Benzyl benzoate

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Benzyl benzoate
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Clinical data
Trade namesAscabin, Ascabiol, Ascarbin, Tenutex, others
Other namesBenzoic acid benzyl ester
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Identifiers
  • Benzyl benzoate
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Chemical and physical data
FormulaC14H12O2
Molar mass212.248 g·mol−1
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Density1.118 g/cm3
Melting point21 °C (70 °F)
Boiling point323–324 °C (613–615 °F)
Solubility in water0.0153 mg/mL (20 °C)
  • O=C(OCc1ccccc1)c2ccccc2
  • InChI=1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2 checkY
  • Key:SESFRYSPDFLNCH-UHFFFAOYSA-N
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Benzyl benzoate
Names
IUPAC name
Benzyl benzoate[1]
Other names
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  • Benzoic acid benzyl ester[1]
Identifiers
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Properties
C14H12O2
Molar mass 212.248 g·mol−1
Appearance Colorless oily liquid or white solid[1]
Odor Faint, sweet, balsamic[1]
Density 1.118 g/cm3 at 20 °C[2]
Melting point 17–20 °C (63–68 °F; 290–293 K)[2]
Boiling point 323–324 °C (613–615 °F; 596–597 K)[2]
0.0153 g/l at 20 °C[2]
Vapor pressure 1.33 hPa at 125 °C[2]
Hazards
Flash point 148 °C (298 °F; 421 K)[2]
480 °C (896 °F; 753 K)[2]
Related compounds
Related compounds
 Phenyl benzoate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Benzyl benzoate is an organic compound which is used as a medication and insect repellent.[3] As a medication it is used to treat scabies and lice.[4] For scabies either permethrin or malathion is typically preferred.[5] It is applied to the skin as a lotion.[4] Typically two to three applications are needed.[4] It is also present in Balsam of Peru, Tolu balsam, and in a number of flowers.[6]

Side effects may include irritation of the skin.[4] It is not recommended in children.[5] It is also used in other animals; however, it is considered toxic to cats.[3] How it works is unclear.[7]

Benzyl benzoate was first studied medically in 1918.[3] It is on the World Health Organization's List of Essential Medicines.[8] Benzyl benzoate is sold under the brand name Scabanca among others and is available as a generic medication.[3][5] It is not available for medical use in the United States.[3]

Uses

Medical

Benzyl benzoate is an effective and inexpensive topical treatment for human scabies.[9] It has vasodilating and spasmolytic effects and is present in many asthma and whooping cough drugs.[10] It is also used as an excipient in some testosterone-replacement medications (like Nebido) for treating hypogonadism.[11]

Benzyl benzoate is used as a topical acaricide, scabicide, and pediculicide in veterinary hospitals.[12]

Non-medical

Benzyl benzoate is used as a repellent for chiggers, ticks, and mosquitoes.[12] It is also used as a dye carrier, solvent for cellulose derivatives, plasticizer, and fixative in the perfume industry.[13] Its aroma is described as mildly sweet, balsamic, oily, herbal, floral, and fruity.[14]

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.[3] When given in large doses to laboratory animals, benzyl benzoate can cause hyperexcitation, loss of coordination, ataxia, convulsions, and respiratory paralysis.[12]

Benzyl benzoate can be a skin irritant when used as a topical scabicide.[9] Overdose can result in blistering and hives or a rash can occur as an allergic reaction.[15][16]

As an excipient in some testosterone-replacement injectable medications, benzyl benzoate has been reported as a cause of anaphylaxis in a case in Australia.[17] 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.[11] 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 Page Module:Chem2/styles.css has no content.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.[13][6] Its vapor density relative to the air is 7.31.[2]

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.[10] It is a byproduct of benzoic acid synthesis by toluene oxidation.[13] It can also be synthesized by the Tishchenko reaction, using benzaldehyde with sodium benzyloxide (generated from sodium and benzyl alcohol) as catalyst:[18][19]

The Tishchenko reaction: benzaldehyde reacts to benzyl benzoate, the catalyst is sodium benzylate.

References

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  1. ^ a b c d Page Module:Citation/CS1/styles.css has no content.PubChem. "Benzyl benzoate". pubchem.ncbi.nlm.nih.gov. Retrieved 21 March 2026.
  2. ^ a b c d e f g h Page Module:Citation/CS1/styles.css has no content.Sigma-Aldrich. "Benzyl Benzoate". www.sigmaaldrich.com. Retrieved 21 March 2026.
  3. ^ a b c d e f Page Module:Citation/CS1/styles.css has no content.Knowles CO (1991). "22.4.2 Benzyl Benzoate". In Hayes WJ, Laws ER (eds.). Handbook of Pesticide Toxicology, Volume 3: Classes of Pesticides. Academic Press. pp. 1505–1508. ISBN 0-12-334163-9.
  4. ^ a b c d Page Module:Citation/CS1/styles.css has no content.Stuart MC, Kouimtzi M, Hill SR, eds. (2009). WHO Model Formulary 2008. World Health Organization. p. 311. hdl:10665/44053. ISBN 978-92-4-154765-9.
  5. ^ a b c Page Module:Citation/CS1/styles.css has no content.British National Formulary: BNF 69 (69 ed.). British Medical Association. 2015. p. 836. ISBN 978-0-85711-156-2.
  6. ^ a b Page Module:Citation/CS1/styles.css has no content.Fahlbusch K, Hammerschmidt F, Panten J, Pickenhagen W, Schatkowski D, Bauer K, et al. (15 January 2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. Wiley. doi:10.1002/14356007.a11_141. ISBN 3-527-30673-0.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Bowman DD (2009). Georgis' Parasitology for Veterinarians. Elsevier Health Sciences. p. 262. ISBN 978-1-4160-4412-3.
  8. ^ Page Module:Citation/CS1/styles.css has no content.World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ^ a b Page Module:Citation/CS1/styles.css has no content.Burns DA (2010), "Diseases Caused by Arthropods and Other Noxious Animals", in Breathnach SM, Griffiths CE, Cox N, Burns T (eds.), Rook's Textbook of Dermatology, vol. 2 (8th ed.), Wiley-Blackwell, p. 38.41
  10. ^ a b Page Module:Citation/CS1/styles.css has no content.Brühne F, Wright E (15 June 2000). "Benzyl Alcohol". Ullmann's Encyclopedia of Industrial Chemistry. Wiley. doi:10.1002/14356007.a04_001. ISBN 3-527-30673-0.
  11. ^ a b Page Module:Citation/CS1/styles.css has no content."Nebido Monograph – Information for Health Care Professionals". Bayer. 2016. Archived from the original on 19 October 2016. Retrieved 19 October 2016.
  12. ^ a b c Page Module:Citation/CS1/styles.css has no content.Shaikh J (2005). "Benzyl Benzoate". In Wexler P (ed.). Encyclopedia of Toxicology. Vol. 1 (2nd ed.). Elsevier. pp. 264–265.
  13. ^ a b c Page Module:Citation/CS1/styles.css has no content.Maki T, Takeda K (15 June 2000). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Wiley. doi:10.1002/14356007.a03_555. ISBN 3-527-30673-0.
  14. ^ Page Module:Citation/CS1/styles.css has no content."benzyl benzoate". Scents and Flavors. Scents and Flavors. Retrieved 26 March 2026.
  15. ^ Page Module:Citation/CS1/styles.css has no content."Benzyl Benzoate (Topical route)". PubMed Health at the United States National Library of Medicine. 1 October 2016. Archived from the original on 10 September 2017. Retrieved 19 October 2016.
  16. ^ Page Module:Citation/CS1/styles.css has no content."Benzocaine-Benzyl Benzoate Topical: Side Effects". WebMD. 2016. Archived from the original on 19 October 2016. Retrieved 19 October 2016.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Ong GS, Somerville CP, Jones TW, Walsh JP (2012). "Anaphylaxis triggered by benzyl benzoate in a preparation of depot testosterone undecanoate". Case Reports in Medicine. 2012 384054. Wiley (published 5 January 2012). doi:10.1155/2012/384054. PMC 3261473. PMID 22272209. 384054.
  18. ^ Page Module:Citation/CS1/styles.css has no content.Brühne F, Wright E (15 October 2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Wiley. doi:10.1002/14356007.a03_463.pub2. ISBN 978-3-527-30673-2.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Kamm O, Kamm WF (1922). "Benzyl benzoate". Organic Syntheses. 2: 5. doi:10.15227/orgsyn.002.0005; Page Module:Citation/CS1/styles.css has no content.Collected Volumes, vol. 1, p. 104.

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