D-Mannose Cas 3458-28-4

Product Name: D-Mannose
Synonyms: DL-allo-2,3,4,5,6-Pentahydroxy-hexanal;d-[1,2,3-13C3]Mannose;d-[1-12C]Mannose (13C depleted at C1);d-[1-13C:1-2H]Mannose;d-[1-18O]Mannose;d-[2,3,4,5,6-13C5]Mannose;d-[3,4-13C2]Mannose;d-[UL-12C6]Mannose (13C depleted)
CAS: 3458-28-4
MF: C6H12O6
MW: 180.16
EINECS: 222-392-4
Product Categories: Sugars, Carbohydrates & Glucosides;Carbohydrates;13C & 2H Sugars;Basic Sugars (Mono & Oligosaccharides);Biochemistry;Sugars;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives;carbohydrate
Mol File: 3458-28-4.mol
D-Mannose Structure
D-Mannose Chemical Properties
Melting point 133-140 ®C(lit.)
alpha 14 º (589nm, c=10, H2O)
Boiling point 232.96®C (rough estimate)
density 1,539 g/cm3
refractive index 1.5730 (estimate)
storage temp. room temp
solubility H2O: 50 mg/mL
form powder
pka 12.08(at 25℃)
color White
optical activity [α]20/D +13.8¯0.5®, 24 hr, c = 10% in H2O
Water Solubility 2480 g/L (17 ºC)
λmax λ: 260 nm Amax: 0.1
λ: 280 nm Amax: 0.1
Sensitive Hygroscopic
Merck 14,5747
BRN 1564373
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey WQZGKKKJIJFFOK-ATJJXCEKSA-N
CAS DataBase Reference 3458-28-4(CAS DataBase Reference)
NIST Chemistry Reference D-Mannose(3458-28-4)
EPA Substance Registry System D-Mannose (3458-28-4)
Description D-Mannose is a nutritional supplement that can be found in cranberries, peaches, apples, other berries, and some plants. D-mannose is a sugar that has an important role in human metabolism, especially in the glycosylation of certain proteins. D-mannose functionalizes by the inhibition of bacterial adherence to uroepithelial cells.
More than 90 percent of recurrent urinary tract infections (UTIs) are caused by Escherichia coli (E. coli), which is normally found in the intestinal tract. The cell walls of each E. coli are covered with tiny fingerlike projections called fimbria. Mannose can bind to the lectin on the bacteria’s fimbria so that the bacteria can be effectively rinsed out by urination.
D-Mannose is by far the most effective supplement for both treatment and prevention of UTIs. And it is used for the treating carbohydrate-deficient glycoprotein syndrome, an inherited metabolic disorder.
References [1] *
[2] Bojana Kranjcˇec, Dino Papesˇ , Silvio Altarac (2013) D-mannose powder for prophylaxis of recurrent urinary tract infections in women: a randomized clinical trial, World J Urol, 32, 79-84
Chemical Properties White crystalline powder
Uses D-Mannose is a carbohydrate that is important in the glycosylation of molecules in a variety of cellular processes. It is involved in N and O glycosylation of bovine why protein products, used in inf ant formulas. It is also responsible for the O-glycosylation of the T helper cell-derived cytokine interlukin-17A, an important cell-signaling molecule.
Uses It has been used in a study to assess the synthesis of a family of amphiphilic glycopolymers. It has also been used in a study to investigate the early detection of bronchiolitis obliterans after lung transplantation.
Definition ChEBI: D-Mannopyranose having alpha-configuration at the anomeric centre.
Purification Methods Crystallise -D(+)-mannose repeatedly from EtOH, aqueous 80% EtOH, AcOH or MeOH/propan-2-ol and then dry it in vacuo over P2O5 at 60o. [For 1H NMR and equilibr