108605-70-5

Basic information

• Product Name: AVENANTHRAMIDEA
• Synonyms: AVENANTHRAMIDEA;5-Hydroxy-2-{[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid;Avenanthramide Bp;N-(4′-Hydroxy-(E)-cinnamoyl)-5-hydroxyanthranilic acid
• CAS NO: 108605-70-5
• Molecular Formula: C₁₆H₁₃NO₅
• Molecular Weight: 299.27812
• Mol File: 108605-70-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 644.7°C at 760 mmHg
• Flash Point: 343.7°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 1.68E-17mmHg at 25°C
• Refractive Index: 1.753
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility: Methanol (Slightly, Heated)
• PKA: 3.39±0.36(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: AVENANTHRAMIDEA(CAS DataBase Reference)
• NIST Chemistry Reference: AVENANTHRAMIDEA(108605-70-5)
• EPA Substance Registry System: AVENANTHRAMIDEA(108605-70-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 108605-70-5(Hazardous Substances Data)

Usage

Uses

Avenanthramide A performs a mild inhibitory activity on thrombin, trypsin, plasmin and papain. Avenanthramideis also an anti-inflammatory, antioxidant, anti-itch, anti-irritant and antiatherogenic agent.

InChI:InChI=1/C16H13NO5/c18-11-4-1-10(2-5-11)3-8-15(20)17-14-7-6-12(19)9-13(14)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-3+

Upstream product

• 7400-08-0 p-Coumaric Acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 878-00-2 4-formylphenyl acetate 
• 1882-75-3 6-acetoxy-2-methyl-4H-3,1-benzoxazin-4-one 
• 38160-63-3 4-hydroxyanthranilic acid 
• 610-30-0 2,4-dinitrobenzoic acid 
• 610-36-6 4-amino-2-nitrobenzoic acid 
• 108-24-7 acetic anhydride 
• 78183-21-8 avenalumin I diacetate 

Downstream Products

• 7400-08-0 p-Coumaric Acid 
• 78164-38-2 Avenalumin 1 

Relevant articles and documents

The Phytoalexins of Oat Leaves: 4H-3,1-Benzoxazin-4-ones or Amides?

Synthetic evidence is presented that the major phytoalexin of oat leaves is not the 4H-3,1-benzoxazin-4-one previously reported, but the corresponding amide.Other oat and carnation phytoalexins are prepared.

Synthetic method of oat alkaloids

The invention provides a synthetic method of oat alkaloid and studies a chemical synthesis process of oat alkaloids A, B and C. The oat alkaloids A, B and C are synthesized by taking 2-amino-5-hydroxybenzoic acid, meldrum's acid, 4-hydroxybenzaldehyde, 4-hydroxyl-3-methoxybenzaldehyde and 3,4-dihydroxy benzaldehyde as raw materials and using a Knoevenagel condensation reaction. Analysis means suchas infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectroscopy and elemental analysis are applied to perform structural characterization on a compound, so that the feasibility of a process route of synergizing the oat alkaloids is demonstrated, and the synthetic process conditions are optimized; the synthetic method has important research significance for further developmentof application of oat alkaloids with multiple bioactive functions such as oxidation resistance. The development of the chemical synthesis technology has a very broad application prospect.

Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships

Eight avenanthramides, amides of anthranilic acid (1) and 5-hydroxyanthranilic acid (2), respectively, and the four cinnamic acids p-coumaric (p), caffeic (c), ferulic (f), and sinapic (s) acid, were synthesized for identification in oat extracts and for structure-antioxidant activity studies. Three compounds (2p, 2c, and 2f) were found in oat extracts. As assessed by the reactivity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH), all avenanthramides except 1p showed activity. Initially, the antioxidant activity of the avenanthramides decreased in a similar order as for the corresponding cinnamic acids, that is: sinapic > caffeic > ferulic > p-coumaric acid. The avenanthramides derived from 2 were usually slightly more active than those derived from 1. All avenanthramides inhibited azo-initiated peroxidation of linoleic acid. 1c and 1s were initially the most effective compounds. The relative order of antioxidant activities was slightly different for the DPPH and the linoleic acid assays run in methanol and chlorobenzene, respectively.