The
ferric chloride
Iron(III) chloride describes the inorganic compounds with the formula (H2O)x. Also called ferric chloride, these compounds are some of the most important and commonplace compounds of iron. They are available both in anhydrous and in hydrated f ...
test is used to determine the presence of
phenols
In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (− O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds ar ...
in a given sample or compound (for instance
natural phenols in a plant extract).
Enol
In organic chemistry, enols are a type of functional group or intermediate in organic chemistry containing a group with the formula (R = many substituents). The term ''enol'' is an abbreviation of ''alkenol'', a portmanteau deriving from "-ene ...
s,
hydroxamic acids
In organic chemistry, hydroxamic acids are a class of organic compounds having a general formula bearing the functional group , where R and R' are typically organyl groups (e.g., alkyl or aryl) or hydrogen. They are amides () wherein the nitroge ...
,
oximes, and
sulfinic acids give positive results as well.
The
bromine test is useful to confirm the result, although modern spectroscopic techniques (e.g.
NMR
Nuclear magnetic resonance (NMR) is a physical phenomenon in which atomic nucleus, nuclei in a strong constant magnetic field are disturbed by a weak oscillating magnetic field (in the near and far field, near field) and respond by producing ...
and
IR spectroscopy
Infrared spectroscopy (IR spectroscopy or vibrational spectroscopy) is the measurement of the interaction of infrared radiation with matter by absorption, emission, or reflection. It is used to study and identify chemical substances or functio ...
) are far superior in determining the identity of the unknown. The quantity of total phenols may be spectroscopically determined by the
Folin–Ciocalteau assay.
Technique
The sample is dissolved in water, or a mixture of water and
ethanol
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
, and a few drops of neutral
ferric chloride
Iron(III) chloride describes the inorganic compounds with the formula (H2O)x. Also called ferric chloride, these compounds are some of the most important and commonplace compounds of iron. They are available both in anhydrous and in hydrated f ...
(FeCl
3) solution, which is prepared by adding de-ionised water. Add sodium hydroxide to the mixture until a permanent brown precipitate is formed. The formation of a red, blue, green, or purple coloration indicates the presence of phenols. Where the sample is insoluble in water, it may be dissolved in
dichloromethane
Dichloromethane (DCM, methylene chloride, or methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with ...
with a small amount of
pyridine
Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weak ...
.
Chemistry
Phenols form a
complex
Complex commonly refers to:
* Complexity, the behaviour of a system whose components interact in multiple ways so possible interactions are difficult to describe
** Complex system, a system composed of many components which may interact with each ...
with
ferric
In chemistry, iron(III) or ''ferric'' refers to the chemical element, element iron in its +3 oxidation number, oxidation state. ''Ferric chloride'' is an alternative name for iron(III) chloride (). The adjective ''ferrous'' is used instead for i ...
ions. This complex has an intense colour, which may vary from blue, green or even red depending upon the nature of the phenol. As an example using the chemical
phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.
The molecule consists of a phenyl group () ...
itself:
: 6 PhOH + Fe
3+ →
6">e(OPh)6sup>3– + 6H
+
Clinical uses
The ferric chloride test can be used to detect metabolites in urine in case of
inborn error of metabolism
Inborn errors of metabolism form a large class of genetic diseases involving congenital disorders of enzyme activities. The majority are due to defects of single genes that code for enzymes that facilitate conversion of various substances (substrat ...
such as
phenylketonuria
Phenylketonuria (PKU) is an inborn error of metabolism that results in decreased metabolism of the amino acid phenylalanine. Untreated PKU can lead to intellectual disability, seizures, behavioral problems, and mental disorders. It may also r ...
. Compounds such as
phenylpyruvate increase in plasma and are excreted out via urine. Also, it can be used to detect
salicylates in urine, quick diagnostic test for
aspirin
Aspirin () is the genericized trademark for acetylsalicylic acid (ASA), a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and inflammation, and as an antithrombotic. Specific inflammatory conditions that aspirin is ...
overdose.
See also
*
Prussian blue assay, a similar test for total phenol determination
References
Chemical tests
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