A phenolic alkaloid with diverse biological activities
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Parent Compound(s)
13044Tranilast46383Tranilast (sodium salt)
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Avenanthramide E

Item No. 46547

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]amino]-benzoic acid
CAS Number
93755-77-2
Synonyms
  • Avenanthramide 1f
  • AVN-E
Molecular Formula
C17H15NO5
Formula Weight
313.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥10 mg/ml
SMILES
OC(C1=C(C=CC=C1)NC(/C=C/C2=CC(OC)=C(C=C2)O)=O)=O
InChi Code
InChI=1S/C17H15NO5/c1-23-15-10-11(6-8-14(15)19)7-9-16(20)18-13-5-3-2-4-12(13)17(21)22/h2-10,19H,1H3,(H,18,20)(H,21,22)/b9-7+
InChi Key
FSKJPXSYWQUVGO-VQHVLOKHSA-N
Origin
Plant/Oat
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $25

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    5 mg

    $119

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    10 mg

    $200

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    25 mg

    $313

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    Product Description

    Avenanthramide E is a phenolic alkaloid that has been found in A. sativa and has diverse biological activities.1,2,3,4,5 It is also an active metabolite of the antiallergic agent tranilast (Item Nos. 13044 | 46383).6 Avenanthramide E reduces lipid peroxidation in a cell-free assay at 40 µM, scavenges DPPH (Item No. 14805) radicals in a cell-free assay, reduces ferric to ferrous iron in a ferric reducing antioxidant power (FRAP) assay, and inhibits hydrogen peroxide-induced DNA damage in HT-29 cells (EC50 = 1.1 µM).2,3 It inhibits the replication of monkeypox virus in infected Vero cells (EC50 = 8.1 µM).4 Avenanthramide E (100 µM) also inhibits TGF-β-induced collagen production by 50% in cultured renal mesangial cells.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Collins, F.W. Oat phenolics: Avenanthramides, novel substituted N-cinnamoylanthranilate alkaloids from oat groats and hulls. J. Agric. Food Chem. 37(1), 60-66 (2002).

    2. Bratt, K., Sunnerheim, K., Bryngelsson, S., et al. Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships. J. Agric. Food Chem. 51(3), 594-600 (2003).

    3. Lee-Manion, A.M., Price, R.K., Strain, J.J., et al. In vitro antioxidant activity and antigenotoxic effects of avenanthramides and related compounds. J. Agric. Food Chem. 57(22), 10619-10624 (2009).

    4. Ni, Y., Liu, F., Ma, X., et al. Structural modification of tranilast against poxvirus based on α, β-unsaturated acrylamide covalent warhead and confirmation of the targets and mode of action. J. Med. Chem. 69(10), 12307-12323 (2026).

    5. Zammit, S.C., Cox, A.J., Gow, R.M., et al. Evaluation and optimization of antifibrotic activity of cinnamoyl anthranilates. Bioorg. Med. Chem. Lett. 19(24), 7003-7006 (2009).

    6. Slobodzian, D.K., Hsieh, J.Y., and Bayne, W.F. Simultaneous determination of tranilast and metabolites in plasma and urine using high-performance liquid chromatography. J. Chromatogr. 345(2), 345-354 (1985).