Human Metabolome Database Version 3.5

Showing metabocard for Phenol (HMDB00228)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:07 -0700
HMDB ID HMDB00228
Secondary Accession Numbers None
Metabolite Identification
Common Name Phenol
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].
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Acide carbolique
  2. Anbesol
  3. Benzenol
  4. Benzophenol
  5. Campho-phenique cold sore gel
  6. Campho-phenique gel
  7. Campho-phenique liquid
  8. Carbolic acid
  9. Carbolic acid liquid
  10. Carbolic oil
  11. Carbolicum acidum
  12. Carbolsaure
  13. Cepastat lozenges
  14. Cuticura pain relieving ointment
  15. Fenol
  16. Fenolo
  17. Fenosmolin
  18. Fenosmoline
  19. Hydroxy-benzene
  20. Hydroxybenzene
  21. IPH
  22. IZAL
  23. Liquefied phenol
  24. Liquid phenol
  25. Liquified phenol
  26. Monohydroxy benzene
  27. Monohydroxybenzene
  28. Monophenol
  29. Oxybenzene
  30. Paoscle
  31. Phenic
  32. Phenic acid
  33. Phenic alcohol
  34. Phenol
  35. Phenol alcohol
  36. Phenol homopolymer
  37. Phenol liquid
  38. Phenol molten
  39. Phenol polymer-bound
  40. Phenol solution
  41. Phenol synthetic
  42. Phenolated water
  43. Phenolated water for disinfection
  44. Phenole
  45. Phenosmolin
  46. Phenylic acid
  47. Phenylic alcohol
  48. PHOH
  49. Synthetic phenol
  50. Tea polyphenol
Chemical Formula C6H6O
Average Molecular Weight 94.1112
Monoisotopic Molecular Weight 94.041864814
IUPAC Name phenol
Traditional 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 ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • a phenol(Cyc)
  • phenols(ChEBI)
Substituents
  • N/A
Direct Parent Phenols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Toxin/Pollutant
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 40.9 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 82.8 mg/mL at 25 °C Not Available
LogP 1.46 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 46.6 g/L ALOGPS
LogP 1.39 ALOGPS
LogP 1.67 ChemAxon
LogS -0.31 ALOGPS
pKa (strongest acidic) 10.02 ChemAxon
pKa (strongest basic) -5.5 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 28.04 ChemAxon
Polarizability 9.81 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-7M)
MS/MS Spectrum EI-B (JEOL JMS-01-SG-2)
MS/MS Spectrum EI-B (HITACHI RMU-6L)
MS/MS Spectrum EI-B (JEOL JMS-D-3000)
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Testes
  • Liver
  • Epidermis
  • Thyroid Gland
  • Brain
  • Adipose Tissue
  • Nerve Cells
  • Platelet
  • Spleen
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.86 +/- 0.63 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
13.5 (13.5-13.5) umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
4.8 (0.6-12.8) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
0.065 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
7.0 (5.6-9.2) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
2.7 (0.4-53.0) umol/mmol creatinine Children (1-13 year old) Both Comment Normal
Urine Detected and Quantified
2.2 (1.0-6.7) umol/mmol creatinine Children (1-13 year old) Both Comment Normal
Urine Detected and Quantified
2.2 (0.7-8.5) umol/mmol creatinine Adolescent (13-18 years old) Both Comment Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Breast cancer
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID 657 Link_out
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB000893
KNApSAcK ID C00002664 Link_out
Chemspider ID 971 Link_out
KEGG Compound ID C00146 Link_out
BioCyc ID 24-DICHLOROPHENOL Link_out
BiGG ID Not Available
Wikipedia Link Phenol Link_out
NuGOwiki Link HMDB00228 Link_out
Metagene Link HMDB00228 Link_out
METLIN ID 128 Link_out
PubChem Compound 996 Link_out
PDB ID IPH Link_out
ChEBI ID 15882 Link_out
References
Synthesis Reference Blanchi, Daniele. New process for direct synthesis of phenol from benzene. Chimica e l'Industria (Milan, Italy) (2005), 87(8), 90-93.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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. Pubmed: 16437641 Link_out
  2. 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. Pubmed: 9729832 Link_out
  3. 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. Pubmed: 11243376 Link_out
  4. 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. Pubmed: 8087979 Link_out
  5. Blades KJ, Patel S: The dynamics of tear flow within a phenol red impregnated thread. Ophthalmic Physiol Opt. 1996 Sep;16(5):409-15. Pubmed: 8944185 Link_out
  6. 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. Pubmed: 15499232 Link_out
  7. 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. Pubmed: 8852436 Link_out
  8. 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. Pubmed: 12568439 Link_out
  9. 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. Pubmed: 12969623 Link_out
  10. 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. Pubmed: 9389336 Link_out
  11. Tucker IG: A method to study the kinetics of oral mucosal drug absorption from solutions. J Pharm Pharmacol. 1988 Oct;40(10):679-83. Pubmed: 2907532 Link_out
  12. 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. Pubmed: 1522740 Link_out
  13. 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. Pubmed: 6894513 Link_out
  14. 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. Pubmed: 7695643 Link_out
  15. Bartholomew LE, Bartholomew FN: Antigenic bacterial polysaccharide in rheumatoid synovial effusions. Arthritis Rheum. 1979 Sep;22(9):969-77. Pubmed: 314293 Link_out
  16. 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. Pubmed: 10571726 Link_out
  17. Bukowska B, Kowalska S: Phenol and catechol induce prehemolytic and hemolytic changes in human erythrocytes. Toxicol Lett. 2004 Aug 30;152(1):73-84. Pubmed: 15294349 Link_out
  18. 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. Pubmed: 15840783 Link_out

Enzymes
Name: Serum paraoxonase/lactonase 3
Reactions: Not Available
Gene Name: PON3
Uniprot ID: Q15166 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serum paraoxonase/arylesterase 1
Reactions: Not Available
Gene Name: PON1
Uniprot ID: P27169 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serum paraoxonase/arylesterase 2
Reactions: Not Available
Gene Name: PON2
Uniprot ID: Q15165 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphogluconolactonase
Reactions: Not Available
Gene Name: PGLS
Uniprot ID: O95336 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphate 1-dehydrogenase
Reactions: Not Available
Gene Name: G6PD
Uniprot ID: P11413 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sulfotransferase 1A1
Reactions:
Phosphoadenosine phosphosulfate + Phenol unknown Adenosine 3',5'-diphosphate + Phenol sulphate details
Gene Name: SULT1A1
Uniprot ID: P50225 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sulfotransferase 1A2
Reactions:
Phosphoadenosine phosphosulfate + Phenol unknown Adenosine 3',5'-diphosphate + Phenol sulphate details
Gene Name: SULT1A2
Uniprot ID: P50226 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sulfotransferase 1A3/1A4
Reactions:
Phosphoadenosine phosphosulfate + Phenol unknown Adenosine 3',5'-diphosphate + Phenol sulphate details
Gene Name: SULT1A3
Uniprot ID: P50224 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphogluconate dehydrogenase, decarboxylating
Reactions: Not Available
Gene Name: PGD
Uniprot ID: P52209 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier family 13 member 4
Reactions: Not Available
Gene Name: SLC13A4
Uniprot ID: Q9UKG4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative uncharacterized protein PGD
Reactions: Not Available
Gene Name: PGD
Uniprot ID: A9Z1X1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA