EP0168415B1 - Utilization of salicylic acid esters as perfuming substances, perfuming compositions containing them and new salicylic acid esters - Google Patents

Utilization of salicylic acid esters as perfuming substances, perfuming compositions containing them and new salicylic acid esters Download PDF

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Publication number
EP0168415B1
EP0168415B1 EP85900107A EP85900107A EP0168415B1 EP 0168415 B1 EP0168415 B1 EP 0168415B1 EP 85900107 A EP85900107 A EP 85900107A EP 85900107 A EP85900107 A EP 85900107A EP 0168415 B1 EP0168415 B1 EP 0168415B1
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Prior art keywords
salicylic acid
acid esters
salicylate
perfuming
utilization
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EP85900107A
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German (de)
French (fr)
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EP0168415A1 (en
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Ulf-Armin Schaper
Benno Streschnak
Siegfried BLÖSL
Walter Sommer
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BASF Personal Care and Nutrition GmbH
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Henkel AG and Co KGaA
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    • 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

Definitions

  • esters of salicylic acid are known from the literature. Some esters have found use in the fragrance industry, e.g. the methyl, butyl, amyl, hexyl, benzyl and 3-hexenylsalicylic acid esters (S. Arctander, Perfume and Flavor Chemicals, 1969; and PZ Bedoukian, Perfum. Flavor 6 (5), 60-61 (1981). )
  • the salicylic acid esters are prepared by known methods by esterifying salicylic acid with a carbocyclic alcohol corresponding to the definition of the general formula, if appropriate in the presence of acidic or alkaline catalysts and with removal of the water thereby released, or by reacting salicylic acid chloride with the alkali metal alcoholate of the carbocyclic alcohol, or by transesterification of methyl salicylate with the carbocyclic alcohol.
  • the olfactory characteristics of the salicylic acid esters in question can generally be described with a flowery, typical salicylate note, whereby in individual cases floral, aromatic, balsamic notes essentially determine the smell.
  • the claimed esters can be combined to create new, interesting fragrance compositions.
  • Such compositions can serve for the perfuming of cosmetics, such as scented water, creams, lotions, aerosols, toilet soaps, in a terapéutica, and for improving the odor of technical articles, such as cleaning agents, disinfectants, textile treatment agents and the like.
  • the esters are of particular interest for the perfuming of textile detergents, fabric softeners and cosmetics.
  • the compositions mentioned are added to the various products in amounts of 0.05 to 2 percent by weight, based on the entire product.
  • the claimed esters are furthermore distinguished by an extraordinarily good resistance to the odor. They do not develop any unpleasant odors even after the products perfumed with them have been stored for a long time.
  • the cyclopentyl and the cyclohexyl esters are particularly preferred for use under practical conditions because of their strong-smelling odor and their adhesive strength and at the same time great stability towards aggressive media.
  • Cyclohexyl salicylate was incorporated 1.5% in basic soap.
  • the forearm of a test person was foamed with the soap for 15 s and the smell of the foam was assessed. The foam was then rinsed off, the arm was dried and the remaining odor was assessed over several hours.
  • the benzyl salicylate known as a fragrance was used. Radiance and adhesive strength were assessed according to the following scheme.
  • cyclohexyl salicylate 0.3% was incorporated as perfuming agent into the formulation of a commercially available laundry softener based on cationic quaternary ammonium compounds, emulsifiers, viscosity regulators, solvents and diluents.
  • 0.15% cyclohexyl salicylate as a perfuming agent was incorporated into the formulation of a commercial heavy-duty detergent based on anionic and nonionic surfactants, builder substances, complexing agents, perborate, graying inhibitors, dirt carriers, brighteners and fillers.
  • a second batch was perfumed with 0.15% benzyl salicylate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Paper (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Beans For Foods Or Fodder (AREA)

Abstract

Utilization of salicylic acid-cycloalkyl- or alkenyl esters (ring size: C5-C9) as perfuming substances, and perfuming compositions containing them, as well as new salicylic acid-cycloalkyl esters.

Description

Aus der Literatur ist eine Vielzahl von Estern der Salicylsäure bekannt. Einige Ester haben Verwendung in der Riechstoffindustrie gefunden, z.B. der Methyl-, Butyl-, Amyl-, Hexyl-, Benzyl- und 3-Hexenylsalicylsäureester (S. Arctander, Perfume and Flavor Chemicals, 1969; sowie P.Z. Bedoukian, Perfum. Flavor 6 (5), 60-61 (1981).)A large number of esters of salicylic acid are known from the literature. Some esters have found use in the fragrance industry, e.g. the methyl, butyl, amyl, hexyl, benzyl and 3-hexenylsalicylic acid esters (S. Arctander, Perfume and Flavor Chemicals, 1969; and PZ Bedoukian, Perfum. Flavor 6 (5), 60-61 (1981). )

Es wurde nun eine Gruppe von Salicylsäureestern gefunden, die sich durch überraschende und wertvolle Riechstoffeigenschaften, insbesondere eine sehr hohe Haftfestigkeit auszeichnen. Es handelt sich hierbei um die Salicylsäureester carbocyclischer, nicht-aromatischer Alkohole. Die Ester werden durch die folgende allgemeine Formel charakterisiert.

Figure imgb0001

  • R = Cycloalkyl oder Cycloalkenyl, gegebenenfalls substituiert durch Alkyl Cl-C4, wobei die Summe der C-Atome in R = 5 - 9 beträgt.
  • n = 0 - 3.
A group of salicylic acid esters has now been found which is distinguished by surprising and valuable fragrance properties, in particular a very high adhesive strength. These are the salicylic acid esters of carbocyclic, non-aromatic alcohols. The esters are characterized by the following general formula.
Figure imgb0001
  • R = cycloalkyl or cycloalkenyl, optionally substituted by alkyl C 1 -C 4 , the sum of the C atoms in R = 5-9.
  • n = 0-3.

Wegen ihres ausgeprägten Geruchsbildes sind die Ester, bei denen die Summe der C-Atome in R = 5-6 beträgt, und n = 0 oder 1 ist, besonders hervorzuheben.The esters, in which the sum of the C atoms in R = 5-6 and n = 0 or 1, are particularly noteworthy because of their distinctive odor pattern.

Die Herstellung der Salicylsäureester erfolgt nach bekannten Methoden durch Veresterung von Salicylsäure mit einem der Definition der allgemeinen Formel entsprechenden carbocyclischen Alkohol, gegebenenfalls in Gegenwart saurer oder alkalischer Katalysatoren und unter Abtrennen des dabei freiwerdenden Wassers, oder durch Umsetzung von Salicylsäurechlorid mit dem Alkalialkoholat des carbocyclischen Alkohols, oder durch Umesterung von Methylsalicylat mit dem carbocyclischen Alkohol.The salicylic acid esters are prepared by known methods by esterifying salicylic acid with a carbocyclic alcohol corresponding to the definition of the general formula, if appropriate in the presence of acidic or alkaline catalysts and with removal of the water thereby released, or by reacting salicylic acid chloride with the alkali metal alcoholate of the carbocyclic alcohol, or by transesterification of methyl salicylate with the carbocyclic alcohol.

Einige der unter die allgemeine Formel fallenden Verbindungen sind aus der Literatur bekannt, ohne daß auf ihre Riechstoffeigenschaften hingewiesen wurde.Some of the compounds covered by the general formula are known from the literature without reference to their fragrance properties.

Weitere dieser Verbindungen mit besonders interessanten Riechstoffeigenschaften sind neue Verbindungen und werden daher auch als solche beansprucht.Other of these compounds with particularly interesting fragrance properties are new compounds and are therefore also claimed as such.

Die Geruchscharakteristik der in Frage stehenden Salicylsäureester läßt sich generell mit blumig, typische Salicylat-Note beschreiben, wobei im Einzelfall blumige, aromatische, balsamische Noten das Geruchsbild wesentlich bestimmen.The olfactory characteristics of the salicylic acid esters in question can generally be described with a flowery, typical salicylate note, whereby in individual cases floral, aromatic, balsamic notes essentially determine the smell.

In Verbindung mit anderen Riechstoffen und/oder gängigen Parfümbestandteilen lassen sich die beanspruchten Ester zu neuen, interessanten Riechstoffkompositionen kombinieren. Dabei werden etwa 1 - 50 Gewichtsprozent der Verbindungen, bezogen auf die gesamte Komposition, eingesetzt. Derartige Kompositionen können zur Parfümierung von Kosmetika, wie Duftwässern, Cremes, Lotionen, Aerosolen, Toilettenseifen, in der Extrait-Parfümerie, sowie zur Geruchsverbesserung von technischen Artikeln, wie Reinigungsmitteln, Desinfektionsmitteln, Textilbehandlungsmitteln und dergleichen dienen. Wegen ihrer ungewöhnlichen Ausstrahlungskraft und Haftfestigkeit sind die Ester zur Parfümierung von Textilwaschmitteln, Weichspülmitteln und Kosmetika von besonderem Interesse. Die genannten Kompositionen werden den verschiedenen Produkten in Mengen von 0,05 bis 2 Gewichtsprozent, bezogen auf das gesamte Produkt, zugesetzt.In combination with other fragrances and / or common perfume ingredients, the claimed esters can be combined to create new, interesting fragrance compositions. About 1 - 50 percent by weight of the compounds, based on the overall composition, are used. Such compositions can serve for the perfuming of cosmetics, such as scented water, creams, lotions, aerosols, toilet soaps, in extrait perfumery, and for improving the odor of technical articles, such as cleaning agents, disinfectants, textile treatment agents and the like. Because of their unusual charisma and adhesive strength, the esters are of particular interest for the perfuming of textile detergents, fabric softeners and cosmetics. The compositions mentioned are added to the various products in amounts of 0.05 to 2 percent by weight, based on the entire product.

Die beanspruchten Ester zeichnen sich weiterhin durch eine außerordentlich gute Beständigkeit des Geruchsbildes aus. Sie entwickeln auch nach längerer Lagerzeit der damit parfümierten Produkte keine unangenehmen Nebengerüche. Der Cyclopentyl- und der Cyclohexylester werden wegen ihres strahlkräftigen Geruches und ihrer Haftfestigkeit bei gleichzeitig großer Stabilität gegenüber agressiven Medien für die Anwendung unter Praxisbedingungen besonders bevorzugt.The claimed esters are furthermore distinguished by an extraordinarily good resistance to the odor. They do not develop any unpleasant odors even after the products perfumed with them have been stored for a long time. The cyclopentyl and the cyclohexyl esters are particularly preferred for use under practical conditions because of their strong-smelling odor and their adhesive strength and at the same time great stability towards aggressive media.

BeispieleExamples Allgemeine Arbeitsvorschrift für ein VeresterungsverfahrenGeneral working instructions for an esterification process

1 Mol Salicylsäuremethylester und 2 Mol des betreffenden Alkohols werden vorgelegt. Bei 60 bis 65°C werden unter Rühren langsam 18 g (0,1 Mol) 30 %ige Natriummethylat-Lösung zugetropft. Nach beendeter Zugabe wird über eine Claisenbrücke das freigesetzte Methanol abdestilliert. Dabei steigt die Sumpftemperatur auf ca. 1700 C.1 mol of methyl salicylic acid and 2 mol of the alcohol in question are presented. At 60 to 65 ° C, 18 g (0.1 mol) of 30% sodium methylate solution are slowly added dropwise with stirring. When the addition is complete, the methanol released is distilled off via a Claisen bridge. The bottom temperature rises to about 170 0 C.

Nach beendeter Umesterung wird der Rückstand in Wasser aufgenommen und mit Ether extrahiert. Der Etherextrakt wird neutral gewaschen, über Natriumsulfat getrocknet und eingeengt.After the transesterification, the residue is taken up in water and extracted with ether. The ether extract is washed neutral, dried over sodium sulfate and concentrated.

Das Rohprodukt ergibt nach Destillation über eine Füllkörperkolonne den gewünschten Ester.After distillation via a packed column, the crude product gives the desired ester.

Figure imgb0002
Figure imgb0002

11. Parfümierung von Seife11. Perfuming soap

Cyclohexylsalicylat wurde 1,5 %ig in Grundseife eingearbeitet. Mit der Seife wurde der Unterarm einer Versuchsperson 15 s eingeschäumt und der Geruch des Schaumes beurteilt. Danach wurde der Schaum abgespült, der Arm abgetrocknet und über mehrere Stunden der verbleibende Geruch beurteilt. Zum Vergleich wurde das als Riechstoff bekannte Benzylsalicylat eingesetzt. Ausstrahlungskraft beziehungsweise Haftfestigkeit wurden nach folgendem Schema beurteilt.

Figure imgb0003
Figure imgb0004
 Cyclohexyl salicylate was incorporated 1.5% in basic soap. The forearm of a test person was foamed with the soap for 15 s and the smell of the foam was assessed. The foam was then rinsed off, the arm was dried and the remaining odor was assessed over several hours. For comparison, the benzyl salicylate known as a fragrance was used. Radiance and adhesive strength were assessed according to the following scheme.
Figure imgb0003
Figure imgb0004

12. Parfümierung eines Wäsche-Weichspülers12. Perfuming a laundry softener

In die Rezeptur eines handelsüblichen Wäsche-Weichspülmittels auf der Basis von kationaktiven quaternären Ammoniumverbindungen, Emulgatoren, Viskositätsstellmitteln, Löse- und Verdünnungsmitteln wurden als Parfümierungsmittel 0,3 % Cyclohexylsalicylat eingearbeitet.0.3% cyclohexyl salicylate was incorporated as perfuming agent into the formulation of a commercially available laundry softener based on cationic quaternary ammonium compounds, emulsifiers, viscosity regulators, solvents and diluents.

Zum Vergleich diente eine mit 0,3 % Benzylsalicylat parfümierte Rezeptur.A recipe perfumed with 0.3% benzyl salicylate was used for comparison.

Drei verschiedene Tücher aus Baumwolle (BW), Polyester (PE) und Baumwolle/Polyestermischgewebe (M) wurden in einer Waschmaschine mit 100 ml dieses Weichspülers gespült. Die ausgeschleuderten Tücher wurden sowohl feucht, wie nach dem Trocknen (über Nacht auf der Leine) geruchlich beurteilt (vergleiche Beispiel 11). Außerdem wurden die Tücher trocken gelagert (in Polyethylenbeutel verpackt) und nach verschiedenen Zeiten erneut beurteilt.

Figure imgb0005
Three different cloths made of cotton (BW), polyester (PE) and cotton / polyester blend (M) were rinsed in a washing machine with 100 ml of this fabric softener. The spun cloths were assessed both wet and olfactory after drying (on a line overnight) (see Example 11). In addition, the wipes were stored dry (packed in polyethylene bags) and reassessed after various times.
Figure imgb0005

13. Parfümierung eines Waschmittels13. Perfuming a detergent

In die Rezeptur eines handelsüblichen Vollwaschmittels auf der Basis von anionischen und nichtionischen Tensiden, Buildersubstanzen, Komplexbildnern, Perborat, Vergrauungsinhibitoren, Schmutzträgern, Aufhellern und Füllstoffen wurden 0,15 % Cyclohexylsalicylat als Parfümierungsmittel eingearbeitet. Zum Vergleich wurde ein zweiter Ansatz mit 0,15 % Benzylsalicylat parfümiert.0.15% cyclohexyl salicylate as a perfuming agent was incorporated into the formulation of a commercial heavy-duty detergent based on anionic and nonionic surfactants, builder substances, complexing agents, perborate, graying inhibitors, dirt carriers, brighteners and fillers. For comparison, a second batch was perfumed with 0.15% benzyl salicylate.

Mit dem Waschmittel wurde normal verschmutzte Wäsche in einer Trommelwaschmaschine im Vor- und Hauptwaschgang gewaschen.Normally soiled laundry was washed with the detergent in a drum washing machine in the pre and main wash cycle.

Nach dem Vor- beziehungsweise Hauptwaschgang wurde

  • a) der Geruch der Lauge nach dem Spülen und Schleudern,
  • b) der Geruch der feuchten Wäsche wie in Beispiel 12 angegeben, beurteilt.
    Figure imgb0006
After the pre or main wash
  • a) the smell of the lye after rinsing and spinning,
  • b) the smell of the damp laundry as stated in Example 12, assessed.
    Figure imgb0006

Claims (11)

1. The use of salicylic acid esters corresponding to the following general formula
Figure imgb0009
in which
R = cycloalkyl or cycloalkenyl optionally substituted by Cl-C4 alkyl, the sum of the C-atoms in R = 5 - 9,
n = 0 - 3,

as perfuming agents.
2. The use of the salicylic acid esters corresponding to the general formula in Claim 1 in which the sum of the C-atoms in R = 5 - 6 and n = 0 or 1.
3. The use of cyclopentyl salicylate or cyclohexyl salicylate as perfuming agents.
4. Perfume compositions characterised by a content of from 1 to 50 % by weight of salicylic acid esters as claimed in Claims 1 to 3.
5. Cyclopentyl salicylate.
6. 2,2,4-(2,4,4-) trimethyl cyclopentyl salicylate as an isomer mixture.
7. 4-isopropyl cyclohexyl salicylate.
8. Cyclohexylmethyl salicylate.
9. Cycloheptyl salicylate.
10. Cyclooctyl salicylate.
11. Cyclooct-4-enyl salicylate.
EP85900107A 1984-01-07 1984-12-14 Utilization of salicylic acid esters as perfuming substances, perfuming compositions containing them and new salicylic acid esters Expired EP0168415B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85900107T ATE28892T1 (en) 1984-01-07 1984-12-14 USE OF SALICYLIC ACID ESTERS AS FRAGRANCES, FRAGRANCE COMPOSITIONS CONTAINING THEM, AND NEW SALICYLIC ACID ESTERS.

Applications Claiming Priority (2)

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DE19843400342 DE3400342A1 (en) 1984-01-07 1984-01-07 USE OF SALICYL ACID ESTERS AS A FRAGRANT, THESE COMPOSITIONS CONTAINING IT, AND NEW SALICYL ACID ESTERS
DE3400342 1984-01-07

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EP0168415B1 true EP0168415B1 (en) 1987-08-12

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US (1) US4624802A (en)
EP (1) EP0168415B1 (en)
JP (1) JPH0739589B2 (en)
AU (1) AU575115B2 (en)
BR (1) BR8407262A (en)
CA (1) CA1292238C (en)
DE (2) DE3400342A1 (en)
ES (1) ES8607207A1 (en)
GB (1) GB2152374B (en)
HK (1) HK93687A (en)
IT (1) IT1196379B (en)
MY (1) MY100883A (en)
SG (1) SG57087G (en)
WO (1) WO1985003084A1 (en)
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WO2024037712A1 (en) 2022-08-17 2024-02-22 Symrise Ag 1-cyclooctylpropan-2-one as a fragrance

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US5232897A (en) * 1990-05-15 1993-08-03 Sumitomo Chemical Company, Limited Herbicidal pyrimidine compounds, compositions containing the same and method of use
AU645452B2 (en) * 1990-05-15 1994-01-13 Sumitomo Chemical Company, Limited Intermediate useful in the production of pyrimidine derivatives having herbicidal activity
US5298632A (en) * 1990-05-15 1994-03-29 Sumitomo Chemical Company, Limited Herbicidal pyrimidine compounds, compositions containing the same and method of use
CA2041615A1 (en) * 1990-05-15 1991-11-16 Mitsunori Hiratsuka Pyrimidine derivatives
DE4344358A1 (en) * 1993-12-24 1995-06-29 Henkel Kgaa Process for working up a reaction mixture by means of a column placed on the reactor
DE69512717T2 (en) * 1994-07-01 2000-11-16 Firmenich S.A., Genf/Geneve Cyclic diester and use thereof as a fragrance
GB2303789A (en) * 1995-07-29 1997-03-05 Procter & Gamble Perfumed compositions containing formaldehyde generating preservatives
FR2740450B1 (en) * 1995-10-27 2001-09-28 Rhone Poulenc Chimie PROCESS FOR OBTAINING PERFUMING COMPOSITIONS AND PERFUMED PRODUCTS AND PRODUCTS THUS OBTAINED
US6939835B2 (en) * 1999-03-26 2005-09-06 Firmenich Sa Cyclic compounds and their use as precursors of fragrant alcohols
DE10248952A1 (en) * 2002-10-21 2004-04-29 Bayer Ag Polycarbonates, polyester carbonates and polyesters with laterally positioned cycloalkyl-substituted phenols
US6916899B2 (en) * 2002-10-21 2005-07-12 Bayer Aktiengesellschaft Polycarbonates, polyester carbonates and polyesters having lateral, cycloalkyl-substituted phenols
US20050032672A1 (en) * 2003-08-06 2005-02-10 Narula Anubhav P.S. Fragrance compositions
GB0518558D0 (en) * 2005-09-12 2005-10-19 Givaudan Sa Improvements in or related to organic compounds
WO2008009914A1 (en) * 2006-07-17 2008-01-24 Flexitral, Inc. Thiophenemethyl salicylate and related compounds as flavours and fragrances
CN105541634A (en) * 2014-11-04 2016-05-04 南京秾康生物科技有限公司 Synthetic method of homosalate
CN112858650B (en) * 2021-01-13 2023-08-18 上海应用技术大学 Analysis and research method for improving automobile leather smell based on sigma-tau strength method

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US3714227A (en) * 1970-09-04 1973-01-30 Ueno Seiyaku Oyo Kenkyujo Kk Process for the preparation of p-hydroxybenzoic acid ester alkali metal salts
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Publication number Priority date Publication date Assignee Title
WO2024037712A1 (en) 2022-08-17 2024-02-22 Symrise Ag 1-cyclooctylpropan-2-one as a fragrance

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ZA85104B (en) 1985-09-25
AU575115B2 (en) 1988-07-21
GB2152374A (en) 1985-08-07
EP0168415A1 (en) 1986-01-22
GB8500253D0 (en) 1985-02-13
US4624802A (en) 1986-11-25
JPS60160040A (en) 1985-08-21
AU3830985A (en) 1985-07-30
JPH0739589B2 (en) 1995-05-01
MY100883A (en) 1991-05-16
DE3400342A1 (en) 1985-07-18
ES8607207A1 (en) 1986-05-16
BR8407262A (en) 1985-12-24
DE3465333D1 (en) 1987-09-17
GB2152374B (en) 1987-05-13
ES539388A0 (en) 1986-05-16
SG57087G (en) 1987-09-18
WO1985003084A1 (en) 1985-07-18
IT8424209A0 (en) 1984-12-21
IT1196379B (en) 1988-11-16
HK93687A (en) 1987-12-18

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