ethyl (2R,3R,4E)-2-amino-3-hydroxy(1,2-13C2)octadec-4-enoate

• ChemBase ID: 168397
• Molecular Formular: C20H39NO3
• Molecular Mass: 343.51386968
• Monoisotopic Mass: 343.29970379
• SMILES: [C@H](/C=C/CCCCCCCCCCCCC)(O)[13C@H]([13C](=O)OCC)N
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([13C@H]([13C](=O)OCC)N)O
• InChI: InChI=1S/C20H39NO3/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18(22)19(21)20(23)24-4-2/h16-19,22H,3-15,21H2,1-2H3/b17-16+/t18-,19-/m1/s1/i19+1,20+1
• InChIKey: WZDBTOQQJCFLPW-ITDIHFBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R,3R,4E)-2-amino-3-hydroxy(1,2-^1^3C₂)octadec-4-enoate
• IUPAC Traditional name: ethyl (2R,3R,4E)-2-amino-3-hydroxy(1,2-^1^3C₂)octadec-4-enoate
• Synonyms: (2R,3R,4E)-2-Amino-3-hydroxy-4-octadecenoic Acid Ethyl Ester; [R-[R*,R*-(E)]]-2-Amino-3-hydroxy-4-octadecenoic Acid Ethyl Ester; Ethyl (2R,3R,4E)-2-Amino-3-hydroxy-4-octadecenoate-13C2

Database IDs

• PubChem SID: 162262529
• PubChem CID: 45039181

CALCULATED PROPERTIES

• Acid pKa: 13.982874
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.0494337
• LogD (pH = 7.4): 5.2864237
• Log P: 5.3895564
• Molar Refractivity: 101.2771 cm^3
• Polarizability: 40.238968 Å^3
• Polar Surface Area: 72.55 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - E898317

Labelled Ethyl (2R,3R,4E)-2-Amino-3-hydroxy-4-octadecenoate is used in total synthesis of stereospecific sphingosine and ceramide.

REFERENCES

• Shoyama, Y., et al.: J. Lipid Res.,19, 250 (1978)