37620-38-5

Basic information

• Product Name: (2E)-3-(1,3-benzodioxol-5-yl)-1-(4-methylphenyl)prop-2-en-1-one
• CAS NO: 37620-38-5
• Molecular Formula: C₁₇H₁₄O₃
• Molecular Weight: 266.2913
• Mol File: 37620-38-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 434°C at 760 mmHg
• Flash Point: 208.1°C
• Density: 1.225g/cm³
• Vapor Pressure: 9.8E-08mmHg at 25°C
• Refractive Index: 1.638
• CAS DataBase Reference: (2E)-3-(1,3-benzodioxol-5-yl)-1-(4-methylphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(1,3-benzodioxol-5-yl)-1-(4-methylphenyl)prop-2-en-1-one(37620-38-5)
• EPA Substance Registry System: (2E)-3-(1,3-benzodioxol-5-yl)-1-(4-methylphenyl)prop-2-en-1-one(37620-38-5)

Safety Data

• Hazardous Substances Data: 37620-38-5(Hazardous Substances Data)

Usage

General Description

The chemical compound (2E)-3-(1,3-benzodioxol-5-yl)-1-(4-methylphenyl)prop-2-en-1-one, also known as safrole, is a colorless or slightly yellow oily liquid with a sweet, spicy odor. It is commonly used in the production of perfumes and soaps, as well as in the synthesis of other chemicals. However, it is also a precursor to the illegal drug MDMA (ecstasy) and has been classified as a controlled substance in many countries due to its potential for abuse. Safrole has been found to have carcinogenic effects in animal studies and may also have harmful effects on the liver and kidneys. As a result, its use and production are heavily regulated to minimize the risks to human health and the environment.

Upstream product

• 120-57-0 piperonal 
• 122-00-9 para-methylacetophenone 
• 495-76-1 piperonol 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 766-97-2 4-n-methylphenylacetylene 
• 1443526-81-5 1-(benzo[d][1,3]dioxol-5-yl)-3-(p-tolyl)prop-2-yn-1-ol 
• 1417658-61-7 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 
• 64376-20-1 3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-1-(4-methoxy-phenyl)-propenone 
• 29668-44-8 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 619-41-0 4-(bromoacetyl)toluene 

Downstream Products

• 84857-19-2 4-Benzo[1,3]dioxol-5-yl-6-p-tolyl-pyrimidin-2-ylamine 
• 76287-99-5 5-benzo[1,3]dioxol-5-yl-3-p-tolyl-isoxazole 
• 76287-93-9 5-Benzo[1,3]dioxol-5-yl-3-p-tolyl-4,5-dihydro-isoxazole 
• 1197386-06-3 2-(p-tolylthio)-4-(benzo[d][1,3]dioxol-6-yl)-6-p-tolylpyridine-3-carbonitrile 
• 1443527-35-2 3-(benzo[d][1,3]dioxol-5-yl)-1,3-di-p-tolylpropan-1-one 
• 1443527-10-3 (S)-3-(benzo[d][1,3]dioxol-5-yl)-1,3-di-p-tolylpropan-1-one 
• 1465270-12-5 C₂₀H₁₆O₂ 
• 1465270-30-7 C₂₇H₂₂O₄S 
• 73910-88-0 4-benzo[1,3]dioxol-5-yl-2-(3-nitro-phenyl)-6-p-tolyl-pyridine 
• 73910-94-8 4-benzo[1,3]dioxol-5-yl-2-(4-chloro-phenyl)-6-p-tolyl-pyridine 
• 1376396-17-6 5-(benzo[d][1,3]dioxol-5-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 

Relevant articles and documents

Dihydropyrazole derivatives containing benzo oxygen heterocycle and sulfonamide moieties selectively and potently inhibit COX-2: Design, synthesis, and anti-colon cancer activity evaluation

Cyclooxygenase-2 (COX-2) as a rate-limiting metabolism enzyme of arachidonic acid has been found to be implicated in tumor occurrence, angiogenesis, metastasis as well as apoptosis inhibition, regarded as an attractive therapeutic target for cancer therapy. In our research, a series of dihydropyrazole derivatives containing benzo oxygen heterocycle and sulfonamide moieties were designed as highly potent and selective COX-2 inhibitors by computer-aided drug analysis of known COX-2 inhibitors. A total of 26 compounds were synthesized and evaluated COX-2 inhibition and pharmacological efficiency both in vitro and in vivo with multi-angle of view. Among them, compound 4b exhibited most excellent anti-proliferation activities against SW620 cells with IC50 of 0.86 ± 0.02 μM than Celecoxib (IC50 = 1.29 ± 0.04 μM). The results favored our rational design intention and provides compound 4b as an effective COX-2 inhibitor available for the development of colon tumor therapeutics.

Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach

Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.

One-pot synthesis of multifunctionalized cyclopropanes

A facile one-step synthetic protocol toward multifunctionalized cyclopropanes 4 is developed from substituted chalcones 1 and sulfones 2 in good yields via a [2C+1C] annulation.