Allyl alcohol toxicity

Ohno Y, Jones TW, Ormstad K. 1985. Allyl alcohol toxicity in isolated renal epithelial cells Protective effects of low molecular weight thiols. Chem.-Biol Interact 52 289-299. 

Ohno Y, Ormstad, K, Ross D, et al. 1985. Mechanism of allyl alcohol toxicity and protective effects of low-molecular-weight thiols studied with isolated rat hepatocytes. Toxicol Appl Pharmacol 78 169-179. 

Atzori L, Dore M, and Congiu L (1989) Aspects of allyl alcohol toxicity. Drug Metabolism and Drug Interaction 7 295-319. 

PTT has different side reaction products. Instead of the acetaldehyde produced with PET, acrolein and allyl alcohol are the volatile byproducts of PTT production. The generation of acrolein is to be expected since it is one of the starting raw materials for making PDO. Acrolein is toxic and is a very strong lachrymator [22], and requires special handling and treatment. 

Dunlap MK et ah The toxicity of allyl alcohol. Arch Ind Health 18 303-311, 1958... 

Torkelson TR, Wolf MA, Oyen F, Rowe VK Vapor toxicity of allyl alcohol as determined on laboratory animals. Am Ind Hyg Assoc J 20 224-229, 1959... 

British Industrial Biological Research Association BIBRA Toxicity Profile of Allyl Alcohol. Technical Report 229, pp 1-9. Carshalton, UK, 1995... 

Allylic acetates are usually prepared by esterification from allylic alcohols. However, the corresponding alcohols are often only accessible by the fairly expensive hydride reduction of carbonyl compounds. Consequently, direct allylic functionalization of easily available olefins has been intensively investigated. Most of these reactions involve peroxides or a variety of metal salts.However, serious drawbacks of these reactions, (e.g. toxicity of some metals, stoichiometric reaction conditions, or nongenerality) may be responsible for their infrequent use for the construction of allylic alcohols or acetates. 

Patel, J.M., Gordon, W.P, Nelson, S.D. Leibman, K.C. (1983) Comparison of hepatic biotransformation and toxicity of ahyl alcohol and [l,l-2H2]allyl alcohol in rats. DrugMetab. Dispos., 11, 164-166... 

An example of a structural substituent that is often metabolized (bioactivated) to an electrophile is the allyl alcohol substituent (C=C—C—OH). Allyl alcohol moieties are found in many commercial chemical substances, either as the free alcohol or as an ester or ether. As illustrated in Scheme 4.1, allyl alcohols (and also as their esters or ethers) that contain at least one hydrogen atom on the alcoholic carbon can be oxidized in the liver by alcohol dehydrogenase (ALDH) to the corresponding a, 3-unsaturated carbonyl metabolite, which is toxic in many cases [29-31]. The hepatotoxicity of allyl alcohol (1), for example, is due to its oxidation by ALDH to acrolein (2), an a,(3-unsaturated aldehyde, which undergoes Michael addition with cellular nucleophiles in the liver [29] (Scheme 4.1). Cyclic allyl alcohols (Scheme 4.1) are expected to undergo similar enzymatic oxidation to yield a,(3-unsaturatcd carbonyl metabolites and are also likely to be toxic. 

As with allyl alcoholic substituents, propargyl alcoholic substituents that contain at least one hydrogen atom on the alcoholic carbon are also known to undergo enzymatic oxidation to the corresponding a,(3-unsaturated carbonyl metabolites and are fairly toxic [30, 31, 34]. In addition, propargyl alcohols that contain an aromatic... 

The hepatocytes, or parenchymal cells, represent about 80% of the liver by volume and are the major source of metabolic activity. However, this metabolic activity varies depending on the location of the hepatocyte. Thus, zone 1 hepatocytes are more aerobic and therefore are particularly equipped for pathways such as the p-oxidation of fats, and they also have more GSH and GSH peroxidase. These hepatocytes also contain alcohol dehydrogenase and are able to metabolize allyl alcohol to the toxic metabolite acrolein, which causes necrosis in zone 1. Conversely, zone 3 hepatocytes have a higher level of cytochromes P-450 and NADPH cytochrome P-450 reductase, and lipid synthesis is higher in this area. This may explain why zone 3 is most often damaged, and lipid accumulation is a common response (see "Carbon Tetrachloride," for instance, chap. 7). 

Note Nonpolar solvent soluble in alcohols, ethers, chloroform, benzene, and most fixed and volatile oils insoluble in water nonflammable extremely toxic by inhalation, ingestion, or skin absorption carcinogenic incompatible with allyl alcohol, silanes, triethyldialuminum, and many metals (e.g., sodium). Synonyms tetrachloromethane, perchloromethane, methane tetrachloride, Halon-104. 

Triallylphosphate is the phosphate triester of allyl alcohol and contains unsaturated C=C bonds in its structure. This compound is a liquid (fp, -50°C). It is regarded as having a high toxicity and produces abnormal tissue growth when administered subcutaneously. It has been known to explode during distillation. 

Human liver alcohol dehydrogenase (Table 4-1) catalyzes the oxidation of digitoxigenin and derivatives. This is a potentially important detoxification pathway. Liver alcohol dehydrogenase may also toxify chemicals, metabolizing several xylyl alcohols to aldehydes that are toxic to lung and allyl alcohol to the extremely neurotoxic acrolein. 

Toxicity Exposure to vapors of allyl alcohol causes irritation to the eyes, skin, and upper respiratory tract. Laboratory studies with animals have shown symptoms of local muscle spasms, pulmonary edema, tissue damage to liver and kidney, convulsions, and death. In view of this, workers should be instructed to wear protective clothing.2 105 106... 

Table 4 lists a variety of alkoxypropionaldeliydes and certain of their properties (67). Alcohols up to //-butyl have been added to acrolein in this fashion. Methyl, ethyl, and allyl alcohols react with ease, while the addition of hexyl or octyl alcohol proceeds in low yields. Although the alkoxypropionaldeliydes have found only limited industrial utility, it is anticipated that they will find use as replacements for more toxic solvents. Furthermore, the alkoxypropionaldeliydes may readily be reduced to the corresponding alkoxypropanols, which may also have desirable properties as solvents. 

DOT CLASSIFICATION 8 Label Corrosive SAFETY PROFILE Poison by ingestion, inhalation, and intravenous routes. Questionable carcinogen with experimental tumorigenic data. Experimental reproductive effects. A corrosive. A skin and severe eye irritant. An allergen. Has been reported as causing irritation of mucous membranes and heart rhythm disturbances in humans. Violent reaction with water -(above 30°C), acetone + water, methanol, methanol + sodium hydrogen carbonate, 2-ethoxyethanol, dimethyl formamide, 3-butanone + sodium hydroxide + water, allyl alcohol + sodium hydroxide + water (at 28°C). When heated to decomposition it emits toxic fumes of CL and NOx. See also CHLORIDES. 

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