18110-26-4

Basic information

• Product Name: 2-[(4-ETHOXYPHENOXY)METHYL]OXIRANE
• Synonyms: Oxirane,2-[(4-ethoxyphenoxy)Methyl]-
• CAS NO: 18110-26-4
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• Mol File: 18110-26-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 302.7°Cat760mmHg
• Flash Point: 100.8°C
• Appearance: /
• Density: 1.114g/cm³
• Vapor Pressure: 0.00174mmHg at 25°C
• Refractive Index: 1.521
• CAS DataBase Reference: 2-[(4-ETHOXYPHENOXY)METHYL]OXIRANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-ETHOXYPHENOXY)METHYL]OXIRANE(18110-26-4)
• EPA Substance Registry System: 2-[(4-ETHOXYPHENOXY)METHYL]OXIRANE(18110-26-4)

Safety Data

• Hazardous Substances Data: 18110-26-4(Hazardous Substances Data)

Usage

Structure

Contains a three-membered oxirane ring (consisting of one oxygen and two carbon atoms) and a 4-ethoxyphenoxy group attached to a methyl group.

Classification

Organic epoxide

Usage

Reactive diluent in epoxy resin production, cross-linking agent in polymer synthesis, building block for creating other chemical compounds.

Safety precautions

Handle with care and take appropriate protective measures.

InChI:InChI=1/C11H14O3/c1-2-12-9-3-5-10(6-4-9)13-7-11-8-14-11/h3-6,11H,2,7-8H2,1H3

Upstream product

• 622-62-8 4-Ethoxyphenol 
• 106-89-8 epichlorohydrin 
• 123-31-9 hydroquinone 
• 103-16-2 4-Benzyloxyphenol 
• 69697-44-5 4-ethoxyphenyl benzyl ether 
• 3132-64-7 1,2-Epoxy-3-bromopropane 

Downstream Products

• 956507-49-6 1-(((1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)methyl) (methyl)amino)-3-(4-ethoxyphenoxy)propan-2-ol 
• 1227743-95-4 (R)-2-((4-ethoxyphenoxy)methyl)oxirane 
• 1280193-99-8 N-((1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-methyl)-3-(4-ethoxyphenoxy)-2-methoxy-N-methylpropan-1-amine 
• 1280194-01-5 1-(((1-benzyl-3,5-dimethyl-1H-pyrazol-4-yl)methyl)(methyl)amino)-3-(4-ethoxyphenoxy)propan-2-ol 
• 1311146-77-6 1-(((1-(3-chlorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)methyl)(methyl)amino)-3-(4-ethoxyphenoxy)propan-2-ol 
• 1311146-78-7 1-(((1-(3,4-dichlorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)methyl)(methyl)amino)-3-(4-ethoxyphenoxy)propan-2-ol 
• 1280193-98-7 1-(((3,5-dimethyl-1-(2-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)methyl)(methyl)amino)-3-(4-ethoxyphenoxy)propan-2-ol 
• 1280193-90-9 1-(((3,5-dimethyl-1-(2-vinylbenzyl)-1H-pyrazol-4-yl)methyl)(methyl)amino)-3-(4-ethoxyphenoxy)propan-2-ol 
• 1227743-94-3 (R)-1-(((1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)methyl)(methyl)amino)-3-(4-ethoxyphenoxy)propan-2-ol 
• 1227743-93-2 (S)-1-(((1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)methyl)(methyl)amino)-3-(4-ethoxyphenoxy)propan-2-ol 

Relevant articles and documents

Discovery of novel small molecule TLR4 inhibitors as potent anti-inflammatory agents

Toll-like receptor 4 (TLR4) initiates innate immune response to release inflammatory cytokines and has been pathologically linked to variety of inflammatory diseases. Recently, we found that Carvedilol, as the classic anti-heart failure and anti-inflammatory clinic drug, could inhibit the TLR4 signaling in the TLR4 overexpressed cells. Herein, we have designed and synthesized a small library of novel Carvedilol derivatives and investigated their potential inhibitory activity. The results indicate that the most potent compound 8a (SMU-XY3) could effectively inhibited TLR4 protein and the LPS triggered alkaline phosphatase signaling in HEK-Blue hTLR4 cells. It down regulated the nitric oxide (NO) in both RAW264.7 cells and BV-2 microglial cells, in addition to blocking the TNF-α signaling in ex-vivo human peripheral blood mononuclear cells (PBMC). More interestingly, 8a shows higher affinity to hyperpolarization-activated cyclic nucleotide-gated 4 (HCN4) over HCN2, which probably indicates the new application of TLR4 inhibitor 8a in heart failure, coronary heart disease, and other inflammatory diseases.

Development of β-amino alcohol derivatives that inhibit toll-like receptor 4 mediated inflammatory response as potential antiseptics

Toll-like receptor 4 (TLR4) induced proinflammatory signaling has been directly implicated in severe sepsis and represents an attractive therapeutic target. Herein, we report our investigations into the structure-activity relationship and preliminary drug metabolism/pharmacokinetics study of β-amino alcohol derivatives that inhibit the TLR4 signaling pathway. Lead compounds were identified from in vitro cellular examination with micromolar potency for their inhibitory effects on TLR4 signaling and subsequently assessed for their ability to suppress the TLR4-induced inflammatory response in an ex vivo whole blood model. In addition, the toxicology, specificity, solubility, brain-blood barrier permeability, and drug metabolism of several compounds were evaluated. Although further optimizations are needed, our findings lay the groundwork for the future drug development of this class of small molecule agents for the treatment of severe sepsis.

Selection, preparation, and evaluation of small-molecule inhibitors of toll-like receptor 4

Toll-like receptor 4 (TLR4), a membrane-spanning receptor protein that functions in complex with its accessory protein MD-2, is an intriguing target for therapeutic development. Herein, we report the identification of a series of novel TLR4 inhibitors and