A quinolone alkaloid with diverse biological activities
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Labeled Version(s)
90039702-Nonylquinolin-4(1H)-one-d4
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2-Nonylquinolin-4(1H)-one

Item No. 9003627

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-nonyl-4(1H)-quinolinone
CAS Number
55396-45-7
Synonyms
  • 2-n-Nonyl-4-quinolone
  • 2-Nonyl-1H-quinolin-4-one
  • 2-Nonylquinolin-4(1H)-one
  • Pseudane IX
Molecular Formula
C18H25NO
Formula Weight
271.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 15 mg/mlEthanol: 30 mg/ml
λmax
213, 236, 316, 328 nm
SMILES
O=C1C=C(CCCCCCCCC)NC2=C1C=CC=C2
InChi Code
InChI=1S/C18H25NO/c1-2-3-4-5-6-7-8-11-15-14-18(20)16-12-9-10-13-17(16)19-15/h9-10,12-14H,2-8,11H2,1H3,(H,19,20)
InChi Key
KKRXDNYRUZGPFM-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $41

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    10 mg

    $72

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    25 mg

    $157

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    50 mg

    $274

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    Product Description

    2-Nonylquinolin-4(1H)-one is a quinolone alkaloid that has been found in P. aeruginosa and has diverse biological activities.1,2,3,4 It reduces infection of Huh7.5 cells by hepatitis C virus (HCV) with an IC50 value of 1.4 µg/ml.1 2-Nonylquinolin-4(1H)-one (50 and 100 µg/ml) is also active against L. gongylophorus, a symbiotic fungus of the agricultural pest A. sexdens (leaf-cutting ant).2 It inhibits activation of nuclear factor of activated T cells (NFAT) induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) and the calcium ionophore A23187 (Item No. 11016) in Jurkat cells (IC50 = 3.44 µM), but not LPS-induced NF-κB activation in RAW 264.7 cells (IC50 = >100 µM), in reporter assays.3 This compound is expected to exist in one or both tautomeric forms, depending on experimental conditions.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wahyuni, T.S., Widyawaruyanti, A., Lusida, M.I., et al. Inhibition of hepatitis C virus replication by chalepin and pseudane IX isolated from Ruta angustifolia leaves. Fitoterapia 99, 276-283 (2014).

    2. Biavatti, M.W., Vieira, P.C., da Silva, F.d.G.F., et al. Biological activity of quinoline alkaloids from Raulinoa echinata and x-ray structure of flindersiamine. J. Braz. Chem. Soc. 13(1), 66-70 (2002).

    3. Jin, H.Z., Lee, J.H., Lee, D., et al. Quinolone alkaloids with inhibitory activity against nuclear factor of activated T cells from the fruits of Evodia rutaecarpa. Biol. Pharm. Bull. 27(6), 926-928 (2004).

    4. Ortori, C.A., Dubern, J.-F., Chhabra, S.R., et al. Simultaneous quantitative profiling of N-acyl-L-homoserine lactone and 2-alkyl-4(1H)-quinolone families of quorum-sensing signaling molecules using LC-MS/MS. Anal. Bioanal. Chem. 399(2), 839-850 (2011).