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Basic Information
CAS No.: 7512-17-6
Name: N-Acetyl-D-Glucosamine
Article Data: 146
Molecular Structure:
Molecular Structure of 7512-17-6 (N-Acetyl-D-Glucosamine)
Formula: C8H15NO6
Molecular Weight: 221.21
Synonyms: 2-Acetamido-D-glucose;N-acetyl-β-D-glucosamine;2-Acetamido-2-deoxy-D-glucose;N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide;N-acetyl D-Glucosamine;D-Glucose, 2-(acetylamino)-2-deoxy-;
EINECS: 231-368-2
Density: 1.423 g/cm3
Melting Point: 211 °C (dec.)(lit.)
Boiling Point: 636.4 °C at 760 mmHg
Flash Point: 338.7 °C
Solubility: H2O: 50 mg/mL colorless to faint yellow solution, clear to very slightly hazy
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36-26
PSA: 127.09000
LogP: -2.84410
Synthetic route
chitosan (deacetylation degree, 93%)

chitosan (deacetylation degree, 93%)

127-09-3

sodium acetate

A

chitosan oligosaccharides

chitosan oligosaccharides

B

3416-24-8

2-amino-2-deoxyglucose

C

7512-17-6

2-acetamido-2-deoxy-D-glucose

D

Low molecular weight chitosan

Low molecular weight chitosan

Conditions
ConditionsYield
With chitosanase In water at 40℃; for 20h; pH=4.5; Product distribution; Further Variations:; Reagents; pH-values; Enzymatic reaction;A 46.3%
B n/a
C n/a
D 44.6%
110-86-1

pyridine

14131-64-7

N-acetyl-D-mannosamine

7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
at 100℃;
463-51-4

Ketene

66-84-2

D-(+)-glucosamine hydrochloride

7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With methanol; triethylamine
3416-24-8

2-amino-2-deoxyglucose

108-24-7

acetic anhydride

7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With methanol
In methanol; N,N-dimethyl-formamide
108-24-7

acetic anhydride

66-84-2

D-(+)-glucosamine hydrochloride

7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With methanol; basic ion exchanger; water
With methanol; silver(I) acetate
Stage #1: D-(+)-glucosamine hydrochloride In water Industry scale;
Stage #2: acetic anhydride With sodium carbonate In water at 20 - 25℃; pH=4 - 6; Product distribution / selectivity; Industry scale;
Conditions
ConditionsYield
With ammonia
108-24-7

acetic anhydride

77045-60-4

2-amino-2-deoxy-D-glucose hydrazone

A

7512-17-6

2-acetamido-2-deoxy-D-glucose

B

97055-07-7

1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetylhydrazine

Conditions
ConditionsYield
With Amberlite IR-120 (H+) and IRA-400 (AcO-); sodium acetate In methanol; water
With sodium acetate In methanol; water for 1h; Ambient temperature;
97055-07-7

1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetylhydrazine

7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With Amberlite IR-120 (H+)
3867-92-3

methyl 2-amino-2-deoxy-β-D-glucopyranoside

7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With methanol; acetic anhydride Ambient temperature;
14131-64-7

N-acetyl-D-mannosamine

diluted aqueous solution

diluted aqueous solution

7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
pH 11;
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Specification

1. Introduction of 2-Acetamido-2-deoxy-D-glucose
With the EINECS registry number 231-368-2, 2-Acetamido-2-deoxy-D-glucose is also called 2-(acetylamino)-2-deoxy-D-glucose. What's more, 2-Acetamido-2-deoxy-D-glucose is a kind of white powder which can be used to treat osteoarthritis and rheumatoid arthritis.

2. Properties of 2-Acetamido-2-deoxy-D-glucose
(1)ACD/LogP: -2.68; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -2.68; (4)ACD/LogD (pH 7.4): -2.68; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 7; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 74.3 Å2; (13)Index of Refraction: 1.541; (14)Molar Refractivity: 48.89 cm3; (15)Molar Volume: 155.3 cm3; (16)Polarizability: 19.38 ×10-24cm3; (17)Surface Tension: 69.6 dyne/cm; (18)Density: 1.423 g/cm3; (19)Flash Point: 338.7 °C; (20)Enthalpy of Vaporization: 107.73 kJ/mol; (21)Boiling Point: 636.4 °C at 760 mmHg; (22)Vapour Pressure: 7.12E-19 mmHg at 25°C.

3. Structure Descriptors of 2-Acetamido-2-deoxy-D-glucose
(1)SMILES: O=C[C@H](NC(=O)C)[C@@H](O)[C@H](O)[C@H](O)CO
(2)Std. InChI: InChI=1S/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6+,7+,8+/m0/s1
(3)Std. InChIKey: MBLBDJOUHNCFQT-LXGUWJNJSA-N

4. Safety Information of 2-Acetamido-2-deoxy-D-glucose
Hazard Symbols:IrritantXi
Risk Codes:
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Description:
S24/25:Avoid contact with skin and eyes. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

5. Preparation of 2-Acetamido-2-deoxy-D-glucose
Several crude enzymes including cellelase Tv, hemicellulase and lipase, papain as well as exllulase Ac were examined for the effective production of 2-Acetamido-2-deoxy-D-glucose from amorphous α-chitin. Among the tested crude enzymes, cellulase Iv was found to be the most effective for directly degrading amorphous α-chitin to 2-Acetamido-2-deoxy-D-glucose. High yield of 2-Acetamido-2-deoxy-D-glucose was achieved by choosing the optimum hydrolytic conditons at PH 4.5 and 37°C. By gradually adding, in three tantamount cases, the amount of cellulase Tv amorphous α-chitin, the yield of 2-Acetamido-2-deoxy-D-glucose reach 55%.

6. Use of 2-Acetamido-2-deoxy-D-glucose
Uses of 2-Acetamido-2-deoxy-D-glucose can react with phenylmethanol to get N-(O1-benzyl-a-D-glucopyranose-2-yl)-acetamide]. This reaction will need reagent BF3*Et2O. The reaction time is 6 hours by heating. The yield is about 47%.

2-Acetamido-2-deoxy-D-glucose can react with phenylmethanol to get N-(O1-benzyl-a-D-glucopyranose-2-yl)-acetamide]

7. Other details of 2-Acetamido-2-deoxy-D-glucose
When you are using 2-Acetamido-2-deoxy-D-glucose, please be cautious about it as the following:
2-Acetamido-2-deoxy-D-glucose is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.