Patent Publication Number: US-2006013837-A1

Title: Flavour compositions

Description:
FIELD OF THE INVENTION  
      This invention relates to flavour compositions and concerns flavour compositions having cinnamon flavour and also concerns consumer products, particularly but not exclusively oral care products, including the flavour compositions.  
     BACKGROUND TO THE INVENTION  
      Cinnamon is a well known flavour type that is popular with consumers and is widely used in a range of consumer products including oral care products and chewing gum preparations. The desired cinnamon character can be incorporated into a flavour composition by use of cinnamic aldehyde. Cinnamic aldehyde may be used as cinnamic aldehyde itself or in the form of a natural oil containing cinnamic aldehyde, e.g. cinnamon bark oil derived from the inner bark of the Cinnamomum Zeylandicum, preferably the variety grown in Ceylon, or cassia oil (Chinese cinnamon oil) derived from the leaves of Cinnamomum Cassia.  
      Cinnamic aldehyde has been shown to have sensitiser properties, which means that use of cinnamic aldehyde (and oils containing cinnamic aldehyde) is limited in cosmetic and oral care products.  
     SUMMARY OF THE INVENTION  
      In one aspect the present invention provides a flavour composition comprising cinnamic alcohol and eugenol, the cinnamic alcohol and eugenol together comprising at least 3% by weight of the total weight of the composition, the weight ratio of cinnamic alcohol to eugenol being in the range 0.25:1 to 3.5:1.  
      Surprisingly, it is found that such mixtures of cinnamic alcohol and eugenol provide a cinnamon flavour without requiring the presence of cinnamic aldehyde (either as such or in the form of a cinnamic aldehyde-containing oil).  
      A flavour composition in accordance with the invention desirably contains no or substantially no cinnamic aldehyde, with cinnamic aldehyde comprising less than 0.1% by weight of the composition, preferably less than 0.05% by weight of the composition, more preferably less than 0.001% by weight of the composition, and ideally being completely absent.  
      The cinnamic alcohol and eugenol together preferably comprise at least 5% by weight of the total weight of the composition and possibly significantly more, up to 100% in the extreme case. The amounts of cinnamic alcohol and eugenol in the composition can be varied as appropriate depending on other flavour characteristics required of the composition, as will be discussed below.  
      The weight ratio of cinnamic alcohol to eugenol may be at least 0.5:1, at least 0.75:1, at least 1:1, and possibly at least 1.5:1. The weight ratio of cinnamic alcohol to eugenol may be not more than 3:1, not more than 2.5:1, and possibly not more than 2:1. Appropriate ratios will again depend on other flavour characteristics required of the composition.  
      The eugenol may be present as eugenol itself and/or as an ingredient of essential oils and synthetic oils rich in eugenol (preferably containing at least 65% by weight of eugenol). Such oils include clove oils (which typically contain over 90% by weight of eugenol), cinnamon leaf oil, pimento oil etc.  
      For improved cinnamon flavour character, the composition preferably also includes capsicum and/or citrus oil, e.g. orange oil, lemon oil etc, with lime oil currently being favoured. Typically such optional additional materials are each present at a level of 1% by weight or less of the total weight of the composition, with suitable levels again depending on other desired flavour attributes of the composition.  
      For enhanced cinnamon flavour properties, it is also useful for the composition to include one or more of the following materials: benzyl formate, methyl cinnamate, benzoin, ethyl phenyl glycidate, ginger oil, cinnamyl acetate and methyl heptenone. Such materials improve the cinnamon flavour character, and are listed in order of preference. Again, such materials are typically present in an amount of 1% by weight or less of the total weight of composition or less, e.g. 0.5% by weight or less. In some cases, even very small amounts, e.g. 0.1% by weight or less, can have a signficant effect on the flavour properties of the composition.  
      The flavour composition typically also includes other flavour ingredients (which may be selected from the 400-500 or so flavour materials that are in current use when formulating flavour compositions) chosen to give desired overall flavour characteristics to the composition. It is unusual for an oral care flavour composition to have pure cinnamon flavour character, and more normally cinnamon character would be combined with one or more other flavour types, particularly aniseed, peppermint, menthol, spearmint, eucalyptus, wintergreen and/or clove.  
      The ingredients of the composition are known flavour materials which are readily available commercially in grades suitable for various intended purposes.  
      The flavour composition of the invention can be readily made by simply mixing the specified ingredients, as is well known to those skilled in the art.  
      The flavour compositions of the invention provide a useful alternative to cinnamic aldehyde and find application in a wide range of consumer products, particularly oral care products such as toothpastes, mouthwashes, breath sprays and breath freshening tablets. Also of interest are skin care products, e.g. clip care products such as lip balms, and chewing gums. The term “chewing gum” is intended also to encompass bubble gum.  
      Because the flavour compositions of the invention provide a cinnamon flavour without requiring the presence of cinnamic aldehyde, the undesirable sensitiser properties of cinnamic aldehyde can be avoided.  
      The present invention also includes within its scope consumer products, particularly oral care products, skin care products and chewing gums, including a flavour composition in accordance with the invention.  
      The consumer products may otherwise be of conventional composition and include the flavour composition in appropriate amount, as is well known to those skilled in the art. For example, a toothpaste formulation will typically include 0.5% to 1.5%, say about 1% by weight, of the flavour composition. A mouthwash will typically contain the flavour composition in an amount in the range 0.15% to 0.3% by weight. For a chewing gum, the composition of the invention may be present in an amount in the range 1.5% to 3% by weight. 
    
    
      The invention will be further illustrated by the following Examples of flavour compositions.  
      Table 1 give details of 10 flavour compositions, with all amounts being weight percent. Example A to G are flavour compositions in accordance with the present invention, while Example H to J are comparative examples outside the scope of the invention. The flavour type of each example was assessed by trained and skilled oral care flavourists and the flavour type characteristics are indicated on the table. In the Table, BPC stands for British Pharmacopoeia, and DQ stands for Dental Quality.  
      The compositions were prepared by mixing the listed ingredients, with solid materials first being charged to a tank followed by the liquid ingredients. The resulting mixture was then stirred until a homogeneous solution was achieved. The solid materials used are menthol, cyclotene, ethyl maltol and vanillin. Benzoin is best pre-dissolved in one of the liquid ingredients prior to addition to the flavour.  
      Table 2 gives details of the ingredients used in the flavour examples.  
                                   TABLE 1                                      Flavour                   Flavour       Example C       Flavour       Ingredient   Example A   Flavour   Menthol   Flavour   Example E       (all amounts wt %)   Peppermint   Example B   Peppermint   Example D   Spearmint       Flavour Type (as assessed   Wintergreen   Spearmint   Wintergreen   Menthol   Wintergreen       by oral care flavourists)   Cinnamon   Cinnamon   Cinnamon   Cinnamon   Cinnamon                                             ANETHOLE SYNTHETIC   9.4   10.5   13.5   9.5   10.5       ANISIC ALDEHYDE   0.2   0.2   0.2   0.2   0.2       BENZOIN Siam   0.03   0.05   0.02   0.1   0.03       BENZYL FORMATE   0.1   0.3   0.1   0.5   0.1       CAPSICUM OLEORESIN BPC   0.12   0.14       0.2   0.1       CARVONE DEXTRO   0.04   0.1   0.06   0.2   0.04       CINNAMIC ALCOHOL   2.9   7   2.2   11   9       CINNAMYL ACETATE   0.2   0.1   0.1   0.2   2.9       CLOVE oil terpeneless   2   4.5   0.5   8.9   5.9       CYCLOTENE   0   0.02   0   0.02   0       ETHYL MALTOL   0   0   0.06   0   0       ETHYL PHENYL GLYCIDATE   0.3   0.3   0.2   0.3   0.3       EUCALYPTOL   4   0   0.3   0   0       EUGENOL DQ   3.9   7   1.54   9   1       Lemon Spanish   0   0   0   0   0       LIME oil   0.2   0.52   0.2   0.7   0.2       MENTHOL LAEVO EXTRA   52.87   38   51   45   30       METHYL CINNAMATE   0.2   0.8   0.3   1   0.2       METHYL HEPTENONE PURE   0.02   0.04   0.02   0.04   0.02       METHYL SALICYLATE   15.2   1   14.8   3   31.51       Nutmeg   0   0   0   0   0       ORANGE CALIFORNIAN   0   0   0.5   0   0       PEPPERMINT American Yakima   4.5   5   6.38   3   1       Rectified       SPEARMINT American Far West   3.82   24.43   8.02   7.14   7       Native       Vanillin   0   0   0   0   0           100   100   100   100   100       Eugenol + 91.5% clove oil = ΣE   5.73   11.12   2:00   17.14   6.40       Cinnamic alcohol + ΣE   8.63   18.12   4.2   28.14   15.40       Cinnamic alcohol: ΣE   0.51:1   0.63:1   1.1:1   0.64:1   1.41:1                                                         Flavour   Flavour   Flavour                   Example H   Example I   Example J                   Peppermint   Peppermint   Peppermint       Ingredient           Wintergreen   Wintergreen   Wintergreen       (all amounts wt %)   Flavour   Flavour   (Not enough   Clove   Floral       Flavour Type (as assessed   Example F   Example G   alcohol and   (Too much   (Too much       by oral care flavourists)   Cola   Cinnamon   eugenol)   eugenol)   alcohol)                                             ANETHOLE SYNTHETIC   5   12   9.4   9.4   9.4       ANISIC ALDEHYDE   0       0.2   0.2   0       BENZOIN Siam   0.05   0.2   0.03   0   0       BENZYL FORMATE   0.2   1   0.1   0   0       CAPSICUM OLEORESIN BPC   0.1   0.2   0.12   0.12   0       CARVONE DEXTRO   0.1   0.4   0.04   0.04   0.04       CINNAMIC ALCOHOL   6   22   1   0.3   7       CiNNAMYL ACETATE   0.1   0.4   0.2   0   0.3       CLOVE oil terpeneless   3.5   18   0   5   0       CYCLOTENE   0   0.04   0   0   0       ETHYL MALTOL   0   0   0   0   0       ETHYL PHENYL GLYCIDATE   0.1   0.3   0.3   0   0.3       EUCALYPTOL   0   0   4   4   4       EUGENOL DQ   1.5   12   0.5   3   0.5       Lemon Spanish   26.6   0   0   0   0       LIME oil   18   1.5   0.2   0   0.2       MENTHOL LAEVO EXTRA   10   10   52.87   51.94   48       METHYL CINNAMATE   0.3   1   0.2   0   0.2       METHYL HEPTENONE PURE   0   0.04   0.02   0   0.02       METHYL SALICYLATE   1   3   15.8   14   15.02       Nutmeg   1   0   0   0   0       ORANGE CALIFORNIAN   18   0   0   0   0       PEPPERMINT American Yakima   0   3   10   9   10       Rectified       SPEARMINT American Far West   8.15   14.92   5.02   3   5.02       Native       Vanillin   0.3   0   0   0   0           100   100   100   100   100       Eugenol + 91.5% clove oil = ΣE   4.70   28.47   0.5   7.58   0.5       Cinnamic alcohol + ΣE   10.70   50.47   1.5   7.87   7.5       Cinnamic alcohol: ΣE   1.28:1   0.77:1   2:1   0.04:1   14:01                  
 
     
       
         
           
               
               
               
               
               
             
               
                 TABLE 2 
               
               
                   
               
               
                   
               
               
                 Ingredient 
                 Chemical Name 
                 CAS Number 
                 FEMA GRAS 
                 Supplier 
               
               
                   
               
             
            
               
                 ANETHOLE SYNTHETIC (Trans) 
                 p-Methoxy Propenyl Benzene 
                 4180-23-8 
                 2086 
                 Millenium 
               
               
                 ANISIC ALDEHYDE 
                 p-Methoxybenzaldehyde 
                 123-11-5 
                 2670 
                 R. C Treat &amp;Co LTD 
               
               
                 BENZOIN Siam 
                 n/a 
                 9000-72-0 
                 2133 
                 Kelly 
               
               
                 BENZYL FORMATE 
                 BENZYL FORMATE 
                 104-57-4 
                 2145 
                 Haarmann &amp; Reimer 
               
               
                 CAPSICUM OLEORESIN BPC 
                 n/a 
                 8023-77-6 
                 2234 
                 Lionel Hitchin (Essential 
               
               
                   
                   
                   
                   
                 Oils) Ltd 
               
               
                 CARVONE DEXTRO 
                 d--1-methyl-4isopropenyl-6- 
                 2244-16-8 
                 2249 
                 H Reynaud et Fils 
               
               
                   
                 cyclohexen-2-one 
               
               
                 CINNAMC ALCOHOL 
                 trans-3-Phenyl-2-propen-ol 
                 104-54-1 
                 2294 
                 Haarmann &amp; Reimer 
               
               
                 CINNAMYL ACETATE 
                 3-phenyl-2-propenyl acetate 
                 21040-45-9 
                 2293 
                 Haarmann &amp; Reimer 
               
               
                 CLOVE oil terpeneless 
                 n/a (90.5-92.5% eugenol) 
                 8000-34-8 
                 2323 
                 Fragrance Materials 
               
               
                 CYCLOTENE 
                 Methylcyclopentenolone 
                 80-71-1 
                 2700 
                 R. C Treat &amp; Co Ltd 
               
               
                 ETHYL MALTOL 
                 3-Hydroxy-2-ethyl-4-pyrone 
                 4940-11.8 
                 3487 
                 Pfizer 
               
               
                 ETHYL PHENYL GLYCIDATE 
                 Ethyl-3-phenyl-2,3-epoxypropionate 
                 121-39-1 
                 2454 
                 IFF 
               
               
                 EUCALYPTOL (1,8-cineole) 
                 1,8 Epoxy-para-menthane 
                 470-82-6 
                 2465 
                 AMC Chemicals 
               
               
                 EUGENOL DQ 
                 2-methoxy-4-(2-propenyl)phenol 
                 97-53-0 
                 2467 
                 Charabot 
               
               
                 Lemon Spanish 
                 n/a 
                 84929-31-7 
                 2625 
                 IFF 
               
               
                 LIME oil 
                 n/a 
                 8008-26-2 
                 2631 
                 Copeland 
               
               
                 MENTHOL LAEVO 
                 l-5-Methyl-2- 
                 2216-51-5 
                 2665 
                 Helm 
               
               
                   
                 (1-methylethyl)cyclohexanol 
               
               
                 METHYL CINNAMATE 
                 Methyl-3-Phenyl-2-propenylate 
                 103-26-4 
                 2698 
                 Haarmann &amp; Reimer 
               
               
                 METHYL HEPTENONE PURE 
                 6-Methyl-5-hepten-2-one 
                 110-93-0 
                 2707 
                 BASF 
               
               
                 METHYL SALICYLATE 
                 2-Hydroxy methylbenzoate 
                 119-36-8 
                 2745 
                 Rhodia 
               
               
                 Nutmeg 
                 n/a 
                 8008-45-5 
                 2793 
                 IFF 
               
               
                 ORANGE CALIFORNIAN 
                 n/a 
                 8008-57-9 
                 2825 
                 Charobot 
               
               
                 PEPPERMINT American 
                 n/a 
                 8006-90-4 
                 2848 
                 Essex Labs Essential 
               
               
                 Yakima Rectified 
                   
                   
                   
                 Oils &amp; Extracts 
               
               
                 SPEARMINT American Far 
                 n/a 
                 8008-79-5 
                 3032 
                 Essex Labs Essential 
               
               
                 West Native 
                   
                   
                   
                 Oils &amp; Extracts 
               
               
                 Vanillin 
                 4-Hydroxy-3-methoxy benzaldehyde 
                 121-33-5 
                 3107 
                 Rhodia