Cyclopentyl methyl ether (CPME) has become available in commercial quantities since November 2005 from Zeon Corporation with approval by the Toxic Substances Control Act (TSCA) and the European List of Notified Chemical Substances (ELINCS). A high boiling point (106°C) and preferable characteristics such as low formation of peroxides, relative stability under acidic and basic conditions, formation of azeotropes with water coupled with a narrow explosion range render CPME an alternative to other ethereal solvents such as tetrahydrofuran (THF), 2-methyl tetrahydrofuran (2-MeTHF), dioxane (carcinogenic), and 1,2-dimethoxyethane (DME). Conventional drying is unnecessary for general organometallic reactions including Grignard reactions, enolate formation, Claisen condensation, general reductions, and Pd-based transformations.
SUMMARYIL-8 is generating increasing interest as a powerful neutrophil chemoattractant and activator. To elucidate the mechanisms of neutrophil infiltration in inflammatory bowel disease, we examined 33 patients with ulcerative colitis (UC), 18 with Crohn's disease (CD), eight with some other type of colitis, and 18 normal control subjects for measurement of IL-8 in homogenates of colonic biopsy specimens. The affected colonic mucosa was found to contain significantly more IL-8 in patients with active inflammatory bowel disease than in patients with inactive disease (UC, P<0-001; CD, P < 0-001), in patients with other types of colitis (UC, P < 0 05; CD, P < 0-0 1), or in normal control subjects (UC, P<0-001; CD, P<0-001). Colonic IL-8 levels correlated significantly with the macroscopic grade of local inflammation, especially in patients with UC (P< 0-001). Colonic IL-8 levels also correlated well with the neutrophil numbers in mucosal tissue (UC, r = 0-950, P <0-001; CD, r = 0 940, P < 0-001), and with colonic IL-1I (r = 0-91 1, P < 0-001) and tumour necrosis factoralpha (TNF-a) levels (r = 0-604, P < 0-001 ) in patients with these two conditions. These data suggest a potential role for IL-8 and its regulatory cytokines IL-1 and TNF-a in mediating neutrophil infiltration of the gut wall in inflammatory bowel disease.
Cyclopentyl methyl ether (CPME) has been used in chemical synthesis as an alternative to hazardous solvents. According to some earlier investigation by others, CPME has low acute or subchronic toxicity with moderate irritation and negative mutagenicity and negative skin sensitization (Local Lymph Node Assay). Calculated Permitted Daily Exposure (PDE) value of CPME obtained by our 28-day oral toxicity test is 1.5 mg/day, and CPME is thus assumed to be a class 2 equivalent solvent in the ICH (International Conference on Harmonization) Harmonized Tripartite Guideline Q3C (R5). Wide synthetic utility and a detailed toxicity study suggest CPME as a green and sustainable solvent of choice for modern chemical transformations.
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