Benzyl benzoate

{{Short description|Chemical compound}} {{Use dmy dates|date=July 2020}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | image = Benzyl benzoate structure.svg | image_class = skin-invert-image | width = | alt = | image2 = Benzyl benzoate ball-and-stick.png | image_class2 = bg-transparent | width2 = | alt2 = | caption =

| pronounce = | tradename = Ascabin, Ascabiol, Ascarbin, Tenutex, others | Drugs.com = | MedlinePlus = | DailyMedID =  | pregnancy_AU =  | pregnancy_AU_comment = | pregnancy_category= | routes_of_administration = | ATC_prefix = P03 | ATC_suffix = AX01 | ATC_supplemental = {{ATCvet|P53|AX11}}

| legal_AU =  | legal_AU_comment = | legal_CA =  | legal_CA_comment = | legal_DE =  | legal_DE_comment = | legal_NZ =  | legal_NZ_comment = | legal_UK =  | legal_UK_comment = | legal_US =  | legal_US_comment = | legal_UN =  | legal_UN_comment = | legal_status =

| IUPAC_name = Benzyl benzoate | C=14 | H=12 | O=2 | SMILES = O=C(OCc1ccccc1)c2ccccc2 | StdInChI = 1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = SESFRYSPDFLNCH-UHFFFAOYSA-N | density = 1.118 | density_notes = | melting_point = 21 | melting_high = | melting_notes = | boiling_point = 323-324 | boiling_notes = | solubility = 0.0153 | specific_rotation = }}

{{Chembox | IUPACName = Benzyl benzoate<ref name="pubchem">{{cite web |last=PubChem |title=Benzyl benzoate |url=https://pubchem.ncbi.nlm.nih.gov/compound/Benzyl-Benzoate |website=pubchem.ncbi.nlm.nih.gov |access-date=2026-03-21}}</ref> | OtherNames = {{ubl|Benzoic acid benzyl ester<ref name="pubchem"></ref>}} | ImageFile =  | ImageSize =  | ImageAlt =  | Section1 = {{Chembox Identifiers | Abbreviations =  | CASNo =  | ChEBI =  | EINECS =  | EC_number =  | InChI =  | KEGG =  | MeSHName =  | PubChem =  | RTECS =  | SMILES =  | UNII = N863NB338G }} | Section2 = {{Chembox Properties  | Appearance = Colorless oily liquid or white solid<ref name="pubchem"></ref> | Odor = Faint, sweet, balsamic<ref name="pubchem"></ref> | BoilingPtC = 323 - 324 | BoilingPt_ref = <ref name="sigmaaldrich"></ref> | Density = 1.118 g/cm<sup>3</sup> at 20 °C<ref name="sigmaaldrich"></ref> | C=14|H=12|O=2 | MeltingPtC = 17 - 20 | MeltingPt_ref = <ref name="sigmaaldrich">{{cite web |last=Sigma-Aldrich |title=Benzyl Benzoate |url=https://www.sigmaaldrich.com/GB/en/sds/sial/b6630 |website=www.sigmaaldrich.com |access-date=2026-03-21}}</ref> | Solubility = 0.0153 g/l at 20 °C<ref name="sigmaaldrich"></ref> | SolubleOther = | VaporPressure = 1.33 hPa at 125 °C<ref name="sigmaaldrich"></ref> }} | Section3 = {{Chembox Structure | Coordination = | CrystalStruct = | MolShape = }} | Section7 = {{Chembox Hazards | AutoignitionPtC = 480 | AutoignitionPt_ref = <ref name="sigmaaldrich"></ref> | ExploLimits = | FlashPtC = 148 | FlashPt_ref = <ref name="sigmaaldrich"></ref> | GHSPictograms = {{GHS07}}{{GHS09}} | GHSSignalWord = Warning | LD50 = | LC50 = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-I = | NFPA-S = | PEL = | REL = | HPhrases = {{H-phrases|H302|H411}} | PPhrases = {{P-phrases|P264|P270|P273|P301+P317|P330|P391|P501}} }} | Section9 = {{Chembox Related | OtherCompounds = Phenyl benzoate }} }}

'''Benzyl benzoate''' is an organic compound which is used as a medication and insect repellent.<ref name=Jr2013/> As a medication it is used to treat scabies and lice.<ref name=WHO2008/> For scabies either permethrin or malathion is typically preferred.<ref name=BNF69>{{cite book|title=British National Formulary: BNF 69|date=2015|publisher=British Medical Association|isbn=978-0-85711-156-2|page=836|edition=69}}</ref> It is applied to the skin as a lotion.<ref name=WHO2008/> Typically two to three applications are needed.<ref name=WHO2008/> It is also present in Balsam of Peru, Tolu balsam, and in a number of flowers.<ref name="frag">{{cite encyclopedia | vauthors = Fahlbusch K, Hammerschmidt F, Panten J, Pickenhagen W, Schatkowski D, Bauer K, Garbe D, Surburg H | date=15 January 2003 | doi=10.1002/14356007.a11_141 | chapter=Flavors and Fragrances | encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry | publisher=Wiley| isbn=3-527-30673-0 }}</ref>

Side effects may include irritation of the skin.<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 978-92-4-154765-9 | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | publisher = World Health Organization | page = 311 }}</ref> It is not recommended in children.<ref name=BNF69/> It is also used in other animals; however, it is considered toxic to cats.<ref name=Jr2013/> How it works is unclear.<ref>{{cite book| vauthors = Bowman DD |title=Georgis' Parasitology for Veterinarians|date=2009|publisher=Elsevier Health Sciences|isbn=978-1-4160-4412-3|page=262|url=https://books.google.com/books?id=g_tBWVBevM0C&pg=PA262|language=en}}</ref>

Benzyl benzoate was first studied medically in 1918.<ref name=Jr2013>{{cite book | veditors = Hayes WJ, Laws ER |title=Handbook of Pesticide Toxicology, Volume 3: Classes of Pesticides|chapter=22.4.2 Benzyl Benzoate|publisher=Academic Press|isbn=0-12-334163-9|pages=1505–1508|year=1991| vauthors = Knowles CO |chapter-url=https://books.google.com/books?id=WiIlBQAAQBAJ&pg=PA1505}}</ref> It is on the World Health Organization's List of Essential Medicines.<ref name="WHO21st">{{cite book | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> Benzyl benzoate is sold under the brand name '''Scabanca''' among others and is available as a generic medication.<ref name=Jr2013/><ref name=BNF69/> It is not available for medical use in the United States.<ref name=Jr2013/>

== Uses ==

=== Medical ===

Benzyl benzoate is an effective and inexpensive topical treatment for human scabies.<ref name="rook">{{citation | vauthors = Burns DA | contribution=Diseases Caused by Arthropods and Other Noxious Animals | veditors = Breathnach SM, Griffiths CE, Cox N, Burns T | title=Rook's Textbook of Dermatology | edition=8th | volume=2 | publisher=Wiley-Blackwell | year=2010 | page=38.41 }}</ref> It has vasodilating and spasmolytic effects and is present in many asthma and whooping cough drugs.<ref name="benzalc">{{cite encyclopedia | vauthors = Brühne F, Wright E | chapter=Benzyl Alcohol | encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry | date=15 June 2000 | doi=10.1002/14356007.a04_001 | publisher=Wiley| isbn=3-527-30673-0 }}</ref> It is also used as an excipient in some testosterone-replacement medications (like Nebido) for treating hypogonadism.<ref name=Nebido>{{cite web |title = Nebido Monograph – Information for Health Care Professionals |url = http://www.nebido.com/en/hcp/product-information/nebido-monograph/index.php |year = 2016 |access-date = 19 October 2016 |publisher = Bayer |archive-url = https://web.archive.org/web/20161019155919/http://www.nebido.com/en/hcp/product-information/nebido-monograph/index.php |archive-date = 19 October 2016}}</ref>

Benzyl benzoate is used as a topical acaricide, scabicide, and pediculicide in veterinary hospitals.<ref name="tox"/>

=== Non-medical ===

Benzyl benzoate is used as a repellent for chiggers, ticks, and mosquitoes.<ref name="tox">{{cite encyclopedia | vauthors = Shaikh J | title=Benzyl Benzoate | veditors = Wexler P | encyclopedia=Encyclopedia of Toxicology | edition=2nd | volume=1 | publisher=Elsevier | year=2005 | pages=264–265 }}</ref> It is also used as a dye carrier, solvent for cellulose derivatives, plasticizer, and fixative in the perfume industry.<ref name="benz">{{cite encyclopedia | vauthors = Maki T, Takeda K | date=15 June 2000 | doi=10.1002/14356007.a03_555 | chapter=Benzoic Acid and Derivatives | encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry | publisher=Wiley| isbn=3-527-30673-0 }}</ref> Its aroma is described as mildly sweet, balsamic, oily, herbal, floral, and fruity.<ref>{{cite web |title=benzyl benzoate|url=https://scentsandflavors.com/database/9dbb4f2d-7784-44fb-b7f9-45abc22ba7d7|website=Scents and Flavors |publisher=Scents and Flavors |access-date=26 March 2026}}</ref>

== Side effects == Benzyl benzoate has low acute toxicity in laboratory animals. It is rapidly hydrolyzed to benzoic acid and benzyl alcohol. Benzyl alcohol is subsequently metabolized to benzoic acid. The conjugates of benzoic acid (hippuric acid and the glucuronide of benzoic acid) are rapidly eliminated in urine.<ref name=Jr2013/> When given in large doses to laboratory animals, benzyl benzoate can cause hyperexcitation, loss of coordination, ataxia, convulsions, and respiratory paralysis.<ref name="tox" />

Benzyl benzoate can be a skin irritant when used as a topical scabicide.<ref name="rook" /> Overdose can result in blistering and hives or a rash can occur as an allergic reaction.<ref>{{cite web|url = https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0009254/?report=details#side_effects|date = 1 October 2016|access-date = 19 October 2016|publisher = PubMed Health at the United States National Library of Medicine|title = Benzyl Benzoate (Topical route)|archive-url = https://web.archive.org/web/20170910234252/https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0009254/?report=details#side_effects|archive-date = 10 September 2017}}</ref><ref>{{cite web|url = http://www.webmd.com/drugs/2/drug-77581/benzocaine-benzyl-benzoate-topical/details/list-sideeffects|title = Benzocaine-Benzyl Benzoate Topical: Side Effects|access-date = 19 October 2016|publisher = WebMD|year = 2016|url-status = live|archive-url = https://web.archive.org/web/20161019160122/http://www.webmd.com/drugs/2/drug-77581/benzocaine-benzyl-benzoate-topical/details/list-sideeffects|archive-date = 19 October 2016}}</ref>

As an excipient in some testosterone-replacement injectable medications, benzyl benzoate has been reported as a cause of anaphylaxis in a case in Australia.<ref>{{cite journal |vauthors=Ong GS, Somerville CP, Jones TW, Walsh JP |year=2012 |title=Anaphylaxis triggered by benzyl benzoate in a preparation of depot testosterone undecanoate |journal=Case Reports in Medicine |publisher=Wiley |publication-date=2012-01-05 |volume=2012 |doi=10.1155/2012/384054 |pmc=3261473 |pmid=22272209 |id=384054 |doi-access=free |article-number=384054}}</ref> 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.<ref name = Nebido /> In Australia, reports to ADRAC, which evaluates reports of adverse drug reactions for the Therapeutic Goods Administration, show several reports of allergic issues since the anaphylaxis case from 2011.

==Chemistry== It is an organic compound with the formula {{chem2|C6H5COOCH2C6H5}}. It is the ester of benzyl alcohol and benzoic acid. It forms either a colorless viscous liquid or white 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 and Tolu balsam.<ref name="benz"/><ref name="frag"/> Its vapor density relative to the air is 7.31.<ref name="sigmaaldrich"></ref>

== Production == Benzyl benzoate is produced industrially by the reaction of sodium benzoate with benzyl chloride in the presence of a base, or by transesterification of methyl benzoate and benzyl alcohol.<ref name="benzalc"/> It is a byproduct of benzoic acid synthesis by toluene oxidation.<ref name="benz" /> It can also be synthesized by the Tishchenko reaction, using benzaldehyde with sodium benzyloxide (generated from sodium and benzyl alcohol) as catalyst:<ref name="benzald">{{cite encyclopedia | vauthors = Brühne F, Wright E | chapter=Benzaldehyde | encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry | date=15 October 2011 | publisher=Wiley | doi=10.1002/14356007.a03_463.pub2| isbn=978-3-527-30673-2 }}</ref><ref name="kamm">{{OrgSynth | vauthors = Kamm O, Kamm WF | title = Benzyl benzoate | collvol = 1 | collvolpages = 104 | year = 1922 | volume = 2 | pages = 5 | doi = 10.15227/orgsyn.002.0005 | prep = cv1p0104}}</ref> :class=skin-invert-image|350px|The Tishchenko reaction: benzaldehyde reacts to benzyl benzoate, the catalyst is sodium benzylate.

== References== {{Reflist}}

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