organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The s ...
which is used as a
medication
A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field an ...
and
insect repellent
An insect repellent (also commonly called "bug spray") is a substance applied to skin, clothing, or other surfaces to discourage insects (and arthropods in general) from landing or climbing on that surface. Insect repellents help prevent and co ...
. As a medication it is used to treat
scabies
Scabies (; also sometimes known as the seven-year itch) is a contagious skin infestation by the mite '' Sarcoptes scabiei''. The most common symptoms are severe itchiness and a pimple-like rash. Occasionally, tiny burrows may appear on the skin ...
and
lice
Louse ( : lice) is the common name for any member of the clade Phthiraptera, which contains nearly 5,000 species of wingless parasitic insects. Phthiraptera has variously been recognized as an order, infraorder, or a parvorder, as a resul ...
. For scabies either
permethrin
Permethrin is a medication and an insecticide. As a medication, it is used to treat scabies and lice. It is applied to the skin as a cream or lotion. As an insecticide, it can be sprayed onto clothing or mosquito nets to kill the insects that ...
or
malathion
Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion.
Pesticide use
Malathion is a pesti ...
is typically preferred. It is applied to the skin as a lotion. Typically two to three applications are needed. It is also present in
Balsam of Peru
Balsam of Peru or Peru balsam, also known and marketed by many other names, is a balsam derived from a tree known as '' Myroxylon balsamum'' var. ''pereirae''; it is found in El Salvador, where it is an endemic species.
Balsam of Peru is used ...
,
Tolu balsam
Tolu balsam or balsam of Tolu is a balsam that originates from South America ( Colombia, Peru, Venezuela). It is similar to (and frequently confounded with) the balsam of Peru.
It is tapped from the living trunks of '' Myroxylon balsamum var. ba ...
, and in a number of flowers.
Side effects
In medicine, a side effect is an effect, whether therapeutic or adverse, that is secondary to the one intended; although the term is predominantly employed to describe adverse effects, it can also apply to beneficial, but unintended, consequence ...
may include irritation of the skin. It is not recommended in
children
A child ( : children) is a human being between the stages of birth and puberty, or between the developmental period of infancy and puberty. The legal definition of ''child'' generally refers to a minor, otherwise known as a person younger ...
. It is also used in other animals; however, it is considered toxic to
cats
The cat (''Felis catus'') is a domestic species of small carnivorous mammal. It is the only domesticated species in the family Felidae and is commonly referred to as the domestic cat or house cat to distinguish it from the wild members of ...
. How it works is unclear.
Benzyl benzoate was first studied medically in 1918. It is on the
World Health Organization's List of Essential Medicines
The WHO Model List of Essential Medicines (aka Essential Medicines List or EML), published by the World Health Organization (WHO), contains the medications considered to be most effective and safe to meet the most important needs in a health s ...
. Benzyl benzoate is sold under the brand name Scabanca among others and is available as a
generic medication
A generic drug is a pharmaceutical drug that contains the same chemical substance as a drug that was originally protected by chemical patents. Generic drugs are allowed for sale after the patents on the original drugs expire. Because the active ch ...
. It is not available for medical use in the
United States
The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territo ...
.
Uses
Medical
Benzyl benzoate is an effective and inexpensive topical treatment for human
scabies
Scabies (; also sometimes known as the seven-year itch) is a contagious skin infestation by the mite '' Sarcoptes scabiei''. The most common symptoms are severe itchiness and a pimple-like rash. Occasionally, tiny burrows may appear on the skin ...
asthma
Asthma is a long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wheezing, ...
and
whooping cough
Whooping cough, also known as pertussis or the 100-day cough, is a highly contagious bacterial disease. Initial symptoms are usually similar to those of the common cold with a runny nose, fever, and mild cough, but these are followed by two or ...
drugs. It is also used as an
excipient
An excipient is a substance formulated alongside the active ingredient of a medication, included for the purpose of long-term stabilization, bulking up solid formulations that contain potent active ingredients in small amounts (thus often referred ...
in some
testosterone
Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristi ...
-replacement medications (like Nebido) for treating
hypogonadism
Hypogonadism means diminished functional activity of the gonads—the testes or the ovaries—that may result in diminished production of sex hormones. Low androgen (e.g., testosterone) levels are referred to as hypoandrogenism and low estroge ...
.
Benzyl benzoate is used as a topical
acaricide
Acaricides are pesticides that kill members of the arachnid subclass '' Acari'', which includes ticks and mites.
Acaricides are used both in medicine and agriculture, although the desired selective toxicity differs between the two fields.
Termin ...
Benzyl benzoate is used as a repellent for chiggers, ticks, and mosquitoes. It is also used as a dye carrier, solvent for cellulose derivatives, plasticizer, and fixative in the perfume industry.
Side effects
Benzyl benzoate has low acute toxicity in laboratory animals. It is rapidly
hydrolyzed
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolysis ...
to
benzoic acid
Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, ...
and
benzyl alcohol
Benzyl alcohol is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid ...
. Benzyl alcohol is subsequently metabolized to benzoic acid. The conjugates of benzoic acid (
hippuric acid
Hippuric acid ( Gr. ''hippos'', horse, ''ouron'', urine) is a carboxylic acid and organic compound. It is found in urine and is formed from the combination of benzoic acid and glycine. Levels of hippuric acid rise with the consumption of phenoli ...
and the
glucuronide
A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. The glucuronides belong to the glycosides.
Glucuronidation, the conversion of chemical compounds to glucur ...
of benzoic acid) are rapidly eliminated in urine. When given in large doses to laboratory animals, benzyl benzoate can cause hyperexcitation, loss of coordination,
ataxia
Ataxia is a neurological sign consisting of lack of voluntary coordination of muscle movements that can include gait abnormality, speech changes, and abnormalities in eye movements. Ataxia is a clinical manifestation indicating dysfunction of ...
,
convulsion
A convulsion is a medical condition where the body muscles contract and relax rapidly and repeatedly, resulting in uncontrolled shaking. Because epileptic seizures typically include convulsions, the term ''convulsion'' is sometimes used as a s ...
s, and respiratory paralysis.
Benzyl benzoate can be a skin irritant when used as a topical scabicide. Overdose can result in blistering and hives or a rash can occur as an allergic reaction.
As an excipient in some testosterone-replacement injectable medications, benzyl benzoate has been reported as a cause of
anaphylaxis
Anaphylaxis is a serious, potentially fatal allergic reaction and medical emergency that is rapid in onset and requires immediate medical attention regardless of use of emergency medication on site. It typically causes more than one of the foll ...
in a case in Australia. Bayer includes this report in information for health professionals and recommends that physicians "should be aware of the potential for serious allergic reactions" to preparations of this type. In Australia, reports to ADRAC, which evaluates reports of
adverse drug reactions
An adverse drug reaction (ADR) is a harmful, unintended result caused by taking medication. ADRs may occur following a single dose or prolonged administration of a drug or result from the combination of two or more drugs. The meaning of this term ...
for the
Therapeutic Goods Administration
The Therapeutic Goods Administration (TGA) is the medicine and therapeutic regulatory agency of the Australian Government. As part of the Department of Health and Aged Care, the TGA regulates the quality, supply and advertising of medicines, ...
, show several reports of allergic issues since the anaphylaxis case from 2011.
Chemistry
It is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The s ...
with the formula C6H5CH2O2CC6H5. It is the
ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glyceride ...
of
benzyl alcohol
Benzyl alcohol is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid ...
and
benzoic acid
Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, ...
. It forms either a viscous liquid or solid flakes and has a weak, sweet-balsamic odor. It occurs in a number of blossoms (e. g. tuberose, hyacinth) and is a component of
Balsam of Peru
Balsam of Peru or Peru balsam, also known and marketed by many other names, is a balsam derived from a tree known as '' Myroxylon balsamum'' var. ''pereirae''; it is found in El Salvador, where it is an endemic species.
Balsam of Peru is used ...
and
Tolu balsam
Tolu balsam or balsam of Tolu is a balsam that originates from South America ( Colombia, Peru, Venezuela). It is similar to (and frequently confounded with) the balsam of Peru.
It is tapped from the living trunks of '' Myroxylon balsamum var. ba ...
.
Production
Benzyl benzoate is produced industrially by the reaction of
sodium benzoate
Sodium benzoate is the sodium salt of benzoic acid, widely used as a food preservative (with an E number of E211) and a pickling agent. It appears as a white crystalline chemical with the formula C6H5COONa.
Production
Sodium benzoate is com ...
with benzyl chloride in the presence of a base, or by
transesterification
In organic chemistry, transesterification is the process of exchanging the organic group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. The reaction can ...
of methyl benzoate and benzyl alcohol. It is a byproduct of benzoic acid synthesis by
toluene
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) ...
oxidation. It can also be synthesized by the
Tishchenko reaction The Tishchenko reaction is an organic chemical reaction that involves disproportionation of an aldehyde in the presence of an alkoxide. The reaction is named after Russian organic chemist Vyacheslav Tishchenko, who discovered that aluminium a ...
, using
benzaldehyde
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful.
It is a colorless liquid with a characteristic almond-like od ...
with sodium benzyloxide (generated from
sodium
Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable ...
and benzyl alcohol) as
catalyst
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recy ...