(3R)-3-hydroxytetradecanoic acid

• ChemBase ID: 2485
• Molecular Formular: C14H28O3
• Molecular Mass: 244.37032
• Monoisotopic Mass: 244.20384476
• SMILES: C(=O)(C[C@@H](CCCCCCCCCCC)O)O
• Canonical SMILES: CCCCCCCCCCC[C@H](CC(=O)O)O
• InChI: InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m1/s1
• InChIKey: ATRNZOYKSNPPBF-CYBMUJFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-hydroxytetradecanoic acid
• IUPAC Traditional name: (R)-3-hydroxymyristic acid; 3-hydroxy-tetradecanoic acid
• Synonyms: 3-Hydroxy-Myristic Acid; (R)-3-Hydroxytetradecanoic Acid; (3R)-3-Hydroxy-tetradecanoic Acid; D-3-Hydroxytetradecanoic Acid; (R)-3-Hydroxy Myristic Acid

Database IDs

• CAS Number: 28715-21-1
• PubChem SID: 46505492; 160965935
• PubChem CID: 5288266

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.67185
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.2492006
• LogD (pH = 7.4): 1.4713851
• Log P: 4.1366343
• Molar Refractivity: 69.3971 cm^3
• Polarizability: 27.644499 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.69
• LOG S: -3.91
• Solubility (Water): 2.99e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ether; Ethyl Acetate
• Apperance: White Powder
• Melting Point: 71-72°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB02767

Drug information: experimental

Toronto Research Chemicals - H948505

One of two major component of bacterial Lipid A .

REFERENCES

• Jenske, R., et al.: J. Agric. Food Chem., 56, 11578 (2008)
• Six, D., et al.: Biochem., 47, 8623 (2008)