Benzyl benzoate is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

which is used as a

medication Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to medical diagnosis, diagnose, cure, treat, or preventive medicine, prevent disease. Drug therapy (pharmaco ...

and

insect repellent An insect repellent (also commonly called "bug spray" or "bug deterrent") is a substance applied to the skin, clothing, or other surfaces to discourage insects (and arthropods in general) from landing or climbing on that surface. Insect repellent ...

. As a medication it is used to treat

scabies Scabies (; also sometimes known as the seven-year itch) is a contagious human skin infestation by the tiny (0.2–0.45 mm) mite ''Sarcoptes scabiei'', variety ''hominis''. The word is from . The most common symptoms are severe itchiness a ...

and

lice Louse (: lice) is the common name for any member of the infraorder Phthiraptera, which contains nearly 5,000 species of wingless parasitic insects. Phthiraptera was previously recognized as an order, until a 2021 genetic study determined th ...

. 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 outer clothing or mosquito nets to kill the insects ...

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. The compound's name is presumably ...

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 is the resinous exudate (or sap) which forms on certain kinds of trees and shrubs. Balsam (from Latin ''balsamum'' "gum of the balsam tree," ultimately from a Semitic source such as ) owes its name to the biblical Balm of Gilead. Chem ...

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. b ...

, and in a number of flowers.

Side effects In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually used ...

may include irritation of the skin. It is not recommended in

children A child () is a human being between the stages of childbirth, birth and puberty, or between the Development of the human body, developmental period of infancy and puberty. The term may also refer to an unborn human being. In English-speaking ...

. It is also used in other animals; however, it is considered toxic to

cats The cat (''Felis catus''), also referred to as the domestic cat or house cat, is a small domesticated carnivorous mammal. It is the only domesticated species of the family Felidae. Advances in archaeology and genetics have shown that the ...

. 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 (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

Uses

Medical

Benzyl benzoate is an effective and inexpensive topical treatment for human

. It has vasodilating and

spasmolytic Spasmolytic may refer to: * Antispasmodic, smooth muscle relaxant * A type of muscle relaxant A muscle relaxant is a drug that affects skeletal muscle function and decreases the muscle tone. It may be used to alleviate symptoms such as muscle spa ...

effects and is present in many

asthma Asthma is a common 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 wh ...

and

whooping cough Whooping cough ( or ), also known as pertussis or the 100-day cough, is a highly contagious, Vaccine-preventable diseases, vaccine-preventable Pathogenic bacteria, bacterial disease. Initial symptoms are usually similar to those of the common c ...

drugs. It is also used as an

excipient An excipient is a substance formulated alongside the active ingredient of a medication. They may be used to enhance the active ingredient’s therapeutic properties; to facilitate drug absorption; to reduce viscosity; to enhance solubility; to i ...

in some

testosterone Testosterone is the primary male sex hormone and androgen in Male, males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testicles and prostate, as well as promoting se ...

-replacement medications (like Nebido) for treating

hypogonadism Hypogonadism means diminished functional activity of the human gonad, gonads—the testicles or the ovary, ovaries—that may result in diminished biosynthesis, production of sex hormones. Low androgen (e.g., testosterone) levels are referred t ...

. 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. Termi ...

scabicide Scabies (; also sometimes known as the seven-year itch) is a contagious human skin infestation by the tiny (0.2–0.45 mm) mite ''Sarcoptes scabiei'', variety ''hominis''. The word is from . The most common symptoms are severe itchiness a ...

, and

pediculicide The treatment of human lice is the removal of head lice parasites from human hair. It has been debated and studied for centuries. However, the number of cases of human louse infestations (or pediculosis) has increased worldwide since the mid-1960s ...

in veterinary hospitals.

Non-medical

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 hydrolysi ...

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. The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn," which ...

and

benzyl alcohol Benzyl alcohol (also known as α-cresol) 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 a ...

. Benzyl alcohol is subsequently metabolized to benzoic acid. The conjugates of benzoic acid (

hippuric acid Hippuric acid (Greek language, 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 consumpt ...

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 glucu ...

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 (from Greek α- negative prefix+ -τάξις rder= "lack of order") is a neurological sign consisting of lack of voluntary coordination of muscle movements that can include gait abnormality, speech changes, and abnormalities in e ...

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 often used as a synony ...

s, and

respiratory paralysis Respiratory failure results from inadequate gas exchange by the respiratory system, meaning that the arterial oxygen, carbon dioxide, or both cannot be kept at normal levels. A drop in the oxygen carried in the blood is known as hypoxemia; a ris ...

. 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 (Greek: 'up' + 'guarding') is a serious, potentially fatal allergic reaction and medical emergency that is rapid in onset and requires immediate medical attention regardless of the use of emergency medication on site. It typicall ...

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 may result from the combination of two or more drugs. The meaning of this ...

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, Disability and Ageing, the TGA regulates the safety, quality, efficacy and advertisi ...

, show several reports of allergic issues since the anaphylaxis case from 2011.

Chemistry

It is an

with the formula C₆H₅CH₂O₂CC₆H₅. It is the

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

and

. 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 ''Agave amica'', formerly ''Polianthes tuberosa'', the tuberose, is a perennial plant in the family Asparagaceae, subfamily Agavoideae, extracts of which are used as a Note (perfumery), note in perfumery. Now widely grown as an ornamental plant, ...

hyacinth ''Hyacinthus'' is a genus of bulbous herbs, and spring-blooming Perennial plant, perennials. They are fragrant flowering plants in the family Asparagaceae, subfamily Scilloideae and are commonly called hyacinths (). The genus is native predomin ...

) and is a component of

and

Production

Benzyl benzoate is produced industrially by the reaction of

sodium benzoate Sodium benzoate also known as benzoate of soda 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. Pro ...

with benzyl chloride in the presence of a base, or by

transesterification Transesterification is the process of exchanging the organic functional 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. Strong acids catalyze the r ...

methyl benzoate Methyl benzoate is an organic compound. It is an ester with the chemical formula , sometimes abbreviated as , where Ph and Me are phenyl and methyl, respectively. Its structure is . It is a colorless liquid that is poorly soluble in water, but m ...

and benzyl alcohol. It is a byproduct of benzoic acid synthesis by

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...

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 alk ...

, using

benzaldehyde Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful. It is a colorless liquid with a characteristic almond-li ...

with sodium benzyloxide (generated from

sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

and benzyl alcohol) as

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

: :

References

{{DEFAULTSORT:Benzyl Benzoate Benzoate esters Ester solvents Insecticides Plasticizers Perfume ingredients World Health Organization essential medicines Wikipedia medicine articles ready to translate Benzyl esters