CN101641118A - Cyclodextrin inclusion complexes and methods of preparing same - Google Patents

Abstract

The present invention provides a product comprising a guest complexed with a cyclodetrin wherein the guest is more stable in the product and does not degrade as quickly as a product comprising the same guest without a cyclodextrin. In addition, the present invention provides a method of stabilizing guests with a cylodextrin and reducing the formation of guest degradation products.

Description

By preparation cyclodextrin inclusion complexes and preparation method thereof

The cross reference of related application

The application requires the U. S. application Serial No.60/877 in December in 2006 submission on the 27th, the U. S. application Serial No.60/877 of 489 and 2006 on Decembers submission in 27,, and 463 priority adds them by reference at this.

Background technology

Following U.S. Patent No. discloses the purposes that cyclodextrin is used for compound various guest molecules, incorporates at this following by reference full content: the U.S. Patent No. 4,296 of Borden, 137,4,296,138 and 4,348,416 (seasoning materials that are used for chewing gum, dentifrice, cosmetics etc.); 4,265,779 (foams in hibitors in the composition of detergent) of Gandolfo etc.; 3,816,393 and 4,054,736 (as the prostaglandins of medicine) of Hyashi etc.; 3,846,551 (parasite killing and the miticide compositions) of Mifune etc.; 4,024,223 (menthol, the methyl salicylate etc.) of Noda etc.; 4,073,931 (nitroglycerin) of Akito etc.; 4,228,160 (indomethacins) of Szjetli etc.; 4,247,535 (complement inhibitors) of Bernstein etc.; 4,268,501 (the Zhichuan activating agents) of Kawamura etc.; 4,365,061 (the inorganic acid complex) of Szjetli etc.; 4,371,673 (retinoides) of Pitha; 4,380,626 (the hormones plant growth regulators) of Szjetli etc.; 4,438,106 (long-chain fatty acid that can be used for cholesterol reducing) of Wagu etc.; 4,474,822 (the theine complex) of Sato etc.; 4,529,608 (the Mel spice) of Szjetli etc.; 4,547,365 (the hair waving activated complexs) of Kuno etc.; 4,596,795 (gonadal hormone) of Pitha; 4,616,008 (antibiotic complex) of Hirai etc.; 4,636,343 (the insecticide complex) of Shibanai; 4,663,316 (antibiotic) of Ninger etc.; 4,675,395 (chamenols) of Fukazawa etc.; 4,732,759 and 4,728,510 (the shower additives) of Shibanai etc.; 4,751,095 (aspartame) of Karl etc.; 4,560,571 (coffee-extracts); 4,632,832 (instant emulsion forms powder) of Okonogi etc.; 5,571,782,5,660,845 and 5,635,238 (spice, flavoring agent and the medicine) of Trinh etc.; 4,548,811 (the hair waving lotions) of Kubo etc.; 6,287,603 (spice, flavoring agent and the medicines) of Prasad etc.; 4,906,488 (the smelling flavor regulator (olfactant), flavoring agent, medicine and insecticide) of Pera; 6,638,557 (fish oil) with Qi etc.

Further described cyclodextrin in the following publication, these publications are incorporated herein by reference: (1) Reineccius, T.A. etc., " Encapsulation of Flavors using cyclodextrins:comparisonof Flavor retention in alpha; beta, and gamma types. " Journal of Food Science.2002; 67 (9): 3271-3279; (2) Shiga, H. etc., " Flavor encapsulation and releasecharacteristics of spray-dried powder by the blended encapsulant of cyclodextrinand gum arabic. " Marcel Dekker, Incl., www.dekker.com.2001; (3) Szente L. etc., " Molecular Encapsulation of Natural and Synthetic Coffee Flavor with β-cyclodextrin. " Journal of Food Science.1986; 51 (4): 1024-1027; (4) Reineccius, G.A. etc., " Encapsulation of Artificial Flavors by β-cyclodextrin. " Perfumer﹠amp; Flavorist (ISSN 0272-2666) An Allured Publication.1986:11 (4): 2-6; (5) Bhandari, B.R. etc., " Encapsulation of lemon oil by paste method using β-cyclodextrin:encapsulation efficiency and profile of oil volatiles. " J.Agric.Food Chem.1999; 47:5194-5197.

Summary of the invention

The invention provides a kind of product that contains with compound object of cyclodextrin and object catabolite, its object was at least about 5: 1 with object catabolite ratio when described product stored at least about 30 days under at least about 88 temperature.

The present invention also provides a kind of product that contains with the compound object of cyclodextrin, and the concentration of object in described product reduces and is no more than about 25% when wherein storing about 30 days under at least about 88 temperature.

In addition, the invention provides a kind of product that contains with the compound object of cyclodextrin, the concentration of wherein said object reduces in time, and wherein after about 30 days the concentration of described object in described product be lower than the concentration of described object in contrast and reduce.

In addition, the invention provides a kind of product that contains with compound object of cyclodextrin and object catabolite, wherein the concentration that exists at described object catabolite after about 30 days is lower than the concentration of described object catabolite in contrast after about 30 days.

The present invention also provides a kind of product that contains with compound object of cyclodextrin and object catabolite, wherein compares with the formation of object catabolite in contrast, and the formation of described object catabolite is reduced by at least about 200%.

The invention provides a kind of product that contains polyunsaturated fatty acid and cyclodextrin, wherein said polyunsaturated fatty acid and described cyclodextrin are compound.

In addition, the invention provides that a kind of object that reduces in the product is passed in time and the method for degrading, described method comprises and will be added in the described product with the compound object of cyclodextrin, wherein said object is compound with cyclodextrin in the presence of emulsifying agent, and wherein compared with the control, the degraded of described object is owing to the compound of described object and cyclodextrin reduces about 25%.

In addition, the invention provides a kind of minimizing and pass the method that the concentration of object in product reduces in time, described method comprises: will be added in the described product with the compound object of cyclodextrin, wherein compared with the control, the concentration of described object reduces owing to the compound of described object and cyclodextrin is reduced by at least about 25%.

The present invention also provides the method for the stability of the flavoring agent that a kind of improvement is exposed to the light time product, and described method comprises and will be added in the described product with the compound object of cyclodextrin that wherein compared with the control, the improved stability of described flavoring agent is at least about 25%.

Other features of the present invention and aspect will become clear after having considered detailed description and accompanying drawing.

Description of drawings

Fig. 1 is the sketch map with the guest molecule that holds in the cyclodextrin molecular of cavity and the cavity.

Fig. 2 is the cyclodextrin molecular of self assembly and the sketch map of the nanostructured that guest molecule forms.

Fig. 3 is the sketch map of the formation of diacetyl-cyclodextrin inclusion complexes.

Fig. 4 is the cyclodextrin molecular of self assembly and the sketch map of the nanostructured that the diacetyl molecule forms.

Fig. 5 is the sketch map of the formation of citral-cyclodextrin inclusion complexes.

Fig. 6 is the cyclodextrin molecular of self assembly and the sketch map of the nanostructured that the citral molecule forms.

Fig. 7 illustrates the degradation mechanism of citral.

Fig. 7 A is the sketch map that is used to represent the three-phase model of object-cyclodextrin-solvent system.

Fig. 8-11 illustrates the influence of abnormal flavour (offnote) level that cyclodextrin forms to citral with according to embodiment 20.

Figure 12-15 illustrates the influence of the abnormal flavour level that cyclodextrin forms to citral with according to embodiment 21.

Figure 16-17 illustrates the result of the analysis of sensation of describing among the embodiment 34.

Figure 18-19 illustrates the influence of the abnormal flavour level that cyclodextrin forms to main flavor (key note) flavoring agent with according to embodiment 35-37.

Figure 20 illustrates the result of experiment described in the embodiment 38.

Figure 21-23 illustrates the bottled drink of the experiment described in the embodiment 40.

Figure 24-26 illustrates the typical abnormal flavour result of the citral of embodiment 40A.

Figure 27 illustrates log (P) value of various objects.

Figure 28 illustrates the foundation of the stability/method of citral-cyclodextrin complexes.

Figure 29 illustrate the citral that contains not commensurability and form and cyclodextrin 4 kinds of beverages stability relatively.

Figure 30 illustrate the citral that contains not commensurability and form and cyclodextrin 2 kinds of beverages stability relatively.

Figure 31 illustrates the stable of the citral, color and the vitamin content that use cyclodextrin.

The specific embodiment

Before in detail explaining any embodiment of the present invention, should be appreciated that the present invention its application is not limited to described in the following explanation or the following drawings shown in concrete structure and component arrange.The present invention can have other embodiments, and can implement in many ways or carry out.In addition, should be appreciated that wording used herein and term all are to be purpose of description, should not be considered to have restricted." the comprising " of Shi Yonging, " comprising " or " having " and variant thereof mean and comprise project and equivalent and the sundry item of listing thereafter in this article.Unless otherwise indicated or restriction, term " fix ", " connections ", " support " and " connection " and variant use thereof are extensive, comprises direct with indirect fixing, be connected, support and connect.In addition, " connection " and " connection " are not limited to being connected or connection of physics or machinery.

Be also to be understood that any digital scope as herein described comprises from the whole numerical value between the paramount value of low value.For example, if concentration range is expressed as 1%～50%, it for example means 2%～40%, 10%～30%, or 1%～3% etc. value is all enumerated out in this manual clearly.These only are the examples of specifically noting, all possible combinations of values between minimum and peak all is considered to be explained clearly in this application.

In one embodiment, the invention provides a kind of product that contains at least a object-cyclodextrin inclusion complexes and at least a object catabolite, its object was at least about 10: 1 with object catabolite ratio when described product stored at least 60 days at the acceleration condition of storage down as 88 °F or 100 °F.Aptly, this than can be at least about 5: 1, about 7: 1, about 15: 1 or about 20: 1.Aptly, can measure stable for about 30 days, about 45 days, about 75 days or about 90 days.

In another embodiment, the invention provides a kind of product that contains with the compound object of cyclodextrin, the concentration of described object in described product reduces in time as in 42 days, and the concentration of described object in described product reduces the concentration that is containing in second product of at least a not compound object less than described identical object and reduces.For example, when using the cyclodextrin compound tense, the concentration reduction ratio of the object not concentration of compound object reduces little by about 55%.Aptly, reduce little approximately 25% than the concentration of compound object not, or reduce little about 45% or little by about 75% than the concentration of compound object not when reducing with the concentration of cyclodextrin compound tense object.Aptly, can measure stable for about 30 days, about 45 days, about 60 days, about 75 days or about 90 days.

In another embodiment, the invention provides a kind of product that contains at least a object-cyclodextrin inclusion complexes, wherein said product contains at least a object catabolite, and wherein is lower than at object catabolite after about 30 days in the concentration of object catabolite after about 30 days and is containing concentration in second product of at least a not compound object.Aptly, can measure stable for about 45 days, about 60 days, about 75 days or about 90 days.

In another embodiment, the invention provides a kind of product that contains object-cyclodextrin inclusion complexes, wherein quicken condition of storage as 88 °F or 100 °F under in about 30 days as described in object as described in concentration in the product reduce and be no more than about 25%.Aptly, this reduction is no more than about 35% or be no more than about 50%.Aptly, can measure stable for about 45 days, about 60 days, about 75 days or about 90 days.

In another embodiment, the invention provides a kind of product that contains at least a object-cyclodextrin inclusion complexes and at least a object catabolite, wherein compare with the formation of object catabolite in containing second product of at least a not compound object, the formation of described object catabolite reduces about 500% in time.Aptly, can measure stable for about 30 days, about 45 days, about 60 days, about 75 days or about 90 days.Aptly, the formation of described object catabolite reduces about 200% or about 250% or about 300% or about 400%.

In another embodiment, the present invention also provides a kind of object that reduces in the product to respond the method that is exposed to light and degrades, described method comprises: will be added in the described product with the compound object of cyclodextrin, the degraded that described method reduces described object is than using like products with identical object but object is not better by compound same procedure.For example, can measure degraded by the formation of object catabolite.Can be by being determined at the formation of recently measuring the object catabolite of different time points object and object catabolite.Also can recently measure formation by the percentage that calculates the object catabolite that exists in the described product.Also can measure formation by the area under curve of the appropriate section of gas chromatogram when using gas chromatography-mass spectrometry analysis to come analytic sample.

In another embodiment, the invention provides a kind of method that the concentration of object in product reduces in time that reduces, described method comprises: will be added in the described product with the compound object of cyclodextrin, described method reduces the concentration of described object in described product and reduces in time than using like products with identical object but object is not better by compound same procedure.Can recently measure the concentration reduction by being determined at the percentage of different time points object in described product.For example, in Figure 18, relatively protection (right side) and the total flavor intensity and the abnormal flavour formation of the system of protection (left side); The actual value of the long-pending counting of the asperities of flavor intensity: in the time of 42 days, be 5,674,300,000 for the system of protection, for unprotected system be 3,662,300,000 or the system of protection bigger by 155% than unprotected system strength.In addition, the value that abnormal flavour forms: being 108,161,000 in the system of protection, is 1,424,300,000 in the unprotected system, equals 13.2 times of the abnormal flavour level that forms in the unprotected system.This system action is described by the equation 5,6 in the subsequent paragraphs and 7 with quantic.

In another embodiment, the invention provides the method for stability that a kind of improvement is exposed to the flavoring agent of light time product, described method comprises and will be added in the described product with the compound object of cyclodextrin, and the stability in time that described method is improved the flavoring agent that is exposed to described product of light time is than using like products with identical object but object is not better by compound same procedure.For example, can by measure the object catabolite in time formation or measure the stability that described object in time concentration in described product is calculated flavoring agent.

In another embodiment, the invention provides a kind of product that contains polyunsaturated fatty acid and cyclodextrin, wherein said polyunsaturated fatty acid and described cyclodextrin are compound.

Described the whole bag of tricks can also comprise cyclodextrin is mixed with object to form described and the compound object of cyclodextrin with emulsifier and/or with solvent.Selectively, cyclodextrin, emulsifying agent and thickening agent can mix to form described and the compound object of cyclodextrin.In some embodiments, cyclodextrin, emulsifying agent and thickening agent can be done mixed.In another embodiment, cyclodextrin, emulsifying agent and thickening agent can mix to form first mixture, and described first mixture and solvent form second mixture, and described second mixture mixes with described object, form the compound cyclodextrin of object.In another embodiment, cyclodextrin, emulsifying agent and thickening agent (for example can mix, by do mixing) and mix with object (or solvent and object), wherein the emulsifying agent percentage by weight that accounts for cyclodextrin is at least about 0.5 weight %, and the percentage by weight that thickening agent accounts for cyclodextrin is at least about 0.01 weight %.In some embodiments, not compound cyclodextrin adds so that extra Stabilization to be provided with molar excess.Described method is particularly suitable for comprising the product of beverage.

As herein with appended claims in used, term " cyclodextrin " can refer to the cyclodextrin molecule that the enzymatic conversion by starch forms.Enzyme-specific, for example various forms of cyclodextrin glycosyl transferases (CGTase) can make the helical structure that exists in the starch break to form to have for example specificity cyclodextrin molecular of the three-dimensional polyglucose ring of 6,7 or 8 glucose molecules.For example, α-CGTase can be converted into starch the alpha-cyclodextrin with 6 glucose units, β-CGTase can be converted into starch the beta-schardinger dextrin-with 7 glucose units, and γ-CGTase can be converted into starch the gamma-cyclodextrin with 8 glucose units.Cyclodextrin includes but not limited at least a in alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin and their combination.Known beta-schardinger dextrin-does not have any toxic action, is world wide GRAS (that is, it is generally acknowledged safe) and natural, and is used by the FDA approval, and alpha-cyclodextrin and gamma-cyclodextrin also are considered to natural product, are the U.S. and the GRAS of European Union.

Suitably, cyclodextrin can be deutero-.The deutero-cyclodextrin that is fit to comprises the cyclodextrin of hydroxy alkylated, as 2-hydroxypropyl beta-schardinger dextrin-, 3-hydroxypropyl beta-schardinger dextrin-, 2,3-dihydroxypropyl beta-schardinger dextrin-and hydroxyethyl beta-schardinger dextrin-, and methylated cyclodextrin are as the methyl beta-schardinger dextrin-.

As herein with appended claims in used, " contrast " is to have identical object but the like products that do not have cyclodextrin.

Fig. 1 has schematically shown the three-dimensional cyclic structure (that is macrocyclic structure) of cyclodextrin molecular 10.Cyclodextrin molecular 10 comprises that outside 12, described outside 12 comprise primary hydroxyl and secondary hydroxyl and for hydrophilic.Cyclodextrin molecular 10 also comprises three-dimensional lumen 14, and described three-dimensional lumen 14 comprises carbon atom, hydrogen atom and ehter bond and is hydrophobic.The hydrophobic cavity 14 of cyclodextrin molecular can be used as main body and holds multiple molecule or the object 16 that comprises hydrophobic part, thereby forms cyclodextrin inclusion complexes.

As herein with appended claims in used, term " object " can refer to any molecule, at least a portion of described molecule can be housed inside or be trapped in the three-dimensional lumen that is present in the cyclodextrin molecular, described guest molecule includes but not limited to flavoring agent, smell at least a in flavor regulator, medicine, nutrient (nutraceutical agent) (for example, creatine or vitamin A, C or E), coloring agent and their combination.

The example of flavoring agent can include but not limited to the flavoring agent based on aldehyde, ketone or alcohol.The example of aldehyde flavoring agent can include but not limited at least a in following: acetaldehyde (Fructus Mali pumilae); Benzaldehyde (Fructus Pruni pseudocerasi, Semen Armeniacae Amarum); Anisaldehyde (Radix Glycyrrhizae, Fructus Foeniculi); Cinnamic aldehyde (Cortex Cinnamomi); Citral (for example, geranial, α citral (Fructus Citri Limoniae, limette) and neral, β citral (Fructus Citri Limoniae, limette)); N-capric aldehyde (orange, Fructus Citri Limoniae); Ethyl vanillin (Rhizoma et radix valerianae, butter); Heliotropine, i.e. piperonal (Rhizoma et radix valerianae, butter); Vanillin (Rhizoma et radix valerianae, butter); Jasminal (pungent fruity); Butyraldehyde (butter, cheese); Valeral (butter, cheese); Citronellal (modified, polytype); Decenal (citrus fruit); C-8 aldehyde (citrus fruit); C-9 aldehyde (citrus fruit); C-12 aldehyde (citrus fruit); 2-ethyl butyraldehyde (berry); Hexenoic aldehyde, promptly anti--2 (berries); Tolyl aldehyde (Fructus Pruni pseudocerasi, Semen Armeniacae Amarum); 3,4-dimethoxybenzenecarbonal (Rhizoma et radix valerianae); 2-6-dimethyl-5-heptenal, i.e. melonal ^TM(Fructus Melo); 2,6-dimethyl octanal (green fruit); 2-laurylene aldehyde (Citrus, MIJU); With their combination.

The example of ketone flavoring agent can include but not limited at least a in following: d-carvone (caraway); 1-carvone (Herba Menthae Rotundifoliae); Diacetyl (butter, cheese, " butter ") benzophenone (fruity and pungent flavoring agent, Rhizoma et radix valerianae); Butanone (berry); Maltol (berry), menthone (Herba Menthae), methylpentanone, ethyl butyl ketone, two acetone, methyl hexanone, ethyl-n-amyl ketone (berry, drupe); Acetone acid (cigarette smokes flavor, nut flavor); Acetanisole (Fructus Crataegi, garden heliotrope); Dihydro carvone (Herba Menthae Rotundifoliae); 2,4-dimethyl acetophenone (lavender); 1,3-diphenyl-2-acetone (Semen Armeniacae Amarum); Acetocumene (orrisroot and Herba Ocimi (Herba Ocimi Pilosi), acid); Isojasmone (jasmine); The different methyl ionone of d-(orrisroot sample taste, violet); Isobutyl acetoacetate (brandy sample taste); (4-hydroxy-3-methoxyphenyl)ethyl methyl ketone (Rhizoma Zingiberis Recens); Pulegone (Europe green pepper Mentholum); D-piperitone (mint flavored); Methyl n-heptyl ketone (Flos Rosae Rugosae and tea sample taste); With their combination.

The example of alcohol flavoring agent can include but not limited at least a in following: anise alcohol or p-methoxyl group benzylalcohol (fruity, peach); Benzylalcohol (fruity); Carvacrol or 2-p-cymenol (warm penetrating odor); Carveol; Cinnamyl alcohol (fragrance of a flower); Citronellol (Flos Rosae Rugosae sample gas flavor); Decanol; Dihydrocarveol (acid, Fructus Piperis flavor); Tetrahydrogeraniol or 3,7-dimethyl-1-capryl alcohol (rose scent); Eugenol (Flos Caryophylli); 1,8-is right

Diene-7-O λ or perillyl alcohol (fragrance of a flower, pinaster); The α terpineol; 1,5-

Diene-8-alcohol 1; 1,5-

Diene-8-alcohol 2; P-cymen-8-ol; With their combination.

The example of smelling the flavor regulator can include but not limited at least a in natural perfume material (spice), synthetic perfume, synthetic quintessence oil, natural essential oil and their combinations.

The example of synthetic perfume can include but not limited at least a in terpene hydrocarbon, ester, ether, alcohol, aldehyde, phenol, ketone, acetal, oxime and their combinations.

The example of terpene hydrocarbon can include but not limited at least a in limette terpene, Fructus Citri Limoniae terpene, limonene dimer and their combinations.

The example of ester can include but not limited to peach aldehyde, methyl phenyl ethyl glycidate, allyl hexanoate, amyl salicylate, amyl benzoate, pentyl acetate, benzyl acetate, benzyl benzoate, benzyl salicylate, benzyl propionate, butyl acetate, benzyl butyrate, benzyl phenylacetate, Cedryl acetate., citronellyl acetate, citronellyl formate, acetic acid p-methylphenyl ester, acetic acid 2-tertiary pentyl-cyclohexyl, cyclohexyl acetate, along acetic acid-3-hexene ester, along salicylic acid-3-hexene ester, acetic acid dimethylbenzyl ester, ethyl phthalate, δ-Gui Neizhi, Dibutyl phthalate, ethyl n-butyrate., ethyl acetate, ethyl benzoate, acetic acid turnip ester, acetic acid geranyl ester, γ-dodecalactone, MDJ, salicylic acid β-isopropoxy ethyl ester, linalyl acetate, essence of Niobe, tert-butyl group cyclohexyl between acetic acid, isobornyl acetate, methyl salicylate, ethylene brassylate, the dodecoic acid ethyl, acetic acid methyl phenyl ester, phenethyl isobutyrate,phenylethyl isobutyrate, acetic acid phenethyl phenyl ester, phenethyl acetate, methyl phenyl carbinyl acetate, acetic acid 3,5, the own ester of 5-trimethyl, tirpinyl acetate, triethyl citrate, vertenex, at least a in vetacetyl (vetiver acetate) and their combination.

The example of ether can include but not limited to p-tolyl methyl ether, diphenyl ether, 1,3,4,6,7,8-six hydrogen-4,6,7,8, at least a in 8-pregnancy basic ring penta-β-2-.alpha.-5:6-benzopyran, phenyl isoamyl oxide and their combination.

The example of alcohol can include but not limited at least a in n-octyl alcohol, n-nonyl alcohol, beta-phenyl ethyl dimethyl carbinol, dimethyl benzyl carbinol, dihydromyrcenol carbinol, dimethyl octanol, hexanediol linalool, folic alcohol, nerol, phenoxyethanol, γ-phenyl propanol, beta-phenyl ethanol, styroyl alcohol, terpineol, tetrahydro muguol (tetraphydroalloocimenol), tetrahydrolialool, 9-decen-1-ol and their combination.

The example of aldehyde can include but not limited to n-nonyl aldehyde, undecylene aldehyde, methyl nonyl acetaldehyde, anisaldehyde, benzaldehyde, cyclamen aldehyde, 2-hexyl hexanal, jasmonal H, hyacinthin, 4-(4-hydroxy-4-methyl amyl group)-3-cyclohexene-1-formaldehyde, to the tert-butyl group-Alpha-Methyl hydrogen cinnamic aldehyde, hydroxycitronellal, jasminal, 3, at least a in 5-dimethyl-3-cyclohexene-1-formaldehyde and their combinations.

The example of phenol can include but not limited to methyleugenol.

The example of ketone can include but not limited at least a in 1-carvone, α-damascenone, ionoionone, 4-tertiary pentyl Ketohexamethylene, 3-amyl group-4-acetoxyl group Pentamethylene oxide., menthone, methyl ionone, orivone, acetyl cedrene and their combination.

The example of acetal can include but not limited to phenylacetaldehyde dimethyl acetal.

The example of oxime can include but not limited to 5 methyl 3 heptanone oxime.

Object also can further include but not limited to fatty acid, fatty acid triglycercide, polyunsaturated fatty acid and its triglyceride, tocopherol, lactone, terpenoid, diacetyl, dimethyl sulfide, proline, diformazan hydroxyl furanone, linalool, acetyl propionyl, cocoa products, natural essence (for example, orange, Fructus Lycopersici esculenti, Fructus Mali pumilae, Cortex Cinnamomi, raspberry etc.), quintessence oil (for example, orange, Fructus Citri Limoniae, limette etc.), sweeting agent (for example, aspartame, the neotame element, acesulfame potassium, glucide, NHDC, Radix Glycyrrhizae and the sweeting agent that comes from Flos Chrysanthemi), sabinene, paracymene, p, at least a in the combination of a-dimethyl styrene and they.

The example of polyunsaturated fatty acid (PUFA) can include but not limited to the omega-fatty acid of C18, C20 and C22 and ω-6 fatty acid of C18, C20 and C22.For example, the polyunsaturated fatty acid of Shi Heing comprises docosahexenoic acid (DHA), eicosapentaenoic acid (EPA), arachidonic acid (eicosatetraenoic acid) (being also referred to as arachidonic acid (ARA)), gamma-Linolenic acid (GLA), stearic idonic acid (stearidonic acid), oleic acid, linoleic acid plus linolenic acid.Be also to be understood that since PUFA usually with list, two and triglyceride exist, thereby the constraint form of its free acid and they all is applicable to the present invention.

Fig. 3 shows the sketch map of the formation of diacetyl-cyclodextrin inclusion complexes, and Fig. 5 shows the sketch map of the formation of citral-cyclodextrin inclusion complexes.

As herein with appended claims in used, term " object catabolite " refers to the chemical compound that forms owing to the object that decomposes through contact environment factor such as light and heat.The existence of object catabolite shows that the object concentration in the product reduces.For example, if object is a flavoring agent, product can lose the part local flavor and may form abnormal flavour so.The abnormal flavour agent is more powerful taste agent.Add the flavoring agent loss of strength, product quality can reduce rapidly and significantly.If object is vitamin or nutrient, product can lose the benefit of some vitamin or nutrient so.

As herein with appended claims in used, term " log (P) " or " log (P) value " are a kind of character of the material that can find in the standard reference table, it is meant the octanol/water partition coefficient of this material.Generally speaking, a kind of log of material (P) value is represented its hydrophilic/hydrophobic.P is defined as the ratio of the concentration of this material in capryl alcohol and this material concentration in water.Therefore, if related substances concentration in water is higher than the concentration of this material in capryl alcohol, then the log of this material (P) is for negative.If concentration is higher in capryl alcohol, then log (P) value equals its concentration in capryl alcohol for just as if related substances concentration in water, and then log (P) value is 0.Therefore, object can be characterized by its log (P) value.Log (P) value that table 1 shown in Figure 27 has been listed multiple material for your guidance, some of them can be objects of the present invention.

Example with object of relatively large positive log (P) value (for example, greater than about 2) includes but not limited to citral, linalool, α terpineol and their combination.Example with object of less relatively positive log (P) value (for example, less than about 1 greater than 0) includes but not limited to dimethyl sulfide, diformazan hydroxyl furanone, ethyl maltol, aspartame and their combination.Example with object of relatively large negative log (P) value (for example, less than about-2) includes but not limited to creatine, proline and their combination.Example with object of less relatively negative log (P) value (for example, less than 0 greater than approximately-2) includes but not limited to diacetyl, acetaldehyde, maltol, aspartame and their combination.

Log (P) value is important aspect food and flavoring agent chemistry a lot.The table of log (P) value more than is provided.The log of object (P) value may be important to a lot of aspects of final products (for example, food and flavoring agent).Generally speaking, the organic guest molecule with positive log (P) can successfully be encapsulated in the cyclodextrin.May have competition in containing the mixture of several objects, log (P) value can be used for determining successfully encapsulation of the more possible quilt of which object.Maltol and diformazan hydroxyl furanone are two object examples with similar flavour characteristic (being sweet attribute), but because their log (P) values are different, so their successful level differences in the cyclodextrin encapsulation.Log (P) value may be important in the food with high-moisture or aqueous environment.According to definition, the chemical compound with significantly positive log (P) value is to be difficult for moltenly most, therefore at first migration in packing, separates and exposes change then.Yet the cyclodextrin that high log (P) value but makes them be added in the product is effectively caught and is protected.Aptly, the log of object (P) is greater than about 1.0 or greater than about 1.50 or greater than about 1.75.

Citral (log (P)=3.45) is a kind of Citrus or lemon flavoring agent, can be used in multiple application product such as the acidic beverages.Acidic beverages can include but not limited to lemonade,

The soft drink of Fructus Citri Limoniae-lime flavor (Dr Pepper/Seven-Up, the registered trade mark of Inc.),

The soft drink of Fructus Citri Limoniae-lime flavor (Coca-Cola Company, Atlanta, the registered trade mark of GA), SIERRA

The soft drink of Fructus Citri Limoniae-lime flavor (Pepsico, Purchase, the registered trade mark of NY), tea are (for example With

The registered trade mark of Lipton), alcoholic beverage and their combination.α terpineol (log (P)=3.33) is an a kind of limette flavor flavoring agent, can be used for the like product about citral listed above in.

Benzaldehyde (log (P)=1.48) is a kind of cherry-flavored flavoring agent, can be used for multiple application product, comprises in the acidic beverages.The example of the acidic beverages of available benzaldehyde seasoning includes but not limited to CHERRY

The soft drink of Fructus Pruni pseudocerasi cola flavor (Coca-Cola Company, Atlanta, the registered trade mark of GA).

Vanillin (log (P)=1.05) is a kind of vanilla flavored flavoring agent, can be used for various application products, includes but not limited to vanilla flavored beverage, baked goods and their combination.

Aspartame (log (P)=0.07) is a kind of non-sucrose sweeting agent, can be used for including but not limited to the soft drink of going on a diet in multiple food of going on a diet (diet Food) and the beverage.Neotame also is a kind of non-sucrose sweeting agent, in the Food ﹠ Drink that can be used for going on a diet.

Acetaldehyde (log (P)=-0.17) is a kind of Fructus Mali pumilae flavor flavoring agent, can be used for various application products, includes but not limited to food, beverage, confection etc. and their combination.

Creatine (log (P)=-3.72) is a kind of nutrient, can be used for various application products, includes but not limited to nutritional preparation.The example of nutritional preparation includes but not limited to the powder formulation that can use with breast, water or other liquid and their combinatorial association.

As mentioned above, the cyclodextrin of the present invention's use can comprise alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin and their combination.Use the higher object of hydrophilic therein (promptly, have less log (P) value) embodiment in, can use alpha-cyclodextrin (that is, use separately or be used in combination) to improve the encapsulation (encapsulation) of object in cyclodextrin with the other types cyclodextrin.For example, in the embodiment of using hydrophilic relatively object, the combination that can use alpha-cyclodextrin and beta-schardinger dextrin-is to promote the formation of cyclodextrin inclusion complexes.

As herein with appended claims in used, term " cyclodextrin inclusion complexes " is meant by guest molecule being caught and is contained in the three-dimensional lumen, the complex that forms by at least a portion (encapsulation of molecular level) with the one or more guest molecules of one or more cyclodextrin molecular encapsulations.Described object can be by at least a Van der Waals force holding position of passing through in cavity in hydrogen bond and the hydrophilic-hydrophobic interaction.When cyclodextrin inclusion complexes was water-soluble, object can discharge from cavity.Cyclodextrin inclusion complexes is also referred to as " object-cyclodextrin complexes " at this paper.Because the cavity of cyclodextrin is hydrophobic for it is outside, therefore the object that has positive log (P) value (particularly relatively large positive log (P) value) in cyclodextrin easily encapsulation and in aqueous environment the stable cyclodextrin inclusion complexes of formation because object preferred cyclodextrin cavity and preferred aqueous environments on the thermokinetics.In some embodiments, when expectation compound during more than an object, can with each object respectively encapsulation so that the maximizing efficiency of the relevant object of encapsulation.

As herein with appended claims in used, term " not compound cyclodextrin " generally is meant the cyclodextrin that does not contain object substantially, do not form cyclodextrin inclusion complexes.The cyclodextrin that " does not contain object substantially " is meant that generally the most of cyclodextrin that comprises or not the cyclodextrin source of object in its cavity.

As herein with appended claims in used, term " hydrocolloid " generally is meant the material that forms gel with water.Hydrocolloid can include but not limited at least a in xanthan gum, pectin, Radix Acaciae senegalis, Tragacanth, guar gum, carrageenin, locust bean gum and their combination.

As herein with appended claims in used, term " pectin " is meant the hydrocolloidal polysaccharide that may reside in the plant tissue (for example, mature fruit and vegetable).Pectin can include but not limited at least a in beet pectin, the fruit pectin pectin of peel of Citrus reticulata Blanco (for example, from) and their combination.The pectin that uses can have indefinite molecular weight.

Cyclodextrin inclusion complexes of the present invention can be used in multiple application or the final products, include but not limited to that food (for example, beverage, as soda pop, citrus beverages, lemonade, fruit juice, soft drink, sports drink, vitamin enrichment beverage etc., salad dressing, puffed rice, corn, Sucus Mali pumilae, coffee, cookies, chocolate pie, gelatin, other desserts, other bake food, flavouring agent etc.), chewing gum, dentifrice (gargling agent) as toothpaste and mouth, confection, flavoring agent, spice, medicine (as cough syrup preparation etc.), nutrient, cosmetics, agricultural application product (for example, herbicide, agrochemical), at least a in the combination of photograph emulsion and they.In some embodiments, cyclodextrin inclusion complexes can be as awaiting further processing, separation and exsiccant middle isolation medium (for example, using with waste stream).

Cyclodextrin inclusion complexes can be used to improve object stability, makes it to be converted into free-pouring powder or improves its dissolubility, conveying or performance.The amount of guest molecule that can be encapsulated is directly related with the molecular weight of guest molecule.In some embodiments, 1 mole of object of 1 mole of cyclodextrin encapsulation.According to this mol ratio, only for instance, using diacetyl (molecular weight 86 dalton) as object and use in beta-schardinger dextrin-(molecular weight 1135 dalton's) the embodiment, theoretical maximum is left (86/ (86+1135)) * 100=7.04 weight %.

In some embodiments, cyclodextrin can carry out self assembly and form nanostructured in solution, nanostructured 20 as shown in Figure 2, and 2 moles cyclodextrin molecular can comprise 3 moles guest molecule in this structure.For example, in using the embodiment of diacetyl, may keep the diacetyl of 10.21 weight %, and in using the embodiment of citral, may keep the citral (for example 10-14 weight % keeps) of at least 10 weight % as object as object.Fig. 4 illustrates the sketch map of the nanostructured that can form between 3 moles of diacetyl molecules and the 2 moles of cyclodextrin moleculars.Fig. 6 illustrates the sketch map of the nanostructured that can form between 3 moles of citral molecules and the 2 moles of cyclodextrin moleculars.Other composite fortifiers, for example pectin can be assisted self assembling process, and can keep object in whole dry run: 3: 2 mol ratio of cyclodextrin.In some embodiments, because the cyclodextrin molecular self assembly is a nanostructured, also may be object therefore: 5: 3 mol ratio of cyclodextrin.

Cyclodextrin inclusion complexes forms in solution.Dry run is locked at least a portion object in the cavity of cyclodextrin momently, and can produce the free-pouring dried powder that contains cyclodextrin inclusion complexes.

Hydrophobic (water-insoluble) character of cyclodextrin cavity is the easiest catching (hydrophobicity) object rather than water solublity (hydrophilic) object preferentially.Compare with typical spray drying method, this phenomenon can cause component imbalance and total recovery poor.

In some embodiments of the present invention, by selecting the independent encapsulation of key component to avoid competition between hydrophilic and the hydrophobic interaction.For example, under the situation of butter flavoring agent, fatty acid and lactone are than the easier formation cyclodextrin inclusion complexes of diacetyl.Yet these chemical compounds are not that the key feature relevant with butter impacts (impact) chemical compound, and they will reduce the total recovery of diacetyl and other water solublity, volatile ingredient.In some embodiments, the key component in the butter flavoring agent (being diacetyl) is maximized to prepare shock-resistant, more stable and more economical product.For example, under the situation of Fructus Citri Limoniae flavoring agent, most Fructus Citri Limoniae flavor ingredients encapsulation on an equal basis well in cyclodextrin.Yet terpenes (component of Fructus Citri Limoniae flavoring agent) has low seasoning value, but it is about 90% to account for the Fructus Citri Limoniae flavouring mixture, and citral is the crucial flavoring agent composition of Fructus Citri Limoniae flavoring agent.In some embodiments, independent encapsulation citral.Reduce the complexity of raw material by the independent encapsulation of selection key component (for example, diacetyl, citral etc.), thereby make engineering step and process economics optimization.

In some embodiments, order about the enclose process that is used to form cyclodextrin inclusion complexes of finishing by the object that adds molar excess.For example, (for example, when the object that uses during) in some embodiments as diacetyl, described object can be with object: 3: 1 mol ratio of cyclodextrin and cyclodextrin combination.In some embodiments, in forming complex, use the object of molar excess not only to order about the formation of cyclodextrin inclusion complexes, but also can for example any loss of object in additional this process in the embodiment of using the volatility object.

In some embodiments, control is by mixing cyclodextrin and guest molecule the viscosity of suspension, emulsion or mixture of formation in solvent, and for example increases solids content without other adjustment and keep the compatibility with common spray drying technology.Can add tight the contact and auxiliary enclose process between emulsifying agent (as thickening agent, gellant, polysaccharide, hydrocolloid, natural gum as xanthan gum, gather glucuronic acid (polyglucoronic) and derivant thereof) retaining ring dextrin and the object.Especially, can use low-molecular-weight hydrocolloid.A preferred hydrocolloid is a pectin, especially beet pectin.Emulsifying agent can be assisted the enclose process and do not used hyperpyrexia or cosolvent (as ethanol, acetone, isopropyl alcohol etc.) to increase dissolubility.

In some embodiments, the water content of reduction suspension, emulsion or mixture works as hydrophobic compound to force object basically.This process can increase or even the relatively reservation of hydrophilic object such as acetaldehyde, diacetyl, dimethyl sulfide etc.Reduce water content the volume of production by spray dryer is maximized, and reduce volatility object evaporable chance in this process, this can be avoided reducing total recovery.

In some embodiments of the present invention, cyclodextrin inclusion complexes can form by the following method, some or all during it can may further comprise the steps:

(1) do cyclodextrin and emulsifying agent (for example, pectin) mixed;

(2) dry blend of cyclodextrin and emulsifying agent is mixed in reactor with solvent such as water and stir;

(3) add object and stirring (for example, about 5～8 hours);

(4) cooling reactor (for example, opening cooling jacket);

(5) (for example, about 12～36 hours) stir the mixture;

(6) emulsifying (for example, splashing into blender) with lightning blender in the groove or high shear; With

(7), form powder with the cyclodextrin inclusion complexes drying.

These steps not necessarily need be carried out with said sequence.In addition, proved that said method is very good, but because the change of this method serviceability temperature, incorporation time and other procedure parameters carry out.

In some embodiments, the step 1 in the said method can use the interior blender of groove to finish in reactor, adds hot water in the step 2 in reactor.For example, in some embodiments, said method uses 1000 gal reactor to finish, and described reactor is equipped with temperature control overcoat and embedded high-shear mixer, and described reactor directly is connected with spray dryer.In some embodiments, cyclodextrin and emulsifying agent can be done in independent device (for example, banded blender etc.) and mix, and then it are added in the completed reactor of remainder of said method.

Can use the multiple percentage by weight of emulsifying agent and cyclodextrin, include but not limited to emulsifying agent: the cyclodextrin percentage by weight is at least about 0.5%, particularly at least about 1%, more especially at least about 2%.In addition, can use emulsifying agent: the percentage by weight of cyclodextrin is lower than about 10%, particularly is lower than approximately 6%, more especially is lower than about 4%.

Step 2 in the said method can be used for heating, cooling off or not only heated but also the reactor of refrigerative overcoat carries out being equipped with.In some embodiments, mixing and stirring can at room temperature be carried out.In some embodiments, mix and stir and to carry out being higher than under the temperature of room temperature.The reactor size can be depending on production scale.For example can use 100 gallons reactor.Reactor can comprise paddle agitator and condenser unit.In some embodiments, step 1 is finished in reactor, and in step 2, the deionized water of heat is incorporated in the dry blend of cyclodextrin in the same reactor and pectin.

Step 3 can be finished in closed reactor, and perhaps reactor can be exposed in the environment momently when adding object, and is behind the adding object that reactor is airtight again.Can heat when adding object and during the stirring of step 3.For example, in some embodiments, with extremely about 55-60 ℃ of mixture heated.

Step 4 can use the coolant system that comprises cooling jacket to finish.For example, reactor can cool off by propylene glycol coolant and cooling jacket.

Stirring in the step 2, the stirring in the step 3 and the stirring in the step 5 can by jolt, stir, reverse and their combination at least a finishing.

In step 6, the mixture of cyclodextrin, emulsifying agent, water and object (for example can use high-shear mixer, ROSS board blender (for example, with 10000RPM 90 seconds) or SILVERSTON board blender (for example, with 10000RPM 5 minutes)), the lightning blender or be transferred to as back in the homogenate pump of a spray dryer part simple mix and their combination in carry out one of at least emulsifying.

Step 7 in the said method can be passed through at least a the finishing in air drying, vacuum drying, spray drying (for example, using nozzle spray drier, rotating disk spray dryer etc.), oven drying and their combination.

In some embodiments, recombination process can adopt mounting method, and mixture can be by above-mentioned drying.In other embodiments, mixture can be through suitable dilution with spray drying.Be used to improve the production capacity and the stable distinct methods of cyclodextrin inclusion complexes, comprise and form liquid or the emulsion form that contains cyclodextrin inclusion complexes, be the application PCT/US2006/012529 of common pending trial and the theme of PCT/US2006/012528, this by reference their full content incorporate into.

As mentioned above, the encapsulation of guest molecule can be avoided guest molecule and other component interactions and reaction and cause that abnormal flavour forms; And make guest molecule stablize anti-degraded (for example, hydrolysis, oxidation etc.).Make object stablize the expectation function or the function (for example, taste, abnormal smells from the patient etc.) of the commodity that anti-degraded can improve or strengthen encapsulated object of containing of gained.

The abnormal flavour that may weaken main or expectation function or function may be degraded and produce to a lot of objects.For example, a lot of objects or smell the flavor regulator and may degrade and produce the taste of the expectation that may weaken commodity or the abnormal flavour taste or the abnormal smells from the patient of abnormal smells from the patient.Object also can pass through photooxidative degradation.For instance, Fig. 7 illustrates the degradation mechanism of citral.The degradation rate of object (that is, abnormal flavour forms speed) is followed following general dynamics rate equation usually:

Wherein [object] is meant the molar concentration of object in the solution, and [RC] is meant in the solution with the object reaction and makes the reactive compound of object degraded () molar concentration for example, acid, [abnormal flavour] is meant the molar concentration of the abnormal flavour of formation.Power x, y and z represent kinetics progression, depend on the reaction of relevant object that exists in solution and the generation abnormal flavour that takes place between the reactive compound accordingly.Therefore, the power of the kinetics progression of the molar concentration of the degradation rate of object and object and any reactive compound decision is long-pending proportional.

For example, on behalf of citral, following equation degrade in acid solution under any given temperature and concentration and is formed abnormal flavour:

Wherein, based on the degradation mechanism of citral shown in Figure 7,

Above-described any object can be protected and stablizes in this mode.For example; cyclodextrin can be used for protection and/or stablizes multiple guest molecule; strengthen the expectation function or the function of product, described guest molecule includes but not limited to following guest molecule: citral, benzaldehyde, α terpineol, vanillin, aspartame, neotame, acetaldehyde, creatine and their combination.Described the example of this phenomenon among the embodiment 21, and be presented among table 2 and Figure 12-15.Particularly, prove this phenomenon by sample 1BH3,1BH4, the 1BH5 that more all is added with citral and sample 3FH3,3FH4 that water solublity Herba Rosmarini Officinalis (WSR) is wherein all arranged and 3FH5 and BCD sample.In 1BH and 3FH sample, 1,5- Diene-8-alcohol is converted into p-cymen-8-ol, for example observes 1,5-

The lowering of concentration of diene-8-alcohol, and p-cymen-8-ol concentration raises.Yet, these reactions or variation do not take place in shielded BCD sample.

" object stabilisation systems " can instigate any system that a relevant object (or a plurality of object) is stable and the protection object avoids degrading.The present invention includes the embodiment of several object stabilisation systemss, describe in detail more as following institute.

The protection of object and/or stable can the realization by excessive cyclodextrin (for example, not compound cyclodextrin) is provided in the final powder-product of cyclodextrin inclusion complexes.In other words, the dry powder that forms in the step 7 of not compound cyclodextrin and said method done mix the object that can obtain having desired amount and cyclodextrin (promptly, comprise excessive not compound cyclodextrin) free-pouring dry powder (this paper is called " object-cyclodextrin/cyclodextrin blend composition "), it can be used in multiple application or the commodity.Object-cyclodextrin ratios in described object-cyclodextrin/cyclodextrin blend composition depends on object tire (if object is flavoring agent, then being the seasoning value for example) and the expectation function in final products thereof.When object-cyclodextrin/cyclodextrin blend composition being added or is used for Related product, the excessive not compound cyclodextrin protection in object-cyclodextrin/cyclodextrin blend composition and/or stablize object (comprise and avoid photooxidation).For example, the degradation rate of the flavoring agent of the flavoring agent powder that contains object-cyclodextrin/cyclodextrin blend composition in reducing the beverage application product and be effective for this beverage provides suitable taste profile simultaneously.

Can use multiple systems to add excessive not compound cyclodextrin with protection and/or stable object.In some embodiments, described object-cyclodextrin/cyclodextrin blend composition (is for example added final products as dry powder, the percentage by weight that object-cyclodextrin/cyclodextrin blend composition accounts for product is about 0.05 weight %～about 0.50 weight %, particularly about 0.15 weight %～about 0.30 weight %, more especially about 0.2 weight %).

In some embodiments, if the dissolubility of powder allows, then object-cyclodextrin/cyclodextrin blend composition is added fluid product, emulsion or emulsion compatibility product are (for example, the flavoring agent emulsion) in, then with described fluid product, Emulsion or Emulsion compatibility product account for the about 0.05 weight % of product～about 0.50 weight % with for example object-cyclodextrin/cyclodextrin blend composition, particularly about 0.15 weight %～about 0.30 weight %, the percentage by weight of more especially about 0.2 weight % adds in the final products, like this percentage by weight of the object flavoring agent level that can obtain to expect in final products.In some embodiments, excessive not compound cyclodextrin can be added in the compositions that contains in steps the cyclodextrin inclusion complexes that forms in 6, thereby skip over step 7 (drying steps), formation can above-mentioned percentage by weight be added to stable emulsion or the emulsion compatibility product in the final products.Emulsion compatibility product can be added in another final products (for example, beverage, salad dressing, dessert and/or flavouring agent).In some embodiments, emulsion compatibility product can slurry or the form of coating mixture provide or be added in slurry or the coating mixture, this slurry or coating mixture can be used as to be stablized coating and is sprayed on the substrate and (for example, the flavoring agent emulsion is sprayed on corn, dessert, flavouring agent, nutrition bar and/or snack food such as pretzel, the potato chips etc.).

Provide the cyclodextrin inclusion complexes of liquid form can have but not need and have several advantages.At first, liquid form is for custom is more familiar for the beverage user of the seasoning composition that adds the liquid concentrate form in their beverage, user is more friendly.The second, liquid form can easily be sprayed on the dried foods that comprises food listed above, obtains the equally distributed stable coating that comprises seasoning composition.Different with the application product of existing spraying on it, the seasoning composition of spraying on it that contains cyclodextrin inclusion complexes do not need common volatile solvent or extra coating or protective layer that seasoning composition is remained on this dry matrices.The 3rd, cyclodextrin can prolong the storage life of these food, because cyclodextrin does not have hygroscopicity, therefore can not cause ageing, desalination or the freshness of basal food or beverage to descend.The 4th, dry run may be that cost is high, and some objects (for example, the object that exists in free object or the cyclodextrin inclusion complexes) possible loss in drying, and this makes drying steps be difficult to optimization and finishes economically.The reason of specifically not mentioning with other this paper for these reasons, the cyclodextrin inclusion complexes that liquid form is provided in some embodiments may be useful.The cyclodextrin inclusion complexes of emulsion form (for example can be added to final products, beverage or food) in (for example to give the suitable object feature of final products, taste profile), and guarantee simultaneously cyclodextrin in the final products in the legal limit of given product (for example, be no more than 0.2 weight % of some products, or be no more than 2 weight % of some products).

Because to the encapsulation of object and the balance that existence is set up between (or not compound) guest molecule and the cyclodextrin molecular of dissociating, can impel to the encapsulation direction of balance to object so in system, add excessive not compound cyclodextrin at cyclodextrin.As mentioned above, the amount of free object reduces the formation speed of object degradation rate and abnormal flavour in the minimizing system.In addition, particularly in beverage or other liquid application products, on thermodynamics and/or kinetics, with encapsulated comparing not, object may more be partial in cyclodextrin encapsulated.This phenomenon is extended by adding excessive not compound cyclodextrin.If any, also possible, a small amount of abnormal flavour molecule of formation may be encapsulated within the cyclodextrin, quilt basic " sheltering " in final products.In other words, in some embodiments, because the chemical composition of abnormal flavour, abnormal flavour may combine with cyclodextrin highly stablely, and this may cause sheltering the effect of any abnormal flavour that may form.Therefore, in some embodiments, excessive not compound cyclodextrin can be used as that trapping agent is sheltered or piece-rate system in may disturb other and the miscible component of water of the expectation function of product or function.

Fig. 7 A illustrates the three-phase model of representative object-cyclodextrin-solvent system.The object that uses among Fig. 7 A is a citral, and the solvent of use is a water, but should be appreciated that the citral that shows among Fig. 7 A and water only are the purposes for example.Yet, it will be appreciated by those skilled in the art that the three-phase model that shows among Fig. 7 A can be used for representing various objects and solvent.About to other information of the similar three-phase model shown in Fig. 7 can be referring to Lantz etc., " Use of the three-phase model and headspace analysis forthe facile determination of all partition/association constants for highly volatilesolute-cyclodextrin-water systems; " Anal Bioanal Chem (2005) 383:160-166, the document is incorporated this paper by reference into.

This three-phase model can be used for explaining in the formation of (1) cyclodextrin inclusion complexes, in the beverage application product of (2) cyclodextrin inclusion complexes, and/or (3) phenomenon of in the flavoring agent emulsion, taking place.The flavoring agent emulsion can comprise in the said method for example dry before or do not carry out the slurry that forms in the step 5 or 6 of drying steps, or be resuspended in the slurry that forms in the solvent by the dry powder that will contain cyclodextrin inclusion complexes.As mentioned above, this flavoring agent emulsion can be added in the beverage application product (for example), or be sprayed on the substrate as concentrate.

Shown in Fig. 7 A, wherein object can exist three-phase, and promptly gas phase, water and cyclodextrin (are also referred to as " pseudo-phase ") mutually sometimes.Three balances and relevant equilibrium constant thereof (are K _H, K _P1And K _P2) be used for describing the existence of object at this three-phase:

$S_{\left(g\right)}\stackrel{K_{P1}}{\&RightArrow;}{S}_{\left(\mathrm{CD}\right)};{\mathrm{<figure-callout\; id="1"\; label="K\; P"\; filenames="A2007800517810060H1.png,A2007800517810071H1.png"\; state="\{\{state\}\}">K</figure-callout>}}_P=\frac{C_S^{\mathrm{CD}}}{P_S}---\left(2\right)$

$S_{\left(\mathrm{aq}\right)}\stackrel{K_{P2}}{\&RightArrow;}{S}_{\left(\mathrm{CD}\right)};{\mathrm{<figure-callout\; id="2"\; label="K\; P"\; filenames="A2007800517810060H1.png,A2007800517810061H2.png"\; state="\{\{state\}\}">K</figure-callout>}}_P=\frac{C_S^{\mathrm{CD}}}{C_S^{\mathrm{aq}}}---\left(3\right)$

$K_H=\frac{K_{P1}}{K_{P2}}---\left(4\right)$

Wherein " S " representative represent with subscript, at the solute (that is, object) of the corresponding system in mutually of system, " g " represents gas phase, " aq " represents water, " CD " represents cyclodextrin phase, " C _s" concentration of solute of representative in corresponding phase (that is, aq or CD represent with subscript), the dividing potential drop of the solute of Ps representative in gas phase.

Be all objects in the three-phase system shown in the key diagram 7A, the total mole number (n of object _s ^Always) can represent by following equation:

Be any loss of object in the product (for example, beverage or flavoring agent emulsion) under the explanation stable state, the total mole number (n of the object that can be used for feeling _s ^TasteFor example, the taste that is used for beverage or flavoring agent emulsion) can represent by following equation:

F wherein _(P)Be partition function, it represents any migration (or loss) of object, for example the barrier of the beverage by wherein filling the flavoring agent emulsion or the loss of container (for example, the plastic bottle that is formed by polyethylene or polyethylene terephthalate (PET)).

For object with big positive log (P) value, the encapsulation of object in cyclodextrin be thermodynamics favourable (be K _P1And K _P2Will be greater than 1), following relation will take place:

$n_S^{\mathrm{CD}}>>n_S^{\mathrm{aq}}>n_S^g>f_{\left(P\right)}---\left(7\right)$

The most of object that exists in the system so all will be the form of cyclodextrin inclusion complexes.Not only water and gas phase middle reaches are minimum from the amount of object, and object is also reduced to minimum by the migration of barrier or container.Therefore, the major part in the object that can be used for feeling will be present in cyclodextrin mutually in, and the total mole number (n of the object that can be used for feeling _s ^Taste) can followingly carry out approximate calculation:

The cyclodextrin inclusion complexes that forms between object and the cyclodextrin in the solution can more completely be represented by following equation:

$S_{\left(\mathrm{aq}\right)}+{\mathrm{CD}}_{\left(\mathrm{aq}\right)}\stackrel{K_{P2}}{\&RightArrow;}S\&CenterDot;{\mathrm{CD}}_{\left(\mathrm{aq}\right)};{\mathrm{<figure-callout\; id="2"\; label="K\; P"\; filenames="A2007800517810060H1.png,A2007800517810061H2.png"\; state="\{\{state\}\}">K</figure-callout>}}_P=\frac{{[S\&CenterDot;\mathrm{CD}]}_{\left(\mathrm{aq}\right)}}{{\left[S\right]}_{\left(\mathrm{aq}\right)}{\left[\mathrm{CD}\right]}_{\left(\mathrm{aq}\right)}}---\left(9\right)$

Rule of thumb, support data of the present invention to show that log (P) value of object may be the formation of cyclodextrin inclusion complexes and the factor of stability.That is to say that empirical data shows that the net energy loss of following encapsulation process in the solution orders about the balance shown in the above equation 9 and move right, this balance can be predicted at least in part by log (P) value of relevant object.Log (P) value of having found object may be the factor with final products of high-moisture or environment.For example, the object with big relatively positive log (P) value is least soluble in water usually, can move from final products and separate, and is subjected to the influence of environmental change in packing easily.Yet by add cyclodextrin in final products, big relatively log (P) value can make these objects be caught effectively and be protected.In other words, in some embodiments, use method of the present invention can easily stablize usually the object of difficult steadyization.

Be the effect of explanation object log (P) value, the equilibrium constant (K of object stability in the representative system _P2') can represent by following equation:

${{\mathrm{<figure-callout\; id="2"\; label="K\; P"\; filenames="A2007800517810060H1.png,A2007800517810061H2.png"\; state="\{\{state\}\}">K</figure-callout>}}_P}^{\&prime;}=\log \left(P\right)\frac{{[S\&CenterDot;\mathrm{CD}]}_{\left(\mathrm{aq}\right)}}{{\left[S\right]}_{\left(\mathrm{aq}\right)}{\left[\mathrm{CD}\right]}_{\left(\mathrm{aq}\right)}}---\left(10\right)$

Wherein log (P) is log (P) value of relevant object (S) in the system.Equation 10 has been set up the model of consideration object log (P) value.Equation 10 shows how to obtain the thermodynamically metastable fixed system from first forming cyclodextrin inclusion complexes with the object with big relatively positive log (P) value.For example, in some embodiments, use object can form stabilisation systems (being the object stabilisation systems) with positive log (P) value.In some embodiments, use log (P) value be at least about+1 object can form stabilisation systems.In some embodiments, use log (P) value be at least about+2 object can form stabilisation systems.In some embodiments, use log (P) value be at least about+3 object can form stabilisation systems.In addition, as can be seen, not only use object can form thermodynamically stable system with positive log (P) value, and avoid degrading and also can form thermodynamically stable system further stablize object further to make the balanced deflection right side shown in the above equation 9 and move and to increase compound object and ratio free or not compound object by in cyclodextrin inclusion complexes, adding extra not compound cyclodextrin.

Though log (P) value is good experience indication, but from a plurality of lists of references, obtain, but another important criterion is the binding constant (in a single day promptly form complex, object is bonded intensity in cyclodextrin cavity) of specific object.Unfortunately, the binding constant of object is determined by experiment.For example, under the situation of limonene and citral, although log (P) value is similar, citral can form much better than complex.As a result, even there is high limonene concentration,, also be that citral preferentially is protected until being consumed because the citral binding constant is higher.This is a unforeseeable benefit, can't directly predict from present scientific literature.

In some embodiments of the present invention, such as equation 10 support, object is added in product, system or the application product (for example, beverage) with complex form not, and not compound cyclodextrin is added in identical product, system or the application product.Shown in equation 10, the stability of object in this system (and object avoid degrading protection) will depend on log (P) value of object at least in part.For example, object can be added to the object concentration in system, to obtain to expect in the system, and not compound cyclodextrin is added in the system to stablize object and to protect object to avoid degraded.In some embodiments, the concentration of object in system is at least about 1ppm, particularly at least about 5ppm, more especially at least about 10ppm.In some embodiments, the concentration of object in system is lower than about 200ppm, particularly is lower than about 150ppm, more especially is lower than about 100ppm.In some embodiments, the total concentration of Citrus component for example can surpass 1000ppm (for example, when having limonene).Yet, do not prove that also this is an impediment to of the present invention stablizing/protection scheme.

In some embodiments, with cyclodextrin with cyclodextrin: the mol ratio of object was added in the system greater than 1: 1.Shown in equation 10, cyclodextrin can be by log (P) value prediction of object to the Stabilization of object in the system.In some embodiments, the object of selection has positive log (P) value.In some embodiments, the log of object (P) value is greater than about+1.In some embodiments, the log of object (P) value is greater than about+2.In some embodiments, the log of object (P) value is greater than about+3.

No matter described product, system or application product comprise that free/not compound object still is the object of cyclodextrin encapsulation, can add described object in final products, system or application product, obtaining the object concentration of expectation, and not compound cyclodextrin can be added in described product, system or the application product and maintain in the legal limit with total weight percent with cyclodextrin.For example, in some embodiments, the percentage by weight that cyclodextrin accounts for system is about 0.05 weight %～about 0.50 weight %, particularly about 0.15 weight %～about 0.30 weight %, more especially about 0.2 weight %.In some embodiments, not compound cyclodextrin is mixed with object, be added in the system then.In some embodiments, not compound cyclodextrin is separated with object, in the directly adding system.Embodiment 20 shows the not compound alpha-cyclodextrin that is added in the solution that contains citral or the Stabilization of beta-schardinger dextrin-.Explain that as embodiment 20 citral is protected to be avoided degrading and suppress the formation of abnormal flavour.Equation 10 shows that the Stabilization to citral can be because big relatively log (P) value (that is, 3.45) of citral to small part.

Consider the stability of object in the measurable system that contains cyclodextrin of object log (P).Utilize compound thermodynamics in the solution can form the environment of protection and stable object, and this can further promote by adding excessive not compound cyclodextrin.The release characteristics of object from cyclodextrin is subjected to the air/water partition coefficient K of object _HControl.If when containing the system of cyclodextrin inclusion complexes and placing non-equilibrium environment such as mouth, then compare K with log (P) _HMay be big.It will be understood by those skilled in the art that to exist in the system that similar equation and relation are applicable to each object in the system more than an object.

Object is that flavoring agent and commodity are in the embodiment of beverage (or other liquid) therein, and cyclodextrin can protect the flavoring agent in the fluid product to avoid degraded, but when can from encapsulation, discharging flavoring agent during taste bud in the described liquid contact opening.Therefore, can keep the desired taste or the fragrance of product, can carry suitable taste or fragrance characteristic, prevent the degraded of taste or fragrance simultaneously, and the cyclodextrin of law allowance is provided to described beverage simultaneously.Embodiment 21-22 has further described this phenomenon, and table 2 and 3 and Fig. 7-10 in it is further specified.

Directly relatively obtained amazing and unexpected result by beta-schardinger dextrin-or the stable beverage of hydroxypropyl-beta-schardinger dextrin-.Although hydroxypropyl-beta-schardinger dextrin-may cause excellent colour stability (shown in embodiment 40); But preventing that its effect is lower than beta-schardinger dextrin-aspect the flavoring agent abnormal flavour, even its bigger water solublity is considered to improve this two kinds of protected modes.Therefore, when with all at 25 ℃ of alpha-cyclodextrins (14.5g/100ml) of measuring down and gamma-cyclodextrin (23.2g/100ml) when comparing, as if the cavity size of beta-schardinger dextrin-and beyond thought low aqueous solubility (1.85g/100ml) provide nanoemulsions to form required surroundings, and observe Stabilization.The mixture of beta-schardinger dextrin-and hydroxypropyl-beta-schardinger dextrin-can be used for obtaining colour stability and prevents abnormal flavour.Aptly, beta-schardinger dextrin-amount in final products is about 0.01 weight %～about 0.1 weight %, and hydroxypropyl-beta-schardinger dextrin-amount in final products is about 0.05 weight %～about 0.3 weight %.Aptly, to have ratio be about 2: 1～about 1: 30 for hydroxypropyl-beta-schardinger dextrin-and beta-schardinger dextrin-.

In following examples, set forth each feature of the present invention and aspect, these embodiment are intended to illustration and do not have restricted.If not explanation in addition, all embodiment under atmospheric pressure carry out.

Embodiment 1: contain beta-schardinger dextrin-and diacetyl, as cyclodextrin inclusion complexes of the pectin of emulsifying agent and preparation method thereof

Under atmospheric pressure, in 100 gal reactor with 49895.1600g (110.02lb) beta-schardinger dextrin-and 997.9g (2.20lb) beet pectin (pectin: beta-schardinger dextrin-, 2 weight %; XPQ EMP 5 beet pectins obtain from Degussa-France) do and mix, form dry blend.100 gal reactor have overcoat and are used for heating and cooling, comprise paddle agitator and comprise condenser unit.Supply the propylene glycol coolant of about 40 (4.5 ℃) to reactor.When beginning, the propylene glycol coolant system closes the insulator of the somewhat similar reactor of function of overcoat.The deionized water of 124737.9g (275.051b) heat is added in the dry blend of beta-schardinger dextrin-and pectin.Water temperature is about 118 °F (48 ℃).The paddle agitator that uses reactor was with mixture stir about 30 minutes.Then reactor is temporarily opened, added 11226.4110g (24.751b) diacetyl (as hereinafter used, " diacetyl " among the embodiment is meant buys the Chemical in Aldrich, Milwaukee, the diacetyl of WI).Closed reactor does not heat down the gained mixture was stirred 8 hours again.Then, reactor jacket is connected with the propylene glycol coolant system.Coolant is opened to 40 °F (4.5 ℃), with mixture stir about 36 hours.Use the high shear tank mixer for example to be generally used in the spray drying operation those then and come emulsifying mixt.With mixture spray drying on the nozzle exsiccator, the inlet temperature of exsiccator is about 410 °F (210 ℃) then, and outlet temperature is about 221 °F (105 ℃).Diacetylated percent retention is 12.59 weight % in the cyclodextrin inclusion complexes.Moisture measurement is 4.0%.Cyclodextrin inclusion complexes comprises and is lower than 0.3% surperficial diacetyl, and the granulometry of cyclodextrin inclusion complexes is 99.7% by 80 mesh sieves.It will be appreciated by those skilled in the art that available additive method control heating and cooling.For example, diacetyl can add in the slurry of room temperature, and heating and cooling automatically.

Embodiment 2: contain alpha-cyclodextrin and diacetyl, as cyclodextrin inclusion complexes of the pectin of emulsifying agent and preparation method thereof

The beta-schardinger dextrin-of embodiment 1 replaces with alpha-cyclodextrin, with 1 weight % pectin (be pectin: beta-schardinger dextrin-, 1 weight %; XPQ EMP 5 beet pectins obtain from Degussa-France).According to embodiment 1 described method processing and drying composite.Diacetylated percent retention is 11.4 weight % in the cyclodextrin inclusion complexes.

Embodiment 3: contain beta-schardinger dextrin-and orange essence (orange essence), as cyclodextrin inclusion complexes of the pectin of emulsifying agent and preparation method thereof

To be added in the dry blend of the beta-schardinger dextrin-that forms according to embodiment 1 method and 2 weight % pectin as water from the aqueous wash streams orange essence of fruit juice production.Additionally do not add entry, solids content is about 28%.Method according to embodiment 1 forms cyclodextrin inclusion complexes.Dried inclusion complex contains the ethyl n-butyrate. of the acetaldehyde of 3～4 weight % that have an appointment, about 5～7 weight %, about 2～3 weight % linalools and other citrus flavour enhancer.The cyclodextrin inclusion complexes of gained can be used in fragrant (top-noting) beverage.

Embodiment 4: contain beta-schardinger dextrin-and acetyl propionyl, as cyclodextrin inclusion complexes of the pectin of emulsifying agent and preparation method thereof

In the beta-schardinger dextrin-that the acetyl propionyl of the molar excess method according to embodiment 1 that is added to is formed and the dry blend of 2 weight % pectin.The percent retention of acetyl propionyl is 9.27 weight % in the cyclodextrin inclusion complexes.This mixture can be used for not containing in diacetylated the XIANGHUANG oil system.

Embodiment 5: orange oil flavoring agent (orange oil Flavor) product and preparation method thereof

With orange oil (is Orange Bresil; 75g) be added to the aqueous phase that contains 635g water, 403.75g maltodextrin and 21.25g beet pectin (can obtain production number XPQ EMP 5) from Degussa-France.Under stirring gently orange oil is added to aqueous phase, vigorous stirring forms mixture under 10000RPM then.Then mixture is passed through homogenizer under 250 crust, form emulsion.With the dry emulsion of NIRO board spray dryer, inlet temperature is about 180 ℃, outlet temperature be about 90 ℃ to form dry products.Use the oil mass (g) in the 100g dry products to come quantitative flavoring agent percent retention then divided by the oil content in the starting mixt.The percent retention of orange oil is about 91.5%.

Embodiment 6: orange oil flavoring agent product and preparation method thereof

With orange oil (75g) be added to contain 635g water, 297.50g maltodextrin and 127.50g Radix Acaciae senegalis (can from

Naturels International acquisition) aqueous phase.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 91.5%.

Embodiment 7: orange oil flavoring agent product and preparation method thereof

With orange oil (75g) be added to contain 635g water, 297.50g maltodextrin, 123.25g Radix Acaciae senegalis (can from

Naturels International obtains) and the aqueous phase of 4.25g depolymerization citrus pectin.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 96.9%.

Embodiment 8: orange oil flavoring agent product and preparation method thereof

With orange oil (75g) be added to contain 635g water, 297.50g maltodextrin, 123.25g Radix Acaciae senegalis (can from

Naturels International obtains) and the aqueous phase of 4.25g beet pectin (can obtain production number XPQ EMP 5 from Degussa-France).Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 99.0%.

Embodiment 9: orange oil flavoring agent product and preparation method thereof

Orange oil (75g) is added to the aqueous phase that contains 635g water, 403.75g maltodextrin and 21.25g depolymerization citrus pectin.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 90.0%.

Embodiment 10: orange oil flavoring agent product and preparation method thereof

With orange oil (75g) be added to contain 635g water, 340.00g maltodextrin and 85.00g Radix Acaciae senegalis (can from

Naturels International acquisition) aqueous phase.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 91.0%.

Embodiment 11: orange oil flavoring agent product and preparation method thereof

Orange oil (75g) is added to the aqueous phase that contains 635g water and 425.50g maltodextrin.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 61.0%.

Embodiment 12: orange oil flavoring agent product and preparation method thereof

Orange oil (75g) is added to the aqueous phase that contains 635g water, 420.75g maltodextrin and 4.25g pectin.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 61.9%.

Embodiment 13: orange oil flavoring agent product and preparation method thereof

Orange oil (75g) is added to the aqueous phase that contains 635g water, 403.75g maltodextrin and 21.50g pectin.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 71.5%.

Embodiment 14: orange oil flavoring agent product and preparation method thereof

Orange oil (75g) is added to the aqueous phase that contains 635g water, 420.75g maltodextrin and 4.75g depolymerization citrus pectin.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 72.5%.

Embodiment 15: orange oil flavoring agent product and preparation method thereof

Orange oil (75g) is added to the aqueous phase that contains 635g water, 420.75g maltodextrin and 4.75g beet pectin (can obtain production number XPQ EMP 5) from Degussa-France.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 78.0%.

Embodiment 16: orange oil flavoring agent product and preparation method thereof

Orange oil (75g) is added to the aqueous phase that contains 635g water, 414.40g maltodextrin and 10.60g depolymerization citrus pectin.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 85.0%.

Embodiment 17: orange oil flavoring agent product and preparation method thereof

Orange oil (75g) is added to the aqueous phase that contains 635g water, 414.40g maltodextrin and 10.60g beet pectin (can obtain production number XPQ EMP 5) from Degussa-France.Method according to embodiment 5 is added to aqueous phase and dry with orange oil.The flavoring agent percent retention is about 87.0%.

Embodiment 18: contain beta-schardinger dextrin-and citral, as cyclodextrin inclusion complexes of the xanthan gum of emulsifying agent and preparation method thereof

Under atmospheric pressure, in the 1-L reactor, with 200g beta-schardinger dextrin-and 4.0g beet pectin (pectin: beta-schardinger dextrin-, 2 weight %; XPQ EMP 5 beet pectins can obtain from Degussa-France) do and mix, form dry blend.The 500g deionized water is added in the dry blend of beta-schardinger dextrin-and pectin, forms slurry or mixture.The 1-L reactor is provided with laboratory scale heating in water bath and chiller carries out heating and cooling.Mixture was heated 5 hours down and stirs at 55-60 ℃.Adding 27g citral (natural lemon aldehyde, SAP No.921565, lot number: 10000223137, can be from Citrus﹠amp; Allied obtains).Reactor is airtight, and the gained mixture stirred 5 hours down at about 55-60 ℃.Then the cooling segment of heating and cooling laboratory installation is opened, mixture is stirred down at about 5-10 ℃ spend the night.Then mixture is gone up spray drying at BUCHI B-191 spray dryerin lab (can be from Buchi, Switzerland obtains), the inlet temperature of spray dryer is about 210 ℃, and outlet temperature is about 105 ℃.The percent retention of citral is about 11.5 weight % in the described cyclodextrin clathrate.The dry powder of gained comprises 0.08 weight % surface oil (free citral).

Embodiment 19A: contain the citral of cyclodextrin encapsulation and the seasoning composition of excessive not compound cyclodextrin

The citral for preparing encapsulation according to embodiment 18 described methods.The dry powder of the citral that contains the cyclodextrin encapsulation of gained and extra beta-schardinger dextrin-done mix, with the complex of the embodiment 18 that obtains 1.0 weight % or in the powder mixture (" citral-cyclodextrin/cyclodextrin blend composition ") of gained the percentage by weight of citral be about 0.1 weight %.Is that about 0.2 weight % is added in the acidic beverages with citral-cyclodextrin/cyclodextrin blend composition with the percentage by weight that powder mixture (citral that is the beta-schardinger dextrin-encapsulation adds extra beta-schardinger dextrin-) accounts for the beverage gross weight.This oxytropism beverage provides the citral of about 10-15ppm and the beta-schardinger dextrin-of about 0.2 weight %.

Embodiment 19B: contain the citral of cyclodextrin encapsulation and the seasoning composition of excessive not compound cyclodextrin

The citral for preparing encapsulation according to embodiment 18 described methods.The dry powder of the citral that contains the cyclodextrin encapsulation of gained and extra beta-schardinger dextrin-done mix, the percentage by weight of citral is about 0.1 weight % (" citral-cyclodextrin/cyclodextrin blend composition ") in the powder mixture of gained.Citral-cyclodextrin/cyclodextrin blend composition is added in the beverage as head perfume (or spice).Is that about 0.2 weight % adds with citral-cyclodextrin/cyclodextrin blend composition with the percentage by weight that powder mixture (citral that is the beta-schardinger dextrin-encapsulation adds extra beta-schardinger dextrin-) accounts for the beverage gross weight.

The citral of the encapsulation described in the embodiment 18 obtains the active citral of 0.2 weight % with the extra dilution material/dry blend of extra excessive beta-schardinger dextrin-.The dilution material of this adding is necessary for study the effect of 0.1% beta-schardinger dextrin-in beverage when the citral of same level is provided.

Embodiment 19C: contain the citral of cyclodextrin encapsulation and the seasoning composition of excessive not compound hydroxypropyl beta-schardinger dextrin-

The citral for preparing encapsulation according to embodiment 18 described methods.Dry powder and hydroxypropyl beta-schardinger dextrin-(Aldrich Chemical with the citral that contains the cyclodextrin encapsulation of gained, Milwaukee WI) dried mixing, the percentage by weight of citral in the powder mixture of gained (" citral-cyclodextrin/cyclodextrin blend composition ") is about 0.1 weight %.Is that about 0.2 weight % is added in the acidic beverages with citral-cyclodextrin/cyclodextrin blend composition with the percentage by weight that powder mixture (citral that is the beta-schardinger dextrin-encapsulation adds extra hydroxypropyl beta-schardinger dextrin-) accounts for the beverage gross weight.The citral of 10-15ppm and the hydroxypropyl beta-schardinger dextrin-of about 0.2 weight % are provided like this.

The citral of the encapsulation described in the embodiment 18 obtains the active citral of 0.2 weight % with the extra dilution material/dry blend of extra excessive hydroxypropyl beta-schardinger dextrin-.The dilution material of this adding is necessary for study 0.1% effect of hydroxypropyl beta-schardinger dextrin-in beverage when the citral of same level is provided.

Embodiment 20: make citral stable with cyclodextrin

With citral (natural lemon aldehyde, SAP No.921565, lot number: 10000223137, can be from Citrus﹠amp; Allied obtains) in ethanol, cut, in citric acid, dilute the flavoring agent level that obtains expecting (for example, every 2L 0.6% citric acid 3mL (1% in ethanol citral); Called after in table 2 " contrast " or " new system contrast ").In contrast, add alpha-cyclodextrin or the beta-schardinger dextrin-of 0.1 weight % and 0.2 weight % then, and remain on 40 or 90 following 18 hours, 36 hours or 48 hours are to simulate different storage lives.As shown in table 2, every kind of arrangement for experiment, measure multi-form citral or feature and impact citrus flavors chemical compound (being neral, geranial and total citral, neral and geranial sum), comprise common citrus flavors abnormal flavour chemical substance (for example carveol, paracymene, p-cymen-8-ol, p, a-dimethyl styrene, 1,5-

Diene-8-alcohol 1 and a, 5-

Diene-8-alcohol 2) the long-pending counting of the asperities of mark (being designated as " CCH int std " in the table 2) in interior multiple other chemical compounds and chlorine cyclohexane extraction.As used herein, term " the long-pending counting of asperities " is used in reference to when using gas chromatography-mass spectrometry analysis (that is PEGASUS II time of-flight mass spectrometer (TOF-MS; Can be from LECO Corp., St.Joseph, Michigan obtains)) during analytic sample, the area under a curve of appropriate section among the gas chromatography figure.Target concentration is every part of beverage 10ppm in the chlorine cyclohexane extraction, with the long-pending counting of the asperities that is used for other related compounds of standardization.(Figure 28) as shown in table 2, adding cyclodextrin (particularly beta-schardinger dextrin-) has increased the amount of citral in the solution, has reduced the amount of the abnormal flavour that forms.Especially, along with the simulation storage life increases, observe this phenomenon (promptly along with the time increase, temperature raises, and contains particularly difference increasing between solution and the solution that contains contrast of beta-schardinger dextrin-of cyclodextrin).Comparison diagram 8 and Fig. 9 can see this point, and Fig. 8 and Fig. 9 show and add the inhibition that beta-schardinger dextrin-forms abnormal flavour.Relatively Figure 10 and Figure 11 can further see this point, and Figure 10 and Figure 11 show and add citral that the interval of beta-schardinger dextrin-in the back continue the contribution and the interval in the back of beverage do not had abnormal flavour.

Embodiment 21: the stability of the citral of cyclodextrin encapsulation in acid

(Figure 29) as shown in table 3 analyzes four kinds of multi-form acidic beverages samples.To prepare four kinds of drink samples in the multi-form low pH lemonade substrate of citral adding or " acid-sugar " solution (for example, 0.5% citric acid in the water and 8% sugar).By non-citral Citrus flavor ingredients being added to first kind of beverage of preparation in acid-sugar juice, it is called " no citral " in table 3.With 3mL (1% citral in ethanol) (citral of use is a natural lemon aldehyde, SAP No.921565, lot number: 10000223137, can be from Citrus﹠amp; Allied obtains)/2L 0.6% citric acid is added in acid-sugar juice, obtains second kind of beverage and " adds citral ", and citral concentration is about 10-15ppm.Citral-cyclodextrin/cyclodextrin blend composition that the embodiment 19A of 0.2 weight % is formed is added in acid-sugar juice, obtains the third beverage " 0.2%BCD-citral ", and citral concentration is about 10-15ppm.The water solublity Herba Rosmarini Officinalis of 0.2 weight % is added in described second kind of beverage, keeps citral concentration to be about 10-15ppm simultaneously, obtain the 4th kind of beverage " 0.2%WSR ".Water solublity Herba Rosmarini Officinalis used herein (" WSR ") refers to be used for the industry standard of stabilize water compatibility flavoring agent.

To all four kinds of beverages, measuring multi-form citral or feature impacts citrus flavors chemical compound (that is, sabinene, paracymene, neral and geranial) and comprises common citral abnormal flavour chemical substance (for example, p, a-dimethyl styrene, p-cymen-8-ol and 1,5-

Diene-8-alcohol 1) at the long-pending counting of the asperities of interior multiple other chemical compounds.40 °F following 1 day, 88 °F following 1 day, 40 °F following 2 days, 88 °F following 2 days, 40 °F following 7 days, 100 °F following 7 days, 40 °F following 14 days, 100 °F following 14 days, 40 °F following 21 days, 100 °F following 21 days to simulate different storage lives, measure afterwards.In addition, also measure one jar of Country

The long-pending counting of the asperities of above-claimed cpd in the board lemonade.

As table 3, Figure 12 and shown in Figure 13, under warm temperature (promptly 88 and 100), the third beverage comprises the long-pending counting of asperities (seeing Figure 12) of the citral similar to Other Drinks and other citrus flavors chemical compounds, but in all intervals, the long-pending counting of the asperities of the abnormal flavour of formation all is minimum (seeing Figure 13).Shown in Figure 14 and 15, under colder temperature (promptly 40), the third beverage comprises the long-pending counting of asperities (seeing Figure 14) of the citral similar to Other Drinks and other citrus flavors chemical compounds, but in all intervals, the long-pending counting of the asperities of the abnormal flavour that forms all is lower than second kind and the third beverage, identical with the long-pending counting of the asperities of the abnormal flavour that forms in the first kind of beverage that does not wherein add citral (see Table 2 and Figure 15 in " abnormal flavour of merging " row).

(Figure 29) as shown in table 3,1,5-

Diene-8-alcohol is first abnormal flavour that forms from unprotected citral, and it further is degraded to p-cymen-8-ol in time.Yet, comprise the abnormal flavour that does not have any in the third beverage of citral-cyclodextrin/cyclodextrin blend composition.In addition, the 0.2%BCD-citral is better than industry standard WSR to stablizing citral and other citrus flavors chemical compounds.

Embodiment 22: the stability of the citral of cyclodextrin encapsulation in acid

Add in acid-sugar juice by citral-cyclodextrin/cyclodextrin blend composition that the embodiment 19A of 0.3 weight % is formed and to obtain first kind of beverage, its in table 3 in the ID row note make " .3%BCD ", the citral concentration that obtains is about 20ppm.The WSR of 0.3 weight % is added in second kind of beverage of embodiment 21, keep citral concentration simultaneously, form second kind of beverage " .3%WSR " for about 10-15ppm.To described two kinds of beverages, measure multi-form citral or citrus flavors chemical compound (being sabinene, paracymene, neral and geranial) and comprise common citral abnormal flavour chemical substance (p for example, a-dimethyl styrene, p-cymen-8-ol and 1,5-

Diene-8-alcohol 1) at the long-pending counting of the asperities of interior multiple other chemical compounds.40 °F following 7 days, 100 °F following 7 days, 40 °F following 14 days, 100 °F following 14 days, 40 °F following 21 days with 100 °F following 21 days to simulate different storage lives, measure afterwards.(Figure 30) as shown in table 4, under warm temperature and colder temperature, comprise citral (the impacting citrus flavors) contribution of the reservation level similar in first kind of beverage, suppress but all have the enhancing that abnormal flavour is formed at all intervals to Other Drinks with other features.Owing to interact, observe the general minimizing of volatile substance with container for drink.Yet the very strong complex that forms between citral and the beta-schardinger dextrin-may be the partly cause that citral head space value reduces.But can taste citral, as shown in analysis of sensation (embodiment 34 and Figure 16 and 17) and as previously mentioned.

Embodiment 23: contain beta-schardinger dextrin-and Fructus Citri Limoniae oil 3X, as cyclodextrin inclusion complexes of the pectin of emulsifying agent and preparation method thereof

Under atmospheric pressure, in the 1-L reactor, with 400g beta-schardinger dextrin-and 8.0g beet pectin (pectin: beta-schardinger dextrin-, 2 weight %; XPQ EMP 5 beet pectins can obtain from Degussa-France) do and mix, form dry blend.The 1L deionized water is added in the dry blend of beta-schardinger dextrin-and pectin, forms slurry or mixture.The 1-L reactor is provided with laboratory scale heating in water bath and chiller carries out heating and cooling.With mixture stir about 30 minutes.California Fructus Citri Limoniae oil that adds 21g 3 * (promptly 3 times) (can be from Citrus﹠amp; Allied obtains).Reactor is airtight, the gained mixture was stirred 4 hours down at about 55-60 ℃.Then the cooling segment of heating and cooling laboratory installation is opened, mixture is stirred down at about 5-10 ℃ spend the night.Then mixture is gone up spray drying at BUCHI B-191 spray dryerin lab (can be from Buchi, Switzerland obtains), the inlet temperature of spray dryer is about 210 ℃, and outlet temperature is about 105 ℃.The percent retention of Fructus Citri Limoniae oil 3X is about 4.99 weight % in the cyclodextrin inclusion complexes.

Embodiment 24A: be used for the Fructus Citri Limoniae oil 3X that comprises the cyclodextrin encapsulation of beverage products and the seasoning composition of excessive not compound cyclodextrin

The dry powder of the Fructus Citri Limoniae oil 3X that comprises the cyclodextrin encapsulation of gained among the embodiment 23 and extra beta-schardinger dextrin-done mix, obtain that percentage by weight is the Fructus Citri Limoniae oil 3X of about 1 weight % in gained powder mixture (" Fructus Citri Limoniae oil 3X-cyclodextrin/cyclodextrin blend composition ").Be that about 0.05 weight %～about 0.30 weight % is added in the beverage with Fructus Citri Limoniae oil 3X-cyclodextrin/cyclodextrin blend composition with the percentage by weight that powder mixture (citral that is the beta-schardinger dextrin-encapsulation adds extra beta-schardinger dextrin-) accounts for the beverage gross weight then.Depend on the amount that is added to the powder mixture in the beverage, expect that this can provide the Fructus Citri Limoniae oil 3X of 20-30ppm and the percentage by weight that accounts for beverage is the beta-schardinger dextrin-of about 0.05 weight %～about 0.30 weight %.

Embodiment 24B: be used for the Fructus Citri Limoniae oil 3X that comprises the cyclodextrin encapsulation of beverage products and the seasoning composition of excessive not compound cyclodextrin

With the combined hybrid of citral-cyclodextrin inclusion complexes of the dry powder of embodiment 24 and embodiment 18, and mix (5 parts of citral/3 part 3X Fructus Citri Limoniaes), obtain 1% active flavoring agent in cyclodextrin with extra beta-schardinger dextrin-.This mixture can be used for to high acid content (acidity) spice and flavoring agent or expectation not too transparent, fruit juice sample outward appearance and having sends the stable skin new lemon feature of distinguishing the flavor of in the beverage of high stability.

Embodiment 25: contain beta-schardinger dextrin-and alpha-tocopherol, as pectin cyclodextrin inclusion complexes of emulsifying agent and preparation method thereof

Under atmospheric pressure, in the 1-L reactor, with 200g beta-schardinger dextrin-and 4.0g beet pectin (pectin: beta-schardinger dextrin-, 2 weight %; XPQ EMP 5 beet pectins can obtain from Degussa-France) do and mix, form dry blend.The 500g deionized water is added in the dry blend of beta-schardinger dextrin-and pectin, forms slurry or mixture.The 1-L reactor is provided with laboratory scale heating in water bath and chiller carries out heating and cooling.With mixture stir about 30 minutes.Add 23g D, L-alpha-tocopherol (Kosher, SAP#1020477 can obtain from BASF).Reactor is airtight, and mixture stirred down at about 55-60 ℃ spend the night.Then the cooling segment of heating and cooling laboratory installation is opened, mixture is stirred down at about 5-10 ℃ spend the night.Then mixture is gone up spray drying at BUCHI B-191 spray dryerin lab (can be from Buchi, Switzerland obtains), the inlet temperature of spray dryer is about 210 ℃, and outlet temperature is about 105 ℃.The percent retention of alpha-tocopherol is 10.31 weight % in the cyclodextrin inclusion complexes.1: 1 mol ratio of alpha-tocopherol should be corresponding to 27.52 weight % in the beta-schardinger dextrin-, but bibliographical information this be an oiliness pastel.10.31 the product of weight % is free-pouring dry powder, it easily is scattered in the water.When use was used (promptly reducing excessive not compound beta-schardinger dextrin-) with 0.1%, the alpha-tocopherol complex of 10.31 weight % easily was scattered in the water.

Embodiment 26: the compositions that is used for the alpha-tocopherol that contains the cyclodextrin encapsulation and the excessive not compound cyclodextrin of beverage products

The dry powder of the alpha-tocopherol that comprises the cyclodextrin encapsulation of gained among the embodiment 25 and extra beta-schardinger dextrin-done mix, obtain powder mixture, the percentage by weight of alpha-tocopherol is about 1 weight % in the powder mixture (" alpha-tocopherol-cyclodextrin/cyclodextrin blend composition ") of gained.Be that about 0.2 weight % be added in beverage as antioxidant and/or nutrient with the percentage by weight that powder mixture (alpha-tocopherol that is the beta-schardinger dextrin-encapsulation adds extra beta-schardinger dextrin-) accounts for the beverage gross weight with alpha-tocopherol-cyclodextrin/cyclodextrin blend composition then, add in the A.C.E. beverage (being A=vitamin A, C=vitamin C and E=vitamin E).Expect that this can provide the alpha-tocopherol of 10ppm and the percentage by weight that accounts for acidic beverages is the beta-schardinger dextrin-of about 0.2 weight %.

Embodiment 27: be used for the alpha-tocopherol that contains the cyclodextrin encapsulation of beverage products and the seasoning composition of excessive not compound cyclodextrin

The dry powder of the alpha-tocopherol that comprises the cyclodextrin encapsulation of gained among the embodiment 25 and other seasoning compositions (citral-beta-schardinger dextrin-that RUGEN forms according to the embodiment 18 and/or Fructus Citri Limoniae oil 3X-beta-schardinger dextrin-that forms according to embodiment 23) are mixed, do with extra beta-schardinger dextrin-then and mix, in the gained powder mixture, to obtain the flavor ingredients and the alpha-tocopherol of aspiration level.Powder mixture with gained is added in the beverage as antioxidant/nutrient/seasoning composition then.Expect that this can provide antioxidant/nutrient and the favourable taste profile and the beta-schardinger dextrin-(as 0.2 weight %) of appropriate amount of appropriate amount to beverage.In beverage, expect that this combination provides the stability of taste, turbidity (being fruit juice sample outward appearance), increase Citrus component, and demonstration can mix taste level, turbidity and functional advantage.Expect that this system is highly effective in salad dressing and flavoring agent mixture, partly cause is that enhanced Citrus taste protection adds the lipid protection of increase at least.

Embodiment 28: contain beta-schardinger dextrin-and white lemon oil, as the pectin of emulsifying agent with as cyclodextrin inclusion complexes of the xanthan gum of thickening agent and preparation method thereof

In the 1-L reactor, with 400g beta-schardinger dextrin-(the W7 beta-schardinger dextrin-can obtain from Wacker), 8g beet pectin (pectin: beta-schardinger dextrin-, 2 weight %; XPQ EMP 4 beet pectins can obtain from Degussa-France) and dried together the mixing of 1.23g xanthan gum (the KELTROL xanthan gum can obtain SAP No.15695 from CP Kelco), dry blend formed.The 800mL deionized water is added in the dry blend, forms slurry or mixture.The 1-L reactor is provided with laboratory scale heating in water bath and chiller carries out heating and cooling.With mixture stir about 30 minutes.(SAP No.1106890 can be from Degussa Flavors﹠amp to add 21g limette flavoring agent 043-03000; Fruit Systems obtains).Reactor is airtight, mixture was stirred 4 hours down at about 55-60 ℃.Then the cooling segment of heating and cooling laboratory installation is opened, mixture is stirred down at about 5-10 ℃ spend the night.Then mixture is gone up spray drying at BUCHI B-191 spray dryerin lab (can be from Buchi, Switzerland obtains), the inlet temperature of spray dryer is about 210 ℃, and outlet temperature is about 105 ℃.The percent retention of white lemon oil is about 4.99 weight % in the cyclodextrin inclusion complexes.

Embodiment 29: contain beta-schardinger dextrin-and white lemon oil, as the pectin of emulsifying agent with as cyclodextrin inclusion complexes of the xanthan gum of thickening agent and preparation method thereof

In the 1-L reactor, with 300g beta-schardinger dextrin-(the W7 beta-schardinger dextrin-can obtain from Wacker), 6g beet pectin (pectin: beta-schardinger dextrin-, 2 weight %; XPQ EMP 4 beet pectins can obtain from Degussa-France) and dried together the mixing of 1.07g xanthan gum (the KELTROL xanthan gum can obtain SAP No.15695 from CP Kelco), dry blend formed.The 750mL deionized water is added in the dry blend, forms slurry or mixture.The 1-L reactor is provided with laboratory scale heating in water bath and chiller carries out heating and cooling.With mixture stir about 30 minutes.(SAP#.1106890 can be from Degussa Flavors﹠amp to add 16g limette flavoring agent 043-03000; Fruit Systems obtains).Reactor is airtight, mixture was stirred 4 hours down at about 55-60 ℃.Then the cooling segment of heating and cooling laboratory installation is opened, mixture is stirred down at about 5-10 ℃ spend the night.Use high shear jar blender (HP 51PQ blender can be from Silverston Machines Ltd., and CheshamEngland obtains) with emulsifying mixture then.The percent retention of white lemon oil is about 5.06 weight % in the cyclodextrin inclusion complexes.

Embodiment 30: be used for the Fructus Citri Limoniae white lemon oil that contains the cyclodextrin encapsulation of beverage products and the seasoning composition of excessive not compound cyclodextrin

With the Fructus Citri Limoniae white lemon oil that comprises the cyclodextrin encapsulation of the dry powder of the Fructus Citri Limoniae white lemon oil that comprises the cyclodextrin encapsulation of embodiment 28 gained and/or embodiment 29 gained emulsion and extra beta-schardinger dextrin-do and mix, obtain powder mixture, the percentage by weight of Fructus Citri Limoniae white lemon oil is about 1 weight % in the powder mixture (" Fructus Citri Limoniae white lemon oil-cyclodextrin/cyclodextrin blend composition ") of gained.Be that about 0.05 weight %～about 0.30 weight % is added in the beverage with Fructus Citri Limoniae white lemon oil-cyclodextrin/cyclodextrin blend composition with the percentage by weight that powder mixture (the Fructus Citri Limoniae white lemon oil that is the beta-schardinger dextrin-encapsulation adds extra beta-schardinger dextrin-) accounts for the beverage gross weight then.Depend on the amount that is added to the powder mixture in the beverage, expect that this can provide the Fructus Citri Limoniae white lemon oil of 50-100ppm and the percentage by weight that accounts for beverage is the beta-schardinger dextrin-of about 0.05 weight %～about 0.30 weight %.

Embodiment 31: contain beta-schardinger dextrin-and citral, as the pectin of emulsifying agent with as cyclodextrin inclusion complexes of the xanthan gum of thickening agent and preparation method thereof

In the 1-L reactor, with 300g beta-schardinger dextrin-(the W7 beta-schardinger dextrin-can obtain from Wacker), 6g beet pectin (pectin: beta-schardinger dextrin-, 2 weight %; XPQ EMP 4 beet pectins can obtain from Degussa-France) and dried together the mixing of 0.90g xanthan gum (the KELTROL xanthan gum can obtain SAP No.15695 from CP Kelco), dry blend formed.The 575mL deionized water is added in the dry blend, forms slurry or mixture.The 1-L reactor is provided with laboratory scale heating in water bath and chiller carries out heating and cooling.With mixture stir about 30 minutes.(lot number 10000223137 can be from Citrus﹠amp for natural lemon aldehyde, SAP No.921565 to add the 18g citral; Allied obtains).Reactor is airtight, mixture was stirred 4 hours down at about 55-60 ℃.Then the cooling segment of heating and cooling laboratory installation is opened, mixture is stirred down at about 5-10 ℃ spend the night.Then with the mixture dimidiation.Half uses high shear jar blender (HP 51PQ blender can be from SilverstonMachines Ltd., and Chesham England obtains) emulsifying.Add 1 weight % Radix Acaciae senegalis in second half, and with the gained mixture with identical high shear jar blender emulsifying.The percent retention of citral is about 2.00 weight % in the cyclodextrin inclusion complexes.

Embodiment 32: the flavoring agent emulsion that is used for the citral that contains the cyclodextrin encapsulation of Foods or drinks product

One of emulsion or the both that to contain the citral of cyclodextrin encapsulation from two kinds of embodiment 31 gained directly add the Foods or drinks product, obtain having the stable prod of suitable taste profile.Emulsion is directly added in the Foods or drinks product, or be sprayed on the food matrix.

Embodiment 33: the flavoring agent emulsion that is used for the citral that contains the cyclodextrin encapsulation and the excessive not compound cyclodextrin of beverage products

To do with extra beta-schardinger dextrin-according to one of the emulsion of the citral that comprises the cyclodextrin encapsulation of embodiment 31 gained (or both mixture) and mix, obtain the flavoring agent emulsion, the percentage by weight of citral is about 1 weight % in the flavoring agent emulsion (" citral-cyclodextrin/cyclodextrin emulsion ") of gained.Is that about 0.05 weight %～about 0.30 weight % is added in the beverage with citral-cyclodextrin/cyclodextrin emulsion with the percentage by weight that flavoring agent emulsion (citral that is the beta-schardinger dextrin-encapsulation adds extra beta-schardinger dextrin-) accounts for the beverage gross weight.The amount that depends on the flavoring agent emulsion that is added in the beverage expects that this can provide the citral of 10-20ppm and the percentage by weight that accounts for beverage is the beta-schardinger dextrin-of about 0.05 weight %～about 0.30 weight %.Those skilled in the art will recognize that excessive not compound beta-schardinger dextrin-does not need at first to be added in the flavoring agent emulsion, but excessive not compound beta-schardinger dextrin-and the flavoring agent emulsion that forms according to embodiment 31 are added in the beverage products simultaneously.

Embodiment 34: the analysis of sensation that contains the lemonade beverage of citral of cyclodextrin encapsulation and control limes tuned water beverage relatively

The citral for preparing encapsulation according to embodiment 18 described methods.The dry powder of the citral that comprises the cyclodextrin encapsulation of gained and extra beta-schardinger dextrin-done mix, obtain powder mixture (" citral-cyclodextrin/cyclodextrin blend composition "), the percentage by weight of citral is about 1 weight % in the powder mixture of gained.Then with citral-cyclodextrin/cyclodextrin blend composition and the spray-dired Fructus Citri Limoniae oil flavoring agent of standard 073-00531 (32.0 parts) (Degussa Flavors﹠amp; Fruit Systems) mixes, form seasoning composition.Is that about 0.2 weight % adds in the lemonade beverage substrate with described seasoning composition with the percentage by weight that powder mixture (citral that is the beta-schardinger dextrin-encapsulation adds extra beta-schardinger dextrin-) accounts for the beverage gross weight.Lemonade beverage substrate comprises the seasoning composition of 10.5g, the sugar of 0.54g, the citric acid of 0.04g, sodium benzoate and the 88.79g water of 0.13g.This oxytropism beverage provides the citral of 10ppm and the beta-schardinger dextrin-of about 0.2 weight %.In the analysis of sensation shown in Figure 16 and Figure 17, this beverage is designated as " CD ".

With spray-dired citral (natural lemon aldehyde, SAP No.921565, lot number: 10000223137, can be from Citrus﹠amp; Allied obtains) and spray-dired Fructus Citri Limoniae oil flavoring agent 073-00531 (32.0 parts) (Degussa Flavors﹠amp; Fruit Systems) mixing prepares the first contrast seasoning composition.The flavoring agent for preparing spray-dried forms according to standard spray drying process well known by persons skilled in the art.The first contrast seasoning composition is added in the above-described same lemonade substrate beverage, and producing citral flavoring agent level is the first control limes tuned water beverage of 10ppm.Relatively the result of the analysis of sensation of the first control limes tuned water beverage and CD beverage is presented among Figure 16.Beverage after storing the aging beverage of 3 weeks simulation, 110 following dark places is carried out analysis of sensation.Analysis of sensation is a descriptive analysis that the sensation group that is made up of 6 trained expert tasters carries out, and uses unified method and reference standard.As shown in figure 16, compare with the first control limes tuned water beverage, the CD beverage has similar total flavour strength, similar skin flavor taste, stronger fresh lemon flavour, and lower oils and fats/waxiness, oxidation, phenol, 1-Phenylethanone. and Camphora sample taste.This analysis of sensation has been set forth cyclodextrin to the stable main ability of distinguishing the flavor of the flavoring agent citral and preventing to weaken and remove the abnormal flavour flavoring agent formation of the fresh lemon flavour in the lemonade beverage.

With the citral emulsion (natural lemon aldehyde, SAP No.921565, lot number: 10000223137, can be from Citrus﹠amp; Allied obtains) and Fructus Citri Limoniae oil flavoring agent 073-00531 (Degussa Flavors﹠amp; FruitSystems) mixing prepares the second contrast seasoning composition.Prepare emulsion according to standard emulsification method well known by persons skilled in the art.The second contrast seasoning composition is added in the above-described same lemonade substrate beverage, and forming citral flavoring agent level is the second control limes tuned water beverage of 10ppm.Relatively the result of the analysis of sensation of the second control limes tuned water beverage and CD beverage is presented among Figure 17.Beverage after storing the aging beverage of 3 weeks simulation, 110 following dark places is carried out analysis of sensation.Analysis of sensation is a descriptive analysis that the sensation group that is made up of 6 trained expert tasters carries out, and uses unified method and reference standard.As shown in figure 17, compare with the second control limes tuned water beverage, the CD beverage has similar total flavour strength, similar skin flavor taste, stronger fresh lemon flavour, and more weak oils and fats/waxiness, oxidation, phenol, 1-Phenylethanone. and Camphora sample taste.This analysis of sensation has been set forth cyclodextrin to the stable main ability of distinguishing the flavor of the flavoring agent citral and preventing to weaken and remove the abnormal flavour flavoring agent formation of the fresh lemon flavour in the lemonade beverage.As Figure 16 and illustrated in fig. 17 relatively, the second control limes tuned water beverage have a higher appreciable oxidation than the first control limes tuned water beverage with the 1-Phenylethanone. taste.This may be because the second control limes tuned water beverage is a liquid form, and this may cause the accelerated degradation of main flavor flavoring agent and abnormal flavour to form.

Embodiment 35: contain beta-schardinger dextrin-and citral, as the pectin of emulsifying agent with as cyclodextrin inclusion complexes of the xanthan gum of thickening agent and preparation method thereof

In the 5-L reactor, with 86.25g beta-schardinger dextrin-(the W7 beta-schardinger dextrin-can obtain from Wacker), 1.70g beet pectin (pectin: beta-schardinger dextrin-, 2 weight %; XPQ EMP 4 beet pectins can obtain from Degussa-France) and the matrix formulations of 0.35g xanthan gum (the KELTROL xanthan gum can obtain SAP No.15695 from CP Kelco) do together and mix, form dry blend.The 216.50mL deionized water is added in the dry blend, forms slurry or mixture.The 5-L reactor is provided with laboratory scale heating in water bath and chiller carries out heating and cooling.With mixture stir about 30 minutes.Adding 11.7g citral (natural lemon aldehyde, SAP No.921565, lot number: 10000223137, can be from Citrus﹠amp; Allied obtains).The scale of this matrix formulations is preparation 2200g.Reactor is airtight, mixture was stirred 4 hours down at about 55-60 ℃.Then the cooling segment of heating and cooling laboratory installation is opened, mixture is stirred down at about 5-10 ℃ spend the night.(Niro Corp.Columbia Maryland) goes up spray drying, and the inlet temperature of exsiccator is about 210 ℃, and outlet temperature is about 105 ℃ at Niro Basic Lab exsiccator with mixture then.The percent retention of citral is about 11.5 weight % in the cyclodextrin inclusion complexes.

Embodiment 36: contain beta-schardinger dextrin-and Fructus Citri Limoniae oil 3X, as the pectin of emulsifying agent with as cyclodextrin inclusion complexes of the xanthan gum of thickening agent and preparation method thereof

In the 5-L reactor, with 92.95g beta-schardinger dextrin-(the W7 beta-schardinger dextrin-can obtain from Wacker), 1.8g beet pectin (pectin: beta-schardinger dextrin-, 2 weight %; XPQ EMP 4 beet pectins can obtain from Degussa-France) and the matrix formulations of 0.35g xanthan gum (the KELTROL xanthan gum can obtain SAP No.15695 from CP Kelco) do together and mix, form dry blend.The 235.00mL deionized water is added in the dry blend, forms slurry or mixture.The 5-L reactor is provided with laboratory scale heating in water bath and chiller carries out heating and cooling.With mixture stir about 30 minutes.Adding 4.9g 3X California Fructus Citri Limoniae oil (can be from Citrus﹠amp; Allied obtains).The scale of this matrix formulations is preparation 2200g.Reactor is airtight, mixture was stirred 4 hours down at about 55-60 ℃.Then the cooling segment of heating and cooling laboratory installation is opened, mixture is stirred down at about 5-10 ℃ spend the night.(Niro Corp.Columbia Maryland) goes up spray drying, and the inlet temperature of spray dryer is about 210 ℃, and outlet temperature is about 105 ℃ at Niro Basic Lab exsiccator with mixture then.The percent retention of Fructus Citri Limoniae oil 3X is about 5 weight % in the cyclodextrin inclusion complexes.

Embodiment 37: the comparison that the lemonade beverage that contains the Fructus Citri Limoniae oil 3X of citral, cyclodextrin encapsulation of cyclodextrin encapsulation and excessive not compound cyclodextrin and the abnormal flavour of the contrast beverage that does not contain cyclodextrin form

89.79g water, 9.42g particulate sugar, 0.04g fine grained sodium citrate and 0.50g citric acid (anhydrous, thin) are mixed preparation lemonade substrate.Do not add antiseptic in the beverage, but beverage is carried out the pasteurization hot charging.The scale of this substrate is preparation 8L finished beverage.

Formation is labeled as the beverage of " CD ", and it contains the citral-cyclodextrin inclusion complexes (" citral-CD ") of with good grounds embodiment 35 formation and the Fructus Citri Limoniae oil 3X-cyclodextrin inclusion complexes (" Fructus Citri Limoniae-CD that forms according to embodiment 36 ").(073-00531 can be from DegussaFlavors﹠amp with the spray-dired Fructus Citri Limoniae oil of 32.00g; Fruit System acquisition), (073-00339 can be from DegussaF lavors﹠amp for 5.20g citral-CD; Fruit System acquisition), 3.20g Fructus Citri Limoniae-CD and the excessive not compound beta-schardinger dextrin-(the W7 beta-schardinger dextrin-can obtain from Wacker) of 59.60g are done and are mixed preparation " CD " seasoning composition.Described CD seasoning composition is mixed until all using about 30 mesh sieves to sieve in the lump.Then the 0.25gCD seasoning composition is added in the lemonade substrate preparation CD beverage and is packaged in the P.E.T. container.

The spray-dired Fructus Citri Limoniae oil of 32.00g, the spray-dired citral of 5.20g, the spray-dired Fructus Citri Limoniae oil 3X of 3.20g and 59.60g maltodextrin (are sprayed at all that (SAPNo.15433 can be from Tate﹠amp on the maltodextrin; LyIe obtains) do and mix, preparation contrast seasoning composition.According to standard spray drying process well known by persons skilled in the art with each spray-dired flavoring agent all with the maltodextrin spray drying.Described contrast seasoning composition does not contain cyclodextrin fully.0.25g is contrasted seasoning composition to be added in the lemonade substrate preparation contrast beverage (being called " protection ") and to be packaged in the P.E.T. container.

The flavoring agent reservation and the abnormal flavour formation of CD beverage are compared with the contrast beverage.(SPME is a kind of analytical headspace technique for Solid Phase Micro Extraction, the SPME) amount of mensuration citral and abnormal flavour, has automatization and the susceptiveness and the minimum sample preparation time of height with solid-phase microextraction.The sensitivity of the Asia 1,000,000 of SPME/part is identical with liquid-liquid extraction and distillation technique, but sample is not contacted extreme temperature, does not also use the solvent that may add pollutant in a large number and must remove before analysis.SPME uses with polymer (50/30 μ m DVB/Carboxen ^TM/ PDMS StableFlex ^TM, from Supelco, Bellefonte, PA obtains) and the 2cm fiber module of coating.Analytic sample is placed 10mL crimped lid (crimp-top) bottle.By making the head space that exists on the fiber contact analysis sample, Organic substance is trapped in the polymer, enters gas chromatogram (GC) or GC-mass spectrum (use PEGASUS III flight time mass spectrum (GC/TOF-MS in this experiment until thermal desorption; Can be from LECO Corp., St.Joseph, Michigan obtains) injection port.GC is Agilent 6890, analyzes on the 60m-x-0.32mm-DB-5 post of the thin film that has 1 micron thickness (can be from Restek Bellefonte, PA obtains) and carries out.The acquisition order of magnitude is 100,000～1,000,000 concentration effect easily.In this experiment, each sample of 2mL is placed the 10mL bottle, bottle was kept 10 minutes at 50 ℃ of following constant temperature, and extract 15 minutes with reach inferior 1,000,000/part sensitivity.

Flavoring agent reservation and total abnormal flavour increase in unprotected beverage and the CD beverage under Figure 18 has provided 88.(light post is represented total seasoning feature (that is, all flavor ingredients of detection), and dark post is represented total abnormal flavour growth in unprotected beverage and the CD beverage).As shown in figure 18, the CD beverage keeps obviously longer bigger flavoring agent feature than unprotected beverage, and the total abnormal flavour that can be observed the CD beverage forms and is lower than unprotected beverage.Flavoring agent is moved in the packaging material on the books in the business information of document and package design company.Preventing or regulating very importantly of flavoring agent migration and also has unexpected advantage except the stability of flavoring agent.In time (promptly two kinds of beverages 88 °F store 21 days down after, 88 °F store 33 days down after and 88 °F store 42 days down after) formation of measuring four types abnormal flavour, the result is presented among Figure 19.That is, four kinds of abnormal flavour of analysis are melilotal, p-cymen-8-ol, 1,5-

Diene-8-alcohol 1 and 1,5-

Diene-8-alcohol 2.As shown in figure 19, the level of all four kinds of abnormal flavour that the CD beverage forms all is lower than unprotected beverage, and particularly the p-cymen-8-ol of Xing Chenging is lower than unprotected beverage.From the scheme of Fig. 7, select abnormal flavour then.Yet paracresol is owing to the reason of its highly-water-soluble is extremely difficult by the SPME detection, thereby paracresol is characterized by sense organ group.Referring to, for example, Figure 16 and Figure 17, wherein paracresol is included as the phenol characteristics/properties.

Embodiment 38: the protective effect that beta-schardinger dextrin-provides in " Exposure to Sunlight " phenomenon

In beverage products, introduce other protective effects that cyclodextrin provides for research, carry out " Exposure to Sunlight " (photooxidation) phenomenon preliminary study.Particularly, studied the sunlight contact of commodity.As described in embodiment 20, with citral (natural lemon aldehyde, SAP No.921565 can be from Citrus﹠amp; The Allied acquisition) in ethanol, is diluted to 1.0% level.Prepare two kinds of simulation beverage substrate: contrast, 0.6% citric acid in water and protection, 0.6% citric acid in water and 0.2% beta-schardinger dextrin-.1.0% citral in alcoholic solution is added in each beverage substrate with 0.1% (10ppm citral); Two kinds of simulation beverages all place the glass juice bottle, place the laboratory window, and the contact southeast was to strong sunlight 5 days.The bipartite carafe of respectively simulating is placed baking oven, and remain under 110 °F.After 5 days, sampling from each bottle is analyzed with the identical head space method of using all the time in this research (SPME).These results are presented among Figure 20 with illustrated form.About the information of citral light stability seldom, but do not protect the detection of abnormal flavour in the sample to show to have closely similar chemical compound and concentration thereof.Therefore, infer in acidic matrix in the catalytic degraded of light and heat similar reaction path work (referring to for example Fig. 7).In Figure 20, not compare with protecting sample (being labeled as CIT), the sample of protection (being labeled as BCD) shows does not have the reactive intermediate abnormal flavour right

The formation of diene-8-alcohol.It also is tangible that the formation that is further illustrated in paracymene in the protection system reduces more.

Embodiment 39: citral, color and vitamin content stable that uses cyclodextrin

The 0.2 weight % " citral-cyclodextrin/beta-schardinger dextrin-blend composition " and red 40 colors of 0.01 weight % that in the commercially available vitamin enrichment beverage of buying in local grocery store (GLACEAU multi-v lemonade (a-zinc)), add embodiment 18.Put back in the former container mixture and sealing.Air-tight bottle placed face south window 5-6 week or until noticing change color.

Embodiment 40: citral, color and vitamin content stable that uses cyclodextrin

The 0.2 weight % " citral-cyclodextrin/HP beta-schardinger dextrin-blend composition " and red 40 colors of 0.01 weight % that in the commercially available vitamin enrichment beverage of buying in local grocery store (GLACEAU multi-v lemonade (a-zinc)), add embodiment 19A.Put back in the former container mixture and sealing.Air-tight bottle placed face south window 5-6 week or until noticing change color.Excessive beverage storing frozen in glass.The results are shown in table 5 (Figure 31).The visual pattern of bottled drink is shown among Figure 21-23.Bottle shows that red 40 colors are through being exposed to light degradation.Use hydroxypropyl-beta-schardinger dextrin-color stability best.

Embodiment 40A: citral the stablizing of using cyclodextrin to sunlight

Study the citral product of the encapsulation of embodiment 19 over 7 days by in following examples, being exposed to summer sunlight, but adopt the cyclodextrin of two kinds of variable concentrations to monitor the light and heat oxidation product.Verified before, photooxidation follow with acid medium in the similar response path of thermal oxide, and use beta-schardinger dextrin-that protection is provided; There is not this category information to exist for hydroxypropyl-beta-schardinger dextrin-.Research citral complex under two different concentration, and be designed to delivered constant citral level when using in the acidic beverages substrate that constitutes by 10% sucrose and 0.5% citric acid at 0.1 weight % or 0.2 weight %.0.1 weight % citral in the ethanol is with comparing.Every kind of sample of preparation 500ml, and be divided into 6, the 4oz sample, not have the head space and the sealing of permission.The SPME and the LECOPegasus III GC/TOF-MS of report analyze before using; Using " Latin Square " sampling plan that each sample is carried out three times analyzes.The result of typical case's abnormal flavour is presented among Figure 24-26.In the beverage of beta-schardinger dextrin-protection, do not detect p-alpha-alpha-dimethyl styrene.

Embodiment 41: contain beta-schardinger dextrin-and diformazan hydroxyl furanone, as cyclodextrin inclusion complexes of the pectin of emulsifying agent and preparation method thereof

Under atmospheric pressure, in the 1-L reactor, with 200g beta-schardinger dextrin-and 4.0g beet pectin (pectin: beta-schardinger dextrin-, 2 weight %; XPQ EMP 5 beet pectins can obtain from Degussa-France) do and mix, form dry blend.The 500g deionized water is added in the dry blend of beta-schardinger dextrin-and pectin, forms slurry or mixture.The 1-L reactor is provided with laboratory scale heating in water bath and chiller carries out heating and cooling.Mixture was heated 0.5 hour down and stirs at 50 ℃.Adding 150g 15% natural diformazan hydroxyl furanone (alcoholic solution of (4-hydroxyl-2,5-dimethyl-3 (2H) furanone) FEMA#3174, from Alfrebro, Cargill branch, Monroe, Ohio obtains).Reactor is airtight, and the gained mixture stirred 4 hours down at about 50 ℃.Then the cooling segment of heating and cooling laboratory installation is opened, mixture is stirred down at about 5-10 ℃ spend the night.Then mixture is gone up spray drying at BUCHIB-191 spray dryerin lab (can be from Buchi, Switzerland obtains), the inlet temperature of spray dryer is about 210 ℃, and outlet temperature is about 105 ℃.The percent retention of diformazan hydroxyl furanone is 4.6 weight % (45.5% yields) in the described cyclodextrin clathrate.

Embodiment 42: contain the diformazan hydroxyl furanone of cyclodextrin encapsulation and the seasoning composition of excessive not compound cyclodextrin

The diformazan hydroxyl furanone for preparing encapsulation according to embodiment 41 described methods.The dry powder of the diformazan hydroxyl furanone that contains the cyclodextrin encapsulation of gained and extra beta-schardinger dextrin-done mix, the percentage by weight of diformazan hydroxyl furanone is about 0.05 weight % in the powder mixture of gained (" diformazan hydroxyl furanone-cyclodextrin/cyclodextrin blend composition ").Is that about 0.2 weight % is added in the cream soda with diformazan hydroxyl furanone-cyclodextrin/cyclodextrin blend composition with the percentage by weight that powder mixture (the diformazan hydroxyl furanone that is the beta-schardinger dextrin-encapsulation adds extra beta-schardinger dextrin-) accounts for the beverage gross weight.This provides the diformazan hydroxyl furanone of about 5-10ppm and the beta-schardinger dextrin-of about 0.2 weight % to this acidic beverages.This compositions is used to protect flavoring agent such as cis-3-hexenol, diformazan hydroxyl furanone, vanillin, frambinone (raspberry ketone), ionone etc.; Color, as RED 40, and prevent flavoring agent (and/or) other compositions move in the plastic containers.

Embodiment 43: contain the diformazan hydroxyl furanone of cyclodextrin encapsulation and the seasoning composition of excessive not compound cyclodextrin

The diformazan hydroxyl furanone for preparing encapsulation according to embodiment 41 described methods.The dry powder of the diformazan hydroxyl furanone that contains the cyclodextrin encapsulation of gained and extra HP-beta-schardinger dextrin-done mix, the percentage by weight of diformazan hydroxyl furanone is about 0.05 weight % in the powder mixture of gained (" diformazan hydroxyl furanone-cyclodextrin/HP-beta-schardinger dextrin-blend composition ").Is that about 0.2 weight % is added in the cream soda with diformazan hydroxyl furanone-cyclodextrin/HP-beta-schardinger dextrin-blend composition with the percentage by weight that powder mixture (the diformazan hydroxyl furanone that is the beta-schardinger dextrin-encapsulation adds extra beta-schardinger dextrin-) accounts for the beverage gross weight.This provides the diformazan hydroxyl furanone of about 5-10ppm and the beta-schardinger dextrin-of about 0.2 weight % to this acidic beverages.This compositions is used to protect flavoring agent such as cis-3-hexenol, diformazan hydroxyl furanone, vanillin, frambinone, ionone etc.; Color, as RED 40, and prevent flavoring agent (and/or) other compositions move in the plastic containers.

Embodiment 44: analysis to measure

Producing preliminary analysis for the preparation in embodiment 39,40,42 and 43 distributes.Take out the 2ml sample from container, to carry out the headspace analysis described in the embodiment 37 (although will analyze different flavoring agent chemical compound and abnormal flavour).Detect the concentration of monitoring vanillin and Red 40 by HPLC and UV.

Embodiment 45: form the bulky grain cyclodextrin inclusion complexes with arachidonic acid (40%)

At industrial mixers (the Kitchen AidProline that is equipped with glove bag (glove bag) so that inert atmosphere to be provided, Kitchen Aid, St.Joseph.Michigan) in, with 1000, the 0000g beta-schardinger dextrin-under low speed with 800,0000g distilled water and 20,00g beet pectin (2.0 weight % pectin, XPQ EMP 4 beet pectins obtain from Degussa-France) mixed 30 minutes, in dough shape mixture, form pastel.Mixture was mixed 2 minutes under high speed, remove the dissolved air of existence.Slowly add 300, (Cargill, Minneapolis MN), mixed 90 minutes 0000g arachidonic acid (40%) simultaneously.

Mixture transferred in two dishes carry out vacuum drying.Whole process is carried out under blanket of nitrogen.Mixture under 79 ℃ and 0.1torr dry 9 hours.The product of gained is a fine powder, the ARA that 36 weight % keep; Do not observe surface oil.

Embodiment 46: use in infant formula

To be added in the infant formula according to the arachidonic acid of the cyclodextrin encapsulation of embodiment 45 preparation.

All patents that this paper quotes, publication and list of references full content are incorporated this paper by reference into.Have under the situation of conflicting with patent, publication and the list of references of introducing in content disclosed herein, be as the criterion with content disclosed herein.

Claims (58)

1. product that contains with compound object of cyclodextrin and object catabolite, its object was at least about 5: 1 with object catabolite ratio when described product stored at least about 30 days under at least about 88 temperature.

2. product as claimed in claim 1, object is at least about 10: 1 with object catabolite ratio when wherein storing at least about 30 days under at least about 88 temperature.

3. product as claimed in claim 1, object is at least about 5: 1 with object catabolite ratio when wherein storing at least about 60 days under at least about 88 temperature.

4. product as claimed in claim 1, object is at least about 5: 1 with object catabolite ratio when wherein storing at least about 90 days under at least about 88 temperature.

5. product that contains with the compound object of cyclodextrin, the concentration of object in described product reduces and is no more than about 25% when wherein storing about 30 days under at least about 88 temperature.

6. product as claimed in claim 5, described concentration reduction is no more than about 45% when wherein storing about 30 days under at least about 88 temperature.

7. product as claimed in claim 5, described concentration reduction is no more than about 25% when wherein storing about 90 days under at least about 88 temperature.

8. product that contains with the compound object of cyclodextrin, the concentration of wherein said object reduces in time, and wherein after about 30 days the concentration of described object in described product be lower than the concentration of described object in contrast and reduce.

9. product that contains with compound object of cyclodextrin and object catabolite, wherein the concentration that exists at described object catabolite after about 30 days is lower than the concentration of described object catabolite in contrast after about 30 days.

10. a product that contains with compound object of cyclodextrin and object catabolite is wherein compared with the formation of object catabolite in contrast, and the formation of described object catabolite is reduced by at least about 200%.

11. product as claimed in claim 10 is wherein compared with the formation of object catabolite in contrast, the formation of described object catabolite is reduced by at least about 500%.

12. a product that contains polyunsaturated fatty acid and cyclodextrin, wherein said polyunsaturated fatty acid and described cyclodextrin are compound.

13. product as claimed in claim 12, wherein said polyunsaturated fatty acid is an omega-fatty acid.

14. as each described product in the claim 1～13, wherein said cyclodextrin comprises beta-schardinger dextrin-.

15. product as claimed in claim 14, wherein said beta-schardinger dextrin-comprises the beta-schardinger dextrin-of replacement.

16. product as claimed in claim 15, the beta-schardinger dextrin-of wherein said replacement comprises the hydroxypropyl beta-schardinger dextrin-.

17. product as claimed in claim 16, wherein said beta-schardinger dextrin-comprises the mixture of hydroxypropyl beta-schardinger dextrin-and beta-schardinger dextrin-.

18. product as claimed in claim 17, the existence ratio of wherein said hydroxypropyl beta-schardinger dextrin-and described beta-schardinger dextrin-is about 2: 1～about 1: 30.

19. as each described product in the claim 1～18, wherein said product contains excessive cyclodextrin.

20. as each described product in claim 1～11 and 13～19, wherein said object comprises flavoring agent.

21. product as claimed in claim 20, wherein said flavoring agent comprises citral.

22. as each described product in claim 1～11 and 13～19, wherein said object comprises coloring agent.

23. as each described product in claim 1～11 and 13～19, wherein said object comprises nutrient.

24. as each described product in the claim 1～23, wherein said product is a beverage.

25. product as claimed in claim 24, wherein said beverage is a soda pop.

26. as each described product in the claim 1～23, wherein said product is a food.

27. as each described product in the claim 1～26, wherein the amount of cyclodextrin is about 0.05 weight %～about 0.50 weight %.

28. product as claimed in claim 27, wherein the amount of cyclodextrin is about 0.2 weight %.

29. product as claimed in claim 27, wherein the amount of cyclodextrin is about 0.1 weight %.

30. as each described product, wherein cyclodextrin in claim 1～18 and 20～29: object is than being about 1: 1.

31. as each described product, wherein cyclodextrin in the claim 1～29: object is than greater than about 1: 1.

The method of degrading 32. an object that reduces in the product is passed in time, described method comprises and will be added in the described product with the compound object of cyclodextrin, wherein said object is compound with cyclodextrin in the presence of emulsifying agent, and wherein compared with the control, the degraded of described object is owing to the compound of described object and cyclodextrin reduces about 25%.

33. method as claimed in claim 32, the degraded of wherein said object causes owing to being exposed to light.

34. the method that the concentration of object in product reduces is passed in a minimizing in time, described method comprises: will be added in the described product with the compound object of cyclodextrin, wherein compared with the control, the concentration of described object reduces owing to the compound of described object and cyclodextrin is reduced by at least about 25%.

35. method as claimed in claim 34, the degraded of wherein said object causes owing to being exposed to light.

36. an improvement is exposed to the method for stability of the flavoring agent of light time product, described method comprises and will be added in the described product with the compound object of cyclodextrin that wherein compared with the control, the improved stability of described flavoring agent is at least about 25%.

37. method as claimed in claim 36, wherein compared with the control, the improved stability of described flavoring agent is at least about 45%.

Not compound polyunsaturated fatty acid is mixed with cyclodextrin and form complex 38. a method for preparing the product that contains polyunsaturated fatty acid, described method comprise; With described complex is added in the described product.

39. method as claimed in claim 38, wherein said polyunsaturated fatty acid is compound with cyclodextrin in the presence of emulsifying agent.

40. as each described method in the claim 32～37, wherein said object is compound with cyclodextrin in the presence of emulsifying agent.

41. as each described method in the claim 32～40, wherein cyclodextrin comprises beta-schardinger dextrin-.

42. method as claimed in claim 41, wherein beta-schardinger dextrin-comprises the beta-schardinger dextrin-of replacement.

43. method as claimed in claim 42, wherein the beta-schardinger dextrin-of Qu Daiing comprises the hydroxypropyl beta-schardinger dextrin-.

44. method as claimed in claim 41, wherein beta-schardinger dextrin-comprises the mixture of hydroxypropyl beta-schardinger dextrin-and beta-schardinger dextrin-.

45. method as claimed in claim 44, wherein the existence of hydroxypropyl beta-schardinger dextrin-and beta-schardinger dextrin-ratio is about 2: 1～about 1: 30.

46. as each described method in the claim 32～45, wherein said product contains excessive cyclodextrin.

47. as each described method in the claim 32～45, wherein said object comprises flavoring agent.

48. method as claimed in claim 47, wherein said flavoring agent comprises citral.

49. as each described method in the claim 32～46, wherein said object comprises coloring agent.

50. as each described method in the claim 32～46, wherein said object comprises nutrient.

51. as each described method in the claim 32～50, wherein said product is a beverage.

52. method as claimed in claim 51, wherein said beverage is a soda pop.

53. as each described method in the claim 32～50, wherein said product is a food.

54. as each described method in the claim 32～53, wherein the amount of cyclodextrin is about 0.05 weight %～about 0.50 weight %.

55. method as claimed in claim 54, wherein the amount of cyclodextrin is about 0.2 weight %.

56. method as claimed in claim 54, wherein the amount of cyclodextrin is about 0.1 weight %.

57. as each described method, wherein cyclodextrin in claim 32～45 and 47～56: object is than being about 1: 1.

58. as each described method, wherein cyclodextrin in the claim 32～56: object is than greater than about 1: 1.

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