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Home> Encyclopedia >Vitamins, Amino Acids and Coenzymes>Pharmaceutical Intermediates>Organic Intermediate
D-Mannose structure
D-Mannose structure

D-Mannose

CAS No.: 3458-28-4
Molecular Weight:180.15588
Modify Date.: 2022-11-29 11:16
Introduction: 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. View more+
1. Names and Identifiers
1.1 Name
D-Mannose
1.2 Synonyms

Anhydro-mannose Carubinose D(+)-Mannose NSC 26247 Seminose

1.3 CAS No.
3458-28-4
1.4 EINECS(EC#)
222-392-4
1.5 Molecular Formula
C6H12O6 (isomer)
1.6 Inchi
InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2
1.7 InChkey
GZCGUPFRVQAUEE-KVTDHHQDSA-N
1.8 Canonical Smiles
OCC(O)C(O)C(O)C(O)C=O
1.9 Isomers Smiles
O=CC(O)C(O)C(O)C(O)CO
2. Properties
2.1 Density
1.53
2.1 Melting point
133-140℃
2.1 Boiling point
410.8 °C at 760 mmHg
2.1 Refractive index
1.5730 (estimate)
2.1 Flash Point
202.2 °C
2.1 Precise Quality
180.06300
2.1 PSA
118.22000
2.1 logP
-3.37880
2.1 Solubility
H2O: 50?mg/mL
2.2 Appearance
White powder
2.3 Storage
Hygroscopic. Ambient temperatures.
2.4 Chemical Properties
White crystalline powder
2.5 Color/Form
White
2.6 pKa
12.08(at 25℃)
2.7 Water Solubility
H2O: 2480 g/L (17 oC)
2.8 Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
2.9 StorageTemp
Store at RT.
3. Use and Manufacturing
3.1 Definition
ChEBI: D-Mannopyranose having alpha-configuration at the anomeric centre.
3.2 Methods of Manufacturing
The coconut shell is hydrolyzed with sulfuric acid to obtain α-mannose.
3.3 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 D-Mannose Preparation Products And Raw materials Raw materials
3.4 Usage
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 infant formulas. It is also responsible for the O-glycosylation of the T helper cell-derived cytokine interlukin-17A, an important cell-signaling molecule.
4. Safety and Handling
4.1 Hazard Codes
Xi
4.1 Risk Statements
36/37/38
4.1 Safety Statements
S24/25
4.1 WGK Germany
3
4.1 Specification

The D-Mannose , with the CAS register number 3458-28-4, has other names as carubinose;d-mannopyranose;d-(+)-mannose;d-mannose;d-man;mannose, d-(+)-;seminose;d-mannos .

The physical properties of this kind of chemcial are as followings: (1)#H bond acceptors:? 6? ; (2)#H bond donors:? 5? ; (3)#Freely Rotating Bonds:? 6? ; (4)Polar Surface Area:? 55.38? ; (5)Index of Refraction:? 1.635? ; (6)Molar Refractivity:? 37.25 cm3? ; (7)Molar Volume:? 104 cm3? ; (8)Polarizability:? 14.76 ×10-24 cm3? ; (9)Surface Tension:? 81.7 dyne/cm? ; (10)Density:? 1.732 g/cm3? ; (11)Flash Point:? 202.2 °C? ; (12)Enthalpy of Vaporization:? 76.63 kJ/mol? ; (13)Boiling Point:? 410.8 °C at 760 mmHg? ; (14)Vapour Pressure:? 1.83E-08 mmHg at 25°C.

It is a kind of white crystalline powder and it is sweet with afteraste of bitter. And it is soluble in water and slightly soluble in ethanol but insoluble in diethyl [ethyl] ether. Besides, it has two types of α- and β-. The α- is the crystallize of methyl with the melting point of 133℃ while the β- is the crystallize of ethyl with the melting point of 132℃. As for its usage, it is usually used for being the biochemical reagents and sweet taste reagents. What's more, the simple way to get it is following:hydrolyze the cocoanut husk with sulfuric acid and then you could α- type of D-Mannose.

Its product categories are including the following: Sugars, Carbohydrates & Glucosides;Carbohydrates;13C & 2H Sugars;Basic Sugars (Mono & Oligosaccharides);Biochemistry;Sugars;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives.

Being an irritant chemical to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes. So while using this chemical, take the following instrction to protect your self: Wear suitable protective clothing and avoid contact with skin and eyes; If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And you could also obtain the safety information from WGK Germany? 3.
?
In addition, you could refer to the following data information to get the molecular structure:
SMILES:O[C@H]1[C@H](O)[C@H](OC(O)[C@H]1O)CO
InChI:InChI=1/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1
InChIKey:WQZGKKKJIJFFOK-QTVWNMPRBS

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

8. Other Information
8.0 Storage Conditions
The coconut shell is hydrolyzed with sulfuric acid to obtain α-mannose.
8.1 Mesh Entry Terms
mannose homopolymer
8.2 Usage
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.
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