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WO 2009/065239 Al (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, HU, 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). JIA, 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 (ethanol) 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 drinks, 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.
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