clear
T3DB
Banner
Please note that T3DB is currently undergoing changes to improve data quality and website features. You can access the original version of T3DB here.

T3D0182 - Phenol

Record Information
Version 1.0
Creation Date 2009-03-06 18:58:14 UTC
Update Date 2013-04-25 08:33:11 UTC
Accession Number T3D0182
Identification
Common Name Phenol
Description Phenol is a colorless-to-white solid when pure. It has a distinct odor that is sickeningly sweet and tarry. Commercial phenol is a liquid that evaporates more slowly than water. Phenol is both a manufactured chemical and produced naturally. Large amounts of phenol are produced in the United States. 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. (R983)
Compound Type
  • Organic Compound
  • Aromatic Hydrocarbon
  • Antiseptic
Chemical Structure
Thumb
MOL SDF SMILES InChI
Synonyms
  1. Acide carbolique(french)
  2. Acide phenique
  3. Anbesol
  4. Benzenol
  5. Benzophenol
  6. Carbolicum Acidum
  7. Carbolsaeure
  8. Carbolsaure
  9. Carbolsaure [german]
  10. Cepastat lozenges
  11. Fenol(dutch, polish)
  12. Fenolo(italian)
  13. Fenosmolin
  14. Fenosmoline
  15. Hydroxybenzene
  16. Karbolsaeure
  17. Liquefied phenol (TN)
  18. Liquid phenol
  19. Liquified phenol
  20. M-cresol
  21. Monohydroxy benzene
  22. Monohydroxybenzene
  23. Monophenol
  24. Oxybenzene
  25. Paoscle (TN)
  26. Phenic Acid
  27. Phenic alcohol
  28. Phenol (JP15/USP)
  29. Phenol (liquid)
  30. Phenol (TN)
  31. Phenol alcohol
  32. Phenol for disinfection
  33. Phenol for disinfection (JP15)
  34. Phenol for disinfection (TN)
  35. Phenol homopolymer
  36. Phenol liquid
  37. Phenol molten
  38. Phenol polymer-bound
  39. Phenol reage NT
  40. Phenol synthetic
  41. Phenol [jan]
  42. Phenol, chlorinated
  43. Phenol, chloro derivs.
  44. Phenol, liquefied (usp)
  45. Phenol, polymer-bound
  46. Phenol, sulfurated
  47. Phenol, synthetic
  48. Phenolated water
  49. Phenole
  50. Phenole [german]
  51. Phenole(german)
  52. Phenosmolin
  53. Phenyl alcohol
  54. Phenyl hydrate
  55. Phenyl hydroxide
  56. Phenylalcohol
  57. Phenylic Acid
  58. Phenylic Acid, phenyl hydroxide
  59. Phenylic alcohol
Chemical Formula C6H6O
Average Molecular Weight 94.1112
Monoisotopic Molecular Weight 94.041864814
Chemical IUPAC Name
phenol
CAS Registry Number 108-95-2
SMILES
OC1=CC=CC=C1
InChI Identifier
InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
InChI Key InChIKey=ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class Phenols and Derivatives
Direct Parent Phenols and Derivatives
Alternative Parents Not Available
Molecular Framework Aromatic Homomonocyclic Compounds
Substituents Not Available
External Descriptors
  • phenols(ChEBI)
  • a phenol(Cyc)
DrugBank ID Not Available
PubChem Compound ID 996 Link_out
KEGG ID C00146 Link_out
UniProt ID Not Available
OMIM ID 147450 147460 171150 191740 600641 601292 Link_out
ChEBI ID 15882 Link_out
BioCyc ID 24-DICHLOROPHENOL Link_out
CTD ID D019800 Link_out
Stitch ID Phenol Link_out
PDB ID Not Available
ACToR ID 1148
Wikipedia Link http://en.wikipedia.org/wiki/Phenol Link_out
Physical Properties
Appearance Not Available
Melting Point 40.9 C
Solubility 82.8 mg/mL at 25 °C [SOUTHWORTH,GR & KELLER,JL (1986)]
Predicted LogP 1.6696804943333332
Toxicity Profile
Route of Exposure Inhalation (R307) ; oral (R307) ; dermal (R307) ; eye contact (R307)
Mechanism of Action 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. (R998, R983)
Metabolism 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. (R983, R986, R993, R984, R992)
Toxicity Values LD50: 400 mg/kg/day (Oral, Rat) (R983) LD50: 669 mg/cm2/day (Dermal, Rat) (R983) LD50: 1400 mg/cm2/day (Dermal, Rabbit) (R983)
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources 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. (R983)
Minimum Risk Level Acute Oral: 1 mg/kg/day (Rat) (R983)
Health Effects 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. (R983)
Symptoms 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. (R521, R983)
Treatment Not Available
References
General References
  • R983 — ATSDR - Agency for Toxic Substances and Disease Registry (2008). Toxicological profile for phenol. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  • R998 — Oliveira HM, Sallam HS, Espana-Tenorio J, Chinkes D, Chung DH, Chen JD, Herndon DN: Gastric and small bowel ileus after severe burn in rats: The effect of cyclooxygenase-2 inhibitors. Burns. 2009 May 21. [19464805 Link_out]
  • R986 — Tyapochkin E, Cook PF, Chen G: Isotope exchange at equilibrium indicates a steady state ordered kinetic mechanism for human sulfotransferase. Biochemistry. 2008 Nov 11;47(45):11894-9. Epub 2008 Oct 18. [18928301 Link_out]
  • R993 — Meinl W, Ebert B, Glatt H, Lampen A: Sulfotransferase forms expressed in human intestinal Caco-2 and TC7 cells at varying stages of differentiation and role in benzo[a]pyrene metabolism. Drug Metab Dispos. 2008 Feb;36(2):276-83. Epub 2007 Oct 29. [17967930 Link_out]
  • R984 — Land EJ, Ramsden CA, Riley PA: The mechanism of suicide-inactivation of tyrosinase: a substrate structure investigation. Tohoku J Exp Med. 2007 Aug;212(4):341-8. [17660699 Link_out]
  • R992 — Li D, Fournel-Gigleux S, Barre L, Mulliert G, Netter P, Magdalou J, Ouzzine M: Identification of aspartic acid and histidine residues mediating the reaction mechanism and the substrate specificity of the human UDP-glucuronosyltransferases 1A. J Biol Chem. 2007 Dec 14;282(50):36514-24. Epub 2007 Oct 23. [17956868 Link_out]
  • R307 — ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for chlorophenols. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  • R521 — Gosselin RE, Smith RP, and Hodge HC (1984). Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins.
  • R383 — Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.

Targets

1. Carbonic anhydrase 2

Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.

Phenol acts as an effective, low micromolar inhibitor of isozyme hCAII. (R985)
UniProt ID: P00918 Link_out
Gene: CA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

2. Carbonic anhydrase 1

Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.

Phenol acts as an effective, low micromolar inhibitor of isozyme hCAI. (R985)
UniProt ID: P00915 Link_out
Gene: CA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

3. Carbonic anhydrase 3

Reversible hydration of carbon dioxide.

Phenol acts as an effective, low micromolar inhibitor of isozyme hCAIII. (R985)
UniProt ID: P07451 Link_out
Gene: CA3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

4. Carbonic anhydrase 4

Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.

Phenol acts as an effective, low micromolar inhibitor of isozyme hCAIV. (R985)
UniProt ID: P22748 Link_out
Gene: CA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

5. Carbonic anhydrase 9

Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.

Phenol acts as an effective, low micromolar inhibitor of isozyme hCAIX. (R985)
UniProt ID: Q16790 Link_out
Gene: CA9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

6. Carbonic anhydrase 12

Reversible hydration of carbon dioxide.

Phenol acts as an effective, low micromolar inhibitor of isozyme hCAXII. (R985)
UniProt ID: O43570 Link_out
Gene: CA12 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

7. Carbonic anhydrase 14

Reversible hydration of carbon dioxide.

Phenol acts as an effective, low micromolar inhibitor of isozyme hCAXIV. (R985)
UniProt ID: Q9ULX7 Link_out
Gene: CA14 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

8. Carbonic anhydrase 13

Reversible hydration of carbon dioxide.

Phenol acts as an effective, low inhibitor(in the millimolar range) of isozyme hCAXIV. (R985)
UniProt ID: Q8N1Q1 Link_out
Gene: CA13 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

9. Carbonic anhydrase 5A, mitochondrial

Reversible hydration of carbon dioxide. Low activity.

Phenol acts as an effective, low inhibitor(in the millimolar range) of isozyme hCAVA. (R985)
UniProt ID: P35218 Link_out
Gene: CA5A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

10. Carbonic anhydrase 5B, mitochondrial

Reversible hydration of carbon dioxide.

Phenol acts as an effective, low inhibitor(in the millimolar range) of isozyme hCAVB. (R985)
UniProt ID: Q9Y2D0 Link_out
Gene: CA5B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

11. Carbonic anhydrase 6

Reversible hydration of carbon dioxide. Its role in saliva is unknown.

Phenol acts as an effective, low inhibitor(in the millimolar range) of isozyme hCAVI. (R985)
UniProt ID: P23280 Link_out
Gene: CA6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]

12. Carbonic anhydrase 7

Reversible hydration of carbon dioxide.

Phenol acts as an effective, low inhibitor(in the millimolar range) of isozyme hCAVII. (R985)
UniProt ID: P43166 Link_out
Gene: CA7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R985 — Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. Epub 2008 Jan 26. [18242985 Link_out]