Phenolphthalein

This article is about Phenolphthalein. For other related dyes in the phthalein family, see Phthalein dye.
Phenolphthalein

Names
Preferred IUPAC name
3,3-Bis(4-hydroxyphenyl)-2-benzofuran-1(3H)-one
Other names
3,3-Bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one
Identifiers
CAS Number
77-09-8 check
3D model (JSmol)
Interactive image
ChEMBL
ChEMBL63857 check
ChemSpider
4600 check
DrugBank
þÿDB04824 &
ECHA InfoCard 100.000.914 Edit this at Wikidata
KEGG
D05456 check
PubChem CID
4764
UNII
þÿ6QK969R2IF &
CompTox Dashboard (EPA)
DTXSID0021125 Edit this at Wikidata
InChI
SMILES
Properties
Chemical formula C20H14O4
þÿMolar mass 318.328 g·mol"1
Appearance White powder
Density 1.277 g/cm3 (32 °C (90 °F))
þÿMelting point 258 263 °C (496 505 °F; 531 536 K)[1]
Solubility in water 400 mg/l
Solubility in other solvents Insoluble in benzene and hexane; very soluble in ethanol and ether; slightly soluble
in DMSO
þÿUV-vis (»max) 552 nm (1st)
374 nm (2nd)[1]
Pharmacology
ATC code A06AB04 (WHO)
Hazards
GHS labelling:
Pictograms GHS08: Health hazard[1]
Signal word Danger
Hazard statements H341, H350, H361[1]
Precautionary statements P201, P281, P308+P313[1]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond230
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
þÿ& verify (what is check& ?)
Infobox references
þÿPhenolphthalein (/f[ÈnRl(f)¸YliÐn/[citation needed] feh-NOL(F)-thY-leen) is a chemical compound with the
formula C20H14O4 and is often written as "HIn", "HPh", "phph" or simply "Ph" in shorthand notation.
þÿPhenolphthalein is often used as an indicator in acid base titrations. For this application, it turns colorless in
acidic solutions and pink in basic solutions. It belongs to the class of dyes known as phthalein dyes.

Phenolphthalein is slightly soluble in water and usually is dissolved in alcohols in experiments. It is a weak
acid, which can lose H+ ions in solution. The nonionized phenolphthalein molecule is colorless and the double
deprotonated phenolphthalein ion is fuchsia. Further proton loss in higher pH occurs slowly and leads to a
colorless form. Phenolphthalein ion in concentrated sulfuric acid is orange red due to sulfonation.[2]

Uses
pH indicator
Phenolphthalein (pH indicator)
below pH 8.3 above pH 10.0
þÿ8.3 !Ì 10.0
Phenolphthalein's common use is as an indicator in acid-base titrations. It also serves as a component of
universal indicator, together with methyl red, bromothymol blue, and thymol blue.[3]
Phenolphthalein adopts different forms in aqueous solution depending on the pH of the solution.[4][2][5][6]
Inconsistency exists in the literature about hydrated forms of the compounds and the color of sulfuric acid.
Wittke reported in 1983 that it exists in protonated form (HIn+)under strongly acidic conditions, providing an
orange coloration. However, a later paper suggested that this color is due to sulfonation to
phenolsulfonphthalein.[2]

The lactone form (HIn) is colorless between strongly acidic and slightly basic conditions. The doubly
deprotonated (In2-) phenolate form (the anion form of phenol) gives the familiar pink color. In strongly basic
þÿsolutions, phenolphthalein is converted to its In(OH)3" form, and its pink color undergoes a rather slow fading
reaction[6] and becomes completely colorless when pH is greater than 13.

The pKa values of phenolphthalein were found to be 9.05, 9.50 and 12 while those of phenolsulfonphthalein are
1.2 and 7.70.[2]

Carbonation of concrete
Phenolphthalein's pH sensitivity is exploited in other applications: concrete has naturally high pH due to the
calcium hydroxide formed when Portland cement reacts with water. As the concrete reacts with carbon dioxide
þÿin the atmosphere, pH decreases to 8.5 9. When a 1% phenolphthalein solution is applied to normal concrete, it
turns bright pink. However, if it remains colorless, it shows that the concrete has undergone carbonation. In a
similar application, some spackling used to repair holes in drywall contains phenolphthalein. When applied, the
basic spackling material retains a pink color; when the spackling has cured by reaction with atmospheric carbon
dioxide, the pink color fades.[8]

Education
In a highly basic solution, phenolphthalein's slow change from pink to colorless as it is converted to its
þÿPh(OH)3" form is used in chemistry classes for the study of reaction kinetics.

Entertainment
Phenolphthalein is used in toys, for example as a component of disappearing inks, or disappearing dye on the
"Hollywood Hair" Barbie hair. In the ink, it is mixed with sodium hydroxide, which reacts with carbon dioxide
in the air. This reaction leads to the pH falling below the color change threshold as hydrogen ions are released
by the reaction:

þÿOH"(aq) + CO2(g) !’ CO2"

3(aq) + H+(aq).
To develop the hair and "magic" graphical patterns, the ink is sprayed with a solution of hydroxide, which leads
to the appearance of the hidden graphics by the same mechanism described above for color change in alkaline
solution. The pattern will eventually disappear again because of the reaction with carbon dioxide.
Thymolphthalein is used for the same purpose and in the same way, when a blue color is desired.[9]

Detection of blood
Main article: Kastle-Meyer test
A reduced form of phenolphthalein, phenolphthalin, which is colorless, is used in a test to identify substances
þÿthought to contain blood, commonly known as the Kastle Meyer test. A dry sample is collected with a swab or
filter paper. A few drops of alcohol, then a few drops of phenolphthalin, and finally a few drops of hydrogen
peroxide are dripped onto the sample. If the sample contains hemoglobin, it will turn pink immediately upon
addition of the peroxide, because of the generation of phenolphthalein. A positive test indicates the sample
contains hemoglobin and, therefore, is likely blood. A false positive can result from the presence of substances
with catalytic activity similar to hemoglobin. This test is not destructive to the sample; it can be kept and used
in further tests. This test has the same reaction with blood from any animal whose blood contains hemoglobin,
including almost all vertebrates; further testing would be required to determine whether it originated from a
human.

Laxative
See also: Phenol red
Phenolphthalein has been used for over a century as a laxative, but is now being removed from over-the-counter
laxatives[10] over concerns of carcinogenicity.[11][12] Laxative products formerly containing phenolphthalein
have often been reformulated with alternative active ingredients: Feen-a-Mint[13] switched to bisacodyl and
Ex-Lax[14] was switched to a senna extract.

Thymolphthalein is a related laxative made from thymol.

Despite concerns regarding its carcinogenicity based on rodent studies, the use of phenolphthalein as a laxative
is unlikely to cause ovarian cancer.[15] Some studies suggest a weak association with colon cancer, while
others show none at all.[16]

Phenolphthalein is described as a stimulant laxative.[16] In addition, it has been found to inhibit human cellular
calcium influx via store-operated calcium entry (SOCE, see Calcium release activated channel § Structure) in
vivo. This is effected by its inhibiting thrombin and thapsigargin, two activators of SOCE that increase
intracellular free calcium.[17]

Phenolphthalein has been added to the European Chemicals Agency's candidate list for substance of very high
concern (SVHC).[18] It is on the IARC group 2B list for substances "possibly carcinogenic to humans".[19]
The discovery of phenolphthalein's laxative effect was due to an attempt by the Hungarian government to
label[clarification needed] genuine local white wine with the substance in 1900. Phenolphthalein did not change
the taste of the wine and would change color when a base is added, making it a good label on paper. However, it
was found that ingestion of the substance led to diarrhea. Max Kiss, a Hungarian-born pharmacist residing in
New York, heard about the news and launched Ex-Lax in 1906.[20][19]

Synthesis
Phenolphthalein can be synthesized by condensation of phthalic anhydride with two equivalents of phenol
under acidic conditions. It was discovered in 1871 by Adolf von Baeyer.[21][22][23]