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(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT)

(19) World Intellectual Property Organization International Bureau

(43) International Publication Date (10) International Publication Number 28 May 2009 (28.05.2009) PCT WO 2009/065239 Al

(51) International Patent Classification: (74) Agent: SIMMONS, John, Murray; Ueberlandstrasse A23L 1/221 (2006.01) C12G 3/06 (2006.01) 138, CH-8600 Duebendorf (CH). (81) Designated States (unless otherwise indicated, for every (21) International Application Number: kind of national protection available): AE, AG, AL, AM, PCT/CH2008/000481 AO, AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, (22) International Filing Date: EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, , ID, 17 November 2008 (17.1 1.2008) IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, (25) Filing Language: English MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY,TJ, (26) Publication Language: English TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 60/988,867 19 November 2007 (19.1 1.2007) US kind of regional protection available): ARIPO (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, (71) Applicant (for all designated States except US): GIVAU- ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), DAN SA [CWCH]; Chemin de Ia Parfumerie 5, CH-1214 European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, Vernier (CH). FR, GB, GR, HR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, NO, PL, PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, (72) Inventors; and CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (75) Inventors/Applicants (for US only): YANG, Xiaogen Published: [US/US]; 7507 Secret Creek Court, West Chester, Ohio — with international search report 45069 (US). , Zhonghua [CN/US]; 8929 Roan Ln, — before the expiration of the time limit for amending the Cincinnati, Ohio 45242 (US). JORDAN, Jason [US/US]; claims and to be republished in the event of receipt of 2145 Knightsbridge Drive, Cincinnati, Ohio 45244 (US). amendments

(54) Title: COMPOSITIONS AND THEIR USE

(57) Abstract: Provided are compositions comprising alcohol taste enhancing ingredients for use in alcoholic beverages, and taste- enhanced alcoholic beverages comprising said ingredients. The alcohol enhancers are polygodial, and warburganal, or extracts c n prising these compounds, which when combined with alcohol () enhance its intensity and mimic its duration and onset. COMPOSITIONS AND THEIR USE

TECHNICAL FIELD

Provided are compositions comprising flavour enhancing compounds for use in food products or products placed in the oral cavity, and flavour-enhanced food products comprising said compounds or compositions.

BACKGROUND

It is of interest in the food industry to enhance desired flavour sensations, in particular the taste/warming sensation associated with alcohol (ethanol).

Compounds that can enhance the taste of alcohol are of great interest and may allow not only to enhance the alcohol taste but also to reach a certain taste intensity at a reduced concentration of alcohol (ethanol). For example, without limitation, in alcoholic beverages that have a low ethanol concentration but still provide the same or very similar taste as their non- reduced counterparts.

Polygodial and warburganal are known for their antifungal and insect antifeedant properties and their pungent taste. Polygodial is known to improve mint flavors and reduce the bitter off- taste of artificial sweeteners. US 5,523,105 discloses the use of polygodial to enhance the coolness and suppress the bitter and offensive taste of mint. US5,948,460 discloses the use of polygodial in diet beverages to reduce the aftertaste of artificial sweeteners and enhance their sweetness. WO 2006109241 discloses flavour and skin sensation compositions that may be added to various products including, among others, alcoholic , said flavour compositions comprising a hot component, a cooling component, and a bitter component, wherein the hot component includes, among others, polygodial, and the cooling or minty component is selected from the group consisting of menthol, menthyl succinate, menthyl lactate, p-menthane-3,8-diol, 8-p-menthen-3-ol, 3-(3'-P-menthanyloxy)-l,2-propanediol, menthone glycerol ketal, 2-(l-methyl propyl)-l-cyclohexanone, N-ethyl-3-P- menthanecarboxamide, aspartic acid, N-(4-hydroxy-3-methoxybenzyl)nonanamide, 5-[5- (1, 3- benzodioxol-5-yl)-l-(l-piperidinyl)-2,4-pentadien-l-one, 6-isopropyl-3,9-dimethyl- 1 ,4- dioxaspiro[4.5]decan-2-one, 2-isopropyl-N,2,3-trimethylbutanamide, and, 7-isopropyl-4,10- dimethyl-tricyclo[4.4.0.0(l,5)]decan-4-ol, 3-menthyl-3,6- dioxaheptanoate, 3-menthyl methoxyacetate, 3-menthyl-3,6,9-trioxadecanoate, 3-menthyl-(2-hydroxyethoxy)acetate, menthyl-ll-hydroxy-3,6,9-trioxadecanoate, 3S,5R,6S,9R)-6-isopropyl-3,9-dimethyl-l,4- dioxaspiro[4.5]decan-2-one, (3S,5S,6S,9R)- 6-isopropyl-3,9-dimethyl-l,4- dioxaspiro[4.5]decan-2-one, 2,3-dihydroxypropyl (IR,2S,5R)-2-isopropyl-5-methylcyclohexane carboxylate, (3S,5R,6S,9R)-6-isopropyl- 3,9-dimethyl-l,4-dioxaspiro[4.5]decan-2-one, (3S,5S,6S,9R)-6-isopropyl-3,9-dimethyl- l,4-dioxaspiro[4.5]decan-2-one, (IR,2S,5R)-N-(tert- butyl)-2-isopropyl-5-methyl- cyclohexanecarboxamide; and the bitter component is selected from the group consisting of bitter triterpenes, glucosides of monoterpenes, sesquiterpene lactones, humulone, lupulone, flavonones, and quinines. The disclosed flavour compositions are formulated to be devoid of off-notes, however, no alcohol enhancing effect of polygodial is disclosed, nor are any details disclosed at which concentration such an alcohol enhancing effect may occur, and none of the examples relates to an alcoholic beverage.

The enhancing effects in combination with ethanol that the applicant discovered for polygodial and warburganal have not been previously known. By combining an alcohol enhancer of general formula I (R1=H for polygodial or RI=OH for warburganal) with ethanol, the taste sensation caused by ethanol is enhanced. This allows to form compositions and food products which have an enhanced effect of the associated alcohol taste sensation but still similar enough in duration and onset to provide an authentic taste mimicking the taste of alcohol.

SUMMARY Provided are:

(1) A composition comprising one or more alcohol enhancer of general formula I

Fl wherein R 1 is a residue selected from the group consisting of H (polygodial) and OH (warburganal), in a total concentration of 0.25 ppm to 100 ppm, in combination with ethanol, wherein ethanol has a concentration of at least 1 % (wt/wt).

Such compositions include, for example, flavour compositions, food products, compositions for products placed in the oral cavity, and the latter products.

(2) The composition described under item (1) with the proviso that when the alcohol enhancer is polygodial, the composition does not comprise a mixture of a cooling component and a bitter component. By cooling component is meant a so-called cooling or minty compound as described in WO 2006/109241, i.e. selected from the group consisting of menthol, menthyl succinate, menthyl lactate, p-menthane-3,8-diol, 8-p-menthen-3-ol, 3-(3'-P-menthanyloxy)-l,2-propanediol, menthone glycerol ketal, 2-(l-methyl propyl)-l-cyclohexanone, N-ethyl-3-P- menthanecarboxamide, aspartic acid, N-(4-hydroxy-3-methoxybenzyl)nonanamide, 5-[5- (1, 3- benzodioxol-5-yl)-l-(l-piperidinyl)-2,4-pentadien-l-one, 6-isopropyl-3,9-dimethyl- 1 ,4- dioxaspiro[4.5]decan-2-one, 2-isopropyl-N,2,3-trimethylbutanamide, and, 7-isopropyl-4,10- dimethyl-tricyclo[4.4.0.0(l,5)]decan-4-ol, 3-menthyl-3,6- dioxaheptanoate, 3-menthyl methoxyacetate, 3-menthyl-3,6,9-trioxadecanoate, 3-menthyl-(2-hydroxyethoxy)acetate, menthyl-ll-hydroxy-3,6,9-trioxadecanoate, 3S,5R,6S,9R)-6-isopropyl-3,9-dimethyl-l,4- dioxaspiro[4.5]decan-2-one, (3S,5S,6S,9R)- 6-isopropyl-3,9-dimethyl-l,4- dioxaspiro[4.5]decan-2-one, 2,3-dihydroxypropyl (IR,2S,5R)-2-isopropyl-5-methylcyclohexane carboxylate, (3S,5R,6S,9R)-6-isopropyl- 3,9-dimethyl-l,4-dioxaspiro[4.5]decan-2-one, (3S,5S,6S,9R)-6-isopropyl-3,9-dimethyl- l,4-dioxaspiro[4.5]decan-2-one, (IR,2S,5R)-N-(tert- butyl)-2-isopropyl-5-methyl- cyclohexanecarboxamide. Cooling compounds may also include cooling compounds disclosed in H. R. Watson, Flavor: Its Chemical, Behavioural and Commercial Aspects Apt, C. M. Ed. Westview; Boulder co© (1977), 31-50. By bitter component is meant a bitter component as described in WO 2006/109241 , i.e. a compound or extract having bitter organoleptic properties selected from bitter triterpenes, glucosides of monoterpenes, sesquiterpene lactones, humulone, lupulone, flavonones, and quinines including bitter plant extracts including Quassia extract (also called bitter ash extract, FEMA No. 2971), quinquina extract, chamomile oils (FEMA No. 2272 to 2274), gentian root extract (FEMA No. 2506), hops extracts and oils (FEMA No. 2578 to 2580), and artichoke leaves oil. (3) The composition described under any one of items (1) and (2) additionally comprising dihydrogalangal acetate, optionally in a concentration from 5 ppm to 500 ppm, or 8 ppm to 250 ppm, or 10 to 30 ppm.

(4) The composition described under any one of items (1) to (3) which is an alcoholic beverage or a food product comprising an alcoholic beverage.

(5) The composition described under any one of items ( 1 ) to (3) which is a flavour composition for an alcoholic beverage or a food product comprising an alcoholic beverage comprising at least one excipient.

(6) The composition as described under any one of items (1) to (5) wherein the alcohol enhancer is present in a total concentration from 0.25 ppm to 75 ppm, optionally 1 ppm to 50 ppm.

(7) A method of enhancing the taste sensations associated with alcohol, wherein one or more alcohol enhancer of general formula I

wherein R 1 is a residue selected from the group consisting of H (polygodial) and OH (warburganal), in a total concentration from 0.25 ppm to 100 ppm is mixed with at least 1% wt/wt ethanol to provide a food product or flavour composition for a food product to enhance the taste of alcohol.

(8) The method as described under item (7) with the proviso that when the alcohol enhancer is polygodial, the composition does not comprise a mixture of a cooling component and a bitter component wherein the cooling component is selected from the group consisting of menthol, menthyl succinate, menthyl lactate, p-menthane-3,8-diol, 8-p-menthen-3-ol, 3-(3'-P- menthanyloxy)-l,2-propanediol, menthone glycerol ketal, 2-(l-methylpropyl)-l-cyclohexanone, N-ethyl-3-P- menthanecarboxamide, aspartic acid, N-(4-hydroxy-3- methoxybenzyl)nonanamide, 5-[5- (l,3-benzodioxol-5-yl)-l-(l-piperidinyl)-2,4-pentadien-l-one, 6-isopropyl-3,9-dimethyl- 1 ,4-dioxaspiro[4.5]decan-2-one, 2-isopropyl-N,2,3- trimethylbutanamide, and, 7-isopropyl-4,10-dimethyl-tricyclo[4.4.0.0(l,5)]decan-4-ol, 3- menthyl-3,6- dioxaheptanoate, 3-menthyl methoxyacetate, 3-menthyl-3,6,9-trioxadecanoate, 3-menthyl-(2-hydroxyethoxy)acetate, menthyl-ll-hydroxy-3,6,9-trioxadecanoate, 3S,5R,6S,9R)-6-isopropyl-3,9-dimethyl-l,4-dioxaspiro[4.5]decan-2-one, (3S,5S,6S,9R)- 6- isopropyl-3,9-dimethyl-l,4-dioxaspiro[4.5]decan-2-one, 2,3-dihydroxypropyl (IR,2S,5R)-2- isopropyl-5-methylcyclohexane carboxylate, (3S,5R,6S,9R)-6-isopropyl- 3,9-dimethyl-l,4- dioxaspiro[4.5]decan-2-one, (3S,5S,6S,9R)-6-isopropyl-3,9-dimethyl- 1,4- dioxaspiro[4.5]decan-2-one, (IR,2S,5R)-N-(tert-butyl)-2-isopropyl-5-methyl- cyclohexanecarboxamide; and the bitter component is selected from the group consisting of bitter triterpenes, glucosides of monoterpenes, sesquiterpene lactones, humulone, lupulone, flavonones, and quinines.

(9) The method described under any one of items (7) and (8) wherein the one or more alcohol enhancer is added in a total concentration from 0.25 ppm to 75 ppm, optionally 1 ppm to 50 ppm. DETAILED DESCRIPTION

By enhancing is meant the effect of an ingredient or compound on the taste sensation associated with alcohol which is found more pronounced (stronger, enhanced) in its taste intensity and/or which is found to last longer when comparing to the product without added enhancer compound and/or which is found to have an earlier onset of the flavour sensation so as to mimic the taste of a higher percentage of alcohol than actually present. Therefore, to be an effective enhancer of the taste of alcohol, the enhancer has to have high alcohol enhancing intensity but the taste profile, including in particular duration and onset of the taste sensation, should not be so different as to be perceived as a different taste rather than an enhanced taste of alcohol. For example, a compound providing an enhancement effect lasting more than up to 3 minutes (or up to 1 or 2 minutes, depending on the alcohol concentration and the enhancement effect to be achieved), i.e. much longer than alcohol even at high concentration of alcohol, will not be able to mimic alcohol very effectively (this depends on the alcohol concentration and sensation to be achieved - a higher concentration of alcohol will provide a taste sensation that lasts longer compared to a low concentration). For the onset, this mainly depends on the taster/panelist and for alcohol can vary from immediate to up to 5 seconds, or even longer. In addition to being similar enough in duration and onset to still mimic the taste of alcohol, a good alcohol enhancer should have very little aroma and/or no or little off-taste when used at an effective alcohol-enhancing concentration so that the enhancer may be added to any alcoholic beverage without having to reformulate the composition of the beverage due to the change in aroma. Off-taste is an undesired taste (any taste apart from alcohol taste). Particularly undesirable is an off-taste of long duration that will be more noticeable as an after-taste once the alcohol taste sensation stopped.

The synonymes and chemical structures of the alcohol enhancers are shown below.

Polygodial or ( 1R,4aS,8aS)-1 ,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-1 ,2- naphthalenedicarboxaldehyde is also known as Drim-7-ene-11,12-dial or Tadeonal, CAS # 6754-20-7: Warburganal or (1S,4aS,8aS)-1,4,4a,5 6,7,8,8a-octahydro-1-hydroxy-5,5,8a-trimethyl-1,2- naphthalenedicarboxaldehyde, CAS # 62994-47-2:

The enhanced alcoholic compositions may optionally be combined with one or more additional alcohol boosting compounds described in EP 0933030. These alcohol boosting compounds include the compounds below:

A compound of general formula Il

F II wherein

A = H1 OR4 X = OH, OCOR1

Y = H, OCOR3 and

R1, R3 = H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, branched or unbranched R2 = H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, branched or unbranched, C3 - C6 carbocycle, substituted or unsubstituted

R4 = C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, branched or unbranched.

Compounds of formula FII include, without limitation, compounds a) to v) of table I in EP 0933030, wherein R is selected from the group consisting of H, CH3, CH2CH3, and CH(CH3)2. Compounds of formula FII further include, without limitation, compounds of table Il in EP 0933030, and compound of example 6 of EP 0933030, (rac)-acetic acid 1-(4- acetoxyphenyl)-propylester), also known as dihydrogalangal acetate, or as 4-(acetyloxy)- α- ethyl-benzenemethanol acetate, CAS # 129319-15-9:

The appropriate concentration of the alcohol enhancing and alcohol boosting compounds can be easily tested by an organoleptic titration. This technique is well known in the field of sensory analysis. Some examples, without limitation, are indicated below. In alcoholic beverages, the concentration depends on the ethanol concentration and on the desired degree of enhancement of the alcohol sensation. For example, an alcohol enhancer concentration from 0.25 to 100 ppm is generally useful for ethanol concentrations of 5% to 100%, for example 60 to 70% ethanol, and 65 to 70% ethanol, with most applications within the range of 0.25 to 75 ppm or 1 to 50 ppm. Higher concentrations of ethanol will need a higher concentration of the alcohol enhancer. Alcohol boosting compounds, for example, without limitation, dihydrogalangal acetate, can be added in a similar concentration or higher, for example up to 250 ppm.

The alcohol enhancers may be used in any convenient for, for example, without limitation, in form of the synthetic compounds, in form of purified compounds (for example, without limitation, at least 80, 90, 95 or 98 % purity wt/wt), or purified from a botanical extract, removing undesired aroma compounds. Useful botanical extracts include, without limitation, extracts from water pepper including its so-called "redbud" seedlings (Polygonum hydropiper), New Zealand Horopito (Pseudowintera colorata), Australian Tasmanian pepper (Tasmannia lanceolata), African pepper-bark tree

(Warburgia ugandensis, W. stuhlmannii and W. salutaris, all family of Canellaceae ), or other plant extracts with a concentration enriched (for example, to provide an alcohol enhancer concentration of, for example, without limitation, at least 10%, optionally at least 30%, at least 50%, or at least 70% in one or more of polygodial, and warburganal.

Alcoholic products (including alcoholic beverages) as herein described comprise a minimum ethanol concentration of 1% or more, or 5% or more, for example 5 to 100%, 5 to 70%, 20 to 70%, 30 to 70%, and 40 to 70%, 30 to 52%, and 40 to 52%.

Flavour compositions comprise one or more alcohol enhancer and ethanol, and optionally at least one food grade excipient. Suitable excipients for flavour compositions are well known in the art and include, for example, without limitation, solvents (including water, alcohol, ethanol, oils, fats, vegetable oil, and miglyol), binders, diluents, disintegranting agents, lubricants, flavoring agents, coloring agents, preservatives, antioxidants, emulsifiers, stabilisers, flavor- enhancers, sweetening agents, anti-caking agents, and the like. Examples of such carriers or diluents for flavours may be found e.g. in ,,Perfume and Flavor Materials of Natural Origin,,, S. Arctander, Ed., Elizabeth, N.J., 1960; in "Perfume and Flavor Chemicals", S. Arctander, Ed.,

Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; in "Flavourings", E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998, and "CTFA Cosmetic Ingredient Handbook", J.M. Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988. The flavour composition may contain additional flavour ingredients including flavour compounds, flavours from natural sources including botanical sources and including ingredients made by . The flavour composition may have any suitable form, for example liquid or solid, wet or dried, or in encapsulated form bound to or coated onto carriers/particles or as a powder.

Alcoholic beverages as herein described comprise a minimum ethanol concentration of 1% or more, or 5% or more, for example 5 to 100%, 5 to 70%, 20 to 70%, 30 to 70%, and 40 to 70%, 30 to 52%, and 40 to 52%. Alcoholic beverages include fermented and distilled beverages. Fermented alcoholic beverages may be obtained from starchy or sugary plants or plant parts including, without limitation, grains, or juices, vegetables, cane, or others. Grains include, without limitation, , , corn, , , , or others. Fruits include grapes, apples, pears, , molasses, , plums, pineapples, bananas, plantains, gouqi, and others. Vegetables include , , , manioc, juca, and others. Other materials that can be fermented and/or distilled include, without limitation, palm sap, honey, , milk, sugar, and others. The resulting alcoholic beverages include, without limitation, , , barley , rye beer, , , corn beer, beer brewed from sorghum, wheat beer, , choujiu, , , makkoli, tuak, thwon, wine, (including, without limitation, Port and ), sparkling wine, , liquers, spirits, , , , rum, , Scotch whiskey, , , (German Weizenkorn), , Chinese , , gaoliang, , rice baijiu, , , , brandy, , , , Branntwein, , "" (also known as Rakiya, Rakija, or Raki), singani, palinka, cider, , apple brandy, , pear cider, pear brandy, eau-de- vie, , rum, pinga (aslo cachaga), , , , , , plum wine, , tzuica, palinca, umeshu, , urgwagwa, mbege, kasikisi, gouqi jiu, ginger beer, potato beer, aquavit, brennivfn, Poitin (also poteen), pink vodka, nihimanchi, , chicha, coyol wine, tembo, , teg, distilled mead (also mead brandy or honey brandy), pomace wine, , Trester, marc, , aguardente, tescovina, , araka, kilju, and others.

Food products comprising alcoholic beverages include, without limitation, confectionary products, chocolate, pralines, truffes, and prepared foods comprising alcoholic beverages including, without limitation, wine, champagne, brandy, whiskey and rum. Examples

All percentages given are wt/wt, unless indicated otherwise. Alcohol (ethanol) is indicated as "proof, which is twice the percentage of the alcohol content measured by volume. For example, 10 proof alcohol is 5%, 40 proof is 20%, 190 proof is 95%.

Example 1 Taste evaluations

For taste evaluations, test samples were prepared by adding test compounds and tastants to a reference sample. The references contained the tastant in the same or a higher concentration, but without the test compound (putative enhancer). Test samples and reference samples were prepared fresh and served at room temperature in flavorless, odorless 1 oz souffle cups. Drinking water was used to rinse and clean the palate between samples. Each test sample was evaluated by 2 to 7 panelists for its relevant taste intensity and lasting effect of the taste sensation in comparison to each reference sample. The intensity was rated as follows: —none, +=weak, ++=noticeable, +++= strong, ++++= very strong.

To evaluate the enhancement of alcohol, test samples were prepared in a 40 proof ethanol cordial (48 parts distilled water, 30 parts medium invert sugar, 2 1 parts 95% ethyl alcohol and 1 part glycerine) with higher concentrated reference samples at 50, 60 or 70 proof ethanol. Reference samples had the same ethanol cordial of 50, 60, and 70 proof ethanol with the same sugar and glycerine content.

The panelists evaluated the taste of the samples and compared the taste intensity of each sample (alcoholic taste) with one or more reference samples.

Polygodial and warburganal at the tested concentrations (5-50 ppm) in water was found to have no significant aroma of their own. Example 2 Qualitative evaluation of the enhancement of alcohol taste intensity by polyqodial

The taste evaluation was performed as described in example 1. The tested alcohol concentrations and polygodial concentrations and their results are indicated in the table below.

These results show that polygodial increases the alcohol sensation of alcohol bases at the tested concentrations. The optimal concentration range of polygodial is between 5 to 10 ppm. Example 3 Qualitative evaluation of the enhancement of alcohol taste duration by mixtures of polyqodial and dihvdroqalanqal acetate

The taste evaluation and its duration was performed as described in example 1. The tested alcohol, dihydrogalangal acetate and polygodial concentrations and their results are indicated in the table below.

These results show that both polygodial and dihydrogalangal acetate increased the alcohol sensation of alcohol bases at the tested concentrations. Polygodial has a slightly delayed onset of enhancement but the enhancement lasts longer. Dihydrogalangal acetate has a relatively short enhancement duration but the enhancement can be perceived from the very start. The mixture of polygodial and dihydrogalanagal acetate provides an enhancement of intensity and duration with an immediate onset. Example 4 Quantitative evaluation of the enhancement of alcohol taste by 5 ppm polyqodial

A taste evaluation on the taste of alcohol was performed as described in example 1, with 7 panelists.

Test samples contained 5 ppm polygodial in a 40 proof ethanol cordial. The results are indicated in the table below (number of panelists choosing the respective reference samples are indicated)

All panelists noted an alcohol taste in the 40 proof with 5 ppm polygodial test sample that was similar in intensity and duration to the 50 proof reference or above, but below the 70 proof reference. 3 of these panelists indicated the sample was near the 50 proof reference, 2 of the panelists indicated the sample was between 50 and 60 proof, 2 of the panelists indicated it was near 60 proof in intensity and duration.

Example 5 Quantitative evaluation of the enhancement of alcohol taste by 5 ppm polyqodial and 12 ppm dihydroqalanqal acetate

A taste evaluation on the taste of alcohol was performed as described in example 1, with 4 panelists.

Test samples contained 5 ppm polygodial and 12 ppm dihydrogalangal acetate in a 40 proof ethanol cordial. The results are indicated in the table below (number of panelists choosing the respective reference samples are indicated). All panelists noted an alcohol taste in the 40 proof with 5 ppm polygodial and 12 ppm dihydrogalangal acetate test sample that was similar in intensity and duration and onset to the 50 proof or 60 proof reference, but below the 70 proof reference. 1 panelist found the sample exceeded the 50 proof reference and was equal to the alcohol taste of the 60 proof reference in intensity and duration.

Example 6 Quantitative evaluation of the enhancement of alcohol taste by 5 ppm polvαodial and 25 ppm dihydrogalangal acetate

A taste evaluation on the taste of alcohol was performed as described in example 1, with 2 panelists.

Test samples contained 5 ppm polygodial and 25 ppm dihydrogalangal acetate in a 40 proof ethanol cordial. The results are indicated in the table below (number of panelists choosing the respective reference samples are indicated).

All panelists noted an alcohol taste in the 40 proof with 5 ppm polygodial and 25 ppm dihydrogalangal acetate test sample that was similar in intensity and duration and onset at least to the 50 proof reference, but below the 70 proof reference. 1 panelist indicated the sample was near the 50 proof reference and 1 panelist found the sample exceeded the 50 proof reference and was at least equal to the alcohol taste of the 60 proof reference in intensity and duration.

Example 7 Quantitative evaluation of the enhancement of alcohol taste by 5 ppm warburganal

A taste evaluation on the taste of alcohol was performed as described in example 1, with 6 panelists. Test samples contained 5 ppm warburganal in a 40 proof ethanol cordial. The results are indicated in the table below (number of panelists choosing the respective reference samples are indicated)

All panelists noted an alcohol taste in the 40 proof with 5 ppm warburganal test sample that was similar in intensity and duration to the 50 proof or 60 proof reference, but below the 70 proof reference. 2 panelists indicated the 5 ppm warburganal in 40 proof alcohol sample was near the 50 proof reference, 4 panelists indicated the sample was near 60 proof in intensity and duration.

Example 8 Comparative qualitative evaluation of the enhancement of alcohol taste: comparison of polyqodial and warburqanal

A taste evaluation on the taste of alcohol was performed as described in example 1 with 6 panelists.

Both warburganal and polygodial were used at 5 ppm each in 40 proof ethanol cordial, and compared to a 40 proof reference. In comparison, alcohol taste enhancement of warburganal was found to be stronger with an earlier onset than polygodial. Claims

1. A composition comprising one or more alcohol enhancers of general formula I

wherein R 1 is a residue selected from the group consisting of H (polygodial) and OH (warburganal) in a total concentration of 0.25 ppm to 100 ppm, in combination with ethanol, wherein ethanol has a concentration of at least 1 % (wt/wt).

2. The composition of claim 1 with the proviso that when the alcohol enhancer is polygodial, the composition does not comprise a mixture of a cooling component and a bitter component.

3. The composition of any one of claims 1 and 2 additionally comprising dihydrogalangal acetate, optionally in a concentration from 5 ppm to 500 ppm, or 8 ppm to 250 ppm, or 10 to 30 ppm.

4. The composition of any one of claims 1 to 3 which is an alcoholic beverage or a food product comprising an alcoholic beverage.

5. The composition of any one of claims 1 to 3 which is a flavour composition for an alcoholic beverage or a food product comprising an alcoholic beverage comprising at least one excipient.

6. The composition of any one of claims 1 to 5 wherein total concentration of the alcohol enhancer is from 0.25 ppm to 75 ppm, optionally from 1 ppm to 50 ppm.

7. A method of enhancing the taste sensations associated with alcohol, wherein one or more alcohol enhancer of general formula I wherein R 1 is a residue selected from the group consisting of H (polygodial) and OH (warburganal) in a total concentration of 0.25 ppm to 100 ppm is mixed with at least 1% wt/wt ethanol to provide a food product or flavour composition for a food product to enhance the taste of alcohol.

8. The method of claim 7 with the proviso that when the alcohol enhancer is polygodial, the composition does not comprise a mixture of a cooling component and a bitter component.

9. The method of any one of claims 7 and 8 wherein the one or more alcohol enhancer is added in a total concentration from 0.25 ppm to 100 ppm, optionally 0.5 ppm to 100 ppm, and 1 ppm to 50 ppm. A. CLASSIFICATION OF SUBJECT MATTER INV. A23L1/221 C12G3/06

According to International Patent Classification (IPC) or to both national classification and IPC

B. FIELDS SEARCHED Minimum documentation searched (classification system followed by classification symbols) A23L C12C C12G C12H

Documentation searched other than minimum documentation to the extent that such documents are included in the fields searched

Electronic data base consulted during the international search (name of data base and, where practical, search terms used) EPO-Internal , WPI Data, FSTA, BIOSIS

C. DOCUMENTS CONSIDERED TO BE RELEVANT

Category* Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No

US 5 523 105 A (ISHIKAWA HISASHI [JP] ET 1,2,5,6 AL) 4 June 1996 (1996-06-04) cited in the application example 4 column 2 , line 5 - line 18 7-9

WO 2007/013811 A (QUEST INT SERV BV [NL]; 1-9 WINKEL CHRIS [NL]; KAOUAS ABDELMAJID [NL]; NOO) 1 February 2007 (2007-02-01) page 4 , line 13 - page 5 , line 10 examples 2,12

Further documents are listed in the continuation of Box C See patent family annex

* Special categories of cited documents "T" later document published after the international filing date or pnoπty date and not in conflict with the application but 'A' document defining the general state of the art which is not cited to understand the principle or theory underlying the considered to be of particular relevance invention 'E' earlier document but published on or after the international 'X' document of particular relevance, the claimed invention filing date cannot be considered novel or cannot be considered to 'L' document which may throw doubts on pnoπty claιm(s) or involve an inventive step when the document is taken alone which is cited to establish the publication date of another 'Y' document of particular relevance, the claimed invention citation or other special reason (as specified) cannot be considered to involve an inventive step when the O ' document referring to an oral disclosure, use, exhibition or document is combined with one or more other such docu¬ other means ments, such combination being obvious to a person skilled 'P' document published prior to the international filing date but in the art later than the priority date claimed ■&1 document member of the same patent family

Date of the actual completion of the international search Date of mailing of the international search report

16 March 2009 27/03/2009

Name and mailing address of the ISA/ Authorized officer European Patent Office P B 5818 Patentlaan 2 NL - 2280 HV Ri|swi|k TeI (+31-70) 340-2040, Fax (+31-70) 340-3016 Vermeulen, Stephane

Form PCT/ISA/210 (second sheet) (April 2005) C(Contlnuation). DOCUMENTS CONSIDERED TO BE RELEVANT

Category * Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No

WO 2005/044778 A (SYMRISE GMBH & CO KG 1-9 [DE]; LEY JAKOB [DE]; KINDEL GUENTER [DE]; KRAMME) 19 May 2005 (2005-05-19) page 2 , line 20 - page 4 , line 2 page 6 , line 10 - line 2 1 page 7 , line 9 page 7 , line 15 page 13, line 11 - line 17 examples 6-9

EP 0 933 030 A (GIVAUDAN ROURE INT [CH] 1-9 GIVAUDAN SA [CH]) 4 August 1999 (1999-08-04) cited in the application paragraph [0010]

WO 01/15534 A (AUSTRALIAN NATIVE FOODS 1-6 RESOUR [AU]; MILGATE BRIAN [AU]; BASTA ALBERT) 8 March 2001 (2001-03-08) page 3 , line 5 - line 8 page 4 , line 10 - line 15

Form PCT/ISA/210 (continuation of second sheet) (April 2005) Patent document Publication Patent family Publication cited in search report date member(s) date

US 5523105 04-06-1996 JP 7145398 A 06-06-1995

WO 2007013811 A 01-02-2007 NONE

WO 2005044778 A 19-05-2005 CN 1878745 A 13-12-2006 DE 10351422 A l 16-06-2005 EP 1682489 A l 26-07-2006 JP 2007510634 T 26-04-2007 US 2007202188 A l 30-08-2007

EP 0933030 A 04-08-1999 EP 1700525 A2 13-09-2006

WO 0115534 A 08-03-2001 CA 2348976 Al 08-03-2001 EP 1124425 A l 22-08-2001 JP 2003508414 T 04-03-2003

Form PCT/ISA/210 (patent family annex) (April 2005)