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At least 19 recordsLinked to original sources
PubMed2005

Short-term oral toxicity of butyl ether, ethyl hexyl ether, methyl heptyl ether and 1,6-dimethoxyhexane in male rats and the role of 2-methoxyacetic acid.

A 4-week oral study was conducted in male rats to characterize and compare the toxicity of four aliphatic ethers (butyl ether, BE; ethyl hexyl ether, EHxE; methyl heptyl ether, MHpE; and 1,6-dimethoxyhexane, DMH) which have been proposed as high-cetane diesel additives. Male Sprague-Dawley rats (280+/-20 g) were divided into groups of seven animals each and were administered by gavage low (2mg/kg body weight), medium (20mg/kg) or high (200mg/kg) doses of BE, EHxE, or MHpE, 5 days per week for 4 weeks. Another group of animals was administered DMH at 200mg/kg while the control group received the vehicle (corn oil at 1 ml/100g bw) only. At the end of the treatment period, relative testis weights and thymus weights were significantly decreased in the DMH group but not in animals receiving BE, EHxE, or MHpE. Microscopic examination revealed degeneration of the seminiferous tubules and reduction of sperm density in the epididymides in the DMH treatment group. Urinary creatine/creatinine ratio, a sensitive indicator of testicular damage, was markedly elevated in the DMH treated animals but not in those treated with BE, EHxE, or MHpE. In the bone marrow, DMH caused mild dyserythropoiesis and dysthrombopoiesis, while BE, EHxE, and MHpE produced mild increases in granulocytes and myelocyte/erythrocyte ratio. All four ethers at 200mg/kg caused mild histological changes in the thyroid but no significant modulation in the circulating thyroxin (T4) or triiodothyronine (T3) levels. All four ethers produced hepatic effects at 200mg/kg consisting of mild, adaptive histological changes, increased urinary ascorbic acid output, and elevation in the activities of one or more xenobiotic metabolizing enzymes (benzyloxyresorufin-O-dealkylase, UDP-glucuronosyltransferase, glutathione-S-transferases). The level of 2-methoxyacetic acid (MAA), a known testicular and developmental toxin, was significantly increased in the urine and plasma of animals treated with DMH but not in those administered the high dose BE, EHxE, or MHpE. Amomg the individual rats treated with DMH, the MAA level appeared to correlate with the severity of toxicity such as testicular and thymic weights, and urinary creatine/creatinine ratio. It is concluded that BE, EHxE, and MHpE differed from DMH in that they did not produce testicular or thymic toxicity. All four ethers at high dose caused changes to the thyroid, liver and bone marrows that were mild and adaptive in nature. MAA appeared to be the proximal toxicant in DMH treated animals but the route by which DMH is metabolized to MAA remains to be elucidated.

Acetates↗
PubMed1987

Field study of the urinary excretion of ethoxyacetic acid during repeated daily exposure to the ethyl ether of ethylene glycol and the ethyl ether of ethylene glycol acetate.

The urinary excretion of ethoxyacetic acid (EAA) was studied in a group of five women daily exposed to the ethyl ether of ethylene glycol (EGEE) and the ethyl ether of ethylene glycol acetate (EGEE-Ac) during 5 d of normal production and 7 d after a 12-d production stop. The mean combined exposure concentration of EGEE and EGEE-Ac (expressed in equivalent weight of EGEE) was 14.0 mg/m3 with occasional slight excursions above the current Belgian occupational exposure limit. The daily combined exposure profiles for EGEE and EGEE-Ac were rather constant during the first observation period, but they tended to decrease during the last week. The urinary EAA excretion clearly increased during the work week. Over the weekends the elimination was far from complete, and even after a prolonged nonexposure period of 12 d traces of the metabolite were still detectable. Based on the observations from the first period, a good linear correlation (r = 0.92) was found between the average exposure over 5 d (14.4 mg/m3) and the EAA excretion at the end of the week (105.7 mg/g creatinine). An EAA estimate of 150 +/- 35 mg/g was found to correspond with repeated 5-d full-shift exposures to the respective occupational exposure limit of EGEE (19 mg/m3) or EGEE-Ac (27 mg/m3).

Acetates↗
PubMedDate not supplied

Composition and protein efficiency ratio of meat samples partially defatted with petroleum ether, acetone, or ethyl ether.

Freeze-dried beef samples were partially defatted with either petroleum ether, acetone, or ethyl ether before determination of protein efficiency ratio (PER) to study the extraction effects on the composition and protein nutritional quality of the extracted beef. Defatting a protein source, such as meat or a meat product, may often be necessary to produce a test diet that contains 10% protein and 8% fat. Amino acid, carnosine, anserine, creatine, creatinine, inosine, and proximate compositions were determined on the extracted samples. Resulting data were compared to the composition and PER data of the beef that had no solvent treatment. Although the chemical analysis data from the study showed some variation between the proteins and other nitrogenous components of the unextracted and the extracted beef, these variations were too small to affect the protein nutritional quality of the beef as measured by PER.

Acetone↗
PubMed1981

Comparison of formalin-ethyl ether sedimentation, formalin-ethyl acetate sedimentation, and zinc sulfate flotation techniques for detection of intestinal parasites.

Formalin-ethyl ether sedimentation, Formalin-ethyl acetate sedimentation, and zinc sulfate flotation techniques were compared using over 250 clinical parasitology specimens. Fifty positive specimens were identified, and a variety of parasites, including amoebae, flagellates, cestodes, nematodes, and trematodes, were encountered. The Formalin-ether and Formalin-ethyl acetate sedimentation procedures gave identical results for the detection of cysts, ova, and larvae, and these methods offered an advantage over the flotation procedure for the detection of selected ova. However, the zinc sulfate procedure was more effective for the detection of protozoan cysts, Hymenolepis nana, and hookworm eggs. The results indicate that the Formalin-ethyl acetate procedure provides a suitable alternative to the Formalin-ether method, and they demonstrate the value of using both flotation and sedimentation procedures in the analysis of fecal specimens for parasites.

Acetates↗
PubMed1997

Biodegradation of the gasoline oxygenates methyl tert-butyl ether, ethyl tert-butyl ether, and tert-amyl methyl ether by propane-oxidizing bacteria.

Several propane-oxidizing bacteria were tested for their ability to degrade gasoline oxygenates, including methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE), and tert-amyl methyl ether (TAME). Both a laboratory strain and natural isolates were able to degrade each compound after growth on propane. When propane-grown strain ENV425 was incubated with 20 mg of uniformly labeled [14C]MTBE per liter, the strain converted > 60% of the added MTBE to 14CO2 in < 30 h. The initial oxidation of MTBE and ETBE resulted in the production of nearly stoichiometric amounts of tert-butyl alcohol (TBA), while the initial oxidation of TAME resulted in the production of tert-amyl alcohol. The methoxy methyl group of MTBE was oxidized to formaldehyde and ultimately to CO2. TBA was further oxidized to 2-methyl-2-hydroxy-1-propanol and then 2-hydroxy isobutyric acid; however, neither of these degradation products was an effective growth substrate for the propane oxidizers. Analysis of cell extracts of ENV425 and experiments with enzyme inhibitors implicated a soluble P-450 enzyme in the oxidation of both MTBE and TBA. MTBE was oxidized to TBA by camphor-grown Pseudomonas putida CAM, which produces the well-characterized P-450cam, but not by Rhodococcus rhodochrous 116, which produces two P-450 enzymes. Rates of MTBE degradation by propane-oxidizing strains ranged from 3.9 to 9.2 nmol/min/mg of cell protein at 28 degrees C, whereas TBA was oxidized at a rate of only 1.8 to 2.4 nmol/min/mg of cell protein at the same temperature.

Bacteria↗
PubMed1998

Biotransformation of 12C- and 2-13C-labeled methyl tert-butyl ether, ethyl tert-butyl ether, and tert-butyl alcohol in rats: identification of metabolites in urine by 13C nuclear magnetic resonance and gas chromatography/mass spectrometry.

The biotransformation of the fuel oxygenates methyl tert-butyl ether (MTBE) and ethyl tert-butyl ether (ETBE) was studied in rats after inhalation exposure; the biotransformation of the initial metabolite of these ethers, tert-butyl alcohol, was studied after oral gavage. To study ether metabolism, rats were exposed for 6 h to initial concentrations of 2000 ppm of MTBE or ETBE, respectively [2-13C]MTBE and [2-13C]ETBE. Urine was collected for 48 h after the end of the exposure, and urinary metabolites were identified by 13C NMR (13C-labeled ethers) and gas chromatography/mass spectrometry (GC/MS) (12C- and 13C-labeled ethers). To study tert-butyl alcohol metabolism, rats were dosed either with tert-butyl alcohol at natural carbon isotope ratio or with 13C-enriched tert-butyl alcohol (250 mg/kg of body weight), urine was collected, and metabolites were identified by NMR and GC/MS. tert-Butyl alcohol was identified as a minor product of the biotransformation of MTBE and ETBE. In addition, small amounts of a tert-butyl alcohol conjugate, likely a glucuronide, were present in the urine of the treated animals. Moreover, the mass spectra obtained indicate the presence of small amounts of [13C]acetone in the urine of [13C]MTBE and [13C]ETBE-treated rats. 2-Methyl-1,2-propanediol, 2-hydroxyisobutyrate, and another unidentified conjugate of tert-butyl alcohol, most probably a sulfate, were major urinary metabolites of MTBE and ETBE as judged by the intensities of the NMR signals. In [13C]-tert-butyl alcohol-dosed rats, [13C]acetone, tert-butyl alcohol, and its glucuronide represented minor metabolites; as with the ethers, 2-methyl-1,2-propanediol, 2-hydroxyisobutyrate, and the presumed tert-butyl alcohol sulfate were the major metabolites present. In one human individual given 5 mg/kg [13C]-tert-butyl alcohol orally, 2-methyl-1,2-propanediol and 2-hydroxyisobutyrate were major metabolites in urine detected by 13C NMR analysis. Unconjugated tert-butyl alcohol and tert-butyl alcohol glucuronide were present as minor metabolites, and traces of the presumed tert-butyl alcohol sulfate were also present. Our results suggest that tert-butyl alcohol formed from MTBE and ETBE is intensively metabolized by further oxidation reactions. Studies to elucidate mechanisms of toxicity for these ethers to the kidney need to consider potential toxicities induced by these metabolites.

Animals↗
PubMed1997

The acute toxicity and irritancy of bis[2-(dimethylamino)ethyl]ether.

Bis[2-(dimethylamino)ethyl]ether (DMAEE; CAS No 3033-62-3) is an industrial liquid chemical used principally as an amine catalyst. It was investigated for potential acute hazards. DMAEE is of moderate acute peroral toxicity with LD50 values in the rat of 1045 ml/kg and 1198 mg/kg in 2 separate tests and producing gastric injury. Dilution (25% in corn oil) had no significant influence; LD50 909 mg/kg. It is of moderately high acute percutaneous toxicity in the rabbit; LD50 values by 4 h occlusive contact are 348 mg/kg (male) and 535 mg/kg (female), and for 24 h 314 mg/kg (male and female). Dilution (20% DMAEE in water) did not influence lethal toxicity; LD50 363 mg/kg (male) and 481 mg/kg (female). Skin contact produced severe irritation and injury, notably erythema, edema, ulceration, desquamation and scab formation. Necrosis was produced in 5/6 rabbits with a 3-min occluded contact. DMAEE produced severe eye injury, with blepharo-conjunctivitis and corneal injury from undiluted and 10% aqueous DMAEE; threshold conjunctival effect occurred at 1% aqueous DMAEE. Vapor concentration was dependent on relative humidity, concentration increasing with decreasing humidity. A statically generated vapor atmosphere was not lethal to rats due to the accumulation of water vapor from expired air (mean DMAEE = 24 ppm; 6 h exposure). With a dynamically generated atmosphere, where relative humidity could be controlled, the 6 h LC50 to rats was 166 ppm (males and females). Signs included those of ocular and respiratory irritation. DMAEE is acutely hazardous by swallowing, skin and eye contact, and exposure to moderately high vapor concentrations. Appropriate protective and precautionary measures are reviewed.

Animals↗
PubMed1999

Polyhalogenated methyl ethyl ethers: solubilities and anesthetic properties.

UNLABELLED: The several potent inhaled anesthetics released for clinical use in the past four decades have been halogenated ethers, and, with one exception, methyl ethyl ethers. In the present report, we detail some structural and physical properties associated with anesthetic potency in 27 polyhalogenated methyl ethyl ethers. We obtained new data for 22 compounds. We used response/nonresponse of rats to electrical stimulation of the tail as the anesthetic end point (i.e., we measured the minimum alveolar anesthetic concentration [MAC]). For compounds that did not produce anesthesia when given alone (they only produced excitation/convulsions), we studied MAC by additivity studies with desflurane. We obtained MAC values for 20 of 22 of the studied ethers, which gave products of MAC x oil/gas partition coefficient ranging from 1.27 to 18.8 atm, compared with a product of 1.82+/-0.56 atm for conventional inhaled anesthetics. Despite solubilities in olive oil and application of partial pressures predicted by the Meyer-Overton hypothesis to provide anesthesia, 2 of 22 ethers (CCIF2OCCIFCF3 and CCIF2OCF2CClF2) had no anesthetic (immobilizing) effect when given alone, did not decrease the anesthetic requirement for desflurane, and had excitatory properties when administered alone. As with other inhaled anesthetics, anesthetic potency seemed to correlate with both polar and nonpolar properties. These ethers, representing structural analogs of currently used clinical volatile anesthetics, may be useful in identifying and understanding the mechanisms by which inhaled anesthetics act. IMPLICATIONS: The several potent, inhaled, polyhalogenated methyl ethyl ether anesthetics released for clinical use in the past four decades seem to have specific useful characteristics that set them apart from other methyl ethyl ethers. Properties of this class of compounds have implications for the future development of anesthetics and the mechanisms by which they act.

Anesthetics, Inhalation↗