83608-86-0

Basic information

• Product Name: 3-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxy-3-methoxyphenyl)ethyl)-2-propenamide
• Synonyms: 3-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxy-3-methoxyphenyl)ethyl)-2-propenamide
• CAS NO: 83608-86-0
• Molecular Formula: C₁₉H₂₁NO₅
• Molecular Weight: 343.37
• Mol File: 83608-86-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 158-160 °C
• Boiling Point: 618.9°C at 760 mmHg
• Flash Point: 328.1°C
• Appearance: /
• Density: 1.248g/cm³
• Vapor Pressure: 6.57E-16mmHg at 25°C
• Refractive Index: 1.62
• PKA: 9.78±0.35(Predicted)
• CAS DataBase Reference: 3-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxy-3-methoxyphenyl)ethyl)-2-propenamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxy-3-methoxyphenyl)ethyl)-2-propenamide(83608-86-0)
• EPA Substance Registry System: 3-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxy-3-methoxyphenyl)ethyl)-2-propenamide(83608-86-0)

Safety Data

• Hazardous Substances Data: 83608-86-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H21NO5/c1-24-17-11-13(3-6-15(17)21)5-8-19(23)20-10-9-14-4-7-16(22)18(12-14)25-2/h3-8,11-12,21-22H,9-10H2,1-2H3,(H,20,23)/b8-5+

Upstream product

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 554-52-9 3-Methoxytyramine 
• 77795-22-3 4-benzyloxy-3-methoxycinnamic acid 

Downstream Products

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 554-52-9 3-Methoxytyramine 
• 125002-90-6 Acetic acid 4-{(E)-2-[2-(4-acetoxy-3-methoxy-phenyl)-ethylcarbamoyl]-vinyl}-2-methoxy-phenyl ester 

Relevant articles and documents

Identification and quantification of potential anti-inflammatory hydroxycinnamic acid amides from wolfberry

Wolfberry or Goji berry, the fruit of Lycium barbarum, exhibits health-promoting properties that leads to an extensive study of their active components. We synthesized a set of hydroxycinnamic acid amide (HCCA) compounds, including trans-caffeic acid, trans-ferulic acid, and 3,4-dihydroxyhydrocinnamic acid, with extended phenolic amine components as standards to identify and quantify the corresponding compounds from wolfberry and to investigate anti-inflammatory properties of these compounds using in vitro model. With optimized LC-MS/MS and NMR analysis, nine amide compounds were identified from the fruits. Seven of these compounds were identified in this plant for the first time. The amide compounds with a tyramine moiety were the most abundant. In vitro studies indicated that five HCCA compounds showed inhibitory effect on NO production inuded by lipopolysaccharides with IC50 less than 15.08 μM (trans-N-feruloyl dopamine). These findings suggested that wolfberries demonstrated anti-inflammatory properties.

Synthesis of phenolic amides and evaluation of their antioxidant and anti-inflammatory activity in vitro and in vivo

A series of 15 phenolic amides (PAs) have been synthesized (PA1-PA15) and examined in vitro by four different tests: (1) prevention of Cu2+-induced human low-density lipoprotein oxidation, (2) scavenging of stable radicals, (3) anti-inflammatory activity, (4) scavenging of superoxide radicals. We used PA1 and α-tocopherol for an in vivo study. The overall potential of the antioxidant system was significantly enhanced by the PA1 and α-tocopherol supplements as the hepatic TBARS levels were lowered while the hepatic SOD activities and GSH concentration were elevated in PA1 fed rats. Our results support that PA1 may exert antioxidant action through inhibiting superoxide generation. PA1 decreased the level of nitric oxide (NO) production, tumor necrosis factor-alpha (TNF-α) and nuclear factor-kappa B (NF-κB). These results show that PA1 can inhibit lipid peroxidation, enhance the activities of antioxidant enzymes, and decrease the TNF-α/NF-κB level and nitric oxide production. Therefore, it was speculated that PA1 acts through its anti-inflammation capacity.

Two Phenolic Amides in the Seed Balls of Sugar Beet (Beta vulgaris L. var. saccharifera Alefeld)

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