116764-15-9

Basic information

• Product Name: AVENANTHRAMIDEC
• Synonyms: AVENANTHRAMIDEC;2-{[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]amino}-5-hydroxybenzoic acid;Avenanthramide Bc;N-[3′,4′-Dihydroxy-(E)-cinnamoyl]-5-hydroxyanthranilic acid
• CAS NO: 116764-15-9
• Molecular Formula: C₁₆H₁₃NO₆
• Molecular Weight: 315.27752
• Mol File: 116764-15-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 702.3±60.0 °C(Predicted)
• Appearance: /
• Density: 1.582±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly, Heated)
• PKA: 3.37±0.36(Predicted)
• BRN: 3624543
• CAS DataBase Reference: AVENANTHRAMIDEC(CAS DataBase Reference)
• NIST Chemistry Reference: AVENANTHRAMIDEC(116764-15-9)
• EPA Substance Registry System: AVENANTHRAMIDEC(116764-15-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 116764-15-9(Hazardous Substances Data)

Usage

Uses

Avenanthramide C is an antioxidant and an anti-inflammatory agent. Avenanthramide reduces and attenuates proliferation of colonic cancer cells. Avenanthramide C inhibits chymotrypsin activity and moderately trypsin activity.

Upstream product

• 130514-71-5 2-[(E)-2-(3,4-Dihydroxy-phenyl)-vinyl]-6-hydroxy-benzo[d][1,3]oxazin-4-one 
• 331-39-5 caffeic acid 
• 88623-81-8 3,4-diacetoxycinnamic acid 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 67727-64-4 3,4-diacetoxybenzaldehyde 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Oat polyphenol avenanthramide-2c confers protection from oxidative stress by regulating the Nrf2-ARE signaling pathway in PC12 cells

Accumulating evidence has demonstrated that cellular antioxidant systems play essential roles in retarding oxidative stress-related diseases, such as Parkinson's disease. Because nuclear factor erythroid 2-related factor 2 (Nrf2) is a chief regulator of c

Key Phytochemicals Contributing to the Bitter Off-Taste of Oat (Avena sativa L.)

Sensory-directed fractionation of extracts prepared from oat flour (Avena sativa L.) followed by LC-TOF-MS, LC-MS/MS, and 1D/2D-NMR experiments revealed avenanthramides and saponins as the key phytochemicals contributing to the typical astringent and bitter off-taste of oat. Besides avenacosides A and B, two previously unreported bitter-tasting bidesmosidic saponins were identified, namely, 3-(O-α-l-rhamnopyranosyl(1→2)-[β-d-glucopyranosyl(1→3)-β-d-glucopyranosyl(1→4)]-β-d-glucopyranosid)-26-O-β-d-glucopyranosyl-(25R)-furost-5-ene-3β,22,26-triol, and 3-(O-α-l-rhamnopyranosyl(1→2)-[β-d-glucopyranosyl(1→4)]-β-d-glucopyranosid)-26-O-β-d-glucopyranosyl-(25R)-furost-5-ene-3β,22,26-triol. Depending on the chemical structure of the saponins and avenanthramides, sensory studies revealed human orosensory recognition thresholds of these phytochemicals to range between 3 and 170 μmol/L.

Induction of hydroxyanthranilate hydroxycinnamoyl transferase activity by oligo-N-acetylchitooligosaccharides in oats

An assay method for hydroxycinnamoyl-CoA: hydroxyanthranilate N- hydroxycinnamoyl transferase (HHT) in oat leaves (Avena sativa L.), which is thought to be one of the key enzymes for the biosynthesis of avenanthramides, phytoalexins in this plant, was established. HHT activity was induced by treating the leaves with oligo-N-acetylchitooligosaccharides. Among the chitooligosaccharides tested, penta-N-acetylchitopentaose ((GlcNAc)5) was the most effective in inducing activity. The induction by (GlcNAc)5 was dose-dependent, in which case HHT activity was initially detected after 6 hr and reached a maximum by 12 hr. All of the putative precursors of avenanthramides acted as substrates for HHT, with 5-hydroxyanthranilic acid and feruloyl-CoA being the best substrates for the anthranilic moiety and the cinnamoyl moiety of avenanthramides, respectively.