An endogenous N-acyl amine
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Linoleoyl Phenylalanine

Item No. 20063

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(9Z,12Z)-1-oxo-9,12-octadecadien-1-yl]-L-phenylalanine
CAS Number
2441-64-7
Synonyms
  • N-Linoleoyl Phenylalanine
Molecular Formula
C27H41NO3
Formula Weight
427.6
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 15 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 2 mg/ml
λmax
262, 379 nm
SMILES
CCCCC/C=C\C/C=C\CCCCCCCC(N[C@@H](CC1=CC=CC=C1)C(O)=O)=O
InChi Code
InChI=1S/C27H41NO3/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/h6-7,9-10,16-18,20-21,25H,2-5,8,11-15,19,22-23H2,1H3,(H,28,29)(H,30,31)/b7-6-,10-9-/t25-/m0/s1
InChi Key
HKUGGWURERXWKM-ABDCMALPSA-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-Linoleoyl phenylalanine is an endogenous N-acyl amine found in D. melanogaster larvae.1 N-acyl amines have been shown to have anti-inflammatory action that can be monitored using 15-deoxy-prostaglandin J2 (PGJ2) quantification.2,3 N-Linoleoyl phenylalanine does not increase PGJ2 expression in RAW cells, indicating lack of an anti-inflammatory action.3 N-acyl amines also promote mitochondrial uncoupling.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Dennis, E.A., and Norris, P.C. Eicosanoid storm in infection and inflammation. Nat. Rev. Immunol. 15(8), 511-523 (2015).

    3. Burstein, S., McQuain, C., Salmonsen, R., et al. N-Amino acid linoleoyl conjugates: Anti-inflammatory activities. Bioorg. Med. Chem. Lett. 22(2), 872-875 (2012).

    4. 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).