N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 132354
• Molecular Formular: C8H15NO6
• Molecular Mass: 221.2078
• Monoisotopic Mass: 221.08993721
• SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](OC1O)CO)O)O
• Canonical SMILES: OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8?/m1/s1
• InChIKey: OVRNDRQMDRJTHS-RTRLPJTCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: GlcNAc
• Synonyms: D-GlcNAc; N-Acetyl-D-glucosamine; 2-Acetamido-2-deoxy-D-glucose; 2-(Acetylamino)-2-deoxy-D-glucose; NSC 524344; N-Acetyl-D-glucosamine; 2-(Acetylamino)-2-deoxy-D-glucose-2-3H; 2-Acetamido-2-deoxy-D-glucose-2-3H; N-Acetyl-D-glucosamine-2-3H; 2-乙酰胺基-2-脱氧-D葡萄糖; N-乙酰基-D-葡糖胺

Database IDs

• CAS Number: 7512-17-6
• EC Number: 231-368-2
• MDL Number: MFCD00061615
• Beilstein Number: 1727589
• PubChem SID: 162226631; 24891348; 24890757
• PubChem CID: 439174

CALCULATED PROPERTIES

• Acid pKa: 11.60413
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.2205749
• LogD (pH = 7.4): -3.2206008
• Log P: -3.2205744
• Molar Refractivity: 47.0247 cm^3
• Polarizability: 19.398714 Å^3
• Polar Surface Area: 119.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear to very slightly hazy (colorless to faint yellow solution)
• Apperance: Off-White to Tan Solid; powder; Sp. Act. ~88mCi/mmol.; white to off-white powder
• Melting Point: 211 °C (dec.)(lit.); 211°C (dec.)
• Optical Rotation: [α]20/D +42±3°, 2 hr, c = 2% in H2O; [α]25/D +40.5°, c = 1 in H2O

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPAE); ≥99%; ≥99.0% (sum of enantiomers, HPLC); 99%
• Suitability: suitable for cell culture
• Empirical Formula (Hill Notation): C8H15NO6

DETAILS

Sigma Aldrich - A4106

Application
N-Acetyl-D-glucosamine (D-GlcNAc) is a derivitized glucose monomer found in polymers of bacterial cell walls, chitin, hyaluronic acids and various glycans. D-GlcNAc is used to identify, differentiate and characterize N-acetyl-β-D-hexoaminidase(s).

Sigma Aldrich - A8625

Application
Do you have application information on this product that you would like to share?
N-Acetyl-D-glucosamine (D-GlcNAc) is a derivitized glucose monomer found in polymers of bacterial cell walls, chitin, hyaluronic acids and various glycans. D-GlcNAc is used to identify, differentiate and characterize N-acetyl-β-D-hexoaminidase(s).
包装
10 mg in autosmp vl
5, 25 g in poly bottle

Sigma Aldrich - 01140

Other Notes
Synthetic uses1,2

Toronto Research Chemicals - A178000

A pharmaceutical and cosmetic compound.