蔗糖, D-Sucrose

Useful in density gradient centrifugation for nucleic acid purification and as a carbohydrate source in cell culture.

Sucrose, also known as cane sugar or saccharose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Sucrose exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Sucrose has been found throughout most human tissues, and has also been detected in most biofluids, including blood, saliva, feces, and urine. Within the cell, sucrose is primarily located in the myelin sheath. Sucrose exists in all eukaryotes, ranging from yeast to humans. Sucrose participates in a number of enzymatic reactions. In particular, Sucrose and D-galactose can be biosynthesized from raffinose through the action of the enzyme Alpha-galactosidase a. Furthermore, Sucrose can be converted into D-galactose and D-fructose; which is mediated by the enzyme lysosomal alpha-glucosidase. Finally, Sucrose can be biosynthesized from Alpha-D-glucose and D-fructose through its interaction with the enzyme sucrase-isomaltase, intestinal. In humans, sucrose is involved in the galactose metabolism pathway and the starch and sucrose metabolism pathway. Sucrose is also involved in several metabolic disorders, some of which include the glycogenosis, type iii. cori disease, debrancher glycogenosis pathway, the glycogenosis, type vi. hers disease pathway, the galactosemia pathway, and the mucopolysaccharidosis vi. sly syndrome pathway. Outside of the human body, sucrose can be found in a number of food items such as horchata, eastern oyster, corn grits, and rye. This makes sucrose a potential biomarker for the consumption of these food products.

Sucrose appears as white odorless crystalline or powdery solid. Denser than water.

Sucrose is a glycosyl glycoside formed by glucose and fructose units joined by an acetal oxygen bridge from hemiacetal of glucose to the hemiketal of the fructose. It has a role as an osmolyte, a sweetening agent, a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite.

Consumed in large amounts around the world as a food ingredient. Other applications of sucrose include its use in surfactants (esters), polyurethanes (polyols), plastics (alkyds) to produce dextrans (Leuconostoc mesenteroides fermentation) and ethanol (Saccharomyces cerevisiae fermentation). 

Title: Sucrose

CAS Registry Number: 57-50-1

CAS Name: b-D-Fructofuranosyl-a-D-glucopyranoside

Additional Names: a-D-glucopyranosyl-b-D-fructofuranoside; sugar; saccharose; cane sugar; beet sugar

Molecular Formula: C12H22O11

Molecular Weight: 342.30

Percent Composition: C 42.11%, H 6.48%, O 51.41%

Literature References: Obtained from sugar cane (Saccharum officinarum L., Gramineae) and sugar beet (Beta valgaris L., Chenopodiaceae). Sugar cane contains from 15-20% and sugar beet from 10-17% sucrose. Structure: Avery et al., J. Chem. Soc. 1927, 2308; Beevers, Cochrane, Proc. Roy. Soc. 190A, 257 (1947). Synthesis: Pictet, Vogel, Helv. Chim. Acta 11, 436 (1928); Lemieux, Huber, J. Am. Chem. Soc. 78, 4117 (1956). Ref. with extensive bibliography: Bates, Polarimetry, Saccharimetry, and the Sugars, National Bureau of Standards Circular C440, Washington, 1942; W. Pigman, The Carbohydrates (Academic Press, New York, 1957) pp 501-506. Reviews: M. R. Jenner, Dev. Food Carbohydr. 2, 91-143 (1980); R. Khan, Pure Appl. Chem. 56, 833 (1984).

Properties: Monoclinic sphenoidal crystals, cryst masses, blocks, or powder. Sweet taste. Stable in air. Finely divided sugar is hygroscopic and absorbs up to 1% moisture which is given up on heating to 90°. d425 1.587. Dec 160-186°. Chars and emits characteristic odor of caramel. [a]D20 not less than +65.9° (c = 26); usual value [a]D25 +66.47 to +66.49°. One gram dissolves in 0.5 ml water; in slightly more than 0.2 ml boiling water, in 170 ml alcohol; in about 100 ml methanol. Moderately sol in glycerol, pyridine. pKa 12.62. d420 of water solns (g/100 g): 2% 1.0060; 6% 1.0219; 10% 1.0381; 20% 1.0810; 30% 1.1270; 40% 1.1764; 50% 1.2296; 60% 1.2865; 70% 1.3471; 76% 1.3854. nD20 of 10% soln 1.34783. Sucrose does not reduce Fehling's soln, form an osazone, or show mutarotation. It is hydrolyzed to glucose and fructose by dil acids and by invertase, a yeast enzyme. Upon hydrolysis the optical rotation falls and is negative when the hydrolysis is complete. The mixture of glucose and fructose is known as "invert sugar." Sucrose is fermentable, but resists bacterial decompn when in high concentrations.

pKa: pKa 12.62

Optical Rotation: [a]D20 not less than +65.9° (c = 26); [a]D25 +66.47 to +66.49°

Index of refraction: nD20 of 10% soln 1.34783

Density: d425 1.587; d420 of water solns (g/100 g): 2% 1.0060; 6% 1.0219; 10% 1.0381; 20% 1.0810; 30% 1.1270; 40% 1.1764; 50% 1.2296; 60% 1.2865; 70% 1.3471; 76% 1.3854

CAUTION: Potential symptoms of overexposure are irritation of eyes, skin, upper respiratory system; cough. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 288.

Use: Sweetening agent and food. Starting material in the fermentative production of ethanol, butanol, glycerol, citric and levulinic acids. Used in pharmaceuticals as a flavor, as a preservative, as an antioxidant (in the form of invert sugar), as a demulcent, as substitute for glycerol, as granulation agent and excipient for tablets, as coating for tablets. In the plastics and cellulose industry, in rigid polyurethane foams, manuf of ink and of transparent soaps.