WO2002001967A2

WO2002001967A2 - Flavouring compositions

Info

Publication number: WO2002001967A2
Application number: PCT/EP2001/005252
Authority: WO
Inventors: John Stewart Tandy; Henry Kim; Dominick Damiano
Original assignee: Societe Des Produits Nestle S.A.
Priority date: 2000-06-30
Filing date: 2001-05-08
Publication date: 2002-01-10
Also published as: AU2001265937A1; WO2002001967A3

Abstract

An encapsulated flavourant based on a reaction product of aldehyde, ammonia, and sulfide entrapped in a cyclodextrin.

Description

FLAVOURING COMPOSITIONS

FIELD OF THE INVENTION

The present invention relates to flavouring compositions and more particularly to flavourants based on reaction products encapsulated in a cyclodextrin and foodstuffs containing them.

BACKGROUND OF THE INVENTION

Reaction products of alka-2,4-dienals are sticky, putty-like materials which are difficult to isolate and which are insoluble in water, ethanol, ethyl acetate, or other edible food solvents, and for all purposes are impractical or impossible to work with for flavors or foodstuffs. The products are so viscous and unmanageable that their use in foodstuffs as flavorants is extremely limited.

US patents 4,200,741 and 4,259,507 describe the preparation of shorter chain or branched chain dithiazines for use as flavourants but the purification of these flavourants involves tedious separations of organic and aqueous phases .

We have found that by encapsulating certain flavourants based on reaction products of aldehyde, ammonia, and sulfide in a cyclodextrin, the preparation and drying may be carried out easily while the tedious separations of organic and aqueous phases may be eliminated. SUMMARY OF THE INVENTION

According to the present invention there is provided an encapsulated flavourant based on a reaction product of aldehyde, ammonia, and sulfide entrapped in ^' a cyclodextrin.

DETAILED DESCRIPTION OF THE INVENTION

The aldehyde may be prepared from an alkanal, alk-2- enal , or an alka-2, 4-dienal, e.g. trans, trans-alka-2, 4- dien-1-al or trans, cis-alka-2,4-dien-l-al .

The aldehyde may contain from 3 to 20 carbons.

The ammonia and sulfide can be added as such, e.g. ammonium sulfide, or aqueous solutions of ammonia and hydrogen or sodium sulfide, or they may be obtained from precursors known in the art, such as cysteine, cys ine, thiamine, methionine, or from plants such as Brassica sp., corn, etc. Amine can be obtained from amino acids, ammonia salts, etc.

The reaction product may be a long chain thiophene, pyridine, a substituted long chain dithiazine, a long chain trithiane or trithiolane, or any mixture thereof.

The cyclodextrin may be, for example, an alpha-, beta-, or gamma-cyclodextrin.

The use of a cycoldextrin permits a simple commercially feasible process for entrapment, reaction, and conversion to powder form of these reaction products. The amount of the reaction product in the flavourant may vary from 0.1 to 50%, preferably from 1.0 to 35%, and more preferably from 2.5 to 20% by weight based on the weight of dry flavourant. The cyclodextrin forms substantially the remainder of the flavourant.

Many of these reaction products themselves have not been described from an organoleptic standpoint in the literature. Many of these products have extremely desirable meaty, fishy, and roasted fat character which impart characteristic flavor profiles to flavorings and foodstuffs.

We have found that alpha-, beta-, or gamma- cyclodextrins can be used to disperse and entrap alkanals, alk-2-enals, or alka-2,4-dienals, or mixtures thereof, and still allow reactions of the aldehyde group to occur with ammonia and sulfide. Further, the cyclodextrins entrap but do not hinder ring closure of the reacted aldehyde to the desired compounds formed from these reactions, such as short and long chain thiophenes and pyridines .

The present invention also provides a process for the preparation of a flavourant based on a reaction product of aldehyde, ammonia, and sulfide which comprises mixing the aldehyde, ammonia, and sulfide with a solution of a cyclodextrin.

The solution of cyclodextrin is conveniently an aqueous solution. The concentration of the solution of cyclodextrin may be from 5 to 50%, preferably from 10 to 30% and more preferably from 15 to 25% by weight based on the weight of the solution. The mixture of ingredients is conveniently agitated, e.g. by stirring, for example 5 to 500 rpm, centrifugation, or shaking. The agitation may be carried out over a period of from 0.5 to 24 hours, preferably from 3 to 12 hours .

Conveniently, the aldehyde is added to the solution of cyclodextrin followed by the ammonia and sulfide, although the order of addition is not critical. The alpha-, beta-, or gamma-cyclodextrins are preferably first dispersed in water until soluble. The alkanals, alkenals, alkadienals, or mixtures thereof may then be added to the cyclodextrin solution and mixed until a homogeneous solution is obtained. Ammonia and sulfide may then be gradually added to the aldehydes. The ammonia and sulfide can be added to a cold solution of the cyclodextrins, e.g. from -10°C to +10°C, or at higher temperatures, e.g. up to 50°C or more, although lower temperatures offer advantages in reduced odor and reduced loss of the volatile reactants . After the solution becomes homogeneous and creamy the reaction mixture is then dried.

The reaction is preferably carried out at low temperatures, e.g. from -5°C to +5°C.

Following the reaction, the mixture may then be conveniently dried by conventional means, such as freeze-drying or spray-drying, and ground to fine powders .

These powders are very easy to handle and can be re- solublized in water, ethanol, or other solvents such as triglycerides, or dry blended with dehydrated flavor blends, thus virtually eliminating the difficulties mentioned above in flavor or food usage. Further, reaction products of alkanals, alk-2-enals, or alkadienals or mixtures thereof, can be added to cyclodextrin solutions to facilitate entrapment of the reaction products. The cyclodextrin solutions can then be dried by conventional means such as freeze-drying or spray-drying.

However the preferred embodiment is to entrap the aldehydes on cyclodextrins first, followed by reactions with ammonia and sulfide.

The reacted products have roasted, fried, sauted, or grilled fatty, meaty, or onion-garlic flavor profiles and can be used to impart such character to flavors or foodstuffs .

Freeze-drying or air drying can be used without addition of any other encapsulating/entrapping agents . If spray-dried, small amounts of maltodextrin, gum acacia, corn syrup solids, modified food starches, or other carriers well known in the industry can be added to facilitate volatile retention or ease of powder handling after drying. Further, other flavoring agents or flavor chemicals can be added after the ammonia and sulfide reaction is complete and co-dried with the reacted aldehydes .

If freeze drying, vacuum drying, or drum drying Is used as the dehydration method the resulting bulk flaky material can be ground by any conventional means to obtain a powder. Spray dried products are typically powders .

The invention enables the creation of concentrated reaction products of aldehydes, ammonia, and sulfide, specifically alkanals, alk-2-enals, or more specifically alka-2, 4-dienals, or mixtures thereof, for use in flavorings and foodstuf s . The amount of flavourant in the foodstuff may be from 1 to 1000 ppm, preferably from 25 to 250 ppm, and more often from 50- 100 ppm.

EXAMPLES

The following Examples further illustrate the present invention. Parts and percentages are by weight.

Example 1

94 parts of gamma-cyclodextrin were dissolved in 532 parts of tap water in a vessel fitted with a stirrer and agitated at 300 RPM. The vessel was then submerged in an ice bath and 10.0 parts of trans, trans-2,4- nonadienal . After 10 minutes, 25 parts of a 20% solution of ammonium sulfide were added slowly over 10 minutes with stirring. The stirring was continued for 12 hours, during which time a mixture of 2- pentylthiophene and 2-butylpyridine were formed. The flavourant was was then freeze-dried and ground to a homogeneous powder which was found to have a roasted fat flavour.

Examples 2-7

By following a similar procedure to that described in Example 1, but using' the aldehydes listed in the following Table I, homogeneous powders were obtained having meaty, roasted fat, and slightly fruity flavours . TABLE I

Example 8

A similar experiment as Example 1 was followed, except that a blend of 2.5 parts of trans, trans-2,4-nonadien- 1-al and 7.5 parts isovaleraldehyde were added and reacted with 25 parts of a 20% solution of ammonium sulfide. A product with strong roasted bacon, roasted fat, toasted notes was obtained.

Example 9

A similar experiment as Example 1 was followed, except that 10 parts of a 20% ammonium sulfide solution and 15 parts of a sodium sulfide solution were added after addition of the aldehyde. A product with stronger toasted, burnt fat notes than the product of Example 1 was obtained.

Example 10

A mixture of 3.5 parts isovaleraldehyde and 6.5 parts of acetaldehyde were used in place of the aldehyde used in Example 10. A strong wild game or mutton product was obtained.

Claims

1. An encapsulated flavourant based on a reaction product of aldehyde, ammonia, and sulfide entrapped in a cyclodextrin.

2. An encapsulated flavourant according to claim 1 wherein the aldehyde is prepared from an alkanal, alk- 2-enal, or an alka-2,4-dienal .

3. An encapsulated flavourant according to claim 1 wherein the aldehyde is prepared from trans, trans- alka-2, 4-dien-l-al or trans, cis-alka-2, 4-dien-l-al .

4. An encapsulated flavourant according to claim 1 wherein the aldehyde contains from 3 to 20 carbons.

5. An encapsulated flavourant according to claim 1 wherein the ammonia and sulfide are added as ammonium sulfide or aqueous solutions of ammonia and hydrogen or sodium sulfide.

6. An encapsulated flavourant according to claim 1 wherein the ammonia and sulfide are obtained from cysteine, cystine, thiamine, methionine, or from plants .

7. An encapsulated flavourant according to claim 1 wherein the reaction product is a long chain thiophene, pyridine, a substituted long chain dithiazine, a long chain trithiane or trithiolane, or any mixture thereof.

8. An encapsulated flavourant according to claim 1 wherein the reaction product is concentrated for its use in flavorings and foodstuffs .

9. An encapsulated flavourant according to claim 1 wherein the cyclodextrin is an alpha-, beta-, or gamma-cyclodextrin.

10. An encapsulated flavourant according to claim 1 wherein the amount of the reaction product in the flavourant is from 1 to 50% by weight based on the weight of dry flavourant .

11. An encapsulated flavourant according to claim 10 wherein the cyclodextrin forms the remainder of the flavourant .

12. A process for the preparation of a flavourant based on a reaction product of aldehyde, ammonia, and sulfide which comprises mixing the aldehyde, ammonia, and sulfide with a solution of a cyclodextrin.

13. A process according to claim 12 wherein the concentration of the solution of cyclodextrin is from 5 to 50% by weight based on the weight of the solution.

14. A process according to claim 12 wherein the mixture of ingredients is agitated over a period of from 0.5 to 24 hours.

15. A process according to claim 12 wherein the reaction is carried out at a temperature from -10° to +10°C.

16. A foodstuff containing an effective flavouring amount of an encapsulated flavourant according to claim 1.