Chlorohydrins
Ethylene Chlorohydrin
Ethylene Dichlorides
Exposure to trichloroethylene II. Metabolites in blood and urine. (1/52)
Fifteen men were exposed to trichloroethylene (TRI) in three different ways with regard to the concentration of TRI in the air as well as exercise on a bicycle ergometer. The total amount of TRI supplied and taken up by each person was measured. The concentrations of trichloroethanol (TCE) and trichloroacetic acid (TCA) were determined in blood and urine. In spite of large differences in uptake, there were only small differences in the concentration of TCA in blood during the day of exposure. There was a large scatter for the values of TCA in urine within each group. The concentration of TCE in arterial blood increased during exposure. Thereafter the concentrations were almost constant for 2 h and differed among the groups. These results can be interpreted as being due to balanced rates of the formation and elimination of TCE. The levels mentioned were related to the uptake of TRI. The same was found for the rate of excretion of TCE in urine when calculations were made from the morning sample obtained the day after exposure. (+info)Mutagenicity of chloroacetaldehyde, a possible metabolic product of 1,2-dichloroethane (ethylene dichloride), chloroethanol (ethylene chlorohydrin), vinyl chloride, and cyclophosphamide. (2/52)
We have previously described a very sensitive and efficient bacterial test designed to detect chemical carcinogens as mutagens. Chloroacetaldehyde is mutagenic in this system and is of interest because it is a possible metabolite in mammals of the large volume industrial chemicals 1,2-dichloroethane (ethylene dichloride) (3.5 billion kg/yr, U.S.) and vinyl chloride (2.5 billion kg/yr, U.S.), and of the antineoplastic agent cyclophosphamide. Chloroacetaldehyde reverts a new Salmonella bacterial tester strain (TA100). Chloroacetaldehyde is shown to be hundreds of times more effective in reversion of TA100 than is chloroethanol (ethylene chlorohydrin), a known metabolic precursor of chloroacetaldehyde and a possible metabolite of dichloroethane and vinyl chloride, or than vinyl chloride, which is itself mutagenic for TA100. Chloroethanol is shown to be activated by rat (or human) liver homogenates to a more highly mutagenic form with reversion properties similar to chloroacetaldehyde. Reversion properties of cyclophosphamide after in vitro metabolic activation suggest that chloroacetaldehyde is not the active mutagenic form of this antineoplastic drug. (+info)Isolation and characterization of 2,3-dichloro-1-propanol-degrading rhizobia. (3/52)
2,3-Dichloro-1-propanol is more chemically stable than its isomer, 1, 3-dichloro-2-propanol, and is therefore more difficult to degrade. The isolation of bacteria capable of complete mineralization of 2, 3-dichloro-1-propanol was successful only from enrichments at high pH. The bacteria thus isolated were found to be members of the alpha division of the Proteobacteria in the Rhizobium subdivision, most likely Agrobacterium sp. They could utilize both dihaloalcohol substrates and 2-chloropropionic acid. The growth of these strains in the presence of 2,3-dichloro-1-propanol was strongly affected by the pH and buffer strength of the medium. Under certain conditions, a ladder of four active dehalogenase bands could be visualized from this strain in activity gels. The enzyme involved in the complete mineralization of 2,3-dichloro-1-propanol was shown to have a native molecular weight of 114,000 and consisted of four subunits of similar molecular weights. (+info)The entry of alpha-chlorohydrin into body fluids of male rats and its effect upon the incorporation of glycerol into lipids. (4/52)
The rate of entry of alpha-chlorohydrin into rat rete testis fluid has been studied using the 14-C and 36-Cl-labelled compounds. The alpha-chlorohydrin crosses the blood-testis barrier and the concentration of radioactivity in rete testis fluid attained blood levels within 45 min. Within 3 hr of a single injection of [14-C] alpha-chlorohydrin, radioactivity was widely distributed in body fluids, and was present in the lipids of the brain, testis, epididymis and epididymal fat pads. No radioactivity was found in tissue lipids following the administration of [36-Cl] alpha-chlorohydrin, which suggests that dechlorination of this compound occurs before its incorporation. Neither a single high dose nor repeated low doses of alpha-chlorohydrin induced changes in the incorporation of [14-C] glycerol into lipids of the brain, testis, epididymis and epididymal fat pads. (+info)Purification and structure of the major product obtained by reaction of NADPH and NMNH with the myeloperoxidase/hydrogen peroxide/chloride system. (5/52)
The first spectrophotometric study of the reaction of the myeloperoxidase/H2O2/Cl- system with NADPH and NMNH showed that the reaction products were not the corresponding oxidized nucleotides and that modifications would take place on the nicotinamide part of the molecule [Auchere, F. & Capeillere-Blandin, C. (1999) Biochem. J. 343, 603-613]. In this report, in order to obtain more precise information on the structural modifications and mechanism of the reaction, we focus on the purification and isolation of products derived from NADPH and NMNH by RP-HPLC. Electrospray ionization mass spectra indicated that the relative height of the peaks reflected that of the natural isotopic abundance of 35Cl and 37Cl, providing evidence that the products derived from NADPH and NMNH were monochlorinated. Moreover, calculated masses revealed the 1 : 1 addition of HOCl to the molecule. Various 1D and 2D NMR experiments provided data for the assignments of the chemical shifts of protons and carbons and the coupling constants of the protons of the chlorinated nucleotides. Further NOESY experiments allowed the characterization of the spatial structure of the chlorinated product and showed that trans HOCl addition occurred at the C5=C6 carbon double bond of the nicotinamide ring, leading to a chlorohydrin. (+info)Mutagenic potential of bisphenol A diglycidyl ether (BADGE) and its hydrolysis-derived products in the Ames Salmonella assay. (6/52)
The mutagenicity of bisphenol A diglycidyl ether (BADGE), its first and second hydrolysis products (the diol epoxide and bis-diol of BADGE, respectively) and the bis-chlorohydrin of BADGE were investigated using the Ames Salmonella assay with strains TA98, TA100, TA1535 and TA1537. The assays were performed in the absence and presence of various concentrations of rat liver S9 fraction. The results obtained confirm the mutagenic power of BADGE in strains TA100 and TA1535 and show a positive response to the diol epoxide of BADGE in these strains, although the latter compound was approximately 10 times less potent than the former. A lack of mutagenic activity of the bis-diol of BADGE and the chlorohydrin under study is also shown. These findings suggest that BADGE and, to a much lesser extent, the diol epoxide of BADGE may constitute a genotoxic hazard, but not the bis-diol or bis-chlorohydrin of BADGE. (+info)Lipid analysis of human HDL and LDL by MALDI-TOF mass spectrometry and (31)P-NMR. (7/52)
The analysis of HDL and LDL is important for the further understanding of atherosclerosis because changes of the protein and lipid moieties occur under pathological conditions. Because destruction of lipids leads to the formation of well-defined products such as lysophospholipids or chlorohydrins, methods that allow their fast and reliable determination would be useful. In this study, matrix-assisted laser desorption and ionization time-of-flight mass spectrometry (MALDI-TOF MS) was applied for the analysis of the lipid composition of human lipoproteins. These data were compared with high resolution (31)P-NMR spectroscopy. Differences between LDL and HDL in sphingomyelin and phosphatidylcholine content could be monitored by NMR and mass spectrometry, and differences with respect to the extraction efficiency were found by MALDI-TOF MS. Additionally, treatment of LDL with hypochlorite and phospholipase A(2) resulted in marked changes (formation of chlorohydrines and lysolipids). Lysophosphatidylcholines were detectable by both methods, whereas MALDI-TOF MS failed to detect chlorohydrines of phospholipids. We conclude that MALDI-TOF MS provides rapidly a reliable lipid profile of lipoproteins. However, a previous lipid separation must be performed to detect lipid oxidation products. NMR can be directly applied, but suffers from lower sensitivity, and provides only limited information on fatty acid composition. (+info)The effects of alpha-chlorohydrin on the composition of rat and rabbit epididymal plasma: a possible explanation of species difference. (8/52)
The relationship between the antifertility effect of alpha-chlorohydrin and changes in composition of luminal plasma from the cauda epididymidis of rats and rabbits has been investigated. At each dose regimen studied, the fertilizing capacity of rats treated with alpha-chlorohydrin was reduced to zero. The levels of sodium, potassium, glycerylphosphorylcholine (GPC), acid phosphatase and alkaline phosphatase in epididymal plasma were not markedly affected by drug treatment. The most noticeable change was a considerable increase in the concentration of lactic dehydrogenase (LDH) at all dose levels and of glutamic-oxaloacetic transaminase (GOT) after 7 days of treatment with 8 and 16 mg/kg. The effect of cold shock on the composition of epididymal plasma showed that LDH and GOT are, at least in part, derived from spermatozoa. In contrast, alpha-chlorohydrin did not have an antifertility action in the rabbit, and the only notable change in the compositon of epididymal plasma was an increase in the level of GPC. These results provide evidence that, in the rat, alpha-chlorohydrin or a metabolite primarily exerts its antifertility effect by a direct action on the spermatozoa, whilst in the rabbit a barrier may exist to the entrance of the drug into the lumen of the epididymal duct. (+info)Chlorohydrins are a class of organic compounds that contain a chloro group (-Cl) attached to a hydroxyl group (-OH). They are commonly used in the production of various chemicals and pharmaceuticals, as well as in the synthesis of polymers and resins. In the medical field, chlorohydrins have been used as intermediates in the synthesis of various drugs and antibiotics. For example, they are used in the production of the antibiotic chloramphenicol, which is used to treat a variety of bacterial infections. Chlorohydrins have also been studied for their potential therapeutic effects in various diseases. For example, some studies have suggested that chlorohydrins may have anti-inflammatory and anti-cancer properties, and may be useful in the treatment of conditions such as rheumatoid arthritis and cancer. However, it is important to note that chlorohydrins can also be toxic and may cause adverse effects when ingested or inhaled. As such, they are typically handled and used with caution in the laboratory and in the production of pharmaceuticals.
Ethylene chlorohydrin is a chemical compound that is not commonly used in the medical field. It is a colorless liquid with a pungent odor and is produced by the reaction of ethylene oxide with hydrochloric acid. Ethylene chlorohydrin is used in the production of various chemicals, including solvents, plasticizers, and flame retardants. It is not used in any medical applications and is not considered to be a medically relevant compound.
Ethylene dichloride (EDC) is a colorless, flammable liquid with a sweet and pungent odor. It is a chlorinated hydrocarbon that is primarily used as a solvent in the production of various chemicals, including vinyl chloride, which is used to make polyvinyl chloride (PVC) plastics. In the medical field, ethylene dichloride is not commonly used as a therapeutic agent or medication. However, it has been associated with various health effects, including liver and kidney damage, respiratory problems, and cancer. Exposure to ethylene dichloride can occur through inhalation, ingestion, or skin contact, and it is considered a hazardous substance by regulatory agencies such as the US Environmental Protection Agency (EPA) and the Occupational Safety and Health Administration (OSHA). In some cases, ethylene dichloride may be used as a preservative in medical devices or as a solvent in the production of certain medical products. However, its use in these applications is typically limited due to its potential health risks.
Hypochlorous acid (HOCl) is a weak acid that is produced by the immune system's white blood cells, specifically neutrophils, as a part of the body's defense mechanism against bacterial and fungal infections. It is a powerful oxidizing agent that can kill or inhibit the growth of microorganisms by breaking down their cell walls and membranes. In the medical field, hypochlorous acid is used as a disinfectant and antiseptic to clean wounds, skin infections, and other contaminated surfaces. It is also used in some medical devices, such as endoscopes and catheters, to prevent the growth of bacteria and other microorganisms. Hypochlorous acid has also been studied for its potential therapeutic applications in various medical conditions, including chronic wounds, inflammatory diseases, and cancer. However, more research is needed to fully understand its effects and potential uses in medicine.
Propylene chlorohydrin
Halohydrin
2-Chloroethanol
1,4-Butane sultone
Hypochlorous acid
Chloropropanol
Chlorobutanol
Chromium(II) acetate
Ethylene oxide
Ethylene glycol dinitrate
3-Hydroxypropionic acid
Ethylene glycol
Wacker process
Epoxide
Propylene oxide
Ralph Landau
3-MCPD
Diethylethanolamine
Dynamic kinetic resolution in asymmetric synthesis
Dehydrohalogenation
Percy Lavon Julian
Sterilization (microbiology)
List of MeSH codes (D02)
2,3-Epoxybutane
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Ethylene chlorohydrin1
- Ethanolamines were prepared in 1860 by Wurtz from ethylene chlorohydrin and aqueous ammonia. (chemicalbook.com)
Chemistry1
- 1,2-Ethylenediamine is often abbreviated 'en' in inorganic chemistry. (atamanchemicals.com)
Ethylene Chlorohydrin8
- Toxicity of ethylene chlorohydrin. (cdc.gov)
- Study of a fatal case of ethylene chlorohydrin poisoning. (cdc.gov)
- Toxic effects of ethylene chlorohydrin. (cdc.gov)
- Experimental data on the substantiation of the threshold of ethylene chlorohydrin in the air of the working zone. (cdc.gov)
- On the toxic properties of ethylene chlorohydrin in the air of working premises. (cdc.gov)
- Genetic Toxicity Evaluation of 2-Chloroethanol (Ethylene Chlorohydrin) in Salmonella/E.coli Mutagenicity Test or Ames Test. (nih.gov)
- Home » Chemical Effects in Biological Systems (CEBS) » Genetic Toxicity Evaluation of 2-Chloroethanol (Ethylene Chlorohydrin) in Salmonella/E.coli Mutagenicity Test or Ames Test. (nih.gov)
- Treatments with ethylene chlorohydrin in sealed containers, at the rate of 0.25 ml. per liter of air space, stimulate shoot growth. (upr.edu)