115610-32-7

Basic information

• Product Name: CINNAMYLCAFFEATE
• Synonyms: CINNAMYLCAFFEATE
• CAS NO: 115610-32-7
• Molecular Formula: C₁₈H₁₆O₄
• Molecular Weight: 296.32
• Mol File: 115610-32-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: CINNAMYLCAFFEATE(CAS DataBase Reference)
• NIST Chemistry Reference: CINNAMYLCAFFEATE(115610-32-7)
• EPA Substance Registry System: CINNAMYLCAFFEATE(115610-32-7)

Safety Data

• Hazardous Substances Data: 115610-32-7(Hazardous Substances Data)

Upstream product

• 139-85-5 3,4-dihydroxybenzaldehyde 
• 391682-55-6 carbocinnamyloxymethylenetriphenylphosporane 
• 77201-71-9 (E)-3-(3,4-dihydroxyphenyl)acryloyl chloride 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 850176-70-4 3-(3,4-bis-methoxymethoxy-phenyl)-acrylic acid 3-phenyl-allyl ester 
• 140-10-3 (E)-3-phenylacrylic acid 
• 6515-06-6 3,4-bis-methoxymethoxy-benzaldehyde 
• 331-39-5 caffeic acid 
• 82592-68-5 (E)-3,4-di-O-acetylcaffeoyl chloride 
• 88623-81-8 3,4-diacetoxycinnamic acid 
• 104023-33-8 α-chloroacetate de cinnamyle 
• 100-52-7 benzaldehyde 
• 850177-03-6 3-(3,4-bis-methoxymethoxy-phenyl)-acrylic acid ethyl ester 
• 850177-05-8 (E)-3-[3,4-bis(methoxymethoxy)phenyl]acrylic acid 

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.

Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line

Caffeic acid phenethyl ester (CAPE, 2) and its 20 analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02μM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10μg/mL towards murine colon 26-L5 carcinoma cells. Copyright