ChemicalBook > Product Catalog > API > Synthetic Anti-infective Drugs > Antiseptics & Disinfectants Drugs > Benzyl benzoate
Basic information Description Chemical Properties Uses Preparation toxicity References Safety Related Supplier
Benzyl benzoate Chemical Properties
- Melting point:17-20 °C (lit.)
- Boiling point:323-324 °C (lit.)
- Density 1.118 g/mL at 20 °C (lit.)
- vapor pressure 1 mm Hg ( 125 °C)
- refractive index n
- FEMA 2138 | BENZYL BENZOATE
- FEMA 2797 | OCTANAL
- Flash point:298 °F
- storage temp. 2-8°C
- solubility Miscible with ethanol, alcohol, chloroform, ether, oils.
- form Liquid
- color Clear colorless
- Water Solubility practically insoluble
- Merck 14,1127
- JECFA Number24
- BRN 2049280
- Stability:Stable. Substances to be avoided include strong oxidizing agents. Combustible.
- CAS DataBase Reference120-51-4(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzyl Benzoate(120-51-4)
- EPA Substance Registry SystemBenzyl benzoate (120-51-4)
- Hazard Codes Xn,N
- Risk Statements 22-51/53
- Safety Statements 25-61-46
- RIDADR UN 3082 9 / PGIII
- WGK Germany 2
- RTECS DG4200000
- Autoignition Temperature896 °F
- TSCA Yes
- HazardClass 9
- HS Code 29163100
- Hazardous Substances Data120-51-4(Hazardous Substances Data)
- ToxicityLD50 in rats, mice, rabbits, guinea pigs (g/kg): 1.7, 1.4, 1.8, 1.0 orally (Draize)
Benzyl benzoate Usage And Synthesis
- DescriptionBenzyl benzoate (BnBzO) is a mediation and insect repellent. It is one of the older preparation used to treat scabies which is a skin infections caused by the mite scarcoptes scabiei since it is lethal to the mite. It is capable of killing the mite in 5 minutes. It can also be used for the treatment of lice infestation of the head and the body. Its mechanism of action is through exerting toxic effect on the nervous system of the insects, further causing its death. It is also toxic to mite ova through an unknown mechanism. It can also be used as a repellent for chiggers, ticks, and mosquitoes as well as a dye carrier, solvent of cellulose derivatives, plasticizer, and a fixative.
- Chemical PropertiesBenzyl benzoate is a clear, colorless, oily liquid with a light, balsamic odor reminiscent of almond and a sharp, pungent taste. It produces a sharp, burning sensation on the tongue. At temperatures below 178℃ it exists as clear, colorless crystals.
- UsesBenzyl Benzoate has seen use as an insecticide, as well as a solvent for various chemical reactions.
Benzyl benzoate is a benzyl compound that can be synthesized by reacting benzyl chloride with sodium benzoate in the presence of tetrabutylaramonium iodide. It has been used to:
Prepare benzyl alcohol/benzyl benzoate (BABB) solution employed for enhancing the tissue transparency during the whole-mount immunostaining BABB method.
Study its ability to induce an olfactory response in the third instar larvae of Drosophila melanogaster.
Prepare Spalteholz fluid in combination with methyl salicylate, employed during LSFM (light sheet fluorescence microscopy) imaging.
- PreparationBenzyl benzoate is a constituent of Peru balsam and occurs naturally in certain plant species. Commercially, benzyl benzoate is produced synthetically by the dry esterification of sodium benzoate and benzoyl chloride in the presence of triethylamine or by the reaction of sodium benzylate with benzaldehyde.
- toxicityIn man, benzyl benzoate was a skin sensitizer and caused gastro-intestinal effects in an infant. It was of moderate to low acute oral toxicity in a range of laboratory animal species and of low acute dermal toxicity in rabbits. Central nervous system effects were induced in several species given single doses orally or dermally. Repeated skin applications caused degenerative changes in various organs (including the liver, spleen and testes) of rabbits. No effects were seen in reproductive studies involving repeated oral administration to rats during pregnancy and lactation. Benzyl benzoate gave no evidence of mutagenicity in an Ames bacterial assay. It was a mild skin irritant in rabbits.
- DescriptionBenzyl benzoate is the ester of benzyl alcohol and benzoic acid, with the formula C6H5CH2O2CC6H5. This easily prepared compound with a mild balsamic odor has a variety of uses.
- Chemical PropertiesBenzyl Benzoate is the main component of Peru balsam oil. It occurs in fairly large amounts in a number of blossom concretes and absolutes (e.g., tuberose and hyacinth). It forms either a viscous liquid or solid flakes (mp 21–22°C) and has a weak, sweet, balsamic odor.
Benzyl Benzoate is prepared either by transesterification of technical methyl benzoate with benzyl alcohol or from benzyl chloride and sodium benzoate. A third process starts with benzaldehyde, which is converted in high yield into benzyl benzoate in the presence of sodium or aluminum benzylate (Tishchenko reaction). Benzyl benzoate is used in perfumery as a fixative and as a modifier in heavy blossom fragrances.
- OccurrenceContained in Peru balsam and in the concrete and absolute of tuberose flowers, hyacinth, Narcissus jonquilla L., and Dianthus caryophillus L.; also in the oil of ylang-ylang and in Tolu balsam. Reported found in American cranberry, cinnamon bark, cassia leaf, corn oil and hog plum (Spondias mombins L.).
- UsesBenzyl benzoate, as a topical solution, may be used as an antiparasitic insecticide to kill the mites responsible for the skin condition scabies , for example as a combination drug of benzyl benzoate/disulfiram.
It has other uses :
a fixative in fragrances to improve the stability and other characteristics of the main ingredients
a food additive in artificial flavors
a plasticizer in cellulose and other polymers
a solvent for various chemical reactions
a treatment for sweet itch in horses
a treatment for scaly leg mites in chickens.
- Usesbenzyl benzoate is an anti-microbial. It can also act as a solvent, helping dissolve other substances in the product, and as a perfuming ingredient. It is the ester of benzyl alcohol and benzoic acid.
- UsesAs solvent of cellulose acetate, nitrocellulose and artificial musk; substitute for camphor in celluloid and plastic pyroxylin Compounds; perfume fixative; in confectionery and chewing gum flavors.
- PreparationBy the dry esterification of sodium benzoate and benzoyl chloride in the presence of triethylamine or by reaction of sodium benzylate on benzaldehyde.
- Production MethodsBENZYL BENZOATE is produced by the Cannizzaro reaction from benzaldehyde, by esterifying benzyl alcohol with benzoic acid, or by treating sodium benzoate with benzyl chloride. It is purified by distillation and crystallization. Benzyl benzoate is used as a fixative and solvent for musk in perfumes and flavors, as a plasticizer, miticide, and in some external medications. The compound has been found effective in the treatment of scabies and pediculosis capitis (head lice, Pediculus humanus var. capitis).
- IndicationsBenzyl benzoate: 20% to 25%. This agent is relatively nontoxic and is widely
used in developing countries to treat scabies and pediculosis capitis and pubis.
Only a veterinary preparation is available in the United States. Benzyl benzoate is
synthetically derived from the esterification of benzoic acid with benzyl alcohol. Its
mechanism of action is unknown. It is toxic to Sarcoptes scabei and may be toxic
to Pediculosis capitis and Phthirus pubis. No resistance has been demonstrated
Benzyl benzoate can be used in a 5% emulsion to repel many arthropods and can be used as a lotion to treat sarcoptic mange and canine pediculosis.
- brand namePharmaceutic necessity for Dimercaprol [Injection]. Benylate (Sterling Winthrop).
- Taste threshold valuesTaste characteristics at 30 ppm: balsamic, fruity with powdery and berry nuances.
- Synthesis Reference(s)Journal of Heterocyclic Chemistry, 24, p. 187, 1987 DOI: 10.1002/jhet.5570240135
Tetrahedron Letters, 27, p. 2383, 1986 DOI: 10.1016/S0040-4039(00)84535-9
- HazardIrritant to eyes, skin.
- Pharmaceutical ApplicationsBenzyl benzoate is used as a solubilizing agent and nonaqueous
solvent in intramuscular injections at concentrations of
0.01–46.0% v/v, and as a solvent and plasticizer for cellulose
and nitrocellulose. It is also used in the preparation of spray-dried
powders using nanocapsules.
However, the most widespread pharmaceutical use of benzyl benzoate is as a topical therapeutic agent in the treatment of scabies. Benzyl benzoate is also used therapeutically as a parasiticide in veterinary medicine.
Other applications of benzyl benzoate include its use as a pediculicide, and as a solvent and fixative for flavors and perfumes in cosmetics and food products.
- Contact allergensBenzyl benzoate is the ester of benzyl alcohol and benzoic acid. It is contained in Myroxylon pereirae and Tolu balsam. It is used in acaricide preparations against Sarcoptes scabiei or as a pediculicide. Direct contact may cause skin irritation, but rarely allergic contact dermatitis. As a fragrance allergen, benzyl benzoate has to be mentioned by name in EU cosmetics.
- Clinical UseBenzyl benzoate is a naturally occurring ester obtained fromPeru balsam and other resins. It is also prepared syntheticallyfrom benzyl alcohol and benzoyl chloride. The ester isa clear colorless liquid with a faint aromatic odor. It is insolublein water but soluble in organic solvents.
Benzyl benzoate is an effective scabicide when appliedtopically. Immediate relief from itching probably resultsfrom a local anesthetic effect; however, a complete cureis frequently achieved with a single application of a 25%emulsion of benzyl benzoate in oleic acid, stabilized withtriethanolamine. This preparation has the additionaladvantage of being essentially odorless, nonstaining, andnonirritating to the skin. It is applied topically as a lotionover the entire dampened body, except the face.
- SafetyBenzyl benzoate is metabolized by rapid hydrolysis to benzoic acid
and benzyl alcohol. Benzyl alcohol is then further metabolized to
hippuric acid, which is excreted in the urine.
Benzyl benzoate is widely used as a 25% v/v topical application in the treatment of scabies and as an excipient in intramuscular injections and oral products. Adverse reactions to benzyl benzoate include skin irritation and hypersensitivity reactions. Oral ingestion may cause harmful stimulation of the CNS and convulsions. Benzyl benzoate should be avoided by perople with perfume allergy.
LD50 (cat, oral): 2.24 g/kg
LD50 (dog, oral): 22.44 g/kg
LD50 (guinea pig, oral): 1.0 g/kg
LD50 (mouse, oral): 1.4 g/kg
LD50 (rabbit, oral): 1.68 g/kg
LD50 (rabbit, skin): 4.0 g/kg
LD50 (rat, oral): 0.5 g/kg
LD50 (rat, skin): 4.0 g/kg
- Chemical SynthesisThis colorless liquid is formally the condensation product of benzoic acid and benzyl alcohol. It can also be generated from benzaldehyde by the Tishchenko reaction.
- Environmental FateBenzyl benzoate acts as a local irritant. At high levels of exposure, free benzoic acid may sequester significant amounts of acetyl coenzyme A (CoA), which could disrupt cholinergic signaling. Recent findings suggest that benzyl benzoate may have estrogenic properties.
- MetabolismBenzyl benzoate, a relatively non-toxic liquid widely used for the treatment of scabies, is converted into benzoic acid in vivo (Williams, 1959).
- storageBenzyl benzoate is stable when stored in tight, well-filled, lightresistant containers. Exposure to excessive heat (above 408℃) should be avoided.
- Toxicity evaluationAcute oral LD50 for rats: 1,700 mg/kg
- IncompatibilitiesBenzyl benzoate is incompatible with alkalis and oxidizing agents.
- Regulatory StatusIncluded in the FDA Inactive Ingredients Database (IM injections and oral capsules). Included, as an active ingredient, in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Benzyl benzoate Preparation Products And Raw materials
- methyl 2-amino-5-[4-amino-3-(methoxycarbonyl)benzyl]benzoate BENZYL BENZOATE-D12 BENZYL BENZOATE SOLUTION 5000UG/ML IN HEXANE 5X1ML BENZYL BENZOATE SOLUTION 2000UG/ML IN HEXANE 5ML BENZYL BENZOATE SOLUTION 5000UG/ML IN HEXANE 1ML BENZYL BENZOATE SOLUTION 5000UG/ML IN HEXANE 5ML Benexate Hydrochloride BENZOICACID Polyol benzoate Benzyl AQUANTRAAL Benzyl formate Carbobenzoxyhydrazide BUTYL OLEATE Benzyl nicotinate Benzyl isocyanate Denatonium Benzoate Anhydrous TRIS(TRIMETHYLSILYL) PHOSPHATE
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