Sucrose
From Wikipedia, the free encyclopedia
| Sucrose | |
|---|---|
|
|
|
| General | |
| Systematic name | Sucrose |
| Other names | Sugar, Saccharose |
| atomic formula | C12H22O11 |
| SMILES | OC1C(OC(CO)C(O)C1O) OC2(CO)OC(CO)C(O)C2O |
| Molar mass | 342.29648 g/mol |
| Appearance | white solid |
| CAS number | [57-50-01] |
| Chemical Properties | |
| Density and phase | 1.587 g/cm³, solid |
| Solubility in water | 211.5 g/100 ml (25°C) |
| Melting point | 186°C (459.15 K) |
| Boiling point | decomposition |
| Chiral rotation [α]D | +66.47° |
| Refractive index | 1.5376 |
| Structure | |
| Molecular shape | ? |
| Crystal structure | monoclinic hemihedral |
| Dipole moment | ? D |
| Hazadrs | |
| MSDS | External MSDS |
| Main hazards | Combustible |
| NFPA 704 |
1
1
0
|
| Flash point | N/A |
| R/S statement | R: ? S: ? |
| RTECS number | WN6500000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Other anions | ? |
| Other cations | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references |
|
| Solubility of Pure Sucrose | |
|---|---|
| Temperature(C) | g sucrose/g water |
| 50 | 2.59 |
| 55 | 2.73 |
| 60 | 2.89 |
| 65 | 3.06 |
| 70 | 3.25 |
| 75 | 3.46 |
| 80 | 3.69 |
| 85 | 3.94 |
| 90 | 4.20 |
Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. Its systematic name is α-D-glucopyranosyl-(1→2)-β-D-fructofuranose. It is best known for its role in human nutrition and is formed by plants but not by higher organisms.
Contents |
[edit] Physical and chemical properties
Pure sucrose is most often prepared as a fine, white, odorless crystalline powder with a pleasing, sweet taste. Large crystals are sometimes precipitated from water solutions of sucrose onto 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 elemental carbon, as demonstrated in the following equation:
- C12H22O11 + H2SO4 catalyst → 12 C + 11 H2O
[edit] Commercial production and use
Sucrose is the most common food sweetener in the industrialized world, although it has been replaced in American industrial food production by other sweeteners such as fructose syrups or combinations of functional ingredients and high intensity sweeteners. This is due to the extremely high tariffs charged to import sugar into America.
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 maples.
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, candycanes, ice cream and sorbets, and also assists in the preservation of foods. As such it is common in many processed and so-called “junk foods.”
[edit] Sugar as a macronutrient
Human beings, and in fact most other mammals—except felines, which lack the ability to taste sweetness[1]—will typically accept food sweetened with sucrose even if they are not hungry (see Dessert) because of its pleasurable taste to them.
In mammals, sucrose is very readily 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 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.
[edit] In human nutrition
Sucrose is an easily assimilated 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, or bearable to eat because of their vile taste to humans.
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 4 kilocalories per gram (or 17 kilojoules per gram). When a large amount of foods that contain a high percentage of sucrose is consumed, beneficial nutrients can be misplaced 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[2].
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[3]. In an experiment with rats that were fed a diet one-third of which was sucrose, the sucrose first elevated blood levels of triglycerides, which induced visceral fat and ultimately resulted in insulin resistance [4]. Another study found that rats fed sucrose-rich diets developed high triglycerides, hyperglycemia, and insulin resistance [5].
[edit] References
- ^ Xia, Li; et.al. (July 2005). Pseudogenization of a Sweet-Receptor Gene Accounts for Cats' Indifference toward Sugar. Public Library of Science. Retrieved on 2006-07-15.
- ^ Ten, S. & Maclaren, N. (2004). Insulin resistance syndrome in children. J Clin Endocrinol Metab. 2004 Jun;89(6):2526-39.
- ^ Aguilera, A.A., et al. (2004). 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.
- ^ Satoshi Fukuchi (2004). "Role of Fatty Acid Composition in the Development of Metabolic Disorders in Sucrose-Induced Obese Rats". Experimental Biology and Medicine 229 (6): 486–493. PMID 15169967.
- ^ Lombardo, Y.B., et al. (1996). 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.
Yudkin, J.; Edelman, J., Hough, L. (1973). Sugar - Chemical, Biological and Nutritional Aspects of Sucrose. The Butterworth Group. ISBN 0-408-70172-2.
[edit] External links
- Flash animation at McGraw-Hill biochemistry-Enzyme%20Action%20and%20the%20Hydrolysis%20of%20Sucrose
- Computational Chemistry Wiki
- Nomenclature of Carbohydrates
- 3d Images of Sucrose
- Links to external chemical sources
