CH600799A5 - Aromatising flavourings for tobacco, food, drink etc. - Google Patents

Abstract

Aromatising component, partic. for tobacco or tobacco prods. comprises polycyclic carbonyl cpd. (a) santalone; or (b) 5,6-dimethyl-norbornene-2-yl acetate.Various taste notes can be developed by the additives generally woody and sweet, sometimes balsamic, earthy or camphorated. They are suitable for inclusion in compsn to flavour huma and animal food, drinks, and pharmaceutical prepns., partic. pastries, sweets, syrups and liqueurs in which spiced or fruity notes are required. The cpds. are constituents of the essential oil of Oriental Sandalwood.

Description

  

  
 



   The essential oil of oriental sandalwood is one of the oldest perfume substances. It is obtained by steam entrainment of the wood and roots of Santalum album L., a tree cultivated in particular in India. Its olfactory properties, at the same time woody, sweet, animal and balsamic, are highly prized by perfumers, hence its use in a good number of perfume compositions. On the other hand, its use as a flavoring agent has not been judged, to date, of very great interest.



   We have now discovered that, among the constituents of this essence, there are certain compounds which, by virtue of their organoleptic properties, find a very advantageous use as flavoring ingredients.



   The subject of the present invention is therefore the use, as flavoring ingredient, of one of the compounds below:
 a) sandalone;
 b) 5,6-Dimethyl-5-norbornene.2-yl acetate.



   In the list below, following the designation of each of the compounds, its structural formula and the bibliographical reference mentioning a method for obtaining said compounds appear.



   The results of the organoleptic evaluation tests are given in the specific examples.
EMI1.1


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  Compound <SEP> Formula <SEP> Bibliographic <SEP> reference
<tb> <SEP> COCH3
<tb> a) <SEP> <<SEP> / <SEP> t <SEP> Arch. <SEP> Pharmaz. , <SEP> 238, <SEP> 372 <SEP> (1900),
<tb> <SEP> see <SEP> experimental <SEP> part.
<tb>



  b) <SEP> t <SEP> / <SEP> in <SEP> See <SEP> experimental <SEP> part.
<tb>



   <SEP> CH3COO
<tb>
Experimental part (temperatures are indicated in degrees centigrade)
 a) Santalone
 IR: 1695, 1350, 1275, 1450, 1070, 3050 cm-1;
 MS: m / e: 43 (50), 79 (27), 93 (100), 105 (20), 121 (72), M + = 164 (59);
 NMR: 0.78 (1H, m); 1.04 (3H, s); 1.20 (3H, s); 0.9-2.2 (6H, m);
 2.00 (3H, s) 6 ppm.



   The name of santalone was given by Müller, Arch. Pharmaz. , 238, 372 (1900), to a compound of the molecular formula C1 1H16O.



  The compound which we prepared according to the method indicated below probably corresponds to the product indicated by Müller. 9.6 g (57 mM) of teresantalic acid in 25 ml of anhydrous ether was added at -25 ", under a nitrogen atmosphere and with vigorous stirring, to a solution of methyllithium, the latter having been prepared. from 20.5 g (144 mM) of methyl iodide and 2.03 g (293 mM) of lithium in 80 ml of anhydrous ether The reaction mixture was kept under stirring for 30 min at -20. 'and then 2 hours to 20 hours, then heated to reflux for 20 hours By the usual treatments followed by alkaline extraction, 4.4 g of sandalone were obtained.

  Purification was carried out by chromatography on a column of silica gel (eluent: benzene / ethyl acetate 95: 5) and gas chromatography.



   b) 5,6-Dimethyl-5-norbornene-2-yl acetate.



   48.9 g (90% purity; 99 mM) of lead acetate was added under a nitrogen atmosphere to a solution of teresantalic acid (8.2 g; 49.4 mM) in 5.86 g (74 , 1 mM) of anhydrous pyridine and 100 ml of benzene. The reaction mixture was kept under reflux for 6-7 h then, after cooling, it was chromatographed on a column of silica gel (30 parts of silica gel
Mallinckrodt 100 mesh, analytical reagent). Distillation of the eluted fraction with 1000 ml of benzene provided 6.82 g (76%) of an 85:15 mixture of acetates of the formula:
EMI1.2
 said mixture having Eb. 82/10 torr.



   This mixture was reduced with 1.3 g (34 mM) of lithium aluminum hydride in ether at reflux.



   The usual decomposition treatments with an aqueous solution of ammonium chloride followed by extraction with ether and distillation of the ethereal phase gave 4.81 g (92%) of an 85:15 mixture of the alcohol of formula:
EMI1.3
 and 5,6-dimethyl-5-norbornene-exo-2-ol.



   40 g of acetic acid, containing 12 drops of concentrated sulfuric acid, was added at 0 to a solution of said mixture of alcohols (4.0 g; 29 mM) in 4.0 g of acetic acid. The reaction mixture was slowly (5h) warmed to 20, then allowed to stand for 5h at 20.



   The usual processing provided 3.1 g (59%) of the acetate of the formula:
EMI1.4
   87% pure.



   The flavoring ingredients of the invention can be used in various forms. However, it is preferable to use these products or these compositions in the form of solutions. The nature, solubility and stability of the product determine the form in which the composition or flavoring agent is to be used.



   For the flavoring of tobacco, for example, one suitable means consists in sprinkling the tobacco with an alcoholic solution of the product or of the flavoring composition. Mixtures of alcohol and propylene glycol can also be used as solvent.



   Thanks to the use of the flavoring ingredients of the invention, it is possible to develop in the products to which they are added various taste notes, generally woody, sweet, sometimes balsamic, earthy or camphorated. These organoleptic characteristics are suitable for the preparation of compositions intended for flavoring food, for humans and animals, drinks, pharmaceutical preparations and tobacco.



   Among the foods which can be flavored in this way, it is most particularly appropriate to mention pastry and biscuit products, candies, syrups, liqueurs in which spicy or fruity notes are desired. The proportions for the application of the compounds of the invention in flavoring compositions, or for their use according to the process of the invention, can vary within a fairly wide range of values.



  For example, interesting flavoring effects can be obtained with amounts on the order of 0.5 to 50 ppm (parts per million), amounts based on the weight of the flavored material.

 

  Preferred concentrations are between about 5 and 10 ppm, for flavoring foods and beverages in general, and between 10 and 20 ppm for flavoring tobacco.



   In all cases, the limits indicated above can of course vary according to the flavoring effect sought. The table lists the products evaluated and mentions the aroma developed.



  This was determined by a group of flavoring experts who evaluated said products in a standard sweet drink prepared by dissolving 600 g of sucrose in 1000 ml of spring water. Such a drink represents a base commonly used in the art for determining the flavoring characteristics exhibited by a given ingredient.



   Compound Organoleptic evaluation
 a) woody, rosemary
 b) woody, fruity

 

Claims (1)

CLAIM Use as a flavoring ingredient of one of the following compounds: a) sandalone; b) 5,6-dimethyl-5-norbornene-2-yl acetate. SUB-CLAIM Use according to claim, characterized in that said compounds are added to tobacco or to tobacco products.