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 red slow sugar and to a method for the production thereof based on an esterification reaction. The obtained product (namely, the novel natural brown sugar) has the effect of reducing blood sugar, and the blood sugar value is lower than 1g, so that any person can eat the product regardless of the health condition. The novel natural brown sugar is obtained through a slow, limited, non-thermal esterification reaction and comprises a series of dried plant products beneficial to human health. The novel natural brown sugar obtained according to the present invention can be used to prepare all food products typically prepared using commercial natural white sugar, such as cakes, pastries, confections, fruit juice ice cream and ice cream, fruit juices, various types of beverages, chocolate-like products, caramel cocoa products, and the like. The novel natural brown sugar can be used for preventing diseases such as decayed teeth, obesity and retinopathy.

Description

[0001] The present invention relates to a natural red granular or powdered blood sugar-lowering slow sugar and a manufacturing process thereof. The slow sugar uses commercial natural brown sugar and is obtained through an industrial manufacturing process based on an esterification reaction, including a group of dried plant products (as shown in the figure below), which include new molecules of a new natural red slow sugar.

[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 red slow sugar obtained through 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 red slow sugar to which the present invention relates is obtained from commercial natural white sugar by mainly adding an acidic oxidant and dried plants and seeds (i.e., flax, black seed, ginger, curcumin, cinnamon, cloves, fenugreek, tea, coffee, cocoa and pepper, desalted water, etc.), through a manufacturing process, using an industrial-scale esterification reaction. In this way, a novel natural red slow sugar that is consumed by hydrolysis can be obtained (Figure).

[0012] Esterification on one side and hydrolysis on the other side achieve a chemical balance in the human body, making it possible to control consumption through limited absorption of sugars controlled by the chemical balance created by the esterification / hydrolysis ratio.

[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 red 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 red slow sugar, the esterification reaction direction is favored.

[0020] On the other hand, at the intestinal level, the opposite is true, as the hydrolysis reaction favors the slow release (LP) of sugars from the new natural red slow sugars (i.e., sugar esters) according to the continuous, slow, and limited insulin secretion. Figure 4 ).

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

[0022] The chemical basis of the novel natural red 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 a sugar acid. For example, nitric acid is a very good oxidizing agent for preparing sugar acids.

[0026] Oxidation reaction of a new type of natural red slow sugar

[0027]

[0028] Esterification reaction ( Figure 5-3 ):

[0029] The hydroxyl groups in sugars can be esterified by the common method of carboxylic acid + alcohol.

[0030] Carboxylic acids react via acid-catalyzed nucleophilic addition to the carbon in the carboxyl group.

[0031] The best known reaction is the esterification reaction, which is an equilibrium reaction.

[0032] 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).

[0033] Acid-catalyzed esterification is an important method for preparing esters (new slow sugars).

[0034]

[0035] The novel natural red 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:

[0036] —Slow, because it takes longer to release LP;

[0037] —Limited, because it is limited by the reverse reaction;

[0038] —Non-thermal, because the equilibrium is not affected by temperature.

[0039] The novel natural red slow sugar involved in the present invention exists in the form of ester chemically.

[0040] 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.

[0041] Extension of esterification reaction ( Fig.10 ):

[0042] Glycolipids can be obtained by esterification of two types of sugars:

[0043] —Sugar alcohol (functional —OH): commercial natural white sugar.

[0044] —Acidic sugar (function —COOH): sugar acid.

[0045] After sucrose is hydrolyzed into glucose and fructose, the two sugars obtained will undergo esterification reaction in sequence.

[0046]

[0047] After glucose is oxidized to gluconic acid, glucose and gluconic acid undergo an esterification reaction to form an ester consisting of two glucose molecules:

[0048]

[0049] Fructose can be used in the same way to obtain glycolipids ( Fig.11 ).

[0050]

[0051] It has long been mistakenly believed that slow sugars are complex carbohydrates.

[0052] The novel natural red slow sugar obtained according to the present invention can be used to prepare all foods that are usually prepared using commercial natural white sugar, such as cakes, pastries, candies, sorbets and ice creams, fruit juices, various types of beverages, chocolate products, cocoa products, caramel products, etc.

[0053] This new natural red slow sugar is absorbed slowly. It is essential for all kinds of sports that require endurance and intense sports (regardless of the nature of the sport) to ensure that athletes continue to get the energy they need and prevent cramps.

[0054] In fact, the novel natural red slow sugar according to the present invention is also absorbed very slowly, and therefore, can also be used during work.

[0055] The novel natural red 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.

[0056] The slow sugar involved in the present invention has the effect of lowering blood sugar, and therefore is beneficial to your health.

[0057] After consuming slow sugar, the release rate of insulin will slow down and there will be no blood sugar peak.

[0058] The result is that your muscles stay fueled for hours, providing you with a constant supply of energy during exercise.

[0059] This new type of natural red slow sugar is prepared through a chemical esterification reaction. Therefore, the esterification / hydrolysis reaction after ingesting this slow sugar is relatively slow and requires strong catalysis by acid.

[0060] In the present invention, the mechanism of primary alcohol ester and secondary alcohol ester is opposite to that of acid-catalyzed esterification.

[0061] Therefore, the esterification / hydrolysis reaction is in equilibrium.

[0062] The new natural red slow sugar is produced according to the following process.

[0063] For example, to obtain 10 kg of the new natural granulated red slow sugar, desalted water must be mixed with an acid catalyst oxidant, and a mixture of dried plants and seeds (i.e., flax, nigella, ginger, curcumin, cinnamon, cloves, fenugreek, tea, coffee, cocoa and pepper, desalted water, etc.) in a container box, and then heated to 90 to 100°C while stirring.

[0064] While continuing to heat, gradually add 10 kg of conventional commercial natural white sugar to the container (duration 10 minutes), stirring at 25-35 rpm with a fixed, electrically operated propeller or blade stirrer until dark brown molasses is obtained. This operation, called cooking, takes 30 to 45 minutes.

[0065] After obtaining the molasses, the heating is stopped, and fresh cold air is blown into the container box first, and then hot air is blown in, while using a propeller or blade stirrer at a speed of 30 to 50 revolutions per minute to dry the molasses. The entire blowing process lasts 30 to 35 minutes.

[0066] At the end of the drying operation, the molasses becomes a new type of natural granular red slow sugar, which can be obtained after sieving to obtain a new type of sugar with uniform particle size. Sieving reduces the weight by 300 to 400 g from the initial 10 kg, which can be confirmed by the final weighing of the new type of natural red slow sugar obtained by the present invention.

[0067] By removing or adding some plants and seeds, you can change the properties of plants and seeds.

[0068] If you need to produce powdered new natural red slow sugar, you must grind and sifte the new natural granulated red slow sugar to complete the described manufacturing process.

[0069] Whatever the weight of the new natural red slow sugar to be prepared, in large quantities, all stages must follow the same procedure as above 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 fully stir the mixture in the container. 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.

[0070] The novel natural red slow sugar disclosed by the present invention has the property of lowering blood sugar. This property is reflected by the fact that Figure 7 ) and 120 days ( Figure 8)The curve of diabetes monitoring and analysis results is presented.

[0071] The novel natural granular or powdered red slow sugar involved in the invention has certain nutrition, zero calories, and has the functions of losing weight, preventing tooth decay and the like.

[0072] The novel natural red slow sugar involved in the present invention has undergone 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 anti-diabetic effect and can be used to prevent retinopathy and nephropathy.

[0073] Therefore, not only healthy subjects are suitable for using this new slow sugar, but also diabetic patients.

[0074] 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.

[0075] The following results were obtained for the novel natural granulated or powdered red slow sugar involved in the present invention:

[0076]

[0077] This clearly showed that this new natural red slow sugar reduced HbA1c levels by 7.2%.

[0078] For commercial natural white sugar, for comparison purposes, we get the following results:

[0079]

[0080] This means that commercial natural white sugar increased HbA1c levels by 9.2%.

[0081] 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 not similar or the same as the manufacturing process of the present invention, which is based on the chemical balance of "esterification / hydrolysis".

[0082] By conducting the following analysis on the novel natural granular or powdered red slow sugar of the present invention within 12 months, the physical and chemical properties of the slow sugar were obtained, and the relevant values ​​are shown in the following table ( Fig. 9 ), which also confirmed the chemical stability of this new sugar. This slow sugar is a concentrated culture medium that will not deteriorate even after long-term storage.

[0083]

[0084] This new natural granulated or powdered red slow sugar is nothing but an equimolar mixture of glucose and fructose obtained by enzymatic or chemical hydrolysis of sucrose.

[0085] Sucrose is hydrolyzed, usually partially, by an acidic oxidant to produce a completely new form of sucrose.

[0086] The refractive index of the novel natural granular or powdered red slow sugar involved in the present invention is 1.3408, and the polarization index is determined according to the Z° unit of 60.0.

[0087] Blood glucose was measured according to the clinical trial protocol of the oral glucose tolerance test (OGTT), and the two subjects were analyzed and compared by repeated use of the new natural red slow sugar. Through these analyses, the slow sugar with blood glucose lowering function was compared with the traditional commercial natural white sugar as a control with very high blood glucose ( Figure 7 ).

[0088] 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.:

[0089] Glucose-glucose, fructose-fructose, glucose-fructose and sugar-sugar.

[0090]

[0091] 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).

[0092]

[0093] All esterified sugar molecules specified in the present invention are named SATTAR and are obtained by the following method:

[0094] 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.

[0095] 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 red granular or powdered slow-acting sugar for lowering blood sugar and its manufacturing process, wherein the slow-acting sugar uses commercial natural white sugar and is obtained through an industrial manufacturing process based on esterification reaction, including a group of dried plant products, wherein the plant products include a new molecule of the novel natural red slow-acting sugar, 2. The new natural red slow sugar according to claim 1 retains the sweetness of commercial natural white sugar with blood sugar lowering function, and is characterized by low blood sugar obtained through oxidation reaction and esterification reaction, less than 1 gram (Figures 5, 7 and 8).

3. The novel natural granular or powdered red slow sugar according to claim 1, wherein the refractive index is 1.3408 and the polarization Z° unit is 60.

0.

4. The novel natural red slow sugar according to claims 1 and 2, wherein both healthy subjects and diabetic subjects can use it.

5. The novel natural red 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, thereby having a weight loss effect.

6. The novel natural red slow sugar according to claims 1 and 2, wherein the slow sugar has certain nutrition and zero calories. During the manufacturing process of the sugar, due to the action of the acidic oxidant, the sugar can prevent tooth decay by blocking the alcohol function (-OH) after the esterification reaction. After consumption by diabetic subjects, retinopathy, nephropathy and other pathological complications can be slowed down or / and prevented.

7. The novel natural red 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 red slow sugar according to claims 1 and 2, wherein commercial natural white sugar is used to produce 10 kg of such slow sugar according to the following process: - Mix two liters of desalinated water with an acidic oxidant and a mixture of dried plants and seeds; - 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; - Drying the obtained molasses for 30 to 45 minutes by introducing fresh air and then hot air while stirring the molasses at a speed of 30 to 50 rpm.

9. The novel natural red slow-release sugar according to claims 1 and 2 is recommended for athletes who need intense exercise because it has endurance and can protect muscles from cramps.

10. The novel natural granular or powdered red 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 or other shaped products, or for preparing or producing medicines and auxiliary medicines, as well as body care products, health products and cosmetics.

11. The novel natural red 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 red 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. A new type of natural red 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.

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

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

16. The esterification of the two sugars may be homosexual (only the molecules according to claim 14 or 15), i.e. each molecule is esterified separately, or heterosexual (the molecules according to claim 14 and 15), i.e. the glucose molecule and the fructose molecule are esterified together.

17. After glucose is oxidized to gluconic acid, glucose and gluconic acid undergo esterification 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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