D-(+)-Trehalose,无水海藻糖

a,a-D-Trehalose anhydrous

Trehalose is a sugar that is found in many organisms, including humans. It is a disaccharide composed of two glucose units. Trehalose has been shown to be effective against infectious diseases such as HIV and malaria. Trehalose may have anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines such as tumor necrosis factor alpha (TNF-α) and interleukin 6 (IL-6). The water vapor pressure of trehalose dihydrate is higher than that of trehalose anhydrous, which may account for its greater stability under high humidity conditions.

Trehalose, also known as alpha-D-trehalose or (GLC)2, 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. Trehalose exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Trehalose has been found in human kidney, muscle and epidermis tissues, and has also been detected in multiple biofluids, such as feces and urine. Trehalose exists in all eukaryotes, ranging from yeast to humans. Trehalose participates in a number of enzymatic reactions. In particular, Trehalose can be converted into Beta-D-glucose and Alpha-D-glucose; which is catalyzed by the enzyme trehalase. In addition, Trehalose can be biosynthesized from trehalose 6-phosphate through its interaction with the enzyme trehalose 6-phosphate synthase. In humans, trehalose is involved in the trehalose degradation pathway. Outside of the human body, trehalose can be found in a number of food items such as salmonberry, globe artichoke, banana, and butternut squash. This makes trehalose a potential biomarker for the consumption of these food products.

Alpha,alpha-trehalose is a trehalose in which both glucose residues have alpha-configuration at the anomeric carbon. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite.

Cabaletta has been used in trials studying the treatment of Oculopharyngeal Muscular Dystrophy.

Title: Trehalose

CAS Registry Number: 99-20-7

CAS Name: a-D-Glucopyranosyl-a-D-glucopyranoside

Additional Names: mushroom sugar; mycose; a,a-trehalose

Molecular Formula: C12H22O11

Molecular Weight: 342.30

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

Literature References: Non-reducing disaccharide found in fungi, bacteria, yeasts, and insects; 45% as sweet as sucrose. Provides the energy source for flight in many insects. Incorporated into mycobacterial structural glycolipids such as cord factors, q.v. Isoln from the ergot of rye: H. A. L. Wiggers, Ann. 1 129 (1832). Prepn and review of early history: T. S. Harding, Sugar 25, 476-478 (1923). Isoln from yeast: E. M. Koch, F. C. Koch, Science 61, 570 (1925); L. C. Stewart et al., J. Am. Chem. Soc. 72, 2059 (1950). Synthesis: Lemieux, Bauer, Can. J. Chem. 32, 340 (1954). Crystal structure: G. A. Jeffrey, R. Nanni, Carbohydr. Res. 137, 21 (1985). Review of metabolism: A. D. Elbein, Adv. Carbohydr. Chem. Biochem. 30, 227-256 (1974). In vitro evaluation in cryopreservation of human oocytes: A. Eroglu et al., Fertil. Steril. 77, 152 (2002). Use in freeze-drying human platelets: W. F. Wolkers et al., Cryobiology 42, 79 (2001); eidem, Cell Preservation Technol. 1, 175 (2003). Review of properties, toxicity and safety studies: A. B. Richards et al., Food Chem. Toxicol. 40, 871-898 (2002); of stabilizing functions and applications: T. Higashiyama, Pure Appl. Chem. 74, 1263-1269 (2002).

Derivative Type: Dihydrate

CAS Registry Number: 6138-23-4

Properties: Orthorhombic, bisphenoidal crystals from dil alcohol. Sweet taste. mp 96.5-97.5°. The water of crystn escapes around 130°. Anhydrous trehalose melts at 203°. [a]D20 +178° (c = 7 of the dihydrate). Sol in water, hot alcohol. Insol in ether. Does not reduce Fehling's soln. Is fermented by yeast. Is not split by a-glucosidase. Acid hydrolysis gives 2 mols D-glucose.

Melting point: mp 96.5-97.5°

Optical Rotation: [a]D20 +178° (c = 7 of the dihydrate)

Use: Stabilizes cells during freezing, freeze-drying and air-drying. Sweetener and stabilizer in foods; cryoprotectant for freeze-dried foods. Additive in cosmetics and personal care products.

COA: 

Product name: D-(+)-Trehalose CAS: 99-20-7

M.F.: C₁₂H₂₂O₁₁   M.W.: 342.30      Batch No: 20130105   Quantity:6.4kg