Sucrose 50563 225941484 2008-07-16T03:16:04Z Capefeather 1110061 fixed pic placement {{Chembox new | Name = Sucrose | ImageFile = Sucrose-inkscape.svg | ImageFile1 = Sucrose_molecule_3d_model.png | IUPACName = Sucrose<!-- e.g. Iron(II) chloride --> | OtherNames = Sugar, Saccharose | Section1 = {{Chembox Identifiers | SMILES = OC1C(OC(CO)C(O)C1O)<br>OC2(CO)OC(CO)C(O)C2O | CASNo = 57-50-1 | RTECS = WN6500000 }} | Section2 = {{Chembox Properties | Formula = C<sub>12</sub>H<sub>22</sub>O<sub>11</sub> | MolarMass = 342.29648 g/mol | Appearance = white solid | Density = 1.587 g/cm³, solid | Solubility = 211.5 g/100 ml (20 °C) | MeltingPt = 186&nbsp;°[[Celsius|C]] }} | Section7 = {{Chembox Hazards | MainHazards = Combustible | NFPA-H = 1 | NFPA-F = 1 | NFPA-R = | FlashPt = N/A | RPhrases = | SPhrases = }} | Section8 = {{Chembox Related | OtherAnions = }} }} <table class="toccolours" border="1" style="float:right; clear:right; margin: 0 0 1em 1em; border-collapse: collapse;"> <tr><th colspan=2>Solubility of Pure Sucrose</th></tr> <tr><th>Temperature(C)</th><th>g Sucrose/g Water</th></tr> <tr><td><center>50</center></td><td><center>2.59</center></td></tr> <tr><td><center>55</center></td><td><center>2.73</center></td></tr> <tr><td><center>60</center></td><td><center>2.89</center></td></tr> <tr><td><center>65</center></td><td><center>3.06</center></td></tr> <tr><td><center>70</center></td><td><center>3.25</center></td></tr> <tr><td><center>75</center></td><td><center>3.46</center></td></tr> <tr><td><center>80</center></td><td><center>3.69</center></td></tr> <tr><td><center>85</center></td><td><center>3.94</center></td></tr> <tr><td><center>90</center></td><td><center>4.20</center></td></tr> </table> '''Sucrose''' (common name: '''table sugar''', also called '''saccharose''') is a [[disaccharide]] of [[glucose]] and [[fructose]], with the [[molecular formula]] C<sub>12</sub>H<sub>22</sub>O<sub>11</sub>. Its systematic name is α-D-glucopyranosyl- (1↔2)-β-D-fructofuranoside (ending in "oside", because it's not a [[reducing sugar]]). It is best known for its role in [[human nutrition]] and is formed by plants but not by other [[organism]]s such as animals. ==Physical and chemical properties== Pure sucrose is most often prepared as a fine, white, odorless crystalline powder with a pleasing, sweet taste; the common table sugar. Large crystals are sometimes grown from aqueous solutions of sucrose on a string (or other [[nucleation]] surface) to form [[rock candy]], a [[confection]]. Like other [[carbohydrates]], sucrose has a [[hydrogen]] to [[oxygen]] ratio of 2:1. It consists of two [[monosaccharides]], α-[[glucose]] and [[fructose]], joined by a [[glycosidic bond]] between carbon atom 1 of the glucose unit and carbon atom 2 of the fructose unit. What is notable about sucrose is that unlike most polysaccharides, the glycosidic bond is formed between the reducing ends of both glucose and fructose, and not between the reducing end of one and the nonreducing end of the other. The effect of this inhibits further bonding to other saccharide units. Since it contains no free anomeric carbon atom, it is classified as a nonreducing sugar. Sucrose melts and decomposes at 186 °C to form [[caramel]], and when combusted produces [[carbon]], [[carbon dioxide]], and [[water]]. Water breaks down sucrose by [[hydrolysis]], however the process is so gradual that it could sit in solution for years with negligible change. If the [[enzyme]] [[sucrase]] is added however, the reaction will proceed rapidly. Reacting sucrose with [[sulfuric acid]] dehydrates the sucrose and forms the element [[carbon]], as demonstrated in the following equation: :C<sub>12</sub>H<sub>22</sub>O<sub>11</sub> + H<sub>2</sub>SO<sub>4</sub> [[catalyst]] → 12 C + 11 H<sub>2</sub>O ==Commercial production and use== {{main|Sugar}} Sucrose is the most common food [[sweetener]], although it has been replaced in American industrial food production by other sweeteners such as [[high-fructose corn syrup|fructose syrup]]s or combinations of functional ingredients and high intensity sweeteners. This is due to the subsidization of corn in the United States, which has led to a vast surplus. Combined with sugar tariffs, this has driven the price of [[corn syrup]] far below that of sugar.{{Fact|date=June 2008}} Sucrose is the most important sugar in [[plants]], and can be found in the [[phloem]] sap. It is generally extracted from [[sugar cane]] or [[sugar beet]] and then purified and crystallized. Other (minor) commercial sources are sweet [[sorghum]] and [[sugar maple]]s. Sucrose is ubiquitous in food preparations due to both its [[sweetness]] and its functional properties; it is important to the structure of many foods including biscuits and cookies, cakes and pies, candy canes, ice cream and sorbets, and also assists in the preservation of foods. As such it is common in many processed and so-called “[[junk food]]s.” <br> ==Sugar as a macronutrient== [[Image:Sugar 2xmacro.jpg|thumb|left|200px|Granulated sucrose]] In mammals, sucrose is very readily [[digestion|digested]] in the [[stomach]] into its component sugars, by acidic [[hydrolysis]]. This step is performed by a [[glycoside hydrolase]], which catalyzes the hydrolysis of sucrose to the monosaccharides glucose and fructose. Glucose and fructose are rapidly absorbed into the [[bloodstream]] in the [[small intestine]]. Undigested sucrose passing into the intestine is also broken down by [[sucrase]] or isomaltase [[glycoside hydrolases]], which are located in the [[cell membrane|membrane]] of the [[microvilli]] lining the [[duodenum]]. These products are also transferred rapidly into the bloodstream. Sucrose is digested by the enzyme [[invertase]] in [[bacteria]] and some [[animals]]. Acidic hydrolysis can be used in laboratories to achieve the hydrolysis of sucrose into glucose and fructose. ===In human nutrition=== Sucrose is an easily assimilated [[macronutrient (nutrition)|macronutrient]] that provides a quick source of energy to the body, provoking a rapid rise in [[blood glucose]] upon ingestion. However, pure sucrose is not normally part of a human diet balanced for good nutrition, although it may be included sparingly to make certain foods more palatable. Overconsumption of sucrose has been linked with some adverse [[health effects]]. The most common is [[dental caries]] or [[tooth decay]], in which oral bacteria convert sugars (including sucrose) from food into acids that attack tooth enamel. Sucrose, as a pure [[carbohydrate]], has an [[energy]] content of 3.94 [[kilocalorie]]s per gram (or 17 [[kilojoule]]s per gram). When a large amount of foods that contain a high percentage of sucrose is consumed, beneficial nutrients can be displaced from the diet, which can contribute to an increased risk for chronic disease. It has been suggested that sucrose-containing drinks may be linked to the development of obesity and [[insulin resistance]].<ref>Ten, S. & Maclaren, N. (2004). [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=15181020&query_hl=1&itool=pubmed_DocSum Insulin resistance syndrome in children]. J Clin Endocrinol Metab. 2004 Jun;89(6):2526-39.</ref> Although most soft drinks in the USA are now made with [[high fructose corn syrup]], not sucrose, this makes little functional difference, since [[high fructose corn syrup]] contains fructose and glucose in a similar ratio to that produced metabolically from sucrose. The rapidity with which sucrose raises blood glucose can cause problems for people suffering from defects in glucose metabolism, such as persons with [[hypoglycemia]] or [[diabetes mellitus]]. Sucrose can contribute to development of the [[metabolic syndrome]].<ref>Aguilera, A.A., et al. (2004). [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=15157941&query_hl=1&itool=pubmed_DocSum Effects of fish oil on hypertension, plasma lipids, and tumor necrosis factor-alpha in rats with sucrose-induced metabolic syndrome.]. J Nutr Biochem. 2004 Jun;15(6):350-7.</ref> In an experiment with rats that were fed a diet one-third of which was sucrose, the sucrose first elevated blood levels of [[triglyceride]]s, which induced [[visceral]] fat and ultimately resulted in [[insulin resistance]].<ref>{{cite journal | author=Satoshi Fukuchi | title=Role of Fatty Acid Composition in the Development of Metabolic Disorders in Sucrose-Induced Obese Rats | journal=Experimental Biology and Medicine | year=2004 | volume=229 | issue=6 | pages= 486&ndash;493 | url=http://www.ebmonline.org/cgi/content/full/229/6/486 | pmid=15169967}}</ref> Another study found that rats fed sucrose-rich diets developed [[hypertriglyceridemia|high triglycerides]], [[hyperglycemia]], and [[insulin resistance]].<ref>Lombardo, Y.B., et al. (1996). [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=8969287&query_hl=1&itool=pubmed_DocSum Long-term administration of a sucrose-rich diet to normal rats: relationship between metabolic and hormonal profiles and morphological changes in the endocrine pancreas]. Metabolism. 1996 Dec;45(12):1527-32.</ref> ==References== ===Notes=== {{reflist}} ===General references=== *{{cite book | first=J. | last=Yudkin | coauthors=Edelman, J., Hough, L. | title=Sugar - Chemical, Biological and Nutritional Aspects of Sucrose | publisher=The Butterworth Group | year=1973 | id=ISBN 0-408-70172-2}} ==External links== *[http://www.compchemwiki.org/index.php?title=Sucrose Computational Chemistry Wiki] *[http://www.chem.qmul.ac.uk/iupac/2carb/app.html Nomenclature of Carbohydrates] *[http://csi.chemie.tu-darmstadt.de/ak/immel/graphics/gallery/sucroses.html 3d Images of Sucrose] {{Carbohydrates}} [[Category:Disaccharides]] [[Category:Sweeteners]] [[ar:سكروز]] [[zh-min-nan:Chià-thn̂g]] [[bg:Захароза]] [[ca:Sacarosa]] [[cs:Sacharóza]] [[da:Sukrose]] [[de:Saccharose]] [[et:Sahharoos]] [[es:Sacarosa]] [[eo:Sakarozo]] [[fr:Saccharose]] [[ko:자당]] [[is:Súkrósi]] [[it:Saccarosio]] [[he:סוכרוז]] [[la:Saccharosium]] [[lb:Saccharos]] [[lt:Sacharozė]] [[ms:Sukrosa]] [[nl:Sacharose]] [[ja:スクロース]] [[no:Rørsukker]] [[nn:Sukrose]] [[pl:Sacharoza]] [[pt:Sacarose]] [[ru:Сахароза]] [[sq:Sakaroza]] [[sl:Saharoza]] [[sr:Сахароза]] [[fi:Sakkaroosi]] [[sv:Rörsocker]] [[th:ซูโครส]] [[uk:Цукроза]] [[zh:蔗糖]]