Clinical data | |
---|---|
Trade names | Ascabin, Ascabiol, Ascarbin, Tenutex, others |
Other names | phenylmethyl ester, benzoic ester |
ATC code | |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.004.003 |
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) |
| |
|
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]
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]
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]
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]
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.
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]
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]
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.
Acrylates are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion CH2=CHCO−2. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acrylates contain vinyl groups. These compounds are of interest because they are bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.
In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.
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.
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.
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.
Tinidazole, sold under the brand name Tindamax among others, is a medication used against protozoan infections. It is widely known throughout Europe and the developing world as a treatment for a variety of anaerobic amoebic and bacterial infections. It was developed in 1972 and is a prominent member of the nitroimidazole antibiotic class.
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.
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.
Cyclohexanecarboxylic acid is the organic compound with the formula C6H11CO2H. It is the carboxylic acid of cyclohexane. It is a colorless oil that crystallizes near room temperature.
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.
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.
2-Nitrobenzaldehyde is an organic compound with the formula O2NC6H4CHO. It is one of three isomers of nitrobenzaldehyde. It contains a nitro group adjacent to the formyl group.
In nitrile reduction a nitrile is reduced to either an amine or an aldehyde with a suitable chemical reagent.
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.
4-Chlorobenzoic acid is an organic compound with the molecular formula ClC6H4CO2H. It is a white solid that is soluble in some organic solvents and in aqueous base. 4-Chlorobenzoic acid is prepared by oxidation of 4-chlorotoluene.