(2R,3R,4R,5S)-1-dodecyl-2-(hydroxymethyl)piperidine-3,4,5-triol

• ChemBase ID: 153930
• Molecular Formular: C18H37NO4
• Molecular Mass: 331.49068
• Monoisotopic Mass: 331.27225867
• SMILES: CCCCCCCCCCCCN1C[C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O
• Canonical SMILES: CCCCCCCCCCCCN1C[C@H](O)[C@H]([C@@H]([C@H]1CO)O)O
• InChI: InChI=1S/C18H37NO4/c1-2-3-4-5-6-7-8-9-10-11-12-19-13-16(21)18(23)17(22)15(19)14-20/h15-18,20-23H,2-14H2,1H3/t15-,16+,17-,18-/m1/s1
• InChIKey: TYXAKMAAZJJHCB-XMTFNYHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S)-1-dodecyl-2-(hydroxymethyl)piperidine-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4R,5S)-1-dodecyl-2-(hydroxymethyl)piperidine-3,4,5-triol
• Synonyms: N-Dodecyl-1-deoxynojirimycin

Database IDs

• CAS Number: 79206-22-7
• MDL Number: MFCD11045272
• PubChem SID: 162248069
• PubChem CID: 9818954

CALCULATED PROPERTIES

• Acid pKa: 12.902188
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -0.39818886
• LogD (pH = 7.4): 1.3686355
• Log P: 2.377753
• Molar Refractivity: 92.5507 cm^3
• Polarizability: 37.161064 Å^3
• Polar Surface Area: 84.16 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C18H37NO4

DETAILS

Sigma Aldrich - 63971

Application
N-Dodecyl-1-deoxynojirimycin is used as an inhibitor of glucan synthesis at the level of glucosyltransferase (GTF-I) and related glucosidases. N-Dodecyl-1-deoxynojirimycin is used as an inhibitor of glucocerebrosidase(s).