[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl N-heptylcarbamate

• ChemBase ID: 131352
• Molecular Formular: C15H29NO7
• Molecular Mass: 335.39326
• Monoisotopic Mass: 335.19440227
• SMILES: CCCCCCCNC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC)O)O)O
• Canonical SMILES: CCCCCCCNC(=O)OC[C@H]1O[C@H](OC)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H29NO7/c1-3-4-5-6-7-8-16-15(20)22-9-10-11(17)12(18)13(19)14(21-2)23-10/h10-14,17-19H,3-9H2,1-2H3,(H,16,20)/t10-,11-,12+,13-,14+/m1/s1
• InChIKey: XPIVOYOQXKNYHA-RGDJUOJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl N-heptylcarbamate
• IUPAC Traditional name: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl N-heptylcarbamate
• Synonyms: 6-O-(N-Heptylcarbamoyl)-methyl-α-D-glucopyranoside; HECAMEG; Methyl 6-O-(N-heptylcarbamoyl)-α-D-glucopyranoside

Database IDs

• CAS Number: 115457-83-5
• MDL Number: MFCD00077425
• Beilstein Number: 3560078
• PubChem SID: 162225630; 24885153
• PubChem CID: 2733955

CALCULATED PROPERTIES

• LogD (pH = 7.4): 0.69944155
• Log P: 0.6994482
• Molar Refractivity: 81.0761 cm^3
• Polarizability: 32.92647 Å^3
• Polar Surface Area: 117.48 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true
• Acid pKa: 12.212818
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.69944817

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL, clear, colorless
• Optical Rotation: [α]20/D +101°
• Critical Micelle Concentration: 19.5

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥90% (TLC); ≥97.0% (TLC)
• Description: non-ionic
• Cation Traces: Ca: ≤50 mg/kg; Cd: ≤50 mg/kg; Co: ≤50 mg/kg; Cr: ≤50 mg/kg; Cu: ≤50 mg/kg; Fe: ≤50 mg/kg; K: ≤100 mg/kg; Mg: ≤50 mg/kg; Mn: ≤50 mg/kg; Na: ≤1000 mg/kg; Ni: ≤50 mg/kg; Pb: ≤50 mg/kg; Zn: ≤50 mg/kg
• Empirical Formula (Hill Notation): C15H29NO7

DETAILS

Sigma Aldrich - 67328

Other Notes
Very mild surfactant, useful for membrane protein studies1

Sigma Aldrich - M3420

Application
Non-ionic detergent with superior properties: dissociates protein aggregates but does not denature enzymes or antigens; high CMC (19.5 mM) allow fast removal by dialysis.