(3R)-3-(benzyloxy)tetradecanoic acid

• ChemBase ID: 161827
• Molecular Formular: C21H34O3
• Molecular Mass: 334.49286
• Monoisotopic Mass: 334.25079495
• SMILES: [C@@H](CCCCCCCCCCC)(CC(=O)O)OCc1ccccc1
• Canonical SMILES: CCCCCCCCCCC[C@H](CC(=O)O)OCc1ccccc1
• InChI: InChI=1S/C21H34O3/c1-2-3-4-5-6-7-8-9-13-16-20(17-21(22)23)24-18-19-14-11-10-12-15-19/h10-12,14-15,20H,2-9,13,16-18H2,1H3,(H,22,23)/t20-/m1/s1
• InChIKey: NDCDVTWILZGAIG-HXUWFJFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-(benzyloxy)tetradecanoic acid
• IUPAC Traditional name: (3R)-3-(benzyloxy)tetradecanoic acid
• Synonyms: (R)-3-Benzyloxytetradecanoic Acid; (3R)-3-(Phenylmethoxy)tetradecanoic Acid; (R)-3-Benzyloxy Myristic Acid

Database IDs

• CAS Number: 87357-67-3
• PubChem SID: 162255962
• PubChem CID: 11110428

CALCULATED PROPERTIES

• Acid pKa: 4.681558
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.6252213
• LogD (pH = 7.4): 3.8473625
• Log P: 6.504234
• Molar Refractivity: 98.7609 cm^3
• Polarizability: 39.156094 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ether; Ethyl Acetate
• Apperance: Light Yellow Liquid

DETAILS

Toronto Research Chemicals - B286875

One of two major component of bacterial Lipid A .

REFERENCES

• Martin, O., et al.: J. Med. Chem., 49, 6000 (2006)
• Akamatsu, M., et al.: Bioorg. Med. Chem., 14, 6759 (2006)