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Record Information
Version1.0
Creation Date2014-09-11 02:05:52 UTC
Update Date2016-11-09 01:09:11 UTC
Accession NumberCHEM003666
Identification
Common NamePhenolphthalein
ClassSmall Molecule
DescriptionPhenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.
Contaminant Sources
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Ester
  • Ether
  • Household Toxin
  • Indicator and Reagent
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
ModaneKegg
3,3-Bis(4-hydroxyphenyl)phthalideKegg
Ap-la-dayMeSH
Mentholatum brand OF phenolphthaleinMeSH
Novartis brand OF phenolphthaleinMeSH
Schering-plough brand OF phenolphthaleinMeSH
Ex-laxMeSH
manesco Brand OF phenolphthaleinMeSH
ThalinolMeSH
LaxettesMeSH
Feen-a-mintMeSH
Key brand OF phenolphthaleinMeSH
LaxatoneMeSH
Thompson brand OF phenolphthaleinMeSH
Chemical FormulaC20H14O4
Average Molecular Mass318.323 g/mol
Monoisotopic Mass318.089 g/mol
CAS Registry Number77-09-8
IUPAC Name3,3-bis(4-hydroxyphenyl)-1,3-dihydro-2-benzofuran-1-one
Traditional Namephenolphthalein
SMILESOC1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C20H14O4/c21-15-9-5-13(6-10-15)20(14-7-11-16(22)12-8-14)18-4-2-1-3-17(18)19(23)24-20/h1-12,21-22H
InChI KeyKJFMBFZCATUALV-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
  • Isobenzofuranone
  • Isocoumaran
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point262.5°C
Boiling PointNot Available
Solubility400 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.0099 g/LALOGPS
logP4.41ALOGPS
logP4.35ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.16ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity91.04 m³·mol⁻¹ChemAxon
Polarizability32.65 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-2592000000-d2bcec49a8083604a09aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-2950000000-2239a8a809fdd9396eafSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-2950000000-2239a8a809fdd9396eafSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0006-9000000000-7a5eb6309afb884c913cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0006-9020000000-4bd55923e6b1a862ccdbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-014l-0900000000-b5db4dfe68685f5d0076Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-00kf-0900000000-972ff44a32df263bacd4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0006-9000000000-5eb567dd72ea0ec54c42Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-9020000000-0df8205f0ce2cb779ee4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-004m-0930000000-9bb4dffb81d39cc30175Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-004i-0290000000-582ef3c15cb87c4c8c15Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014i-0019000000-333e80eef9eaed246bccSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0091000000-3949fe0e9e4846cf5036Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0006-9000000000-494b0cf212c721029bccSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0006-9000000000-4329eccdfee4b908e0abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-ea673bbdb67658cda386Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0149000000-edeb6f7d40e6c2a246a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-5690000000-b9f1fb8a1e6a00ac4204Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-2f93262e833438931955Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-0098000000-be431006a7dc4593473dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4090000000-b1557e38634d0b6eabb4Spectrum
MSMass Spectrum (Electron Ionization)splash10-00fr-2690000000-8c929a0403799e4cd208Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (1)
Uses/SourcesUsed for over a century as a laxative.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04824
HMDB IDHMDB0256412
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhenolphthalein
Chemspider ID4600
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDC14286
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Hershel B. Prindle, George E. Ham, “Preparation of phenolphthalein using cation exchange resins and aryl phosphites.” U.S. Patent US4252725, issued March, 1966.

MSDSNot Available
General ReferencesNot Available