ContaminantDB: Phenolphthalein

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (12)XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:05:52 UTC

Update Date

2016-11-09 01:09:11 UTC

Accession Number

CHEM003666

Identification

Common Name

Phenolphthalein

Class

Small Molecule

Description

Phenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Modane	Kegg
3,3-Bis(4-hydroxyphenyl)phthalide	Kegg
Ap-la-day	MeSH
Mentholatum brand OF phenolphthalein	MeSH
Novartis brand OF phenolphthalein	MeSH
Schering-plough brand OF phenolphthalein	MeSH
Ex-lax	MeSH
manesco Brand OF phenolphthalein	MeSH
Thalinol	MeSH
Laxettes	MeSH
Feen-a-mint	MeSH
Key brand OF phenolphthalein	MeSH
Laxatone	MeSH
Thompson brand OF phenolphthalein	MeSH

Chemical Formula

C₂₀H₁₄O₄

Average Molecular Mass

318.323 g/mol

Monoisotopic Mass

318.089 g/mol

CAS Registry Number

77-09-8

IUPAC Name

3,3-bis(4-hydroxyphenyl)-1,3-dihydro-2-benzofuran-1-one

Traditional Name

phenolphthalein

SMILES

OC1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1

InChI Identifier

InChI=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 Key

KJFMBFZCATUALV-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Benzofuranones

Direct Parent

Benzofuranones

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:34914 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	262.5°C
Boiling Point	Not Available
Solubility	400 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0099 g/L	ALOGPS
logP	4.41	ALOGPS
logP	4.35	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.04 m³·mol⁻¹	ChemAxon
Polarizability	32.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-2592000000-d2bcec49a8083604a09a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-2950000000-2239a8a809fdd9396eaf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-2950000000-2239a8a809fdd9396eaf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0006-9000000000-7a5eb6309afb884c913c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0006-9020000000-4bd55923e6b1a862ccdb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014l-0900000000-b5db4dfe68685f5d0076	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00kf-0900000000-972ff44a32df263bacd4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0006-9000000000-5eb567dd72ea0ec54c42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-9020000000-0df8205f0ce2cb779ee4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-004m-0930000000-9bb4dffb81d39cc30175	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-004i-0290000000-582ef3c15cb87c4c8c15	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0019000000-333e80eef9eaed246bcc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0091000000-3949fe0e9e4846cf5036	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0006-9000000000-494b0cf212c721029bcc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0006-9000000000-4329eccdfee4b908e0ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-ea673bbdb67658cda386	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0149000000-edeb6f7d40e6c2a246a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-5690000000-b9f1fb8a1e6a00ac4204	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0019000000-2f93262e833438931955	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-0098000000-be431006a7dc4593473d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-4090000000-b1557e38634d0b6eabb4	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00fr-2690000000-8c929a0403799e4cd208	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (1)

Uses/Sources

Used for over a century as a laxative.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB04824

HMDB ID

HMDB0256412

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Phenolphthalein

Chemspider ID

4600

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C14286

YMDB ID

Not Available

ECMDB ID

Not 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.

MSDS

Not Available

General References

Not Available

Phenolphthalein (CHEM003666)

Structure for CHEM003666: Phenolphthalein