10438-94-5

Usage

InChI:InChI=1/C22H42O7/c1-3-5-7-9-11-13-19(21(27)17(25)15-23)29-20(22(28)18(26)16-24)14-12-10-8-6-4-2/h17-20,23-26H,3-16H2,1-2H3

Upstream product

• 17158-60-0 sodium octanolate 
• 96-24-2 3-monochloro-1,2-propanediol 
• 1191-44-2 3-oct-1-en-t-yloxy-propane-1,2-diol 
• 111-87-5 octanol 
• 111-83-1 1-bromo-octane 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 3385-66-8 octyl glycidyl ether 
• 56-81-5 glycerol 
• 126911-83-9 1-chloro-3-octyloxy-propan-2-ol 
• 91369-08-3 [2-(1-bromo-heptyl)-[1,3]dioxolan-4-yl]-methanol 
• 556-52-5 oxiranyl-methanol 
• 124-13-0 Octanal 
• 124-07-2 Octanoic acid 
• 19670-49-6 monocaprylin 

Relevant academic research and scientific papers

Straightforward selective synthesis of linear 1-O-alkyl glycerol and di-glycerol monoethers

1-O-Alkyl glycerol and di-glycerol monoethers are, respectively, obtained in high yields and selectivity by catalytic reductive etherification of mono- and di-glycerol with linear aldehydes in the presence of 0.5 mol % of Pd/C under 10 bars of hydrogen us

Detergent-Like Polymerizable Monomers: Synthesis, Physicochemical, and Biochemical Characterization

Three monomers with a maltose polar head, an alkyl hydrogenated chain, and an acrylamide-based polymerizable moiety were synthesized. The self-assembly properties in aqueous solutions of these monomers were studied by means of isothermal titration calorimetry (ITC), surface tension (SFT) measurements, and dynamic light scattering (DLS), which indicated the formation of small micellar aggregates of about 6 nm diameter. The critical micellar concentration (CMC) was found to depend on the length of the alkyl chain and on the nature of the polymerizable moiety, ranging from 0.35 mm to ca. 10 mm. The monomers were found to solubilize phospholipid vesicles and to extract a broad range of proteins from Escherichia coli membranes. Finally, the extraction of two membrane proteins, namely, the full-length, wild-type human G-protein-coupled receptor (GPCR) adenosine A2A receptor (A2AR) and the bacterial transporter AcrB was demonstrated.

Design, synthesis and cytotoxicity of chimeric erlotinib-alkylphospholipid hybrids

Two series of erlotinib-alkylphospholipid hybrids were prepared and evaluated for their antiproliferative activities against a panel of four cell lines representing lung, breast, liver and skin cancers using erlotinib and miltefosine as reference standards. Amide analogs elicited more enhanced cytotoxic activity than analogous esters. Amide derivatives 8d and 8e exhibited promising broad-spectrum antiproliferative activity and higher efficacy than reference erlotinib and miltefosine. Their cellular GI50 values was in the ranges of 24.7–46.9 μM and 26.8–43.1 μM for 8e and 8d respectively. Assay results of the inhibitory activity of the prepared compounds on EGFR kinase reaction and Akt phosphorylation in conjugation with statistical correlation analysis indicated that other mechanisms might contribute to their elicited cytotoxicities. In addition, statistical correlation analysis revealed that mechanisms of elicited cytotoxicities for amide series might be different from ester series. In addition, correlation analysis indicated variations in the mechanisms according to the types of cell line.

Regioselective Ring-Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]-FeIII Triflate Complex

A FeIII-triflate complex, bearing a bis-thioether-di-phenolate [OSSO]-type ligand, was discovered to promote the ring-opening of glycidol with alcohols under mild reaction conditions (0.05 mol % catalyst and 80 °C). The reaction proceeded with high activity (initial turnover frequency of 1680 h?1 for EtOH) and selectivity (>95 %) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in a regioselective fashion (84–96 % yield of the non-symmetric regioisomer). This synthetic approach allows the conversion of a glycerol-derived platform molecule (i.e., glycidol) to high-value-added products by using an Earth-crust abundant metal-based catalyst.

SOOTHING PRO-PHEROMONAL COMPOSITION FOR MAMMALS

The invention relates to a compound of general formula (I) (in configuration Z or E) and to pro-pheromonal compositions and formulations comprising said compound, in addition to the uses thereof for soothing purposes for non-human mammals such as sheep, pigs, sheep, cattle, felines, equines and canines.

Synthesis of Monoalkyl Glyceryl Ethers by Ring Opening of Glycidol with Alcohols in the Presence of Lewis Acids

The present work deals with the production of monoalkyl glyceryl ethers (MAGEs) through a new reaction pathway based on the reaction of glycidol and alcohols catalyzed by Lewis acid-based catalysts. Glycidol is quantitatively converted with high selectivity (99 %) into MAGEs under very mild reaction conditions (80 °C and 0.01 mol % catalyst loading) in only 1 h using Al(OTf)3 or Bi(OTf)3 as catalyst. The proposed method enhances the choice of possible green synthetic approaches for the production of value-added products such as MAGEs.

METHOD FOR PREPARING GLYCEROL ETHER AND GLYCOL ETHER

The present invention concerns a method for preparing glycerol ether or glycol ether comprising the reaction of a compound of formula (II) with a compound of formula (III) in the presence of a heterogeneous acid catalyst of formulas (II) and (III).

PROCESS FOR PREPARING A POLYOL ETHER

The present invention relates to a process for preparing a polyol ether of formula (I), comprising a step of reductive alkylation involving a compound of general formula (II) and a compound of general formula (III): in which R1, R2, R3 and R4 are as defined in claim 1.

1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: Catalytic reductive alkylation and transesterification/reduction

From available and bio-sourced methyl esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters or triolein and consisted of a first transesterification to the corresponding monoglyceride with a BaO/Al2O3 catalyst, then its reduction to the desired glycerol monoether with a recyclable heterogeneous catalytic system Pd/C and Amberlyst 35 under H2 pressure. In addition, a mechanism for the reaction was also proposed.

1,2,3-Trimethoxypropane and glycerol ethers as bio-sourced solvents from glycerol: Synthesis by solvent-free phase-transfer catalysis and utilization as an alternative solvent in chemical transformations

1,2,3-Trimethoxypropane (2), 1-alkoxy-2,3-dimethoxy-propanes, and 1-aryloxy-2,3-dimethoxypropanes were prepared in good yields and selectivity by solid-liquid phase-transfer catalysis in the presence of an inorganic base and an ammonium salt as the phase-transfer catalyst with no additional solvent. No heating was required, and the synthesis was easily performed under atmospheric pressure on a 150g scale. For the preparation of 2, the conversion of glycerol was complete and the selectivity for the expected glycerol trimethylether was above 95%. This product was utilized as a solvent in organic reactions such as transesterifications between glycerol and vegetable oil, organometallic reactions (Grignard- and Barbier-type reactions), carbon-carbon coupling reactions (Suzuki, Sonogashira, Heck), and in etherification reactions by dehydrogenative alkylation. The solvent showed interesting properties for the solubilization of polymers.