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77-09-8 molecular structure
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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 and InChIs

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

Cite this record

CBID:4368 http://www.chembase.cn/molecule-4368.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
77-09-8
EC Number
201-004-7
MDL Number
MFCD00005913
Beilstein Number
284423
Merck Index
147243
PubChem SID
24860295
160967800
24849859
24861367
24859151
24899058
24863124
46506108
24861366
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.1574335  H Acceptors
H Donor LogD (pH = 5.5) 4.3532066 
LogD (pH = 7.4) 4.345787  Log P 4.3533015 
Molar Refractivity 91.0373 cm3 Polarizability 34.39085 Å3
Polar Surface Area 66.76 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.41  LOG S -4.51 
Solubility (Water) 9.92e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.4 mg/mL [YALKOWSKY,SH & HE,Y (2003)] expand Show data source
acetone: soluble expand Show data source
Insoluble in benzene, very soluble in ethanol and ether, slightly soluble in DMSO expand Show data source
Insoluble in water expand Show data source
Soluble in alcohol. Slightly soluble in ether expand Show data source
Apperance
Liquid expand Show data source
Powder expand Show data source
S. No.: 879 expand Show data source
Melting Point
258-262 °C (497-504 °F) expand Show data source
258-262°C expand Show data source
260 °C expand Show data source
261 - 263°C expand Show data source
261-263 °C(lit.) expand Show data source
Boiling Point
Decomposes before boiling expand Show data source
N/A expand Show data source
Flash Point
11 °C expand Show data source
14 °C expand Show data source
24 °C expand Show data source
24°C(76°F) expand Show data source
51.8 °F expand Show data source
57.2 °F expand Show data source
75.2 °F expand Show data source
Density
0.918 expand Show data source
0.918 g/mL at 25 °C expand Show data source
1.277 g cm-3, at 32 °C expand Show data source
1.299 expand Show data source
1.299 (water = 1) expand Show data source
Vapor Pressure
Extremely low expand Show data source
Absorption Wavelength
λmax 374 nm (2nd) expand Show data source
λmax 552 nm expand Show data source
Hydrophobicity(logP)
2.41 [HANSCH,C ET AL. (1995), pH 7.4] expand Show data source
3.729 expand Show data source
pH
7.8-10.0 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
SM8380000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Toxic Toxic (T) expand Show data source
UN Number
1170 expand Show data source
1230 expand Show data source
UN1986 expand Show data source
UN1987 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
3 expand Show data source
II expand Show data source
Risk Statements
10 expand Show data source
11-23/24/25-39/23/24/25 expand Show data source
45-10-68 expand Show data source
45-11-20/21/22-39/23/24/25-68 expand Show data source
45-11-20/21/22-68/20/21/22 expand Show data source
45-11-68 expand Show data source
45-62-68 expand Show data source
45-68 expand Show data source
R:45-36/37/38 expand Show data source
Safety Statements
16-36/37-45 expand Show data source
53-16-36/37-45 expand Show data source
53-36/37-45 expand Show data source
53-45 expand Show data source
53-7/9-16-23-36/37/39-45-60 expand Show data source
S:28-29-36/37/39-45-53 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
Warning expand Show data source
GHS Hazard statements
H225-H301 + H311 + H331-H370 expand Show data source
H225-H341-H350 expand Show data source
H225-H350-H370-H341-H313-H333 expand Show data source
H225-H350-H371-H302-H312-H332 expand Show data source
H226 expand Show data source
H226-H341-H350 expand Show data source
H341-H350 expand Show data source
H341-H350-H361 expand Show data source
H350-H341-H361 expand Show data source
GHS Precautionary statements
P201-P210-P281-P308 + P313 expand Show data source
P201-P281-P308 + P313 expand Show data source
P210-P241-P260-P303+P361+P353-P405-P501A expand Show data source
P210-P260-P280-P301 + P310-P311 expand Show data source
P281-P201-P202-P308+P313-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
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 expand Show data source
RID/ADR
UN 1170 3/PG 3 expand Show data source
UN 1230 3/PG 2 expand Show data source
Mechanism of Action
Alters electrolyte-secretion expand Show data source
Alters water-secretion expand Show data source
Direct action on intestinal mucosa expand Show data source
Requires bile for activity expand Show data source
Stimulates myenteric-plexus expand Show data source
Purity
≥97.0% expand Show data source
≥98.0% expand Show data source
0.5% w/v in alcohol expand Show data source
1% w/v in alcohol expand Show data source
95% expand Show data source
98% expand Show data source
98-101% (calc. to the dried substance) expand Show data source
98-102% (calc. to the dried substance) expand Show data source
Concentration
0.04 % (w/v) expand Show data source
0.1 % (w/v) expand Show data source
0.375% in methanol expand Show data source
0.5 wt. % in ethanol: water (1:1) expand Show data source
0.5% w/v in alcohol expand Show data source
1 % (w/v) expand Show data source
1% in ethanol expand Show data source
2% in ethanol expand Show data source
Grade
ACS expand Show data source
ACS reagent expand Show data source
ACS reagent, reag. Ph. Eur. expand Show data source
DAB 6 expand Show data source
indicator expand Show data source
JIS special grade expand Show data source
NF expand Show data source
puriss. expand Show data source
puriss. p.a. expand Show data source
Reag. Ph. Eur. expand Show data source
REAGENT expand Show data source
SAJ first grade expand Show data source
USP expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
in accordance for appearance of solution expand Show data source
in accordance for suitability as indicator expand Show data source
in accordance for test of sensitivity expand Show data source
passes test for change expand Show data source
passes test for indicator expand Show data source
passes test for test of sensitivity expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
Impurities
≤0.001% heavy metals (as Pb) expand Show data source
≤0.1% sulfated ash expand Show data source
acidic and alkalic reac. substances, in accordance expand Show data source
related subst., in accordance expand Show data source
residual solvents, complies expand Show data source
Antion Traces
chloride (Cl-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤200 mg/kg expand Show data source
Loss on Drying
≤0.5% loss on drying, 105 °C expand Show data source
≤1% loss on drying, 105 °C expand Show data source
Application(s)
Laxatives expand Show data source
Visual Transition Interval
7.2 - 10.0 (corresponds) expand Show data source
8.0 - 10, colorless to red expand Show data source
Quality
meets analytical specification of Ph Eur., BP expand Show data source
Empirical Formula (Hill Notation)
C20H14O4 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05216578 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02102608 external link
pH interval: 8.2-9.8
MP Biomedicals - 02191424 external link
ACS Reagent Grade
DrugBank - DB04824 external link
Item Information
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 external link
General description
Visit our Titration Center to learn more.
Sigma Aldrich - 40-1022 external link
Suitability
for titration
Sigma Aldrich - 40-1023 external link
Suitability
for titration
Sigma Aldrich - 105945 external link
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 external link
Packaging
100 mL in glass bottle
Sigma Aldrich - 31316 external link
Packaging
1 roll with approx. 5 m
Sigma Aldrich - 34606 external link
General description
Visit our Titration Center to learn more.
Sigma Aldrich - 40-2031 external link
Suitability
pH indicator

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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.
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