Sugar composition

Field of the invention

The present invention relates to sugar compositions and processes for the preparation of sugar. In particular, the present invention relates to low glycaemic sugar, processes for the preparation of the sugar, products containing the sugar and uses for the sugar.

Background of the invention

There is concern that refined white sugar is causal in the development of diabetes and obesity. There is strong demand for healthier sugar products.

Refined white sugar has been prepared by substantially similar processes for a long time. Following harvest, sugar cane is shredded and crushed to create sugar juice. The juice is clarified and heated under vacuum to concentrate it by evaporation. The resulting syrup can crystallise as it thickens or be seeded to produce sugar crystals. Molasses is the viscous syrup that remains after crystallisation. The molasses is removed to leave a dense suspension of sugar crystals in the remaining syrup that is called massecuite. The massecuite is at least washed in a centrifuge and then dried to produce bulk unrefined sugar.

This bulk unrefined sugar is refined at a refinery to produce food grade refined crystalline white sugar, which is generally 99.5% sucrose. The refining process used to prepare refined white sugar removes most vitamins, minerals and phytochemical compounds from the sugar leaving a“hollow nutrient”, that is, a food without significant nutritional value beyond its calorific content.

Developing low glycaemic sugars is useful because it is thought that individuals who are susceptible to type II diabetes and coronary heart disease should follow a low glycaemic diet. Preparation of sugars with better nutritional content than white sugar is also useful.

Low hygroscopicity is important because hygroscopicity makes sugars difficult to use and store, which is of particular relevance given sugar cane is grown in humid climates. Hygroscopicity is particularly disadvantageous in an industrial setting because of the tendency for the sugar to clump and stick to equipment. Working with hygroscopic sugar in an industrial setting may require, for example, equipment operating under nitrogen to minimise the quantity of sugar that clumps or sticks to the equipment. There is also a need for sugars with low hygroscopicity that are low glycaemic and/or have improved nutritional value.

Reference to any prior art in the specification is not an acknowledgment or suggestion that this prior art forms part of the common general knowledge in any jurisdiction or that this prior art could reasonably be expected to be understood, regarded as relevant, and/or combined with other pieces of prior art by a skilled person in the art.

Summary of the invention

A low glycaemic sugar with a glycaemic index (Gl) of about 50 had been developed previously. That sugar had about 20 to 45 mg CE polyphenols/100 carbohydrate. The prior art sugars with 60 mg CE polyphenols/100 g carbohydrate were not low glycaemic and had borderline medium/high Gl (ie about 68-70). At that time, it was thought that the low Gl of 50 was about as low as was achievable for a sugar consisting largely of sucrose (ie a medium Gl sugar).

The inventor of the present invention has surprisingly developed a low glycaemic sugar with improved nutrient content, in particular higher polyphenol content. Preferably the sugar also has low hygroscopicity.

Even more surprisingly, the inventor of the present invention has developed the first very low glycaemic sugar, achieving a Gl of about 15, which is significantly less than half of the Gl of previous low glycaemic sucrose sugars (ie about 50). It is highly surprising that a sugar can be prepared that is very low glycaemic. In addition, it is surprising that the very low glycaemic sugar is palatable and an effective sweetener.

In one aspect, the present invention provides a very low glycaemic sugar comprising at least about 80% w/w sucrose. Optionally, the sugar has 46 mg CE polyphenols/100 g carbohydrate to about 100 mg CE polyphenols/100 g carbohydrate or about 37 mg GAE polyphenols/100 g carbohydrate to about 80 mg GAE polyphenols/100 g carbohydrate. Optionally, the sugar has 0 to 1.5 % w/w reducing sugars, wherein the sugar is not more than 0.5% w/w fructose and not more than 1% w/w glucose.

In another aspect, the present invention provides a sugar comprising at least about 80% w/w sucrose and about 46 mg CE polyphenols/100 g carbohydrate to about 100 mg CE polyphenols/100 g carbohydrate or about 37 mg GAE polyphenols/100 g carbohydrate to about 80 mg GAE polyphenols/100 g carbohydrate, wherein the sugar is low glycaemic.

In an alternate aspect, the present invention provides a sugar comprising at least about 80% w/w sucrose, about 46 mg CE polyphenols/100 g carbohydrate to about 100 mg CE polyphenols/100 g carbohydrate or about 37 mg GAE polyphenols/100 g carbohydrate to about 80 mg GAE polyphenols/100 g carbohydrate and 0 to 1.5 % w/w reducing sugars, wherein the sugar is not more than 0.5% w/w fructose and not more than 1 % w/w glucose.

In an alternate aspect, the present invention provides a sugar comprising sucrose, reducing sugars and polyphenols, wherein the sugar comprises about 46 mg CE polyphenols/100 g carbohydrate to about 100 mg CE polyphenols/100 g carbohydrate or about 37 mg GAE polyphenols/100 g carbohydrate to about 80 mg GAE polyphenols/100 g carbohydrate and 0 to 1.5 % w/w reducing sugars, wherein the sugar is low glycaemic.

The polyphenols in the sugars of the invention are optionally polyphenols that are found endogenously in sugar cane. The polyphenols in the sugars of the invention may be synthetic or isolated from a plant, for example, sugar cane. Preferably, the polyphenols are isolated from sugar cane or a sugar cane derived product, such as a sugar processing waste stream. The polyphenols preferably include flavonoids. Preferably, the polyphenols include one or more of tricin, luteolin and apigenin. Alternatively, the polyphenols include tricin. In some embodiments of the invention the amount of polyphenols in the sugar is about 46 mg CE/100 g to about 100 mg CE/100 g, about 47 mg CE/100 g to about 90 mg CE/100 g, about 48 mg CE/100 g to about 80 mg CE/100 g, about 49 mg CE/100 g to about 70 mg CE/100 g or about 50 mg CE/100 g to about 65 mg CE/100 g carbohydrate. In preferred embodiments of the invention, the polyphenol content is about 50 mg CE /100 g to about 65 mg CE /100 g carbohydrate in the sugar. In preferred embodiments, the polyphenol content is about 60 mg CE/100 g carbohydrate in the sugar.

There are multiple options for the measurement of polyphenol content. One option is to measure milligrams catechin equivalents (CE). An alternative is to measure gallic acid equivalents (GAE). Amounts in mg CE polyphenols/100 g carbohydrate can be converted to mg GAE polyphenols/100 g carbohydrate by multiplying by 0.81 ie 60 mg CE polyphenols/100 g is 49 mg GAE polyphenols/100 g. The quantities of polyphenols in sugars of the invention can also be about 37 mg GAE/100 g to about 80 mg GAE/100 g, about 38 mg GAE/100 g to about 70 mg GAE/100 g, about 39 mg GAE/100 g to about 60 mg GAE/100 g, about 40 mg GAE/100 g to about 55 mg GAE/100 g or about 45 mg GAE/100 g to about 55 mg CE/100 g carbohydrate. In preferred embodiments of the invention, the polyphenol content is about 45 mg GAE /100 g to about 55 mg GAE /100 g carbohydrate. In preferred embodiments, the polyphenol content is about 50 mg GAE/100 g carbohydrate.

The sugar of the present invention is low glycaemic. In some embodiments, the sugar is very low glycaemic. In particular, the sugar particles of the invention are preferred to have a glucose based glycaemic index of less than 45, optionally less than 30. Optionally, the glucose based glycaemic index is from about 5 to about 45, from about 5 to about 40, from about 5 to about 35, from about 5 to about 30, from about 5 to 25, from about 10 to about 30, from about 10 to about 35 or from about 10 to about 40. In preferred embodiments of the invention, the glucose based glycaemic index of the sugar particles is from about 10 to about 30.

In some embodiments, 10 g of the sugar of the invention has a glycaemic load of 8 or less, 6 or less, 4 or less, 3 or less or 2 or less. Optionally, 10 g of the sugar of the invention has a glycaemic load of 1 to 4.

In some embodiments, the sugar further comprises reducing sugars. Optionally, the reducing sugar content of the sugar is about 0.001% to 1.5%, 0.001% to 1.2%, 0.001% to 1%, 0 to 0.6%, 0.001% to 0.5%, 0 to 0.3%, 0.001% to 0.2%, 0 to 0.15%, 0.001% to 0.15%, 0.01 to 0.1% w/w of the sugar. Optionally, the reducing sugars are glucose and fructose. Optionally, the glucose to fructose ratio is 0.8 to 1.2. Optionally, the reducing sugar content is not more than 50% glucose. In preferred embodiments, the quantity of fructose is not more than 0.5% w/w or 0.3% w/w of the sugar. It is also preferred that the sugar has low hygroscopicity. Low hygroscopicity is useful for industrial processing because it allows the sugar to be handled by industrial equipment in an unaltered atmosphere (ie not under nitrogen) without significant clumping or sticking to the equipment. If a sugar is too hygroscopic, it is difficult to use that sugar industrially in the production of foods and beverages. Low hygroscopicity is also likely to improve the shelf life of the sugar product. Without being bound by theory, it is thought that sugar particles of the invention have lower hygroscopicity than previous low Gl sugars because they have lower reducing sugar content. Preferred sugars of the invention have 0 to 0.5% w/w, 0 to 0.3% w/w or 0 to 0.15% w/w of the hygroscopic reducing sugar fructose.

It is preferred that the sugar has low levels of the high Gl sugar glucose. Preferred sugars of the invention have 0 to 1% w/w, 0 to 0.5% w/w, 0 to 0.3% w/w or 0 to 0.15% w/w of the high Gl sugar glucose.

Optionally, the sugar of the invention comprises 0 to 1% w/w reducing sugars of which 0 to 0.5% w/w is fructose and 0 to 0.5% w/w is glucose. Alternatively, the sugar of the invention comprises 0 to 1.5% w/w reducing sugars of which 0 to 0.5% w/w is fructose and 0 to 1% w/w is glucose. Alternatively, the sugar of the invention comprises 0 to 0.6% w/w reducing sugars of which 0 to 0.3% w/w is fructose and 0 to 0.3% w/w is glucose.

In some embodiments of the present invention, the sugar is 85% or more w/w sucrose, 90% or more w/w sucrose, 95% or more w/w sucrose. Alternatively, the sugar is 98% or more w/w sucrose. Alternatively, the sugar is 99% or more w/w sucrose.

In some embodiments, the sugar of the present invention has a moisture content of 0.02% to 0.6%, 0.02 to 0.3%, 0.02% to 0.2%, 0.1% to 0.5%, 0.1% to 0.4%, 0.1 to 0.2%, 0.2% to 0.3% or 0.3 to 0.4% w/w. Alternatively, the moisture content is 0.02 to 0.5% w/w.

It is preferred that the sugar particles have moisture content as described above when they are manufactured and have 0.02% to 1%, 0.02% to 0.8%, 0.02% to 0.6%,

0.1% to 0.5%, 0.1% to 0.4% or 0.2% to 0.3% w/w moisture content after 6 months storage at room temperature and 40% relative humidity or, alternatively, after 12 months storage at room temperature and 40% relative humidity. Alternatively, the increase in moisture content of the sugar particles is a maximum of 0.3% over the 2 year shelf life for the sugar particles. The sugar particles of the invention retain the above low moisture content after storage because of their low hygroscopicity. Without being bound by theory, the lower hygroscopicity is thought to be a result of the low reducing sugar content (in particular the fructose content) of the sugar particles of the invention.

In some embodiments, the present invention provides a sugar wherein a first proportion of the polyphenols are entrained within the sucrose crystals and a second proportion of the polyphenols is distributed on the surfaces of the sucrose crystals. The first portion of the polyphenols is endogenous to sugar cane and has been retained within the sucrose crystals during preparation of the sugar, for example, by incomplete washing of the massecuite. The second portion of polyphenols may be but is not required to be endogenous to sugar cane. Part or all of the second portion may be added to the sugar product by spraying polyphenols onto the sucrose crystals. The total amount of polyphenols is efficacious for achieving a low glycaemic sugar in the presence of low reducing sugar content, particularly low glucose content, as described elsewhere.

In some embodiments of the present invention, the sugar has about 60% to 100% of the polyphenols outside sugar crystals and about 0% to 40% of the polyphenols within the sucrose crystals (ie up to 40% entrained). Alternatively, about 70% to 100% of the polyphenols are on the outside of the sugar particles and about 0% to 30% of the polyphenols are within the sucrose crystals, about 70% to 95% of the polyphenols are on the outside of the sugar particles and about 5% to 30% of the polyphenols are the sucrose crystals are within the sucrose crystals.

In some embodiments of the present invention, the sugar falls within the maximum residue limits for chemicals set out in Schedule 20 of the Australian Food Standards Code in force July 2017. In some embodiments of the present invention, the sugar falls within the maximum residue limits for chemicals set out the regulations governing food grade products in the US, Europe, Japan, China or Canada. Sugar prepared by the method described in WO 2018/018090 has been demonstrated to meet these requirements. Sugars of this invention, prepared by adding polyphenol content to a sugar prepared by that method will meet these requirements so long as the polyphenol source has minimal pesticides or herbicides. Optionally, the sugar meets the following pesticide/herbicide levels: less than 5 mg/kg 2,4-dichlorophenoxyacetic acid, less than 0.05 mg/kg paraquat, less than 0.05 mg/kg ametryn, less than 0.1 mg/kg atrazine, less than 0.02 mg/kg diuron, less than 0.1 mg/kg hexazinone, less than 0.02 mg/kg tebuthiuron, less than 0.03 mg/kg glyphosate, a combination of these or all of these.

Alternatively, the sugar comprises the following pesticide/herbicide levels: less than 0.005 mg/kg 2,4-dichlorophenoxyacetic acid, less than 0.01 mg/kg diquat, less than 0.01 g/kg paraquat, less than 0.01 mg/kg ametryn, less than 0.01 mg/kg atrazine, less than 0.05 mg/kg bromacil, less than 0.01 mg/kg diuron, less than 0.05 g/kg hexazinone, less than 0.01 mg/kg simazine, less than 0.01 mg/kg tebuthiuron, less than 0.01 mg/kg glyphosate, a combination of these or all of these.

The sugar of the invention is preferably food grade.

The sugars of the invention are solids. However, syrup and liquid sugars are also contemplated. In liquid or syrup versions of the sugar of the invention the amount of sucrose is measured by solid weight and equivalent to the w/w% amounts for the solid sugars of the invention. Syrup and liquid versions of the sugars of the invention can be prepared by the addition of solvents such as water to the sugars of the invention. It is also possible to prepare a liquid or syrup sugar composition with the sucrose and polyphenol quantities described for the solid sugars of the invention and optionally the reducing sugar, glucose, fructose and pesticide/herbicide levels described for the solid sugars of the invention. These are liquid or syrup sugars of the invention.

Foods and beverages

In a further aspect, the present invention provides a food or beverage comprising one or more sugars of the present invention. In a further aspect, the present invention provides a method of preparing a food or beverage comprising combining a sugar of the present invention with one or more ingredients suitable for consumption.

In another aspect, the present invention provides a food or beverage comprising sucrose and polyphenols, wherein the sucrose and polyphenols are either added to the food or beverage in the form of a sugar of the invention or the sugar of the invention is formed in situ by separately adding the sugar and polyphenols to the food or beverage such that the polyphenols are equivalent to 46 mg CE polyphenols/100 g sucrose to about 100 mg CE polyphenols/100 g sucrose or about 37 mg GAE polyphenols/100 g sucrose to about 80 mg GAE polyphenols/100 g sucrose.

In some embodiments of the invention the amount of polyphenols is about 46 mg CE/100 g to about 100 mg CE/100 g, about 47 mg CE/100 g to about 90 mg CE/100 g, about 48 mg CE/100 g to about 80 mg CE/100 g, about 49 mg CE/100 g to about 70 mg CE/100 g or about 50 mg CE/100 g to about 65 mg CE/100 g sucrose (about 37 mg GAE/100 g to about 80 mg GAE/100 g, about 38 mg GAE/100 g to about 70 mg GAE/100 g, about 39 mg GAE/100 g to about 60 mg GAE/100 g, about 40 mg GAE/100 g to about 55 mg GAE/100 g or about 45 mg GAE/100 g to about 55 mg CE/100 g sucrose). In preferred embodiments of the invention, the polyphenol content is about 50 mg CE /100 g to about 65 mg CE /100 g sucrose (about 45 mg GAE /100 g to about 55 mg GAE /100 g sucrose). In preferred embodiments, the polyphenol content is about 60 mg CE/100 g sucrose (about 50 mg GAE/100 g sucrose). The amount of polyphenol to sucrose can be determined, even where there are other carbohydrate present in the food or beverage, indirectly from the amounts of polyphenols and the amounts of sugar in the food or beverage.

In a further aspect, the present invention provides a food or beverage comprising carbohydrate and about 46 mg CE polyphenols/100 g carbohydrate to about 100 mg CE polyphenols/100 g carbohydrate or about 37 mg GAE polyphenols/100 g carbohydrate to about 80 mg GAE polyphenols/100 g carbohydrate, wherein the majority of the carbohydrate are sucrose and the food or beverage is low glycaemic.

In some embodiments of the invention the amount of polyphenols is about 46 mg CE/100 g to about 100 mg CE/100 g, about 47 mg CE/100 g to about 90 mg CE/100 g, about 48 mg CE/100 g to about 80 mg CE/100 g, about 49 mg CE/100 g to about 70 mg CE/100 g or about 50 mg CE/100 g to about 65 mg CE/100 g carbohydrate (about 37 mg GAE/100 g to about 80 mg GAE/100 g, about 38 mg GAE/100 g to about 70 mg GAE/100 g, about 39 mg GAE/100 g to about 60 mg GAE/100 g, about 40 mg GAE/100 g to about 55 mg GAE/100 g or about 45 mg GAE/100 g to about 55 mg CE/100 g carbohydrate). In preferred embodiments of the invention, the polyphenol content is about 50 mg CE /100 g to about 65 mg CE /100 g carbohydrate (about 45 mg GAE /100 g to about 55 mg GAE /100 g carbohydrate). In preferred embodiments, the polyphenol content is about 60 mg CE/100 g carbohydrate (about 50 mg GAE/100 g carbohydrate).

Suitable foods include bread, cereal, chocolate and confectionary. Suitable beverages include fruit juices, tea-based drinks, milk-based drinks, soy milk-based drinks, nut juice-based drinks (eg almond milk) and soft drinks.

Preparing sugars of the invention

Sugars of the present invention may be prepared from massecuite.

In one aspect, the present invention provides a method comprising addition of an additive comprising polyphenols to a first sugar to produce a second sugar, wherein: the first sugar comprises about 0 to about 80 mg CE polyphenols/100 g carbohydrate or about 0 to about 65 mg GAE polyphenols/100 g carbohydrate and 0 to 1.5% w/w reducing sugar; and the second sugar comprises about 46 mg CE polyphenols/100 g carbohydrate to 100 mg CE polyphenols/100 g carbohydrate or about 37 mg GAE polyphenols/100 g carbohydrate to about 80 mg GAE polyphenols/100 g carbohydrate and 0 to 1% w/w reducing sugar.

The additive may be added in either powder or liquid form. In some embodiments a powder additive is preferred to avoid the need for further drying steps. Optionally the addition of the additive is by a spray process. The first sugar is optionally a cane sugar or a beet sugar. The first sugar can also be a partially refined sugar prepared by a primary sugar mill. The additive is optionally a sugar cane derivative or extract. The skilled person can determine the amount of polyphenol content in the first sugar and then determine the concentration of polyphenol in the additive and the amount of additive necessary to prepare the second sugar. The additive optionally contains a maximum of 0.5% fructose and/or 0 to 10%, 0 to 5% or 0 to 2.5 % reducing sugar. The additive optionally contains 0 to 5%, 0 to 2.5% or 0 to 1 % glucose. The additive optionally contains 0 to 5% sucrose.

In one aspect, the present invention provides a method for preparing a second sugar comprising: (i) washing sugar cane massecuite or an unrefined sugar including sucrose crystals, polyphenols and reducing sugars to remove an amount of polyphenols and an amount of reducing sugars from the massecuite and produce a first sugar; and

(ii) addition of an additive comprising polyphenols to the first sugar to prepare the second sugar; wherein the first sugar comprises about 0 to 1% w/w reducing sugars and optionally about 0 mg CE polyphenols/100 g carbohydrate to about 80 mg CE polyphenols/100 g carbohydrate or about 0 to about 65 mg GAE polyphenols/100 g carbohydrate and the second sugar comprises about 46 mg CE polyphenols/100 g carbohydrate to 100 mg CE polyphenols/100 g carbohydrate or about 37 mg GAE polyphenols/100 g carbohydrate to about 80 mg GAE polyphenols/100 g carbohydrate and 0 to 1% w/w reducing sugar. Optionally, the second sugar is low glycaemic or very low glycaemic. Optionally, the second sugar has a Gl of 45 or less.

In one aspect, the present invention provides a method for preparing a second sugar comprising: washing with an additive comprising polyphenols a first sugar to prepare the second sugar, such that the second sugar has a lower amount of reducing sugars, wherein the first sugar is sugar cane massecuite or an unrefined sugar including sucrose crystals, polyphenols and reducing sugars; wherein the first sugar comprises about 0 to 1% w/w reducing sugars and optionally about 0 mg CE polyphenols/100 g carbohydrate to about 80 mg CE polyphenols/100 g carbohydrate or about 0 to about 65 mg GAE polyphenols/100 g carbohydrate and the second sugar comprises about 46 mg CE polyphenols/100 g carbohydrate to 100 mg CE polyphenols/100 g carbohydrate or about 37 mg GAE polyphenols/100 g carbohydrate to about 80 mg GAE polyphenols/100 g carbohydrate and 0 to 1% w/w reducing sugar. Optionally, the second sugar is low glycaemic or very low glycaemic. Optionally, the second sugar has a Gl of 45 or less. The second sugar in methods above is a sugar of the invention and may have the other features of sugars of the invention described elsewhere. In some embodiments of the methods above, the first sugar does not contain significant polyphenols (eg about 0 to 1 mg GAE/100 g) or reducing sugars (eg about 0 to 0.01% w/w) (ie it was washed and otherwise refined to white refined sugar before the addition of the additive). Alternatively, the first sugar has 0-40 mg CE polyphenols/100 g carbohydrate or 0-35 mg GAE polyphenols/100 g carbohydrate. In some embodiments, the first sugar has about 0 polyphenol content. In alternate embodiments the first sugar has about 10 to about 80 mg CE polyphenols/100 g carbohydrate or about 10 to about 65 mg GAE polyphenols/100 g carbohydrate. In some embodiments, the first sugar is low glycaemic.

In some embodiments, the massecuite has 200-400 mg CE polyphenols/100 g carbohydrate. In preferred embodiments, the massecuite has 240-320 mg CE polyphenols/100 g carbohydrate. In some embodiments of the invention, washing the massecuite removes 165-380 mg CE polyphenols/100 g carbohydrate. In preferred embodiments, washing the massecuite removes 220-300 mg CE polyphenols/100 g carbohydrate.

In some embodiments of the invention, the washing of the massecuite removes the herbicides and/or pesticides that can be present in massecuite resulting in sugar particles that fall within the maximum residue limits for chemicals set out in Schedule 20 of the Australian Food Standards Code in force July 2017. In some embodiments of the present invention, the washing of the massecuite removes the herbicides and/or pesticides that can be present in massecuite resulting in sugar particles that fall within the maximum residue limits for chemicals set out in the regulations governing food grade products in the US, Europe, Japan, China or Canada. Optionally, the washing of the massecuite removes the herbicides and/or pesticides that can be present in massecuite resulting in sugar particles that meet the following pesticide/herbicide levels: less than 5 mg/kg 2,4-dichlorophenoxyacetic acid, less than 0.05 mg/kg paraquat, less than 0.05 mg/kg ametryn, less than 0.1 mg/kg atrazine, less than 0.02 mg/kg diuron, less than 0.1 mg/kg hexazinone, less than 0.02 mg/kg tebuthiuron, less than 0.03 mg/kg glyphosate, a combination of these or all of these.

Alternatively, the washing of the massecuite removes the herbicides and/or pesticides that can be present in massecuite resulting in sugar particles that meet the following pesticide/herbicide levels: less than 0.005 mg/kg 2,4-dichlorophenoxyacetic acid, less than 0.01 mg/kg diquat, less than 0.01 mg/kg paraquat, less than 0.01 mg/kg ametryn, less than 0.01 mg/kg atrazine, less than 0.05 mg/kg bromacil, less than 0.01 mg/kg diuron, less than 0.05 mg/kg hexazinone, less than 0.01 mg/kg simazine, less than 0.01 mg/kg tebuthiuron, less than 0.01 mg/kg glyphosate, a combination of these or all of these.

The present invention has a number of specific forms. Additional embodiments of these forms are as discussed elsewhere in the specification. Preferred forms of the invention include the following.

Embodiments of the present invention provide food grade very low glycaemic sugar comprising at least about 90% w/w or 95% w/w sucrose. Alternatively, the present invention provides an edible very low glycaemic sugar comprising at least about 98% w/w sucrose or 99% w/w sucrose. The sugars of this embodiment optionally comprise: (i) about 37 mg GAE polyphenols/100 g carbohydrates to about 80 mg GAE polyphenols/100 g carbohydrates, (ii) 0 to 1.5 % w/w reducing sugars, wherein the sugar is not more than 0.5% w/w fructose and not more than 1% w/w glucose, and/or (iii) a moisture content of 0.02% to 0.6%.

Embodiments of the present invention provide food grade solid very low glycaemic sugar comprising at least about 90% or 95% w/w sucrose, about 37 mg GAE polyphenols/100 g carbohydrates to about 80 mg GAE polyphenols/100 g carbohydrates and 0 to 1.5 % w/w reducing sugars, wherein the sugar is not more than 0.5% w/w fructose and not more than 1 % w/w glucose.

Embodiments of the present invention provide food grade solid very low glycaemic sugar comprising at least about 98% or 99% w/w sucrose, about 37 mg GAE polyphenols/100 g carbohydrates to about 80 mg GAE polyphenols/100 g carbohydrates and 0 to 1.5 % w/w reducing sugars, wherein the sugar is not more than 0.5% w/w fructose and not more than 1 % w/w glucose.

Embodiments of the present invention provide food grade very low glycaemic sugar liquid or syrup comprising at least about 90% or 95% sucrose by solid weight, about 37 mg GAE polyphenols/100 g carbohydrates to about 80 mg GAE polyphenols/100 g carbohydrates and 0 to 1.5 % reducing sugars by solid weight, wherein the sugar is not more than 0.5% fructose by solid weight and not more than 1 % glucose by solid weight.

Embodiments of the present invention provide food grade very low glycaemic sugar liquid or syrup comprising at least about 98% or 99% sucrose by solid weight, about 37 mg GAE polyphenols/100 g carbohydrates to about 80 mg GAE polyphenols/100 g carbohydrates and 0 to 1.5 % reducing sugars by solid weight, wherein the sugar is not more than 0.5% fructose by solid weight and not more than 1 % glucose by solid weight.

Optionally, the above preferred very low glycaemic forms of the invention comprise about 45 mg GAE polyphenols/100 g carbohydrate to about 55 mg GAE polyphenols/100 g carbohydrate.

Embodiments of the present invention provide food grade solids sugars comprising at least about 95% w/w sucrose, about 37 mg GAE polyphenols/100 g carbohydrates to about 80 mg GAE polyphenols/100 g carbohydrates and 0 to 1.5 % w/w reducing sugars, wherein the sugar is not more than 0.5% w/w fructose and not more than 1% w/w glucose. Embodiments of the present invention provide food grade sugar liquids or syrups comprising at least about 95% sucrose by solid weight, about 37 mg GAE polyphenols/100 g carbohydrates to about 80 mg GAE polyphenols/100 g carbohydrates and 0 to 1.5 % reducing sugars by solid weight, wherein the sugar is not more than 0.5% w/w fructose and not more than 1% w/w glucose. Optionally, these sugars are low glycaemic. Optionally, these sugars comprise about 38 mg GAE polyphenols/100 g carbohydrates to about 70 mg GAE polyphenols/100 g carbohydrates or about 39 mg GAE polyphenols/100 g carbohydrates to about 60 mg GAE polyphenols/100 g carbohydrates.

Embodiments of the present invention provide food grade solid crystalline sugars comprising at least about 95% w/w sucrose, about 37 mg GAE polyphenols/100 g carbohydrates to about 80 mg GAE polyphenols/100 g carbohydrates and 0 to 1.5 % w/w reducing sugars, wherein the sugar is not more than 0.5% w/w fructose and not more than 1% w/w glucose and wherein the sugar has a first proportion of the polyphenols are entrained within the sucrose crystals and a second proportion of the polyphenols is distributed on the surfaces of the sucrose crystals. Optionally, about 70% to 95% of the polyphenols are on the outside of the sugar particles and about 5% to 30% of the polyphenols are the sucrose crystals are within the sucrose crystals.

Embodiments of the present invention provide a method for preparing a food grade solid crystalline sugar comprising:

(i) washing sugar cane massecuite or an unrefined sugar including sucrose crystals, polyphenols and reducing sugars to remove an amount of polyphenols and an amount of reducing sugars from the massecuite and produce a first sugar; and

(ii) addition of an additive comprising polyphenols to the first sugar to prepare the second sugar; wherein the first sugar comprises about 0 to 1% w/w reducing sugars and optionally about 0 to about 1 mg GAE polyphenols/100 g carbohydrate and the second sugar comprises about 37 mg GAE polyphenols/100 g carbohydrate to about 80 mg GAE polyphenols/100 g carbohydrate and 0 to 1% w/w reducing sugar. Optionally, the second sugar is about 45 mg GAE polyphenols/100 g carbohydrate to about 55 mg GAE polyphenols/100 g carbohydrate and very low glycaemic. Optionally, the first sugar is white refined sugar cane or beet sugar.

As used herein, except where the context requires otherwise, the term "comprise" and variations of the term, such as "comprising", "comprises" and "comprised", are not intended to exclude further additives, components, integers or steps.

Further aspects of the present invention and further embodiments of the aspects described in the preceding paragraphs will become apparent from the following description, given by way of example and with reference to the accompanying drawings.

It will be understood that the invention disclosed and defined in this specification extends to all alternative combinations of two or more of the individual features mentioned or evident from the text or drawings. All of these different combinations constitute various alternative aspects of the invention. Brief description of the drawings

Figure 1 shows a graph of Gl v polyphenol content in mg CE polyphenols/100 g of sucrose sugars prepared by washing massecuite to various polyphenol contents. This figure shows sugars have low Gl at about 22-32 mg CE polyphenols/100 g carbohydrate. Previously when the sugar was prepared with 60-70 mg CE polyphenols/100 g carbohydrate content, the sugar had a medium Gl of about 68.

Figure 2 graphs the results of a study on the effect of polyphenol content on the Gl of sucrose in the form of traditional refined white sugar. With no polyphenol content the sugar had the Gl of sucrose (68). 15 mg CE polyphenols/100 g carbohydrate slightly lowered the Gl to about 66. 30 mg CE polyphenols/100 g carbohydrate lowered the Gl to the low Gl of about 50 in accordance with the previous low Gl obtained in Figure 1. Surprisingly an increase to 60 mg CE polyphenols/100 g carbohydrate lowered the Gl to less than about 20, which is a dramatic and unexpected drop in Gl. Finally, an increase in the polyphenol content to 120 mg CE polyphenols/100 g carbohydrate resulted in a surprising and steep increase in the Gl to above about 68, which is at about or higher than the original Gl of the sucrose and unexpectedly indicates that the Gl lowering effect of the polyphenols is negligible at that dose.

Figure 3 charts the results of a study on the effect of polyphenol content or polyphenol plus reducing sugar content on the Gl of sucrose in the form of traditional refined white sugar. 30, 60 and 120 mg CE polyphenols/1 OOg sucrose content was tested and the results similar to those in Figure 3. However, the Gl for 60 mg CE polyphenols/100 g sucrose was shown to be about 15. Adding 0.6 % w/w reducing sugars (1 :1 glucose to fructose) to the 30 mg CE polyphenols/100 g sucrose sugar raised the Gl from 53 to 70. Adding 0.6 % w/w reducing sugars (1 :1 glucose to fructose) to the 60 mg CE polyphenols/100 g sucrose raised the Gl from 15 to 29. Adding 1.2% w/w reducing sugars (1 :1 glucose to fructose) to the 120 mg CE polyphenols/100 g sucrose increased the Gl from 65 to 75. The presence of reducing sugar consistently increased the Gl.

Figure 4 graphs the Gl of several samples from Table 3 in Example 4. Detailed description of the embodiments

Reference will now be made in detail to certain embodiments of the invention. While the invention will be described in conjunction with the embodiments, it will be understood that the intention is not to limit the invention to those embodiments. On the contrary, the invention is intended to cover all alternatives, modifications, and equivalents, which may be included within the scope of the present invention as defined by the claims.

Further aspects of the present invention and further embodiments of the aspects described in the preceding paragraphs will become apparent from the following description, given by way of example.

All of the patents and publications referred to herein are incorporated by reference in their entirety.

For purposes of interpreting this specification, terms used in the singular will also include the plural and vice versa.

One skilled in the art will recognize many methods and materials similar or equivalent to those described herein, which could be used in the practice of the present invention. The present invention is in no way limited to the methods and materials described.

The inventors of the present invention have developed new sugar. The sugars of the invention have two key advantages. They provide for the first time a very low glycaemic sugar and also provide a low glycaemic sugar having improved nutritional content, in particular micronutrient content such as polyphenols. The sugar remains largely sucrose but due to controlled levels of reducing sugars (in particular glucose) and the presence of an effective amount of polyphenols the sugar is not simply low glycaemic (ie a Gl of 55 or less) but can be very low glycaemic with a Gl as low as 15. Low, medium and high glycaemic categories are well understood.

The term“brown sugar” refers to a food grade sugar of brown colour.

The terms “efficacious” or “effective amount” refer to an amount that is biologically effective. In this context, one example is an effective amount of polyphenols in the sugar particles to achieve a low glycaemic sugar. Another example, is an effective lowering of reducing sugar content to achieve minimal hygroscopicity.

The term“endogenous” refers to something originating from within an organism. In the context of the present invention, it refers to something originating from within sugar cane, for example, a phytochemical including monophenol or polyphenol and polysaccharide can be endogenous because the compound originated from within the sugar cane.

The term“entrain” or“entrained” refers to incorporating or drawing in. In relation to crystal formation the term refers to incorporating something into the crystal structure or drawing something into the crystal structure. More specifically, in the context of the present invention the term refers to incorporating polyphenols within the sucrose crystals.

The term“high glycaemic” refers to a food with a glucose based Gl of 70 or more.

The term“low glycaemic” refers to a food with a glucose based Gl of 55 or less.

The term“massecuite” refers to a dense suspension of sugar crystals in the mother liquor of sugar syrup. This is the suspension that remains after concentration of the sugar juice into a syrup by evaporation, crystallisation of the sugar and removal of molasses. The massecuite is the product that is washed in a centrifuge to prepare bulk sugar crystals.

The term“medium glycaemic” refers to a food with a glucose based Gl of 56 to

69.

The term“phytochemical” refers generally to biologically active compounds that occur naturally in plants.

The term“polyphenol” refers to chemical compounds that have more than one phenol group. There are many naturally occurring polyphenols and many are phytochemicals. Flavonoids are a class of polyphenols. Polyphenols including flavonoids naturally occur in sugar cane. In the context of the present invention the polyphenols that naturally occur in sugar cane are most relevant. Polyphenols in food are micronutrients that are of interest because of the role they are currently thought to have in prevention of degenerative diseases such as cancer, cardiovascular disease or diabetes.

The term“raw sugar” refers to a food grade sugar of light brown colour.

The term“reducing sugar” refers to any sugar that is capable of acting as a reducing agent. Generally, reducing sugars have a free aldehyde or free ketone group. Glucose, galactose, fructose, lactose and maltose are reducing sugars. Sucrose and trehalose are not reducing sugars.

The term“refined white sugar” refers to fully processed food grade white sugar that is essentially sucrose with minimal reducing sugar content and minimal phytochemicals such as polyphenols or flavonoids.

The term“sugar” refers to a solid, the majority of which is sucrose (ie the sucrose sugar could be 80%, 90%, 95%, 99% w/w sucrose). The sugar may contain one or more other low molecular weight sugars. The sugar may be crystalline or amorphous. The sugar may contain other ingredients such as polyphenols and various minerals. Common sucrose sugars are prepared from sugar cane or from sugar beet.

The term“very low glycaemic” refers to a food with a glucose-based Gl of less than half the upper limit of low Gl (ie the Gl is in the bottom half of the low Gl range).

The sugar particles of the present invention can be prepared to food grade quality by methods known to skilled person including using equipment that has covers to prevent external contamination of the sugar particles, for example by bird droppings, the use of magnets to remove iron shavings and other metals and other methods used to prepare food grade sugar.

Sugar particles of the present invention may optionally include additives or extracts such as added flavours, for example maple syrup flavour, colours or additives/extracts to produce additional health, taste, colour or nutritional benefits. Methods for including these additives are known to those skilled in the art.

Sugar particles of the invention may optionally be cocrystallised or agglomerated. Methods for performing these processed are known to those skilled in the art. Polyphenol content measurement

Polyphenol content can be measured in terms of its catechin equivalents or in terms of its gallic acid equivalents (GAE). Amounts in mg CE polyphenols/100 g can be converted to mg GAE polyphenols/100 g by multiplying by 0.81 ie 60 mg CE polyphenols/1 OOg is 49 mg GAE polyphenols/1 OOg.

Glycaemic response (GR)

GR refers to the changes in blood glucose after consuming a carbohydrate- containing food. Both the Gl of a food and the glycaemic load (GL) of an amount of a food are indicative of the glycaemic response expected when food is consumed.

Gl

The glycaemic index is a system for classifying carbohydrate-containing foods according to the relative change in blood glucose level in a person over two hours after consuming that a food with a certain amount of available carbohydrate (usually 50 g). The area under the two hour blood glucose response curve (AUC) is divided by the AUC of a glucose standard, where both the standard and the test food must contain an equal amount of available carbohydrate. An average Gl is usually calculated from data collected from 10 subjects. Prior to a test the person would typically have undergone a twelve hour fast. The glycaemic index provides a measure of how fast a food raises blood-glucose levels inside the body. Each carbohydrate containing food has a Gl. The amount of food consumed is not relevant to the Gl. A higher Gl means a food increases blood-glucose levels faster. The Gl scale is from 1 to 100. The most commonly used version of the scale is based on glucose. 100 on the glucose Gl scale is the increase in blood-glucose levels caused by consuming 50 grams of glucose. High Gl products have a Gl of 70 or more. Medium Gl products have a Gl of 55 to 69. Low Gl products have a Gl of 54 or less. These are foods that cause slow rises in blood-sugar.

Those skilled in the art understand how to conduct Gl testing, for example, using internationally recognised Gl methodology (see the Joint FAO/WHO Report), which has been validated by results obtained from small experimental studies and large multicentre research trials (see Wolever et al 2003). In vitro Gl testing is now also available, see Example 1.

GL

Glycaemic load is an estimate of how much an amount of a food will raise a person’s blood glucose level after consumption. Whereas glycaemic index is defined for each type of food, glycaemic load is calculated for an amount of a food. Glycaemic load estimates the impact of carbohydrate consumption by accounting for the glycaemic index (estimate of speed of effect on blood glucose) and the amount of carbohydrate that is consumed. High Gl foods can be low GL. For instance, watermelon has a high Gl, but a typical serving of watermelon does not contain much carbohydrate, so the glycaemic load of eating it is low.

One unit of glycaemic load approximates the effect of consuming one gram of glucose. The GL is calculated by multiplying the grams of available carbohydrate in the food by the food’s Gl and then dividing by 100. For one serving of a food, a GL greater than 20 is high, a GL of 11-19 is medium, and a GL of 10 or less is low.

ICUMSA

ICUMSA is a sugar colour grading system. Lower ICUMSA values represent less colour. ICUMSA is measured at 420 nm by a spectrophotometric instrument such as a Metrohm NIRS XDS spectrometer with sa ProFoss analysis system. Currently, sugars considered suitable for human consumption, including refined granulated sugar, crystal sugar, and consumable raw sugar (ie brown sugar), have ICUMSA scores of 45-800. Sugars with scores above 800 are currently used for cosmetics or other non-edible purposes, but require further processing to be fit for human consumption. Consequently, the food grade sugars of the invention with ICUMSA values of 500 to 5000 ICUMSA are unexpected.

The sugar particles of the present invention may optionally be prepared using the methods and systems described in Australian Provisional Patent Application No 2016902957 filed on 27 July 2016 with the title“Process for sugar production” or International Patent Publication number WO 2018/018089 with the same title. Measuring proportions of surface and entrained polyphenols in solid crystalline sugars of the invention

The proportion of polyphenols on the surface of a solid crystalline sugar and the proportion of polyphenols entrained within the sugar crystal can be measured by washing the sugar with cold (refrigerated) water for 15 to 30 seconds. This time frame has shown to be sufficient to remove the surface polyphenols on sugars with no entrained polyphenols. However, the skilled person will be able to adjust the method for sugars with think additive layers that need a longer wash to remove the surface polyphenols. The skilled person will also be able to determine when the wash needs to cease because a longer wash will result in dissolution of the sugar crystals into the water. After the wash, the wash water and sugar crystals are separated and the amounts of polyphenols in each quantified to determine the proportion of surface and entrained polyphenols.

The Gl, sucrose, polyphenol, glucose, fructose and moisture content of a sugar prepared from a controlled wash of sugar cane massecuite

There is a“sweet spot” in the extent to which sugar is refined where Gl remains low. Too much washing removed the majority of polyphenol content and increased the Gl. Too little washing resulted in a higher reducing sugar content, which is thought to overpower the Gl lowering effect of the polyphenols and increase the Gl of the sugar.

The low Gl sweet spot was demonstrated by graphing the results of the sugars in Table 3 below. This graph demonstrates that at least 22 mg CE polyphenols/100 g sucrose needs to be retained during sugar processing to produce a low Gl sugar. If additional polyphenols are present but reducing sugars are too high then Gl lowering effect is removed. Respraying molasses back onto refined white and less refined raw sugars to produce a brown sugar may therefore not be an effective strategy to reduce Gl. Table 1 provides data on several sugars prepared by a controlled wash of sugar cane massecuite. Table 1 - Example sugars

Figure 1 shows a graph of Gl v polyphenol content of these sugars. This figure shows sugars have low Gl at about 22-32 mg CE polyphenols/1 OOg carbohydrate.

Preparation of a sugar of the invention

A sugar according to the invention can be prepared from either sugar cane or sugar beet, from refined white sugar or a sugar prepared in accordance with Example 2 (ie a starting sugar also referred to as a“first sugar” in the summary of invention). Most starting sugars require the addition of further polyphenols to result in a sugar according to this invention. Beet sugar does not contain polyphenols and neither does refined white sugar contain more than trace amounts of polyphenols. However, polyphenols can be added to either to prepare a sugar according to the invention. Sugars prepared by controlled washing of sugar cane massecuite can be prepared with the desired polyphenol content directly but are expected to then contain too much reducing sugar for a low Gl and the reducing sugar content will also likely result in a sugar with unacceptable hygroscopicity. For example, if the starting sugar is prepared using the controlled washing method of Example 2 or as described in patent publication numbers WO 2018/018090 and/or WO 2018/018089 to produce a sugar of 20 to 45 mg CE polyphenols/100 g carbohydrate and suitable reducing sugar content, then the sugar still requires additional polyphenols.

The further polyphenols may be added to the sugar in a powdered or liquid form. One option is to spray the liquid or powdered polyphenols onto the sugar. The process for adding the polyphenol additive onto the sugar can be completed as described in Singaporean patent application no SG 10201806479U or international patent application number PCT/SG2019/050377. Any reducing sugars may be added with or separately to the polyphenols. Alternatively, the reducing sugars may be in the starting sugar.

It is preferred that the polyphenols added to the sugar are polyphenols that, even if not sourced from sugar cane, are present in sugar cane. The polyphenols can be sourced from sugar cane, for example, from a sugar processing waste stream and may be in the form of a sugar cane extract. In some embodiments, the additive is a liquid containing 1000 mg CE polyphenols/100 g carbohydrate and about 11% solids (for example sugars) in water. 0 to 20% sugar is preferred in the additive.

Where the sugar is prepared from sugar cane, the massecuite contains polyphenols. A proportion of the polyphenols in the massecuite are entrained within the sucrose crystals in the massecuite. Massecuite also contains a proportion of polyphenols that are not entrained in the sucrose crystals and the proportion of polyphenols not entrained in the sucrose crystals is generally significantly greater than the proportion of polyphenols entrained within the sucrose crystals. The exact proportions can vary considerably based on variations in the process used to prepare the massecuite and variations in the sugar cane from which the massecuite is prepared. As an example, the quantity of polyphenols not entrained within the sucrose crystals could be tens to hundreds of times more than the amount of polyphenols entrained within the sucrose crystals. Optionally, the polyphenols entrained in the sucrose crystals in the massecuite are retained during processing of the massecuite and remain in the sugar particles. Optionally, an amount of the polyphenols not entrained within the sucrose crystals is retained during processing of the massecuite and remains on the surface of the sugar particles. In other words, a proportion of the polyphenols in the sugar particles can be endogenous to the sugar cane from which the sugar particles are prepared. The endogenous polyphenols may be separated from and then reintroduced to the sugar particles but remain with the bulk sucrose from which the sugar particles are seeded throughout processing and remain with the sugar particles through the washing process that follows seeding. Alternatively, the polyphenols are retained during processing of the massecuite and remain in the sugar composition because washing of the massecuite was ceased before removal of all of the polyphenols. A consequence of this process is that polyphenols entrained within the sucrose crystals remain within the sucrose crystals from the formation of those crystals and continue to remain within the sucrose crystals within the finished product. Optionally, the polyphenols remain in the sugar particles because washing of the massecuite was ceased before removal of all the polyphenols from the sugar particles (ie washing was ceased before the sugar particles became white). In some embodiments, washing of sugar cane massecuite is ceased when the sugar particles have been washed to contain suitable levels of reducing sugars (ie 0 to 1% w/w). The polyphenol content is then determined and, if needed, additional polyphenols added to achieve the desired about 46 mg CE polyphenols/100 g carbohydrate to about 100 mg CE polyphenols/100 g carbohydrate.

Alternatively, sugar cane can be refined until there is minimal polyphenol or reducing sugar content and the polyphenol content added to the sugar, for example, by a respraying process.

Alternatively, the sugar can be prepared from beet sugar. In this embodiment, the beet sugar is processed to ensure suitable reducing sugar levels and suitable polyphenol content added (as polyphenols are not endogenous to beet sugar).

References

Australian provisional patent application number 2016902957.

International patent publication numbers WO 2018/018090 and WO 2018/018089.

International patent application number PCT/SG2019/050377.

Jaffee, W.R., Sugar Tech (2012) 14:87-94

Joint FAO/WHO Report. Carbohydrates in Human Nutrition. FAO Food and Nutrition. Paper 66. Rome: FAO, 1998.

Kim, Dae-Ok, et al, Antioxidant capacity of phenolic phytochemicals from various cultivars of plums Food Chemistry (2003) 81 , 321-26.

Singapore patent application number SG 10201806479U.

Wolever TMS et al. Determination of the glycemic index values of foods: an interlaboratory study. European Journal of Clinical Nutrition (2003) 57:475-482.

A copy of each of these is incorporated into this specification by reference. Examples

Example 1 - Effect of polyphenols on Gl of sugar

The effect of polyphenol content on the Gl of sugar was studied. Traditional white sugar (ie essentially sucrose) was used as a control. Sugars with varied quantities of polyphenols were prepared by adding various amounts of polyphenol content to traditional white sugar.

Table 2 shows the results of testing of an in vitro Glycemic Index Speed Test (GIST) on the sugars prepared. The method involved in vitro digestion and analysis using Bruker BBFO 400MHz NMR Spectroscopy. The testing was conducted by the Singapore Polytechnic Food Innovation & Resource Centre, who have demonstrated a strong correlation between the results of their in vitro method and traditional in vivo Gl testing. The results of the GIST testing is also graphed in Figure 3.

Table 2 - sugar polyphenol content v Gl

While the Gl of fructose is 19, the Gl of glucose is 100 out of 100. We therefore expect that the as glucose increases in less refined sugars the glycemic response also concurrently increases.

A second set of sugars were prepared in which reducing sugars (1 :1 glucose to fructose) were added to some of the white refined sugar plus polyphenol sugars. The Gl of these sugars was also tested using the GIST method and the results are in Table 3. Table 3 - Effect of polyphenol and reducing sugar content on Gl

The Gl of several samples from Table 3 are graphed in Figure 4. Example 2 - Preparation of sugar containing polyphenols via controlled washing of sugar cane massecuite

PCT/AU2017/050782 (published as international patent publication WO 2018/018090) describes the preparation of less refined or raw sugar by controlling the washing of sugar cane massecuite. The process described allowed for the preparation of low glycaemic sugar (eg 22-32 mg CE polyphenols/100 g carbohydrate) but also medium glycaemic sugar with eg 15-19 mg CE polyphenols/100 g carbohydrate or medium to high Gl sugar with 60-70 mg CE polyphenols/100 g carbohydrate. Sugars prepared according to this example may have their polyphenol content supplemented by addition of an additive (as was done for the white sugar in Example 1) to prepare a sugar according to this invention.

For example, ten massecuite samples were prepared at two different sugar mills designated “Mill 1” and “Mill 2”. The polyphenol content of each sample was determined. The massecuite samples were washed until they were the depth of colour that is associated with the desired polyphenol content (ie roughly 500 to 2000 ICUMSA) and the polyphenol content measured. The results are in Table 4 below. The skilled person will understand that if the polyphenol content remains too high after the wash, a second wash is possible. The results for each sample are below. It is usual for some sugars prepared at a sugar mill to not meet specifications for various reasons.

Table 4 - Example sugars

The sugars above with 45 mg CE polyphenols/100 g carbohydrate or less prepared by a controlled wash could have additional polyphenol content added to prepare a sugar according to this invention. A sugar prepared by a controlled wash but having more than 45 mg CE polyphenols/100 g carbohydrate and a medium to high Gl could also be converted to a sugar according to the present invention by the addition of further polyphenols and/or the removal of glucose.

Example 3 - Analysis of polyphenol content in sugar, for example, prepared according Example 2

40 g of sugar sample was accurately weighed into a 100 ml volumetric flask. Approximately 40 ml of distilled water was added and the flask agitated until the sugar was fully dissolved after which the solution was made up to final volume with distilled water. The polyphenol analysis was based on the Folin-Ciocalteu method (Singleton 1965) and was adapted from the work of Kim et al (2003). In brief, a 50 pl_ aliquot of appropriately diluted raw sugar solution was added to a test tube followed by 650 mI_ pf distilled water. A 50 mI_ aliquot of Folin-Ciocalteu reagent was added to the mixture and shaken. After 5 minutes, 500 mI_ of 7% Na2CC>3 solution was added with mixing. The absorbance at 750 nm was recorded after 90 minutes at room temperature. A standard curve was constructed using standard solutions of catechin (0-250 mg/L). Sample results were expressed as milligrams of catechin equivalent (CE) per 100 g raw sugar. The absorbance of each sample sugar was determined and the quantity of polyphenols in that sugar determined from the standard curve.

Where the sugar is a less refined sugar prepared by a limited wash, an alternative method for analysis of the polyphenol content is to measure the amount of tricin in a sample using near-infra red spectroscopy (NIR). In these circumstances, the amount of tricin is proportional to the total polyphenols. Further information on this method is available in Australian Provisional Patent Application No 2016902957 filed on 27 July 2016 with the title “Process for sugar production” or international patent publication number WO 2018/018089.

Example 4 - analysis of the reducing sugar content in sugar, for example, prepared according to Example 2

There are several qualitative tests that can be used to determine reducing sugar content in a sugar product. Copper (II) ions in either aqueous sodium citrate or in aqueous sodium tartrate can be reacted with the sugar. The reducing sugars convert the copper(ll) to copper(l), which forms a copper(l) oxide precipitate that can be quantified.

An alternative is to react 3,5-dinitrosalicylic acid with the sugar. The reducing sugars will react with this reagent to form 3-amino-5-nitrosalicylic acid. The quantity of 3-amino-5-nitrosalicylic acid can be measured with spectrophotometry and the results used to quantify the amount of reducing sugar present in the sugar product.

Example 5 - Histopathological study of a low Gl sugar on mice

Histopathogical analysis of mice fed a carbohydrate-based high-polyphenol diet was performed at Monash University in Melbourne, Australia. Three cohorts of 7 weeks old male C57BL/6J mice were analysed. Each cohort was divided was divided into two groups of four mice, wherein one group was a control fed on diet SF06-020 (Specialty Feeds, Western Australia), which is SF00-219 modified to contain no cholesterol, and the other group was fed on diet SF06-020 + 60 mg CE polyphenols/100 g carbohydrate.

The SF06-020 was 34.129% w/w sucrose, 19.5% w/w acid casein, 21.0 % clarified butter. 5.0% w/w cellulose, 15.6% wheat starch and various vitamins and minerals.

Weeks 0-2 were baseline weeks, whereby all mice were placed onto the control diet (SF06-020). After 2 weeks, mice in each cohort were split into groups, wherein the control group remained on diet SF06-020 and the other group switched to diet SF06- 020 + 60 mg CE polyphenols/100 g carbohydrate.

The mice consumed more of the SF06-020 + 60 mg CE polyphenols/100 g carbohydrate diet than the control diet at 4 and 11 weeks, indicating that the quantity of polyphenols is palatable.

After 14 weeks the animals were sacrificed and histopathological analysis was performed. The SF06-020 + 60 mg CE polyphenols/100 g carbohydrate diet did not result in a decrease in bone mineral density for the group of mice on this diet. This is in contrast to other prior art carbohydrate-based high-polyphenol foodstuffs.