133045-55-3

Basic information

• Product Name: (E)-1-(3,4-dihydroxyphenyl)-6-phenyl-hex-1-en-3-one
• Synonyms: (E)-1-(3,4-dihydroxyphenyl)-6-phenyl-hex-1-en-3-one
• CAS NO: 133045-55-3
• Molecular Weight: 282.339
• Mol File: 133045-55-3.mol

Chemical Properties

• CAS DataBase Reference: (E)-1-(3,4-dihydroxyphenyl)-6-phenyl-hex-1-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(3,4-dihydroxyphenyl)-6-phenyl-hex-1-en-3-one(133045-55-3)
• EPA Substance Registry System: (E)-1-(3,4-dihydroxyphenyl)-6-phenyl-hex-1-en-3-one(133045-55-3)

Safety Data

• Hazardous Substances Data: 133045-55-3(Hazardous Substances Data)

Upstream product

• 637-59-2 1-Bromo-3-phenylpropane 
• 331-39-5 caffeic acid 
• 2235-83-8 5-phenyl-2-pentanone 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 10521-97-8 5-phenyl-pent-3-en-2-one 

Downstream Products

• 1443545-68-3 acetic acid (E)-2-acetoxy-5-(3-oxo-6-phenyl-hex-1-enyl)phenyl ester 

Relevant articles and documents

Structure–activity relationship of caffeic acid phenethyl ester analogs as new 5-lipoxygenase inhibitors

Leukotrienes (LTs) are a class of lipid mediators implicated in numerous inflammatory disorders. Caffeic acid phenethyl ester (CAPE) possesses potent anti-LTs activity through the inhibition of 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of LTs. In this study, we describe the design and synthesis of CAPE analogs as radical scavengers and 5-LO inhibitors. Caffeic esters bearing propargyl and allyl linkers between the caffeoyl and aryl moieties (4a–i and 5a–i, respectively) were synthesized by Sonogashira and Heck cross-coupling reactions to probe the effects of flexibility and aryl substitution on 5-LO inhibition. Caffeoyl alcohol and ethers (6, 7a–b) as well as caffeoyl aldehyde and ketones (8a–e) were synthesized to elucidate the importance of the ester linkage for inhibitory activity. All tested compounds proved to be good radical scavengers (IC50 of 10–30?μm). After preliminary anti-LTs activity screening in HEK293 cell models, 5-LO inhibition potential of selected compounds was determined in human polymorphonuclear leukocytes (PMNL). Most screened compounds outperformed CAPE 3 in concentration-dependent assays on PMNL, with ester dimers 4i and 5i along with caffeoyl ethers 7a–b being roughly eight-, seven-, and 16-fold more potent than Zileuton, with IC50 values of 0.36, 0.43, and 0.18?μm, respectively.

Synthesis and neuroprotective effect of E-3,4-dihydroxy styryl aralkyl ketones derivatives against oxidative stress and inflammation

E-3,4-Dihydroxy styryl aralkyl ketones as well as their 3,4-diacetylated derivatives as the analogues of neuroprotective agent CAPE were designed and synthesized for improving stability and lipid solubility. The neuroprotective activities of target compounds 10a-g and 11a-g were tested by three models in vitro, including 1,1-diphenyl-2-picrylhydrazyl radical scavenging capacity, neuronal protecting effect against damage induced by H2O2 in PC12 cells and nitric oxide suppression effect in BV2 microglial cells. The results demonstrated that compounds 10f and 11f exhibited the most potent neuroprotective effect against oxidative stress and inflammation, which is higher than that of the lead compound CAPE.