WO2009065239A1 - Compositions et leur utilisation - Google Patents

Compositions et leur utilisation Download PDF

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Publication number
WO2009065239A1
WO2009065239A1 PCT/CH2008/000481 CH2008000481W WO2009065239A1 WO 2009065239 A1 WO2009065239 A1 WO 2009065239A1 CH 2008000481 W CH2008000481 W CH 2008000481W WO 2009065239 A1 WO2009065239 A1 WO 2009065239A1
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WO
WIPO (PCT)
Prior art keywords
ppm
alcohol
taste
polygodial
composition
Prior art date
Application number
PCT/CH2008/000481
Other languages
English (en)
Inventor
Xiaogen Yang
Zhonghua Jia
Jason Jordan
Original Assignee
Givaudan Sa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Givaudan Sa filed Critical Givaudan Sa
Publication of WO2009065239A1 publication Critical patent/WO2009065239A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C5/00—Other raw materials for the preparation of beer
    • C12C5/02—Additives for beer
    • C12C5/026—Beer flavouring preparations
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/203—Alicyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G1/00—Preparation of wine or sparkling wine
    • C12G1/06—Preparation of sparkling wine; Impregnation of wine with carbon dioxide
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G3/00—Preparation of other alcoholic beverages
    • C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
    • C12G3/06—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs with flavouring ingredients
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G2200/00—Special features
    • C12G2200/21—Wine additives, e.g. flavouring or colouring agents

Definitions

  • 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.
  • Alcohol 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).
  • ethanol alcohol
  • 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-piperidin
  • composition comprising one or more alcohol enhancer of general formula I
  • R1 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).
  • compositions include, for example, flavour compositions, food products, compositions for products placed in the oral cavity, and the latter products.
  • 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.
  • 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
  • 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.
  • 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.
  • composition described under any one of items (1) to (3) which is an alcoholic beverage or a food product comprising an alcoholic beverage.
  • 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.
  • R1 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.
  • 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
  • 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.
  • 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).
  • this mainly depends on the taster/panelist and for alcohol can vary from immediate to up to 5 seconds, or even longer.
  • 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.
  • Polygodial or (1 R,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:
  • 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:
  • 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)- ⁇ - 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.
  • concentration depends on the ethanol concentration and on the desired degree of enhancement of the alcohol sensation.
  • 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 Georgian pepper (Tasmannia lanceolata), African pepper-bark tree (Warburgia ugandensis, W. stuhlmannii and W.
  • 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 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.
  • solvents including water, alcohol, ethanol, oils, fats, vegetable oil, and miglyol
  • binders 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, emulsifier
  • the flavour composition may contain additional flavour ingredients including flavour compounds, flavours from natural sources including botanical sources and including ingredients made by fermentation.
  • 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, fruits or fruit juices, vegetables, sugar cane, or others.
  • Grains include, without limitation, barley, rye, corn, sorghum, wheat, rice, millet or others.
  • Fruits include grapes, apples, pears, sugarcane, molasses, agave, plums, pineapples, bananas, plantains, gouqi, and others.
  • Vegetables include ginger, potato, cassava, manioc, apparently, and others.
  • Other materials that can be fermented and/or distilled include, without limitation, palm sap, honey, pomace, milk, sugar
  • the resulting alcoholic beverages include, without limitation, beer, ale, barley wine, rye beer, kvass, chicha, corn beer, beer brewed from sorghum, wheat beer, huangjiu, choujiu, sake, thanki, makkoli, tuak, thwon, wine, fortified wine (including, without limitation, Port and Sherry), sparkling wine, cider, liquers, spirits, vodka, brandy, gin, rum, whisky, Scotch whiskey, Irish whiskey, rye whiskey, wheat whiskey (German Weizenkorn), bourbon whiskey, Chinese liquor, maotai, gaoliang, baijiu, rice baijiu, Shochu, Awamori, soju, brandy, Cognac, Vermouth, Armagnac, Branntwein, pisco, "Rakia” (also known as Rakiya, Rakija, or Raki), singani, palinka, cider, apfelwein, apple brandy, calvados
  • 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.
  • Alcohol 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%.
  • 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.
  • test samples were prepared in a 40 proof ethanol cordial (48 parts distilled water, 30 parts medium invert sugar, 21 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.
  • the optimal concentration range of polygodial is between 5 to 10 ppm.
  • 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)
  • 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).
  • 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).
  • a taste evaluation on the taste of alcohol was performed as described in example 1 with 6 panelists.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Polymers & Plastics (AREA)
  • Seasonings (AREA)
  • General Preparation And Processing Of Foods (AREA)

Abstract

L'invention propose des compositions qui comportent des ingrédients rehaussant le goût de l'alcool en vue d'une utilisation dans des boissons alcoolisées, et des boissons alcoolisées à goût rehaussé qui comportent lesdits ingrédients. Les agents rehaussant le goût de l'alcool sont le polygodial et le warburganal, ou des extraits comportant ces composés, lesquels, lorsqu'ils sont combinés à de l'alcool (éthanol), augmentent son intensité et imitent sa durée et son attaque en bouche.
PCT/CH2008/000481 2007-11-19 2008-11-17 Compositions et leur utilisation WO2009065239A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US98886707P 2007-11-19 2007-11-19
US60/988,867 2007-11-19

Publications (1)

Publication Number Publication Date
WO2009065239A1 true WO2009065239A1 (fr) 2009-05-28

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2932858A1 (fr) 2014-04-16 2015-10-21 Symrise AG Ester d'acide homovallinique, en particulier pour obtenir une impression de chaleur et/ou de netteté
US10045952B2 (en) 2013-06-25 2018-08-14 Forest Herbs Research Limited Anti-Viral Compound and Composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5523105A (en) * 1993-11-24 1996-06-04 Lotte Company Limited Improved mint composition and method for producing the same
EP0933030A2 (fr) * 1997-12-22 1999-08-04 Givaudan-Roure (International) S.A. Composants d'arÔme piquant
WO2001015534A1 (fr) * 1999-08-26 2001-03-08 Australian Native Foods Resource Development Pty Ltd Composition insecticide
WO2005044778A1 (fr) * 2003-11-04 2005-05-19 Symrise Gmbh & Co. Kg Utilisation de n-alkylamides de l'acide alcene-caboxylique en tant qu'aromatisants
WO2007013811A2 (fr) * 2005-07-29 2007-02-01 Quest International Services B.V. Substances modulant la saveur

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5523105A (en) * 1993-11-24 1996-06-04 Lotte Company Limited Improved mint composition and method for producing the same
EP0933030A2 (fr) * 1997-12-22 1999-08-04 Givaudan-Roure (International) S.A. Composants d'arÔme piquant
WO2001015534A1 (fr) * 1999-08-26 2001-03-08 Australian Native Foods Resource Development Pty Ltd Composition insecticide
WO2005044778A1 (fr) * 2003-11-04 2005-05-19 Symrise Gmbh & Co. Kg Utilisation de n-alkylamides de l'acide alcene-caboxylique en tant qu'aromatisants
WO2007013811A2 (fr) * 2005-07-29 2007-02-01 Quest International Services B.V. Substances modulant la saveur

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10045952B2 (en) 2013-06-25 2018-08-14 Forest Herbs Research Limited Anti-Viral Compound and Composition
EP2932858A1 (fr) 2014-04-16 2015-10-21 Symrise AG Ester d'acide homovallinique, en particulier pour obtenir une impression de chaleur et/ou de netteté

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