Phenol red (CHEM016533)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:36:14 UTC
Update Date2016-11-09 01:15:25 UTC
Accession NumberCHEM016533
Identification
Common NamePhenol red
ClassSmall Molecule
Description3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,3-Bis(p-hydroxyphenyl)-3H-2,1-benzoxathiole 1,1-dioxideChEBI
4,4'-(3H-2,1-Benzoxathiol-3-ylidene)bisphenol S,S-dioxideChEBI
alpha-Hydroxy-alpha,alpha-bis(p-hydroxyphenyl)-O-toluenesulfonic acid gamma-sultoneChEBI
PSPChEBI
Phenol redKegg
a-Hydroxy-a,a-bis(p-hydroxyphenyl)-O-toluenesulfonate g-sultoneGenerator
a-Hydroxy-a,a-bis(p-hydroxyphenyl)-O-toluenesulfonic acid g-sultoneGenerator
a-Hydroxy-a,a-bis(p-hydroxyphenyl)-O-toluenesulphonate g-sultoneGenerator
a-Hydroxy-a,a-bis(p-hydroxyphenyl)-O-toluenesulphonic acid g-sultoneGenerator
alpha-Hydroxy-alpha,alpha-bis(p-hydroxyphenyl)-O-toluenesulfonate gamma-sultoneGenerator
alpha-Hydroxy-alpha,alpha-bis(p-hydroxyphenyl)-O-toluenesulphonate gamma-sultoneGenerator
alpha-Hydroxy-alpha,alpha-bis(p-hydroxyphenyl)-O-toluenesulphonic acid gamma-sultoneGenerator
Α-hydroxy-α,α-bis(p-hydroxyphenyl)-O-toluenesulfonate γ-sultoneGenerator
Α-hydroxy-α,α-bis(p-hydroxyphenyl)-O-toluenesulfonic acid γ-sultoneGenerator
Α-hydroxy-α,α-bis(p-hydroxyphenyl)-O-toluenesulphonate γ-sultoneGenerator
Α-hydroxy-α,α-bis(p-hydroxyphenyl)-O-toluenesulphonic acid γ-sultoneGenerator
PhenolsulphonphthaleinGenerator
PhenolsulfonphthaleinChEBI
SulphentalMeSH
SulfonphthalMeSH
SulphonthalMeSH
Chemical FormulaC19H14O5S
Average Molecular Mass354.380 g/mol
Monoisotopic Mass354.056 g/mol
CAS Registry Number143-74-8
IUPAC Name3,3-bis(4-hydroxyphenyl)-3H-2,1λ⁶-benzoxathiole-1,1-dione
Traditional Namephenol red
SMILESOC1=CC=C(C=C1)C1(OS(=O)(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C19H14O5S/c20-15-9-5-13(6-10-15)19(14-7-11-16(21)12-8-14)17-3-1-2-4-18(17)25(22,23)24-19/h1-12,20-21H
InChI KeyBELBBZDIHDAJOR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassBenzofuranones
Direct ParentBenzofuranones
Alternative Parents
Substituents
  • Benzofuranone
  • Phthalide
  • Benzoxathiole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Organosulfonic acid ester
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.018 g/LALOGPS
logP3.15ALOGPS
logP4.11ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.16ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.12 m³·mol⁻¹ChemAxon
Polarizability34.9 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-074i-0690000000-1fe446831f73ff7b222fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0019000000-59844b86965c49a2143aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1229000000-81d7a1744afb2c178bd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4920000000-11e77785252e516ea0f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-9729846d5b4e032ab8ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-4039000000-df0dec6230165e2817faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9141000000-2fbcd4af9690dbf2b6d1Spectrum
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 IDDB13212
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhenol red
Chemspider IDNot Available
ChEBI ID31991
PubChem Compound IDNot Available
Kegg Compound IDC12600
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available