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

• ChemBase ID: 4368
• Molecular Formular: C20H14O4
• Molecular Mass: 318.32276
• Monoisotopic Mass: 318.08920893
• SMILES: O1C(c2c(C1=O)cccc2)(c1ccc(O)cc1)c1ccc(O)cc1
• Canonical SMILES: Oc1ccc(cc1)C1(OC(=O)c2c1cccc2)c1ccc(cc1)O
• InChI: 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
• InChIKey: KJFMBFZCATUALV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,3-bis(4-hydroxyphenyl)-1,3-dihydro-2-benzofuran-1-one
• IUPAC Traditional name: 3,3-bis(4-hydroxyphenyl)-1,3-dihydro-2-benzofuran-1-one; purga
• Brand Name: Agoral; Alophen; Chocolax; Colax; Correctol; Doxan; Doxidan; Espotabs; Euchessina; Evac-q-kit; Evac-q-kwik; Evac-q-tabs; Evac-u-gen; Evac-v-lax; Ex-lax; Feen-a-mint gum; Feen-a-mint laxative mints; Femilax; Koprol; LILO; Lax-pills; Laxcaps; Laxin; Laxogen; Medilax; Modane; Modane plus; Phenolax; Phillips gelcaps; Phthalimetten; Phthalin; Prulet; Purga; Purgen; Purgophen; Spulmako-lax; Trilax
• Synonyms: 3,3-bis(4-hydroxyphenyl)-1,3-dihydro-2-benzofuran-1-one; Phenolphthalein, ACS; Phenolphthalein Paper; Trihydroxytriphenylmethane-2-carboxylic acid lactone; PHENOLPHTHALEIN ACS REAGENT GRADE; 3,3-bis[4-Hydroxyphenyl]-1-[3H]-isobenzofuranone; PHENOLPHTHALEIN USP/NF GRADE; Phenolphthalein; Phenolphthalein solution; 3,3-Bis(4-hydroxyphenyl)-1(3H)-isobenzofuranone; 3,3-Bis(4-hydroxyphenyl)-2-benzofuran-1(3H)-one; 3,3-Bis(p-hydroxyphenyl)phthalide; 3,3-Bis(4-hydroxyphenyl)phthalide; Alpha-di(p-hydroxyphenyl)phthalide; Dihydroxyphthalophenone; Fenolftalein [czech]; Fenolftaleina [inn-spanish]; Phenolphtaleine [inn-french]; Phenolphthaleinum [inn-latin]; Phenophthalein; Phenolphthalein; 酚酞; 酚酞, ACS; 酚酞试纸; 3,3-双(4-羟基苯基)-1(3H)-异苯并呋喃酮; Phenolphthalein; 酚酞 溶液

Database IDs

• CAS Number: 77-09-8
• EC Number: 201-004-7
• MDL Number: MFCD00005913
• Beilstein Number: 284423
• Merck Index: 147243
• PubChem SID: 24860295; 46506108; 24861366; 24899058; 24863124; 160967800; 24849859; 24861367; 24859151; 24846716; 24861369
• PubChem CID: 4764
• ATC CODE: A06AB04
• CHEMBL: 63857
• Chemspider ID: 4600
• DrugBank ID: DB04824
• KEGG ID: D05456
• Wikipedia Title: Phenolphthalein
• Color Index Number: 764

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.1574335
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.3532066
• LogD (pH = 7.4): 4.345787
• Log P: 4.3533015
• Molar Refractivity: 91.0373 cm^3
• Polarizability: 34.39085 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.41
• LOG S: -4.51
• Solubility (Water): 9.92e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.4 mg/mL [YALKOWSKY,SH & HE,Y (2003)]; acetone: soluble; Insoluble in benzene, very soluble in ethanol and ether, slightly soluble in DMSO; Insoluble in water; Soluble in alcohol. Slightly soluble in ether
• Apperance: Liquid; Powder; S. No.: 879
• Melting Point: 258-262 °C (497-504 °F); 258-262°C; 260 °C; 261 - 263°C; 261-263 °C(lit.)
• Boiling Point: Decomposes before boiling; N/A
• Flash Point: 11 °C; 14 °C; 24 °C; 24°C(76°F); 51.8 °F; 57.2 °F; 75.2 °F
• Density: 0.918; 0.918 g/mL at 25 °C; 1.277 g cm^-3, at 32 °C; 1.299; 1.299 (water = 1)
• Vapor Pressure: Extremely low
• Absorption Wavelength: λmax 374 nm (2nd); λmax 552 nm
• Hydrophobicity(logP): 2.41 [HANSCH,C ET AL. (1995), pH 7.4]; 3.729
• pH: 7.8-10.0

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: SM8380000
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1170; 1230; UN1986; UN1987
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; 3; II
• Risk Statements: 10; 11-23/24/25-39/23/24/25; 45-10-68; 45-11-20/21/22-39/23/24/25-68; 45-11-20/21/22-68/20/21/22; 45-11-68; 45-62-68; 45-68; R:45-36/37/38
• Safety Statements: 16-36/37-45; 53-16-36/37-45; 53-36/37-45; 53-45; 53-7/9-16-23-36/37/39-45-60; S:28-29-36/37/39-45-53
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H301 + H311 + H331-H370; H225-H341-H350; H225-H350-H370-H341-H313-H333; H225-H350-H371-H302-H312-H332; H226; H226-H341-H350; H341-H350; H341-H350-H361; H350-H341-H361
• GHS Precautionary statements: P201-P210-P281-P308 + P313; P201-P281-P308 + P313; P210-P241-P260-P303+P361+P353-P405-P501A; P210-P260-P280-P301 + P310-P311; P281-P201-P202-P308+P313-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1170 3/PG 3; UN 1230 3/PG 2

Pharmacology Properties

• Mechanism of Action: Alters electrolyte-secretion; Alters water-secretion; Direct action on intestinal mucosa; Requires bile for activity; Stimulates myenteric-plexus

Product Information

• Purity: ≥97.0%; ≥98.0%; 0.5% w/v in alcohol; 1% w/v in alcohol; 95%; 98%; 98-101% (calc. to the dried substance); 98-102% (calc. to the dried substance)
• Concentration: 0.04 % (w/v); 0.1 % (w/v); 0.375% in methanol; 0.5 wt. % in ethanol: water (1:1); 0.5% w/v in alcohol; 1 % (w/v); 1% in ethanol; 2% in ethanol
• Grade: ACS; ACS reagent; ACS reagent, reag. Ph. Eur.; DAB 6; indicator; JIS special grade; NF; puriss.; puriss. p.a.; Reag. Ph. Eur.; REAGENT; SAJ first grade; USP
• Suitability: in accordance for appearance of solution; in accordance for suitability as indicator; in accordance for test of sensitivity; passes test for change; passes test for indicator; passes test for test of sensitivity
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ≤0.001% heavy metals (as Pb); ≤0.1% sulfated ash; acidic and alkalic reac. substances, in accordance; related subst., in accordance; residual solvents, complies
• Antion Traces: chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): ≤200 mg/kg
• Loss on Drying: ≤0.5% loss on drying, 105 °C; ≤1% loss on drying, 105 °C
• Application(s): Laxatives
• Visual Transition Interval: 7.2 - 10.0 (corresponds); 8.0 - 10, colorless to red
• Quality: meets analytical specification of Ph Eur., BP
• Empirical Formula (Hill Notation): C20H14O4

DETAILS

MP Biomedicals - 05216578

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102608

pH interval: 8.2-9.8

MP Biomedicals - 02191424

ACS Reagent Grade

DrugBank - DB04824

• Drug Groups: withdrawn
• Description: Phenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.
• Indication: Used for over a century as a laxative.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Sigma Aldrich - 34605

General description
Visit our Titration Center to learn more.

Sigma Aldrich - 40-1022

Suitability
for titration

Sigma Aldrich - 40-1023

Suitability
for titration

Sigma Aldrich - 105945

Packaging
2.5 kg in poly drum
50, 100, 500 g in poly bottle
Application
Phenolphthalein is used as a general pH indicator. It is colorless in acidic solutions and turns pink in basic solutions. Phenolphthalein is also used as a model organic compound in the evaluation of the capture efficiency of various cyclodextrin constructs such as nanofiber-CD.

Sigma Aldrich - 319236

Packaging
100 mL in glass bottle

Sigma Aldrich - 31316

Packaging
1 roll with approx. 5 m

Sigma Aldrich - 34606

General description
Visit our Titration Center to learn more.

Sigma Aldrich - 40-2031

Suitability
pH indicator

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1006B, (ir)
• Baeyer, A., Annalen, 1880, 202, 69, (synth)
• Underwood, H.W. et al., J.A.C.S., 1930, 52, 4084
• Blicke, F.F. et al., J.A.C.S., 1932, 54, 332
• Hubacher, M.H. et al., J. Am. Pharm. Assoc., 1953, 42, 23
• Maute, R.L. et al., Anal. Chem., 1954, 26, 1723, (detn, CN(-))
• Davies, M. et al., J.C.S., 1954, 120, (ir)
• Ziegler, E. et al., Monatsh. Chem., 1969, 100, 1604, (pmr)
• Rousselet, R., J. Pharm. Belg., 1971, 26, 568, (ir, tlc)
• Bishop, E., Indicators, Pergamon, Oxford, 1972, 92; 192, (use)
• Holzbecher, Z. et al., Handbook of Organic Reagents in Inorganic Analysis, Horwood, Chichester, 1976, (use)
• Houben-Weyl, Methoden Org. Chem. (Houben-Weyl), 4th edn., (Wedemeyer, K.F., Ed.), 1976, 1093
• Shahine, S.A. et al., Microchem. J., 1976, 21, 286, (detn, Cl(-))
• Shahine, S.A. et al., Mikrochim. Acta, 1978, 2, 431, (detn, N2H4)
• Berger, S., Tetrahedron, 1981, 37, 1607, (cmr, tautom)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5553, (synonyms)
• Al-Shammary, F.J. et al., Anal. Profiles Drug Subst., 1991, 20, 627, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 899
• Fitzgerald, L.J. et al., Acta Cryst. C, 1998, 54, 535-539, (cryst struct)
• Sigma-Aldrich Library of Stains, Dyes and Indicators, 563
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PDO750
• Acid-base indicator: pH 8.0 - 10.0.