28010-23-3

Basic information

• Product Name: (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid
• Synonyms: (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid
• CAS NO: 28010-23-3
• Molecular Weight: 264.278
• Mol File: 28010-23-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid(28010-23-3)
• EPA Substance Registry System: (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid(28010-23-3)

Safety Data

• Hazardous Substances Data: 28010-23-3(Hazardous Substances Data)

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 101620-05-7 (2E,4E)-5-(3,4,5-Trimethoxy-phenyl)-penta-2,4-dienoic acid ethyl ester 
• 71277-13-9 3,4,5-trimethoxycinnamaldehyde 
• 36266-40-7 1-(3,4,5-trimethoxyhenyl)ethanol 

Downstream Products

• 206535-00-4 2,6-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoylamino]pyridine 
• 206534-99-8 3,4-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoylamino]pyridine 
• 206534-98-7 2,3-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoylamino]pyridine 

Relevant articles and documents

Structure-activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities

Inhibitors of drug metabolism have important implications in pharmaco- toxicology and agriculture. We have reported earlier that piperine, a major alkaloid of black and long peppers inhibits both constitutive and inducible cytochrome P450 (CYP)-dependent drug metabolising enzymes. In the present study, an attempt has been made to prepare several novel synthetic analogues so as to relate various modifications in the parent molecule to the inhibition of CYP activities. Two types of mono-oxygenase reactions arylhydrocarbon hydroxylase (AHH) and 7-methoxycoumarin-O-demethylase (MOCD) have been studied. Inhibition studies were investigated in rat microsomal fraction prepared from untreated, 3MC- and PB- treated rat liver in vitro. Modifications were introduced into the piperine molecule: (i) in the phenyl nucleus, (ii) in the side chain and (iii) in the basic moiety. Thus, 38 compounds have been subjected to such studies, and simultaneously an attempt has also been made to arrive at the structure-activity relationship of synthetic analogues. In general, most of the inhibitory potential of the parent molecule is lost with modification in either of the three components of piperine. Saturation of the side chain resulted in significantly enhanced inhibition of CYP while modifications in the phenyl and basic moieties in few analogues offered maximal selectivity in inhibiting either constitutive or inducible CYP activities. Thus few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs. (C) 2000 Elsevier Science Ltd.

(2E,4E)-N-(4-(1H-indol-3-yl)piperidin-1-yl)alkyl-5-(substituted phenyl)-2,4-pentadienamides as antiallergic agents with antihistaminic and anti slow-reacting substance (SRS) activities

As an extension of our study aiming to discover a novel compound with dual activities against histamine and slow-reacting substance (SRS), we synthesized two types of indolylpiperidine derivatives, 3 and 4-20. Testing for in vivo antianaphylactic activity and for in vitro anti-SRS activity revealed that (2E,4E)-5-(3,5-dimethoxy-4-hydroxyphenyl)-N-(2-(4-(1H-indol-3-yl)piper idin-1-yl)ethyl)-2,4-pentadienamide (11) exhibited potent dual activities with ED50 = 0.89 mg/kg and IC50 = 1.43 μM, respectively. However, the plasma concentration of unchanged 11 was very low when administered orally in guinea pigs. This result can be explained by fast formation of a glucuronic acid conjugate.