DE3214658A1 - Perfume compositions containing p-tert.-butoxy- and/or p-tert.-amyloxybenzaldehyde - Google Patents

Perfume compositions containing p-tert.-butoxy- and/or p-tert.-amyloxybenzaldehyde

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Publication number
DE3214658A1
DE3214658A1 DE19823214658 DE3214658A DE3214658A1 DE 3214658 A1 DE3214658 A1 DE 3214658A1 DE 19823214658 DE19823214658 DE 19823214658 DE 3214658 A DE3214658 A DE 3214658A DE 3214658 A1 DE3214658 A1 DE 3214658A1
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DE
Germany
Prior art keywords
tert
methyl
butoxy
amyloxybenzaldehyde
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.)
Withdrawn
Application number
DE19823214658
Other languages
German (de)
Inventor
Dieter Dr. 6701 Dannstadt-Schauernheim Degner
Werner Dipl.-Chem. Dr. 6701 Neuhofen Hoffmann
Klaas 6700 Ludwigshafen Jansen
Frank Dipl.-Chem. Dr. 6940 Weinheim Thoemel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DE19823214658 priority Critical patent/DE3214658A1/en
Publication of DE3214658A1 publication Critical patent/DE3214658A1/en
Withdrawn legal-status Critical Current

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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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)

Abstract

Perfume compositions containing p-tert.-butoxy- and/or p-tert.-amyloxybenzaldehyde as perfume component besides other odoriferous substances, as well as the use of these compounds in place of alpha -methyl-p-tert.-butyl- or alpha -methyl-p-isopropyldihydrocinnamaldehyde. The said p-tert.-alkoxybenzaldehydes are scents with the desired sweet-flowery notes which have recently become very advantageously available industrially by electrochemical oxidation of p-tert.-alkoxytoluene in the presence of an alcohol and subsequent acetal cleavage.

Description

Riechstoffkompositionen,enthaltend p-tert .-butoxy-Fragrance compositions containing p-tert-butoxy-

und/oder p-tert.-Amyloxybenzaldehyd Die Erfindung betrifft Riechstoffkompositionen, enthaltend p-tert.-Butoxy- und/oder p-tert.-Amyloxy-benzaldehyd als Riechstoffkomponente neben anderen geruchsaktiven Stoffen sowie die Verwendung dieser Verbindungen anstelle von oC-Methyl-p- tert . -butyl- bzw. Cc-Methyl-p-isopropyl-dihydrozimtaldehyd.and / or p-tert-amyloxybenzaldehyde The invention relates to fragrance compositions, containing p-tert-butoxy- and / or p-tert-amyloxy-benzaldehyde as a fragrance component in addition to other odor-active substances as well as the use of these compounds instead of oC-methyl-p- tert. -butyl- or Cc-methyl-p-isopropyl-dihydrocinnamaldehyde.

In der Parfümerie sind sGR-blumige Riechstoffe außerordentlich geschätzt, insbesondere solche mit Duftnoten in Fich tung Maiglöckchen. Zu dieser Gruppe von Riechstoffen, die für die moderne Parfümerie unentbehrlich geworden ist> geo hören beispielsweise 3,7-Dimethyl-7-hydroxy-octan-1-al (Hydroxycitronellal), 4(4-Methyl-4-hydroxyamyl)-3-cyclohexan-carbonaldehyd, Oc-Methyl-p-isopropyl-dihydrozimtaldehyd (CyclamalR) und α-Methyl-p-tert.-butyl-dihydrozimtaldehyd (LilialR). Diese Riechstoffe finden besonders bei der Bereitung blumiger Duftkompositionen aller Art Verwendung.In the perfumery, sGR floral fragrances are extremely valued, especially those with scent notes in Fich tion lily of the valley. To this group of Fragrances that have become indispensable for modern perfumery> geo hear, for example, 3,7-dimethyl-7-hydroxy-octan-1-al (hydroxycitronellal), 4 (4-methyl-4-hydroxyamyl) -3-cyclohexane-carbonaldehyde, Oc-methyl-p-isopropyl-dihydrocinnamaldehyde (Cyclamal®) and α-methyl-p-tert.-butyl-dihydrocinnamaldehyde (LilialR). These fragrances are found particularly in the preparation of flowery fragrance compositions all kinds of use.

So findet man sie sowohl in blumigen Phantasiekompositionen zur Seifen- oder Waschmittelparfümierung als auch in teuren Extrait-Parfüms z.B. vom Chanel Nr. 5=Typ. Mit ihnen lassen sich die Duftnoten Maiglöckchen, Lilie oder Magnolie unterstreichen oder aber Chyprenoten, orientalische Noten, Holz-und Moschuskomplexe verbessern.You can find them both in flowery fantasy compositions for soap or detergent perfuming as well as in expensive Extrait perfumes e.g. from Chanel No. 5 = type. With them, the scent notes of lily of the valley, lily or magnolia can be added underline or chyprenotes, oriental notes, wood and musk complexes to enhance.

Es wurde nun überraschenderveise gefunden, daß die neuerdings technisch sehr vorteilhaft zugänglichen tert.-Alkoxy--benzaldehyde der Formel I ausgezeichnete neue Vertreter vom Typ der angeführten blumigen, maiglöckchenartigen Riechstoffe sind. Sie entfalten ihre volle Wirkung vorteilhaft zusammen mit anderen Riechstoffen in Riechstoffkompositionen.It has now surprisingly been found that the recently technical very advantageously accessible tert-alkoxy - benzaldehydes of the formula I excellent new representatives of the type of floral, lily of the valley-like fragrances mentioned are. They unfold their full effect advantageously together with other fragrances in fragrance compositions.

Gegenstand der Erfindung sind dementsprechend Riechstoffkompositionen enthaltend 0,1 bis 10, vorzugsweise 1 bis 6 Gew.-% eines tert.-Alkoxy-benzaldehyds der allgemeinen Formel I in der R -H oder -CH3 bedeutet, als Riechstoffkomponente neben anderen geruchsaktiven Stoffen sowie die Verwendung von tert.-Alkoxy-benzaldehyden der Formel I anstelle von -αMethyl-p-tert.-butyl-dihydrozimtaldehyd oder α-Methyl--p-isopropyl-dihydrozimtaldehyd in Riechstpffkompositionen.The invention accordingly relates to fragrance compositions containing 0.1 to 10, preferably 1 to 6% by weight of a tert-alkoxy-benzaldehyde of the general formula I in which R denotes -H or -CH3, as a fragrance component in addition to other odor-active substances and the use of tert-alkoxy-benzaldehydes of the formula I instead of -α-methyl-p-tert-butyl-dihydrocinnamaldehyde or α-methyl-p- isopropyl-dihydrocinnamaldehyde in fragrance compositions.

Die beiden erfindungsgemäß in Riechstoffkompositionen anzuwendenden Verbindungen der Formel I weisen als ainzelriechstoffe eine ausgeprägte Duftnote von der Art des s-Methyl--p-tert.-butyl-dihydrozimtaldehyds (II) und des «sMethyl--p-isopropyl-dihydrozimtaldehyds (III) auf. Der tert.-Butoxybenzaldehyd hat in Parfamkompo:3itionen eine sehr viel stärkere Ausstrahlung als die genannten Handelsprodukte. Untersuchungen haben gezeigt, daß im Vergleich zu II die Geruchsstärke des p-tert.-Butoxybenzaldehyds das Dreifache bis Vierfache beträgt. Der p-tert.-Amyloxybenzaldehyd riecht etwas schwächer als der p-tert.-Butoxybenzaldehyd und weist eine etwas süßlichere Duftnote auf.The two to be used according to the invention in fragrance compositions Compounds of the formula I have a pronounced fragrance note as individual fragrances of the type of s-methyl-p-tert-butyl-dihydrocinnamaldehyde (II) and of the s-methyl-p-isopropyl-dihydrocinnamaldehyde (III) on. The tert-butoxybenzaldehyde has a very large number in Parfamkompo: 3ionen stronger charisma than the mentioned commercial products. Research has shown that compared to II the odor strength of p-tert-butoxybenzaldehyde is three times as high up to four times. The p-tert-amyloxybenzaldehyde smells a little weaker than p-tert-butoxybenzaldehyde and has a slightly sweeter fragrance.

Besonders vorteilhaft kommt ihr Duft in Kombination mit anderen Duftstoffen zur Geltung. So werden die Verbindungen I zusammen mit anderen Riechstoffen in verschiedensten Mengenverhältnissen zu neuen Riechstoffkompositionen vermischt. Ihr Anteil beträgt im allgemeinen 0,1 bis 10 Gew.-%, insbesondere 1 bis 6 Gew.-%, be ofen auf die gesamte Riechstoffkomposition.Their fragrance is particularly beneficial in combination with other fragrances come into play. Thus, the compounds I are used together with other odoriferous substances in the most varied Mixing proportions of new fragrance compositions. Your share is generally 0.1 to 10% by weight, in particular 1 to 6% by weight, be ofen on the total Fragrance composition.

Bekannte Riechstoffe, mit denen die tert.-Alkoxy-benzaldehyde zu effektvollen Riechstoffkompositionen vermischt werden können, sind beispielsweise Phenylethyldimethylcarbinol, oC-Ionon, Linalylacetat, Terpineol, Farnesol, Tetrahydrojonol, Cumarin, Linalool, Citronellol, Cyclohexyl ethanol und Cyclohexylethylacetat.Known fragrances with which the tert-alkoxy-benzaldehydes become effective Fragrance compositions can be mixed, for example phenylethyldimethylcarbinol, oC-ionone, linalyl acetate, terpineol, farnesol, tetrahydrojonol, coumarin, linalool, Citronellol, cyclohexyl ethanol and cyclohexyl ethyl acetate.

Die erhaltenen Riechstoffkompositionen können direkt als Parfüms Anwendung finden oder aber zur Parfümierung von kosmetischen Zubereitungen aller Art sowie von Waschmitteln, Reinigungsmitteln und Aerosolen dienen.The fragrance compositions obtained can be used directly as perfumes or for perfuming cosmetic preparations of all kinds as well of detergents, cleaning agents and aerosols.

Von besonderer Bedeutung für die Erfindung ist, daß p-tert.--Butoxy- und p-tert.-Amyloxy-benzalhyd neuerdings wirtschaftlich sehr günstig in technischem Maßstab hergestellt werden können. Die Herstellung erfolgt gemäß einem Verfahren der nicht vorveröffentlichten DE-OS (Patentanmeldung P 2 935 298) durch elektrochemische Oxidation von p-tert.--Butoxy- bzw. p-tert.-Amyloxy-toluol in Gegenwart eines A1-kohols und anschließende Acetalspaltung.Of particular importance for the invention is that p-tert -butoxy- and p-tert-amyloxy-benzalhydrate has recently become very economical in technical terms Scale can be manufactured. The production takes place according to a process the unpublished DE-OS (patent application P 2 935 298) by electrochemical Oxidation of p-tert-butoxy- or p-tert-amyloxytoluene in the presence of an A1 alcohol and subsequent acetal cleavage.

Die p-tert.-Alkoxy-benzaldehyde sind Duftstoffe mit den begehrten sß-blumigen DuStnoten, die technisch sehr vorteilhaft zugängig sind und stellen daher eine wertvolle Bereicherung der Riechstoffpalette für die Parfümerie dar.The p-tert-alkoxy-benzaldehydes are fragrances with the most coveted Sweet-flowery DuSt notes, which are technically very advantageously accessible and provide therefore a valuable addition to the range of fragrances for perfumery.

Das nachfolgende Beispiel soll die Erfindung erläutern.The following example is intended to explain the invention.

Beispiel Parfümkomposition für Seifen und Cremes Phenylethyldimethylcarbinol 140 Gewichtsteile α-Jonon 20 Linalylacetat 120 " Hedione# (Markenzeichen der Firma Firmenich) 10 " Terpineol 50 " Farnesol 30 Fixolide (Markenzeichen der Firma Givaudan) 15 Aldehyd C 14 sogen. 10 %ig 10" α-Amylzimtaldehyd 120 " Tetrahydrojonol 15 " Cumarin 20 " Linalool 80 " Citronellol 100 " Cyclohexylethanol 35 1I Cyclohexylethylacetat 40 " SandiffX (Markenzeichen der Firma 30 " IFF) Beauvertate# (Markenzeichen der Firma Naarden) 15 p-tert.-Butoxybenzaldehyd 50 900 GewichtsteileExample perfume composition for soaps and creams Phenylethyldimethylcarbinol 140 parts by weight of α-ionone 20 linalyl acetate 120 "Hedione # (trademark of Firmenich) 10 "Terpineol 50" Farnesol 30 Fixolide (trademark of the company Givaudan) 15 aldehyde C 14 absorbed. 10% 10 "α-amylcinnamaldehyde 120" tetrahydrojonol 15 "Coumarin 20" Linalool 80 "Citronellol 100" Cyclohexylethanol 35 1I Cyclohexylethyl acetate 40 "SandiffX (trademark of 30" IFF) Beauvertate # (trademark of Naarden) 15 p-tert-butoxybenzaldehyde 50,900 parts by weight

Claims (3)

Patentansprüche 1. Riechstoffkomposition, enthaltend 0,1 bis 10 Gew.-% eines tert.-Alkoxy-benzaldehyds der allgemeinen Formel I in der R = H oder CH3 bedeutet, als Riechstoffkomponente neben anderen geruchsaktiven Stoffen.Claims 1. Fragrance composition containing 0.1 to 10 wt .-% of a tert-alkoxy-benzaldehyde of the general formula I. in which R = H or CH3, as a fragrance component in addition to other odor-active substances. 2. Riechstoffkomposition gemäß Anspruch 1 enthaltend 1 bis 6 Gew.-% eines tert.-Alkoxy-benzaldehyds der Formel I.2. Fragrance composition according to claim 1 containing 1 to 6 wt .-% of a tert-alkoxy-benzaldehyde of the formula I. 3. Verwendung von tert.-Alkoxy-benzaldehyden der allgemeinen Formel I anstelle von α-Methyl-p-tert.-butyl-dihydrozimtaldehyd oder α-Methyl-p-isopropyl-dihydrozimtaldehyd in Riechstoffkompositionen.3. Use of tert-alkoxy-benzaldehydes of the general formula I. instead of α-methyl-p-tert-butyl-dihydrocinnamaldehyde or α-methyl-p-isopropyl-dihydrocinnamaldehyde in fragrance compositions.
DE19823214658 1981-04-25 1982-04-21 Perfume compositions containing p-tert.-butoxy- and/or p-tert.-amyloxybenzaldehyde Withdrawn DE3214658A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19823214658 DE3214658A1 (en) 1981-04-25 1982-04-21 Perfume compositions containing p-tert.-butoxy- and/or p-tert.-amyloxybenzaldehyde

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3116556 1981-04-25
DE19823214658 DE3214658A1 (en) 1981-04-25 1982-04-21 Perfume compositions containing p-tert.-butoxy- and/or p-tert.-amyloxybenzaldehyde

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DE3214658A1 true DE3214658A1 (en) 1982-11-18

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0275489A1 (en) * 1986-12-23 1988-07-27 BASF Aktiengesellschaft Benzaldehyde derivatives, their preparation and application
US8236288B2 (en) 2011-01-07 2012-08-07 Skinmedica, Inc. Melanin modification compositions and methods of use
US8246971B2 (en) 2001-11-16 2012-08-21 Skinmedica, Inc. Compositions containing aromatic aldehydes and their use in treatment

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0275489A1 (en) * 1986-12-23 1988-07-27 BASF Aktiengesellschaft Benzaldehyde derivatives, their preparation and application
US8246971B2 (en) 2001-11-16 2012-08-21 Skinmedica, Inc. Compositions containing aromatic aldehydes and their use in treatment
US8246969B2 (en) 2001-11-16 2012-08-21 Skinmedica, Inc. Compositions containing aromatic aldehydes and their use in treatments
US8268336B2 (en) 2001-11-16 2012-09-18 Skinmedica, Inc. Compositions containing aromatic aldehydes and their use in treatments
US8496951B2 (en) 2001-11-16 2013-07-30 Allergan, Inc. Compositions containing aromatic aldehydes and their use in treatments
US9107874B2 (en) 2001-11-16 2015-08-18 Allergan, Inc. Compositions containing aromatic aldehydes and their use in treatments
US9895361B2 (en) 2001-11-16 2018-02-20 Allergan, Inc. Compositions containing aromatic aldehydes and their use in treatments
US10702515B2 (en) 2001-11-16 2020-07-07 Allergan, Inc. Compositions containing aromatic aldehydes and their use in treatments
US8236288B2 (en) 2011-01-07 2012-08-07 Skinmedica, Inc. Melanin modification compositions and methods of use
US8778315B2 (en) 2011-01-07 2014-07-15 Allergan, Inc. Melanin modification compositions and methods of use
US9044404B2 (en) 2011-01-07 2015-06-02 Allergan, Inc. Melanin modification compositions and methods of use

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