ethyl (2R,3R,4E)-2-amino-3-hydroxytetradec-4-enoate

• ChemBase ID: 160196
• Molecular Formular: C16H31NO3
• Molecular Mass: 285.42224
• Monoisotopic Mass: 285.23039386
• SMILES: C(CCCCCCC/C=C/[C@H]([C@H](C(=O)OCC)N)O)C
• Canonical SMILES: CCCCCCCCC/C=C/[C@H]([C@H](C(=O)OCC)N)O
• InChI: InChI=1S/C16H31NO3/c1-3-5-6-7-8-9-10-11-12-13-14(18)15(17)16(19)20-4-2/h12-15,18H,3-11,17H2,1-2H3/b13-12+/t14-,15-/m1/s1
• InChIKey: KLGSSMZKPJPOGR-MSIAHBHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R,3R,4E)-2-amino-3-hydroxytetradec-4-enoate
• IUPAC Traditional name: ethyl (2R,3R,4E)-2-amino-3-hydroxytetradec-4-enoate
• Synonyms: (2S,3R,4E)-2-Amino-3-hydroxy-4-tetradecen-1-carboxylate; (2S,3R,4E)-2-Amino-3-hydroxy-tetradecenoic Acid Ethyl Ester

Database IDs

• PubChem SID: 162254331
• PubChem CID: 71313276

CALCULATED PROPERTIES

• Acid pKa: 13.982874
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.2711592
• LogD (pH = 7.4): 3.5081491
• Log P: 3.6112819
• Molar Refractivity: 82.8731 cm^3
• Polarizability: 32.866657 Å^3
• Polar Surface Area: 72.55 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - A611670

Intermediate in the preparation of sphingosine bases and derivatives.