Phosphoric acid, mixed esters with [1,1'-biphenyl]-4,4'-diol and phenol (CHEM008942)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:55:29 UTC
Update Date2016-11-09 01:13:53 UTC
Accession NumberCHEM008942
Identification
Common NamePhosphoric acid, mixed esters with [1,1'-biphenyl]-4,4'-diol and phenol
ClassSmall Molecule
DescriptionPhenol is 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. Phenol has been used to disinfect skin and to relieve itching. Phenol is also used as an oral analgesic or anesthetic in products such as Chloraseptic to treat pharyngitis. Additionally, phenol and its related compounds are used in surgical ingrown toenail treatment, a process termed phenolization. Research indicates that parental exposure to phenol and its related compounds are positively associated with spontaneous abortion. During the second world war, phenol injections were used as a means of execution by the Nazis. Phenol is a toxic compound whose vapours are corrosive to the skin, eyes, and respiratory tract.
Contaminant Sources
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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 Number1003300-73-9
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
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-3900000000-97dfa3be718a9ee7ace4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-6fb456992902a13931f9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-78c83ab6ff1d3dfdbec6Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-89b0c430b8924ee2afdeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-fc01d0ad6740cfd70e13Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006w-9000000000-c8b41f2899ca8cc9d4bcSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-db80d8b605e20595c679Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-3900000000-97dfa3be718a9ee7ace4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-c35c89484e2499c62a49Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g4i-9300000000-afd565a878ea36c74defSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-9000000000-e67da0571423f0e6b4b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-e0f57b1e970d0d46597eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-e67da0571423f0e6b4b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kf-9000000000-7bfe3b897e928a8f3a2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-0006-9000000000-78c83ab6ff1d3dfdbec6Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0006-9000000000-89b0c430b8924ee2afdeSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0006-9000000000-fc01d0ad6740cfd70e13Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-ca4fa5905cccbfeab33aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-e3e33defb000b450bb37Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-d63db79771e5931b258fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-448a4d79ff53d77a8b16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-2c7201e803e029dd1aefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-3fb3990dfbfbde2b8d57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gba-9000000000-d3da8db6579f32d02c6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-a74494cda18ab9fb8055Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-a74494cda18ab9fb8055Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-03a61ff7da92cb08edf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-c65d4a4eaa8adde2ddb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-9000000000-def7a8d52afb63a3cd67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-f3c795ffc788635ddbf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-08485aaf085c13d5129aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-08485aaf085c13d5129aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-52b0f93832ef13f17bd2Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kf-9000000000-40b376f4e58c23369a01Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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 ReferenceNot Available
MSDSNot Available
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.
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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.
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