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Concept: Glycol ethers

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The main objective of the following study was to determine the efficiency of a method that uses coconut charcoal as a solid-phase extraction (SPE) adsorbent in order to simultaneously detect six hydrophilic ether species in water in the low microgram-per-liter range. The applied method was validated for quantification of ethyl tert-butyl ether, 1,4-dioxane, ethylene glycol dimethyl ether (monoglyme), diethylene glycol dimethyl ether (diglyme), triethylene glycol dimethyl ether (triglyme) and tetraethylene glycol dimethyl ether (tetraglyme). SPE followed by gas chromatography/mass spectrometry of the extracts using the selected ion monitoring mode allowed for establishing low detection limits in the range of 0.007-0.018 μg/L in ultrapure water and 0.004-0.020 μg/L in environmental samples. Examination of the method accuracy and precision resulted in a recovery greater than 86.8 % for each compound with a relative standard deviation of less than 6.6 %. A stability study established a 5-day holding time for the unpreserved water samples and extracts. Finally, 27 samples obtained from surface water bodies in Germany were analyzed for the six hydrophilic ethers. Each analyte was detected in at least eight samples at concentrations reaching 2.0 μg/L. The results of this study emphasize the advantage of the method to simultaneously determine six hydrophilic ether compounds. The outcome of the surface water analyses augments a concern about their frequent and significant presence in surface water bodies in Germany.

Concepts: Ether, Ethylene glycol, Ethylene oxide, Diethylene glycol, Triethylene glycol, Ethers, Glycol ethers, Dimethoxyethane

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Glycol ethers are a class of semi-volatile substances used as solvents in a variety of consumer products like cleaning agents, paints, cosmetics as well as chemical intermediates. We determined 11 metabolites of ethylene and propylene glycol ethers in 44 urine samples of German residents (background level study) and in urine samples of individuals after exposure to glycol ethers during cleaning activities (exposure study). In the study on the background exposure, methoxyacetic acid and phenoxyacetic acid (PhAA) could be detected in each urine sample with median (95th percentile) values of 0.11mgL(-1) (0.30mgL(-1)) and 0.80mgL(-1) (23.6mgL(-1)), respectively. The other metabolites were found in a limited number of samples or in none. In the exposure study, 5-8 rooms were cleaned with a cleaner containing ethylene glycol monobutyl ether (EGBE), propylene glycol monobutyl ether (PGBE), or ethylene glycol monopropyl ether (EGPE). During cleaning the mean levels in the indoor air were 7.5mgm(-3) (EGBE), 3.0mgm(-3) (PGBE), and 3.3mgm(-3) (EGPE), respectively. The related metabolite levels analysed in the urine of the residents of the rooms at the day of cleaning were 2.4mgL(-1) for butoxyacetic acid, 0.06mgL(-1) for 2-butoxypropionic acid, and 2.3mgL(-1) for n-propoxyacetic acid. Overall, our study indicates that the exposure of the population to glycol ethers is generally low, with the exception of PhAA. Moreover, the results of the cleaning scenarios demonstrate that the use of indoor cleaning agents containing glycol ethers can lead to a detectable internal exposure of residents.

Concepts: Median, Arithmetic mean, Ethylene glycol, Diol, Propylene glycol, Background radiation, Urinalysis, Glycol ethers

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A 24 hour in vitro Xenopus oocyte maturation (germinal vesicle breakdown [GVBD]) assay developed by Pickford and Morris (Environmental Health Perspectives, 1999, 107, 285-292) was used to screen a series of substituted glycol ethers (GEs). Substituted GEs included: ethylene glycol monomethyl ether (EGME); EG monoethyl ether (EGEE); EG monopropyl ether (EGPE); EG monobutyl ether (EGBE); EG monohexyl ether (EGHE); diethylene glycol monomethyl ether (DGME); triethylene glycol monomethyl ether (TGME); ethylene glycol monophenyl ether (EGPhE); EG monobenzyl ether (EGBeE); EG diphenyl ether (EGDPhE); and propylene glycol monophenyl ether (PGPhE). The GEs inhibited progesterone- or androstenedione-induced GVBD with the following relative potency: EGPhE > PGPhE > EGME > EGEE ≥ EGBeE > EGPE > EGBE >EGHE > EGDPhE > DGME ≥ TGME, or EGPhE > PGPhE > EGBeE > EGDPhE > EGEE > EGME > EGPE > EGBE, EGHE, DGME and TGME, respectively. Further, [3 H]progesterone or [3 H]androstenedione binding affinities to the oocyte plasma membrane progesterone receptor (OMPR) or classical androgen receptor (AR) were: EGME > EGPhE ≥ PGPhE ≥ EGEE > EGBeE > EGPE > EGBE ≥ EGHE > EGDPhE, TGME, and DGME, or EGPhE > PGPhE > EGBeE > EGDPhE > EGEE ≥ EGME > EGPE, EGBE, and EGHE > DGME and TGME, respectively. Binary joint mixture studies with the GVBD model using flutamide (AR antagonist) and EGPhE indicated that flutamide/EGPhE mixture acted in a concentration additive manner. The effects of substituted GE series, however, may be mediated through the OMPR; the potency of EGPhE may be the result of bimodal inhibition of both the OMPR and AR pathways.

Concepts: Ethylene glycol, Ethylene oxide, Propylene glycol, Diethylene glycol, Glycol ethers

0

Studies on the hematologic toxicity of ethylene glycol ethers in humans are limited. Therefore, the aim of this study was to examine the association between exposure to solvents (containing 2-butoxyethanol and 2-ethoxyethanol) and hematological effects.

Concepts: Blood, Hematology, The Association, Ethylene glycol, Alcohols, Glycol ethers, 2-Ethoxyethanol, 2-Butoxyethanol

0

The aim of this investigation is to clarify the types and concentrations of VOCs present in various commercial household water-based hand pump spray products used in Japan, and to estimate their average concentrations in indoor air when the spray product is used. We selected glycol and glycol ethers as the main target compounds, as these chemicals were detected at high frequencies and concentrations in a national survey of Japanese indoor air pollution. The extraction of these chemicals using graphite carbon cartridges was examined, with good recoveries and reproducibilities being obtained. Eighteen chemicals were analyzed in 54 commercial products and 8 chemicals were detected. More specifically, dipropylene glycol (DPG) was present in 44 samples (1.1 × 10(1)-1.8 × 10(4) μg/mL); propylene glycol (PG) was present in 22 samples (1.5 × 10(1)-2.9 × 10(4) μg/mL); diethylene glycol monoethyl ether (DGMEE) was found in 15 samples (trace amount-1.9 × 10(3) μg/mL); diethylene glycol (DEG) was present in 9 samples (1.0 × 10(1)-2.4 × 10(3) μg/mL); 1,3-butandiol (13BG) was found in 5 samples (trace amount-7.4 × 10(3) μg/mL); 2-ethyl-1-hexanol (2E1H) was detected in 5 samples (3.2 × 10(-1)-4.4 × 10(1) μg/mL); diethylene glycol monobutyl ether (DGMBE) was present in 4 samples (2.1 × 10(1)-7.1 × 10(1) μg/mL); and 3-methoxy-3-methylbutanol (MMB) was found in 2 samples (2.4 × 10(1)-4.7 × 10(2) μg/mL). In addition, the average concentrations of these chemicals in indoor air were estimated using their maximum concentrations observed in the spray product. The estimated average concentrations of the chemicals in indoor air were determined to range between 1.0 × 10(-2) and 1.0 mg/m(3), with the exception of 2E1H and DGMBE. Furthermore, the estimated average concentrations of PG, 13BG, and DGMEE in indoor air were comparable to or higher than those reported in a national survey of Japanese indoor air pollution. It therefore appeared that household water-based hand pump sprays may contribute to the presence of these chemicals in indoor air. In contrast, estimated average concentrations of 2E1H in indoor air were low, its concentrations observed in a national survey of Japanese indoor air pollution are likely due to the use of plasticizers and paints.

Concepts: Ethylene glycol, Diol, Volatile organic compound, Propylene glycol, Air pollution, Diethylene glycol, Glycol ethers, Diols

0

Development of self-nanoemulsifying drug delivery systems (SNEDDS) of polypeptide-k (PPK) is reported with the aim to achieve its oral delivery. Box-Behnken design (BBD) was adopted to develop and optimize the composition of SNEDDS. Oleoyl polyoxyl-6 glycerides (A), Tween 80 (B), and diethylene glycol monoethyl ether © were used as oil, surfactant and co-surfactant, respectively as independent variables. The effect of variation in their composition was observed on the mean droplet size (y1), polydispersity index (PDI) (y2), % drug loading (y3) and zeta potential (y4). As per the optimal design, seventeen SNEDDS prototypes were prepared. The optimized composition of SNEDDS formulation was 25% v/v Oleoyl polyoxyl-6 glycerides, 37% v/v Tween 80, 38% v/v diethylene glycol monoethyl ether, and 3% w/v PPK. The optimized formulation revealed values of y1, y2, y3, and y4 as 31.89nm, 0.16, 73.15%, and -15.65mV, respectively. Further the optimized liquid SNEDDS were solidified through spray drying using various hydrophilic and hydrophobic carriers. Among the various carriers, Aerosil 200 was found to provide desirable flow, compression, disintegration and dissolution properties. Both, liquid and solid-SNEDDS have shown release of >90% within 10min. The formulation was found stable with change in pH, dilution, temperature variation and freeze thaw cycles in terms of droplet size, zeta potential, drug precipitation and phase separation. Crystalline PPK was observed in amorphous state in solid SNEDDS when characterized through DSC and PXRD studies. The biochemical, hematological and histopathological results of streptozotocin induced diabetic rats shown promising antidiabetic potential of PPK loaded in SNEDDS at its both the doses (i.e. 400mg/kg and 800mg/kg) as compared to its naïve form at both the doses. The study revealed successful formulation of SNEDDS for oral delivery of PPK.

Concepts: Temperature, Solid, Viscosity, Liquid, Glass, Optimization, Amorphous solid, Glycol ethers

0

Tacrolimus (TAC), a non-steroidal anti-inflammatory and immunosuppressive agent, is used for the treatment of atopic dermatitis (AD) and skin immune diseases. TAC-loaded topical hydrogel formulations composed of carbomer, carnosine, transcutol P (diethylene glycol monoethyl ether), and humectant were prepared. For comparison, TAC-loaded topical cream-type formulations were also prepared and commercially available TAC ointment was used as a reference. A drug release study in vitro revealed that the total amount of TAC released from hydrogels over 24 h was approximately 30 times greater than that for the reference formulation. Compared to the reference ointment and creams, carbomer gel formulations showed higher skin permeation and retention of TAC (significantly different at P < 0.05), especially those with more than 10% of transcutol P. Therefore, carbomer gel formulations with sufficient levels of transcutol P are good candidates for skin delivery of TAC and have potential as therapeutic agents for the treatment of AD or immune skin disorders.

Concepts: Immune system, Immunology, Gel, Agent, Release, Atopic dermatitis, Formulation, Glycol ethers

0

This study investigated the transdermal permeability of baicalin, a hydrophobic and readily hydrolyzed drug, delivered by glyceryl monooleate (GMO)-based cubic phase gel (CPG) mediated with Transcotol(®) P (TP, diethylene glycol monoethyl ether). A range of CPGs was produced by varying GMO, water, and TP levels. Examination of their physicochemical properties revealed that the optically isotropic CPG showed higher viscosity than lamellar phase gels (LPG), and the baicalin cargo increased CPG viscosity. The GMO:TP ratio and water content also altered viscosity. CPG-mediated delivery increased baicalin’s skin permeation, with 76.65- to 200.24-fold higher (p<0.05) transdermal flux than that of a Carbopol(®)-based hydrogel (HDG), and 6.72- to 17.55-fold (p<0.05) higher than that of LPG, with the same water content. Rat in vivo microdialysis showed that CPG produced sustained baicalin release, with superior pharmacokinetic parameters to those of HDG. Furthermore, cutaneous drug absorption was more efficient on rat abdominal skin, compared to that in the chest or scapular region. Effective fusion between the CPG lipid matrix and the stratum corneum may explain this enhancement of transdermal permeation. CPG containing TP therefore, achieved excellent transdermal drug delivery and good baicalin stability, indicating that this system represents a promising transdermal delivery vehicle.

Concepts: Protein, Pharmacology, Transdermal patch, Physical chemistry, Absorption, Pharmacokinetics, Cubic crystal system, Glycol ethers

0

In this article, we extend the simulated moving bed reactor (SMBR) mode of operation to the production of propylene glycol methyl ether acetate (DOWANOL™ PMA glycol ether) through the esterification of 1-methoxy-2-propanol (DOWANOL™ PM glycol ether) and acetic acid using AMBERLYST™ 15 as a catalyst and adsorbent. In addition, for the first time, we integrate the concept of modulation of the feed concentration (ModiCon) to SMBR operation. The performance of the conventional (constant feed) and ModiCon operation modes of SMBR are analyzed and compared. The SMBR processes are designed using a model based on a multi-objective optimization approach, where a transport dispersive model with a linear driving force for the adsorption rate has been used for modeling the SMBR system. The adsorption equilibrium and kinetics parameters are estimated from the batch and single column injection experiments by the inverse method. The multiple objectives are to maximize the production rate of DOWANOL™ PMA glycol ether, maximize the conversion of the esterification reaction and minimize the consumption of DOWANOL™ PM glycol ether which also acts as the desorbent in the chromatographic separation. It is shown that ModiCon achieves a higher productivity by 12-36% over the conventional operation with higher product purity and recovery.

Concepts: Ethanol, Adsorption, Acetic acid, Ester, Optimization, Propylene glycol, Cellulose acetate, Glycol ethers

0

The invention of new organic materials with high dielectric constants is of extreme importance for the development of organic-based devices such as organic solar cells. We report on a synthetic way to increase the dielectric constant of fullerene derivatives. It is demonstrated that introducing triethylene glycol monoethyl ether (teg) side chains into fulleropyrrolidines increases the dielectric constant by ∼46 percent without devaluation of optical properties, electron mobility and the energy level of the compound.

Concepts: Photon, Optics, Light, Organic chemistry, Solar cell, Photovoltaics, Dielectric, Glycol ethers