Benzyl benzoate

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Benzyl benzoate
Benzyl benzoate structure.svg
Benzyl benzoate ball-and-stick.png
Clinical data
Trade names Ascabin, Ascabiol, Ascarbin, Tenutex, others
Other namesphenylmethyl ester, benzoic ester
ATC code
Identifiers
  • Benzyl benzoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.003 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H12O2
Molar mass 212.248 g·mol−1
3D model (JSmol)
Density 1.118 g/cm3 g/cm3
Melting point 18 °C (64 °F)
Boiling point 323 °C (613 °F)
Solubility in water insoluble 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 Yes check.svgY
  • Key:SESFRYSPDFLNCH-UHFFFAOYSA-N

Benzyl benzoate is an organic compound which is used as a medication and insect repellent. [1] As a medication it is used to treat scabies and lice. [2] For scabies either permethrin or malathion is typically preferred. [3] It is applied to the skin as a lotion. [2] Typically two to three applications are needed. [2] It is also present in Balsam of Peru, Tolu balsam, and in a number of flowers. [4]

Contents

Side effects may include irritation of the skin. [2] It is not recommended in children. [3] It is also used in other animals; however, it is considered toxic to cats. [1] How it works is unclear. [5]

Benzyl benzoate was first studied medically in 1918. [1] It is on the World Health Organization's List of Essential Medicines. [6] Benzyl benzoate is sold under the brand name Scabanca among others and is available as a generic medication. [1] [3] It is not available for medical use in the United States. [1]

Uses

Medical

Benzyl benzoate is an effective and inexpensive topical treatment for human scabies. [7] It has vasodilating and spasmolytic effects and is present in many asthma and whooping cough drugs. [8] It is also used as an excipient in some testosterone-replacement medications (like Nebido) for treating hypogonadism. [9]

Benzyl benzoate is used as a topical acaricide, scabicide, and pediculicide in veterinary hospitals. [10]

Non-medical

Benzyl benzoate is used as a repellent for chiggers, ticks, and mosquitoes. [10] It is also used as a dye carrier, solvent for cellulose derivatives, plasticizer, and fixative in the perfume industry. [11]

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. [1] When given in large doses to laboratory animals, benzyl benzoate can cause hyperexcitation, loss of coordination, ataxia, convulsions, and respiratory paralysis. [10]

Benzyl benzoate can be a skin irritant when used as a topical scabicide. [7] Overdose can result in blistering and hives or a rash can occur as an allergic reaction. [12] [13]

As an excipient in some testosterone-replacement injectable medications, benzyl benzoate has been reported as a cause of anaphylaxis in a case in Australia. [14] 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. [9] 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 C6H5CH2O2CC6H5. It is the ester of benzyl alcohol and benzoic acid. 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 and Tolu balsam. [11] [4]

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. [8] It is a byproduct of benzoic acid synthesis by toluene oxidation. [11] It can also be synthesized by the Tishchenko reaction, using benzaldehyde with sodium benzyloxide (generated from sodium and benzyl alcohol) as catalyst: [15] [16]

Tishchenko reaction.svg

Related Research Articles

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Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

<span class="mw-page-title-main">Permethrin</span> Medication and insecticide

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 that touch them.

<span class="mw-page-title-main">Benzyl alcohol</span> Aromatic 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 alcohol is a colorless liquid with a mild pleasant aromatic odor. It is useful as a solvent for its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

<span class="mw-page-title-main">Cinnamic acid</span> Chemical compound

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.

In chemistry, a dehydration reaction is a chemical reaction that involves the loss of water from the reacting molecule or ion. Dehydration reactions are common processes, the reverse of a hydration reaction.

<span class="mw-page-title-main">Benzoyl chloride</span> Organochlorine compound (C7H5ClO)

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring with an acyl chloride substituent. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

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<span class="mw-page-title-main">Chlorobenzene</span> Aromatic organochlorine compound

Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

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 alkoxides are effective catalysts for the reaction.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

<span class="mw-page-title-main">Benzoyl group</span> Chemical group (–C(=O)C₆H₅)

In organic chemistry, benzoyl is the functional group with the formula −COC6H5 and structure −C(=O)−C6H5. It can be viewed as benzaldehyde missing one hydrogen. The benzoyl group has a mass of 105 amu.

Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4]+[NH2CO2]−. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH.

<span class="mw-page-title-main">Benzyl cyanide</span> Chemical compound

Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. It is also an important pheromone in certain species.

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<span class="mw-page-title-main">Ammoxidation</span> Chemical process for producing nitriles from ammonia and oxygen

In organic chemistry, ammoxidation is a process for the production of nitriles using ammonia and oxygen. It is sometimes called the SOHIO process, acknowledging that ammoxidation was developed at Standard Oil of Ohio. The usual substrates are alkenes. Several million tons of acrylonitrile are produced in this way annually:

Dibenzylether is the organic compound with the formula (C6H5CH2)2O. It is classified as an ether derived from benzyl alcohol. A colorless, nearly odorless oil, the compound's main use is as a plasticizer. It is prepared by treating benzyl chloride with base.

In organic chemistry, alkynylation is an addition reaction in which a terminal alkyne is added to a carbonyl group to form an α-alkynyl alcohol.

α,β-Unsaturated carbonyl compound Functional group of organic compounds

α,β-Unsaturated carbonyl compounds are organic compounds with the general structure (O=CR)−Cα=Cβ−R. Such compounds include enones and enals, but also carboxylic acids and the corresponding esters and amides. In these compounds, the carbonyl group is conjugated with an alkene. Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β-carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction.

References

  1. 1 2 3 4 5 6 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   0123341639.
  2. 1 2 3 4 World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 311. hdl:10665/44053. ISBN   9789241547659.
  3. 1 2 3 British National Formulary: BNF 69 (69 ed.). British Medical Association. 2015. p. 836. ISBN   9780857111562.
  4. 1 2 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   3527306730.
  5. ↑ Bowman DD (2009). Georgis' Parasitology for Veterinarians. Elsevier Health Sciences. p. 262. ISBN   978-1416044123.
  6. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. 1 2 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
  8. 1 2 Brühne F, Wright E (15 June 2000). "Benzyl Alcohol". Ullmann's Encyclopedia of Industrial Chemistry . Wiley. doi:10.1002/14356007.a04_001. ISBN   3527306730.
  9. 1 2 "Nebido Monograph – Information for Health Care Professionls". Bayer. 2016. Archived from the original on 19 October 2016. Retrieved 19 October 2016.
  10. 1 2 3 Shaikh J (2005). "Benzyl Benzoate". In Wexler P (ed.). Encyclopedia of Toxicology . Vol. 1 (2nd ed.). Elsevier. pp. 264–265.
  11. 1 2 3 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   3527306730.
  12. ↑ "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.
  13. ↑ "Benzocaine-Benzyl Benzoate Topical: Side Effects". WebMD. 2016. Archived from the original on 19 October 2016. Retrieved 19 October 2016.
  14. ↑ 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. doi: 10.1155/2012/384054 . PMC   3261473 . PMID   22272209. 384054.
  15. ↑ Brühne F, Wright E (15 October 2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry . Wiley. doi:10.1002/14356007.a03_463.pub2. ISBN   978-3527306732.
  16. ↑ Kamm O, Kamm WF (1922). "Benzyl benzoate". Organic Syntheses . 2: 5. doi:10.15227/orgsyn.002.0005 ; Collected Volumes, vol. 1, p. 104.
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