Phenol (CHEM000165)

Record Information
Version1.0
Creation Date2009-03-06 18:58:14 UTC
Update Date2026-05-14 17:48:54 UTC
Accession NumberCHEM000165
Identification
Common NamePhenol
ClassSmall Molecule
Description
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].
Contaminant Sources
  • Clean Air Act Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anti-Infective Agent, Local
  • Antipsoriatic Agent
  • Antiseptic Agent
  • Aromatic Hydrocarbon
  • Disinfectant
  • Drug
  • Food Toxin
  • Household Toxin
  • Human Neurotoxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pollutant
  • Sclerosing Solution
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Acide carboliqueChEBI
Acide pheniqueChEBI
BenzenolChEBI
Carbolic acidChEBI
CarbolsaeureChEBI
HydroxybenzeneChEBI
KarbolsaeureChEBI
OxybenzeneChEBI
Phenic acidChEBI
Phenylic acidChEBI
Phenylic alcoholChEBI
PHOHChEBI
Liquefied phenolKegg
Phenol for disinfectionKegg
Phenol, liquefiedKegg
PaoscleKegg
CarbolateGenerator
PhenateGenerator
PhenylateGenerator
AnbesolHMDB
BenzophenolHMDB
Campho-phenique cold sore gelHMDB
Campho-phenique gelHMDB
Campho-phenique liquidHMDB
Carbolic acid liquidHMDB
Carbolic oilHMDB
Carbolicum acidumHMDB
CarbolsaureHMDB
Cepastat lozengesHMDB
Cuticura pain relieving ointmentHMDB
FenolHMDB
FenoloHMDB
FenosmolinHMDB
FenosmolineHMDB
Hydroxy-benzeneHMDB
IPHHMDB
IZALHMDB
Liquid phenolHMDB
Liquified phenolHMDB
Monohydroxy benzeneHMDB
MonohydroxybenzeneHMDB
MonophenolHMDB
PhenicHMDB
Phenic alcoholHMDB
Phenol alcoholHMDB
Phenol homopolymerHMDB
Phenol liquidHMDB
Phenol moltenHMDB
Phenol polymer-boundHMDB
Phenol solutionHMDB
Phenol syntheticHMDB
Phenolated waterHMDB
Phenolated water for disinfectionHMDB
PhenoleHMDB
PhenosmolinHMDB
Synthetic phenolHMDB
Tea polyphenolHMDB
Phenol, sodium saltHMDB
Phenolate sodiumHMDB
CarbolHMDB
Phenolate, sodiumHMDB
Sodium phenolateHMDB
Chemical FormulaC6H6O
Average Molecular Mass94.111 g/mol
Monoisotopic Mass94.042 g/mol
CAS Registry Number108-95-2
IUPAC Namephenol
Traditional Namephenol
SMILESOC1=CC=CC=C1
InChI IdentifierInChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
InChI KeyISWSIDIOOBJBQZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Adipose Tissue
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Muscle
  • Nerve Cells
  • Platelet
  • Spleen
  • Stratum Corneum
  • Testes
  • Thyroid Gland
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point40.9°C
Boiling Point182°C (359.6°F)
Solubility82.8 mg/mL at 25°C [SOUTHWORTH,GR & KELLER,JL (1986)]
Predicted Properties
PropertyValueSource
Water Solubility46.6 g/LALOGPS
logP1.39ALOGPS
logP1.67ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)10.02ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.04 m³·mol⁻¹ChemAxon
Polarizability9.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureInhalation (27) ; oral (27) ; dermal (27) ; eye contact (27)
Mechanism of ToxicityPhenol 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. (5, 28)
MetabolismWhen 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. (28, 2, 4, 1, 3)
Toxicity ValuesLD50: 400 mg/kg/day (Oral, Rat) (28) LD50: 669 mg/cm2/day (Dermal, Rat) (28) LD50: 1400 mg/cm2/day (Dermal, Rabbit) (28)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (26)
Uses/SourcesPhenol 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. (28)
Minimum Risk LevelAcute Oral: 1 mg/kg/day (Rat) (28)
Health EffectsLong-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. (28)
SymptomsBurning 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. (30, 28)
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB03255
HMDB IDHMDB0000228
FooDB IDFDB000893
Phenol Explorer IDNot Available
KNApSAcK IDC00002664
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhenol
Chemspider IDNot Available
ChEBI ID15882
PubChem Compound ID996
Kegg Compound IDC15584
YMDB IDYMDB16074
ECMDB IDECMDB23832
References
Synthesis Reference

http://en.wikipedia.org/wiki/Phenols#Synthesis_of_phenols

MSDSLink
General References
1. Blanchi, Daniele. New process for direct synthesis of phenol from benzene. Chimica e l'Industria (Milan, Italy) (2005), 87(8), 90-93.
2. Kilic SS, Aydin S, Kilic N, Erman F, Aydin S, Celik I: Serum arylesterase and paraoxonase activity in patients with chronic hepatitis. World J Gastroenterol. 2005 Dec 14;11(46):7351-4.
3. Tanaka T, Kasai K, Kita T, Tanaka N: Distribution of phenol in a fatal poisoning case determined by gas chromatography/mass spectrometry. J Forensic Sci. 1998 Sep;43(5):1086-8.
4. McDonald TA, Holland NT, Skibola C, Duramad P, Smith MT: Hypothesis: phenol and hydroquinone derived mainly from diet and gastrointestinal flora activity are causal factors in leukemia. Leukemia. 2001 Jan;15(1):10-20.
5. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6.
6. Blades KJ, Patel S: The dynamics of tear flow within a phenol red impregnated thread. Ophthalmic Physiol Opt. 1996 Sep;16(5):409-15.
7. Miller WL, Doughty MJ, Narayanan S, Leach NE, Tran A, Gaume AL, Bergmanson JP: A comparison of tear volume (by tear meniscus height and phenol red thread test) and tear fluid osmolality measures in non-lens wearers and in contact lens wearers. Eye Contact Lens. 2004 Jul;30(3):132-7.
8. Hume R, Barker EV, Coughtrie MW: Differential expression and immunohistochemical localisation of the phenol and hydroxysteroid sulphotransferase enzyme families in the developing lung. Histochem Cell Biol. 1996 Feb;105(2):147-52.
9. Slatkin NE, Rhiner M: Phenol saddle blocks for intractable pain at end of life: report of four cases and literature review. Am J Hosp Palliat Care. 2003 Jan-Feb;20(1):62-6.
10. Bauer M, Patzelt D: A method for simultaneous RNA and DNA isolation from dried blood and semen stains. Forensic Sci Int. 2003 Sep 9;136(1-3):76-8.
11. Norberg J, Emneus JA, Jonsson JA, Mathiasson L, Burestedt E, Knutsson M, Marko-Varga G: On-line supported liquid membrane-liquid chromatography with a phenol oxidase-based biosensor as a selective detection unit for the determination of phenols in blood plasma. J Chromatogr B Biomed Sci Appl. 1997 Nov 7;701(1):39-46.
12. Tucker IG: A method to study the kinetics of oral mucosal drug absorption from solutions. J Pharm Pharmacol. 1988 Oct;40(10):679-83.
13. Achterrath-Tuckermann U, Saano V, Minker E, Stroman F, Arny I, Joki S, Nuutinen J, Szelenyi I: Influence of azelastine and some selected drugs on mucociliary clearance. Lung. 1992;170(4):201-9.
14. Tatsumi H, Shimada N, Kuramoto R, Mochizuki Y, Nishizima M, Arai M, Osanai K, Ishihara K, Goso K, Hotta K: [The phenol turbidity test for measurement of pulmonary surfactants in amniotic fluid--rapid test for fetal lung maturity (author's transl)]. Acta Obstet Gynaecol Jpn. 1981 May;33(5):643-50.
15. Jones AL, Hagen M, Coughtrie MW, Roberts RC, Glatt H: Human platelet phenolsulfotransferases: cDNA cloning, stable expression in V79 cells and identification of a novel allelic variant of the phenol-sulfating form. Biochem Biophys Res Commun. 1995 Mar 17;208(2):855-62.
16. Bartholomew LE, Bartholomew FN: Antigenic bacterial polysaccharide in rheumatoid synovial effusions. Arthritis Rheum. 1979 Sep;22(9):969-77.
17. Le Poole IC, Yang F, Brown TL, Cornelius J, Babcock GF, Das PK, Boissy RE: Altered gene expression in melanocytes exposed to 4-tertiary butyl phenol (4-TBP): upregulation of the A2b adenosine receptor 1. J Invest Dermatol. 1999 Nov;113(5):725-31.
18. Bukowska B, Kowalska S: Phenol and catechol induce prehemolytic and hemolytic changes in human erythrocytes. Toxicol Lett. 2004 Aug 30;152(1):73-84.
19. Asai Y, Ohyama Y, Taiji Y, Makimura Y, Tamai R, Hashimoto M, Ogawa T: Treponema medium glycoconjugate inhibits activation of human gingival fibroblasts stimulated with phenol-water extracts of periodontopathic bacteria. J Dent Res. 2005 May;84(5):456-61.
20. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24.
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=12058733
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=16953321
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=17852157
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=19029204
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=20886261
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=21492257
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=21689881
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=21809019
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=21822930