6274-74-4

Basic information

• Product Name: 1,3-bis(benzyloxy)-2,5-dimethoxybenzene
• CAS NO: 6274-74-4
• Molecular Formula: C₂₂H₂₂O₄
• Molecular Weight: 350.4077
• Mol File: 6274-74-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 492.3°C at 760 mmHg
• Flash Point: 142.7°C
• Density: 1.141g/cm³
• Vapor Pressure: 2.36E-09mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 1,3-bis(benzyloxy)-2,5-dimethoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-bis(benzyloxy)-2,5-dimethoxybenzene(6274-74-4)
• EPA Substance Registry System: 1,3-bis(benzyloxy)-2,5-dimethoxybenzene(6274-74-4)

Safety Data

• Hazardous Substances Data: 6274-74-4(Hazardous Substances Data)

Usage

Chemical class

Benzene derivatives

Structure

Two benzyloxy groups at the 1 and 3 positions, and two methoxy groups at the 2 and 5 positions of the benzene ring

Common use

Building block in organic synthesis, particularly for pharmaceuticals and agrochemicals

Potential biological activities

Anti-inflammatory and anti-cancer properties

Upstream product

• 42528-81-4 2,6-bis-benzyloxy-benzene-1,4-diol 
• 77-78-1 dimethyl sulfate 
• 42528-82-5 1,2-dibenzyloxy-1,4-hydroquinone-diacetate 
• 13326-72-2 3,5-bis(benzyloxy)-4-methoxybenzaldehyde 
• 27229-56-7 [3,5-bis(benzyloxy)-4-methoxyphenyl]methanol 
• 13326-69-7 methyl 3,5-bis(benzyloxy)-4-methoxybenzoate 
• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 74-88-4 methyl iodide 
• 99-24-1 methyl galloate 
• 6625-45-2 2,6-bis-benzyloxy-[1,4]benzoquinone 
• 87-66-1 2-hydroxyresorcinol 
• 100-39-0 benzyl bromide 
• 55020-64-9 1,2,3-tris-benzyloxybenzene 

Downstream Products

• 129724-43-2 (E)-1-(2,4-dihydroxy-3,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one 
• 1969289-10-8 (+)-celosine 
• 884867-44-1 5,7-dihydroxy-8-methoxy-2-(4-chlorophenyl)-4H-chromen-4-one 
• 884867-40-7 5,7-dihydroxy-8-methoxy-2-(p-tolyl)-4H-chromen-4-one 
• 65501-87-3 5,7-dihydroxy-8-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 1175077-25-4 5-hydroxy-8-methoxy-7-(4-(4-methylpiperazin-1-yl)butoxy)-2-phenyl-4H-chromen-4-one 
• 3316-54-9 7-hydroxy-5,8-dimethoxyflavone 

Relevant articles and documents

Design of wogonin-inspired selective cyclin-dependent kinase 9 (CDK9) inhibitors with potent in vitro and in vivo antitumor activity

Wogonin, a natural product isolated from the plant Scutellaria baicalensis, has been shown to be a potent and selective inhibitor of CDK9. With the purpose of investigating the activity and selectivity of this chemical scaffold, several series of wogonin derivatives were prepared and screened for CDK9 inhibition and cellular antiproliferative activity. Among these compounds, the drug-like compound 51 showed potent activity against CDK9 (IC50 = 19.9 nM) and MV4-11 cell growth (IC50 = 20 nM). In addition, compound 51 showed much improved physicochemical properties, such as water solubility, compared with the parent compound wogonin. The follow-up studies showed that the compound 51 is selective toward CDK9-overexpressing cancer cells over normal cells. Preliminary mechanism studies on the anticancer effect indicated that 51 inhibited the proliferation of MV4-11 cells via caspase-dependent apoptosis. In addition, highlighted compound 51 showed significant antitumor activity in mouse acute myeloid leukemia (AML) models without producing apparent toxic effects in vivo, which gave us a new tool for further investigation of CDK9-targeted inhibitor as a potential antitumor drug especially for AML.

Synthesis, evaluation and quantitative structure–activity relationship (QSAR) analysis of Wogonin derivatives as cytotoxic agents

A novel series of 49 wogonin derivatives were synthesized by introducing group at 7-, 8- or B ring of wogonin. The cytotoxic activities against HepG2, A549 and BCG-823 cancer cell lines were also investigated in vitro. Several of them showed obvious cytotoxic activities and compound 3h possessed the highest potency against HepG2, A549, and BCG-823 with IC50 values of 1.07 μM, 1.74 μM and 0.98 μM, respectively. A quantitative structure-activity relationship (QSAR) study of these synthetic derivatives as well as wogonin indicated that high solubility and low octanol/water partition coefficient are favorable, and excessive electrostatic properties and refractivity are unfavorable for the cytotoxic activities of these wogonin derivatives. These findings and results provide a base for further investigations.

ENHANCING AUTOPHAGY OR INCREASING LONGEVITY BY ADMINISTRATION OF UROLITHINS OR PRECURSORS THEREOF

Disclosed are methods, compounds, and compositions useful for increasing autophagy and promoting longevity. The methods, compounds, and compositions relate to urolithins and urolithin precursors and use thereof. Certain urolithins are represented by Formula I, while certain urolithin precursors are represented by Formula IV. The urolithin may be urolithin A, urolithin B, urolithin C, or urolithin D. The urolithin precursor may be ellagic acid or an ellagitannin. The methods include in vivo, ex vivo, and in vitro uses of the compounds and compositions.