T3D0182

183 T3D0182

Phenol

Phenol, is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe; in laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. Notwithstanding the effects of concentrated solutions, it is also used in cosmetic surgery as an exfoliant, to remove layers of dead skin (Wikipedia). In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2]. 108-95-2

996

C6H6O

94.041870 White powder.

40.9°C

182°C (359.6°F)

82.8 mg/mL at 25°C [SOUTHWORTH,GR & KELLER,JL (1986)]

Inhalation (L159) ; oral (L159) ; dermal (L159) ; eye contact (L159)

Phenol is irritating and corrosive at high concentrations. Phenol impairs the stratum corneum and produces coagulation necrosis by denaturing and precipitating proteins. It is suggested that dermal application of phenol increases the formation of free radicals in the skin, and that the redox cycling of these radicals reduces antioxidant capacity, leading to significant oxidative damage of protein, DNA, and lipids. Phenol also act as a cyclooxygenase inhibitor. (A227, L624)

When it is absorbed through the lungs, gut, or skin, phenol conjugated at the portal-of-entry and free phenol enter the bloodstream where it can then be distributed throughout the body. The dilution of phenol in water enhances the dermal absorption of phenol. Three different enzymes systems catalyze the reactions that transform phenol. Cytosolic phenol sulfotransferases catalyze the transfer of inorganic sulfur from the activated 3'-phosphoadenosine-5'phosphosulfate donor molecule to the hydroxyl group on phenol. Microsomal membrane-located uridine diphosphate (UDP) glucuronosyltransferases catalyze the transfer of an activated glucuronic acid molecule to the hydroxyl moiety of phenol to form an O-glucuronide conjugate. Cytochrome P4502E1, also microsomally located, catalyzes the hydroxylation of phenol to form hydroquinone (and to a much lesser extent, catechol), which is then acted upon by the phase II enzymes. Hydroquinone can, in turn, form conjugates, undergo peroxidation to form benzoquinone, or undergo further oxidation to form trihydroxybenzene. All three enzyme systems that metabolize phenol are found in multiple tissues and there is competition among them not only for phenol, but also for subsequent oxidative products, like hydroquinone. As a consequence, the relative amount of the products formed can vary based on species, dose and route of administration. Cytochromes other than CYP2E1, such as CYP2F2 are suggested to participate in the phenol metabolism in the liver. Tyrosinase also catalyzes the oxidation of phenols. The gastrointestinal tract, liver, lung, and kidney appear to be the major sites of phenol sulfate and glucuronide conjugation of simple phenols. Phenol, in its free and conjugated forms, is a normal constituent of human urine. (L624, A223, A225, A221, A224) LD50: 400 mg/kg/day (Oral, Rat) (L624) LD50: 669 mg/cm2/day (Dermal, Rat) (L624) LD50: 1400 mg/cm2/day (Dermal, Rabbit) (L624) 3, not classifiable as to its carcinogenicity to humans. (L135)

Phenol is used to make plastics. Phenol is also used as a disinfectant in household cleaning products and in consumer products such as mouthwashes, gargles, throat sprays. Exposure may result from breathing air containing phenol and drinking contaminated water or eating food contaminated with phenol. Exposure also occurs through dermal contact with contaminated air or by skin contact with products containing phenol. Dermal contact can occur through the use of general disinfectants and ointments containing phenol. Ingestion can occur through the use of products such as throat lozenges or sore throat sprays that contain phenol. (L624)

Acute Oral: 1 mg/kg/day (Rat) (L624)

Long-term exposure to phenol at work has been associated with cardiovascular disease, irritation of the respiratory tract and muscle twitching depedning of the route of exposure. Ingestion of liquid products containing concentrated phenol can cause serious gastrointestinal damage and even death. Application of concentrated phenol to the skin can cause severe skin damage. Longer-term exposure to high levels of phenol caused damaged to the heart, kidneys, liver, and lungs. Liver effects, as judged by increased serum activities of alanine aminotransferase (ALT) and aspartate amino transferase (AST), were also reported in a case of prolonged inhalation exposure to phenol. (L624)

Burning pain in mouth and throat; white necrotic lesions in mouth; abdominal pain, vomiting, bloody diarrhea, pallor, sweating, weakness, headache, dizziness, tinnitus can result from phenol poisoning. Phenol absorption can lead to weak irregular pulse, hypotension, shallow respirations, cyanosis, pallor, a profound fall in body temperature, muscle tremors, and difficulty walking. Possibly fleeting excitement and confusion, followed by unconsciousness. (T48, L624)

2009-03-06T18:58:14Z

2026-05-14T17:48:54Z

Sulfotransferase 1A1 (P50225) Sulfotransferase 1A3/1A4 (P50224) Sulfotransferase family cytosolic 1B member 1 (O43704) Tyrosinase (P14679) UDP-glucuronosyltransferase 1-6 (19224) (A223, A225, A221, A224)

http://en.wikipedia.org/wiki/Phenol

C00146

147450 147460 171150 191740 600641 601292

15882

24-DICHLOROPHENOL

D019800

Phenol

DB03255

IPH

1148

true

OC1=CC=CC=C1

C6H6O

InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H

ISWSIDIOOBJBQZ-UHFFFAOYSA-N

94.1112

94.041864814

Exogenous Solid 1.46

HMDB00228

971

<p>http://en.wikipedia.org/wiki/Phenols#Synthesis_of_phenols</p>

CHEM000165

DTXSID5021124

NS00010045

phenol

20.23

28.038899999999998

9.812560861971921

10.016150276173818

-5.476712177992348

1.39

-0.31

4.66e+01 g/l