From Big Medical Encyclopedia

PHENOLS — the organic compounds of an aromatic series containing one or several hydroxylic groups connected with carbon atom of an aromatic kernel in a molecule. T. and products of their transformations are natural endogenous antioxidants (see. And ntiokislitel) in vegetable and zooblasts. These connections have bactericidal properties, in medicine are used for disinfection (see Desinfectants) and as pharmaceuticals with antiseptic action (see. Antiseptic agents). In the medical and food industry F. use as preservatives. Many synthetic derivatives F. (ethers, haloid derivatives, etc.) apply to the most various purposes, e.g. a xeroform — as an antiseptic agent, diphenyl ether — as the heat carrier, nitroderivatives (picric to - that, etc.) are explosive substances. T. serve as a feed stock for industrial synthesis of many pharmaceuticals, plastic, dyes. Polyatomic F. apply as antioxidants in the pharmaceutical, food and perfumery industry, show -

tel in the photos as stabilizing, preserving additives in chemical and Neftekhim. industries. Nek-rye F. are toxic: on

the productions connected with their receiving or use they can represent professional harm.

On a number of hydroxyl groups, attached to benzene ring (see Benzene), T. divide into one - two - and triatomic. First representative of a row F., on Krom all group of these connections is called, phenol, hydroxybenzene, or carbolic acid is (see); diatomic F. — pyrocatechin, or

au dihydroxy-benzene, hydrochinone (see), or/g dihydroxy-benzene, resorcin (see), or л£ - dihydroxy-benzene; triatomic f. — pyrogallol (see), or 1,2,3 trihydroxybenzene, oxyhydrochinone, or 1,2,4 trihydroxybenzene, phloroglucinol, or 1,3,5 trihydroxybenzene. Cresols (see) — oxyderivatives of toluene (see), xylenols — oxyderivatives of xylols belong to phenols (see).

In the nature F. seldom meet in a free look. In plants they contain in a type of various derivatives, napr, eugenol — in clove-stems oil, safrol — in sassafroso-vy oil. Especially there are a lot of derivatives F. in fruits of a citrus. In small amounts F. are present at all fruits and fruit. With food of people receives in days apprx. 50 mg of phenols.

T. in the majority are colourless crystal substances, one-atomic F. possess a characteristic intensive smell, are easily driven away with water vapor. Many F. well rastvorima in water and benzene, all F. are well dissolved in alcohol. T. have

acid properties, react with alkalis, forming salts (phenolates). Allocation F is based on this property. by method of extraction of coal tar solutions of alkalis or ammonium hydroxide. T. show also chemical properties of oxycompounds (form simple and esters), and also properties of connections of an aromatic series. T. easily are oxidized. Their oxidability increases in process of increase in a number of hydroxyl groups in an aromaticheeky kernel. Oxidation reaction F. is of very great importance in chemistry and biochemistry of these connections. In the industry F. receive extraction of coal tar, nek-ry simple F. (carbolic to - that, resorcin, hydrochinone) receive synthetic.

In a human body F. are completely oxidized or inactivated some other way (e.g., by methylation). It is not excluded that F., arriving with food, are used for biosynthesis of polyphenols: catecholamines (see), iidolilamin, ubikhinon (see Coenzymes).

Phenols as professional harm. Phenols can come to an organism of the people working in contact with them through lungs, the unimpaired skin and mucous membranes. From a human body F. are allocated with urine (a small part — with expired air), hl. obr. in the form of conjugates with sulfuric and glucuronic to-tami. Monohydric phenols, including cresols, xylenols, etc., are the nervous poisons operating on c. N of page, they also render strong cauterizing and irritant action on skin.

Hectare logenoproizvodny one-atomic F., in particular di - and trichlorophenols, and also the hexachlorhair dryer (2-2 '-dioksi-3,5,6,3', 5', 6 '-geksakhlordife-nilmetan) can in a process of manufacture and at decomposition reaction to form exclusively toxic dioxine, from to-rykh 2,3,7,8-tetrakhlordiben-zo-ya-dioxine, or THDD is most known. Dioxine even in very trace amounts shows dermatotoksichesky, hepatotoxic and neurotoxic properties with the remote impact on a genotype.

Polyatomic F. show properties of blood poisons, causing formation of a methemoglobin (see the Methemoglobinemia), hemolysis (see) with development of hemolitic jaundice (see). From polyatomic F. pyrocatechin is very toxic (the most toxic of dioksiben-zo fishing). Resorcin (-dihydroxy-benzene) is less toxic, than other dihydroxy-benzenes, despite the expressed resorptive action. The pyrogallol used in pharmaceutical industry as an initial product for synthesis of nek-ry helminthicides (see) causes formation of a methemoglobin, is very toxic.

At court. - a medical research of corpses of the people who died of poisoning F., note the changes similar to the changes described at poisoning carbolic to - that.

A picture of chronic and acute poisoning, first aid, emergency treatment, treatment, prevention of poisonings with phenols — cm. Carbolic acid.

Drugs of phenols. To the drugs F used in medical practice. carry carbolic to - that, Tricresolum and other cresols, lysol (see), resorcin (see), and also salol (see), at metabolism to-rogo in an organism phenol is formed. Besides, F. are an effective agent of nek-ry natural products, napr, Russia oil (see Tars), used as pharmaceuticals.

Drugs F. perniciously influence practically all species of microorganisms (bacteria, protozoa, viruses, etc.) that is caused, most likely, by ability of these drugs to cause a denaturation of proteins. During the drawing on skin in the corresponding concentration: drugs F. have local irritative and even the cauterizing effect. Separate drugs F. (resorcin, Russia oil) at; topical administration cause ke-ratoplastichesky and keratolytic effects (see. Keratolytic, keratoplastichesky means).

In medical practice drugs F. use hl. obr. as antiseptic and desinfectants. Nek-ry drugs (e.g., phenol, Tricresolum) apply to preservation of vaccines, serums and injection dosage forms. As antiseptic agents in stomatol. to practice apply hl. obr. resorcin and Tricresolum. Drugs F. with keratolytic and keratoplasti-chesky properties (resorcin, Russia oil) use locally at treatment of a number of skin diseases (seborrhea, eczema, etc.). Salol is applied inside, (usually in combination with other drugs) at diseases of intestines (colitis, coloenterites) and uric ways (pyelites, pyelonephritises, cystitis).

Side effect of drugs F. at topical administration it is shown generally by signs of local irritation of fabrics.

Drugs F., differing

high lipophilicity (phenol, Tricresolum), are easily soaked up through skin and mucous membranes (especially at their damage), in svya-

zi with what such drugs even at topical administration can have adverse resorptive effect on an organism and cause the toxic phenomena (dizziness, a headache, the general weakness, disturbances of breath, decrease in the ABP, etc.).

On degree of toxicity for the person drugs F. differ from each other. The most high toxicity at intake phenol has (carbolic to - that), salol is least toxic.

Ggri intake drugs F. (except salol) can cause acute poisonings (see Poisonings, the table).

Bibliography: B and r and about y V. A. Biolo

gichesky action of vegetable phenolic connections, Kiev, 1976; Biochemistry of phenolic connections, under the editorship of J. Har-born, the lane with English, M., 1968; Glazov O. I. Poisonings and first aid at them, page 55, M., 1944; 3 and p r about m e-

t about in M. N. Fundamentals of biochemistry of phenolic connections, M., 1974; L at d e in and R.'s t and L of wasps To. Acute poisonings, the lane with it., page 370, M., 1983;

Kid va V. V., etc. The Fiziologo-gigiyenichesky characteristic of working conditions and the state of health of workers in production of phenols by method of devolatilization of coal of coals, the Gigabyte. work and the prof. having got sick., No. 1, page 18, 1967; M and sh to about in with to and y M. D. Pharmaceuticals, p. 2, page 404, M., 1984; Acute management at acute poisonings, under the editorship of S. N. Golikov, page 174, M., 1977; Occupational diseases, under the editorship of A. A. Letavet, page 306, M., 1973; Stepanov A. B. Judicial chemistry (himikotoksikologichesky analysis) and definition of professional poisons, page 112, 220, M., 1951; Sh in and y to about in and M. D. Toxicological chemistry, page 111, M., 1975.

3. A. Volkova (gigabyte.), V. K. Muratov (pharm.), N. V. Prokazova (biochemical).