diethylene glycol dibenzoate toxicity

Durand A, Auzepy P, Hebert J, Trieu T. A study of mortality and urinary excretion of oxalate in male rats following acute experimental intoxication with diethylene glycol. 2021 Aug 3;9:709495. doi: 10.3389/fchem.2021.709495. lowest published toxic concentration: 4 mg/m 3 /2H/30W- intermittent: Tumorigenic: Carcinogenic by RTECS criteria Blood: Lymphoma including Hodgkin's disease . The DEG contained DEG (99.78%), EG (0.05%), and triethylene glycol (0.08%). March 2019 Molecular Weight. At the 2 and 5 g/kg doses, no changes in renal function were noted and only minor increases in vacuolization were present in both strains; the minor pathology noted in these groups did not approach the magnitude of vacuolar degeneration observed in the 10 g/kg DEG animals. Magnification 100 for all images. Weiner H, Richardon K. Metabolism of diethylene glycol in male rats. In: Bancroft J, Gamble M, editors. Federal government websites often end in .gov or .mil. Additionally, AST and ALT levels were significantly elevated to the same magnitude (6-fold for AST and 2-fold for ALT) in both strains at the 10 g/kg dose, with no increase at the lower doses in either strain. Periodic acid-Schiff staining for liver glycogen detection in DEG treated rats. There were no significant differences between the strains. Diethylene glycol (DEG; CAS RN 111-46-6) is primarily used as an industrial chemical, but is also found in certain consumer products, such as brake fluid and antifreeze, thereby allowing for possible consumer exposure (Marraffa et al., 2008).DEG has recently been involved in several mass epidemics of renal failure and death world-wide (O'Brien et al., 1998; Schier et al., 2013). As one important and related example, male Wistar rats have been shown to have increased sensitivity to ethylene glycol (EG)-induced nephrotoxicity, about double that of male F-344 rats (Cruzan et al., 2004). Values in the text represent the group mean value SEM. Diethylene glycol monobutyl ether (DGBE) is a colorless liquid. Clinical features: As such, these studies clearly demonstrated that Wistar and F-344 rats show equal sensitivity to DEG-induced toxicity, so either strain could be used in mechanistic studies or for health risk assessments related to DEG. Representative hematoxylin and eosin images at 48 h of liver tissue from both Wistar and F-344 rat strains for each of the treatment groups show little to no damage for rats treated with 0, 2 or 5 g/kg DEG, but substantial liver injury for rats treated with 10 g/kg DEG. Identification Product Name Diethylene Glycol (Reagent) Cat No. At 48 h, rats were anesthetized for blood collection and tissue procurement. Myers R, Fredenburgh J, Grizzle W. Carbohydrates. 4 and Table 3). Also, this study has shown that 10 g/kg DEG-induced liver damage manifested as severe glycogen depletion and centrilobular necrosis, and that it also followed a threshold response, much like the kidney toxicity, regardless of rat strain. 10 g/kg DEG causes severe liver glycogen depletion. Overall this study has concluded that both strains would be appropriate models to conduct DEG mechanistic studies or risk assessments. Cruzan G, Corley R, Hard G, Mertens J, McMartin K, Snellings W, Gingell R, Deyo J. Subchronic toxicity of ethylene glycol in Wistar and F-344 rats related to metabolism and clearance of metabolites. DEG has been shown to produce osmotic diuresis in laboratory animals (Lenk et al., 1989; Besenhofer et al., 2010) and in humans (Calvery and Klumpp, 1939), with a linear relationship between DEG dose and volume of urine produced (Lenk et al., 1989). eCollection 2021. Urine volume is increased in both F-344 and Wistar rat strains at 5 and 10 g/kg DEG doses (A and B). Liver to body weight ratios were not significantly increased in any of the DEG dose groups regardless of elevated plasma enzymes, strain, or DEG dose (Table 2). Both strains receiving 10 g/kg DEG were oliguric by 36 h (significantly lower urine volumes than controls) and had become an-uric by 48 h. Additionally at the high dose only, DEG-treated F-344 and Wistar rat kidneys appeared large, swollen, and weighed substantially more than the control kidneys. The site is secure. Following gavage at time 0, animals were housed in metabolic cages for 48 h for urine collection. Parameters determined from samples collected at 48 h post-treatment. Clin Toxicol (Phila). Samples of kidney tissue (~0. endstream endobj 1801 0 obj <>/Metadata 143 0 R/Names 1829 0 R/OpenAction 1802 0 R/Outlines 1854 0 R/PageLayout/SinglePage/PageMode/UseOutlines/Pages 1787 0 R/StructTreeRoot 224 0 R/Type/Catalog/ViewerPreferences<>>> endobj 1802 0 obj <> endobj 1803 0 obj <>/ExtGState<>/Font<>/ProcSet[/PDF/Text]>>/Rotate 0/StructParents 0/Tabs/S/Type/Page>> endobj 1804 0 obj <>stream Freundt KJ, Weis N. Transient renal impairment in rats after oral exposure to diethylene glycol. First, benzyl acid and diglycol with the weight ratio of 2: 1-1.1 are taken; then, protonic acid is taken as a catalyst, which has a weight 0.01-0.02 time of the . The increased glycogenolysis and subsequent glycogen breakdown would be expected to mobilize glucose, thereby increasing circulating blood glucose levels. Vascular congestion was noted in all groups and in both rat strains. A Toxicokinetics: The ePub format uses eBook readers, which have several "ease of reading" features 2011 Oct;123(2):374-83. doi: 10.1093/toxsci/kfr197. n=R#'N;mX6G#e[OL 86Il_q8>5) mUl@s 7*3itq"H4w{\c$u9Ey/,\f[Ost.o=>H: Renal injury was assessed primarily using BUN and creatinine levels as well as kidney to body weight ratios. Diethylene glycol. Vol. Epub 2011 Jul 29. Because none of these parameters were changed at the 2 and 5 g/kg doses, these data support a marked accumulation of an acidic species in the blood at the 10 g/kg DEG dose, most likely 2-HEAA (Besenhofer et al., 2011). 2-HEAA has been shown to be the acid metabolite responsible for inducing the metabolic acidosis (Besenhofer et al., 2010, 2011). DEG induced diuresis is most likely due to its hygroscopic nature (Laug et al., 1939), and DEG functions like many other alcohols producing diuretic effects upon initial consumption. A summary of the literature on DEG was compiled by systematically searching OVID MEDLINE and ISI Web of Science. 173, 1939. In that experiment, there were animals that reached a kidney DGA concentration of ~13 mmol/L, similar to what is reported in this study. Related Pages. Most recent studies have used the Wistar strain because of the known strain difference in ethylene glycol (EG) toxicity (Cruzan et al., 2004), and the historical idea that the renal damage from DEG might result from the metabolism to EG, which then would produce the renal damage. These experiments have demonstrated that DEG-induced kidney and liver toxicity and metabolic acidosis depict a steep threshold dose response; whereby, essentially no toxicity was observed at the lower 2 and 5 g/kg doses, but toxicity was substantial and severe at 10 g/kg dose. The invention discloses a method for preparing diethylene glycol dibenzoate ester, which relates to a process for preparing diethylene glycol dibenzoate ester (DEDB) which functions as a plasticizer of organic chemical products. Plasmas were analyzed for a basic metabolic panel, including markers of renal function (urea nitrogen [BUN] and creatinine), liver function (aspartate aminotransferase [AST] and alanine aminotransferase [ALT]), glucose, and electrolytes (sodium [Na+], potassium [K+], chloride [Cl], and calcium [Ca2+] by the Louisiana State University Health Sciences Center-Shreveport Clinical Laboratory. Schier JG, Hunt DR, Perala A, McMartin KE, Bartels MJ, Lewis LS, McGeehin MA, Flanders WD. Dose and strain-dependent decreases in urine pH in DEG-treated Wistar and F-344 rats (C and D). 5 and Table 3). They are based predominantly on reports following some epidemics of mass poisonings, which may underestimate toxicity. . Animals did not exhibit any gross behavioral signs of morbidity throughout the 48 h post-dosing period. 3) and were higher than the mean concentration (~5 mmol/L) reported previously in Wistar rats at the 10 g/kg dose (Besenhofer et al., 2011). Oral/Parenteral Toxicity: oral-rat LD50 2830 mg/kg American Industrial Hygiene Association Journal. Clin Toxicol (Phila). Organism Test Type Route Reported Dose (Normalized Dose) Effect Source; cat: LD50: oral: 3300mg/kg (3300mg/kg) Journal of Industrial Hygiene and Toxicology. Acute experimental poisoning by diethylene glycol acid base balance and histological data in male rats. DGA concentrations at 48 h in kidney tissue of Wistar and F-344 rats treated with DEG show no significant differences between the strains. Epub 2014 May 9. The urine was allowed to settle for 30 min on ice, and then one to two 1 mL aliquots of clean urine were transferred to microtubes and stored at 80 C until needed. %t"@5Cn:oFVr,C0`Y{6`O^ua{|.)_GPd3zTmx|C, Reports in the literature suggest a difference between the minimal toxic dose of DEG in humans and the apparent toxic dose in rats. Although recent studies have shown that EG and oxalate do not have significant roles in the renal damage from DEG (Besenhofer at al., 2010; Besenhofer et al., 2011), the present studies were needed to elucidate if a strain difference also exists with DEG toxicity. Besenhofer LM, Adegboyega PA, Bartels M, Filary MJ, Perala AW, McLaren MC, McMartin KE. Liver injury at the low doses in both strains was characterized by minor cytoplasmic reticulation coalescing to form minor microvesicular fatty changes; similar effects were also seen in a majority of the control rats from both strains (Fig. This site needs JavaScript to work properly. Both strains had undetectable DGA tissue concentrations in the 2 and 5 g/kg DEG dose groups. The dotted line indicates the limit of quantitation for the DGA method. The mobile phase consisted of 20 mmol/L sulfuric acid (pH 2.0, using 1 mol/L ammonia) containing 1% acetonitrile and was pumped at a flow rate of 1 mL/min for 18.5 min. chemicals not covered, or whether chemicals have pending IRIS toxicity values) may be directed to the U.S. EPA Office of Research and Development's National Center for Environmental Assessment, Superfund Health Risk Technical Support Center (513-569-7300), or OSRTI. 1 As alcohol with peculiar physicoche mical characte ristic s, it has seve ral uses in the industry . There are no available aquatic toxicity studies on diethylene glycol abietate; the OPPT Diethylene glycol, dibenzoate Ethanol, 2,2'-oxybis-, 1,1'-dibenzoate Ethanol, 2,2'-oxybis-, dibenzoate Oxydiethylene dibenzoate Superlist Name Diethylene glycol, dibenzoate Registry Numbers CAS Registry Number 120-55-8 FDA UNII YAI66YDY1C Other Registry Number 773104-50- System Generated Number 0000120558 Structure Descriptors InChI The metabolic pathway for DEG has been elucidated at toxic dose levels in male Wistar rats (Besenhofer et al., 2010, 2011). Diethylene glycol dibenzoate. Epub 2013 Nov 25. Additionally, urine pH was significantly decreased from 6 to 36 h in Wistar rats treated with 10 g/kg DEG, whereas in F-344 rats urine pH was decreased only from 6 to 24 h. A presumable explanation is that there is a larger amount of an acidic metabolite excreted in the urine of Wistar rats after DEG doses, even though there is no difference in blood metabolite levels between Wistar and F-344 rats. The present study has advanced beyond those findings by showing the strong threshold dose response in both Wistar and F-344 rats, where DEG toxicity was seen only in the 10 g/kg dose groups and no adverse effects were noted at 5 g/kg. The invention discloses a method for preparing diethylene glycol dibenzoate ester, which relates to a process for preparing diethylene glycol dibenzoate ester (DEDB) which functions as a plasticizer of organic chemical products. Diethylene glycol. In the current study, blood was collected at termination (48 h) to provide endpoint metabolic data, and showed no significant hyper-glycemia (data not shown). Gu Y, Wang GJ, Sun JG, Zhang XY, Sai Y. Diethylene glycol, dibenzoate. The clinical effects of DEG poisoning can be divided into three stages: The first phase consists of gastrointestinal symptoms with evidence of inebriation and developing metabolic acidosis. HHS Vulnerability Disclosure, Help The authors declare that there are no conflicts of interest. HW5}.7). Also, DGA is markedly accumulated in liver and kidney, as compared to the plasma DGA levels, of DEG-intoxicated rats (Besenhofer et al, 2011). At 48 h, the animals were anesthetized with sodium pentobarbital (50 mg/kg, i.p. OBrien K, Selanikio J, Hecdivert C, Placide M, Louis M, Barr D, Barr J, Hospedales J, Lewis M, Schwartz B, Philen R, St Victor S, Espindola J, Neddham L, Denerville K. Epidemic of pediatric deaths from acute renal failure caused by diethylene glycol poisoning. MeSH There was no difference between strains. In fact, the most recent DEG studies were done in male Wistar rats specifically to maximize the potential for a role of EG (calcium oxalate) in mediating the renal toxicity of DEG. Vol. 2021 Sep;59(9):810-821. doi: 10.1080/15563650.2021.1874403. Lenk W, Lohr D, Sonnenbichler J. Pharmacokinetics and biotransformation of diethylene glycol and ethylene glycol in the rat. )@il=O +@ tXQNsTuC`WY _m`P+/aEPR-#! Use water spray, alcohol-resistant foam, powder, carbon dioxide. Toxicol Sci. Data are represented as means SEM (n = 3 for Wistar (2 g/kg); n = 4 for all other groups). Jamison CN, Dayton RD, Latimer B, McKinney MP, Mitchell HG, McMartin KE. 1927 0 obj <>stream Water body should be given special attention. 1B). Greg M. Landry, Cody L. Dunning, [], and Kenneth E. McMartin. At 48 h, AST and ALT levels were significantly elevated in both rat strains, but only in animals treated with 10 g/kg DEG, with no elevation in animals treated with 2 or 5 g/kg (Table 2). eCollection 2020. Neurotoxic effects of nephrotoxic compound diethylene glycol. Benzo Flex 2-45 Benzoic acid, diester with diethylene glycol . The .gov means its official. For example, a composition with a fish LC value of 100 mg/L or greater may be . Data analysis and chromatogram processing was performed by Beckman Gold software (version 8.10). Ferrari L, Giannuzzi L. Clinical parameters, postmortem analysis and estimation of lethal dose in victims of a massive intoxication with diethylene glycol. 2010 Sep;117(1):25-35. doi: 10.1093/toxsci/kfq167. Glycogen depletion occurred initially in the centrilobular region and progressed outward, results similar to that observed in high dose DEG intoxication in our studies. Throughout the time course of the experiment, animals were monitored for behavioral signs indicative of morbidity, such as decreased food or water intake or decreased response to stimuli. Introduction. >('ya@cJIC@;ICCdS`}+ p("5vVDAu,oh((/7"* &}gQ05 9`&R{271i Ae_( x~hDb1jrP5'$D3J(=;*;m!CF6Q+)C55:&>gu%?H d_Z`;=}rm70W[i8JkO^;FHWgGO"bH,ji}`)^Dynr`V7Nke! Polyethylene glycol 100 dibenzoate; Polyoxyethylene (2) dibenzoate; Benzo Flex 2-45; Benzoic acid, diester with diethylene glycol; Benzoyloxyethoxyethyl benzoate; Dibenzoyldiethyleneglycol ester; Ethanol, 2,2'-oxybis-, dibenzoate; [ChemIDplus] Histological examination of livers from acetaminophen-treated animals, as well as from starved animals, reveals a substantial glycogen depletion that results from severe glutathi-one (GSH) depletion (Hinson et al., 1983). Toxicol Appl Pharmacol. Ethanol, 2,2'-oxybis- . Clin Toxicol (Phila). No increases in anion gap were observed at the 2 and 5 g/kg doses (Table 1). 1C) and from 6 to 24 h (Fig. Exposure to DGB was also found to affect lipid metabolism leading to increased lipid production and mobilization in a non-monotonic dose-related fashion. Every product and ingredient in Skin Deep gets a two-part score - one for hazard and one for data availability. The kidney DGA levels in this study were roughly 1015 times higher than the limit of quantitation (Fig. Clin Toxicol (Phila). In addition, the study provides key mechanistic insight by relating the magnitude of DGA tissue retention to the presence of toxic effects. Diethylene glycol is an organic liquid compound with the chemical structure: CH 2 OHCH 2 OCH 2 CH 2 OH. Discover 120-55-8 Textile Dyeing Auxiliaries 99% Purity DEG Dibenzoate Colorless from china factories, quality 120-55-8 Textile Dyeing Auxiliaries 99% Purity DEG Dibenzoate Colorless of Ecod Specialties(Wuhan) Co., Ltd. from china factories. Updated. Urine pH in the 2 and 5 g/kg dose groups returned to normal by 48 h. Urine pH was not measureable at 48 h in the 10 g/kg DEG-treated rats due to the oliguria or anuria. For each tissue, a 1 mm slice was fixed in 10% neutral buffered formalin. Diethylene glycol dibenzoate | C18H18O5 | CID 8437 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological . hbbd```b``S AD2 Dr`2LN@$BH#X6XDH2n69DZu15me=Xv 9JL#)|mJg}i@ Metabolic acidosis is one of the major characteristics of DEG poisoning in humans and animals (Alfred et al., 2005; Hebert et al., 1978; Heilmar et al., 1993), as noted by an increased anion gap and decreased blood bicarbonate and pH levels. %%EOF Previous studies have suggested that the nephrotoxic metabolite of DEG is DGA, which leads in vitro to ATP depletion, reactive oxygen species production, succinate dehydrogenase inhibition, and ultimately necrotic proximal tubule cell death (Landry et al., 2011, 2013). 2 DEG is . Since DEG has been shown to have dose-dependent diuretic effects (Lenk et al., 1989), urine volumes were measured from both rat strains at each time point. Treatment with DEG did not affect plasma calcium or glucose concentrations nor did it statistically change lactate levels (data not shown). Before Baj J, Forma A, Kobak J, Tyczyska M, Dudek I, Maani A, Teresiski G, Buszewicz G, Januszewski J, Flieger J. Int J Environ Res Public Health. Urine was collected in iced tubes at timed intervals up to 48 h. Metabolic cages were rinsed with water between collections. 2008. This metabolism has been shown to be necessary for the target damage to the kidney (Besenhofer et al., 2010). Tissues were examined with light microscopy by the LSUHSC-S Department of Pathology to visualize early pathophysiological changes as well as necrosis and/or apoptosis. }]K1"H*0K.N#1U@/:ss(HiT;I}YLc#b83`^qe;Jkl,e:BG!?+5vP)+z.5wTT[V(w)Y;l"{Q>M"'V>R5`%R/8@s3t=& :H=:DSxf6BUh;1A= ;_f=8t \5+LF:#kC;]~7XP mF0? It is miscible in water, ether, acetone, alcohol and ethylene glycol. At 48 h, blood pH, bicarbonate, and CO2 in the 10 g/kg dose groups were significantly decreased from 0 g/kg controls without a difference between the strains. Share Profile . i I$DZ d k`K3But1tmDX 2014 Jun;52(5):470-8. doi: 10.3109/15563650.2014.914527. Author manuscript; available in PMC 2017 Jan 14. Haz-Map. Alfred S, Coleman P, Harris D, Wigmore T, Stachowski E, Graudins A. 2020 Dec 15;2:586674. doi: 10.3389/ftox.2020.586674. Fomepizole for the treatment of pediatric ethylene and diethylene glycol, butoxyethanol, and methanol poisonings. An estimated BCF value of 120 was calculated for diethylene glycol dibenzoate (SRC), using an estimated log Kow of 3.04 (1,SRC) and a recommended regression-derived equation (2). Data are represented as means, DGA concentrations at 48 h in kidney tissue of Wistar and F-344 rats treated with DEG show no significant differences between the strains. Updated. At 48 h after dosing, both BUN (Fig. 12.4 Mobility in soil Metabolic acidosis was assessed using the parameters of blood pH, bicarbonate, CO2 and the calculated anion gap (Table 1). Male Wistar and Fischer-344 rats (Harlan, Indianapolis, IN) were each randomly placed into one of four treatment groups with four rats per group per strain, including a 0 g/kg control group, which received water by gavage, and three treatment groups, which received a single dose of either 2 g/kg, 5 g/kg, or 10 g/kg DEG by gavage. The LSU Health Sciences Center Ike Muslow Predoctoral Fellowship and the AstraZeneca Pharmaceuticals Graduate Student Fellowship provided stipend and research support for G.M. Diethylene glycol-induced toxicities show marked threshold dose response in rats, The publisher's final edited version of this article is available at, Diglycolic acid, Animal model, Risk assessment, Nephrotoxicity, Hepatotoxicity, Urine volume is increased in both F-344 and Wistar rat strains at 5 and 10 g/kg DEG doses (A and B). For more information about the substance, you may click one of the links below to take you to the relevant section: Program and regulatory information about this substance, including links to EPA applications/systems, statues/regulations, or . In the Panama epidemic, the ingested dose to produce renal failure was estimated as 0.36 g/kg (Sosa et al., 2014). Immediately after collection, the urine samples were vortexed and the volume and pH were recorded. DEG for gavage was provided by Shell Chemical LP (Houston TX) and analyzed for purity by gas chromatography (GC). HPLC separation (50 L injection) was performed on a Phalanx C18 5 m analytical column (250 mm 4.6 mm, Higgins Analytical) with a C18 guard column (Supelco). Pathology reports in this study showed that there was slight cytoplasmic reticulation in both rat strains at 0, 2, and 5 g/kg DEG doses. Toxicol Sci. If 1 g of kidney tissue is approximately equivalent to 1 mL, then the Wistar kidney DGA concentrations were approximately 17 mmol/L, and F-344 concentrations were approximately 10 mmol/L. Y { 6 ` O^ua { | ` WY _m ` P+/aEPR- # and! Richardon K. metabolism of diethylene glycol, butoxyethanol, and Kenneth E. McMartin lethal dose victims... 2830 mg/kg American Industrial Hygiene Association Journal quantitation ( Fig, diester diethylene... After collection, the animals were housed in metabolic cages for 48 h for urine.. Glycogen detection in DEG treated rats rats were anesthetized for blood collection tissue... 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Were examined with light microscopy by the LSUHSC-S Department of Pathology to visualize early pathophysiological changes well....Gov or.mil glycol acid base balance and histological data in male rats kidney DGA levels this., powder, carbon dioxide 50 mg/kg, i.p miscible in water, ether, acetone, alcohol and glycol... As well as necrosis and/or apoptosis weiner h, rats were anesthetized for blood and... R, Fredenburgh J, Gamble M, Filary MJ, Perala a, McMartin KE glycol in male.!

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