OA22215A - Interglycan-esters of sucrose dicarboxylate and fructofuranuronate, their manufacturing process and their use as a slow-release hypoglycemic sugar. - Google Patents

Abstract

The present invention relates to a novel natural brown slow-release sugar, granulated or powdered, and a method for its manufacture based on esterification. The resulting product, namely the novel natural brown slow-release sugar, can be consumed by anyone, regardless of their health status, as it is hypoglycemic and has a blood glucose level below 1 gram. The present invention is based on obtaining a novel natural brown slow-release sugar by esterification characterized by slow, limited, and athermic reactions and comprises a set of dried plant products possessing beneficial health effects. The novel natural brown slow-release sugar obtained through the present invention can be used in all food preparations that typically use commercial white natural sugar, such as cakes, pastries, confectionery, sorbets and ice creams, juices, beverages of all kinds, chocolate-based preparations, cocoa-based preparations, and caramel-based preparations. The novel natural brown slow-release sugar can be consumed without concern for those with dental caries, obesity, retinopathy, or other pathological conditions. <img file="OA22215A_A0001.tif"/>

Description

NEW "NT NATURAL WHITE" SUGAR

AND ITS MANUFACTURING PROCESS

The present invention relates to a new natural white slow-release sugar in granulated or powdered form, and a method for its manufacture. Its production involves an industrial manufacturing process based on esterification and as shown in the figure below, which includes the new molecule of the new slow-release sugar obtained from commercially available natural white sugar (sucrose).

Esterification is a chemical reaction between a carboxylic acid and an alcohol that leads to the formation of esters and water (Fig.1), (Fig.2), (Fig.3) and (Fig.5).

Numerous experimental studies have shown that an equimolar mixture of a carboxylic acid and an alcohol leads to a slow and incomplete transformation.

The esterification reaction of the present invention is described as slow, limited and athermic.

The defining characteristic of the esterification/hydrolysis equilibrium is the dynamic equilibrium in which the two opposing reactions occur simultaneously, and the reactants and products coexist in constant proportions. Indeed, both reactions evolve towards the same equilibrium state.

The present invention is based on obtaining a new natural white slow sugar by esterification characterized by slow, limited and athermic reactions.

- Slow because it is characterized by a release of the new slow sugar at the level of the intestine and this in accordance with the slow secretion of insulin in the case of type 2 diabetes.

- Limited by their reverse reactions since esterification is limited by the hydrolysis of the ester formed.

- Athermal because temperature does not affect the equilibrium.

The new natural white slow sugar, granulated or powdered, of the present invention, is obtained from commercial natural white sugar by esterification on an industrial scale, by the addition of an acid oxidant, the main ingredient, and according to a manufacturing process (Fig. 6), which has made it possible to obtain a new natural white slow sugar acting on consumption p<~ hydrolysis.

Esterification on one side and hydrolysis on the other have achieved a chemical balance in the body, thus allowing control of consumption by the limited nature of the absorption of this sugar which is controlled by the chemical balance resulting from the esterification/hydrolysis ratio (Fig.4).

Thus, in the event that more sugars are consumed than the body requires, the excess sugar is not stored but rather eliminated because esterification and hydrolysis perform the function of constant control.

The present invention relates to a new natural white slow sugar whose manufacturing principle is based on the chemical equilibrium esterification of an alcohol and its hydrolysis.

The chemical equilibrium between esterification and hydrolysis is for esterification (Fig. 1), (Fig. 2), (Fig. 3) and (Fig. 4):

Alcohol (sugar) + carboxylic acid → Ester (new slow-release sugar) + Water

R-C

Carboxylic Acid +R* -OH

Alcohol (Sugar)

+ _H₂O Water

Ester (Slow-release sugar)

The reaction is a dynamic equilibrium between two reactions (esterification/hydrolysis) which are in opposite directions to each other and which occur simultaneously.

In the industrial-scale production of the new natural white slow sugar, the direction of esterification is favoured.

At the point of consumption and at the level of the intestine, the opposite is true, since it is the hydrolysis reaction which is favoured to slowly release (LP) the sugar from the new sugar, namely the ester of the sugar, and this in accordance with the slow and limited secretion of insulin (Fig.4).

The prolonged LP release of sugar from the new natural white slow sugar of the present invention at the level of the intestine is in agreement and similarity with the slow secretion of insulin in the case of type 2 diabetes (Fig. 4).

The chemical basis of the new natural white slow-release sugar of the present invention is obtained by the chemical mechanism of the synthesis of the new slow-release sugar: ¹

OXIDATION (Fig. 5-1):

For sugars, there is firstly a reaction of monosaccharides consisting of an oxidation of saccharic acids making the primary OH groups more easily attacked and which are generally oxidized entirely to the carboxylic acid state.

The resulting product is a polyhydroxydicarboxylic acid called saccharic acid. For example, nitric acid is a good oxidizing agent for the preparation of saccharic acids.

Oxidation of the new natural white slow sugar

OXIDATION and sugars: formation of saccharic acids

Saccharic acid (carboxylic acid, - OOOH)

ESTERIFICATION (Fig. 5-3):

Hydroxy groups in sugars can be esterified using normal methods (Carboxylic acid + Alcohol)!

Carboxylic acids cause reactions involving the carbon of the carboxyl group, by acid-catalyzed nucleophilic addition.

The best-known reaction is Esterification, which is a balanced reaction.

Starting with an equimolar mixture of carboxylic acid and alcohol, the yield is, by moles, 65% ester and water and 35% acid and alcohol. This yield can be improved by increasing the concentration of a reactant or decreasing that of a product (Le Chatelier's principle).

Acid-catalyzed esterification is an important method for the preparation of esters (new slow sugar).

iacOe cvMxYlique - COOHÏ

The new natural white slow-release sugar of the present invention is a slow-release sugar because it is obtained and consumed according to the physicochemical characteristics of the "Esterification/hydrolysis" chemical equilibrium, which are:

- Slow because the release is prolonged LP

- Limited by the reverse reaction

- Athermal because temperature does not change the equilibrium.

The new natural white slow sugar of the present invention is chemically in the form of esters.

By comparison with natural products such as plants like stevia, tannin, and apples, which contain esters, we can deduce that chemical products in ester form are not harmful.

EXTENSION OF THE ESTERIFICATION REACTION (Fig. 10):

Obtaining an ester sugar following the esterification reaction between two types of sugar:

- sugar alcohol (function - OH): commercial white sugar.

- acidic sugar (function — COOH): saccharic acid.

Following the hydrolysis of sucrose into glucose and fructose, these two latter sugars in turn undergo the esterification reaction.

The oxidation of glucose to gluconic acid followed by esterification between glucose and gluconic acid to form an ester of two glucose molecules:

In the same way, the ester sugar is obtained from fructose (Fig. 11).

Slow-release sugars are sugars with a glycemic index below 59.

It was long mistakenly believed that slow-release sugars were complex carbohydrates.

The new natural white slow sugar obtained from the present invention can be used in all food preparations, usually using commercial natural white sugar, such as cakes, pastries, confectionery, sorbets and ice creams, juices, drinks of all kinds, chocolate-based preparations, cocoa-based preparations, caramel-based preparations and others.

The new natural white slow sugar is essential for intense sports that require endurance, whatever their nature, because it is slow to be absorbed into the body, ensuring the maintenance of the energy needed for athletes and therefore it is anti-cramp.

Indeed, the new natural white slow sugar of the present invention is assimilated slowly and therefore remains available during the duration of the effort.

The new natural white slow sugar of the present invention does not cause reactive hypoglycemia, whereas commercial natural white sugar has a rapid release and causes a rapid rise in blood glucose levels, described as dangerous (hyperglycemia).

Slow-release sugars are good for your health; these slow-release sugars have a low glycemic index, which means they release energy continuously into the body.

The glycemic index is a ranking system for carbohydrate-containing foods, based on their effects on blood glucose levels (glucose levels in the blood) during the two hours following ingestion. It allows for a comparison of the glycemic impact of each food, measured directly during digestion.

A low glycemic index for a food means that the level of glucose in the blood rises only very slightly after the digestion of the food in question, as illustrated below.

Low GI (< 35): such as legumes, dairy products, meats

Average GI between 35 and 50: such as bananas, apricots.

High GI (over 50): such as dates, sweets

Therefore, the intensity with which food is ingested in raising blood sugar is expressed by a value called GI.

The new natural white slow sugar of the present invention is therefore a slow sugar characterized by its low GI which is measured in the medical analysis laboratory following the oral induced hyperglycemia protocol: HGPVO.

Since the new sugar is prepared by chemical esterification, the hydrolysis of esters upon ingestion is a slow reaction that is strongly catalyzed by acids.

In the present invention, the primary and secondary alcohol esters, the mechanism is the reverse of that of acid-catalyzed esterification.

Esterification/hydrolysis are therefore in reaction equilibrium.

The manufacture of the new natural white slow sugar is in accordance with the process described below.

To obtain, for example, a quantity of 10 kg of new natural white granulated or powdered slow sugar, it is necessary to make a mixture of demineralized water with an acidic oxidizing catalyst in a vat and heat it to a temperature of 90 to 100 degrees Celsius while stirring it.

Gradually add 10 kg of commercial white sugar to the mixture in the vat, which is still on the stove, for about 10 minutes. Simultaneously, using an electrically powered propeller or paddle mixer, at a speed of 25 to 35 rpm, mix the sugar with the gradually added sugar until a light brown molasses is obtained. This process, called cooking, lasts between 30 and 45 minutes.

After obtaining this molasses, the fire is then extinguished and this molasses undergoes drying under agitation at a speed of 30 to 50 revolutions per minute, under the effect of a blow of fresh air followed by a blow of hot air for a period of 30 to 35 minutes.

At the end of this drying process, the molasses becomes a new, natural, white, granulated slow-release sugar, which is then sieved to obtain a new sugar with a uniform particle size. Sieving results in a weight loss of 300 to 400 grams from the initial 10 kg, which can be identified by the final weight of the new, natural, white, slow-release sugar obtained through the present invention.

If there is a need to produce new natural white slow sugar in powder form, the manufacturing process described must be completed by grinding this new natural white granulated slow sugar obtained after sieving.

Preparing larger quantities follows the same process in terms of time, temperature, and speed as previously described, at all stages, regardless of the weight of the new natural white slow-release sugar to be produced. This requires one or more vats sized to the desired production quantity, equipped with a sufficient number of agitators capable of thoroughly mixing the entire quantity in the vat(s). It is also possible to produce a large quantity by using several vats with a capacity of 10 or 20 kg or more, operated by a control system that triggers simultaneous production.

The new natural white slow sugar of the present invention has a glycemic index located between GI 15 and 36.5 represented by the filled area at the curves (Fig.7) and (Fig.8).

The new natural white slow sugar in granulated or powdered form of the present invention is dietetic, calorie-free, anti-obesity and prevents dental caries.

It is also antidiabetic and therefore prevents retinopathy and nephropathy among others, because the new natural white slow sugar of the present invention is esterified and is characterized by a prolonged LP release under the effect of hydrolysis, the reverse chemical reaction of esterification.

Its consumption is therefore intended for healthy subjects and also for subjects with type 2 diabetes.

Thus, a blood HbAlC level of 7% corresponds to an average blood glucose level of 1.5 g per liter of blood, and 1% more or less of HbAlC represents an average increase or decrease in blood glucose of 0.30 g/liter.

For the new natural white slow-release sugar, granulated or powdered, of the present invention, the following result is obtained:

0.24 x 0.30 = 0.072, which clearly shows that the new natural white slow-release sugar reduces the HbA1c level by 7.2%.

For traditional white sugar from the gossipmonger, and for comparison, the following result:

0.32 x 0.3 = 0.092, which indicates that commercially available white natural sugar increases HbA1c levels by 9.2%.

Slow sugars have long been considered as replacement sugars and not substitute sugars or fake sugars and are often presented in liquid form, except that their preparation does not conform to a manufacturing process resembling the process of the present invention, which is based on the chemical balance "esterification / hydrolysis".

The physicochemical characteristics of the new natural white granulated or powdered slow-release sugar of the present invention, obtained from analyses carried out over 12 months, are shown in the following table of values, which confirms the chemical stabilization of the new sugar. This new sugar is a concentrated medium that can be stored for a long time without deteriorating.

** Settings _PH Carbohydrates Dry extract Total Ash Lead Cadmium Results January 2021 4.86 92.5 99.3 0.1 <001 0.1 FEBRUARY 2021 4.90 92.3 99 3 0.1 <0 01 0.1 March 2021 4.40 93.8 99.3 0.1 <0.01 0.1 April 2021 4.93 92.2 99.4 0 1 <0.01 0.1 May 2021 4.92 93.9 99.3 0 1 <0.01 0.1 June 2021 4.90 92.2 99.3 0.1 <0.01 0.1 July 2021 4.91 924 99.2 0.1 <0.01 0.1 August 2021 4.88 92.0 99.3 0.1 <0.01 0.1 September 2021 4.93 92.2 99.3 0.1 <0.01 0.1 October 2021 4.91 93.8 99.3 0.1 <0.01 0.1 November 2021 4.96 92.2 99.3 0.1 <0.01 0.1 December 2021 4.89 92.3 99.3 0.1 <0.01 21 days

The new natural white slow sugar, granulated or powdered, is nothing other than an equimolar mixture of glucose and fructose obtained by enzymatic or chemical hydrolysis of sucrose.

The hydrolysis of sucrose by oxidant, which normally occurs partially, has given rise to entirely new sucrose.

The new natural white slow sugar granulated or powdered of the present invention is characterized by a refractive index of 1.3412 and a polarization along the Z° unit of 64.9. The glycemic index was measured according to the protocol of the Oral Hyperglycemia Test (OGTT), by making a comparison on the basis of repeated analyses of the new natural white slow sugar on two subjects, which analyses made it possible to note low glycemic indices compared to the traditional white sugar from the market taken as a control and whose glycemic index is very high (Fig.9).

The esterified sugar molecules of the new natural white slow sugar, that is to say esterified Sucrose, esterified Glucose and esterified Fructose in double molecule, homo or hetero are really and inevitably chemically synthesizable, namely: Glucose-Glucose, Fructose-Fructose, Glucose-Fructose and Sugar-Sugar.

Fructose - Fructose

homo

This is argued and proven by the results obtained from the Esterification Indices IE, calculated by Saponification Index IS and Acid Index IA (IE = IS - IA) according to the French Pharmacopoeia tenth edition.

ACID VALUE SAPONIFICATION INDEX ESTER CLUE n(mL) 1.35 nl(mL) 1.2 IE=IS-IA m(g) 10 n2(mL) 1.31 IS = 3.0855 m(g) 1 IA = 0.75735 IA = 0.75735 IS = 3.0855 IE = 2.32815

All the esterified sugar molecules designated in the present invention are called SATTAR and are obtained by:

OXIDATION: all primary OH groups of sucrose, glucose and fructose are attacked more easily and are generally oxidized completely to the carboxylic acid state.

ESTERIFICATION: to ensure subsequent esterification, these molecules react with the sugar alcohol molecules, in corresponding homomolecular and/or heteromolecular form (Fig.5-2a) and (Fig.5-2b).

Claims (17)

1- New natural white slow sugar granulated or powdered, in that it is obtained by a manufacturing process based on esterification starting from commercial natural white sugar through oxidation carried out by an acid oxidant and esterification of sugars by the same acid oxidizing catalyst in order to obtain Esters in accordance with the new molecule below. 2- New natural white slow sugar granulated or powdered of claim 1 retaining the sweetening power of commercial natural white sugar and characterized by its low glycemic index between GI 15 and 36.5. 3- New natural white slow sugar granulated or powdered of claims 1 and 2 characterized by a refractive index of 1.3412 and polarization unit Z° 64.9. 4- New natural white slow sugar, of claims 1 and 2 which can be consumed by subjects with type 2 diabetes. 5- New natural white slow sugar of claims 1 and 2 anti-obesity by the effect of non-storage and elimination of excess sugar consumed, thanks to the chemical balance esterification/hydrolysis acting in accordance with the slow secretion of insulin in the body. 6- New natural white slow sugar of claims 1 and 2 in that it is dietetic and without calorie intake, preventing dental caries by blocking the alcohol (-OH) function and can be consumed by diabetic subjects to slow down and/or prevent retinopathy and nephropathy and other pathological complications. 7- New natural white slow sugar of claims 1 and 2 in liquid solution, in syrup, in paste, in cream, in honey or in caramel. 8- Manufacturing process for example of 10 kg of New natural white slow sugar granulated or powdered of claims 1 and 2 according to the following: - Mix two liters of demineralized water with an acid oxidant. - Heat and stir for 10 minutes in a pot over a fire to reach 90 to 100 degrees Celsius. - Add 10 kg of commercially available natural white sugar to the mixture. - Cook while stirring at a speed of 25 to 35 revolutions per minute. - Dry the molasses obtained with fresh air and then with hot air, for 30 to 45 minutes and under agitation at a speed of 30 to 50 revolutions per minute. 9- New natural white slow sugar recommended for athletes prat222t5 intense sports, for its character ensuring a prolonged release and because it carries characteristics offering endurance and preserving muscles against cramps. 10- Property of the new natural white slow sugar granulated or powdered used as a raw material for the manufacture of products in liquid, pasty, creamy, honeyed or caramelized forms or other forms of claims 1, 2, and 8 for the preparation or production of pharmaceutical and parapharmaceutical products as well as for body care, wellness and cosmetic products. 11- New natural white slow sugar of claims 1 and 2 obtained by chemical equilibrium esterification/hydrolysis having the characteristics of slow, limited and athermic. 12- New natural white slow sugar of claims 1 and 2 obtained by a reaction between sugar alcohol (sucrose) and an acid sugar (saccharic acid) which is obtained by oxidation of the sugar alcohol. 13- Novel natural white slow sugar of claims 1 and 2 prepared using the same acid oxidizing catalyst jointly for sugar oxidation and for esterification. 14- New natural white slow sugar, slow when ingested in the intestine of the organism characterized by its prolonged LP release in accordance with insulin secretion. 15- New natural white slow-release sugar chemically in ester form, with regard to glucose, according to the following molecule: 16- New natural white slow-release sugar chemically in the form of esters, with regard to fructose, according to the following molecule: 17- The esterification of two sugars can be homo (molecule of claim 15 alone or of claim 16 alone) i.e. esterification of each molecule separately or hetero (molecules of claims 15 and 16) i.e. esterification of the glucose molecule and the fructose molecule together.