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

LogP

-2.71 at 25℃

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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

F 

3

TSCA 

Yes

HS Code 

29400010

MSDS

• Language:English Provider:D-(+)-Mannose
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

D-Mannose Usage And Synthesis

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] http://www.webmd.com
[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

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.

Uses

D-mannose acts as an alternative energy source utilized by brain. It is used in the study of assessing the synthesis of amphiphilic glycopolymers and investigating early detection of bronchiolitis obliterans.It may be useful in the treatment of urinary tract infections (UTIs) and carbohydrate-deficient glycoprotein syndrome type 1b. It is also useful in the formation of glycan structure and glycosylation.

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.

Application

D-mannose is a simple sugar structurally related to glucose. It is absorbed slowly from the gastrointestinal tract, and then a large proportion of it is excreted into the urine.
D-(+)-Mannose has been used:
as a reference standard in monosaccharide analysis and quantification from sea squirts Ascidiella aspersa
as a medium component for the selection of P898012 sorgum seeds transfected with Agrobacterium
in segmented filamentous bacterium (SFB) medium supplement for culturing human cell lines
Mannose is an aldohexose carbohydrate. It is isomer of glucose with varying C2 position configuration. Majority of mannose is synthesised from its epimer glucose. It is part of the glycans present in endoplasmic reticulum (ER)/Golgi.

Definition

ChEBI: D-Mannopyranose having alpha-configuration at the anomeric centre.

General Description

Mannose is a monosaccharide.

Flammability and Explosibility

Not classified

Biochem/physiol Actions

Mannose, a six-carbon carbohydrate, is the C-2 epimer of glucose and a critical sugar for protein glycosylation. Mannose can also be utilized by the brain as an alternative energy source.

Side effects

D-mannose appears to be generally well tolerated in people. You should be cautious about using D-mannose if you are pregnant or breastfeeding, because there has not been enough study on its safety in these circumstances. Side effects of D-mannose may include: bloating and loose stools. D-mannose supplements should be used with caution if you have diabetes. It may make it harder to control your blood sugar. High doses of D-mannose may cause kidney damage.

Source

D-mannose is a sugar that can be found in some fruits and vegetables, such as oranges, apples, peaches, broccoli and green beans. It has been used in the past to treat UTIs in animals. Now, there is some interest into whether it could also treat and prevent UTI in humans.
D-mannose is a naturally occurring simple sugar that your body utilizes to help cleanse the urinary tract and maintain a healthy bladder lining. It’s metabolized only in small amounts, with excess amounts rapidly excreted in urine, so it won’t interfere with healthy blood sugar regulation. Clinical studies have demonstrated that, when taken regularly, D-mannose promotes normal urinary tract function by cleansing and maintaining the health of the bladder lining.

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

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