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| CAS No.: | 7512-17-6 |
|---|---|
| Name: | N-Acetyl-D-Glucosamine |
| Article Data: | 146 |
| Molecular Structure: | |
|
|
|
| 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: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 24/25-36-26 |
| PSA: | 127.09000 |
| LogP: | -2.84410 |
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| Conditions | Yield |
|---|---|
| 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
- 373-02-4, 14998-37-9, 33025-09-1, 94044-50-5, 98268-31-6
nickel diacetate
- 7512-17-6
2-acetamido-2-deoxy-D-glucose
| Conditions | Yield |
|---|---|
| at 100℃; |
| Conditions | Yield |
|---|---|
| With methanol; triethylamine |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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; |
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Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester
- 7512-17-6
2-acetamido-2-deoxy-D-glucose
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With Amberlite IR-120 (H+) |
| Conditions | Yield |
|---|---|
| With methanol; acetic anhydride Ambient temperature; |
- 14131-64-7
N-acetyl-D-mannosamine
- 7512-17-6
2-acetamido-2-deoxy-D-glucose
| Conditions | Yield |
|---|---|
| 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:
Xi
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]](/UserFilesUpload/Uses of 2-Acetamido-2-deoxy-D-glucose.jpg)
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.