Sucrose

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  Advanced Nutrition

  Macronutrients

  • (Author)
  • 2014(Publication Date)
  • Library Press

    (Publisher)

  ________________________ WORLD TECHNOLOGIES ________________________ Chapter- 13 Sucrose Sucrose Other names Sugar; Saccharose; β -D -fructofuranosyl-(2→1) -α -D -glucopyranoside; β -(2 S ,3 S ,4 S ,5 R )-fructofuranosyl-α -(1 R ,2 R ,3 S ,4 S ,5 R )-glucopyranoside Identifiers CAS number 57-50-1 PubChem 5988 ChemSpider 5768 EC-number 200-334-9 RTECS number WN6500000 Properties Molecular formula C 12 H 22 O 11 Molar mass 342.30 g/mol Appearance white solid Density 1.587 g/cm 3 , solid Melting point 186 °C decomp. Solubility in water 2000 g/L (25 °C) log P −3.76 Structure Crystal structure Monoclinic ________________________ WORLD TECHNOLOGIES ________________________ Space group P2 1 Hazards MSDS ICSC 1507 EU Index not listed Related compounds Related compounds Lactose Maltose Sucrose is the organic compound commonly known as table sugar and sometimes called saccharose . A white, odorless, crystalline powder with a sweet taste, it is best known for its role in human nutrition. The molecule is a disaccharide derived from glucose and fructose with the molecular formula C 12 H 22 O 11 . About 150,000,000 tonnes (metric tons) are produced annually. Physical and chemical properties Sucrose is a molecule with five stereocenters and many sites that are reactive or can be reactive. The molecule exists as a single isomer. Structural β -D -fructofuranosyl-(2→1) -α -D -glucopyranoside In Sucrose,P the I component T glucose O and fructose are linked via an ether bond between C1 on the glucosyl subunit and C2 on the fructosyl unit. The bond is called a glycosidic linkage. Glucose exists predominantly as two isomeric pyranoses (α and β), but only one of these forms the links to the fructose. Fructose itself exists as a mixture of furanoses, each of which has α and β isomers, but again only one particular isomer links to the glucosyl unit.

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  Dietary Sugars

  Chemistry, Analysis, Function and Effects

  • Victor R Preedy(Author)
  • 2012(Publication Date)
  • Royal Society of Chemistry

    (Publisher)

  In this context, it is important to note the different roles for Sucrose in living beings. For example, Sucrose is fundamental to the life cycle of the 145 Sucrose Chemistry microorganism Streptococcus mutans , which is uniquely responsible for tooth decay. 9.7 Conclusions The ingestion of Sucrose and the public health problems associated with dia-betes, obesity and other chronic health difficulties have motivated studies focused on this highly relevant carbohydrate.Nevertheless, Sucrose is still an extraordinarily nutritious constituent of a great number of foods. Thus, research focused on Sucrose chemistry is interesting and necessary for the improvement of the general health condition of the worldwide population. In addition, the future of Sucrose applications economically affects a great number of families worldwide and requires a multidisciplinary and interdisciplinary study with regards to the substitution of this important compound. The questions about the possible risks of the systemic use of ‘‘sugar substitutes’’ as a main sweetening product remain a concern of specialists and professionals in this area of study. Therefore, studies focused on Sucrose chemistry will continue to be auspicious research for several more years. Summary Points Sucrose is the most abundant organic molecule produced at the industrial scale from renewable sources. Sucrose is a disaccharide formed by glycosidic ligation between the two monosaccharides glucose and fructose. Glucose is a polyhydroxy aldehyde, that is, a monosaccharide composed of six carbons, and fructose is a polyhydroxy ketose, a monosaccharide composed of six carbons. Inverted sugar has an important role in the food industry. This compound consists of a mixture of glucose and fructose and is obtained by splitting the glycosidic bond of Sucrose.

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  Handbook of Food and Beverage Stability

  • Bozzano G Luisa(Author)
  • 2012(Publication Date)
  • Academic Press

    (Publisher)

  7. Candy and Sugar Confectionery 425 syrup (which contain maltose and polymers of glucose). Sucrose is a disaccharide composed of a glucose unit and a fructose unit linked together. Sucrose can be hydrolyzed to a mixture of the two monosaccharides, and this mixture is invert sugar. Glucose and fructose are often called dextrose and lévulose, respectively. The different meanings for dif-ferent ingredients, especially the use of the name glucose for both a sugar and a syrup, obviously are a source of con-fusion. In this chapter, the individual chemical components will be called Sucrose, glucose, fructose and so on. The term sugar will refer to all of them collectively, although often Sucrose will be the major sugar involved. The term sweetener includes not only the sugars and their commercial sources, but also sugar alcohols such as sorbitol, mannitol, and xylitol, and the artificial sweeteners. Except where noted, metric units of measurement are used. Particularly note that temperatures are given in degrees Celcius. Conversion to the American system can be made by the appropriate conversion factors, or in many cases by re-ferring to the works cited. Much of the information presented here was originally obtained using American units, and later converted to metric in the references or for this chapter. Water activities are given in decimal form, and can be con-verted to percentage equilibrium relative humidity by multi-plying by 100. When concentrations are expressed as percentages, these are percentages by weight. I wish to point out two items that are not discussed herein, so that readers do not think they have been overlooked. One is humectance, a term I have avoided because it means dif-ferent things to different people and in different applica-tions. Humectance is associated with water absorbance or retention, so it can be replaced in any situation by discus-sion of water activity and relative humidity.

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  How Baking Works

  Exploring the Fundamentals of Baking Science

  • Paula I. Figoni(Author)
  • 2010(Publication Date)
  • Wiley

    (Publisher)

  Maltose (malt sugar) is one example of a disaccharide. It consists of two glucose molecules. Maltose is commonly found in glucose corn syrup and malt syrup. Lactose (milk sugar) is a disaccharide found only in dairy products. Sucrose, the most common sugar in the bakeshop, is also a Figure 8.3 Typical representation of the skeletal structures of the disaccharides maltose and Sucrose Sucrose Fructose SUGAR AND OTHER SWEETENERS 165 Sugar crystals are highly ordered arrangements of sugar molecules bonded together. They form because sugar molecules of the same type are attracted to one another. Crystal growth can be desirable, as when making rock candy, or it can be unwanted, as when making nut brittle, caramel, or pulled sugar. Smooth and creamy fondants and icings require the smallest of crystals for the best appearance and mouthfeel. For the most part, sugar crystals are pure. This means, for example, that crystals of Sucrose consist entirely of Sucrose, even when they form from syrups that contain a mix of sugars. The mix just makes it more difficult for crystals to form, because it makes it difficult for mol- ecules of the same type to come together. Because they are pure, sugar crystals are naturally white in color and do not need to be chemically bleached. When crystals are off color, as they are in semirefined and brown sugars, it is because “impurities” are trapped between the crystals. disaccharide. It consists of one molecule of glucose bonded to fructose. In addition to monosaccharides and disaccharides, two other main classifications of carbohydrates are oli- gosaccharides and polysaccharides. Oligosaccharides are made up of a few (oligo) sugar units, usually three to ten, bonded into a chain. Oligosaccharides, which are called higher saccharides or sometimes dextrins by the sweetener industry, are present in many syrups used in the bakeshop. Figure 8.4 shows the skeletal structure of two higher saccharides.

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  Asymmetric Synthesis of Natural Products

  • Ari M. P. Koskinen(Author)
  • 2022(Publication Date)
  • Wiley

    (Publisher)

  4 Sugars New conceptual approaches to glycosylation and novel strategies for the construction of complex oligosaccharides and glycoconjugates are … welcome to meet the intrinsic structural diversity of carbohydrates. R.R. Schmidt, 2009 In the early nineteenth century, individual sugars were often named after their source, e.g. grape sugar (Traubenzucker) for glucose and cane sugar (Rohrzucker) for saccharose (the name Sucrose was coined much later). Cellulose (from French ‘cellule’ for cell and ending ‘-ose’ to refer to sugars) was isolated and its overall composition elucidated in 1838 by the French chemist Anselme Payen (1795–1878). Its chemical formula was confirmed to be the same as that of dextrin (starch) [1]. The term ‘carbohydrate’ (French ‘hydrate de carbone’) was applied originally to monosaccha- rides, in recognition of the fact that their empirical composition can be expressed as C n (H 2 O) n . Although misleading, the term persists in general use in a wider sense, including monosaccharides, oligosaccharides (oligomers with a few monosaccharides), and polysaccharides (glycans consisting of a large number of monosaccharide units), as well as sub- stances derived from monosaccharides by reduction, oxidation, or by replacement of one or more hydroxy group(s) by heteroatomic groups. We prefer the term ‘sugar,’ which is frequently applied to monosaccharides and lower oligosac- charides. Strictly speaking, cyclitols (Section 4.6) are generally not regarded as carbohydrates, but are sugars. In a common parlance, sugars are often associated with a sweet taste. If we compare the sweetness of sugars to that of Sucrose, the common sugar, which is a disaccharide formed of glucose and fructose, we observe that most of the sugars are only fairly sweet. Lactose, the milk sugar, a disaccharide of galactose and glucose, and maltose, the malt sugar, a disaccharide of two glucoses, are really not sweet at all (Table 4.1).

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  Understanding Baking

  The Art and Science of Baking

  • Joseph Amendola, Nicole Rees(Authors)
  • 2003(Publication Date)
  • Wiley

    (Publisher)

  C H A P T E R 3 S U GA R S A N D O T H E R S W E E T E N E R S T he word sugar can mean many different things. Often equated with Sucrose, or granulated white sugar, the word usually refers to common table sugar, a substance refined from sugarcane or beets. But as any baker knows, sugar comes from many plant sources and takes many forms. Honey, maple sugar, and corn syrup are all sugars. In this sense, the word sugar no longer refers only to granulated sugar; it de- fines a specific type of substance. Ultimately sugar is a chemical desig- nation for specific molecular structures. As dull as it sounds, the easiest way to understand the similarities and differences between honey and granulated sugar, as they apply to a pastry chef, is to start with chemistry. Nutritionally speaking, humans require six basic substances for survival. Water, carbohydrates, proteins, fats, vitamins, and minerals. Sugars, or saccharides, as they are called, are a subgroup of carbohydrates. When many sugar molecules are joined together in long chains, they are no longer technically a sugar— they are a starch. So sugars are the building blocks of more complex types of carbohydrates; many saccharides joined together are a polysac- charide, the prefix poly meaning “many.” The human body requires carbohydrates, but the process of diges- tion breaks carbohydrates (starchy foods like bread, pasta, and potatoes) down into the simplest form possible. Polysaccharides become saccha- rides. There are two major types of saccharides: monosaccharides and disaccharides. The prefix mono means “one,” so monosaccharides are the smallest elemental sugars. Di means “two”; it takes two mono- saccharides to form a disaccharide. In the body, all carbohydrates are 49 essentially broken down into glucose (also known as dextrose), the monosaccharide our cells use for fuel.

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  The Components of Life

  From Nucleic Acids to Carbohydrates

  • Britannica Educational Publishing, Kara Rogers(Authors)
  • 2010(Publication Date)
  • Britannica Educational Publishing

    (Publisher)

  Other naturally occurring deoxy sugars are hexoses, of which l-rhamnose (6-deoxy-l-mannose) and l-fucose (6-deoxy-l-galactose) are the most common. The latter, for example, is present in the carbohydrate portion of blood-group substances and in red-blood-cell membranes.

  DISACCHARIDES AND OLIGOSACCHARIDES

  Disaccharides are a specialized type of glycoside in which the anomeric hydroxyl group of one sugar has combined with the hydroxyl group of a second sugar with the elimination of the elements of water. Although an enormous number of disaccharide structures are possible, only a limited number are of commercial or biological significance.

  SUCROSE AND TREHALOSE

  Sucrose, or common table sugar, has a world production amounting to well over 10,000,000 tons annually. The unusual type of linkage between the two anomeric hydroxyl groups of glucose and fructose means that neither a free aldehyde group (on the glucose moiety) nor a free keto group (on the fructose moiety) is available to react unless the linkage between the monosaccharides is destroyed. For this reason, Sucrose is known as a nonreducing sugar. Sucrose solutions do not exhibit mutarotation, which involves formation of an asymmetrical centre at the aldehyde or keto group. If the linkage between the monosaccharides composing Sucrose is broken, the optical rotation value of Sucrose changes from positive to negative. The new value reflects the composite rotation values for d–glucose, which is dextrorotatory (+52°), and d–fructose, which is levorotatory (−92°). The change in the sign of optical rotation from positive to negative is the reason Sucrose is sometimes called invert sugar.

  The commercial preparation of Sucrose takes advantage of the alkaline stability of the sugar, and a variety of impurities are removed from crude sugarcane extracts by treatment with alkali. After this step, syrup preparations are crystallized to form table sugar. Successive “crops” of Sucrose crystals are “harvested,” and the later ones are known as brown sugar. The residual syrupy material is called either cane final molasses or blackstrap molasses. Both are used in the preparation of antibiotics, as sweetening agents, and in the production of alcohol by yeast fermentation.

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  Carbohydrate Chemistry for Food Scientists

  • James N. BeMiller(Author)
  • 2018(Publication Date)
  • Woodhead Publishing and AACC International Press

    (Publisher)

  Sucrose (commonly called sugar) are found in only a few plant tissues. Early humans used fruits and honey as a source of sweetness. Many thousands of years passed before another source of sweetness was found. Sugarcane was first cultivated along the Ganges River in what is now the state of Bihar in India. Cultivation spread slowly, reaching China by about the 1st century B.C.E. Sugarcane growing spread to the Middle East and was brought to Europe by the Crusaders who, like Pliny the Elder, much earlier, called its juice “a kind of honey made from reeds.” For several centuries after Sucrose was first brought to Europe, it was a delicacy enjoyed only by the nobility. Not until Spanish and Portuguese travelers brought sugarcane to the Americas, where it was grown on large plantations, did the price come down to a level where the general public could afford it.

  The structure of Sucrose (Fig. 3.5 ), a disaccharide, is an exception to the general rule for structures of oligo- and polysaccharides. In Sucrose, the constituent glycosyl units (an α-D -glucopyranosyl unit and a β-D -fructofuranosyl unit) are linked head-to-head, that is, reducing end to reducing end (anomeric carbon atom to anomeric carbon atom) (Fig. 3.6 ), rather than the very much more common head-to-tail (anomeric carbon atom to a carbon atom containing an alcoholic hydroxyl group) type of linkage. Since both the aldehydic group of the D -glucosyl unit and the keto group of the D -fructosyl unit are covalently bound in a mutual glycosidic bond, Sucrose has no reducing end. Therefore, it is classified as a nonreducing sugar and does not react with Fehling solution or Tollens' reagent in tests for detection of aldehydes or ketones (Chapter 2 ).

  A majority of Sucrose molecules in solution have the structure illustrated below, where the primary hydroxyl group at C1 of the D -fructofuranosyl unit is hydrogen bonded to the C2 hydroxyl group of the D -glucopyranosyl moiety to the extent that it is much less reactive than the remaining primary hydroxyl groups. In crystalline Sucrose, there is an additional hydrogen bond between the primary hydroxyl group at C6′ and the ring oxygen atom of the D

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  Principles of Sugar Technology

  • Pieter Honig(Author)
  • 2013(Publication Date)
  • Elsevier

    (Publisher)

  W . C A R L S O N , / Bact. 5 8 ( 1 9 4 9 ) 1 3 5 . 50 M. S T A C E Y and G . S W I F T , / Chem. Soc. London ( 1 9 4 8 ) 1 5 5 5 . 51 Ε. I. H E H R E and D . M. H A M I L T O N , / Biol. Chem. 1 6 6 ( 1 9 4 6 ) 7 7 7 ; / . Bact. 5 5 ( 1 9 4 8 ) 1 9 7 ; S. A . B A R K E R , E . J . B O U R N E and M. S T A C E Y , / Chem. Soc. London ( 1 9 5 0 ) 2 8 8 4 . 52 S. A V I N E R I -S H A P I R O and S. H E S T R I N , Biochem. J. 3 9 ( 1 9 4 5 ) 1 6 7 ; W . G . F O R S Y T H and D . M. WEBLEY, Biochem. J. 4 4 ( 1 9 4 9 ) 4 5 5 . 53 A . T. C A M E R O N , The Taste Sense and the Relative Sweetness of Sugars and other Sweet Substances, Sugar Res. Found. Sei. Pap. Ser. No. 9 ( 1 9 4 7 ) . CHAPTER 2 PHYSICAL PROPERTIES OF Sucrose H. HIRSCHMÜLLER Director of the Institut für Zuckerindustrie, Berlin ( Germany) 1. Sucrose Molecule The molecular weight of Sucrose is 342.296. The calculation from grams of Sucrose to moles of Sucrose, and vice versa, is facilitated by the multiples in Table 1. TABLE 1 F O R C A L C U L A T I N G G R A M S O F S U C R O S E I N M O L E S O F S U C R O S E A N D V I C E V E R S A Grams of Moles of j Moles of Grams of Sucrose Sucrose j! Sucrose Sucrose I I 100 0.292 145 i, 1 342.296 200 0.584 290 2 684.592 300 0.876 435 :! 3 1026.89 400 1.168 58 :| 4 1369.18 500 1.460 72 5 1701.48 600 1.752 87 ! 6 2043.78 700 2.045 01 7 2396.07 800 2.337 16 8 2738.37 900 2.629 30 |i 9 3080.66 The normal entropy 1 {i.e. the entropy at 25° C and 760 mm pressure) of Sucrose is 86.1 CI (= 86.1 cal/° absolute) per mole. The enthalpy* of formation 1 {i.e. content of heat of C 1 2 H 2 2 0 l l c r y s t minus content of heat of 12 C g r a p h i t e , 11 H 2 g a s , and 5.5 0 2 g a s ) at 25° C and 760 mm pressure is —530.8 kcal per mole; accordingly the heat of formation {i.e. the heat delivered from this hypothetical synthesis) is 530.8 kcal per mole.

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  Economic Botany

  A Comprehensive Study

  • S. L. Kochhar(Author)
  • 2016(Publication Date)
  • Cambridge University Press

    (Publisher)

  The general formula is (C n H 2n-2 O n‒1 )x. Like disaccharides, they can be broken down into their constituent sugars by hydrolysis. Starch and cellulose (less frequently inulin) are the two most abundant polysaccharides in plants. Carbohydrates make up the bulk of the dry weight of plants. Although there are many kinds, sugars, starches and the celluloses predominate. Cellulose is insoluble in water and cannot be digested by man, but can be decomposed by microorganisms. Sugars It would be difficult to imagine our lives without sugars both as a source of energy and as a sweetening agent. However, all the great civilisations of the past lived without sugar. Neither the Bible, the Talmud nor the Koran contains references to sugar and sugarcane, although honey is mentioned in all of these religious works. Honey, undoubtedly, was the first sweetening material of our ancestors and in Chapter 4 142 Economic Botany order to have a steady supply at hand, man domesticated bees (apiculture). The ancient Greeks and Romans had no sugar. Sugar was a rare commodity in Europe until the Middle Ages and was used only by the aristocratic society. It was sold in ’apothecaries’ shops as a medicine. However, by the end of the fifteenth century, sugar had replaced honey as a sweetener and became a cheap and common food for all people in the nineteenth and twentieth centuries. Honey, although produced by bees, is essentially the nectar provided by a great number of flowering plants. Nectar consists mostly of Sucrose, along with small amounts of glucose and fructose, which after partial digestion by the bee are converted into honey that is stored in the hive or nest. Honey contains 75-78 per cent invert sugar, together with proteins, minerals and water. The chief components of invert sugars are ‘fructose (sometimes called levulose or fruit sugar) and glucose (dextrose or grape sugar), with very small amounts of Sucrose.

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