N-Oleoyl Proline

• CAT Number: R066752
• CAS Number: 107432-37-1
• Molecular Formula: C23H41NO3
• Molecular Weight: 379.585
• Purity: ≥95%
• Synonyms: 1-[(9Z)-1-oxo-9-octadecen-1-yl]-L-proline
• Storage: -20°C
• IUPAC Name: (2S)-1-[(Z)-octadec-9-enoyl]pyrrolidine-2-carboxylic acid
• InChI: InChI=1S/C23H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-22(25)24-20-17-18-21(24)23(26)27/h9-10,21H,2-8,11-20H2,1H3,(H,26,27)/b10-9-/t21-/m0/s1
• InChIKey: WQCMZYCKACKLDL-YUQDSPFASA-N
• SMILES: CCCCCCCCC=CCCCCCCCC(=O)N1CCCC1C(=O)O

N-Oleoyl proline is an N-acyl amine that has been detected in bovine brain extracts and D. melanogaster larvae using mass spectrometry. In a preclinical model of pain, mice lacking fatty acid amide hydrolase (FAAH KO) had decreased N-oleoyl proline levels in lumbar spinal cord after capsaicin administration (1 µg/10 µl). N-Oleoyl proline also has surfactant properties (critical micelle concentration = 4.8 µM).

Reference

1.Tan, B.,O/’Dell, D.K.,Yu, Y.W., et al. Identification of endogenous acyl amino acids based on a targeted lipidomics approach. J. Lipid. Res. 51(1), 112-119 (2010).