96249-87-5

Basic information

• Product Name: (2E)-3-(1,3-benzodioxol-5-yl)acryloyl chloride
• Synonyms: (2E)-3-(1,3-benzodioxol-5-yl)acryloyl chloride;2-propenoyl chloride, 3-(1,3-benzodioxol-5-yl)-, (2E)-;3-(1,3-Benzodioxol-5-yl)acryloyl chloride;3-(benzo[d][1,3]dioxol-5-yl)acryloyl chloride
• CAS NO: 96249-87-5
• Molecular Formula: C₁₀H₇ClO₃
• Molecular Weight: 210.62
• Mol File: 96249-87-5.mol
• Article Data: 52

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2E)-3-(1,3-benzodioxol-5-yl)acryloyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(1,3-benzodioxol-5-yl)acryloyl chloride(96249-87-5)
• EPA Substance Registry System: (2E)-3-(1,3-benzodioxol-5-yl)acryloyl chloride(96249-87-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 96249-87-5(Hazardous Substances Data)

Upstream product

• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 120-57-0 piperonal 
• 79-37-8 oxalyl dichloride 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 2373-80-0 3,4-(methylenedioxy)cinnamic acid 

Downstream Products

• 495-86-3 trans-fagaramide 
• 57259-91-3 1-(3-benzo[1,3]dioxol-5-yl-acryloyl)-4-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-piperazine 
• 120680-81-1 2-((E)-3-Benzo[1,3]dioxol-5-yl-acryloylamino)-3-phenyl-propionic acid 
• 114133-04-9 1-(benzoyloxy)-5-<((E)-piperonylacryloyl)oxy>-1(E),3(E)-pentadiene 
• 124778-00-3 (E)-3-(benzo[d][1,3]dioxol-5-yl)-N,N-dimethylacrylamide 
• 159052-13-8 α-(3,4-methylenedioxycinnamoyl)benzylidene(triphenyl)phosphorane 
• 82857-82-7 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)prop-2-en-1-one 
• 58344-59-5 3-benzo[1,3]dioxol-5-yl-1-(2,4,6-trihydroxy-phenyl)-propenone 
• 356546-38-8 N-[(E)-3,4-methylenedioxycinnamoyl]dopamine 
• 125187-31-7 (E)-3-(benzo[d][1,3]dioxol-5-yl)-N-(3,4-dimethoxyphenethyl)acrylamide 
• 404953-16-8 (4R)-4-(diphenylmethyl)-3-[3-(3',4'-methylenedioxyphenyl)-2(E)-propenoyl]-2-oxazolidinone 
• 31983-44-5 (E)-6-[2-(benzo[1,3]dioxol-5-yl)vinyl]pyran-2-one 

Relevant articles and documents

Design, synthesis, and taste evaluation of a high-intensity umami-imparting oxazole-based compound

Umami taste is imparted predominantly by monosodium glutamate (MSG) and 5′-ribonucleotides. Recently, several different classes of hydrophobic umami-imparting compounds, the structures of which are quite different from MSG, have been reported. To obtain a novel umami-imparting compound, N-cinnamoyl phenethylamine was chosen as the lead compound, and a rational structure-optimization study was conducted on the basis of the pharmacophore model of previously reported compounds. The extremely potent umami-imparting compound 2-[[[2-[(1E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-oxazolyle]methoxy]methyl]pyridine, which exhibits 27,000 times the umami taste of MSG, was found. Its terminal pyridine residue and linear structure are suggested to be responsible for its strong activity. The time taken to reach maximum taste intensity exhibited by it, as determined by the time-intensity method, is 22.0 s, whereas the maximum taste intensity of MSG occurs immediately. This distinct difference in the time-course taste profile may be due to the hydrophobicity and strong receptor affinity of the new compound.

Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum

Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.

Design, synthesis and biological evaluation of novel carboline-cinnamic acid hybrids as multifunctional agents for treatment of Alzheimer's disease

Alzheimer's disease (AD) is a complex neurodegenerative disease with multiple pathological features. Multifunctional compounds able to simultaneously interact with several pathological components have been considered as a solution to treat the complex pathologies of neurodegenerative diseases. β-carboline and cinnamic acid have been extensively studied for their widespread biological effects in treatment of AD, further application is limited due to its poor solubility and high toxicity. Herein, a series of carboline-cinnamic acid hybrids was designed and synthesized to obtain new multifunctional molecules with low toxicity and good physicochemical properties. In particular, e3 and e12 exhibited significant inhibition of Aβ aggregation (inhibitory rate at 25 μM: 65% and 72% respectively), moderate BuChE inhibition, excellent neuroprotective effects and low neurotoxicity. Furthermore, in the AD mice model, e3 and e12 could restore learning and memory function to a comparable level to that of the control and did not exhibit any acute toxicity in vivo at a relatively high dose of 600 mg/kg. Thus, these new compounds can be further studied as multifunctional molecules for AD.