DE2347454A1 - PROCESS FOR THE PRODUCTION OF SMELL AND TASTE COMPOSITIONS - Google Patents

Description

Dr. ing. A. von der Werft 2 Sep. 1973

Br.ffuiii Lederef

^PAIENIANvm "23 47 45

6510/97

L. Givaudan & Cie Societe Anonyme, Vernier-Geneve (Switzerland)

Process for the production of fragrance and G-eschinaeksstoffkoniposi functions

The compounds of the formula

BT \ —CHO

E ²

1 p

wherein R is hydrogen, R isopropylidene or

1 2

Isopropenyl, or R together with R one Represent Dimethy! Methylengruppe,

so the 2-iOrmyl-1-isopropenyl-3-methyl-cyclopentane (substance a) the 2-pormyl-1-isopropylidene-3-methyl-cyclopentane (Substance B) and the 1,6,6-trimethylrbicycloCz.l.llhexane-a (Substance C) are known aldehydes (Tetrahedron 1 <J (1963), 1995-2007, J-Org. Chem. 2 £, (1958), 153-157). None of these

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Green / July 16, 1973

Connections, however, have hitherto been some kind of parfnishism Ascribed importance or importance as a flavoring substance.

It has now surprisingly been found that these aldehydes and mixtures of these aldehydes over a large amount of time have valuable fragrance and flavor qualities, because of which these compounds are excellent for improving ναι fragrance or flavor compositions of the Hesperides type, such as the Verveine type, are suitable.

The smell of 2-formyl-1-isopropylidene-3-methyl-cyclopentane can be described as fresh, minty and fruity.

The smell of 2-formyl-1-isopropenyl-3-methyl-cyclopentane is fresh, herbaceous, minty.

The smell of 1,6,6-trimethyl-bicyclo [2.1.1] hexane-a-a-mehyde is frisoh-spicy, it has a camphor-like undertone.

The real verveine oil (verbena oil) is only used to a limited extent in perfumery because of its high price, although it is superior to lemon oil, for example, in colognes and toilet waters because of its unusually intense, fresh, pure top note. For a long time there has therefore been a real need for cheaper fragrance compositions with the intensely fresh, finely lemon-like, balsamic odor note of genuine vervein oil, which is valued in perfumery and has a balsamic base.

It has now been found that fragrance compositions of this odor direction are obtained if citral or citral-containing mixtures with one or more

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compounds of the formula I are added.

The invention accordingly relates to a process for the production of fragrance or flavor body positions of the Hesperides type, which is characterized in that one citral or citral-containing compositions (fragrance or flavor compositions) a compound of the formula I clogs.

Formula I is intended to include all possible due to the asymmetric carbon atoms isomers include.

Stereo-

Examples of such isomers are in particular:

..CHO

CHO

... CHO

trans / trans-Photocitral A

epi-Photo- Photo- eis, eis- Photocitral A citral A Photocitral A citral B

The inventive addition of the substance A,. B or C or a mixture of several of these substances, in sterically uniform form or in the form of Mixtures of stereoisomers can vary within wide limits. In fragrance compositions, for example, IO to 80% by weight, preferably 30 "to 70% by weight of the above ~ existing amount of citral can be replaced by the corresponding amount of compounds A and / or B and / or C. Will as a fragrance composition e.g. a perfume base (concentrate of fragrances) used, which 0.1 to 10 wt. # Citral contains, satisfactory results are obtained through. additions in the range from about 0.03 to 7 weight percent, one or more

of the compounds of the formula I. -..- · _

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The concentration of the compound (s) in the finished product (e.g. in the ready-to-use perfume, toilet water, Cologne or in a perfumed product such as a soap, ointment, powder or other cosmetic Product) can naturally be well below $ 0.03.

In the production of flavor compositions can be a fruit flavor containing, for example 0.1-10% by weight citral one or more compounds of the formula I are added in amounts of a few parts per thousand to flavor compositions with a green hesperid note. The aromas obtained can be used, for example, in liquids, pastes or powders. The products can e.g. be spray-dried, vacuum-dried or lyophilized. The formulation of such flavors as well as the flavoring of Food and beverages can be found on known manner and method (cf. e.g. J. Merory, Food flavors, composition, manufacture and use; Avi Publ. Co. Inc., Westport 1968).

The compounds of formula I can be used

are used to produce flavor compositions in foods (e.g. yoghurt, puddings, etc.), in luxury foods (e.g. confectionery products such as candies, soft ice, etc.) and in beverages (e.g. mineral waters, syrups).

Example 1 Fragrance Composition (Type Kölnisch V / ater)

Parts by weight

Terpenyl acetate 100

Linalyl acetate - 100

Xavandin Oil 130

Orange oil Italian 150

Petitgrain oil 50

Α09817 / 072Λ

Lavender oil 50

Lilial (p-tert-butyl-α-ine thy lhydrocinnamaldehyde) 40 Ainbrett Musk 20

Versalide (1,1,4,4-tetrainethyl-6 «-ä-ethyl-7-acetyl-1,2,3,4-tetrahydronaphthalene) 20th

Resinoid Benzoin Siam 20

Cyclamen aldehyde 20

Cetone V (AlIy 1-a-j onon) 20

Lavone (3-methyl-octan-2-one) 40 Nerone (l- (p-menthen-6-yl) -l-propanone. 15

Jasmine absolute synthetic 100

Galbanum oil 10 % in phthalic acid diethyl ester 20

Cetonal (4- [2,2,6-trimethyl-cyclo-2-en-yl] -2-

me thy1-butanaI) 5

Citral _JLOO

1000

The smell of this composition of the Kölnisch-V / ater type has an herbaceous-flowery undertone. The citral dominates the composition in terms of smell and appears hard. By replacing J> 0 $> of the citral with a photocitral mixture (58 $ photocitral A, 16% photocitral B, 6 # 'epi-photocitral A and J)% trans, trans-photocitral A) there is a very significant improvement in the Smell achieved: The smell of the composition appears softer and more natural in the direction of not fully ripe lemons.

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Example 2

Fruit aroma bouquet (Tutti-Frutti type, based on ester) Weightstoi3.e Capronaldehyde 1 Capric acid 10? O in ethanol 1 Caprylic acid 10'fo in ethanol 1 Caproic acid $ 10 in ethanol 1 Sandalwood oil 1 Bulgarian rose oil 1 Jasmine Absolu 1 Anethole natural 1 Petitgrain oil 1 Phenylethyl alcohol 1 1 Butyric butyrate 1 Benzaldehyde Ihibetolide 1 Linalyl phenylacetate 2 Butyric acid terpenyl ester 2 Linalyl acetate 2 Ethyl acetate 2 Piperonyl acetate 2 Butyric acid esters 2 Benzoic acid geranyl ester 2 Benzoic acid benzyl ester 2 Elinalyl caprylate 3 Aldehyde C 18 IO Linalool 10 Pelargonic acid ethyl ester 10 Citronellol 12th Vanillin 12th Aldehyde C 14 12th Ethyl caproate 20th a-ionone 20th

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2347A54

Butyric acid amyl ester 20

Citral 50

Acetaldehyde 50

Butyric acid ethyl ester 200

Lauryl alcohol 200

d-limonene. 341

1000

The addition of 5 # o_Photocitral - Geinisch (58 ^ Photooitral A, 16% Photocitral B, 6% epi-Photocitral A and J>% trans, trans-Photocitral A) to the above composition changes its sensory properties in the direction of a peeled, green one Hesperiden note, whereby the strong ester note in particular is modified, ie reduced, in a pleasantly surprising way.

4098 1 7 / 072A

Claims (1)

Claims 1. Process for the production of olfactory or gustatory compositions , characterized in that one citral or citral-containing compositions a compound the formula CHO 1 2 wherein R is hydrogen, R isopropylidene or 1 ~ 2 Isopropenyl, or R together with R is a dimethyl represent methylene group,
clogs. 2. The method according to claim 1, characterized in that that as a compound of the formula I 2-Fonayl-1-isopropenyl-3-methyl-cyclopentane used. 3. The method according to claim 1, characterized in that the compound of formula I is 2-formyl-1-isopropylidene-3-methyl-cyclopentane used. " 4. The method according to claim 1, characterized in that the 1,6,6-trimethylbicyclo [2.1.1] hexane-2-aldehyde is used as the compound of the formula I used. 4098 17/0724