108605-69-2

Basic information

• Product Name: Benzoic acid,5-hydroxy-2-[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]amino]-
• Synonyms: Benzoicacid, 5-hydroxy-2-[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino]-(9CI); Benzoic acid,5-hydroxy-2-[[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino]-, (E)-;Avenanthramide 1; Avenanthramide 2f; Avenanthramide B; Avenanthramide Bf
• CAS NO: 108605-69-2
• Molecular Formula: C17H15 N O6
• Molecular Weight: 329.309
• Mol File: 108605-69-2.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid,5-hydroxy-2-[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid,5-hydroxy-2-[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]amino]-(108605-69-2)
• EPA Substance Registry System: Benzoic acid,5-hydroxy-2-[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]amino]-(108605-69-2)

Safety Data

• Hazardous Substances Data: 108605-69-2(Hazardous Substances Data)

Upstream product

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 
• 121-33-5 vanillin 
• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 881-68-5 vanillin acetate 
• 108-24-7 acetic anhydride 

Relevant articles and documents

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.

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.

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.

Preparation method of avenanthramide and derivative thereof

The invention provides a preparation method of avenanthramide and a derivative thereof. The avenanthramide and the derivative thereof are synthesized and obtained by mainly utilizing an organic acid and aminobenzoic acid as major reactants. The method is