WO2004073669A1

WO2004073669A1 - Flavour compositions comprising menthol, a mint oil and other flavour materials

Info

Publication number: WO2004073669A1
Application number: PCT/GB2004/000508
Authority: WO
Inventors: Keith Douglas Perring; Kathleen Mary Tuck; David Anthony Mcnulty; Mattt Wilson
Original assignee: Quest International Services B.V.
Priority date: 2003-02-18
Filing date: 2004-02-11
Publication date: 2004-09-02
Also published as: GB2415596A; GB2415596B8; GB2415596B; GB0516683D0; GB2415596A8

Abstract

A flavour composition comprises: (a) at least 10% by weight of the total weight of the flavour composition of menthol; (b) at least 10 % by weight of the total weight of the flavour composition of a mint oil selected from peppermint oil, spearmint oil, and mixtures thereof; the menthol and one or more mint oils together comprising at least 40 % by weight of the total weight of the composition; and (c) at least 3 % by weight of the total weight of the flavour composition of at least two flavour materials having an octanol-water partition coefficient of at least 4.0 (in logarithmic form); wherein the flavour composition has a weighted average octanol-water partition coefficient of at least 3.3 (in logarithmic form). The composition shows enhanced substantivity and thus longevity in the oral cavity and finds use in consumer products, particularly oral care products.

Description

FLAVOUR COMPOSITIONS COMPRISING MENTHOL , A MINT OIL AND OTHER FLAVOUR MATERIALS

Field of the Invention

The present invention relates to flavour compositions and to consumer products, particularly oral care products such as toothpastes and mouthwashes, including the flavour compositions.

Background to the Invention

Flavour materials may be incorporated in consumer products such as oral care products, e.g. toothpaste, mouthwash and chewing gum, amongst others, to cover the taste of base ingredients and to impart a signal to a consumer that the product may deliver freshness and cleanliness upon use. If a product has a fresh taste and smell, then these are key indicators to consumers that their teeth, mouth and breath will be clean with use.

Many flavour types are known and may be exploited in the oral care area, but flavour compositions which include mint oils, e.g. peppermint and spearmint oils, are particularly popular in oral care products. Mint oils are typically used to impart a connotation of freshness as they naturally contain menthol which has physiological coolant properties. Often this impression of freshness is enhanced by the inclusion of additional menthol (see, for example, S Arctander, 'Terfume and Flavour Materials of Natural Origin", Elizabeth, N.J., USA, 1960).

Most of the flavour materials present in a toothpaste or mouthwash are spat from the mouth, whilst those used in confectioneries and foodstuffs are swallowed. Hence, materials providing freshness cues in oral care products tend to have only a fleeting effect. The longevity of the flavour imparted by an oral care product tends to be quite limited, e.g. for many products such as toothpaste and mouthwash, often less than ten or twenty minutes.

It is therefore an objective of product formulators in this area to provide flavour compositions with enhanced substantivity and thus longevity in the oral cavity, and which deliver a more enduring freshness following use.

Flavour compositions that are substantive in the oral cavity have the potential to reduce or mask breath malodour. Moreover, the more substantive the flavour composition, the greater the potential for long term malodour counteractancy. The term "substantivity" as used herein is the ability of a flavour material or flavour composition to attach to a surface, e.g. oral mucosa, and to resist being washed or rinsed away, or evaporated.

There are many approaches disclosed in the prior art for enhancing the longevity of fragrance and flavour materials.

One approach is to encapsulate a flavour composition in capsules which, in-use, release the encapsulated flavour to the oral mucosa and/or surface of the tongue over time. For example, US 4597959 describes sustained release in the mouth from a wafer comprising a flavour composition microencapsulated in gelatin/carrageenan. The flavour may be incorporated within discrete capsules or via inclusion in a carrier matrix comprising a variety of materials such as polymers or cyclodextrins.

Another approach aimed at increasing the time that flavour materials are retained in the mouth is to incorporate so called 'pro-ingredients' in oral care products. These generally comprise a derivative of a flavour that is more stable than the flavour itself e.g. being less volatile, being chemically protected from taking part in undesired reactions etc., and from which the flavour can be released, e.g. in response to water. See, for example, US 4206301 which discloses polymer backbones having pendant flavour groups that are releasable upon hydrolysis and WO 95/07683 which describes phosphate derivatives that may be used orally or topically to deliver flavorants.

Yet another approach for increasing organoleptic longevity is disclosed in a number of documents including WO 96/12468, WO 97/30689 and US 5780404. These concern so called "enduring perfume" compositions based upon the inclusion of materials characterised by high boiling points (at least 250 °C) and high octanol/water partition coefficients (at least 3, expressed as the common logarithm). The term "enduring perfume" is used in the documents to refer to perfumes which provide a long lasting aesthetic effect with a minimum amount of material when applied to fabric or body surfaces such as skin or hair. Thus, for example, in WO 96/12468, d-limonene, 1-carvone and linalyl acetate are categorised as non-enduring perfume ingredients, whereas caryophyllene, amyl cinnamic aldehyde and benzophenone are categorised as enduring ingredients.

The present invention is, however, based on the appreciation that for the oral cavity the longevity of flavour retention is surprisingly not dependent upon the boiling point (and the related property of volatility) of a particular flavour material. The present invention therefore seeks to provide an alternative approach for the formulation of improved flavour compositions that deliver longer-lasting flavour effects in the oral cavity following use.

Summary of the Invention

In one aspect, the present invention provides a flavour composition comprising:

(a) at least 10% by weight of the total weight of the flavour composition of menthol;

(b) at least 10% by weight of the total weight of the flavour composition of a mint oil selected from peppermint oil, spearmint oil, and mixtures thereof; the menthol and one or more mint oils together comprising at least 40% by weight of the total weight of the composition; and (c) . at least 3 % by weight of the total weight of the flavour composition of at least two flavour materials having an octanol-water partition coefficient of at least 4.0 (in logarithmic form); wherein the flavour composition has a weighted average octanol-water partition coefficient of at least 3.3 (in logarithmic form).

It has been found by the present inventors that the above defined flavour compositions are effectively retained in the oral cavity on use for longer lasting flavour benefit, typically of at least 20 minutes or even 30 minutes, after contact with the oral cavity.

The octanol-water partition coefficient (P) of a material i.e. the ratio of a material's equilibrium concentration in octanol and water, is well known in the literature as a measure of hydrophobicity and water solubility (see Hansch and Leo, Chemical Reviews, 526 to 616, (1971), 71; Hansch, Quinlan and Lawrence, J. Organic Chemistry, 347 to 350 (1968), 33). High partition coefficient values are more conveniently given in the form of their logarithm to the base 10, logP. While logP values can be measured experimentally i.e. directly, and measured logP data is available for many flavours, logP values are most conveniently calculated or approximately estimated using mathematical algorithms. There are several recognised calculation or estimation methods available commercially and/or described in the literature (see for example A Leo, Chem.Rev 93(4), 1281-1306, (1993), "Calculating logP oct from structures"). Generally these models correlate highly but may for specific materials produce logP values which differ in absolute terms (by up to 0.5 log units or even more). However, no one model is universally accepted as the most accurate across all compounds. This is particularly true for estimates on materials of high logP (say 4 or greater). In the present specification, logP values are obtained using the estimation software commercially available as 'LogP' from Toronto-based Advanced Chemistry Development Inc (ACD) which is well-known to the scientific community, and accepted as providing high-quality predictions of logP values. References to logP values thus mean values obtained using the ACD software. In the case of a flavour composition which is a mixture of flavour materials, the octanol- water partition coefficient is calculated as a weighted average based on the percentages by weight of different components in the mixture. For example, for a mixture of a% by weight of flavour material A with a logP value of logP_a and b% by weight of flavour material B with a logP value of logP_b where a+b = 100% , then the weighted average logP of the mixture is: -

(α x logP_α )+ (b χ logP_&)

100

Therefore, the weighted average octanol-water partition coefficient (logP) can be determined from Equation (1) below

Equation (1)

Weighted average logP =

100

where W; = weight percentage of flavour material logP = logarithm (base 10) of the octanol-water partition coefficient of flavour material

When calculating the weighted average logP of a flavour composition, solvents and other vehicles, which have low, or no odour or taste, are excluded. Thus, for example, the calculation of the weighted average logP of a flavour composition is carried out by ignoring solvents such as propylene glycol, benzyl alcohol, triacetin, isopropyl myristate and isopropyl alcohol.

Flavour compositions with a weighted average logP of at least 3.3 typically provide an increase in the retention of flavour in vivo when delivered to the oral cavity, e.g. from an oral care product. Flavour compositions of the invention preferably have a weighted average logP value of at least 3.4, and more preferably of at least 3.5. The mint oil, particularly peppermint oil and/or spearmint oil, is typically of natural or synthetic origin, preferably of natural origin.

Peppermint oils typically have logP values in the range 2.9 to 3.2.

Suitable peppermint oils for use herein include, for example, Peppermint American Far West, Peppermint Chinese Terpeneless, Peppermint American Mid West.

Spearmint oils typically have logP values in the range 2.5 to 3.0.

A suitable spearmint oil for use herein includes, for example, Spearmint American Far West.

Several materials may be present as an ingredient of the mint oils, peppermint and/or spearmint. For example, carvone laevo is the principal component of spearmint oil, but also present is a number of minor components such as carveol. The materials commonly found in mint oils, particularly of natural origin, are indicated in Table 1 which also gives the octanol-water partition coefficient of each material expressed as the common logarithm to base 10:

Table 1

Ingredient logP Mint oil found in

Carvone laevo 2.27 Spearmint oil Caryophyllene 6.62 Peppermint and spearmint oils Eucalyptol 3.22 Peppermint and spe-umint oils Limonene laevo 4.46 Peppermint and spearmint oils Menthol laevo 3.20 Peppermint oil Menthone 2.63 Peppermint and spearmint oils Menthyl acetate 4.10 Peppermint oil Pinene Alpha 4.46 Peppermint and spearmint oils

Pinene Beta 4.37 Peppermint and spearmint oils

Any one of these materials may be present itself in a mint-based flavour and/or as an ingredient of a natural or synthetic mint oil.

Menthol may be present as menthol itself and/or as an ingredient of a peppermint oil.

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. Particularly useful flavour materials which may present in a flavour composition of the invention include the following:

Ingredient logP

Alcohol CIO (decanol) 4.06

Anethole 3.17

Eugenol 2.79

Hexyl Cinnamic Aldehyde 4.67

Ionone beta 3.91

Methyl salicylate 2.40

Terpinyl propionate 4.20

For improved substantivity properties, a flavour composition of the invention preferably includes less than 10% by weight of flavour materials which readily hydrolyse in the mouth. Such materials tend to have short half-lives under these conditions. One category of hydroly sable flavour materials are esters, particularly esters prepared from primary alcohols (primary esters). Esters based on many secondary alcohols (secondary esters) also tend to undergo rapid hydrolysis in the oral cavity. Exceptions to this are the secondary esters fenchyl acetate and isobornyl acetate which are sterically protected from hydrolysis by the carbon atoms of their bicyclo [2.2.1] heptane skeleton. These materials are therefore more enduring.

Thus, in a preferred embodiment, the invention provides a flavour composition comprising:

(b) at least 10% by weight of the total weight of the flavour composition of a mint oil selected from peppermint oil, spearmint oil, and mixtures thereof; the menthol and one or more mint oils together comprising at least 40% by weight of the total weight of the composition; and

(c) at least 3 % by weight of the total weight of the flavour composition of at least two flavour materials having an octanol-water partition coefficient of at least 4.0 (in logarithmic form); wherein the flavour composition has a weighted average octanol-water partition coefficient of at least 3.3 (in logarithmic form), and includes less than 10% by weight of the total weight of the flavour composition of esters which are capable of readily hydrolysing when brought into contact with the oral cavity.

When calculating the relative amount of hydrolysable esters present in a flavour composition it is necessary to account for not only the esters themselves i.e. added individually to the composition, but also esters present as ingredients of essential oils, e.g. menthyl acetate from peppermint oil. Although menthyl acetate has an octanol-water partition coefficient of 4.1, its residence time in the mouth is surprisingly limited by its tendency to rapidly hydrolyse in vivo (as described below in Example 2).

Esters prepared from tertiary alcohols (tertiary esters), generally with logP values of at least 3.3, may have long half-lives in the mouth. Optionally therefore, flavour materials which are tertiary esters may also be included in a flavour composition of the invention to enhance flavour perception. Preferably, a flavour composition comprises at least 0.1 % by weight of the total weight of the flavour composition of at least one tertiary ester, more preferably at least 0.3 % by weight. Suitable tertiary esters include linalyl acetate, dimethyl benzyl carbinyl butyrate, linalyl isobutyrate and terpinyl propionate.

Flavour compositions of the invention not only demonstrate improved substantivity, but may also be effective at reducing oral malodour. For oral malodour reducing properties, the composition preferably also includes at least 0.5% by weight of the total weight of the flavour composition, more preferably at least 1.0% by weight, and even more preferably at least 3.0% by weight, of at least one material selected from decanol (alcohol CIO), alpha ionone, alpha pinene, and mixtures thereof.

Thus, in an even further aspect there is provided a flavour composition comprising:

(a) at least 10 % by weight of the total weight of the flavour composition of menthol;

(b) at least 10% by weight of the total weight of the flavour composition of a mint oil selected from peppermint oil, spearmint oil, and mixtures thereof; the menthol and one or more mint oils together comprising at least 40% by weight of the total weight of the composition;

(c) at least 3 % by weight of the total weight of the flavour composition of at least two flavour materials having an octanol-water partition coefficient of at least 4.0 (in logarithmic form); and

(d) at least 0.5% by weight of the total weight of the flavour composition of at least one material selected from decanol, alpha ionone, alpha pinene, and mixtures thereof; wherein the flavour composition has a weighted average octanol-water partition coefficient of at least 3.3 (in logarithmic form).

The ingredients of the composition are known flavour materials which are readily available commercially in grades suitable for various intended purposes.

A flavour composition of the invention can be readily made by simply mixing the specific ingredients, as is well known to those skilled in the art. The flavour compositions of the invention find application in a wide range of consumer products which may be edible or potable, particularly oral care products such as toothpastes which may be clear or opaque (in paste, cream, gel and other solid forms etc.), mouthwashes, chewing gum (where the term "chewing gum" is intended also to encompass bubble gum), dental floss, dissolvable mouth films, breath sprays and breath freshening tablets.

The present invention also includes within its scope consumer products, particularly oral care products, comprising a flavour composition in accordance with the invention.

The consumer products, particularly oral care products, which include a flavour composition in accordance with the invention may be formulated in a conventional manner as is well known to those skilled in the art. Typically, a flavour composition of the invention may be present in a product in the range from 0.1 % by weight to about 10% by weight, preferably in the range from 0.2% by weight to about 5.0% by weight and more preferably from 0.3 % by weight to about 3.0% by weight.

The invention is described, by way of illustration, in the following Examples and with reference to the accompanying drawings in which:

Figure 1 shows the results of an in vivo mouthspace analysis for 1-limonene and is an MS-Nose spectrum which is a plot of the concentration of limonene in vivo in the mouth (arbitrary units) measured by MS-Nose against time (minutes) after brushing with a toothpaste including 1-limonene;

Figure 2 shows the results of an in vivo mouthspace analysis for 1-carvone and is an MS-Nose spectrum which is a plot of the concentration of carvone in vivo in the mouth (arbitrary units) measured by MS-Nose against time (minutes) after brushing with a toothpaste including 1-carvone; and

Figure 3 is a graph of mouthspace composition (percent) against time (minutes) after brushing and shows the rate of hydrolysis of menthyl acetate (represented by an empty square) to the corresponding alcohol (represented by a filled in diamond) in the mouth after brushing with a menthyl acetate-containing toothpaste.

Figure 4 is a bar chart of the headspace (HS) concentration of alcohol hydrolysis product (percent) determined according to the following formula: headspace concentration (%) = headspace gc area of alcohol/

(headspace gc area of alcohol + headspace gc area of ester) against esters, showing the results of the relative amounts of alcohol formation after five minutes from the esters: geranyl propionate (represented by a diagonal hatched bar), menthyl acetate (represented by a dotted bar), fenchyl acetate (represented by a shaded bar) and linalyl acetate (represented by a vertical hatched bar).

Example 1

The longevity of flavour materials in the mouth may conveniently be studied using a realtime headspace analyser such as the MS-Nose (ex Micromass UK Ltd). This instrument comprises MS equipment coupled to an atmospheric pressure sampler, which makes it possible to easily sample and quantify the composition of the headspace (that is 'mouthspace') periodically, e.g. every minute or half-minute, following use of an oral care product which includes a flavour composition or flavour material.

Example 1(a)

The two major components of spearmint oil 1-limonene and 1-carvone, were separately incorporated in a translucent silica toothpaste base of the following composition at 0.1% w/w, 0.25% w/w or 0.5% w/w:

Toothpaste base

w/w%

Silica 16%

Sorbitol (70% syrup) 63% Sodium lauryl sulphate 2.0%

Sodium 0.8% monofluorophosphate

Saccharin 0.2%

Flavour material 0.1-0.5%

Deionised water to 100%

Typically, a toothpaste base including 0.25% w/w of 1-limonene or 1-carvone was found to be the most convenient for these studies.

A study participant was required to brush all tooth surfaces (but not the tongue area) for one minute with a toothpaste base. After this time, the toothpaste was spat out and the mouth rinsed once with fresh water. The MS-Nose run was then started and the first measurement of the participant's breath taken after 30 seconds. Subsequent breath measurements were taken and analysed at one minute intervals. In between MS-Nose breaths the participant's mouth was kept closed and normal breathing was carried out through the nose. Measurements were taken for as long as possible, up to a maximum of , one hour.

MS-Nose Settings

Ion Optics: Analyser:

Capillary 3.00 LM Resolution 15

Cone 20 HM Resolution 15

Extractor 5 Ion Energy 1.0

RF Lens 0.2 Multiplier 650

Source Block Temp 80

Desolvation Temp 80

Pressures and Temperatures: Transfer Line Temperature 100 Analyser Vacuum 4.3 e^"5

Desolvation Gas Flow 504

Figures 1 and 2 show the variation in mouthspace concentration of 1-limonene and 1- carvone, following brushing with a toothpaste, from which it can be seen that the mouthspace concentration of 1-limonene decreases at a much slower rate than that of 1- carvone.

Limonene is a highly volatile terpene hydrocarbon (possessing a saturated vapour pressure at 25 °C of approximately 1500 micron Hg) which is generally known in many consumer products to be fleeting and non-enduring. The finding that it is retained in the oral cavity for a considerable period of time was therefore surprising. Further data has been acquired which suggests that this feature arises, at least in part, from a lower clearance rate (i.e. a slower rate of decline in the mouthspace concentration) for high logP ingredients.

Example Kb)

The half-lives of a number of flavour materials in the oral cavity, following brushing with a toothpaste which included one of the flavour materials, was determined according to the following method.

The flavour materials tested were as follows: Anethole Carvone dextro Dodecalactone gamma Hexyl cinnamic aldehyde Hexanol Limonene The materials were separately incorporated in a toothpaste base of Example 1(a) at 0.1 % w/w, 0.25% w/w and 0.5% w/w. As in Example 1(a), typically, a toothpaste including 0.25% w/w of a flavour material was found to be the most convenient for use. The study was then carried out according to the procedure described in Example 1(a).

Simple first order kinetics may be applied over the first 30 minutes of data collected by the MS-Nose to calculate half-lives for comparison purposes. The half-lives obtained in this way for the flavour materials tested are shown in Table 2 below.

Table 2 Flavour material mouthspace half-lives (following toothpaste application)

These results show that there is strong correlation between the half-life of a material and its polarity, as described by log P: materials with high log P (and therefore low water solubility) have longer half-lives.

Example 2

The stability of flavour materials which are primary, secondary or tertiary esters, was tested in vivo in the mouth using conventional gas chromatographic techniques.

The esters tested were as follows: Geranyl propionate (primary ester) Menthyl acetate (secondary ester) Fenchyl acetate (secondary ester) Linalyl acetate (tertiary ester)

The primary, secondary or tertiary esters to be tested were each incorporated in separate toothpaste bases of formulation described in Example 1(a). A subject then brushed his teeth with one of the toothpastes for 1 minute and was allowed one rinse with fresh water following spitting. The subject then delivered five breaths into a ThermoQuest thermal desorption tube, packed with Tenax TA60-80 mesh (from Chrompack), at various time intervals after brushing, e.g. 1 minute, 3 minutes, 5 minutes, 8 minutes, 12 minutes, 16 minutes, 20 minutes and 30 minutes. Thermal desorption-GC was then carried out to analyse the composition of the breath at each time interval. Thermal desorption conditions were as follows:

Machine: Trace 2000 series GC fitted with a programmable temperature vaporiser (PTV) Column flow : 1.6ml/min nitrogen

Split flow: 2.0nύ/min

PTV temperature programme: 50°C to 250°C, heated at 14.5°C/min

The results for a toothpaste containing menthyl acetate are presented in Figure 3.

Figure 3 shows a graph of the percentage mouthspace composition against time (minutes) of the ester menthyl acetate and its alcohol hydrolysis product, following brushing with a menthyl acetate-containing toothpaste. Menthyl acetate has a logP of 4.10. However, it is clear from the results obtained that the material does not survive long in the mouth. It is thought that the ester may undergo enzymatic hydrolysis to yield menthol (which itself is short-lived in the mouth). Figure 4 shows the concentration of alcohol hydrolysis products formed after five minutes from the esters geranyl propionate (1°), menthyl acetate (2°), fenchyl acetate (2°) and linalyl acetate (3°). As will be appreciated from this figure, tertiary esters were found to hydrolyse relatively slowly whereas the primary ester was rapidly hydrolysed. Secondary esters were intermediate in behaviour although it was clear that certain sterically hindered secondary esters such as fenchyl acetate were more stable than anticipated.

Example 3

The ensuing flavour composition in accordance with the invention has a fruity minty flavour, and was prepared by mixing the following ingredients:

Ingredient % logP

Aldehyde C12 (dodecanal) 0.01 5.16

Amyl Cinnamic Aldehyde 0.10 4.56

Anethole synthetic 10.00 3.17

Benzoin Absolute 50% PG 1.00 2.13

Cyclopentadecanolide 1 % PG 0.20 5.44

Lemon Spanish 5.00 4.46

Linalyl Acetate 2.00 4.12

Linalyl Isobutyrate 5.00 5.00

Menthol laevo 30.00 3.20

Myrcene 3.69 4.46

Orange Californian 5.00 4.46

Peppermint American Far West 18.00 3.11

Peppermint Chinese Terpeneless 20.00 3.11

Weighted average logP = ∑W_i(logP_i)/100= 3.48

The flavour composition was incorporated in a silica toothpaste of formulation described in Example 1(a) above, and the flavour longevity measured olfactively by a person skilled in the art who noted the residual flavour intensity in the month during a 20 minute period after brushing their teeth with the toothpaste. The flavour composition was found to have a flavour longevity extending to 20 minutes in vivo from the silica toothpaste.

Example 4

The ensuing flavour composition in accordance with the invention is a substantive version of a classic peppermint flavour, which was prepared by mixing the following ingredients:

Ingredient % logP

Alcohol CIO 0.05 4.06

Aldehyde Cll (undecylenic) 0.01 4.12

Aldehyde C12 0.01 5.16

Amyl Cinnamic Aldehyde 0.24 4.56

Anefhole 7.50 . 3.17

Caryophyllene 2.36 6.62

Damascone Alpha 0.24 4.00

Damascone Beta 0.24 3.60

Dihydroanefhole 2.36 3.73

Dimethyl Benzyl Carbinyl Butyrate 0.04 4.06

Dodecalactone Gamma 0.47 3.45

Fenchyl Acetate 1.41 3.90

Hexyl Cinnamic Aldehyde 0.47 4.67

Ionone Beta 0.01 3.91

Isobornyl Acetate 1.37 3.89

Limonene Dextro 4.72 4.46

Linalyl Acetate 1.42 3.75

Linalyl Isobutyrate 2.36 5.00

Menthol Laevo Extra 26.25 3.20

Methyl Ionone Alpha Iso 0.01 4.32

Ocimene 1.89 3.67 Para Cymene 0.94 4.02

Peppermint American Far West 11.25 3.11

Peppermint American Mid West 11.25 3.11

Peppermint Chinese Terpeneless 15.00 3.11

Pinene Alpha 0.94 4.46

Pinene Beta 1.89 4.37

Spearmint American Far West 3.75 2.70

Terpinene Gamma 1.42 4.46

Tetrahydrogeraniol 0.13 3.55

Weighted average logP = ∑W_i(logP_i)/100 = 3.45

Example 5

The following flavour compositions (A-E) in accordance with the invention are all mint flavours and all comprise base flavour composition F. Flavour composition G is a comparative example outside the scope of the invention.

Base Flavour Composition F

Ingredient % lo P

Alcohol CIO (decanol) 0.19 4.06

Aldehyde Cll (undecylenic) 0.02 4.11

Aldehyde C12 (dodecanal) 0.02 5.16

Caryophyllene 9.43 6.78

Hexyl Cinnamic Aldehyde 1.89 5.33

Isobornyl Acetate 5.66 3.60

Amyl Cinnamic Aldehyde 0.94 4.56

Damascone Alpha 0.94 3.95

Damascone Beta 0.94 4.40

Dihydroanethole 9.43 3.66

Dimethyl Benzyl Carbinyl Butyrate 0.15 4.06

Dodecalactone Gamma 1.89 3.45

Fenchyl Acetate 5.66 3.90

Ionone Beta 0.02 3.85

Limonene Dextro 18.88 4.46

Linalyl Acetate 5.66 4.12

Linalyl Isobutyrate 9.43 5.00

Methyl Ionone (Alpha Iso) 0.02 4.41

Ocimene 7.55 3.67

Para Cymene 3.77 4.02

Pinene Alpha 3.77 4.37

Pinene Beta 7.55 4.37

Terpinene Gamma 5.66 4.36

Tetrahydrogeraniol 0.53 3.70

Weighted average logP ∑W,(logP,)/100 = 4.44 The flavour longevity of compositions A to G was determined using the method described in Example 3 above.

It is clear from the foregoing that there is a correlation between logP of a flavour material and the longevity of the material in the oral cavity. Therefore, where the weighted average logP of a flavour composition is sufficiently high, such a composition will be substantive in-use to deliver a long-lived flavour effect in the mouth.

Claims

1. A flavour composition comprising:

(c) at least 3 % by weight of the total weight of the flavour composition of at least two flavour materials having an octanol-water partition coefficient of at least 4.0 (in logarithmic form); wherein the flavour composition has a weighted average octanol-water partition coefficient of at least 3.3 (in logarithmic form).

2. A flavour composition according to claim 1, wherein the composition has a weighted average octanol-water partition coefficient of at least 3. 4.

3. A flavour comparison according to claim 1 or 2, wherein the composition has a weighted average octanol-water partition coefficient of at least 3.5.

4. A flavour composition according to any one of the preceding claims, wherein the mint oil is of natural origin.

5. A flavour composition according to any one of the preceding claims, wherein the composition also includes less than 10% by weight of the total weight of the flavour composition of esters which are capable of readily hydrolysing when brought into contact with the oral cavity.

6. A flavour composition according to any one of the preceding claims, wherein the composition also comprises at least 0.1 % by weight of the total weight of the flavour composition of at least one tertiary ester.

7. A flavour composition according to any one of the preceding claims, wherein the composition also comprises at least 0.5% by weight of the total weight of the flavour composition of at least one material selected from decanol, alpha ionone, alpha pinene, and rruxtures thereof.

8. A consumer product comprising a flavour composition according to any one of the preceding claims.

9. A consumer product according to claim 8, wherein the product is an oral care product.