WO2006087370A1

WO2006087370A1 - Use of aroma glycosides as flavor or fragrance ingredient

Info

Publication number: WO2006087370A1
Application number: PCT/EP2006/060056
Authority: WO
Inventors: Ole Rye Jensen; Finn Okkels Thyge
Original assignee: Poalis A/S
Priority date: 2005-02-18
Filing date: 2006-02-17
Publication date: 2006-08-24

Abstract

Use of aroma glycosides as flavor or fragrance ingredients in food, feed, cleaning liquid or a washing powder products.

Description

TITLE: Use of aroma glycosides as flavor or fragrance ingredient.

FIELD OF THE INVENTION:

The invention relates to use of aroma glycosides as flavor or fragrance ingredients in food, feed, cleaning liquid or a washing powder products.

BACKGROUND OF THE INVENTION:

It is known that many aroma compounds (e.g. vanillin) in plants are stored as glycosides and only released during ripening or through infection or attach from insects or other damage. The aroma compounds are released via deglycosylation of the glycosides (e.g. vanillin glycoside) to get the corresponding aglycon (e.g. vanillin). It is the corresponding aglycon that is the active aroma compound.

The focus in use for industrial flavor or fragrance solutions has generally been on the active aroma compound (the aglycone) and advantage has generally not been taken of the functionality of the glycoside for flavor or fragrance formulations used in e.g. food or feed products, cleaning liquids or washing powder. These are all areas where there is a high use and demand for flavor or fragrance formulations, especially formulations with improved functionality compared to existing formulations.

It is important that these formulations are as effective and stable as possible and that the flavor or fragrance release is controlled. Currently there are large problems with stability of flavor or fragrance solutions both as products but also when they are incorporated into e.g. the above mentioned final products. The instability can be linked to oxidation by other compounds in the formulation or the final product, to deterioration through reaction with other compounds either directly or mediated by oxygen and or light.

Other problems encountered by current solutions are instability when processed at higher temperature like cooking or UHT treatment or instability at high or low pH. Many high impact aroma compounds like mercaptans or lower alcohols have a low boiling point and therefore they evaporate during processing and storage.

Further many aroma compounds are very hydrophobic and their water solubility is low which makes it a problem to flavor water phases in integrated products since the aroma compound tend to be distributed in the fat phase.

SUMMARY OF THE INVENTION:

The problem to be solved by the present invention is to provide new flavor or fragrance formulations that are improved with regard to the above mentioned problems and will be a benefit for both the industry and the consumers.

The solution is based on using the glycosides of aroma compounds as part or as sole component in flavor or fragrance formulations. By using glycosides of aroma compounds many of the above problems can be solved or significantly improved.

In order to get a composition with a controlled purity of the glycosides the glycosides of aroma compounds shall be made synthetically (e.g. chemically or enzymatically). Said in other words, as a starting material, the present invention uses a composition consisting essentially of a synthetically made glycoside of an aroma compound, wherein the composition is free from compounds originating from an extract of a natural plant.

The glycosides of aroma compounds may herein be termed glycosylated form of an aroma aglycon compound. These terms may be used interchangeably herein.

Accordingly, a first aspect of the invention relates to use of a composition consisting essentially of a synthetically made glycosylated form of an aroma aglycon compound, wherein the composition is free from compounds originating from an extract of a natural plant, for making a flavor formulation and subsequent incorporation of the flavor formulation into a product selected from the group of products consisting of:

(i) a food product selected from the group of food products consisting of: a dairy product; a water in oil emulsion such as margarine or butter; a oil in water emulsion such as an edible ice a sherbet or a sorbet; a confectionery; a cereal or cereal product; a dessert, a bakery ware; a foodstuff intended for particular nutritional uses; a non-alcoholic ('soft') beverage; alcoholic beverages, including alcohol-free and low-alcoholic counterparts; and Ready-to-eat savouries;

(ϋ) feed products; resulting in a product comprising the glycosylated form of the aroma aglycon compound to give a suitable flavor.

The group of food products is selected from the list shown in Annex III with title "FOOD

CATEGORIES" of the EU Commission Regulation (EC) No 1565/2000 of 18 July 2000 relating to flavoring substances used or intended for use in or on foodstuffs.

A second aspect of the invention relates to use of a composition consisting essentially of a synthetically made glycosylated form of an aroma aglycon compound, wherein the composition is free from compounds originating from an extract of a natural plant, for making a fragrance formulation and subsequent incorporation of the fragrance formulation into a product selected from the group of products consisting of:

(i) a cleaning liquid or a washing powder. resulting in a product comprising the glycosylated form of the aroma aglycon compound to give a suitable fragrance.

When the glycosides of aroma compounds are used in e.g. food products the activation of the glycosides in the food products will take place after hydrolyzing the glycoside and liberating the aroma compound (aglycone). This takes e.g. place through activity of the glycosidases we have in the mouth cavity. In a working example herein this is demonstrated for vanillin glucoside. In this example the taste release of vanillin and vanillin glucoside was compared organoleptic from a 100 ppm solution and the taste panel found a distinct delay in the release of the aroma from vanillin glucoside compared to vanillin. In order words, the use of the vanillin glucoside gave a sustained release profile of the vanilla flavor. The sustained release profile of the flavor is a general feature that applies generally to the glycosides of aroma compounds. An advantage of this sustained release profile is that by making e.g. a food product that also comprises suitable aglycone aroma compound (e.g. vanillin) one will be able to get both the rapid flavor sensation of the aglycone aroma compound and the prolonged sustained release flavor profile of the glycosides of aroma compounds (e.g. from vanillin glycoside).

The activation of the glycosides may also take place through activity of added beta-glycosidase. The latter may be of particular interest in products such as cleaning liquids and washing powders. In such product one could have incorporated a suitable glycosidase that are active when the products are in contact with water.

DEFINITIONS:

Prior to a discussion of the detailed embodiments of the invention is provided a definition of specific terms related to the main aspects of the invention.

The term "aglycon" denotes non-carbohydrate part of the corresponding glycosylated form of the aglycon. It may also be defined as an acceptor compound capable of being conjugated to a sugar. In a number of relevant examples, the aglycon is an alcohol with a hydroxy group suitable for being glycosylated. When the sugar is glucose the aglycon may be termed aglucone. Further, when the sugar is glucose the term glucosylated may be used instead of glycosylated. An aglycon may also be glycosylated at different group than a hydroxy group, in particular at other nucleophilic groups such as a carboxylic acid, SH-, nitrogen, amine, imine or C-C group.

The term "aroma" denotes the impression of taste and odor.

The term "flavor" denotes the quality of something that affects the sense of taste of a food or feed product. As understood by the skilled person the term flavor does not include fragrance (used in e.g. perfumes or cosmetics) or sweeteners.

The term "fragrance" denotes the odor of a product. As understood by the skilled person the term fragrance does not include the flavor sense of taste of a food or feed product. The term "glycoside" denotes a compound which on hydrolysis gives a sugar and a non-sugar (aglycon) residue, e.g. glucosides give glucose, galactosides give galactose. If the sugar is glucose the compound may be termed glucoside. The sugar may e.g. be D and L isomers of galactose, glucosamine, N-acetylglusamine, xylose, glucuronic acid, rhamnose , arabinose, mannose or glucose. Alternatively the sugar may be a carbohydrate derivative such as e.g. inositol, D-olivose, rhodinose and etc available as nucleotide diphosphates. Further the sugar may for instance be e.g. a monosaccharide, a disaccharide or a trisaccharide. In the case of oligo- and polysaccharides the sugars are linked one by one. Further, a list of suitable sugars can be seen in US2003/0130205A1 paragraphs [0029] to [0036]. Preferably, the sugar is galactose, arabinose, mannose or glucose. Most preferably the sugar is glucose.

Embodiment(s) of the present invention is described below, by way of example(s) only

DETAILED DESCRIPTION OF THE INVENTION:

Features and advantages of using glycosides of aroma compounds

In general the difference between aroma compounds and the corresponding glycosides with regard to functionality is specified in the following overview.

Aglycone (e.g. vanillin) Glycoside (e.g. vanillin Glucoside)

Hydrophobic Hydrophilic

"Unstable" "Stable"

Low water solubility Water Soluble Metabolized Not metabolized

"High vapor pressure" "Low vapor pressure"

This can e.g. be used as:

Water soluble Improve distribution and stability in water phase of Food products

Below is given examples of relevant application and related benefits of using glycosides of aroma compounds.

Application area Benefits Natural extracts Spike and extend effect Low fat food/soft drink Add flavor to the water phase Processed foods/UHT Decrease flavor loss and generation of off flavors during processing and storage Confectionary Prolong and balance flavor during consumption

Cleaning liquids/powder Controlled release during application Food & Feed formulations Increased storage stability, Authentic taste profile

Hydrophobic — hydrophϊlic The water - oil coefficient is different for the glycoside and the corresponding aglycone. For instance for vanillin water - oil coefficient is sufficient different for in an oil in water emulsion like ice cream the vanillin glucoside will go into the water phase while vanillin will go into the fat phase. This may give a more uniform distribution of the flavor in the food product. See working example herein for further details. Stability

The storage stability of the glycoside is generally improved over the corresponding aglycone.

See working example herein for further details.

Water solubility

The water solubility of the glycoside is generally improved over the corresponding aglycone. See e.g. working example herein, wherein it is shown that at 30°C the solubility of vanillin glucoside in water is app. 35 g/1 corresponding to 16.8 g/1 vanillin while the vanillin solubility is only app. 11 g/1.

Resulting product comprising the glycosylated form of an aroma aglvcon

As explained above it may be an advantage that the resulting product comprising the glycosylated form of an aroma aglycon also comprises suitable aroma aglycon compounds. These may be an aroma aglycon compound, wherein the aglycon (e.g. vanillin) is the aglycon of the corresponding glycosylated form of an aroma aglycon (e.g. vanillin glucoside). However it may also be different aroma aglycon compounds. This will depend on the desired flavor profile of the product. Alternatively, the product may comprise aroma compounds originating from an extract of a natural plant.

Such a product may be made by incorporating the relevant aroma aglycon compounds in the flavor or fragrance formulation and add this to the product. However, such aroma aglycon compounds may alternatively be added separately to the product.

In a preferred embodiment, the resulting product is an oil in water emulsion product or a water in oil emulsion product wherein the product is comprising both glycosylated form of an aroma aglycon compound and aroma aglycon compound and wherein the water phase comprises glycosylated form of an aroma aglycon compound and the oil phase comprises aroma aglycon compound. In a preferred embodiment, the water phase comprises from 85 to essentially 100% of the glycosylated form of the aroma aglycon compounds of the product and the oil phase comprises from 85 to essentially 100% of the aroma aglycon compounds of the product. In a preferred embodiment, the oil in water emulsion product or a water in oil emulsion product is a feed product. More preferably it is a food product. Particular preferred examples of such food products are ice cream, dressings, desserts, functional food products or yellow fats.

For a number of products, it may be preferred that the product comprises a system to deglycosylating the glycosylated form of an aroma aglycon. This may be done by chemical hydrolysis according to known methods in the art. Preferably it is done by use of an enzyme with e.g. beta-glycosidase activity. Numerous suitable beta-glycosidases are known to the skilled person. This is particular preferred when the product comprises relatively high amounts of the glycosylated form of an aroma aglycon, such as for instance when the product from 50 to 100% of a specific aroma compound of product are glycosylated form of the specific aroma aglycon compounds. For instance, a product comprising 3 times more vanillin glucoside than vanillin.

When the food product is a non-alcoholic ('soft') beverage it is the preferred that the nonalcoholic ('soft') beverage comprises a system to deglycosylating the glycosylated form of an aroma aglycon. This may be done by chemical hydrolysis according to known methods in the art. Preferably this is done by use of an enzyme with e.g. beta-glycosidase activity. The system should preferably be made in a way wherein the deglycosylating activity is first activated just before one starts to drink the soft beverage. This may e.g. be a system that liberates an enzyme with beta-glycosidase activity when one opens the cap of the soft beverage bottle.

When the product is a cleaning liquid or washing powder it is preferred that the product comprises a system to deglycosylating the glycosylated form of an aroma aglycon. Preferably this is done by use of an enzyme with e.g. beta-glycosidase activity. To incorporate enzymes in a cleaning liquids or washing powder is routine work for the skilled person.

A synthetically made glycosylated form of an aroma aglvcon compound

The glycosylated form of an aroma aglycon compound shall be made synthetically (e.g. chemically or enzymatically). The art describes a number of ways to chemically make suitable glycosides. For making it enzymatically it is preferred to use of method contacting aglycon a glycosyltransferase or a glycosidase under suitable conditions to ensure proper functioning of the enzymatic process. This may be done in different manners.

The term "glycosyltransferase" denotes a glycosyltransferase capable of conjugating a sugar to an aglycon as described herein. If the sugar is glucose the glycosyltransferase may be termed a glucosyltransferase.

One way of doing it is in vitro where in e.g. a tube is present the aglycon and the glycosyltransferase or the glycosidase. Suitable conditions refer to adequate buffer solutions, temperature, time, etc. Based his common knowledge, the skilled person may routine identify such suitable conditions. A preferred way is in vivo in a fermented microorganism cell. A preferred in vivo method is described in details in WO2004/111254A1. Herein is also described how to find suitable glycosyltransferase and other related technical elements. Based on e.g. WO2004/111254Al and his common general knowledge the skilled person can make a glycosylated form of an aroma aglycon compound of interest.

Composition consisting essentially of synthetically made glycosides

It is clear that when one synthetically has made glycosylated form of an aroma aglycon compound one may get a glycoside composition consisting essentially of the synthetically made glycosides. Further this composition will be free from compounds originating from an extract of a natural plant.

The composition may also comprise suitable industrial acceptable carriers. The term "industrial acceptable carriers" as used herein is meant one or more compatible solid or liquid filler diluents, or encapsulating substances. By "compatible" as used herein is meant that the components of the composition are capable of being commingled without interacting in a manner which would substantially decrease the efficacy of the total composition under ordinary use situations.

The composition may be in any suitable form such as powder, suspension or solution. Flavor or fragrance formulation

The composition consisting essentially a synthetically made glycosylated form of an aroma aglycon compound as described herein is used to make a suitable flavor or fragrance formulation.

In fact the flavor or fragrance formulation may be identical to the composition consisting of the glycosides.

However, they may advantageously be added other ingredients to the flavor or fragrance formulation. In particular it may be preferred to incorporate other suitable aroma aglycon compounds into the formulation. These may be an aroma aglycon compound, wherein the aglycon (e.g. vanillin) is the aglycon of the corresponding glycosylated form of an aroma aglycon (e.g. vanillin glucoside). However it may also be different aroma aglycon compounds. This will depend on the desired flavor or fragrance profile of the product. Alternatively, the product may comprise aroma compounds originating from an extract of a natural plant.

The flavor or fragrance formulation may also comprise suitable industrial acceptable carriers.

The formulation may be in any suitable form such as powder, suspension or solution.

Aroma aglvcon compound

It is routine work for the skilled person to determine if a relevant aglycon compound is an aroma compound suitable for making a flavor composition as described herein.

Preferably, the aroma aglycon compound is a compound selected from the group of aroma compounds given in Annex I with title "CHEMICAL GROUPS FOR FLAVOURING SUBSTANCES" of the EU Commission Regulation (EC) No 1565/2000 of 18 July 2000 relating to flavoring substances used or intended for use in or on foodstuffs. Accordingly, in a preferred embodiment the aroma aglycon compound is a compound selected from the group of aroma compounds consisting of: 1. Straight-chain primary aliphatic alcohols/aldehydes/acids, acetals and esters with esters containing saturated alcohols and acetals containing saturated aldehydes. No aromatic or heteroaromatic moiety as a component of an ester or acetal;

2. Branched-chain primary aliphatic alcohols/aldehydes/acids, acetal and esters with esters containing branched-chain alcohols and acetals containing branched-chain aldehydes. No aromatic or heteroaromatic moiety as a component of an ester or acetal;

3. α, β-unsaturated (alkene or alkyne) straight-chain and branched-chain aliphatic primary alcohols/aldehydes/acids, acetals and esters with esters containing α, β-unsaturated alcohol and acetal containing α, β-unsaturated alcohols or aldehydes. No aromatic or heteroaromatic moiety as a component of an ester or acetal;

4. Non-conjugated and accumulated unsaturated straight-chain and branched-chain aliphatic primary alcohols/aldehydes/acids, acetals and esters with esters containing unsaturated alcohols and acetals containing unsaturated alcohols or aldehydes. No aromatic or heteroaromatic moiety as a component of an ester or acetal; 5. Saturated and unsaturated aliphatic secondary alcohols/ketones/ketals/esters with esters containing secondary alcohols. No aromatic or heteroaromatic moiety as a component of an ester or ketal;

6. Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols and esters with esters containing tertiary alcohols. Esters may contain any acid component; 7. Primary alicyclic saturated and unsaturated alcohols/aldehydes/acids/acetals/esters with esters containing alicyclic alcohols. Esters/acetals may contain aliphatic acyclic or alicylic acids or alcohol component;

8. Secondary alicyclic saturated and unsaturated alcohols/ketones/ketals/esters with ketals containing alicyclic alcohols or ketones and esters containing secondary alicyclic alcohols. Esters may contain aliphatic acyclic or alicyclic acid component;

9. Primary aliphatic saturated or unsaturated alcohols/aldehydes/acids/acetals/esters with a second primary, secondary or tertiary oxygenated functional group including aliphatic lactones;

10. Secondary aliphatic saturated or unsaturated alcohols/ketones/ketals/esters with a second secondary or tertiary oxygenated functional group;

11. Alicyclic and aromatic lactones;

12. Maltol derivatives and ketodioxane derivatives; 13. Furanones and tetrahydrofurfuryl derivatives;

14. Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms;

15. Phenyl ethyl alcohols, phenylacetic acids, related esters, phenoxyacetic acids and related esters;

16. Aliphatic and alicyclic ethers;

17. Propenylhydroxybenzenes;

18. Allylhydroxybenzenes;

19. Capsaicin related substances and related amides; 20. Aliphatic and aromatic mono- and di- thiols and mono-, di-, tri-, and polysulfides with or without additional oxygenated functional groups;

21. Aromatic ketones, secondary alcohols and related esters;

22. Aryl-substituted primary alcohol/aldehyde/acid/ester/acetal derivatives, including unsaturated ones; 23. Benzyl alcohols/aldehydes/acids/esters/acetals. Benzyl and benzoate esters included. May also contain aliphatic acyclic or alicyclic ester or acetal component;

24. Pyrazine derivatives;

25. Phenol derivatives containing ring-alkyl, ring-alkoxy, and side-chains with an oxygenated functional group; 26. Aromatic ethers including anisole derivatives;

27. Anthranilate derivatives;

28. Pyridine, pyrrole, and quinoline derivatives;

29. Thiazoles, thiophene, thiazoline and thienyl derivatives;

30. Miscellaneous substances; 31. Aliphatic and aromatic hydrocarbons;

32. Epoxides;

33. Aliphatic and aromatic amines; and

34. Amino acids.

Within the group above it is preferred that the aroma aglycon compound is a compound selected from the group of aroma compounds given in Part A with title "FLAVOURING SUBSTANCES" of the annex of the EU Commission Decision (2002/113/EC) of 23 January 2002 relating amending Commission Decision 1999/217/EC as regards the register of flavouring substances used in or on foodstuffs. The group of compounds given in Part A of this EU Decision is incorporate by reference herein.

In a further preferred embodiment the aroma aglycon compound is a compound selected from the group of aroma compounds consisting of:

alcohols such as aliphatic alcohols selected from the group consisting of: butanol, pentanol, 3- methyl-butanol, 3 -methyl- 1 -pentanol, 2-hexanol, 2-heptanol, undecanol, cis-3-hexenol, cis-6- nonenol, 2,6-nonadiene-l-ol, 9-decenol, geraniol, linalool, nerol, citronellol, hydroxycitronellol, myrcenol, 3,7-dimethyloctanol, iarnesol, nerolidol, perylalcohol, l-octen-3-ol and lavandulol;

cycloaliphatic alcohols selected from the group consisting of: menthol, terpineol, piperitol, perillyl alcohol, carveol, myrtenol, santalol, cedrol, patchouli alcohol, ionol, hydroxydimethylfuranone and hydroxydamascone;

aromatic alcohols selected from the group consisting of: benzyl alcohol, cumic alcohol, 2- phenylethyl alcohol, phenylpropyl alcohol, eugenol, guaiacol, 4-vinlylguaiacol and derivatives, hydroxyphenylbutanone, cinnamic alcohol, and [alpha] -amylcinnamic alcohol;

phenols selected from the group consisting of: eugenol, vanillin, ethyl vanillin, p- hydroxybenzaldehyde, anisalcohol, , vanillyl alcohol, piperonyl alcohol, and sesamol;

and

thiols selected from the group consisting of: methyl mercaptane, ethyl mercaptane, isopropyl mercaptane, propyl mercaptane, allyl mercaptane, thiogeraniol, thioterpineol, thiolinalool, thiomenthol , 4-methoxy-2-methyl-2-butanediol, l-p-methene-8-thiol (Grapefruit mercaptan), furfuryl mercaptan, 2-methyltetrahydroiuran-3 -thiol 3 mercaptohexyl hexanoate, 3 mercapto-1- hexanol and 3 mercapto-2-methylpentan-l-ol. Within the list above, it is preferred that the aroma aglycon compound is a compound selected from the group of aroma compounds consisting of:

aliphatic alcohols selected from the group consisting of: cis-3-hexenol;

cycloaliphatic alcohols selected from the group consisting of: hydroxydimethylfuranone;

aromatic alcohols selected from the group consisting of: hydroxyphenylbutanone and ethylpheylalcohol;

phenols selected from the group consisting of: vanillin and eugenol; and

thiols selected from the group consisting of: 4-methoxy-2-methyl-2-butanediol, l-p-methene-8- thiol (Grapefruit mercaptan).

In the most preferred embodiment the aroma aglycon compound is vanillin and the glycosylated form of an aroma aglycon compound is vanillin glucoside.

Preferably, the aroma aglycon compound is a low molecular weight organic aglycon compound that has a molecular weight from 50 to 3000. Preferably, the low molecular weight organic aglycon compound has a molecular weight from 50 to 2000, more preferably a molecular weight from 50 to 1000, and even more preferably a molecular weight from 50 to 750. The molecular weight is the mass of one molecule in atomic mass units.

The presenting invention is particularly suitable with respect to aroma aglycon compounds that have a very high flavor or fragrance impact even at very low concentrations, i.e. in the ppb range from 0.001 to 5. These compounds are often used as so-called "top notes" in flavor and fragrance formulations and have the distinct function to impair the desired flavor or fragrance. Being reactive and very volatile the industrial use of these compounds are know to be problematic. The use of glycosides of such compounds as described herein solves this problem. Accordingly, in the preferred embodiment the resulting product comprising the glycosylated form of the aroma aglycon compound as described herein is a product comprising the glycosylated form of the aroma aglycon compound in a very low concentration, i.e. in the ppb range from 0.001 to 50, more preferably in the ppb range from 0.001 to 10, even more preferably in the ppb range from 0.001 to 5 and most preferably in the ppb range from 0.001 to 2.

In a preferred embodiment, the low molecular weight organic aglycon compound is an alcohol. An alcohol should herein be understood in relation to the technical objective of glycosylating the aglycon. Accordingly an aglycon defined as an alcohol is herein a compound that contains a hydroxyl- (-OH) functional group that can be glycosylated synthetically (e.g. chemically or enzymatically). A non limiting example of a preferred aglycon compound which is an aromatic alcohol is vanillin.

In a preferred embodiment, the low molecular weight organic aglycon compound is a thiol (mercaptane). A thiol should herein be understood in relation to the technical objective of glycosylating the aglycon. Accordingly an aglycon defined as a thiol is herein a compound that contains a -SH functional group that can be glycosylated synthetically (e.g. chemically or enzymatically).

Plants may be seen as the organic chemists per excellence in nature. More than 200.000 different natural products are known from plants. These enable plants to deter herbivores and pests, attract pollinators, communicate with other plants and constantly adapt to climatic changes. These compounds may be termed secondary metabolites and a range of these are aroma compounds (e.g. vanillin).

The term "secondary metabolite" relates to that plants and microbes synthesize a large number of natural substances, in particular secondary metabolites, with diverse and generally unclear function. In contrast to the primary metabolites (eg amino acids, sugars, fatty acids), which are involved in fundamental functions like metabolism, growth, maintenance and survival, secondary metabolites are not required for fundamental functions. The term secondary metabolite should herein be understood in view of such, according to the art, standard description of the term. In a preferred embodiment the low molecular weight organic aglycon compound is a secondary metabolite compound, preferably a plant secondary metabolite compound.

EXAMPLES:

EXAMPLE 1 : Delay in the release of the aroma from vanillin glucoside compared to vanillin

In this example the taste release of vanillin and vanillin glucoside was compared organoleptic from a 100 ppm water solution and the taste panel found a distinct delay in the release of the aroma from vanillin glucoside compared to vanillin. In order words, the use of the vanillin glucoside gave a sustained release profile of the vanilla flavor.

The vanillin glucoside was made by the in vivo method described in WO2004/111254A1.

Vanillin aglycon was commercially available vanillin.

EXAMPLE 2: Improved water solubility of VG

At 30°C the solubility of vanillin glucoside in water was found to be app. 35 g/1 corresponding to 16.8 g/1 vanillin while the vanillin solubility was only app. 11 g/1, measured by HPLC.

EXAMPLE 3: Improved stability of vanillin glucoside.

The improved stability of vanillin glucoside may be determined as a comparison between vanillin glucoside (VG) and vanillin using the following parameters:

At 25°C storage with light and without light in water for 3 month and in alcohol for the same period (mimic flavor formulations in storage) measuring the concentration of vanillin and vanillin glucoside (HPLC or GC and run Head Space GC of the samples to identify by products) and smelling - tasting them. Concentration around 5 g/1 of vanillin and 10 g/1 of vanillin glucoside.

Measure vanillin and VG stability at 100 C in water after ¹A hour. Measuring vanillin and VG stability at pH 3, 7, 9 at 100 C after ¹A hour. Measuring vanillin and VG stability in ice cream after 3 month by tasting (using qualified taste panel).

EXAMPLE 4: An ice cream like oil — water emulsion with both vanillin and VG

An ice cream is made according to standard procedures. Three experimental samples is made:

(i) Test sample: vanillin and vanillin glucoside is added to get a 100 ppm flavor addition (vanillin equivalents) (ϋ) Vanillin glucoside is added to get a 100 ppm flavor addition (vanillin equivalent)

(ϋi) Control sample: only vanillin is added.

The ice cream is frozen and stored for 1 month. The samples are evaluated organoleptic after 48 hours, 14 days and 1 month.

A qualified taste panel finds that they can distinguish between the three samples in a double blind taste trial and that the combination gives a more uniformly distribution of taste

The taste panel is a qualified panel from the Royal Veterinary & Agricultural University (Denmark).

After 1 month storage the icecream samples are analyzed. The water phase comprises essentially all of the VG and the oil phase comprises essentially all of the vanillin. In the control emulsion (only comprising vanillin) there is essentially no vanillin in the water phase.

Claims

1. Use of a composition consisting essentially of a synthetically made glycosylated form of an aroma aglycon compound, wherein the composition is free from compounds originating from an extract of a natural plant, for making a flavor formulation and subsequent incorporation of the flavor formulation into a product selected from the group of products consisting of: (i) a food product selected from the group of food products consisting of: a dairy product; a water in oil emulsion such as margarine or butter; a oil in water emulsion such as an edible ice a sherbet or a sorbet; a confectionery; a cereal or cereal product; a dessert; a bakery ware; a foodstuff intended for particular nutritional uses; a non-alcoholic ('soft') beverage; alcoholic beverages, including alcohol-free and low-alcoholic counterparts; and Ready-to-eat savouries; (ϋ) feed products; resulting in a product comprising the glycosylated form of the aroma aglycon compound to give a suitable flavor.

2. Use of a composition consisting essentially of a synthetically made glycosylated form of an aroma aglycon compound, wherein the composition is free from compounds originating from an extract of a natural plant, for making a fragrance formulation and subsequent incorporation of the fragrance formulation into a product selected from the group of products consisting of:

3. The use of claims 1 or 2, wherein the glycosylated form of an aroma aglycon compound is a glucosylated form (i.e. the sugar is glucose) of an aroma aglycon.

4. The use of any of the preceding claims, wherein the glycosylated form of an aroma aglycon compound is enzymatically made by use of method comprising contacting aglycon a glycosyltransferase or a glycosidase under suitable conditions to ensure proper functioning of the enzymatic process to get the glycosylated form of an aroma aglycon compound.

5. The use of any of the preceding claims, wherein the resulting product is an oil in water emulsion product or a water in oil emulsion product wherein the product is comprising both glycosylated form of an aroma aglycon compound and aroma aglycon compound and wherein the water phase comprises glycosylated form of an aroma aglycon compound and the oil phase comprises aroma aglycon compound and wherein the water phase comprises from 85 to essentially 100% of the glycosylated form of the aroma aglycon compounds of the product and the oil phase comprises from 85 to essentially 100% of the aroma aglycon compounds of the product.

6. The use of claim 5, wherein the oil in water emulsion product or a water in oil emulsion product is a food product, in particular wherein the food product is an ice cream, a dressing, a dessert, a functional food product or an yellow fat.

7. The use of any of the preceding claims, wherein the product comprises a system to deglycosylating the glycosylated form of an aroma aglycon, in particular wherein it is done by use of an enzyme with beta-glycosidase activity and wherein from 50 to 100% of a specific aroma compound of the product are glycosylated form of the specific aroma aglycon compounds, such as for instance, a product comprising 3 times more vanillin glucoside than vanillin.

8. The use of claim 7, wherein the product is a non-alcoholic ('soft') beverage food product and the beverage comprises a system to deglycosylating the glycosylated form of an aroma aglycon, wherein the system is made in a way wherein the deglycosylating activity is first activated just before one starts to drink the soft beverage, e.g. be a system that liberates an enzyme with beta- glycosidase activity when one opens the cap of the soft beverage bottle.

9. The use of any of the preceding claims, wherein the aroma aglycon compound is a compound selected from the group of aroma compounds consisting of:

cycloaliphatic alcohols selected from the group consisting of: menthol, terpineol, piperitol, perillyl alcohol, carveol, myrtenol, santalol, cedrol, patchouli alcohol, ionol, hydroxydimethyliuranone and hydroxydamascone;

and

thiols selected from the group consisting of: methyl mercaptane, ethyl mercaptane, isopropyl mercaptane, propyl mercaptane, allyl mercaptane, thiogeraniol, thioteφineol, thiolinalool, thiomenthol , 4-methoxy-2-methyl-2-butanediol, l-p-methene-8-thiol (Grapefruit mercaptan), furfuryl mercaptan, 2-methyltetrahydroiuran-3 -thiol 3 mercaptohexyl hexanoate, 3 mercapto-1- hexanol and 3 mercapto-2-methylpentan-l-ol.

10. The use of any of the preceding claims, wherein the aroma aglycon compound is vanillin and the glycosylated form of an aroma aglycon compound is vanillin glucoside.