75427-76-8

Basic information

• Product Name: BUTETH-3 CARBOXYLIC ACID
• Synonyms: Aceticacid, [2-(2-butoxyethoxy)ethoxy]- (9CI)
• CAS NO: 75427-76-8
• Molecular Formula: C₁₀H₂₀O₅
• Molecular Weight: 220.26
• Mol File: 75427-76-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BUTETH-3 CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BUTETH-3 CARBOXYLIC ACID(75427-76-8)
• EPA Substance Registry System: BUTETH-3 CARBOXYLIC ACID(75427-76-8)

Safety Data

• Hazardous Substances Data: 75427-76-8(Hazardous Substances Data)

Upstream product

• 112-34-5 Diethylene glycol monobutyl ether 
• 79-11-8 chloroacetic acid 
• 143-22-6 triethyleneglycol monobutyl ether 

Downstream Products

• 75427-83-7 3-Benzyloxypropylenbis(3,6,9-trioxatridecanoat) 

Relevant articles and documents

Development of small-molecule inhibitors of fatty acyl-AMP and fatty acyl-CoA ligases in Mycobacterium tuberculosis

Lipid metabolism in Mycobacterium tuberculosis (Mtb) relies on 34 fatty acid adenylating enzymes (FadDs) that can be grouped into two classes: fatty acyl-CoA ligases (FACLs) involved in lipid and cholesterol catabolism and long chain fatty acyl-AMP ligases (FAALs) involved in biosynthesis of the numerous essential and virulence-conferring lipids found in Mtb. The precise biochemical roles of many FACLs remain poorly characterized while the functionally non-redundant FAALs are much better understood. Here we describe the systematic investigation of 5′-O-[N-(alkanoyl)sulfamoyl]adenosine (alkanoyl adenosine monosulfamate, alkanoyl-AMS) analogs as potential multitarget FadD inhibitors for their antitubercular activity and biochemical selectivity towards representative FAAL and FACL enzymes. We identified several potent compounds including 12-azidododecanoyl-AMS 28, 11-phenoxyundecanoyl-AMS 32, and nonyloxyacetyl-AMS 36 with minimum inhibitory concentrations (MICs) against M. tuberculosis ranging from 0.098 to 3.13 μM. Compound 32 was notable for its impressive biochemical selectivity against FAAL28 (apparent Ki = 0.7 μM) versus FACL19 (Ki > 100 μM), and uniform activity against a panel of multidrug and extensively drug-resistant TB strains with MICs ranging from 3.13 to 12.5 μM in minimal (GAST) and rich (7H9) media. The SAR analysis provided valuable insights for further optimization of 32 and also identified limitations to overcome.

CONFIGURATIONAL BIASING OF TERTIARY AMIDE IONOPHORES BY ALKALI METAL CHELATION1,2.

Configurational analysis can be used as a probe for association constants for chelation of amides with alkali metals. Carbon-13 NMR spectroscopy indicates that tertiary amides, each bearing a triethylene oxide substituent at nitrogen, exist as a mixture of E and Z isomers. Addition of alkali metal cation (KSCN) increases the concentration of species with the Z configuration since this configuration can chelate potassium ion. High-field **1H NMR spectra have been used to determine the chelation constants for amides in the presence of KSCN. It has been determined that (a) the carbonyl oxygen is involved in chelation and (b) the number of ether oxygens on the substituent at nitrogen is the significant factor in the chelating ability of these ionophores.

Hydrophilic Lipids

The new triesters of glycerol 1-8 with different oligoethylene glycol carboxylic acids ("hydrophilic lipids") have been synthesized and their complexation with alkali and alkaline earth metal cations has been investigated.