(4S)-5-(acetyloxy)-4-methylpentanoic acid

• ChemBase ID: 159038
• Molecular Formular: C8H14O4
• Molecular Mass: 174.19436
• Monoisotopic Mass: 174.08920893
• SMILES: C(C[C@@H](COC(=O)C)C)C(=O)O
• Canonical SMILES: C[C@H](COC(=O)C)CCC(=O)O
• InChI: InChI=1S/C8H14O4/c1-6(3-4-8(10)11)5-12-7(2)9/h6H,3-5H2,1-2H3,(H,10,11)/t6-/m0/s1
• InChIKey: OCLVCORVKBNFRN-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-5-(acetyloxy)-4-methylpentanoic acid
• IUPAC Traditional name: (4S)-5-(acetyloxy)-4-methylpentanoic acid
• Synonyms: (S)-5-(Acetyloxy)-4-methylpentanoic Acid; (S)-5-Acetoxy-4-methylpentanoic Acid

Database IDs

• PubChem SID: 162253173
• PubChem CID: 13963105

CALCULATED PROPERTIES

• Acid pKa: 4.4514213
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.3485931
• LogD (pH = 7.4): -2.1120927
• Log P: 0.7357471
• Molar Refractivity: 42.0244 cm^3
• Polarizability: 16.831173 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A167540

The (S)-intermediate in the synthesis of (4R,8R)-4,8-Dimethyldecanal, the pheromone of flour beetles.

REFERENCES

• Czeskis, B.A., et al.: Mendeleev Communications, 3, 93 (1993)