D(+)-Sucrose for analysis, ACS

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Synonyms: Sugar, Saccharose, α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside, β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside, β-(2S,3S,4S,5R)-fructofuranosyl-α-(1R,2R,3S,4S,5R)-glucopyranoside, α-(1R,2R,3S,4S,5R)-glucopyranosyl-β-(2S,3S,4S,5R)-fructofuranoside, Dodecacarbon monodecahydrate, ((2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxapent-2-yl]oxy-6-(hydroxymethyl)oxahexane-3,4,5-triol)

Sucrose or saccarose is a sugar with a sweet taste. It is extracted from certain plants, mainly sugar cane and sugar beet, and is widely used in human nutrition. It is a diholoside composed of glucose and fructose, whose normalized name is α-D-glucopyranosyl-(1↔2)-β-D-fructofuranoside, usually abbreviated as Glc-Fru. In English, it is referred to as sucrose, hence the abbreviation Suc for this compound sometimes encountered in the literature. - Carbohydrates, especially sucrose, used to be called carbohydrates because of an old experiment on the dehydrogenation of white sugar with concentrated sulfuric acid, in which sucrose with the molecular formula C12H22O11 was decomposed into water H2O and carbon black. From this it had been erroneously deduced that the formula for sucrose could be written (H2O)11C12, which would correspond to a carbohydrate. The term was made obsolete by the work of Walter Norman Haworth, who established the structure of carbohydrates in the early 20th century, and has since fallen out of use. In the English-speaking world, however, the term is still in common use. - Properties - Structure - The sucrose molecule is a diholoside consisting of a glucose residue and a fructose residue joined by an α(1↔2)β osidic bond. Its molecular formula is C12H22O11 and its molar mass is 342.3 g mol-1. Unlike most other diholosides, sucrose is formed by linking two oses at their reducing ends, which makes it a non-reducing sugar. In addition, only the α-anomer of glucopyranose and the β-anomer of fructofuranose form sucrose. - Sucrose crystallizes in the monoclinic crystal system according to space group P21 with crystal parameters a = 1.086 31 nm, b = 0.870 44 nm, c = 0.776 24 nm and β = 102.938° - The purity of sucrose is measured polarimetrically. More specifically, the rotation of the plane of polarization of polarized light passing through an aqueous sugar solution is measured. The specific rotation (en) at 20 °C, measured using the sodium D-line at 589 nm, is +66.47°. Commercial sucrose is controlled in this way. It does not deteriorate under normal conditions. - Sucrose has five natural isomers that differ in the position of the osidic bond: Trehalulose ⇒ glucose α(1→1) fructose ; Turanose ⇒ glucose α(1→3) fructose (reducing diholoside) ; Maltulose ⇒ glucose α(1→4) fructose ; Leucrose ⇒ glucose α(1→5) fructose (reducing diholoside) ; isomaltulose (palatinose) ⇒ glucose α(1→6) fructose (reducing diholoside). - Reactions involving sucrose-Various chemical transformations involving sucrose as a reactant are conceivable: -Thermal decomposition-The thermal decomposition of sucrose can be represented as a two-step reaction: -first, dehydration (by sulfuric acid H2SO4), producing water and soot: - C12H22O11 → 12 C + 11 H2O ; -and then oxidation (with oxygen from the air) of carbon to carbon dioxide : - 12 C + 12 O2 → 12 CO2. - Caramelization - sucrose does not melt when heated, but decomposes to caramel at about 186 °C. - Combustion - Sucrose burns in an exothermic reaction to form water and carbon dioxide, as all carbohydrates do. - With chloric acid - With chloric acid HClO3, sucrose releases water, carbon dioxide, and hydrogen chloride (HCl) : - 8 HClO3 + C12H22O11 → 11 H2O + 12 CO2 + 8 HCl. - Chemical properties - Sucrose is a non-reducing sugar , the hemiacetal carbon of glucose and the hemiacetal carbon of fructose are involved in the osideic bond. It is not hygroscopic and cannot undergo mutarotation. - Hydrolysis - Hydrolysis of sucrose causes the osidic bond to be cleaved, releasing glucose and fructose in equimolar amounts. However, this reaction is so slow that an aqueous sucrose solution can remain practically stable for years. In contrast, it proceeds much faster in the presence of a saccharase (sucrose isomaltase, invertase, sucrose alpha-glucosidase) or an acid such as potassium bitartrate HOOC-CHOH-CHOH-COOK or lemon juice, which are weak acids. The same happens in gastric juice, which participates in digestion by hydrolyzing carbohydrates such as sucrose. - The action of invertase on sucrose produces invert sugar, which consists of equal amounts of glucose and fructose. - Biosynthesis of sucrose - The biosynthesis of sucrose is carried out by sucrose phosphate synthase from UDP-glucose and fructose-6-phosphate. The energy required for this reaction comes from the cleavage of UDP. Sucrose is produced by plants and cyanobacteria, but not by other living organisms. It occurs naturally, along with fructose, in many plants consumed in the human diet. It is the main carbohydrate of many fruits such as pineapples and apricots; other fruits such as pears and grapes have fructose as their main carbohydrate. - The complete synthesis of sucrose was achieved by the Canadian chemist Raymond Lemieux in 1953. - Physical properties - Sucrose caramelizes at 160 °C. - Sucrose is highly soluble in water. The solubility of sucrose in non-aqueous solvents is generally lower. In addition, sucrose is not soluble in nonpolar solvents. High values are obtained with condensed ammonia (72%), dimethyl sulfoxide (42%) and methylamine (> 25%). Lower values are obtained with liquid sulfur dioxide, formic and acetic acids, dimethylformamide, pyridine (6%), propylene glycol, glycerol (7%), methanol, ethanol, acetone and dioxane. - The sugar content is indicated by the Brix degree (which corresponds to the mass percentage at 20 °C). The concentration of an aqueous solution can be determined by measuring the density with a mustimeter or the refractive index with a refractometer. - Sweetening Properties - The sweetening power of sucrose serves as a reference value in the sweetener scale, i.e., it is conventionally taken as 1. The average detection limit of sucrose is 0.017 mol l-1 (5.82 g/liter). - Sources of sucrose - In nature, sucrose is found in a wide variety of plants, especially in their roots, fruits, and nectar, where it is used to store energy from photosynthesis. Many mammals, birds, insects and bacteria feed on the sucrose in plants, some even as their main food. Bees play a special role in human nutrition in this regard, as they produce honey from nectar, which is consumed in all parts of the world. However, the sugars in honey are predominantly glucose and fructose, with only traces of sucrose. As fruits ripen, the sucrose content usually increases very rapidly, but there are also fruits that contain almost no sucrose. Examples include grapes, cherries, blueberries, blackberries, figs, pomegranates, tomatoes, avocados, lemons and limes. - Uses in the Food Industry - Sugar as an Important Food Ingredient - Sucrose is one of the most commonly used ingredients in the food industry. It forms the basis for certain industries such as confectionery, bakery, jam and beverage. - In the pharmaceutical industry, it is used as an excipient. - Physical Chemistry - Sucrose is highly soluble in water, with solubility increasing with temperature. It is relatively stable, but can ferment (a generally undesirable development except in alcoholic beverages) or hydrolyze into glucose and fructose (in confectionery language: invert), although this phenomenon can be controlled. - When used in the beverage industry, sucrose can invert by itself during heat treatment. In addition, since invert sugar is more soluble than sucrose, it can act as a water binder in its presence and prevent sucrose from crystallizing. - Sucrose reduces the water activity of products that contain a lot of sucrose, allowing them to be preserved. - It can also be used as a texture aid due to its agglomerating properties. - Grain size - Different crystal sizes according to the needs of the industry : granulated sugar; sugar couleur; powdered sugar; granulated sugar. - Use in fermentation - Sucrose is one of the most classic fermentation substrates. Many microorganisms can ferment it, including the highly evolved Saccharomyces cerevisiae. - Uses in Agriculture - Sucrose is used in agriculture. Spraying very small doses of soluble sugars in orchards has an insect repellent effect by altering the perception of the plant by pests.

FAQs

What is sucrose?

D(+)-sucrose or common sugar is a disaccharide formed by glucose and fructose, two simple sugars or monosaccharides. The bond that binds the two monosaccharides is O-glycosidic type, this bond is dicarbonyl since it is the two reducing carbons of both monosaccharides that form the alpha(1-2) bond of alpha-D-glucose and beta-D-fructose. It is commonly known as sugar, sucrose or saccharose, or by the following chemical designations: beta-D-fructofuranosyl-alpha-D-glucopyranoside (IUPAC name), alpha-D-glucopyranosyl-beta-D-fructofuranoside, α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside; β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside; β-(2S,3S,4S,4S,5R)-fructofuranosyl-α-(1R,2R,3S,4S,5R)-glucopyranoside; α-(1R,2R,3S,4S,5R)-glucopyranosyl-β-(2S,3S,4S,5R)-fructofuranoside; ((2R,3R,4S,5S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxapent-2-yl]oxy-6-(hydroxymethyl)oxahexane-3,4,5-triol). The molecular formula of D(+)-sucrose is C12H22O11. It is obtained mainly from sugar cane and sugar beet. Sucrose has no reducing properties because it does not contain any free anomeric carbon atoms, the anomeric carbons are bonded together (both OH groups of the carbonyl carbons participate in the O-glycosidic bond), i.e. the glycosidic bond of sucrose is formed between the reducing ends of glucose and fructose, and not between the reducing end of one and the non-reducing end of the other. Therefore, having no reducing character, sucrose is negative in the Fehling's test. Sucrose is optically active. Optical activity is the property of a substance to rotate the plane of polarized light. Sucrose rotates the plane of polarization clockwise, so it is called a dextrorotatory (+) sugar. D-L nomenclature provides a quick abbreviation for enantiomers. These compounds have two stereoisomeric forms and are designated by the letters D- and L- in front of the compound name, but should not be confused with the nomenclature relating to the classification of enantiomers into dextrorotatory (+) and levorotatory (-) forms, which refers to optical activity. Sucrose, apart from being the main natural sweetener in the human diet, is the sugar most used by the pharmaceutical industry for the production of syrups, chewable tablets, lozenges, gums, etc. Syrups contain sucrose in a high proportion, not only to achieve sweetness and viscosity, but also to increase their stability against microorganisms due to the lack of water availability. The high concentrations of sugar mean that the high osmotic pressure of the syrup prevents bacterial growth. Sucrose is also an excipient in vaccines. Since vaccines are biological preparations, they can be unstable once created. This instability can reduce the safety and efficacy of the biological product; vaccines can be sensitive to heat, light or changes in the environment. Sucrose maintains the efficacy of vaccines by preventing the molecules from losing their shape in the manufacturing process, storage, distribution and finally when administered to patients. In the food industry, sugars in general, act as sweeteners, flavor enhancers, antioxidants and preservatives. Chemical reactions of sugars include Maillard reactions or the formation of brown compounds and caramelization. Sucrose, in particular, acts as a stabilizer due to its natural wetting properties. It is used as a multifunctional product as it not only sweetens foods, but also helps foods, especially bakery and confectionery products, to stay fresh and retain their moisture; it promotes fermentation in bread and other yeast-containing products, improves the flavor and texture of foods in general, and is also used as a preservative and sweetener in juices, carbonated beverages, soft drinks and alcoholic beverages. Like any other solute, the addition of sugar to a mixture modifies its boiling and freezing points. For example, in the manufacture of ice cream, sugars reduce the freezing point, preventing the water inside the ice cream from turning into ice, thus achieving a smooth texture that is suitable for working despite low temperatures. On the other hand, for the manufacture of candies, the increase of the boiling point is the determining factor of the texture of the final product. In general, higher temperatures (higher sugar concentration) produce harder and stiffer candies, while lower temperatures produce softer candies. The final texture of a candy will depend on the sugar concentration, which in turn depends on the boiling point.

Why is sucrose a non-reducing sugar?

Sucrose is a non-reducing sugar because it does not contain any free anomeric carbon atoms, the anomeric carbons are bonded together (both OH groups of the carbonyl carbons participate in the O-glycosidic linkage), i.e., the glycosidic bond of sucrose is formed between the reducing ends of glucose and fructose, not between the reducing end of one and the non-reducing end of the other. Being a non reducing sugar, sucrose is negative in the Fehling's test. Reducing sugars occurs in a disaccharide when one of the constituent monosaccharides has its anomeric (or carbonyl) carbon free, that is, if this carbon does not form part of the O-glycosidic bond. In other words, if the O-glycosidic bond is monocarbonyl, the resulting disaccharide will be reducing (lactose, maltose), whereas if the O-glycosidic bond is dicarbonyl, the resulting disaccharide will be non-reducing (sucrose, trehalose). Fehling's reagent (discovered by the German chemist Hermann von Fehling) is used for the detection of reducing substances, particularly reducing sugars. It is based on the reducing ability of the carbonyl group of an aldehyde which becomes acidic by reducing the copper (II) cupric salt in an alkaline medium to copper (I) oxide. This forms a red precipitate. An important aspect of this reaction is that the aldehyde form can be easily detected, even if it exists in very small amounts. If a sugar reduces Fehling's reagent to red copper(I) oxide, it is said to be a reducing sugar. Fehling (blue) + non-reducing sugar = color blue; Fehling (blue) + reducing sugar = color brick red

What is the Fehling's test for?

Fehling's test (discovered by the German chemist Hermann von Fehling) is used for the detection of reducing substances, particularly reducing sugars. It is based on the reducing ability of the carbonyl group of an aldehyde which becomes acidic by reducing the copper (II) cupric salt in an alkaline medium to copper (I) oxide. This forms a red precipitate. An important aspect of this reaction is that the aldehyde form can be easily detected, even if it exists in very small amounts. If a sugar reduces Fehling's reagent to red copper(I) oxide, it is said to be a reducing sugar. Fehling (blue) + non-reducing sugar = color blue ;Fehling (blue) + reducing sugar = color brick red

What are the applications of sucrose?

Sucrose, apart from being the main natural sweetener in the human diet, is the sugar most used by the pharmaceutical industry for the production of syrups, chewable tablets, lozenges, gums, etc. Syrups contain sucrose in a high proportion, not only to achieve sweetness and viscosity, but also to increase their stability against microorganisms due to the lack of water availability. The high concentrations of sugar mean that the high osmotic pressure of the syrup prevents bacterial growth. Sucrose is also an excipient in vaccines. Since vaccines are biological preparations, they can be unstable once created. This instability can reduce the safety and efficacy of the biological product; vaccines can be sensitive to heat, light or changes in the environment. Sucrose maintains the efficacy of vaccines by preventing the molecules from losing their shape in the manufacturing process, storage, distribution and finally when administered to patients. In the food industry, sugars in general, act as sweeteners, flavor enhancers, antioxidants and preservatives. Chemical reactions of sugars include Maillard reactions or the formation of brown compounds and caramelization. Sucrose, in particular, acts as a stabilizer due to its natural wetting properties. It is used as a multifunctional product as it not only sweetens foods, but also helps foods, especially bakery and confectionery products, to stay fresh and retain their moisture; it promotes fermentation in bread and other yeast-containing products, improves the flavor and texture of foods in general, and is also used as a preservative and sweetener in juices, carbonated beverages, soft drinks and alcoholic beverages. Like any other solute, the addition of sugar to a mixture modifies its boiling and freezing points. For example, in the manufacture of ice cream, sugars reduce the freezing point, preventing the water inside the ice cream from turning into ice, thus achieving a smooth texture that is suitable for working despite low temperatures. On the other hand, for the manufacture of candies, the increase of the boiling point is the determining factor of the texture of the final product. In general, higher temperatures (higher sugar concentration) produce harder and stiffer candies, while lower temperatures produce softer candies. The final texture of a candy will depend on the sugar concentration, which in turn depends on the boiling point."

What is D(+)-sucrose used for?

D(+)-sucrose, or simply sucrose, is the common sugar. Sucrose, apart from being the main natural sweetener in the human diet, is the sugar most used by the pharmaceutical industry for the production of syrups, chewable tablets, lozenges, gums, etc. Syrups contain sucrose in a high proportion, not only to achieve sweetness and viscosity, but also to increase their stability against microorganisms due to the lack of water availability. The high concentrations of sugar mean that the high osmotic pressure of the syrup prevents bacterial growth. Sucrose is also an excipient in vaccines. Since vaccines are biological preparations, they can be unstable once created. This instability can reduce the safety and efficacy of the biological product; vaccines can be sensitive to heat, light or changes in the environment. Sucrose maintains the efficacy of vaccines by preventing the molecules from losing their shape in the manufacturing process, storage, distribution and finally when administered to patients.