 1.4376 Odor: geranonitrile note. Product C 2,3-epoxy-3-methyl-capric acid nitrile, Colorless oil, bp 0.01 mm 73 ° C, nD20 = 1.4407 Odor: note of mandarin.

Produkt D 2,3-Epoxy-3-methyl-laurinsäurenitril, Farbloses Öl vom Sdp. 9 mm 140°C, nD20 = 1,4447 Geruch: Hundefell-Mandarinen-Note.Product D 2,3-epoxy-3-methyl-laurinonitrile, Colorless oil, bp 9 mm 140 ° C, nD20 = 1.4447 Odor: note of dog fur and tangerine.

Produkt E 2,3-Epoxy-3-(4-methyl-pent-3-enyl)-butyronitril, Farbloses öl vom Sdp. lmm 80 C, nDV = 1,4573 und von eigenartigem metallischem Geruch.Product E 2,3-epoxy-3- (4-methyl-pent-3-enyl) -butyronitrile, Colorless oil of bp lmm 80 C, nDV = 1.4573 and a peculiar metallic odor.

Produkt F 1-Oxa-2-cyano-6-tert.-butyl-spiro[2.5]octan, Farblos, Sdp.0,08 mm 97°C (kristallisiert) von eigenartigem metallischem Geruch.Product F 1-Oxa-2-cyano-6-tert-butyl-spiro [2.5] octane, Colorless, bp 0.08 mm 97 ° C (crystallized) with a peculiar metallic odor.

Produkt G 2,3-Epoxy-3,3-hexamethylen-propionitril Farbloses Öl vom Sdp. 2 mm 870C, nD20 = 1,4762 Geruch: Cumarin-Note Produkt H 2,3-Epoxy-3,3-heptamethylen-propionitril Farbloses Öl vom Sdp. 0,3 mm 780C, nD = 1,4853 von lederartigem Geruch.Product G 2,3-epoxy-3,3-hexamethylene-propionitrile Colorless oil with bp 2 mm 870C, nD20 = 1.4762 Odor: Coumarin note Product H 2,3-epoxy-3,3-heptamethylene-propionitrile Colorless oil with a bp 0.3 mm 780C, nD = 1.4853 with a leathery odor.

Produkt J 2,3-Epoxy-3,3-undecamethylen-propionitril Farbloses Öl vom Sdp. 0,1 mm 1230C, nD20 = 1,4912 von erdigem Geruch.Product J 2,3-epoxy-3,3-undecamethylene-propionitrile Colorless oil with a bp 0.1 mm 1230C, nD20 = 1.4912 with an earthy odor.

Beispiel 1 Tabakbase 2,3-Epoxy-3,3-hexamethylen-propionitril 200 Gew.-Teile Bergamot t öl 200 Lavendelöl 100 Linalool 100 " Geranylacetat 100 Benzoin R 80 " " Terpinyl-iso-butyrat 70 Eichenmoos-Resin 50 Moschus Keton 50 " " Bornylacetat 30 " Patschouliöl 20 " 1000 Gew.-Teile Beispiel 2 Zitronenbase 2,3-Epoxy-3-methyl-laurinsäurenitril 100 Gew.-Teile Bergamottöl kstl. 300 " " Citraldimethylacetal 250 Benzylsalicylat 100 lt lt Linalool 70 Hydroxycitronellaldimethylacetal 50 " " Citronellol 50 Petitgrainöl citronnier 5 lt " " α-Jonon 10 " Methylphenylglyzidat 10%ig 20 " " 1000 Gew.-Teile Beispiel 3 Base für Geschirrspülmittel-Parrümierung 1-Oxa-2-cyano-6-tert.-butyl-spiro [2.5] octan 200 Gew.-Teile Zitronenölterpene 300 Citraldimethylacetal 250 Geraniol synth. 100 " " Neroliöl kstl. 90 Hydroxycitronellaldimethylacetal 50 " Methylj onon 10 1000 Gew.-TeileExample 1 Tobacco base 2,3-epoxy-3,3-hexamethylene-propionitrile 200 parts by weight Bergamot t oil 200 Lavender oil 100 Linalool 100 "Geranyl acetate 100 Benzoin R 80" "Terpinyl isobutyrate 70 oak moss resin 50 musk ketone 50" "Bornyl acetate 30 "patchouli oil 20" 1000 parts by weight Example 2 lemon base 2,3-epoxy-3-methyl-laurinonitrile 100 parts by weight bergamot oil kstl. 300 "" citral dimethyl acetal 250 Benzyl salicylate 100 lt Linalool 70 Hydroxycitronellal dimethyl acetal 50 " "Citronellol 50 petitgrain oil citronnier 5 lt" "α-Ionon 10" methylphenylglycidate 10% strength 20 "" 1000 parts by weight Example 3 Base for dishwashing detergent parrumming 1-Oxa-2-cyano-6-tert-butyl-spiro [2.5] octane 200 parts by weight lemon oil terpenes 300 Citraldimethylacetal 250 Geraniol synth. 100 "" Neroli oil kstl. 90 hydroxycitronellal dimethyl acetal 50 "methyl ionone 10 1000 parts by weight

Claims (14)

Patentansprüche 1. Verwendung von Epoxynitrilen der allgemeinen Formel in der R1 einen Alkylrest mit 4 - 10 Kohlenstoffatomen, R2 einen Alkylrest mit 1 - 5 Kohlenstoffatomen darstellen, weiterhin R1 und R2 mit dem Oxiranringkohlenstoffatom zu einem gegebenenfalls alkylsubstituierten carbocyclischen Ringsystem mit 5 - 11 Ringkohlenstoffatomen geschlossen sein können, als Riechstoffe.Claims 1. Use of epoxynitriles of the general formula in which R1 represents an alkyl radical with 4-10 carbon atoms, R2 represents an alkyl radical with 1-5 carbon atoms, furthermore R1 and R2 with the oxirane ring carbon atom can be closed to form an optionally alkyl-substituted carbocyclic ring system with 5-11 ring carbon atoms, as fragrances. 2. Verwendung von Epoxynitrilen nach Anspruch 1, dadurch gekennzeichnet, daß solche Produkte verwendet werden, bei denen der Rest R2 der allgemeinen Formel einen Methylrest darstellt.2. Use of epoxynitriles according to claim 1, characterized in that that such products are used in which the radical R2 of the general formula represents a methyl radical. 3. Verwendung von Epoxynitrilen nach Anspruch 1, dadurch gekennzeichnet, daß solche Produkte verwendet werden, bei denen die Reste R1 und R2 mit dem Oxiranringkohlenstoffatom zu einem gegebenenfalls alkylsubstituierten alicyclischen Ringsystem mit 6 - lt Ringkohlenstoffatomen geschlossen sind.3. Use of epoxynitriles according to claim 1, characterized in that that such products are used in which the radicals R1 and R2 with the oxirane ring carbon atom to an optionally alkyl-substituted alicyclic ring system with 6 - lt Ring carbon atoms are closed. 4. Riechstoffkompositionen, gekennzeichnet durch einen Gehalt an Epoxynitrilen nach Anspruch 1 - 3.4. Fragrance compositions, characterized by a content of epoxynitriles according to claim 1 - 3. 5. Riechstoffkompositionen nach Anspruch 4, dadurch gekennzeichnet, daß sie die Epoxynitrile in einer Menge von 1 - 50 Gewichtsprozent, bezogen auf die gesamte Komposition, enthalten.5. fragrance compositions according to claim 4, characterized in that that they the epoxynitrile in an amount of 1 - 50 percent by weight, based on the entire composition. 6. 2,3-Epoxy-3,5-dimethyl-capronsäurenitril.6. 2,3-epoxy-3,5-dimethyl-caproic acid nitrile. 7. 2,3-Epoxy-3-methyl-pelargonsäurenitril. 7. 2,3-epoxy-3-methyl-pelargonitrile. 8. 2,3-Epoxy-3-methyl-caprinsäurenitril. 8. 2,3-epoxy-3-methyl-capric acid nitrile. 9. 2,3-Epoxy-3-methyl-laurinsäurenitril.9. 2,3-Epoxy-3-methyl-lauronitrile. 10. 2,3-Epoxy-3-(4-methyl-pent-3-enyl)-butyronitril.10. 2,3-Epoxy-3- (4-methyl-pent-3-enyl) -butyronitrile. 11. 1-Oxa-2-cyano-6-tert.butyl-spiro[2.5]octan.11. 1-Oxa-2-cyano-6-tert-butyl-spiro [2.5] octane. 12. 2,3-Epoxy-3,3-hexamethylen-propionitril.12. 2,3-epoxy-3,3-hexamethylene-propionitrile. 13. 2 ,3-Epoxy-3 , 3-heptamethylen-propionitril.13. 2,3-epoxy-3,3-heptamethylene-propionitrile. 14. 2 ,3-Epoxy-3,3-undecamethylen-propionitril.14. 2,3-epoxy-3,3-undecamethylene-propionitrile.
DE19762617816 1976-04-23 1976-04-23 Perfume compsns. contg. epoxynitriles - are prepd. from ketones and chloro-acetonitrile and pref. contg. methyl gps. or alicyclic rings Withdrawn DE2617816A1 (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004968A2 (en) * 1978-04-17 1979-10-31 Firmenich Sa Norbornene(-ane) derivatives, process for their preparation and their use as perfuming agents
WO2003053903A1 (en) * 2001-12-19 2003-07-03 Flexitral, Inc. Improved citral derivatives
EP1705171A1 (en) * 2001-12-19 2006-09-27 Flexitral, Inc. Improved aromachemicals
WO2004101472A3 (en) * 2003-05-08 2006-11-23 Flexitral Inc Novel fragrance derivatives
US7309795B2 (en) 2001-12-19 2007-12-18 Luca Turin Citral derivatives
US7342042B2 (en) 2001-12-19 2008-03-11 Flexitral, Inc. Lily of the valley aromachemicals

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004968A2 (en) * 1978-04-17 1979-10-31 Firmenich Sa Norbornene(-ane) derivatives, process for their preparation and their use as perfuming agents
EP0004968A3 (en) * 1978-04-17 1979-11-14 Firmenich Sa Norbornene(-ane) derivatives, their use as perfuming agents, perfuming composition containing at least one of these derivatives and process for their preparation
WO2003053903A1 (en) * 2001-12-19 2003-07-03 Flexitral, Inc. Improved citral derivatives
WO2003053902A1 (en) * 2001-12-19 2003-07-03 Flexitral, Inc. Improved aromachemicals
WO2003053901A1 (en) * 2001-12-19 2003-07-03 Flexitral, Inc. Improved citral derivatives
EP1705171A1 (en) * 2001-12-19 2006-09-27 Flexitral, Inc. Improved aromachemicals
US7309795B2 (en) 2001-12-19 2007-12-18 Luca Turin Citral derivatives
US7342042B2 (en) 2001-12-19 2008-03-11 Flexitral, Inc. Lily of the valley aromachemicals
US7704941B2 (en) 2001-12-19 2010-04-27 Flexitral, Inc. Citral derivatives
WO2004101472A3 (en) * 2003-05-08 2006-11-23 Flexitral Inc Novel fragrance derivatives

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