An N-acyl amide
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N-Oleoyl-L-phenylalanine

Item No. 28921

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(9Z)-1-oxo-9-octadecen-1-yl]-L-phenylalanine
CAS Number
136560-78-6
Synonyms
  • 18-1-Phe
  • C18:1-Phe
  • FA 18:1-Phe
Molecular Formula
C27H43NO3
Formula Weight
429.6
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 15 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 2 mg/ml
SMILES
OC([C@@H](NC(CCCCCCC/C=C\CCCCCCCC)=O)CC1=CC=CC=C1)=O
InChi Code
InChI=1S/C27H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-26(29)28-25(27(30)31)23-24-20-17-16-18-21-24/h9-10,16-18,20-21,25H,2-8,11-15,19,22-23H2,1H3,(H,28,29)(H,30,31)/b10-9-/t25-/m0/s1
InChi Key
UWKNPULCJWBBDD-JRUKXMRZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    N-Oleoyl-L-phenylalanine is an N-acyl amide.1 It increases the oxygen consumption rate (OCR) of mitochondria isolated from mouse brown adipose tissue in a Seahorse assay and decreases oligomycin-induced increases in the mitochondrial membrane potential in C2C12 cells, indicating mitochondrial uncoupling activity, when used at a concentration of 50 µM. N-Oleoyl-L-phenylalanine (30 mg/kg for eight days) reduces food intake and body weight of diet-induced obese mice.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Long, J.Z., Svensson, K.J., Bateman, L.A., et al. The secreted enzyme PM20D1 regulates lipidated amino acid uncouplers of mitochondria. Cell 166(2), 1-12 (2016).