An endogenous N-acyl amine
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N-Oleoyl Proline

Item No. 20369

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[(9Z)-1-oxo-9-octadecen-1-yl]-L-proline
CAS Number
107432-37-1
Molecular Formula
C23H41NO3
Formula Weight
379.6
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 12 mg/mlEthanol: 12 mg/mlEthanol:PBS (pH 7.2) (1:4): 200 µg/ml
SMILES
CCCCCCCC/C=C\CCCCCCCC(N1CCC[C@H]1C(O)=O)=O
InChi Code
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
InChi Key
WQCMZYCKACKLDL-YUQDSPFASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $178

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    10 mg

    $312

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    25 mg

    $680

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    Product Description

    N-Oleoyl proline is an N-acyl amine that has been detected in bovine brain extracts and D. melanogaster larvae using mass spectrometry.1,2 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).3 N-Oleoyl proline also has surfactant properties (critical micelle concentration = 4.8 µM).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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).

    2. Tortoriello, G., Rhodes, B.P., Takacs, S.M., et al. Targeted lipidomics in Drosophila melanogaster identifies novel 2-monoacylglycerols and N-acyl amides. PLoS One 8(7), e67865 (2013).

    3. Carey, L.M., Slivicki, R.A., Leishman, E., et al. A pro-nociceptive phenotype unmasked in mice lacking fatty-acid amide hydrolase. Mol. Pain 12, (2016).

    4. Sreenu, M., Nayak, R.R., Prasad, R.B.N., et al. Synthesis, surface and micellar properties of sodium N-oleoyl amino acids. Colloids Surf. A. Physicochem. Eng. Aspects 449, 74-81 (2014).