A phenolic amide with diverse biological activities
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N-trans-Feruloyltyramine

Item No. 27459

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-2-propenamide
CAS Number
66648-43-9
Synonyms
  • Alfrutamide
  • (E)-Feruloyltyramine
  • Moupinamide
Molecular Formula
C18H19NO4
Formula Weight
313.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:3): 0.33 mg/mlEthanol: 25 mg/ml
λmax
221, 294, 320 nm
SMILES
OC1=CC=C(CCNC(/C=C/C2=CC(OC)=C(O)C=C2)=O)C=C1
InChi Code
InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+
InChi Key
NPNNKDMSXVRADT-WEVVVXLNSA-N
Origin
Plant/Aristolochia debilis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $303

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    5 mg

    $527

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    Product Description

    N-trans-Feruloyltyramine is a phenolic amide originally isolated from S. melongena that has diverse biological activities, including anti-inflammatory, antioxidative, and antiproliferative properties.1 It decreases nitric oxide (NO) production (IC50 = 17.36 µM) and inducible NO synthase (iNOS) activity and increases NO scavenging without inducing cytotoxicity in LPS-stimulated BV-2 cells.2 It also scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in TLC autographic and spectrophotometric assays.3 N-trans-Feruloyltyramine inhibits proliferation of HeLa and L929 cells by 72.2 and 22%, respectively, when used at a concentration of 30 µg/ml.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yoshihara, T., Takamatsu, S., and Sakamura, S. Three new phenolic amides from the roots of eggplant (Solanum melongena L.). Agric. Biol. Chem. 42(3), 623-627 (1978).

    2. Kim, K.H., Moon, E., Kim, H.K., et al. Phenolic constituents from the rhizomes of Acorus gramineus and their biological evaluation on antitumor and anti-inflammatory activities. Bioorg. Med. Chem. Lett. 22(19), 6155-6159 (2012).

    3. Calvin, A., Hostettmann, K., Dyatmyko, W., et al. Antioxidant and lipophilic constituents of Tinospora crispa. Planta Med. 64(5), 393-396 (1998).

    4. Fang, J.-B., Jia, W., Gao, W.-Y., et al. Antitumor constituents from Alternanthera philoxeroides. J. Asian Nat. Prod. Res. 9(6-8), 511-515 (2007).