ethyl (2S)-2-hydroxy-4-methylpentanoate

• ChemBase ID: 168219
• Molecular Formular: C8H16O3
• Molecular Mass: 160.21084
• Monoisotopic Mass: 160.10994437
• SMILES: C(C[C@@H](C(=O)OCC)O)(C)C
• Canonical SMILES: CCOC(=O)[C@H](CC(C)C)O
• InChI: InChI=1S/C8H16O3/c1-4-11-8(10)7(9)5-6(2)3/h6-7,9H,4-5H2,1-3H3/t7-/m0/s1
• InChIKey: QRHOWVDPHIXNEN-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-2-hydroxy-4-methylpentanoate
• IUPAC Traditional name: ethyl (2S)-2-hydroxy-4-methylpentanoate
• Synonyms: (2S)-2-Hydroxy-4-methylpentanoic Acid Ethyl Ester; Ethyl (S)-2-Hydroxyisocaproate; Ethyl L-Leucate; (S)-(-)-Ethyl Leucate

Database IDs

• CAS Number: 60856-85-1
• PubChem SID: 162262351
• PubChem CID: 13237362

CALCULATED PROPERTIES

• Acid pKa: 12.699109
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.2849826
• LogD (pH = 7.4): 1.2849804
• Log P: 1.2849827
• Molar Refractivity: 42.0311 cm^3
• Polarizability: 16.871761 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E679505

Used for the synthesis of optically active forms of Ipsenol, the pheromone of Ips bark beetles.

REFERENCES

• Mori, K., et al.: Tetrahedron, 32, 1101 (1976)