Dicarboxylic acid sucrose and furanuronic acid fructose m-glycan esters and processes for their preparation, and their use as hypoglycemic slow-sugar supplements

Abstract

The present invention relates to a novel granular or powdered natural white slow sugar and a method for the production thereof based on an esterification reaction. The resulting product (i.e., novel natural white slow sugar) has a lower glycemic index (15-36.5), and thus can be eaten by anyone regardless of their health conditions. The novel natural white slow sugars are obtained by slow, limited, non-thermal esterification reactions. The novel natural white slow sugar obtained according to the present invention can be used to prepare all food products, such as cakes, pastries, candies, fruit juice ice cream and ice cream, fruit juices, various types of beverages, chocolate-like products, caramel products, and the like, typically prepared using conventional commercial white sugar. The novel natural white slow sugar can be used for preventing diseases such as tooth decay, obesity and retinopathy.

Description

[0001] The present invention relates to a novel natural granular or powdered white slow sugar and a manufacturing process thereof. The slow sugar is obtained through an industrial manufacturing process based on an esterification reaction, as shown in the following figure, including a new molecule for obtaining a novel slow sugar from commercial natural white sugar (sucrose).

[0002]

[0003] Esterification is a chemical reaction between carboxylic acid and alcohol to produce ester and water. Figure 1 ),( Figure 2 )、( Figure 3 )and( Figure 5 ).

[0004] Numerous experimental studies have shown that equimolar mixtures of carboxylic acids and alcohols result in slow and incomplete conversions.

[0005] The esterification reaction of the present invention is slow, limited, and non-thermal.

[0006] The esterification / hydrolysis equilibrium is characterized as a dynamic equilibrium. In this equilibrium, the forward reaction and the reverse reaction occur simultaneously, and the reactants and products coexist in a constant ratio. The two reverse reactions actually develop towards the same equilibrium state.

[0007] The present invention is based on a new type of natural white slow sugar obtained by a slow, limited, non-thermal esterification reaction.

[0008] —Slow, esterification reaction is characterized by the release of a new slow sugar at the intestinal level, which is consistent with the slow secretion of insulin in type 2 diabetes.

[0009] —Limited means that the esterification reaction is limited by the esterification / hydrolysis formed, which in turn is limited by the two reverse reactions.

[0010] —Non-thermal means that the equilibrium is not affected by temperature.

[0011] The novel natural granular or powdered white slow sugar is prepared from commercial natural white sugar by adding an acidic oxidant and undergoing a manufacturing process ( Figure 6 ), obtained by industrial-scale esterification. Thus, a new type of natural white slow sugar consumed by hydrolysis can be obtained.

[0012] The esterification reaction on one side and the hydrolysis on the other side achieve a chemical balance in the human body, which may be controlled by the chemical balance generated by the esterification / hydrolysis ratio ( Figure 4 ) to control consumption through limited absorption of sugar.

[0013] Therefore, if the sugar we consume exceeds the amount of sugar needed by the human body, the excess sugar will not be stored in the body but will be excreted from the body due to the permanent control effect of esterification and hydrolysis.

[0014] The invention relates to a novel natural white slow sugar, the manufacturing principle of which is based on the chemical balance between alcohol esterification reaction and its hydrolysis.

[0015] The chemical equilibrium of esterification / hydrolysis is used for esterification reactions ( Figure 1 )、( Figure 2 )、( Figure 3 )and( Figure 4 ):

[0016] Alcohol (sugar) + carboxylic acid → ester (new slow sugar) + water

[0017]

[0018] The reaction is a dynamic equilibrium between two reactions (esterification / hydrolysis) that occur simultaneously in opposite directions.

[0019] In the industrial-scale production of new natural white slow sugar, the esterification reaction direction is favored.

[0020] At the time of consumption and at the intestinal level, the opposite is true, as hydrolysis reactions favor the slow release (LP) of sugars from new sugars (i.e., sugar esters) according to the slow and limited insulin secretion. Figure 4 ).

[0021] The novel natural white slow sugar disclosed by the present invention can slowly secrete insulin according to type 2 diabetes at the intestinal level, continuously release LP, and is also similar to ( Figure 4 ).

[0022] The chemical basis of the novel natural white slow sugar involved in the present invention is obtained through the chemical mechanism of synthesizing the novel slow sugar:

[0023] Oxidation reaction ( Figure 5-1 ):

[0024] Sugars first undergo monosaccharide reactions including sugar acid oxidation, which makes the primary hydroxyl group more susceptible to attack and often complete oxidation to form the carboxylic acid state.

[0025] The product is a polyhydroxycarboxylic acid called sugar acid.

[0026] For example, nitric acid is a very good oxidizing agent for making sugar acids.

[0027] Oxidation reaction of a new type of natural red slow sugar

[0028]

[0029] Esterification reaction ( Figure 5-3 ):

[0030] The hydroxyl groups in sugars can be esterified by the common method of carboxylic acid + alcohol.

[0031] Carboxylic acids react via acid-catalyzed nucleophilic addition to the carbon in the carboxyl group.

[0032] The best known reaction is the esterification reaction, which is an equilibrium reaction.

[0033] Starting from an equimolar mixture of carboxylic acid and alcohol, 65% of ester and water and 35% of acid and alcohol are obtained. The yield can be increased by increasing the concentration of the reactants or decreasing the concentration of the products (Le Chatelier's principle).

[0034] Acid-catalyzed esterification is an important method for preparing esters (new slow sugars).

[0035]

[0036] The novel natural white slow sugar disclosed by the present invention is a slow sugar obtained and consumed according to the physicochemical characteristics of the "esterification / hydrolysis" chemical balance. These physicochemical characteristics include:

[0037] —Slow, because it takes longer to release LP

[0038] —Limited, because it is limited by the reverse reaction

[0039] —Non-thermal, because the equilibrium is not affected by temperature.

[0040] The novel natural white slow sugar involved in the present invention exists in the form of ester chemically.

[0041] Comparison with naturally occurring ester-containing substances such as stevia, tannins and apple plants led to the conclusion that the chemicals in ester form are harmless.

[0042] Extension of esterification reaction ( Fig.10 ):

[0043] Glycolipids can be obtained by esterification of two types of sugars:

[0044] —Sugar alcohol (functional —OH): commercial white sugar.

[0045] —Acidic sugar (function —COOH): sugar acid.

[0046] After sucrose is hydrolyzed into glucose and fructose, the two sugars obtained will undergo esterification reaction in sequence.

[0047]

[0048] After glucose is oxidized to gluconic acid, glucose and gluconic acid undergo an esterification reaction to form an ester consisting of two glucose molecules:

[0049]

[0050] Fructose can be used in the same way to obtain glycolipids ( Fig.11 ).

[0051]

[0052] Slow sugar refers to sugar with a glycemic index of less than 59.

[0053] It has long been mistakenly believed that slow sugars are complex carbohydrates.

[0054] The novel natural white slow sugar obtained according to the present invention can be used to prepare all foods that are usually prepared using commercial natural white sugar, for example, cakes, pastries, candies, sorbets and ice creams, fruit juices, various types of beverages, chocolate products, cocoa products, caramel products, etc.

[0055] This new natural white slow-acting sugar is absorbed slowly by the body. It is essential for ensuring that athletes continue to get the energy they need and prevent cramps in intense endurance sports (regardless of the nature of the sport).

[0056] In fact, the novel natural white slow sugar involved in the present invention is also absorbed very slowly by the human body, and therefore, can also be used during work.

[0057] The novel natural white slow sugar involved in the present invention does not cause reactive hypoglycemia, while on the other hand, commercial natural white sugar is released quickly, causing a rapid increase in blood sugar levels, which is very dangerous, i.e., easily induces hyperglycemia.

[0058] Slow sugars are sugars with a very low glycemic index, which means that they release energy into your body over a period of time and are therefore beneficial to your health.

[0059] The glycemic index is a scale that ranks foods based on their effect on blood sugar (glucose levels in the blood) within two hours of consuming a carbohydrate-containing food. The index allows you to compare the glycemic capacity of each food as measured directly during digestion.

[0060] A food with a low glycemic index means that after digestion of that food, blood sugar levels in the body rise only slightly, as shown in the chart below.

[0061] Low, GI ≤ 35: for example, dried vegetables, dairy products, meat, etc.

[0062] Among them, 35 < GI < 50: for example, bananas, apricots, etc.

[0063] High, GI > 50: for example, dates, candies, etc.

[0064] Therefore, whether the ingested food will increase blood glucose intensity is represented by a value called GI.

[0065] Therefore, the novel natural white slow sugar involved in the present invention is a slow sugar with a very low glycemic index, and the glycemic index value of this sugar is obtained by measuring according to the clinical trial protocol of hyperglycemia induced by HGPVO in a medical analysis laboratory.

[0066] The novel slow sugar is prepared by a chemical esterification reaction. Therefore, the esterification / hydrolysis reaction after ingesting this slow sugar is relatively slow and requires strong catalysis by an acid.

[0067] In the present invention, the mechanisms of primary alcohol esters and secondary alcohol esters are opposite to the mechanism of acid-catalyzed esterification reaction.

[0068] Therefore, the esterification / hydrolysis reaction is in an equilibrium state.

[0069] The novel natural white slow sugar is produced according to the following process.

[0070] For example, to obtain 10 kg of novel natural granular or powdery white slow sugar, deionized water and an acidic oxidant used as a catalyst must be mixed in a container box, and then it is heated to 90 to 100 °C while stirring.

[0071] While continuing to heat, 10 kg of traditional commercial white sugar is gradually added to the container box (the duration is 10 minutes), and it is stirred at a speed of 25 - 35 revolutions per minute with a fixed, electrically operated propeller or blade stirrer while adding until light brown molasses is obtained. This operation called cooking needs to last for 30 to 45 minutes.

[0072] After obtaining this molasses, heating is stopped, fresh cold air is first blown into the container box, and then hot air is blown in, and it is stirred at a speed of 30 to 50 revolutions per minute while blowing to dry the molasses. The entire blowing process lasts for 30 to 35 minutes.

[0073] At the end of the drying operation, this molasses will become a novel natural granular white slow sugar. After screening, a novel sugar with uniform particle size can be obtained. Screening reduces the weight from the initial 10 kg by 300 to 400 g, which can be confirmed by the final weighing of the novel natural white slow sugar obtained by the present invention.

[0074] If you need to produce powdered new natural white slow sugar, you must grind and sifte the new natural granulated white slow sugar to complete the described manufacturing process.

[0075] Whatever the weight of the new natural white slow sugar to be prepared, in large quantities, the same procedure as above must be followed at all stages in terms of time, temperature and speed, provided that one or more containers are equipped to measure the required output and a sufficient number of stirrers to allow the mixture in the containers to be fully stirred. Large quantities can also be produced by using multiple containers with a capacity of 10 or 20 kg or more, with synchronous production triggered by a controller.

[0076] The glycemic index of the new natural white slow sugar involved in the present invention is between GI 15 and 36.5. Figure 7 and Figure 8 The total area horizontal to the middle curve is represented.

[0077] The novel natural granular or powdered white slow sugar involved in the present invention has certain nutrition, zero calories, and has the functions of weight loss, prevention of tooth decay and the like.

[0078] The novel natural white slow-release sugar involved in the present invention has undergone an esterification reaction and is characterized in that it can release LP for a long time under the action of hydrolysis, that is, the reverse chemical reaction of the esterification reaction. Therefore, it also has an anti-diabetic effect and can be used to prevent retinopathy and nephropathy.

[0079] Therefore, not only healthy subjects are suitable for using this new slow sugar, but also patients with type 2 diabetes.

[0080] Therefore, an HbA1C level of 7% in the blood is equivalent to an average blood sugar level of 1.5 g per liter of blood, while an increase or decrease of 1% in the HbA1C level means that the blood sugar level has increased or decreased by an average of 0.30 g / liter.

[0081] The following results were obtained for the novel natural granulated or powdered white slow sugar involved in the present invention:

[0082] Reduced HbA1c levels by 7.2%

[0084] For conventional commercial white sugar, for comparison purposes, we obtained the following results:

[0085]

[0086] Slow sugars have long been considered alternative sugars rather than sugar substitutes or fake sugars, and are usually presented in liquid form. The only difference is that their preparation process is inconsistent with the manufacturing process of the present invention, which is based on the chemical balance of "esterification / hydrolysis".

[0087] By analyzing the new natural granulated or powdered white slow sugar according to the present invention as follows within 12 months, the physical and chemical properties of the slow sugar were obtained, and the relevant values ​​are shown in the following table, which also confirms the chemical stability of the new sugar. The new sugar is a concentrated culture medium that will not deteriorate even if stored for a long time.

[0088]

[0089] This new natural white slow sugar in granulated or powdered form is nothing but an equimolar mixture of glucose and fructose obtained by enzymatic or chemical hydrolysis of sucrose.

[0090] Oxidative hydrolysis of sucrose usually occurs partially, producing a completely new type of sucrose.

[0091] The refractive index of the novel natural granular or powdered white slow sugar of the present invention is 1.3412, and the polarization index is determined according to the Z° unit of 64.9.

[0092] The glycemic index was measured according to a clinical trial protocol of the oral glucose tolerance test (OGTT) and was analyzed and compared in two subjects by repeated administration of the new natural white slow sugar. These analyses allowed the comparison of this slow sugar with a low glycemic index with a control of conventional commercial white sugar with a very high glycemic index ( Fig. 9 ).

[0093] The esterified sugar molecules of the new natural white slow sugar (i.e., bimolecular, homosexual or heterosexual esterified sucrose, esterified glucose and esterified fructose) can actually be inevitably chemically synthesized, i.e.: glucose-glucose, fructose-fructose, glucose-fructose and sugar-sugar.

[0094]

[0095] This is demonstrated and confirmed by the results of the esterification index IE calculated from the saponification index IS and the acidity index IA (IE=IS-IA) according to the French Pharmacopoeia (10th edition).

[0096]

[0097] All esterified sugar molecules specified in the present invention are named SATTAR and are obtained by the following method:

[0098] Oxidation reactions: All primary hydroxyl groups of sucrose, glucose, and fructose are more susceptible to attack and are usually completely oxidized to the carboxylic acid state.

[0099] Esterification: To ensure the subsequent esterification, these molecules react with sugar alcohol molecules in the form of homomolecules and / or corresponding heteromolecules ( Figure 5-2 a and Figure 5-2 b).

Claims

1. A novel natural granulated or powdered white slow sugar obtained by a manufacturing process based on esterification reaction, wherein the process starts with the use of commercial natural white sugar, oxidation reaction of the white sugar by an acidic oxidizing agent, and then esterification reaction of the white sugar using the same acidic oxidizing agent as a catalyst to obtain esters conforming to the following novel molecules, 2. The novel natural granulated or powdered white slow sugar according to claim 1, wherein the sweetness of commercial natural white sugar is retained, and the characteristic is that the glycemic index is low, between GI 15 and 36.

5.

3. The novel natural granulated or powdered white slow sugar according to claims 1 and 2, wherein the refractive index is 1.3412 and the polarization Z° unit is 64.

9.

4. The novel natural white slow sugar according to claims 1 and 2, wherein subjects with type 2 diabetes are also suitable for use.

5. The novel natural white slow sugar according to claims 1 and 2, wherein the chemical balance of esterification / hydrolysis is associated with a slow secretion of insulin in the body, so that excess sugar is not stored but only eliminated, thus having a weight loss effect.

6. The novel natural white slow sugar according to claims 1 and 2, wherein the slow sugar has certain nutrition, zero calories, can prevent tooth decay by blocking the alcohol function (-OH), and after consumption by diabetic subjects, can slow down or / and prevent retinopathy and nephropathy and other pathological complications.

7. The novel natural white slow sugar according to claims 1 and 2, wherein the slow sugar is in the form of liquid solution, syrup, paste, cream, honey or caramel.

8. The novel natural granulated or powdered white slow sugar according to claims 1 and 2, wherein 10 kg of such slow sugar is produced by the following process: Mix two liters of desalinated water with an acidic oxidant; Place the bowl with the mixture on the stove and heat, stirring, for 10 minutes until it reaches 90 to 100 degrees Celsius. Add 10 kg of commercial natural white sugar to the mixture; Cook while stirring at 25 to 35 rpm; The obtained molasses is dried for 30 to 45 minutes by introducing fresh air and then hot air while stirring at a speed of 30 to 50 rpm.

9. A new type of natural white slow sugar, which is recommended for athletes who need to do intense exercise, because its slow esterification reaction can ensure long-term release, in addition, it also has endurance and can protect muscles from cramps.

10. The novel natural granular or powdered white slow sugar according to claims 1, 2 and 8, wherein the slow sugar can be used as a raw material for making liquid, paste, cream, honey or caramel products, or for preparing or producing medicines and auxiliary medicines, as well as body care products, health products and cosmetics.

11. The novel natural white slow sugar according to claims 1 and 2, wherein the chemical equilibrium of the esterification / hydrolysis reaction has three characteristics: slow, limited and non-thermal.

12. The novel natural white slow sugar according to claims 1 and 2, wherein the slow sugar is obtained by the reaction between sugar alcohol (sucrose) and acidic sugar (sugar acid), and the latter is obtained by oxidation reaction of sugar alcohol.

13. The novel natural white slow sugar according to claims 1 and 2, wherein the slow sugar is prepared by using the same acid oxidation catalyst used in sugar oxidation and esterification.

14. A new type of natural white slow sugar, which, after entering the human intestine, will prolong the release of LP according to the secretion of insulin, and then it will become slower.

15. A new type of natural white slow sugar, in which glucose exists chemically in the form of lipids, and its molecule is as follows:

16. A new type of natural white slow sugar, in which fructose exists chemically in the form of fat, and its molecule is as follows:

17. The esterification of the two sugars may be homologous (only the molecules according to claim 15 or 16), i.e. each molecule is esterified separately, or heterologous (the molecules according to claim 15 and 16), i.e. the glucose molecule and the fructose molecule are esterified together.

18. After glucose is oxidized to gluconic acid, glucose and gluconic acid undergo an esterification reaction to form an ester consisting of two glucose molecules: Fructose can be used in the same way to obtain glycolipids (Figure 11).

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