Diethylene glycol Information & Diethylene glycol Links at HealthHaven.com
advertise
add site
services
publishers
database
health videos
Bookmark and Share

search wiki for    ?
web dir firms image gallery news pdf wiki shop video 
about
toolbar
stats
live show
health store
more stuff
JOIN/LOGIN
Featured Results:
Diethylene glycol : Carcinogenic Potency Database
Diethylene glycol: Carcinogenic Potency Database
potency.berkeley.edu		  Glycol | Effects of propylene glycol | ethylene glycol
Glycol | Effects of propylene glycol | ethylene glycol
natural-health-informatio...		 GE CB-3565 Glycol | General Electric Chiller Ethylene Glycol
GE CB-3565 Glycol | General Electric Chiller Ethylene Glycol
soundimaging.com		 Antibody to Polyethylene glycol (PEG)
Antibody to Polyethylene glycol (PEG)
mainebiotechnology.com		 
 This article may require cleanup to meet Wikipedia's quality standards. Please improve this article if you can. (December 2009)
Diethylene glycol
Diethylene-glycol-chemical.png
IUPAC name
Other names diethylene glycol; ethylene diglycol; diglycol; 2,2'-oxybisethanol; 3-oxa-1,5-pentanediol;
dihydroxy diethyl ether
Identifiers
CAS number 111-46-6 Yes check.svgY
PubChem 8117
SMILES
Properties
Molecular formula C4H10O3
Molar mass 106.12 g/mol
Appearance Colorless liquid
Density 1.118 g/mL
Melting point

-10.45 °C
Boiling point

244-245 °C
Solubility in water miscible
Hazards
MSDS Diethylene-glycol MSDS
Related compounds
Related diols ethylene glycol, triethylene glycol
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Diethylene glycol (DEG) is an organic compound with the formula (HOCH2CH2)2O. It is a colorless, practically odorless, poisonous, viscous, and hygroscopic liquid with a sweetish taste. It is miscible in water, alcohol, ether, acetone and ethylene glycol.[1] DEG is a widely used solvent.[2]

Contents

[edit] Preparation

DEG is produced by the partial hydrolysis of ethylene oxide. Depending on the conditions, varying amounts of DEG and related glycols are produced. The resulting product is two ethylene glycol molecules joined by an ether bond.[3]

[edit] Structure of DEG and related polyols

Diethylene glycol is one of several glycols derived from ethylene oxide. Related to and coproduced with diethylene glycol are have the formula HO(CH2CH2(OCH2CH2)nOH. They are:

These compounds are all hydrophilic, more so than most diols, by virtue of the ether functionality.

[edit] Uses

DEG is used as a building block in organic synthesis, e.g. of morpholine and 1,4-dioxane. It is a solvent for nitrocellulose, resins, dyes, oils, and other organic compounds. It is a humectant for tobacco, cork, printing ink, and glue.[4] It is also a component brake fluid, lubricants, wallpaper strippers, artificial fog solutions, and heating/cooking fuel.[1] In personal care products (e.g. skin cream and lotions, deodorants) DEG is often replaced by selected diethylene glycol ethers. A dilute solution of diethylene glycol can also be used at a coolant; however, ethylene glycol is much more commonly used.

[edit] Toxicology

Despite the discovery of DEG’s toxicity in 1937 and its involvement in mass poisonings around the world, the information available regarding human toxicity is limited. Some authors suggest that minimum toxic dose is estimated at 0.14 mg/kg of body weight and lethal dose between 1 and 1.63 g/kg of body weight,[5] while some suggest that the LD50 in adults is of ~1 mL/kg,[1] and other suggest that this is the LD30.[3] Because of its adverse effects on humans, diethylene glycol is not allowed for use in food and drugs. The U.S. Code of Federal Regulations allows no more than 0.2% of diethylene glycol in polyethylene glycol when the latter is used as a food additive.[6]

Diethylene glycol has moderate acute toxicity in animal experiments. The LD50 for small mammals has been tested at between 2 and 25 g/kg, less toxic than its relative ethylene glycol but still capable of causing toxicity in humans. It appears diethylene glycol is more hazardous to humans than implied by oral toxicity data in laboratory animals.[1]

[edit] Toxicokinetics

Although there is limited information about toxicokinetics in humans, observations in mass poisonings and experimental studies suggest the following information:

[edit] Absorption and distribution

The principal method of absorption is through oral ingestion. Dermal absorption is very low, unless it is administered on broken or damaged skin. After ingestion, DEG is absorbed through the gastrointestinal tract and distributed by the bloodstream throughout the body, reaching peak blood concentrations occurring within 30 to 120 minutes. Once DEG reaches the liver, it is metabolized by enzymes.[1][5]

[edit] Metabolism and elimination

At first, scientists thought that DEG metabolized into ethylene glycol, but subsequent observations demonstrated there was no calcium oxalate crystal deposition at the kidneys. Rat models suggest that DEG is metabolized in the liver by enzyme NAD-dependent alcohol dehydrogenase (ADH) into a hydrogen ion, NADH and 2-hydroxyethoxyacetaldehyde (C4H8O3). Shortly after, 2-hydroxyethoxyacetaldehyde (C4H8O3) is metabolized by the enzyme aldehyde dehydrogenase (ALDH) into the weak acid 2-hydroxyethoxyacetic acid (HEAA) with chemical formula C4H8O4. Later on, HEAA leaves the liver through the bloodstream, being partially filtered at the kidneys for elimination.[1][5]

[edit] Mechanisms of toxicity

Based on available literature, scientists suggests that unmetabolized DEG and HEAA are partially reabsorbed through glomerular filtration. As a consequence, the concentrations of the weak acid HEAA and metabolites may cause renal delay, leading to metabolic acidosis and further liver and kidney damage.[1][5]

[edit] Symptoms

The symptoms of poisoning typically occur in three characteristic intervals:[1]

  • First phase: gastrointestinal symptoms such as nausea, vomiting, abdominal pain, and diarrhea. Some patients may develop early neurological symptoms like altered mental status, central nervous system depression and coma and mild hypotension.
  • Second phase: developed usually between 1 – 3 days after ingestion and dependent on dose ingested, patients develop metabolic acidosis, which causes acute kidney failure, oliguria, increasing serum creatinine concentrations, and later anuria. Other symptoms reported and secondary to acidosis and/or renal failure are hypertension, tachycardia, cardiac dysrhythmia, pancreatitis, hyperkalemia or mild hyponatremia.
  • Final phase: at least 5 – 10 days after ingestion, most of the symptoms are related to neurological complications like progressive lethargy, facial paralysis, dysphonia, dilated and nonreactive pupils, quadriplegia, and coma leading to death.

[edit] Treatment

Although it is not an approved procedure and there are no studies supporting successful removal of DEG, patients are subject to hemodialysis once diagnosis is made. Hemodialysis might be administered alone or with ethanol or fomepizole, which are competitive inhibitors of the enzyme NAD-dependent alcohol dehydrogenase (ADH):

  • With no medication: the low molecular weight and little or no plasma protein binding suggest that DEG should be removed through this method.[1]
  • With Fomepizole: an ADH inhibitor with 8,000 times more affinity than ethanol and with minimal adverse effects because maintains constant serum concentration.[3] However, it is a very expensive medication (approximately $3,000 U.S. dollars per treatment)[7]
  • With Ethanol: an ADH inhibitor used when fomepizole is not available. A constant high blood concentration of ethanol should be maintained to acceptably saturate the enzyme, which can cause ethanol intoxication. To avoid this adverse effect, frequent serum monitoring and dosage adjustment is necessary.[1]

For late diagnosis where ethanol or fomepizole is ineffective, because DEG has already been metabolized, hemodialysis becomes the only treatment available.[3]

[edit] Prognosis

Prognosis depends in prompt diagnosis and treatment due to the high mortality rate that DEG intoxication produces. Patients that survive but develop renal failure remain dialysis dependent. All patients are likely to suffer significant morbidity.[3]

[edit] Epidemiology

Diethylene glycol physical properties make it an excellent counterfeit for pharmaceutical-grade glycerine (also called glycerol) or propylene glycol, causing many deaths in different countries. It was also used by China as a component of cheap toothpaste and winemakers as an adulterant to create a "sweet" wine.[8][9]

[edit] 1937 – The Massengill Incident (United States)

Main article: Elixir Sulfanilamide

In 1937, S.E. Massengill Co. (a Tennessee drug company), manufactured sulfanilamide dissolved with diethylene glycol, to cover a liquid alternative of this drug. The company tested the new product, Elixir Sulfanilamide, for flavor, appearance and fragrance. At the time, the food and drugs law didn’t require toxicological analysis before releasing for sale. When 105 people died in 15 states during the months of September and October and the trail led back to the elixir, the toxic potential of this chemical was revealed.[10][11][12] This episode was the impetus for the Federal Food, Drug, and Cosmetic Act of 1938.[13] This law, though extensively amended in subsequent years, remains the central foundation of FDA regulatory authority to the present day.[14]

[edit] 1969 – South Africa

In Cape Town, South Africa, seven children died of renal failure after administration of over-the-counter sedative and developed vomiting, diarrhea and dehydration. Soon, patients started to present anuria, acidic breathing, hepatomegaly and unresponsiveness. Patients were treated with fluid hydration and correction of acidosis, but some were not able to survive. Postmortem examination revealed damage in kidneys and liver and laboratory testing found DEG instead of propylene glycol on the sedatives.[1][13]

[edit] 1985 – Spain

Patients being treated for burns, develop sudden anuric renal failure. Further investigations revealed that all patients were treated with topical silver sulfadiazine ointment that contained 7 g/kg of DEG. This event caused the death of five patients.[3][15][16]

[edit] 1985 - Wine scandal

During the month of July, Austrian wines were found to contain up to 1,000 parts per million of DEG, giving them the desirable sweetness characteristic. The news spread throughout the world, where many countries performed massive wine recalls. As a result, the U.S. Bureau of Alcohol, Tobacco and Firearms started to test all imported wine.

In November, The New York Times published a wine recall that the Federal Government released after the Bureau of Alcohol, Tobacco and Firearms tested 1,000 bottles. 45 Austrian, 5 German and 12 Italian wines tested positive for DEG. Some wines contained less than 10 parts per million of DEG, a small amount that could not be detected by laboratory analysis in Europe. This triggered the installation of more sensitive laboratory equipment in Banafi laboratories, Italy, and stronger alcohol regulations in Austria.[17][18][19]

After recalling millions of wine bottles, the Austrian Government had no idea how to destroy the product. During September 1986, the Ministry of Public Works started testing mixture of wine with salt to melt hazardous ice during winter. The primarily results revealed that the mixture was more effective than using salt alone.[20] The next year, an Australian electric power plant (Oesterreichischen Draukraftwerke) in Carinthia announced that technicians developed a way to produce energy burning 30 million liters of contaminated wine.[21]

[edit] 1986 – India

At a hospital in Bombay, India, patients were admitted to be treated for diverse health problems. Doctors prescribed glycerine for its osmotic diuretic effect, in contrast, patients started to develop renal failure. Fourteen patients received hemodialysis, but the treatment failed. The episode resulted in the death of 21 patients and the discovery of glycerin contaminated with 18.5% v/v of DEG.[1][13][22]

[edit] 1990 - Nigeria

During the summer months, 47 children were admitted to the Jos University teaching hospital, Nigeria, with anuria, fever and vomiting, that later developed renal failure and died. All children received acetaminophen syrup to treat upper respiratory infections related with malaria. Once physicians identified a paracetamol syrup, samples were shipped to Centers for Disease Control and Prevention (CDC), which identified DEG. It was assumed that DEG was used as a substitute of propylene glycol and this incident encouraged the Nigerian government to develop pharmaceutical quality control guidelines.[1][13][23][24]

[edit] 1990-1992 - Bangladesh

In Bangladesh between 1990 and 1992, 339 children developed kidney failure, and most of them died, after being given paracetamol (acetaminophen) syrup contaminated with diethylene glycol. The outbreak forced the government to ban the sale of paracetamol elixirs in December 1992, causing a decline of 53% in the admission of patients with renal failure and a 84% decline in admissions by unexplained renal failure.[25]

[edit] 1992 - Argentina

A propolis syrup manufactured by Huilen Laboratories in Buenos Aires, Argentina, contained between 24 and 66.5% DEG, caused the death of 29 persons.[26][27][28]

[edit] 1995-1996 - Haiti

In the poorest country in the Western Hemisphere, diseases are not recognized unless they become large or unusual. Between November 1995 and June 1996, almost 109 children admitted to the University Hospital in Port-au-Prince, Haiti, presented acute renal failure. Epidemiologists discovered consumption of Afebril or Valodon (acetaminophen preparations), manufactured by the same pharmaceutical. Due to the strong relationship between the company and the government, the Pan American Health Organization (PAHO); World Health Organization (WHO); the Caribbean Epidemiology Center, and the Centers for Disease Control and Prevention were invited to participate in the investigation.[23][29][30]

After collecting the samples and sending them to CDC for analysis, experimental trials revealed DEG presence in all the samples. Then, the manufacturer and the Haitian Minister of Health requested identification of the contaminated production lots and percentage of DEG in the syrups. With the available technology of the era, CDC determined that glycerin was used in the syrup preparation, but was contaminated with approximately 24% DEG.[23] Only 88 children deaths were recalled by doctors or had medical records. Nearly half of the victims were under the age of 2.[31]

Ending June 1996, the F.D.A. counterfeited glycerin to Chemical Trading and Consulting (a German broker), who bought 72 barrels of the syrup to Vos B.V., a Dutch company. Vos records revealed that the syrup had been bought from Sinochem International Chemicals Company through a German trader, Metall-Chemie. For July, the American Embassy in China contacted Sinochem and requested a list of Chinese glycerin makers, but the company refused to reveal the names. After a third attempt to find out who was the manufacturer, it was not until September 1996 that Sichonem provided a name, Tianhong Fine Chemicals Factory, and a phone number. While the F.D.A. tried to find out Tianhong’s address, Chinese officials were reluctant to become involved. One year and a half after the F.D.A. began to trace the poisonous shipment, agent Ted Sze, finally visited the Tianhong Fine Chemicals Factory in Dalian, northeastern China. But once he was inside, there was nothing to do: the plant had already been shut down. The Dutch authorities assessed a $250,000 fine against Vos B.V., by not alerting anyone when they tested the syrup and found impurities.[31]

[edit] 2006 - China

Wang Guiping discovered how easy it was to enter China’s pharmaceutical supply business and earn extra money. Records also revealed that to fool buyers, Wang falsified his license and laboratory analysis reports.

Wang declared that after making the first order of counterfeit syrup, he swallowed some of it. Once verifying that he was fine, he shipped it to Qiquihar No. 2 Pharmaceutical in 2005. Some time later, Wang found a reference to diethylene glycol in a chemical book. After manufacturing a second batch of syrup containing diethylene glycol for Qiquhar Pharmaceutical, no taste-test was performed. The counterfeit syrup ended in ampules of Amillarisin A, a medication for gall bladder problems; special pediatric enema fluid; blood vessel disease injections; intravenous pain reliever; and an arthritis medication.

In April 2006, the Guangdong Province Hospital of Guangzhou began administering Amillarisin A to their patients. Soon thereafter, patients died after receiving the medication. Mr. Wang was caught and Qiquihar was shut down by the authorities. Besides Wang, five employees of Qiquihar were prosecuted.[32]

[edit] 2006 - Panama

Ending September 2006, the Arnulfo Arias Madrid Hospital at Panama City was getting full with patients with contradictory symptoms. The symptoms seemed to match with Guillain-Barré syndrome, but these patients were also losing their ability to urinate, symptom not related to Guillain-Barré. The death rate of this mysterious illness was near 50%, when hospital management decided to isolate all the patients with the illness in a large room and doctors could compare notes and theories. Soon patients from other parts of the country started to arrive at hospitals. Doctors had no idea what was happening: the mysterious illness was attacking elderly citizens with hypertension and diabetes pressure history. About half was receiving Lisinopril (a blood pressure medicine) and many did not remember clearly if they had been taking other drugs. Suspecting something wrong with Lisinopril, the medicine was pulled out from the pharmacies[32] while the U.S. Food and Drug Administration conducted lab analyses, revealing that the blood pressure drug was safe and CDC epidemiologists were invited participate.[23]

When a patient admitted by a heart attack developed the mysterious illness at the hospital, Dr. Nestor Sosa, an infectious disease specialist, analyzed the medical record: Because patients treated with Lisinopril developed a cough (common side effect of ACE inhibitor), they were prescribed a expectorant.[32] Immediately, biological samples and the syrup were sent by jet to CDC for analysis. When urine analyses for a series of metals, pesticides or their metabolites resulted false, CDC scientists recalled Nigeria and Haiti incidents.. The CDC employed modern laboratory equipment to analyze the samples and confirm the results: the samples contained approximately 8% v/v DEG. Later on, raw glycerin was analyzed and results revealed 22.2% v/v DEG.[23]

Panamanian Government made nationwide campaign, collecting around 6,000 cough syrup and other three products manufactured by the Social Security Laboratories with the tainted glycerin.[33] The forty-six barrels of syrup were bought by the Social Security through a Panamanian middleman, Grupo Comercial Medicom, who bought the product from Rasfer Internacional, a Spanish company. In fact, Rasfer received the product from CNSC Fortune Way, who in turn bought it to Taixing Glycerine Factory. At the request of the United States, the State Food and Drug Administration of China investigated Taixing Glycerine Factory and CNSC Fortune Way, but the agency concluded that it is not under their jurisdiction because the factory is not certified to make medicine.[32][34]

Taixing sold the syrup as “TD glycerin”, wording that neither Chinese inspectors nor Spanish medical authorities comprehended. Unfortunately, Taixing used “TD” for the Chinese word “tidai” (pronounced tee-die), meaning “substitute”.[32] A New York Times reporter tried to obtain a comment from CNSC Fortune Way at the CPhI worldwide (the world’s largest annual pharmaceutical convention) held in Milan, Italy, during 2007, but their representatives refused to comment.[35]

In August 2009, the Supreme Court decided to send the diethylene glycol file to the Public Ministry for an extension.[36] The following month, the Toxicology Department of the Institute of Legal Medicine and Forensic Science published a list of 1,155 names whose medicine bottles tested positive for DEG. Only approximately 3,000 bottles had been analyzed from the total 6,000 bottles collected. The fiscal attorney urged affected citizens to approach the Public Ministry to update the official legal file and for further medical analysis.[33] Two months later, findings revealed that 145 were proven to die by DEG intoxication, but the DA still has to investigate 953 demands.[36]

The New York Times reported that Taixing was closed by the Chinese government and CNSC Fortune Way was never sanctioned, in fact, Fortune Way is owned by the government.[35] In Spain, Rasfer International declared in bankruptcy after the lawyer of Medicom filed a lawsuit by $400 million dollars during July 2008.[37] Spanish authorities are prosecuting Asunción Criado, general manager of Rasfer Internacional, S.A., and await Panamanian citizens, René Luciani (former Social Security Director) and Jéssica Rodríguez (former Purchase National Director) for their hearings. Meanwhile, in Panama, De la Cruz, legal representative of Medicom remains in jail pending a trial. Other 17 persons have also been charged related to this incident. Panama awaits the extradition of Criado for her hearing.[38]

Panama’s case made CDC set standardized methodology for DEG identification, hoping to have more timely response in future events. The agency also identified urinary DEG as a biomarker for DEG exposures[23]. The United States Food and Drug Administration also issued an Industry Guidance Document “intended to alert pharmaceutical manufacturers, pharmacy compounders, repackers, and suppliers to the potential public health hazard of glycerin contaminated with diethylene glycol (DEG)” and recommending appropriate testing procedures for use of glycerin.[39]

[edit] 2007 - worldwide toothpaste incident

The mass recall of four different medicines in Panama taught citizens that DEG is harmful. In May 2007, a Panamanian named Eduardo Arias discovered a 59-cent toothpaste was labeled as containing DEG. Panamanian officials traced the toothpaste to a local company in Colon Free Zone. In fact, the company bought the product in China and had already re-exported toothpaste to Costa Rica, Dominican Republic and Haiti, making Panama kick off a local warning.[40][41][42] For the end of the month, the Chinese government committed to investigate the “supposedly” tainted toothpaste that had been recalled in Panama and Dominican Republic, but stated that, as per an essay written in 2000, a toothpaste containing 15.6% was not dangerous.[43]

For June 1, 2007, the FDA warned consumers to avoid toothpaste from China, although there was no information if these toothpastes had already entered the US, and started testing any imported Chinese toothpaste.[44][45] Days later, Colgate-Palmolive found counterfeit toothpaste with its name, which contaminated with DEG and were found at dollar-type discount stores in New York, New Jersey, Pennsylvania and Maryland. The toothpaste was labeled as “Manufactured in South Africa” and contained misspellings like "isclinically" "SOUTH AFRLCA" and "South African Dental Assoxiation".[46][47] Although there were no reports of anyone harmed, several people in eastern US reported experiencing headaches and pain after using the product.[48] It was later discovered that a great number of tubes with poison ended up in hospitals for mentally ill, prisons, juvenile detention centers, other hospitals and many other state institutions.[49]

In July, England detected a counterfeit Sensodyne toothpaste on a sale at a car boot in Derbyshire.[50] Soon, authorities in Belize, Canada, Mozambique, Saudi Arabia, New Zealand, Spain, Italy, Japan, Ireland and an Indianapolis hotel supplier that distributed Chinese toothpaste in Barbados, Belgium, Bermuda, Britain, Canada, Dominican Republic, France, Germany, Ireland, Italy, Mexico, Spain, Switzerland, Turks and Caicos, the United Arab Emirates and United States were also recalling Chinese made toothpaste. What began as a local alert revealed a global problem in more than thirty countries and involving more than thirty brands.[51] The world outcry made Chinese officials ban the practice of using diethylene glycol in toothpaste.[52]

[edit] 2008 - Nigeria

Ending November, infants started to die after developing unexplained fevers and vomiting. Investigations revealed that all had taken a medicine called “My Pikin Baby”, a teeth mixture tainted with diethylene glycol. The poison had caused the death of at least 84 Nigerian children between ages 2 months and 7 years.[53][54]

The Nigerian government traced the diethylene glycol to an unlicensed chemical dealer in Lagos, who sold it to a local pharmaceutical manufacturer. Barewa Pharmaceuticals, was shut down and pulled off the shelves the tainted product. They also arrested 12 people in connection with the incident. Being the second incident involving counterfeit glycerine, the National Agency For Food And Drug Administration and Control (NAFDAC) has become zero-tolerant against counterfeits.[55][56][57]

[edit] Restrictions

Australian government does not allow DEG as a food additive; it is only allowed less than 0.25% w/w of DEG as an impurity of polyethylene glycol (PEG)[58] even in toothpaste.[35] [59]

[edit] See also

[edit] References

  1. ^ a b c d e f g h i j k l m Schep LJ, Slaughter RJ, Temple WA, Beasley DM (July 2009). "Diethylene glycol poisoning". Clin Toxicol (Phila) 47 (6): 525–35. doi:10.1080/15563650903086444. ISSN 1556-3650. PMID 19586352. 
  2. ^ Siegfried Rebsdat and Dieter Mayer "Ethylene Glycol” in Ullmann’s Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a10_101.
  3. ^ a b c d e f Marraffa JM, Holland MG, Stork CM, Hoy CD, and Hodgman MJ. (November 2008). "Dietylene Glycol: Widely Used Solvent Presents Serious Poisoning Potential.". J Emerg Med. 35 (4): 401–406. ISSN 0736-4679. PMID 18024066. 
  4. ^ O’Neil M. The Merck Index. 14th ed. Whitehouse Station, NJ: Merck & Co; 2006.
  5. ^ a b c d Kraut JA, Kurtz I. (January 2008). "Toxic alcohol ingestions: clinical features, diagnosis, and management.". Clin J Am Soc Nephrol 3 (1): 208–225. ISSN 1555-9041. PMID 18045860. 
  6. ^ ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN: Polyethylene glycol, Code of Federal Regulations, Title 21, Vol.3, Part 172, Sec. 172.820, Revised as of April 1, 2006
  7. ^ http://intmedweb.wfubmc.edu/blurbs/overdoses/methanol.html Anonymous author. Internal Medicine Residency Program of the College of Medicine of Wake Forest University, North Caroline, U.S.A. Retrieved December 8, 2009.
  8. ^ van der Linden-Cremers PM, Sangster B (Sep 28 1985). "Medical sequelae of the contamination of wine with diethylene glycol" (in Dutch) (Free full text). Ned Tijdschr Geneeskd 129 (39): 1890–1. ISSN 0028-2162. PMID 4069248. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+111-46-6. 
  9. ^ Authorities warn against using some toothpastes, GulfNews, Published 04/06/2007
  10. ^ http://www.fda.gov/downloads/AboutFDA/WhatWeDo/History/Origin/ucm125604.doc Ballentine, C. "Taste of Raspberries, Taste of Death - The 1937 Elixir Sulfanilamide Incident. FDA Consumer Magazine, June 1981.
  11. ^ "Medicine: Post-Mortem". Time magazine. December 20, 1937. http://www.time.com/time/magazine/article/0,9171,758704,00.html. Retrieved 2009-07-19. "Then, two months ago, fatality knocked at its door. A new mixture of a new drug (sulfanilamide) with a new solvent (diethylene glycol), which Dr. Massengill's salesmen sold as Elixir Sulfanilamide-Massengill, was discovered to be killing its users" 
  12. ^ "Wallace Reveals How Federal Agents Traced Elixir to Halt Fatalities". New York Times. November 26, 1937. http://select.nytimes.com/gst/abstract.html?res=F40C15F93B59177A93C4AB178AD95F438385F9. Retrieved 2009-07-20. "A graphic story of a race against death from "elixir sulfanilamide," carried on by the Food and Drug Administration in fifteen States from Virginia to California, a race not won until ninety-three persons had died after taking the lethal dose, was told by Secretary Wallace today in a report responding to Senate and House resolutions." 
  13. ^ a b c d Wax PM. (Mar 1995). "Elixirs, diluents, and the passage of the 1938 Federal Food, Drug and Cosmetic Act" (Free full text). Ann Intern Med 122 (6): 456–61. ISSN 0003-4819. PMID 7856995. http://www.annals.org/cgi/pmidlookup?view=long&pmid=7856995. 
  14. ^ http://www.fda.gov/AboutFDA/WhatWeDo/History/Origin/ucm054819.htm The History of FDA at FDA.gov
  15. ^ Schier JG, Rubin CS, Miller D, Barr D, McGeehin MA. (July 2009). "Medication-associated diethylene glycol mass poisoning: A review and discussion on the origin of contamination". J Public Health Policy 30 (2): 127–143. ISSN 0197-5897. PMID 19597445. http://www.palgrave-journals.com/jphp/journal/v30/n2/fig_tab/jphp20092t1.html. 
  16. ^ Cantarell MC, Fort J, Camps J, Sans M, Piera L (Mar 1987). "Acute intoxication due to topical application of diethylene glycol". Ann Intern Med 106 (3): 478–9. ISSN 0003-4819. PMID 3813252. 
  17. ^ http://www.nytimes.com/1985/11/01/us/popular-wines-found-to-hold-toxic-chemical.html Molotsky, I. "Popular Wines found to hold toxic chemical." The New York Times. November 1, 1985. Retrieved December 8, 2009.
  18. ^ http://www.nytimes.com/1985/08/02/world/scandal-over-poisoned-wine-embitters-village-in-austria.html Tagliabue, J. "Scandal over poisoned wine embitters village in Austria." The New York Times. August 2, 1985. Retrieved December 8, 2009.
  19. ^ http://www.ttb.gov/industry_circulars/archives/1986/86-13.html Bureau of Alcohol, Tobbacco, and Firearms. Industry Circular No. 86-13. October 6, 1986. Retrieved December 8, 2009.
  20. ^ http://news.google.com/newspapers?id=le8VAAAAIBAJ&sjid=HxQEAAAAIBAJ&pg=4847,2789108&dq=austria+diethylene+glycol+wine&hl=en "Tainted wine clear roads." Wilmington Morning Star. December 22, 1986. Retrieved December 9, 2009.
  21. ^ http://pqasb.pqarchiver.com/thestar/access/472561821.html?dids=472561821:472561821&FMT=ABS&FMTS=ABS:FT&type=current&date=Feb+27%2C+1987&author=Reuter&pub=Toronto+Star&desc=Austrian+power+plant+to+burn+%27bad%27+wine&pqatl=google Reuter. "Austrian power plant to burn 'bad' wine." February 27, 1987. Retrieved December 9, 2009
  22. ^ Pandya SK (Jul 9 1988). "Letter from Bombay. An unmitigated tragedy". BMJ 297 (6641): 117–9. doi:10.1136/bmj.297.6641.117. ISSN 0959-8138. PMID 3408933. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=3408933. 
  23. ^ a b c d e f Barr DB, Barr JR, Weerasekera G, Wamsley J, Kalb SR, Sjödin A, Schier JG, Rentz ED, Lewis L, Rubin C, Needham LL, Jones RL, Sampson EJ. (Jul-Aug 2007). "Identification and quantification of diethylene glycol in pharmaceuticals implicated in poisoning epidemics: an historical laboratory perspective.". J Anal Toxicol 31 (6): 295–303. ISSN 0146-4760. PMID 17725874. http://www.ingentaconnect.com/content/pres/jat/2007/00000031/00000006/art00001?token=004714316ade275c277b422c4b464c48283424456e7675592f653b2a2d3a7c4e7247704. 
  24. ^ Okuonghae HO, Ighogboja IS, Lawson JO, Nwana EJ (1992). "Diethylene glycol poisoning in Nigerian children" (Free full text). Ann Trop Paediatr 12 (3): 235–8. ISSN 0272-4936. PMID 1280035. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+103-90-2. 
  25. ^ SchHanif M, Mobarak MR, Ronan A, Rahman D, Donovan JJ Jr, Bennish ML. (July 1995). "Fatal renal failure caused by diethylene glycol in paracetamol elixir: the Bangladesh epidemic". BMJ 311 (6997): 88–91. PMID 7613408. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2550149/pdf/bmj00600-0022.pdf. 
  26. ^ Ferrari LA, Giannuzzi L (Oct 4 2005). "Clinical parameters, postmortem analysis and estimation of lethal dose in victims of a massive intoxication with diethylene glycol". Forensic Sci Int 153 (1): 49–51. doi:10.1016/j.forsciint.2005.04.038. ISSN 0379-0738. PMID 15979833. 
  27. ^ Schep LJ, Slaughter RJ (Dec 20 2005). "Comments on diethylene glycol concentrations". Forensic Sci Int 155 (2-3): 233. doi:10.1016/j.forsciint.2005.08.001. ISSN 0379-0738. PMID 16171962. 
  28. ^ http://nl.newsbank.com/nl-search/we/Archives?p_product=AK&s_site=ohio&p_multi=AK&p_theme=realcities&p_action=search&p_maxdocs=200&p_topdoc=1&p_text_direct-0=0EB62E565363C36E&p_field_direct-0=document_id&p_perpage=10&p_sort=YMD_date:D&s_trackval=GooglePM "Toll reaches 20 in tonic poisoning." Akron Beacon Journal (OH). August 22, 1992. Retrieved December 8, 2009.
  29. ^ O'Brien KL, Selanikio JD, Hecdivert C, Placide MF, Louis M, Barr DB, Barr JR, Hospedales CJ, Lewis MJ, Schwartz B, Philen RM, St Victor S, Espindola J, Needham LL, Denerville K. (Apr 1998). "Epidemic of pediatric deaths from acute renal failure caused by diethylene glycol poisoning" (Free full text). JAMA 279 (15): 1175–80. doi:10.1001/jama.279.15.1175. ISSN 0098-7484. PMID 9555756. http://jama.ama-assn.org/cgi/pmidlookup?view=long&pmid=9555756. 
  30. ^ "[http://www.cdc.gov/mmWR/PDF/wk/mm4530.pdf Fatalities Associated with Ingestion of Diethylene Glycol-Contaminated Glycerin Used to Manufacture Acetaminophen Syrup — Haiti, November 1995–June 1996]" (Free full text). Morbidity and Mortality weekly report. August 1996. http://www.cdc.gov/mmWR/PDF/wk/mm4530.pdf. 
  31. ^ a b Bogdanich, W. (June 2007). "FDA Tracked Poisoned Drugs, but Trail went cold in China.". The New York Times. http://www.nytimes.com/2007/06/17/health/17poison.html?_r=1&pagewanted=print. 
  32. ^ a b c d e Bogdanich, W and Hooker, J. (June 2007). "From China to Panama, a trail of Poisoned Medicine.". The New York Times. http://www.nytimes.com/2007/05/06/world/americas/06poison.html?pagewanted=print. 
  33. ^ a b Otero, J. (Sept 2009). "Aumentan Envenenados con Dietilene Glycol". http://mensual.prensa.com/mensual/contenido/2009/09/18/hoy/panorama/1927591.asp. 
  34. ^ Rentz ED, Lewis L, Mujica OJ, Barr DB, Schier JG, Weerasekera G, Kuklenyik P, McGeehin M, Osterloh J, Wamsley J, Lum W, Alleyne C, Sosa N, Motta J, Rubin C. (Oct 2008). "Outbreak of acute renal failure in Panama in 2006: a case-control study" (Free full text). Bull World Health Organ 86 (10): 749–56. doi:10.2471/BLT.07.049965. ISSN 0042-9686. PMID 18949211. http://www.scielosp.org/scielo.php?script=sci_arttext&pid=S0042-96862008001000010&lng=en&nrm=iso&tlng=en. 
  35. ^ a b China's Unwatched Drug Makers. October 2007. http://video.nytimes.com/video/2007/10/31/world/1194817122573/china-s-unwatched-drug-makers.html?scp=1&sq=China%27s%20Unwatched%20Drug%20Makers&st=cse. 
  36. ^ a b Otero, J. (Aug 2009). "Caso dietilene glycol puede viciarse: Troitiño". http://mensual.prensa.com/mensual/contenido/2009/08/25/hoy/panorama/1900108.asp. 
  37. ^ Perez, R. (July 2008). "Rasfer Internacional se declara en bancarrota.". http://mensual.prensa.com/mensual/contenido/2008/07/12/hoy/panorama/1439083.html. 
  38. ^ Irujo, J. (Jul 2009). "Panamá bloquea el proceso español por el caso del jarabe asesino". http://www.elpais.com/articulo/sociedad/Panama/bloquea/proceso/espanol/caso/jarabe/asesino/elpepisoc/20090731elpepisoc_9/Tes?print=1. 
  39. ^ http://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/ucm070347.pdf Guidance for Industry - Testing of Glycerin for Diethylene Glycol
  40. ^ Bogdanich, W.; McLean, R. "Poisoned Toothpaste in Panama Is Believed to Be From China", New York Times, May 19, 2007.
  41. ^ "China investigating toothpaste containing potentially deadly chemical". International Herald Tribune. 2007-05-22. http://www.iht.com/articles/ap/2007/05/22/asia/AS-GEN-China-Tainted-Toothpaste.php. Retrieved 2007-05-22. 
  42. ^ "U.S. checking all toothpaste imports from China". CNN. 2007-05-23. http://www.cnn.com/2007/HEALTH/05/23/china.toothpaste.reut/index.html. Retrieved 2007-05-23. 
  43. ^ Xiaomin, X and Hongyi, W. (2007-05-24). "Gov't probes 'tainted toothpaste' case". China Daily. http://www.chinadaily.com.cn/china/2007-05/24/content_879179.htm. Retrieved 2009-12-10. 
  44. ^ Bogdanich, W. "Toxic Toothpaste Made in China Is Found in U.S. ", New York TImes, June 2, 2007.
  45. ^ U.S. Food and Drug Administration Press Release. "FDA Advises Consumers to Avoid Toothpaste From China Containing Harmful Chemical. FDA Detains One Contaminated Shipment, Issues Import Alert", June 1, 2007.
  46. ^ Colgate Palmolive Company Press Release. "Counterfeit Colgate Toothpaste Found", June 14, 2007.
  47. ^ U.S. Food and Drug Administration Press Release. "Counterfeit Colgate Toothpaste Found", June 14, 2007.
  48. ^ 7online.com: Toothpaste recall expands 6/18/07
  49. ^ Bogdanich, W. "Wider Sale Is Seen for Toothpaste Tainted in China ", New York Times, June 28, 2007.
  50. ^ BBC NEWS | Business | Toxin found in fake UK toothpaste
  51. ^ "Tainted toothpaste across the world", New York Times, September 30, 2007. http://www.nytimes.com/imagepages/2007/09/30/world/20071001_PANAMA_GRAPHIC.html
  52. ^ Bogdanich, W. "The Everyman Who Exposed Tainted Toothpaste ", New York Times, October 1, 2007.
  53. ^ News.yahoo.com Nigeria child deaths from tainted syrup rise to 84
  54. ^ Nigeria child deaths from tainted syrup rise to 84
  55. ^ [1]
  56. ^ http://www.nytimes.com/2009/02/07/world/africa/07nigeria.html
  57. ^ http://www.nafdac.gov.ng/index.php?option=com_content&view=article&id=72:nafdac-negotiates-state-of-the-art-anti-counterfeiting-equipment&catid=51:press-statements&Itemid=113
  58. ^ http://www.nicnas.gov.au/Publications/CAR/Other/DEG_Hazard_Assessment_Report_PDF.pdf
  59. ^ Australian Competition and Consumer Commission. "Toothpaste containing more than 0.25 per cent by weight of diethylene glycol (DEG)". http://www.accc.gov.au/content/index.phtml/itemId/794351. Retrieved 1 December 2009. 

[edit] References

  • Merck Index, 12th Edition, 3168.

[edit] External links

Retrieved from "http://en.wikipedia.org/wiki/Diethylene_glycol"



Product Results (view all...)

search wiki for    ?
web dir firms image gallery news pdf wiki shop video 



↑ top of page ↑about thumbshots