A trichlorosucrose complex, a method for preparing the same, and an atomized flavorant

Abstract

The present application provides a sucralose complex, a preparation method thereof and an atomized essence. The organic complex is prepared by sucralose, organic acid and polyphenol hydroxyl substance, so as to stabilize the glycosidic bond of sucralose molecule, reduce the probability of cracking, reduce the production of sucralose cracking intermediates, and meanwhile, the polyphenol hydroxyl substance and the intermediates form an adduct to inhibit further degradation, so as to achieve the purpose of inhibiting HCl release, thereby preventing glycerol in the atomized essence from substituting with HCl to generate toxic chloropropanol substances, and improving the safety of the atomized essence in use.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of sweeteners, in particular to a sucralose complex, a preparation method thereof and an atomized essence. BACKGROUND

[0002] Artificial sweeteners are a class of widely used in food, beverage, medicine and personal care products of synthetic or semi-synthetic instead of sucrose organic compounds, most of the artificial sweeteners are hardly converted by the human body, so they are called non-calorie sugar, including saccharin, aspartame, neotame, acesulfame and sucralose. Among them, the sweetness of sucralose can reach about 600 times of sucrose, its high sweetness, pure sweetness, safety and other characteristics make it one of the most ideal sweeteners.

[0003] In recent years, due to the need of the taste of atomized essence, sucralose is introduced into the flavoring of atomized essence, but because sucralose has heat-sensitive characteristics, it is easy to crack under the working temperature (about 200-270℃) of electronic heating equipment, and because of the presence of glycerol in atomized essence, sucralose will crack and chemically react with glycerol when heated in atomized essence, producing chloropropanol chemical components released into aerosol, among which 3-MCPD is the main one; 3-MCPD has nephrotoxicity, reproductive toxicity, neurotoxicity, immunotoxicity, mutagenicity, etc. In 1993, the World Health Organization warned about the toxicity of chloropropanol substances, and since then, the European Commission Committee on Food Science has evaluated the toxicity of chloropropanol substances, considering it a carcinogen, and its minimum threshold should be no detection, among which 3-MCPD is the most toxic.

[0004] Because sucralose is widely used in the flavoring of atomized essence, and there is no better substitute in the short term, in addition, its safety at low temperature makes people ignore its danger under harsh conditions, so there is a safety problem in the use of atomized essence. SUMMARY

[0005] The main purpose of the present application is to provide a sucralose complex, which aims to improve the safety of existing atomized essence.

[0006] To achieve the above purpose, the first aspect of the present application provides a sucralose complex, which comprises sucralose and additives, the additives comprising organic acid and polyphenol hydroxyl substances, wherein the mass percentage of sucralose is 70% to 95%, the mass percentage of organic acid is 1% to 15%, and the mass percentage of polyphenol hydroxyl substances is 0.1% to 5%.

[0007] Optionally, the organic acid comprises one or more of strawberry acid, benzoic acid, salicylic acid, coffee acid, dodecanoic acid, hexadecanoic acid, octadecanoic acid, decanoic acid, phenylacetic acid, cinnamic acid.

[0008] Optionally, the organic acid comprises one or more of tartaric acid, malic acid, fumaric acid, succinic acid, ethanedioic acid, propanedioic acid, pentanedioic acid, hexanedioic acid, phthalic acid, maleic acid, hexadienoic acid.

[0009] Optionally, the organic acid comprises one or more of citric acid, isocitric acid, propane-1,2,3-tricarboxylic acid, homocitric acid, homoisocitric acid, trimesic acid.

[0010] Optionally, the polyphenol hydroxyl substance comprises one or more of catechin, isoflavone, anthocyanin, cocoa polyphenol, curcumin, citraurin, quercetin, rutin, resveratrol, hesperidin, shikonin, pelargonidin, methylic anthocyanin, delphinidin, malvidin, flavonol, kaempferol, myricetin, apigenin, lutein, naringenin, daidzein, epicatechin, estrogens.

[0011] Optionally, the polyphenol hydroxyl substance comprises one or more of chlorogenic acid, hydroxybenzoic acid, protocatechuic acid, gallic acid, p-hydroxybenzoic acid, coumaric acid, coffee acid, and ferulic acid.

[0012] Optionally, the additive further comprises an organic salt, the organic salt being a sodium salt or a potassium salt of the water-soluble organic acid, and the mass percentage of the organic salt being 1% to 10%.

[0013] The second aspect of the present application provides a preparation method of a sucralose complex, comprising:

[0014] S1: dissolving sucralose solid in a solvent preheated to 40-60℃;

[0015] S2: under stirring, adding organic acid, organic salt, and polyphenol hydroxyl substance to make them completely dissolved;

[0016] S3: cooling to 20-10℃ at a cooling rate of 0.5-5℃ / min;

[0017] S4: complex culture at -4℃ to 4℃ for 3-4 hours;

[0018] S5: suction filtration;

[0019] S6: drying to obtain the sucralose complex.

[0020] The third aspect of the present application provides an atomized type essence, comprising the sucralose complex of any one of the first aspect.

[0021] The technical scheme of the present application forms an organic complex by preparing the sucralose with organic acid and polyphenol hydroxyl substances, thereby stabilizing the glycosidic bond of the sucralose molecule, reducing the probability of its cleavage, and reducing the generation of the sucralose cleavage intermediate; meanwhile, the polyphenol hydroxyl substances form an adduct with the intermediate to inhibit its further cleavage, achieving the purpose of inhibiting the release of HCl, thereby preventing the substitution reaction of glycerol in the atomized flavor with HCl to generate toxic chloropropanol substances, and improving the safety of the atomized flavor. BRIEF DESCRIPTION OF DRAWINGS

[0022] In order to more clearly illustrate the technical solutions in the embodiments of the present application or the prior art, the following will briefly introduce the drawings needed to be used in the embodiments or the prior art description. Obviously, the drawings in the following description only represent some of the embodiments of the present application, and other drawings can be obtained by those skilled in the art without creative labor on the basis of the drawings shown.

[0023] Figure 1 The flowchart of the preparation method of the sucralose complex of the present application is shown.

[0024] The implementation, functional features and advantages of the present application will be further described with reference to the embodiments and the drawings. DETAILED DESCRIPTION

[0025] The technical solutions in the embodiments of the present application will be described clearly and completely below with reference to the drawings in the embodiments of the present application. Obviously, the described embodiments only represent some of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative labor fall within the scope of the present application.

[0026] The present application provides a sucralose complex which is chemically stable and not easy to decompose at high temperature, and is safe and reliable for use in atomized flavor.

[0027] In the embodiments of the present application, the first aspect of the present application provides a sucralose complex comprising sucralose and additives, the additives comprising organic acid and polyphenol hydroxyl substances, wherein the mass percentage of the sucralose is 70% to 95%, the mass percentage of the organic acid is 1% to 15%, and the mass percentage of the polyphenol hydroxyl substances is 0.1% to 5%.

[0028] Specifically, the meaning of the polyphenol hydroxyl substances in the embodiments of the present application is that the number of phenolic hydroxyl groups in the substances is greater than or equal to 1.

[0029] Specifically, sucralose can be thermally cracked at 119℃, while the working temperature of the electronic heating device of the atomized flavor essence, such as an electronic cigarette, is about 200-270℃. In theory, one molecule of sucralose releases three molecules of HCl, and the glycerol in the electronic cigarette oil is extremely easy to undergo a substitution reaction with HCl to generate chloropropanol substances.

[0030] Specifically, the thermal cracking of sucralose will undergo a series of processes. First, one molecule of sucralose absorbs heat and becomes unstable, causing the glycosidic bond to break, generating one molecule of 4-chloro-galactosyl cation and one molecule of 1,6-dichloro-1,6-dideoxy-fructose. Among them, the key reaction intermediate 4-chloro-galactosyl cation has a very unstable oxonium ion structure, which will further undergo intramolecular nucleophilic attack of the hydroxyl group to cause molecular rearrangement, producing a more stable structure, and then removing two molecules of water and one molecule of HCl to become a stable structure of levoglucosenone.

[0031] The technical scheme of the present application forms an organic complex by preparing sucralose with organic acids and polyphenol hydroxyl substances, thereby stabilizing the glycosidic bond of the sucralose molecule, reducing the probability of its cracking, reducing the generation of 4-chloro-galactosyl cation, an intermediate of sucralose cracking, and at the same time, the polyphenol hydroxyl substance forms an adduct with the intermediate to inhibit its further degradation, achieving the purpose of inhibiting the release of HCl, thereby preventing the substitution reaction of glycerol in the atomized flavor essence with HCl to generate toxic chloropropanol substances, thereby improving the safety of the atomized flavor essence.

[0032] Optionally, the organic acid is a water-soluble organic acid.

[0033] Optionally, the organic acid includes one or more of strawberry acid, benzoic acid, salicylic acid, coffee acid, dodecanoic acid, hexadecanoic acid, octadecanoic acid, decanoic acid, phenylacetic acid, and cinnamic acid.

[0034] Specifically, strawberry acid, benzoic acid, salicylic acid, coffee acid, dodecanoic acid, hexadecanoic acid, octadecanoic acid, decanoic acid, phenylacetic acid, and cinnamic acid are monobasic acids.

[0035] Optionally, the organic acid includes one or more of tartaric acid, malic acid, fumaric acid, succinic acid, ethanedioic acid, propanedioic acid, pentanedioic acid, hexanedioic acid, phthalic acid, maleic acid, and hexadienedioic acid.

[0036] Specifically, tartaric acid, malic acid, fumaric acid, succinic acid, ethanedioic acid, propanedioic acid, pentanedioic acid, hexanedioic acid, phthalic acid, maleic acid, and hexadienedioic acid are dibasic acids.

[0037] Optionally, the organic acid includes one or more of citric acid, isocitric acid, propane-1,2,3-tricarboxylic acid, homocitric acid, homoisocitric acid, and trimesic acid.

[0038] Specifically, citric acid, isocitric acid, propane-1,2,3-tricarboxylic acid, homocitric acid, homoisocitric acid and trimesic acid are triprotic acids. Triprotic acids have more carboxyl groups, which can form stronger intermolecular forces with the chlorine atoms of sucralose, and are better for stabilizing the molecular structure of sucralose.

[0039] Optionally, the polyphenol hydroxyl substance includes one or more of catechin, isoflavone, anthocyanin, cocoa polyphenol, curcumin, flavanone, quercetin, rutin, resveratrol, hesperidin, shikonin, pelargonidin, methylene cyanine, delphinidin, malvein, flavonol, kaempferol, myricetin, apigenin, lutein, naringenin, daidzein, epicatechin, and estrogens.

[0040] Optionally, the polyphenol hydroxyl substance includes one or more of chlorogenic acid, hydroxybenzoic acid, protocatechuic acid, gallic acid, p-hydroxybenzoic acid, coumaric acid, caffeic acid, and ferulic acid.

[0041] Specifically, chlorogenic acid, hydroxybenzoic acid, protocatechuic acid, gallic acid, p-hydroxybenzoic acid, coumaric acid, caffeic acid and ferulic acid have both the properties of organic acids and the properties of polyphenols, so they can not only stabilize the glycosidic bond of sucralose, but also prevent the further cleavage of sucralose intermediates, and the effect is better than that of other polyphenol hydroxyl substances.

[0042] Specifically, coumaric acid includes three isomers of o-coumaric acid, m-coumaric acid and p-coumaric acid.

[0043] Optionally, the additive further includes an organic salt, and the organic salt is a sodium salt or a potassium salt of the water-soluble organic acid.

[0044] Specifically, adding an organic salt can make the taste of the sucralose complex better.

[0045] Optionally, the mass percentage of the organic salt is 1% to 10%.

[0046] The second aspect of the present application provides a preparation method of a sucralose complex, please refer to Figure 1 , comprising:

[0047] S1: Dissolve sucralose solid in a solvent preheated to 40-60℃.

[0048] S2: Under stirring, add organic acid, organic salt and polyphenol hydroxyl substance to make them completely dissolved.

[0049] S3: Cool to 20-10℃ at a cooling rate of 0.5-5℃ / min.

[0050] S4: Compound culture, -4℃~4℃, culture for 3~4 hours. Through compound culture, the crystal of sucralose compound is precipitated.

[0051] S5: Filtration.

[0052] S6: Drying to obtain the sucralose compound.

[0053] Optionally, the solvent includes one or more of deionized water, ethanol, acetone, propylene glycol, triethyl citrate, triacetin.

[0054] Preferably, the solvent includes deionized water and ethanol, and the mass ratio of the deionized water to the ethanol is not less than 2. Among them, ethanol helps to dissolve polyphenol hydroxyl substances and speeds up the compound preparation process.

[0055] Preferably, the mass of the solvent is 3.5-50 times the mass of the sucralose.

[0056] Optionally, the stirring rate is 300~700rpm.

[0057] Preferably, the drying temperature is 20~30℃, and the drying is performed under normal pressure or vacuum for 3~4 hours.

[0058] The third aspect of the present application provides an atomized type essence including the sucralose compound of any one of the first aspect.

[0059] The embodiments of the present application will be described in detail below with specific examples, but those skilled in the art will understand that the following examples are only used to illustrate the present application, and should not be regarded as limiting the scope of the present application. The specific conditions are not specified in the examples, and the conventional conditions or the conditions recommended by the manufacturer are used. The reagents or instruments used are not specified by the manufacturer, and are conventional products that can be purchased on the market.

[0060] Example 1

[0061] S1: Dissolve 5.0g of sucralose solid in 25.0g of deionized water preheated to 45℃.

[0062] S2: Under the condition of stirring at 350rpm, add 0.240g of citric acid, 0.320g of sodium citrate, and 0.050g of chlorogenic acid, and make them completely dissolved.

[0063] S3: Cool to 18℃ at a cooling rate of 1.5℃ / min.

[0064] S4: Compound culture, 4℃, culture for 3 hours, and the crystal of sucralose compound is precipitated.

[0065] S5: Filtration.

[0066] S6: Drying, taking the sucralose complex crystals on the filter paper after suction filtration, placing in a 30°C oven, vacuum drying for 3 hours, obtaining the sucralose complex of Example 1.

[0067] Example 2

[0068] S1 : Dissolving 5.0 g of sucralose solid in 25.0 g of deionized water preheated to 45°C.

[0069] S2: Adding 0.240 g of citric acid, 0.320 g of sodium tartrate, 0.050 g of chlorogenic acid under the condition of stirring at 350 rpm, and making it completely dissolved.

[0070] S3: Cooling to 18°C at a cooling rate of 1.5°C / min.

[0071] S4: Complex culture, 4°C, culturing for 3 hours, and precipitating sucralose complex crystals.

[0072] S5: Suction filtration.

[0073] S6: Drying, taking the sucralose complex crystals on the filter paper after suction filtration, placing in a 30°C oven, vacuum drying for 3 hours, obtaining the sucralose complex of Example 2.

[0074] Example 3

[0075] S1 : Dissolving 5.0 g of sucralose solid in 25.0 g of deionized water preheated to 45°C.

[0076] S2: Adding 0.240 g of succinic acid, 0.320 g of sodium citrate, 0.050 g of chlorogenic acid, 0.05 g of anhydrous ethanol under the condition of stirring at 350 rpm, and making it completely dissolved.

[0077] S3: Cooling to 18°C at a cooling rate of 1.5°C / min.

[0078] S4: Complex culture, 4°C, culturing for 3 hours, and precipitating sucralose complex crystals.

[0079] S5: Suction filtration.

[0080] S6: Drying, taking the sucralose complex crystals on the filter paper after suction filtration, placing in a 30°C oven, vacuum drying for 3 hours, obtaining the sucralose complex of Example 3.

[0081] Example 4

[0082] S1 : Dissolving 5.0 g of sucralose solid in 25.0 g of deionized water preheated to 45°C.

[0083] S2: 0.240 g of benzoic acid, 0.320 g of sodium citrate, 0.050 g of chlorogenic acid, and 0.1 g of anhydrous ethanol were added under stirring at 350 rpm, and the mixture was allowed to completely dissolve.

[0084] S3: The temperature was lowered to 18°C at a rate of 1.5°C / min.

[0085] S4: The complex was cultured at 4°C for 3 hours, and sucralose complex crystals were precipitated.

[0086] S5: Filtration.

[0087] S6: Drying. The sucralose complex crystals on the filter paper after filtration were placed in an oven at 30°C, and vacuum drying was performed for 3 hours to obtain the sucralose complex of Example 4.

[0088] Referring to the preparation method of the above examples, the sucralose complexes of Examples 5 to 10 were also prepared according to the formulation compositions of the sucralose complexes of each example shown in Table 1. The formulation of the sucralose complex of each example is shown in Table 1. Among them, the organic acid of Example 1 and Example 2 is a ternary acid, Example 3 is a binary acid, Example 4 is a monobasic acid, Example 7 uses two polyphenols, Example 8 and Example 9 increase the amount of polyphenol hydroxyl substances, and Example 10 increases the amount of organic acid.

[0089] Table 1 Formulation composition of sucralose complex of each example

[0090]

[0091]

[0092] Test Example

[0093] 1 g of each of the sucralose complexes of Examples 1 to 10 prepared above was added to 2.0 g of propylene glycol, 5.0 g of glycerol, and 2.0 g of deionized water, and stirring was performed at 350 rpm for 10 min to prepare Test Group 1 to Test Group 10, respectively. Then, each of the mixtures of Test Group 1 to Test Group 10 was injected into a cartridge, and aerosol was collected using a Cambridge filter under the following conditions: a puff volume of 55 mL, a puff time of 3 s, a puff interval of 30 s, and a puff number of 100 puffs. The release amount of 3-chloro-1,2-propanol was measured under the test conditions simulating the use environment of an aerosol-type flavor.

[0094] Meanwhile, each test group is respectively provided with a control group, the control group is to use sucralose as a sweetener to simulate the use environment of the atomized flavor to test, to detect the release amount of 3-chloro-1,2-propanol, the simulation conditions are consistent with the sucralose compound, which will not be repeated here. The sucralose content of control group 1 to control group 10 is respectively the actual sucralose content contained in 1g sucralose compound of the corresponding test group. Specifically, control group 1 to control group 7 is 0.891g of dry sucralose, 2.109g of propylene glycol, 5.0g of glycerol, 2.0g of deionized water are added, and 350rpm stirring is carried out for 10min. In addition, control group 8 is 0.876g of dry sucralose, control group 9 is 0.859g of dry sucralose, and control group 10 is 0.810g of dry sucralose. The preparation method is similar to that of control group 1 to control group 7, which will not be repeated here.

[0095] The content of 3-chloro-1,2-propanol in the aerosol of the test group and the control group is detected and analyzed by GC / MS method, and the release amount of 3-chloro-1,2-propanol obtained by testing of test group 1 to test group 10 and control group 1 to control group 10 is shown in Table 2.

[0096] Table 2: Release amount of 3-chloro-1,2-propanol obtained by testing of each test group and control group

[0097]

[0098]

[0099] As can be seen from Table 2, the release amount of 3-chloro-1,2-propanol of each test group is significantly reduced relative to each control group, which proves that the sucralose compound of the embodiment scheme of the present application can reduce the release amount of 3-chloro-1,2-propanol when used in the atomized flavor, thereby improving the safety of the atomized flavor. The main reason for the analysis is that organic acids can stabilize the glycosidic bond of sucralose molecules to reduce their cleavage, and organic acids can promote the generation of hydrogen chloride to proceed in the opposite direction, thereby reducing the generation of hydrogen chloride and preventing its reaction with glycerol to generate chloropropanol substances. And the test group 7 of example 7 which adopts two kinds of polyphenol hydroxyl substances in combination has a more significant effect on reducing the release amount of 3-chloro-1,2-propanol. The main reason for the analysis is that polyphenol hydroxyl substances can form an adduct with 4-chloro-galactosyl cation, the intermediate of sucralose cleavage, to inhibit its further degradation to produce HCl, thereby achieving the purpose of inhibiting the release of HCl. And the sucralose compound with increased polyphenol hydroxyl substance content in example 8 and example 9 corresponding to test group 8 and test group 9 also has a significant effect on reducing the release amount of 3-chloro-1,2-propanol. The sucralose compound with increased organic acid content in example 10 corresponding to test group 10 also enhances the effect on reducing the release amount of 3-chloro-1,2-propanol.

[0100] The above merely describes optional embodiments of the present application, and does not limit the patent scope of the present application, and any equivalent structural transformation made under the inventive concept of the present application, or direct / indirect application in other related technical fields, is included in the patent protection scope of the present application.

Claims

1. A complex of trichlorogalactose sucrose, characterized in that, The trichlorosucrose complex comprises trichlorosucrose and additives, the additives comprise organic acid, polyphenol hydroxyl substance and organic salt, wherein the mass percentage of the trichlorosucrose is 70% to 95%, the mass percentage of the organic acid is 1% to 15%, the mass percentage of the polyphenol hydroxyl substance is 0.1% to 5%, the organic salt is sodium salt or potassium salt of water-soluble organic acid, and the mass percentage of the organic salt is 1% to 10%.

2. A complex of trichlorogalactosucrose according to claim 1, characterized in that, The organic acid comprises one or more of benzoic acid, salicylic acid, coffee acid, dodecanoic acid, hexadecanoic acid, octadecanoic acid, decanoic acid, phenylacetic acid and cinnamic acid.

3. A complex of trichlorogalactosucrose according to claim 1, characterized in that, The organic acid comprises one or more of tartaric acid, malic acid, fumaric acid, succinic acid, ethanedioic acid, propanedioic acid, pentanedioic acid, hexanedioic acid, phthalic acid, maleic acid and hexadienoic acid.

4. A complex of trichlorogalactosucrose according to claim 1, characterized in that, The organic acid comprises one or more of citric acid, isocitric acid, propane-1,2,3-tricarboxylic acid, homocitric acid, homoisocitric acid and trimesic acid.

5. A complex of trichlorogalactosucrose according to any one of claims 2 to 4, characterized in that, The polyphenol hydroxyl substance comprises one or more of catechin, isoflavone, cocoa polyphenol, curcumin, quercetin, rutin, resveratrol, shikonin, pelargonidin, methylic cyanidin, delphinidin, malvidin, kaempferol, myricetin, apigenin and naringenin.

6. A complex of trichlorogalactosucrose according to any one of claims 2 to 4, characterized in that, The polyphenol hydroxyl substance comprises one or more of chlorogenic acid, hydroxybenzoic acid, protocatechuic acid, gallic acid, p-hydroxybenzoic acid, coumaric acid and ferulic acid.

7. A process for the preparation of a complex of sucralose according to any one of claims 1 to 6, characterized in that, The method comprises: S1: dissolving trichlorosucrose solid in a solvent preheated to 40 to 60°C; S2: under stirring, adding organic acid, organic salt and polyphenol hydroxyl substance to make them completely dissolved; S3: cooling to 20 to 10°C at a cooling rate of 0.5 to 5°C / min; S4: complex culture, -4°C to 4°C, for 3 to 4 hours; S5: suction filtration; S6: drying to obtain the trichlorosucrose complex.

8. An atomized flavoring essence characterized by, The trichlorosucrose complex comprises the trichlorosucrose complex of any one of claims 1 to 6.

Images