CS226176B2 - Method of producing beta-cyclodextrine inclusion complexes of natural odours and spieces - Google Patents

Abstract

ss-cyclodextrin inclusion complexes contain natural or synthetic flavouring and/or seasoning molecules as inclusions. These complexes can be prepared by reacting ss-cyclodextrin, in the form of a solution, with natural or synthetic flavourings and/or seasonings and/or with their solutions. Such complexes are used for the preparation of flavouring and/or seasoning preparations.

Description

It is an object of the present invention to provide a process for producing beta-cyclodextrin inclusion complexes of natural flavors and spices, as well as synthetic eromas.

Flavor and spices are important components of human food. It is typical for most foods that their quantity gradually decreases during storage and that the ratio of the individual components also adversely changes.

The following flavor-containing substances may be used to flavor or spice foods: natural raw materials, containing eroma, for example, kernels, plant parts, aromatic extracts or concetrates of natural raw materials, or synthetic flavor or solutions or emulsions thereof, or the abovementioned ends. aroma dispersed on the surface of a solid carrier, a bead or microcapsule of aromatic preparations, or a combination thereof.

Raw materials containing natural erome (mainly spices of vegetable origin) are widely distributed in human food. The shortcomings of using these spices are the following:

their preparation and processing requires a lot of work (eg peeling and crochet onion), the ingredients are not stable, the aroma content depends on the purchase, size, type and place of production, natural products generally cause microbiological impurities and often also parasitic impurities, active substances during storage, they cannot be changed, their traceability is limited, the natural carriers of some aromas are a significant storage problem (space requirement, optimum temperature, moisture content, etc.).

Liquid aroma extracts, concetretes, have long been known and sold. The problem most often arises in the fact that the decomposition of the bulk of the eropus is not prevented, but such preparations are still less stellar in the form of their concen- trates. Their use is widespread only to a limited extent and in only a few sectors of the food industry (for example, the canning industry).

In commercial food supply, in catering and in restaurants where large quantities of spices and aromas are used, only a vast amount of aromatic extracts, obsetraufcť spices are used to prepare flavor enhancing sauces, several meat dishes and salad fame. In small houses where small amounts are required, in practice no leachate is required.

The arena, dispersed on solid carriers, is preferred, but a large proportion of these are lost by leakage, oxidation or chemical decomposition.

Compatibility problems often arise with preparations that contain an arena in the form of an aqueous encapsulation. A pH that is unfavorable in terms of aroma or an aqueous medium can induce decomposition or hydrolysis of the aroma. Losses due to leakage or oxidation may be neglected in the case of picaocaastic preparations. Production technology ρΙ ^ το ^ ι ^! it is very costly, the highly volatile substances cannot be effectively processed into capsules and the arps will only collapse upon dissolution of the capsule wall, the corresponding release thus requires dissolution in warm water.

Thus, it is not necessary to ensure in the directly consumed food that the active ingredient contained in the pillocapsules in the mouth during the chewing process is released to a sufficient amount of less than 1 µM. The applicability of the aropptic preparations deposited in the pirokrocaine is therefore suggested.

OBJECT OF THE INVENTION was the production of arena and spices for industrial hospitality and for every kitchen, preparing foodstuffs which would not show any of the drawbacks of the previously used preparations and ingredients which would be long after. . . the flavor and flavor would not be lost during storage and would allow any flavor and greyhound to be combined.

Cycodetrins are cyclic compounds consisting of glycotidepyranothidoin units linked by glycosidic bonds of the alpha-1,4- type. The alpha-cyclonesextrta consists of 6 and the beta-cyclonesextrta from 7 glycopyrrolidine units. As a consequence of the structure of the glycopyranose units, the second hydroxy group is located at one edge of the ring and the first hydroxytaupine is located at the other edge of the ring, so that glycoside-hydrogen glycoside and hydrogen atoms are located in the cavity.

As a result, the cyclodextrin dissolves in water, but within the cavities are apolerative. Thus, it can be screened that when nooelkiles are added to an aqueous solution of cyclodeatrin, the shape, size and polarity of which show that these break down in the cyclodextrin cavity. (closed) confetti whose solubility is generally than that of so-called foreign pooekils. In this way, crystalline cyclodextrin noelkils can be produced.

According to the German Patent Specification No. 895,769, biologically active organic compounds (pentetDPeylintterizsl, hetachlorocyclohetane) can form slip complexes with cyclic from a saturated aqueous solution. In the description, the formation of a vanilla-cinnamic aldehyde assembly is reduced without data.

Swiss Patent No. 445,129 relates to the production of cyclodextrin polymers and the use of their complexing properties.

From the US patent. No. 3,452,635 has been known for the production of high molecular weight, water-insoluble cyclodextrin polymers and their use in obtaining melt flavor from coded water.

According to the US patent specification δ. No. 3,528,819, the bitter taste of coffee or tea extracts can be odraxitized by the addition of a low amount of beta-cyclodextrin.

83, 146 032 discloses a process for the production of a limonene-cyclodextrin inclusion complex, and C. A. 84, 20071e discloses a method by which an unpleasant taste of proteinhylase can be cyclized by cyclodextrin.

The compounds may be incorporated into the toothpaste to stabilize (U.S. Pat. No. 4,001,430). There is only a reference to moonoot in the description, according to which acacia gum can be substituted with cyclodextrin.

The stabilization of the aromatic substances by dextrin is described in U.S. Pat. No. 3,061,444. In addition, the volatile constituents and the juice of fruit, vegetables and broth are stabilized with a mixture of linear and tl-cyclodextria.

It has now surprisingly been found that aromas and spices extracted or synthesized from natural raw materials in a known manner can form complexes with the cyclodextron, thereby producing crystalline, stable, microfibre and difficult to digest or unstable fibers and parts. The flavor preparations in the form of instant powders or unit doses, for example in the form of tablets, can be obtained in a simple, well-dosed and long-storable manner, thereby obtaining, to the desired extent, aromatised foodstuffs using appropriate quantities.

Cyclodextrins are toxic starch derivatives that are either non-toxic or non-toxic and therefore non-toxic, or when the derivatives begin to produce a linear dextrio, which is a normal and largely consumed component of human food.

In addition, the aroma used in the ophthalmic industry, which has a molecular weight of about 80 to 250, is most suitable for forming the cyclodextrin occlusion complexes of the invention. Highly molecular substances, when these have an appropriately long formed side chain, which will find a place in the cavity. cyclodextrin.

SUMMARY OF THE INVENTION The present invention provides a process for the preparation of beta-cyclodextrin inclusion complexes of natural flavors or spices, as well as synthetic flavors, characterized in that the beta-cyclodextrio is preferably dissolved at 50 to 60 ° C in water, ethanol or a mixture thereof with vigorous stirring or shaking is reacted with natural or synthetic flavors and / or spices and / or solutions thereof, whereupon crystals and / or cooling precipitate from the solution crystals of the beta-cycloeettrinium inclusion complex of natural artefacts, synthetic aromas or spices which are separated, for example by filtration .

Kotnmp-exs are usually white, mita ^, ourkicelic powders whose particle size. between 5 ^{and 10} volume η ^ speiflclcý Chir ^{s p} r in ^two mers ^{of 5} cm ³ / g. When ^the leather generates a loss of 7.5 to 8% (loss consists of crystalline water). The ReeOrgenfracture powder diagram of the complex demonstrates the fact that the complex is formed, which differs from the beta-ckkloeextria diagram.

The complexes have no characteristic melting point, they decompose when heated at 200 ° C, cherekkeeittic for beta-cyclodextrio. Preperates are stable up to these temperatures, the aroma is lost only to a small extent.

The complexes are sparingly soluble in water at room temperature; solubility: 0.01 to 0.035 g / ml. The complexes are very stable in the air at room temperature, dry in the dry state, and can be stored without decomposing. The resistance against contact oxidation is Warbiurg's oxidation tests. The complexes are heat resistant, only 25 to 30% of the active compound content is lost in vacuum at 150 ° C and no component of pure volatile oils can be detected.

The formulation of the complexes preferably depends on the top whether it is a large-scale or a small-scale application. For large-scale consumption, powder formulations are preferably produced which are stored in a suitable container, dispensed in a dispenser to achieve the desired taste and aroma effect. For mellitusers, the complexes are formulated in dosage units, preferably tablets containing spices and flavor or a mixture of spices (combi). For mabs, the dosage units, e.g. tablets, sachets or capsules, are preferably produced which For example, in the case of an onion, the tablet contains the active ingredient of the onion.The adjuvants of the formulated products are preferably salts: (e.g. sodium chloride, potassium chloride, sodium (sodium chloride)). , organic polymers (e.g., sugar; amino acids such as non-potassium glutamate), and the products may contain, in addition to customary fillers and carriers, conventional lubricants of the type II-type. (stearin and stearates).

. Complexes as well as products obtained using (1 / nbis sander dosage unit). Generally, aroma substances have little typical flavor. In an aqueous environment,. · Especially in warm water, the release of aromatic substances from the complex is very intense and thus fragrance occurs.

The aromas in the complexes and products are determined by semi-quartz micromethods, thin layer chromatography and quantitative gas chromatography. Sensory quality assays can be carried out on foods or foods produced using the preparations of the invention.

The use of inclusion complexes according to the invention and preparations containing complexes has the following advantages:

Inclusion complexes or preparations containing complexes can generally be used in the food industry, for example in the canning industry, the meat industry, the bakery industry, the confectionery industry and the dairy industry, etc. For example, they can be used to aromolize instant soups or fillings in the meat industry. The bismuth impurities, their composition and the antisense effect are permanent, can be processed well into food, are stable and resistant to the environment. In bakery products, it is particularly advantageous that the loss of aroma during bakery technology is very slight and the aroma is only degraded in the finished product.

With the practical elimination of the processing of flavor-containing ingredients, natural, first of all rsstlOrmths of origin, the need for labor in commercial food supply and catering can be reduced, storage space can be saved, transportation is simpler and no storage losses . The choice of aroma and spices was increased by the use of complexes. Complexes with hygiene requirements. The preparations are particularly suitable for people on a diet who are not allowed to plant vegetable fiber food. Substances, erd’ma, will increase the choice of meals for dieters.

Kitchen technology is simplified in domPánootech and the choice of aromas and spices is enriched. Dosing units with varying aroma content (e.g. tablets) can be stored for a long time without the risk of altering the active ingredient content in a small space.

The oxygen stability of the complex is illustrated by the table below.

Lemon oil was dripped onto the filter paper and the cyclodextrin circ oil complex was placed in a Werburg flask and oxygen uptake, relative to 1 mg of lemon oil, was measured at 37 ° C as a function of time in a pure oxygen atmosphere.

Table

Oxygen absorption by lemon oil with a beta-cyclodextrin complex with lemon oil / 1mg lemon oil

Time (hours) tHH / mg citric oil μΐ of oxygen / mg citric oil included in the beta-cyclodextrin complex 25 8 2 50 20 May . 5 75 42 10 100 ALIGN! 55 12 125 68 13 150 · 76 13 175 86 14 200 98 16 225 110 16 250 116 17 300 »27 19 Dec 350 133 20 May

The stability of the complex was also proved by thermoenalytic tests. The differential thermoderiographic graph of lemon oil shows a sharp peak at 55 ° C, which means that the volatilization of lemon oil is already running at β at this temperature at a high speed and is virtually terminated at 100 ° C.

Bees-cycloddetrin shows a sharp peak only at 300 ° C, indicating a thermal decomposition of cycloddextrin. The differential thermal derivative of the lemon oil complex with beta-cyclodextrin shows a sharp peak at 268 ° C, that is to say, the decomposition of the complex and a new peak that becomes wide-ranging, which marks the beginning of the cyclodexirin decomposition.

An important overhead of the method of the invention and the use of the new preparations is a considerable labor saving and health-related compliance (not necessary, for example, in large-scale tarajet onions or rubbing garlic).

Other aspects of the invention may be inferred from the examples without limiting them.

A. Examples of complex production

Example 1

Kornmlex of onion oil and beta-cyclodextrin

100 g of .beta.-cycloid-4-yne are dissolved in 1800 ml of a 1: 3 mixture of ethanol and water with stirring at 50 DEG. A solution of 10 g of onion oil in 90 g of ethanol is then added dropwise. After this addition, the heating was switched off, the reaction vessel was carefully covered with clay foil and dry substance, and the reaction mixture was gradually cooled over 4 to 4.5 hours while stirring vigorously to room temperature.

The warm reaction mixture is placed in a refrigerator for 16 hours, filtered through a frit Grit and the complex crystals are air-dried until a constant humorosis is achieved. Yield: 93 g, aroma content: 10.3%.

Example 2

Dill oil complex with beta-cyclodextrin

100 g of .beta.-cyclodextrin is dissolved 2a under vigorous shaking at 50 ° C.

in 1,800 ml of a 1: 3 mixture of ethanol and water and add 10 g of dill oil and continue shaking., A white, crystalline substance precipitates due to progressive cooling. Shaking is continued at an unchanged intensity for 4 to 4.5 hours. The reaction mixture was then placed in a refrigerator overnight and filtered the next day through a frit G1. The mixture is dried until it is constant in air. Yield: 97.7 g, aroma content: 6.76%.

Example 3

Angelica oil complex with beta-cyclodextrin g of beta-cyclodextrin is dissolved with stirring at 50 ° C in 900 ml of 30% v / v ethanol at 50 ° C. A solution of 5.0 g angelica oil in 50 g ethanol was slowly added to the beta-cyclodextrin solution. The system becomes cloudy during the addition. The angelica oil complex with beta-cyclodextrin is excreted as a white crystalline solid. The heater is turned off and the system is slowly cooled over 4-5 hours with constant vigorous stirring.

The reaction mixture is kept in a refrigerator for 16 hours, then the crystalline product is separated from the mother liquor by centrifugation and finally air-dried. Yield! 46.2 g, eroma content: 8.12%.

Example 4

Complex of smoked ar dma and beta-cyclodextrin

Dissolve 100 g of beta-cyclodextrin with stirring at 50 ° C in 1800 ml of a 1: 3 mixture of ethanol and water, then add dropwise a solution of 12 g of fumosel (smoked aroma) in 60 g of diethyl ether. After the addition, the solution becomes cloudy and the first crystals of the inclusion complex are precipitated.

The reaction mixture was cooled in the usual manner for 4 to 4.5 hours with stirring and the mixture at 20 ° C and stirred no longer and stored in a refrigerator for 16 hours. The mixture containing the crystalline complexes is allowed to freeze and water is removed by vacuum sublimation (lyophilization). Yield: 89.0 g, Ardma content: 10.2%.

Example 5

The raspberry aroma-beta-cyclodextrin complex g of beta-cyclodextrin is dissolved from vigorous shaking at 50 ° C in 180 ml of 30% v / v ethanol. Thereafter, 1.2 g of aramidine are introduced into the beta-cyclodextrin solution and shaking is continued, while the reaction mixture is slowly cooled. The first crystals of the inclusion complex are deposited at 38-40 ° C. Shaking is continued for 4-5 hours, after which the system is placed in the refrigerator when it reaches room temperature.

The crystalline raspberry aroma-beta-cyclodextrin complex is separated from the mother liquor by centrifugation the following day. The product is dried until constant weight in air. Yield: 8.4 g, aroma content: 8.66%.

Example 6

Tarragon oil complex with beta-cyclodextrin

100 g of beta-cyclodextrin was dissolved in 1800 ml of a 1: 3 mixture of ethanol and water by heating and vigorous stirring, and a solution of 10.0 g of estregon oil in 100 ml of ethanol was added dropwise to the solution of beta-cyclodextrin. A rich, white precipitate is formed. After the addition, the heating was turned off and the system was cooled very slowly to room temperature while stirring vigorously. The mixture was kept in a refrigerator for 16 hours, frozen and lyophilized. Yield: 96.7 g, aroma content: 9.8%.

Example 7

Mustard oil complex with beta-cyclodextrin

Dissolve 100 g of beta-cyclodextrin at 50 ° C in 1800 ml of a 1: 3 mixture of ethanol and water. A solution of 8.80 g of mustard oil in 88 g of ethanol was then added with stirring. In the final phase of the addition, the first crystals of the inclusion complex are precipitated. The heating is turned off and the system is kept in a refrigerator for 16 hours and filtered through a frit G ^. The crystalline product is dried. Yield: 67.7 g, aroma content 12.5%.

Example

Complex of eugenol with beta-cyclodextrin

100 g of beta-cyclodextrin are dissolved in 1800 ml of 30% (v / v) ethanol with vigorous stirring at 50 ° C. A solution of 14.4 g of eugenol with 72 g of ether is added dropwise. After the addition, the heating is switched off and the system is gradually cooled to 20 ° C. The cooled reaction mixture was frozen and the solvent removed by lyophilization. Yield 98 g, eroline 11.1%.

Example 9

Marjoram oil complex with beta-cyclodextrin

Dissolve 50.0 g of beta-cyclodextrin with vigorous shaking at 50 ° C in a 1: 3 mixture of ethanol and water (900 ml). A solution of 5.2 g of marjoram oil in 52 g of ethanol was then added. The mixture was cooled to room temperature with shaking and stored in a refrigerator for 16 hours. The crystalline complex is filtered through a frit G G. The product is air dried until constant weight is obtained. Yield: 45.7 g, aroma content: 8.0%.

Example 10

Caraway oil complex with beta-cyclodextrin

A 30% suspension is prepared from 275 g of starch, which is greased at 120 ° C and cooled to 80 ° C and 0.2% by weight of alpha-amylase is added and the mixture is partially pre-hydrolyzed for 20 minutes. The hydrolyzate is sterilized and cooled to 80 ° C. 5 units / g starch-cyclodextrin-transglucosylase enzyme preparation are added, while 10 g of caraway oil dissolved in 100 g of ethanol are added. The conversion is continued for 2 to 7 days to achieve optimal yield of caraway oil-beta-cyclodextrin inclusion complex.

The crystalline complex formed is separated from the mother liquor by centrifugation. The crystalline product is dried to constant weight. Yield: 98.9 g, aroma content: 10.0%.

Example 11.

Complex of thyme oil with beta-cyclodextrin

100 g of beta-cyclodextrin are dissolved under vigorous stirring at 50 DEG C. in 1800 ml of ethanol and water 1: 3, and then a solution of 12 g of thyme oil in 60 g of diethyl ether is added dropwise with stirring to the solution of beta-cyclodextrin. Heating was turned off and the mixture was cooled to room temperature for 4 to 4.5 hours and the crystalline product was freeze-dried after freezing to recover. Yield: 91.7 g, aroma content: 9.78%.

Example 12

Lemon essential oil complex with beta-cyclodextrinep

Dissolve 5.5 g of beta-cyclodextrin at 50 ° C in 90 ml of a 1: 2 mixture of ethanol and water and add 0,61 g of lemon essential oil, diluted to 10 times the volume of ethenol, dropwise with stirring.

After the addition, the solution was cooled to room temperature over 4 to 4.5 hours. The desired product is excreted in crystalline form. In order to accelerate the precipitation, the reaction mixture is kept at 0 to 5 ° C for 12 hours, then the precipitate is filtered off and air-dried at piston temperature. 5.08 g of the desired complex is obtained. Lemon essential oil content: - 10,14%.

The lemon essential oil solution is preferably dripped slowly from the vigorous stirring into the system and the reaction mixture is preferably cooled. Preferably, a lemon essential oil is used which contains 3-6% of the alie-citral responsible for the odor and the total amount of 90% mono-er. One of the essential components of the lemon essential oil is bound in a complex ratio in the original ratio. composition of lemon essential oil. Thus, by using the complex, the same flavoring, spice-effect as with lemon essential oil alone can be achieved.

Example 13

Kooplee * blackberry essential oil with bete ~ cyclsdextrinep · \

5.50 g bnte-cyklsfnxtrinu dissolved under stirring at 50 ⁰ C in 90 ml of ethane-US kaleidoscope with water - 1: 2 -. and 0.52 g of lemon essential oil was added dropwise. After finishing-adding. the reaction mixture is cooled to a temperature of flux over 4 to 5 hours, - the precipitated complex is filtered off and dried. 5.3 g of the desired complex are obtained.

Example 14

The lemon essential oil s-bnte-cyclsfextrinep complex is available as in Example 13, with the difference that lye is freeze-dried after cooling. 5.8 g of the desired complex are obtained.

Ex-HaB ·? '

Complex - jasmine essential oil with beta-cyclsdextrin ..

^{3.0 g} of ^beta-cy klsfextriiu the extended ^P uutí at ^{- 50} ° C in ⁵⁴ ml of ethanol under ou ^d = 1: 2, and a permanent - pricking the přikele solution jasmine oil (Jasmin absolu 21117 / R Payann, The reaction mixture was cooled to room temperature over 5 hours and held at 0 ° C for 16 hours, after which it was filtered to dryness to give 2.7 g of crystalline complex. containing 8.9% jasmine oil.

Example 16

Complex of essential oil with beta-cyclodextrin

5.30 g of .beta.-cyclodextrin are dissolved in 98 ml of water at 50 DEG C., and 0.50 g of peppermate oil, diluted to ten times the volume of ethanol, are added dropwise with stirring. After the addition was complete, the reaction mixture was cooled to room temperature over 4-5 hours, kept at 0 ° C for 16 hours, filtered through a gas filter, and the precipitate air-dried.

5.4 g of complex are obtained. Peppermint oil content; 9.0%.

The same complex is also obtained when the peppermate oil is added to the beta-cyclodextrin solution at once without dilution and stirring is performed by shaking.

Example 17

Anis essential oil complex with beta-cyclodextrin g of beta-cyclodextrin is dissolved at 60 ° C in 182 ml of ethanol (30% by volume) with stirring, followed by the dropwise addition of 1.05 g of aniseed essential oil solution, diluted to 5-fold with ethanol. The reaction mixture was worked up as in Example 16. 9.7 g of the title product were obtained. Solubility at 20 ° C: 0.037 g / 100 ml.

The same complex is obtained when anise essential oil is added to the beta-cyclodextrin solution without dilution at once.

Example 18

Bergamot essential oil complex with beta-cyclodextrin

10.5 g of .beta.-cyclodextrin are dissolved at 50 DEG C. in a 1: 2 mixture of ethanol and water, and a solution of 1.10 g of bergamot essential oil (synthetic KHV), diluted ten-fold with ethanol, is added dropwise with vigorous stirring. The reaction mixture was further worked up as described in Example 16. 10.6 g of a crystalline complex containing 10.4% bergemot oil was obtained.

Particle size of the complex: 20 to 22%, specific volume: 2.5 cm 2 / g. Water solubility at 20 ° C = 0.025 g / 100 ml, at 40 ° C = 0.041 g / 100 ml, at 90 ° C = 0.080 g / 100 ml.

B. Examples of solutions for the production of dosage units or formulations in another form

Example 1 * Preparation of tablets of dill-beta-cyclodextrin inclusion complex g The dill-oil-beta-cyclodextrin inclusion complex produced according to Example 2 is mixed with 0.5 g of steerin and 100 g of sodium chloride (the stearin used complies with the PH regulations. Hg. VI). and sodium chloride corresponds to the purest analytical quality standards). The mixture obtained is compressed into tablets having a diameter of 8 mm, a height of 2.5 to 2.7 mm, an average weight of 200 mg and 5%. Abrasion resistance below 3%, strength 6.5 kg. Solubility: The tablet dissolves in 1 liter of 100 ° C warm water for 120 seconds. Packaging of the finished tablets can be carried out by known methods.

Example 2

Mustard flavoring powder

48% mustard oil inclusion complex with beta-cyclodextrin (active ingredient content; 10.7%), 1.3% by weight, estragenol inclusion complex with beta-cyclodextrin (active ingredient content 10.2%), 0.2% by weight , onion oil inclusion complex, β beta-cyclodextrin (active ingredient content: 10.0%), 6.5% by weight, eugenol inclusion complex with beta-cyclodextrin (active ingredient content 10.0%), 30% by weight, citric acid, 10% by weight, sugar, 3% by weight, salt, 1% by weight, pepper. The mixture thus produced can be stored indefinitely in a salt shaker and is, for example, suitable for seasoning sausages.

Example 3

An example for seasoning instant-soups

The cyclodextrin complexes described in the examples and similarly made with other arrays are also suitable for flavoring instant soups. Especially preferred is the applicability of otherwise liquid flavors in instant soup bags and it should be emphasized that no microbiological and parasitic impurities are introduced into the product with the spice. Smoked meat bean soup is prepared, for example, as follows: 5 g beans, 20 g wheat flour, 30 g milk sugar, 10 g salt, 10 g sodium glutamate, 10 g fat and 1 mg smoked aroma-cyclodextrin complex. '

C. Examples of use of the aroma complexes produced by the process of the invention to flavor hot and cold meals

I. Liptoz cheese (Korozott)

variation e) 10 servings sheep cheese 1.00 kg butter 0.20 kg salt 0.01 kg pepper 0.01 kg mustard 0.03 kg onion 0.05 kg caraway oil complex with beta-cyclodextrin .0,33 8

variation (b) is the same except that a mustard oil with a beta-cyclodextrin of 0.15 g and an onion complex with a beta-cyclodextrin of 0.15 g are used instead of mustard and onion.

Liptevsky cheese is produced by spreading the sheep cheese well with butter in a churning machine. Add pepper and spices according to two variations, premixed with butter. The mixture was allowed to stand in the refrigerator for 1 hour until use. The advantage of using complexes is that they do not have to be cleaned much, kitchen technology does not require so much handwork. Furthermore, the complexes are advantageous from a hygiene point of view, since the earthy onion does not stain the space and the caraway does not stain the finished goods.

II

2. Juice for lettuce salad salt sugar vinegar portions of cones

0.01 kg

3 © kg

0.10 kg estragon oil complex with beta-cyclodextrin

0.3 to 0.5 g dissolved in about 500 ml of water

Well-washed lettuce is placed in juice and left to stand and serve for a while.

This use of the complex illustrates only the possibility of varying different juices with similar spices. Furthermore, the complex is always to be used in an unchanged amount, whereby the fresh raw material cannot be obtained, the active ingredients of the dry raw material ar & a and decrease due to storage and the raw materials must be difficult to weigh before use and also cause substantial microscopic impurities.

3. Turnover hen serving hen vegetables green peas onion salt pepper butter flour parsley cream lemon juice

2,00 kg

0.20 kg

0,10 kg (canned)

0.05 kg

0,02 kg

0.01 kg

0.01 kg

0,10 kg bundle dl

0.05 kg of complex of angelic oil with beta-cyclodextrin 0.33 g

The hens are divided into small pieces, washed, feathered, placed in cold water and vegetables are cut into small pieces. The spices and onions are immersed in water in a linseed bag, the water is salted and the hens boil until soft.

A light roux of butter and parsley is made and added before the hen is completely softened. Add angelica oil complex with beta-cyclodextrin, mixed in sour cream (0.33 g per 10 portions). The food is boiled and then spiced with lemon juice. Finally, the canned green peas are mixed. The use of angelic oil brings the spices in line. The complex also promotes taste in this case.

4. Wild sauce with wild ragout portion of venison leg fat onion

Vegetables for salt soup

1.20 kg

0.15 kg

0.15 kg

0.20 kg

0,04 kg

bay leaf pepper 0.002 kg 0.002 kg cream 0.20 kg flour 0,10 kg lemons 0,10 kg mustard 0.05 kg sugar 0,03 kg cream 0,10 kg Thyme oil complex with beta-cyclodextriήep 0.3 · to 0.5 g

The split washed roe meso is mixed into a slightly roasted onion, roasted for a while and then poured over with roe deer stock, the skin and half suffocated under a lid. Dice soup vegetables are added. Before softening, it is mixed with a sour cream cream and boiled well. Thyme oil complex with beta-cyclodextrin (0.20-0.50 g per 10 µm) mixed with sour cream is then added. The complex used is perfectly suited to induce a savory game taste without the need to use a sparingly soluble wild spice whose aroma content is uncertain and whose preparations promote microbiological contamination.

5. Vegetables kale

10 servings Curly kale 2,00 kg potatoes 1,00 kg salt, 0,03 kg fat 0,10 kg flour 0,10 kg onion 0.05 kg pepper> 0.003 kg pepper 0.002 kg caraway oil complex with beta-cyclodextrinep 0,30 g garlic oil complex with beta-cyclodextrinep 0,30 g β-cyclodextrinep oil 0,30 g

The curly wax is cleaned, the broom is removed and the leaves are cut into pieces and washed. is repeatedly always in new water. The potatoes are also cleaned and washed and cut into small cubes. So much broth of coot is put in a suitable pot that when the cabbage is already boiled, there is still enough of the broth to thicken. When the broth is cooked, not cut pieces of cabbage are added and the broth is boiled.

When the broth is cooked, add salt and ground pepper and the cabbage is half-cooked. Then cut the sliced potatoes and cook. Prepare a light brown scoop in the yellow, mix the finely chopped onion with half-roasted e and stain with pepper before watering. Then the vegetables are dusted with a saucer. The vegetables are then mixed with the beta-cyclodextrio complex of spices in warm water, the vegetables are mandated and salted to taste.

The beta-cyclodectrin complexes used for seasoning vegetables are easy to process. Cleaning them with garlic can kill them and it is not necessary to spread the Maaorana. The spices according to the invention are immediately separated in vegetables and microscopic and macroscopic impurities, which are conventional spices, can be avoided.

5. Squid cake

Cook 0,50 kg of brothers, peel and crush. When the potatoes have cooled, they are mixed with 0.50 kg of semi-fat curd. Then 0.10 kg of granulated sugar, 0.04 kg of raisins, 0.04 kg of flour and 5 egg yolks are added and the mass is allowed to stand. Then add a dill oil-beta-cyclodextrin complex (0.6 g) to the cartridge. wherein the filling has been premixed with warm milk.

Meanwhile, the cake dough is prepared by mixing 0.24 kg of flour, 0.16 kg of powder, 0.08 kg of powdered sugar and 2 egg yolks. The dough is placed in the refrigerator. A cake leaf is prepared from 0.30 kg of dough and baked in an oven at 180 to 200 ° C.

The baked cake sheet is filled with the aid of a pre-filled mold, small bars, pencil thicknesses are formed from the remaining dough and laid on top in the shape of a grid.

The cake is baked in a 160 ° C oven for an hour. Doot is cut into slices of powdered sugar. The great advantage of using the dill oil-beta-cyclodextrin complex according to the invention lies in the hygiene and the fact that it is always easy to achieve the same taste effect. This makes it possible to eliminate dependence on the season and variations in the taste of the dill stored.

7. Meat pate

The meat pate can be produced in a known manner (the meat is well smothered and ground together with the rolls dipped in milk on a meat grinder and mixed with less than 4). Add 0.13% marjoram oil-beta-cyclodextrin complex (active substance content 10.0 58) and 0.015 55 onion oil-beta-cyclodextrin complex (active substance content: 10.0 -%) to the pate. The meat pate can be okooennt with pepper or pepper.

8. Raspberry Pudding Powder g of Digerized Starch, which otherwise serves as a pudding powder base, is found to contain 0.6% raspberry oil with beta-cyclodextrin (active ingredient content: 9.1%). It is advantageous to dye the pudding with a lawful raspberry dye.

The meals prepared according to the above recipe, the aromatized beta-cyclodextrin complex of the invention, were tested by a group of 30 members. The results of the tests are summarized in the following table:

Food

Qualification good or appropriate given% examining liptava cheese (variation a) 100 liptava cheese (variation b) 100 ham sandwiches * 89 lettuce 82 Erikasé from hen 96 wild - venison ragout sauce 100 curly kale 96 cheesecake _t 91 x Ham the sandwiches are prepared by dipping the ham slices for about 15 minutes in an aqueous stream of the smoked aroma and beta-cyclodextrin complex. In the meantime, the otherwise nonnachaeistic ham gained a distinctive smoked taste of smoked ham.

According to the previously mentioned or known technologies, the following meals are prepared according to the following recipes:

9. Sandwiches with Liptov cheese 10 servings sheep cheese butter sour cream salt onion pepper mustard cumin 0.20 kg 0.05 kg 0.05 kg 0,02 kg 0.001 kg 0.001 kg 0.001 kg 0.001 kg (1.34 g of caraway-cyclodextrin complex can be substituted) Sandwich bread 10 slices (1 slice = 30 g) 10. ham sandwiches 10 servings bread butter Ham cucumber salt complex fumesol with beta- -cyclodextrin 10 slices 0.05 kg 0.20 kg 0.05 kg 0.001 kg • 0.6 g 11. Lettuce with tarragon juice 10 servings lettuce sugar vinegar salt tarragon 5 heads 0.20 kg 0,10 kg 0,03 kg 0.01 kg e can not be substituted for 0.13 g of estregone e beta-cyclodextrin complex 12. Lettuce 10 servings lettuce sugar vinegar salt yogurt dill 3 heads 0.20 kg 0,10 kg 0,03 kg 1 glass 0.05 kg can be accredited 1.2 g dill complex with beta-cyclodextrin 13. Chicken salad 10 servings chicken btto potatoes btto cucumbers btto jeblke btto mayonnaise salt 1,00 kg 0.20 kg 0,10 kg 0.15 kg 0.20 kg 0,02 kg ♦

pepper mustard ‘

14. Macaroni in Milan pasta salt butter fat onion mushrooms smoked bacon pepper tomato puree rubbed cheese (trapista)

0.001 kg

0.001 kg can be fixed i

0.6 g of mustard-tert-cyclolextrin portion

1,00 kg

0,03 kg

0,02 kg

0.05 kg

0,04 kg

0,10 kg

0.25 kg can be replaced with white speck and 0.6 µl of fumasol beta-cyclodextrin complex

0.001 kg

0,40 kg,

0.20 kg

15. Meat loaf with brown sauce pork (well ground) beef (well ground) salt fat onion garlic pepper mmaorean bun eggs parsley flour tomato puree breadcrumbs brown sauce bones fat flour sugar soup vegetable celery onion garlic 'tomato puree mushrooms serving

0,60 kg

0.60. kg

0,03 kg

0,10 kg

0.08 kg can be dispensed with 0.6 g · onion-beta-cyclodextrin complex

0.08 kg can be replaced by 0.13 g of garlic-beta-cyclodextrin complex

0.001 kg

0.001 kg can be π. ^^^

0.13 g of marjoram complex with beta-cyclodextrin

0.15 kg

0.12 kg bundle

0,30 kg

0,30 kg.

0,10 kg servings

1,00 kg

0,10 kg

0.15 kg.

0,02 kg

0,25 kg

0,06 kg

0.06 kg may not adhere

0.5 g of onion-beta-cyclodextrin complex

0.01 kg can be replaced by 0.13 g of garlic-beta-cyclodextrin complex

0.01 kg

0, ^ 1 kg red wine salt pepper bay leaf thyme

0.20 kg

0,02 kg

0.001 kg

0.001 kg

0.001 kg may not be substituted with thyme dextrin 0.13 g with beta-cycloVegetables © cabbage curly cabbage potatoes salt 'fat flour onionle garlic pepper ⁴ pepper caraway portions

2.00 kg 1, 00 kg 0.03 kg 0.10 kg 0.15 kg 0.05 kg can be replaced. 0.5

onion complex with beta-cycloxysine

0.01 kg can be replaced by 0.13 g of garlic complex with beta-cyclodextrin

0.003 kg

0.002 kg

0.002 kg may be replaced by a caraway-beta-cyclodietrin complex

17. Gil steak with dill and dill portions pork (chop) oil salt butter dill mustard

18. Cheese cake

1.20 kg

0.1 kg

0,02 kg

0.15 · kg

0.05 kg can be replaced by 0.2 g of dill-beta-cycloxtrinine complex

0.01 kg can be replaced with 0.16 g of mustard-beta-cyclodextrin complex slices: 1 slice = 1 serving

Dough:

flour 0.24 kg has the word 0.16 kg powdered sugar 0.08 kg egg yolks 2 incomplete N & Fill: raisins 0.04 kg curd 0.50 kg potatoes 0.50 kg sugar 0.10 kg flour 0.04 kg vanilla 0.01 kg peel of lemon 0.001 kg dill 0.05 kg can be

eggs , . replace 0.2 g of the dill-beta-cycloxtrin complex

E. Examples of solving problems of manufacturing dosage units, or questions of other formulations or flavoring

Filling powders suitable for seasoning meals may have the following composition.

1. Inclusive dill essential oil complex with beta-cyclodextrin salt

Aerosil 200

5.0 g

94.9 g

OJ g

10'0,0 g

2. Onion essential oil inclusion complex with beta- -cyclodextrnnem 2.0. G salt 97.95 G Aeroosi 200 0.05 G

100,00 _g 3. inclusion complex of ether-essential oil s.brta-cyclodrxtrnnee 20,0 kg salt 78.0 kg Ae ^OH 200 2,00 g 100,00 _g 4. inclusion complex of mmjorán essential oil with beta-cyclsdextrin 20,0 g lactose 79,0 g Ae ^OH 200 1,0 & 100.0 g

5. eugenol inclusion complex with beta- -cyclsdextrinne seharose AeeOH 200 20,0 g 79,5 g 0.5 g 100.0 g 6. Raspberry essential oil inclusion complex with beta-cycle. odextrn ne m 40,0 g ikrob 5e, 0g Ae ^ oH 200 · 2,0 g 100.0 g

7. Inmes complex with beta-cyclodextrin inclusion complex Garlic essential oil with beta-cyclodextrine inclusion complex Onion essential oil inclusion complex with beta-cyclodextrin salt

0.100 6 _g

0.166 9 _g

0.083 8 g

99.648 7 _g

8. Inclusion complex -cyclodextrin inclusion complex -cyclodextrin inclusion complex -cyclodextrin inclusion complex -cyclodextrin fumasole with betecibulum essential oil with betecibulum essential oil with betaacminine essential oil with beta0,100 5 g

0.166 4 g

0.083 7 g

666 6 g salt

97, 982 8 g

9. Funasol inclusion complex with beta-cyclodextrin Garlic essential oil with bete-cyclodextrin inclusion complex Onion essential oil with beta-cyclodextrin inclusion complex of mejorine essential oil with beta-cyclodextine salt

10. Fumasol inclusion complex with beta-cyclodextrin Garlic essential oil inclusion complex with bete-cyclodextrin Onion essential oil inclusion complex with bete-cyclodextrin inclusion complex of thyme essential oil with beta-cycloxysilate salt

0.100 4 g

0.166 4 g

0.083 8 g> 667 2 g

97.982 2 g

0.100 6 g

0.167 2 g

0.083 6 g

0.067 2 g

99.581 4 g

In order to better spray the powder of the mixture, a water-insoluble, inert substance may be admixed with the mixture; -Aeros !! 200. The tendency of the lump powder composition to form lumps depends not on the water or moisture content of the air.

In this case, the amount of α-L, lectose, secherose or starch will, of course, change accordingly in another direction.

The recovered mixture of mixtures

e) - A mixture of tea with jasmine fragrance

100 kg of the mixture is suitable for the filter formulation and suitable mmOs. The mixture of jasmine essential oil and beta-cycloxtron (produced according to Example 15) is carefully homodized in the mixing drum and the resulting mixture is filled into a conventional bag with a packing machine. The sachet contains 2 g of the tea mixture.

The jasmine essential oil complex with beta-cyclodextrin, used for eromaetzzec, is traded in the medicament, if it is an aroppelzec, or hermonnite. According to the composition of the art, it is more desirable that the mixture comprises 0.7% of a complex of jasmine oil with a beta-cyclodextrin (i.e. equivalent to a 0.07% of jasmine oil). This means not the beginning of 0.7 kg of copplex. '

b) Mixture of tea with bergemot oil

100 kg of tea for use in the filter formulation is de-acidifying. The bergemot oil complex with brtl-cycloextronP, produced according to Example 18 ', is carefully expanded in a mixing drum. The obtained mixture is filled with a bleach filling machine into filter bags. The sachet contains 2 g of sPs ^ L.

According to sensory qualifications, the best eoomization can be achieved with a 5% bergemot essential oil complex with brecycloxytronepeptide. This corresponds to 0.5% bergamot oil content.

c) A tea blend with a fragrance.

100 kg of the blend suitable for the filtration formulation and the beta-cycloalkylene glycol essential oil complex prepared according to Examples 12, 13, 14 are mixed in a mixing drum. According to the sensory agent, the best blend can be considered a blend containing 15% of the lemon essential oil complex with beta-cyclodextron.

d) tea blend with chasuble essential oil

100 kg of the tea blend suitable for the filter formulation and the corresponding amount of the peppermeter complex produced according to Example 16 are carefully mixed in a mixing drum. The favorable content of the complex is according to the sensoromeeric qualification 3 ».

The formulation of the mixtures in the case of mixture c) or d) is preferably carried out in sachets.

e) Aniseed tea blend.

100 kg of tea formulations suitable for the formulation are mixed in an above-described manner with the aniseed essential oil / ioctyl dextrin complex produced according to Example 17. According to sensometric tests, the best odor effect is obtained by adding 2% of the aniseed essential oil complex with beta-cyclodextrin.

The flavored tea blend (examples a to e) was stored in filter bags for one year in a paper box and after one year tea was brewed from the tea blends. According to sensomeeric tests, annual storage did not affect the smell of tea. ..

Claims (12)

SUBJECT OF THE INVENTION 1. A process for the preparation of? -Cyclodextrinol inclusion complexes of natural flavorings and spices, as well as of synthetic aromas, is obtained by dissolving the ether-cyclodextrin, preferably at 50 to 60 ° C, in water, ethanol or a mixture thereof. of the mixture and, with vigorous stirring or shaking, reacted with natural or synthetic erosions and / or spices and / or solutions thereof, then standing and / or cooling to precipitate the reaction solution with crystals of the inclusion complex of natural or syrupic flavors or spices with beta-cyclodextrin. which are separated, for example by filtration. 2. The process according to claim 1, characterized in that onion oil is used as a natural or synthetic aroma and / or spice. 3. The method according to claim 1, which comprises ma and / or spices, uses dill oil. 4. The method of item 1, wherein angel oil is used and / or the spice is used. 5. The process of step I, wherein fumasol is used and / or the spice is used. 6. The method of clause 1, using the raspberry flavor. 7. The method of item 1, wherein the lysate and / or the spice is a tarragon oil. 8. The process according to claim 1, wherein the mustard oil is used. 9. The method of claim 1 wherein the ma and / or spices are eugenol. by being like natural or synthetic erotica, being like natural or synthetic erotica, being like natural or synthetic sympathetic, getting like natural or synthetic rubbing, getting like natural or synthetic erosion getting like natural or synthetic brooches like natural or synthetic 10. The method according to claim 1, wherein the / or spices are used in a tomato essential oil. that is natural or synthetic 11. The method according to claim 1, wherein the cumin is used for caraway. by being like natural or synthetic f srome 12. The method of item 1, wherein the ginning and / or spices are used. thymiene essential oil. that is natural or synthetic f arSeverografia, n. p., MOST Price 2,40 Kčs