Cresol

Cresol (Cresolum), methylphenol, CH₃.C₆H₄.OH; known in three isomers: ortho-C. [C₆H₄(CH₃) (OH) (1.2)]; meta-C. [C₆H₄ (CH₃) (OH) (1.3)]; para-C. [C₆H₄ (CH₃) (OH) (1.4)]. Found along with phenol in coal tar, brown coal tar (0.5-0.8%) and in many varieties of wood tar. Para-C. is formed in the intestines during putrefaction from the amino acid tyrosine (see) (a product of protein hydrolysis).-Commercial "crude carbolic acid" (Cresolum crudum, Ph. VII) consists mainly of meta-C. (up to 50%) with impurities of para-C., traces of phenol and ortho-cresol, as well as small amounts of higher phenols, naphthalene and hydrocarbons. - Obtained by fractional distillation of tar and fractional precipitation of acids from the alkaline extract of "heavy coal oil" (fraction 188-202°) during the isolation of phenol from it. Properties of C. Simple C. (Cresolum crudum) is a thick light or dark brown liquid with a characteristic burnt odor; incompletely and with difficulty soluble in water, easily soluble in alcohol, ether, hot solutions of caustic alkalis. In a purer form (Tri-kresolum) it is a yellowish transparent liquid, soluble in 50 parts water, easily in alkalis. In relation to litmus it is neutral or weakly acidic. The quantitative content of isomers in various commercial preparations varies greatly. - In its pharmacological properties C. is very close to phenol; however, its bactericidal action is 2-3 times stronger than phenol (Gruber). Meta-C. acts most strongly, para-C. weaker, and finally ortho-C. (Hailer). Mixtures of isomers act the more strongly the more meta-C. they contain. Addition of acids, salts enhances the bactericidal action. Locally on the skin and mucous membranes it acts irritant and cauterizing. When absorbed, it affects the central nervous system, first exciting and then depressing the respiratory and vasomotor centers. Toxic doses cause increased reflexes, uncoordinated movements, muscle twitching and finally clonic seizures, which intensify upon irritation. In the kidneys and liver, parenchymal degeneration is observed. Absorbed by the skin. Excreted from the body with urine, partly in the form of conjugates with sulfuric and glucuronic acids, partly in oxidized form, and in traces through the lungs. Less toxic than phenol (Schutz). In humans, cresol poisoning causes salivation, vomiting, pupil dilation, severe drop in body temperature and collapse, sometimes laryngeal edema occurs. Seizures are observed more often than in phenol poisoning. Urine is colored dark, contains protein and cylinders. Treatment-see Carbolic acid. For laryngeal educe-ice compresses on the neck. C. is used as a disinfectant instead of carbolic acid. Purified C. in 0.5-1% solution (in surgery, obstetric-gynecological practice, in veterinary medicine)-for disinfection of hands, instruments, in the treatment of wounds, for washing cavities and as an antiparasitic agent; rarely- internally for gastrointestinal diseases. Preparations: Aqua cresolica - cresol water: 1 part cresol solution, soap with 9 parts water. Used externally for dressings, disinfection.- Creolinum (Creolinum anglicum)-a solution of resinous (rosin) soap in a mixture with phenols of heavy coal oil. Contains 12-33% C. (Ph. VII-not less than 30%). Dark brown, oily liquid with unpleasant sharp odor. With water gives a light gray permanent emulsion. For general disinfection-in 5-10% solution; in 0.5-1% solution-for washing body cavities and in surgical practice, in veterinary medicine, as well as for scabies.- Creolinum purissimum. Internally (rarely)-in capsules (0.06-0.3) three times a day. Externally-in 1/2-2% solution. Similar preparations: Creolinum viennense abasicum, Cyllin, Sal Creolin, Kremulsion, Desinfectol, Izal, Sapokresolin, Russian preparation-Naphthalysol.- Cresin-equi-molecular compound of ortho-C. and cineole. Antisepticum.- Cresolalbin (Creolalbin)-creolin protein; powder; astringent for the intestine.- Cresolform-oxymethylene cresol tannin; brownish-white powder. Soluble in alkalis, insoluble in gastric juice. Antiseptic, astringent; used internally and externally.- Europhenum-iso-butyl-iodo-ortho-C. Amorphous yellow powder, insoluble in water, soluble in alcohol, ether, chloroform and fatty oils. Contains about 28% iodine. In an alkaline medium it slowly releases iodine. Externally-instead of iodoform. Internally-0.05 several times a day in pills for tbc, bronchitis, intestinal diseases.- Kresamin (Tricresolamin)-aqueous solution of tricresol (about 25%) with ethylenediamine. Strong antiseptic. In 2-20% solutions, ointments. For inhalation-in pulmonary tbc.- Kresival-cresol sulfuric acid calcium (6%), dissolved in aromatic syrup. Expectorant for acute and chronic diseases of the respiratory organs. For adults-3-4 times a day tablespoon, for children-teaspoon (similar preparation Pneumocol).- Cresol-soap-cresol solution with formaldehyde admixture. For disinfection.- Lophanum-tri-iodomethylcresol. Instead of iodoform in dermatology. No longer in sale.- Lysoolum (factory name Liquor Cresoli saponatus, Ph. VII)-soap-cresol solution (with potassium soap). Transparent red-brown oily liquid. Contains 50% cresol. Mixes in all proportions with water, glycerin, alcohol, gasoline without forming turbidity. The German pharmacopoeia preparation contains 25% C. for disinfection of hands and operative field-in 1% solution; for instruments-4%; for disinfection of urine, secretions-10%.- Sarrol contains 40% C. in a mixture with hydrocarbons (from petroleum). Brown liquid. Does not mix with water and floats on it. Used for disinfection of waste and secretions, for destruction of mosquito larvae etc.- Solveolum- aqueous solution of cresol with cresotinic acid sodium [(CH₃) (OH)C₆H₃.COONa]. For disinfection-in 1-2% solution. Internally-0.03-0.2 for tbc for intestinal disinfection-in solutions, capsules, drops.- Tricresol-formalin-a mixture of C. with formalin. In dental practice.- Traumatum-iodo-cresol. Violet powder without odor (54% iodine). Replacement of iodoform in powders, ointments and pastes (5-10%). g. Shkavera. Poisoning by C. Besides professional poisoning by C. in forensic medical practice, accidental and intentional poisoning by preparations of C. also occurred; of these, the first place belongs to the fairly widespread in obstetrics and gynecology lysool (soap-cresol solution), which was mistakenly taken internally instead of another medicine, or poisoning occurred due to the use of lysool from the genital side (douching). Cases of intentional introduction of lysool per os or per vaginam for the purpose of expulsion of the fetus have been described. Lysool is also used for suicide, for the purpose of killing children, and sometimes adults. Some cases of poisoning ended in death. Dosis letalis in poisoning by preparations of C. is difficult to determine. Clinical phenomena, path-anatomical changes do not essentially differ from those in phenol poisoning (see Carbolic acid). Not only local cauterizing action is found, but also general, mainly on the central nervous system. However, it should be noted that in poisoning by preparations of C., their action may somewhat vary depending on the content of other constituent parts. There are indications that 10-20% solutions of lysool already possess a noticeable cauterizing action on mucous and serous membranes; with prolonged external use of it, persistent dermatitis may develop (Kampfer), and with general poisoning by lysool, loss of consciousness almost always quickly occurs. At autopsy, burns of the mucous membranes of the lips and adjacent skin were found in the form of dense yellowish-brown areas. On the mucous membrane of the mouth, pharynx, upper part of the esophagus-light gray or brownish burns (scabs). In the lower part of the esophagus, in the stomach, changes are expressed more weakly and resemble the picture of poisoning with caustic alkali: the mucous membrane appears swollen, red-brown with gray crusts on the tops of the folds and slippery, as if soaped, which obviously depends on the action of potassium soap-a component of lysool. If lysool penetrates into the respiratory tract, foci of pneumonia may form. The smell of lysool is felt from the internal organs. As for other preparations of C., it is known that solveolum, according to Gruber, has no local cauterizing action, while solutol cauterizes only in undiluted form. In case of suspicion of poisoning by C., parts of the corpse must be sent for chemical examination.

Vladimirsky. Discovery in judicial cases and in professional poisonings. In discoveries, one has to deal with a mixture of three isomers of ortho-, meta-, and para-cresol, which constitutes commercial Cresol and the main component of crude carbolic acid. Cresol, like carbolic acid, distills over with steam from an acidified solution, although they are almost insoluble in water, forming droplets or turbidity in the distillate. The distillate is made alkaline with soda and extracted with ether. The residue after evaporation of the ether (at room temperature) has a more suffocating odor than carbolic acid and does not dissolve in water. The mixture of Cresols gives a blue-violet coloration with ferric chloride. Ortho-Cresol gives a blue coloration turning green, meta-Cresol gives an unstable blue coloration turning with turbidity into greenish-brown. With bromine, Cresols give tribromcresols, which allows for their bromometric quantitative determination (see Carbolic acid). Discovery in urine is analogous to the discovery of carbolic acid. - For the quantitative determination of Cresol in lysol, a sample of lysol is dissolved in caustic soda and the soap is precipitated by adding a saturated solution of NaCl. The precipitate is filtered, washed with a saturated salt solution. The filtrate is acidified and Cresol is determined in it by bromometry (see Carbolic acid). - For the discovery of Cresol vapors in air, the latter is drawn through bottles with a solution of caustic soda by means of an aspirator (see Poisons, isolation). The liquid is combined, acidified, again made alkaline with sodium carbonate, and Cresol is extracted with ether. In the residue after evaporation of the ether, Cresol is determined by bromometry (see Carbolic acid).