BENZYL BENZOATE

CAS NO:120-51-4
EC NO:204-402-9 

SYNONYMS

BENZYL BENZOATE;120-51-4;Ascabiol;Benzoic acid, phenylmethyl ester;Benylate;Novoscabin;Benzoic acid benzyl ester;Benzoic acid, benzyl ester;Ascabin;Scabitox;Scobenol;Benzyl phenylformate;Phenylmethyl benzoate;Benzylets;Colebenz;Peruscabin;Scabagen;Scabanca;Scabiozon;Vanzoate;Scabide;benzylbenzoate;Benzyl benzenecarboxylate;Antiscabiosum;Benzyl alcohol benzoic ester;Peruscabina;Spasmodin;Venzonate;Benzylis benzoas;Benzylum benzoicum;Benzylester kyseliny benzoove;Benzoesaeurebenzylester;BENZOIC ACID PHENYLMETHYLESTER;Caswell No. 082;Benzylbenzenecarboxylate;FEMA Number 2138;Benzyl benzoate (natural);NSC 8081;UNII-N863NB338G;FEMA No. 2138;HSDB 208;EINECS 204-402-9;Benzylester kyseliny benzoove [Czech];EPA Pesticide Chemical Code 009501;BRN 2049280;CHEMBL1239;AI3-00523;CHEBI:41237;N863NB338G;MFCD00003075;NCGC00094981-03;Benzyl benzoate, 99+%;DSSTox_CID_9153;DSSTox_RID_78686;DSSTox_GSID_29153;Venzoate;Benzyl benzoate, analytical standard;BZM;CAS-120-51-4;SMR000471875;benzylbenzoat;Benzyl benzoate [USP:JAN];Acarobnzyl;Benzevan;Bengal;Benzyl benzoate [USAN:JAN];1dzm;Benylate (TN);benzoic acid benzyl;Spectrum_001240;Benzoic acid-benzyl ester;Spectrum2_000532;Spectrum3_001757;Spectrum4_000773;Spectrum5_001128;ACMC-1C8AP;WLN: RVO1R;Benzyl benzoate, >=99%;EC 204-402-9;SCHEMBL3038;BENZYL BENZOATE BP98;BSPBio_003494;KBioGR_001186;KBioSS_001720;4-09-00-00307 (Beilstein Handbook Reference);KSC174Q0R;MLS001066412;MLS001336003;MLS001336004;DivK1c_000204;SPECTRUM1503002;Benzyl benzoate 120-51-4;SPBio_000543;Benzyl benzoate (JP17/USP);ZINC1021;DTXSID8029153;BENZOIC ACID,BENZYL ESTER;CTK0H4808;HMS500K06;KBio1_000204;KBio2_001720;KBio2_004288;KBio2_006856;KBio3_002714;KS-00000UHX;NSC8081;NINDS_000204;HMS1921P16;HMS2092F20;HMS2269D24;Pharmakon1600-01503002;HY-B0935;NSC-8081;Tox21_111372;Tox21_201337;Tox21_30341;ANW-17509;BDBM50134035;CCG-39578;NSC758204;s4599;SBB058609;STL183088;AKOS003495939;Benzyl benzoate, >=99%, FCC, FG;Tox21_111372_1;DB00676;LS-2573;MCULE-4369643785;NSC-758204;IDI1_000204;Benzyl benzoate, for synthesis, 99.0%;NCC00094981-01;NCGC00094981-02;NCGC00094981-04;NCGC00094981-05;NCGC00094981-07;NCGC00257502-01;NCGC00258889-01;AC-17033;AK308304;SBI-0051748.P002;DB-041563;B0064;FT-0622708;ST50406335;Benzyl benzoate, natural, >=99%, FCC, FG;Benzyl benzoate, ReagentPlus(R), >=99.0%;Benzyl benzoate, SAJ first grade, >=98.0%;Benzyl benzoate, tested according to Ph.Eur.;A14577;A19449;Benzyl benzoate, SAJ special grade, >=99.0%;C12537;D01138;AB00052298_07;Benzyl benzoate, Vetec(TM) reagent grade, 98%;Benzyl benzoate, meets USP testing specifications;Q413755;SR-01000763773;Benzoic acid-benzyl ester 5000 microg/mL in Hexane;Q-200696;SR-01000763773-2;BRD-K52072429-001-06-1;Benzoic acid benzyl ester; Benzoic acid phenylmethyl ester;Benzyl benzoate, certified reference material, TraceCERT(R);Benzyl benzoate, United States Pharmacopeia (USP) Reference Standard;Benzyl benzoate, Pharmaceutical Secondary Standard; Certified Reference Material

Benzyl benzoate( BB ). Acts as plasticizer and solvent. Used as a substitute for camphor in celluloid and plastic pyroxylin compounds. Faintly aromatic odor. Molecular weight is 212.24. Benzyl benzoate ( BB ) is also used as solvent for cellulose acetate as well as food additive in artificial flavors.

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

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

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

Uses

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

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

Non-medical
Benzyl benzoate is used as a repellent for chiggers, ticks, and mosquitoes.It is also used as a dye carrier, solvent for cellulose derivatives, plasticizer, and fixative in the perfume industry.

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

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

As an excipient in some testosterone-replacement injectable medications, benzyl benzoate has been reported as a cause of anaphylaxis in a case in Australia.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.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.

Benzyl benzoate usually comes with patient directions. Read them carefully before using this medicine.

Use this medicine only as directed. Do not use more of it and do not use it more often than recommended on the label. To do so may increase the chance of absorption through the skin and the chance of side effects.

Keep this medicine away from the eyes and other mucous membranes, such as the inside of the nose, because it may cause irritation . If you accidentally get some in your eyes, flush them thoroughly with water at once.

Do not use benzyl benzoate on open wounds, such as cuts or sores on the skin or scalp. To do so may increase the amount of absorption, which may increase the chance of side effects.

Your sexual partner or partners, especially, and all members of your household may need to be treated also, since the infestation may spread to persons in close contact. If these persons have not been examined for infestation or if you have any questions about this, check with your doctor.

To use this medicine for lice:

If your hair has any cream, lotion, ointment, or oil-based product on it, shampoo, rinse, and dry your hair and scalp well before applying benzyl benzoate.
Apply enough medicine to thoroughly wet the dry hair and scalp or skin.
Allow the medicine to remain on the affected areas for 24 hours.
Then, thoroughly wash the affected areas with warm water and soap or regular shampoo.
Rinse thoroughly and dry with a clean towel.
After rinsing and drying, use a fine-toothed comb (less than 0.3 mm between the teeth) to remove any remaining nits (eggs) or nit shells from your hair, or, if you have fine hair, you may use a tweezer or your fingernails to pick nits out.
To use this medicine for scabies:

If your skin has any cream, lotion, ointment, or oil on it, wash, rinse, and dry your skin well before applying benzyl benzoate.
If you take a bath or shower before using benzyl benzoate, dry the skin well before applying the medicine.
Apply enough medicine to cover the entire skin surface from the neck down, including the soles of your feet, and rub in well.
Allow the medicine to remain on the body for 24 hours.
Then, thoroughly wash the body with warm water and soap.
Rinse thoroughly and dry with a clean towel.
Immediately after using benzyl benzoate, wash your hands to remove any medicine that may be on them.

Treatment may need to be repeated for severe infestation.

Dosing
The dose of this medicine will be different for different patients. Follow your doctor's orders or the directions on the label. The following information includes only the average doses of this medicine. If your dose is different, do not change it unless your doctor tells you to do so.

The amount of medicine that you take depends on the strength of the medicine. Also, the number of doses you take each day, the time allowed between doses, and the length of time you take the medicine depend on the medical problem for which you are using the medicine.

For topical dosage form (emulsion):
For lice infestation:
Adults—Use just one time. For severe cases, treatment may be repeated two or three times after twenty-four hours.
Children—
For infants: Use mixed with three parts of water, just one time.
For older children: Use mixed with an equal quantity of water, just one time.
For scabies infestation:
Adults—Use just one time. For severe cases, treatment may be repeated after twenty-four hours one time anytime within five days.
Children—
For infants: Use mixed with three parts of water, just one time.
For older children: Use mixed with an equal quantity of water, just one time.
Storage
Store the medicine in a closed container at room temperature, away from heat, moisture, and direct light. Keep from freezing.

Keep out of the reach of children.

Do not keep outdated medicine or medicine no longer needed.

Preparation and use
– Shake the bottle before application or dilution.
– Dilute the lotion, as required, according to age. Use drinking or boiled water.
– Apply the lotion to the whole body, including scalp, postauricular areas, palms of the hands and soles of the feet, paying particular attention to skin creases and interdigital web spaces. Leave on for recommended contact time, then rinse thoroughly with water. 
– In children under 2 years: wrap hands to avoid accidental ingestion and contact with eyes.

Benzyl benzoate is one of the older preparations used to treat scabies. Scabies is a skin infection caused by the mite sarcoptes scabiei. It is characterised by severe itching (particularly at night), red spots, and may lead to a secondary infection. Benzyl benzoate is lethal to this mite and so is useful in the treatment of scabies. It is also used to treat lice infestation of the head and body. Benzyl benzoate is not the treatment of choice for scabies due to its irritant properties.

Exposure Routes and Pathways
Benzyl benzoate is an active substance in Peruvian and Tulu balsams as well as other essential oils. It is also produced synthetically and is formulated as a liquid, emulsion, or lotion. Exposure to benzyl benzoate can occur via skin contact or ingestion. Migration of benzyl benzoate and other compounds from toys was derived to estimate levels of oral and dermal exposure in children from contact with the toys. Benzyl benzoate had the highest migration rate among the tested compounds and the exposure levels were maximally estimated at 22.2 mg kg-1 bw day-1. Fetal exposure in rats following maternal exposure has also been documented.

Animal
Benzyl benzoate has low acute toxicity in laboratory animals. The oral LD50 value for rats is greater than 1 g kg-1. If applied too frequently or to a large area, it can induce systemic signs of toxicity including salivation, piloerection, muscular incoordination, tremors, progressive paralysis of hindlimbs, prostration, violent convulsions, dyspnea, and death. Cats are especially susceptible to such toxicity. In contrast, dogs are highly resistant to acute benzyl benzoate toxicity. When given in large doses to laboratory animals, benzyl benzoate can cause hyperexcitation, incoordination, ataxia, convulsions, and respiratory paralysis.

Benzyl Benzoate 10% to 25%.
Benzyl benzoate remains one of the most commonly prescribed agents for scabies in many parts of the world and compares favorably with other topical agents and oral ivermectin. Benzyl benzoate is not available in the US or Canada. The 25% emulsion is applied below the neck, with 3 applications during a 24-hour period. In young adults or children, the concentration can be reduced to 12.5%. Use can be complicated by allergic contact dermatitis, and benzyl benzoate should not be used during pregnancy, in lactating women, in infants, or in children younger than 2 years because of the risk for neurotoxicity.

Benzyl Benzoate
Benzyl benzoate can be made in a 10% to 25% solution for the topical treatment of scabies. Although there are no commercially available preparations, this medication is often compounded into a solution. There are few published human studies on its use for scabies, but it is commonly used in many countries outside the US, where it is reported to be a very inexpensive and effective compound. One study found that 15% benzyl benzoate applied twice daily for 3 days, used in combination with a single dose of ivermectin, was an extremely effective scabies treatment in a human immunodeficiency virus (HIV)-positive population.28 AE are usually limited to skin irritation. Additionally, patients should be advised to avoid alcohol consumption for 48 hours after benzyl benzoate application because of the possibility of a disulfiram-like reaction.29 Safety in pregnancy has not been established.

Benzyl Benzoate
M.A. Pearson, G.W. Miller, in Encyclopedia of Toxicology (Third Edition), 2014

Exposure Routes and Pathways
Benzyl benzoate is an active substance in Peruvian and Tulu balsams as well as other essential oils. It is also produced synthetically and is formulated as a liquid, emulsion, or lotion. Exposure to benzyl benzoate can occur via skin contact or ingestion. Migration of benzyl benzoate and other compounds from toys was derived to estimate levels of oral and dermal exposure in children from contact with the toys. Benzyl benzoate had the highest migration rate among the tested compounds and the exposure levels were maximally estimated at 22.2 mg kg-1 bw day-1. Fetal exposure in rats following maternal exposure has also been documented.

Benzyl Benzoate
Jamaluddin Shaikh, in Encyclopedia of Toxicology (Second Edition), 2005

Animal
Benzyl benzoate has low acute toxicity in laboratory animals. The oral LD50 value for rats is greater than 1 g kg-1. If applied too frequently or to a large area, it can induce systemic signs of toxicity including salivation, piloerection, muscular incoordination, tremors, progressive paralysis of hindlimbs, prostration, violent convulsions, dyspnea, and death. Cats are especially susceptible to such toxicity. In contrast, dogs are highly resistant to acute benzyl benzoate toxicity. When given in large doses to laboratory animals, benzyl benzoate can cause hyperexcitation, incoordination, ataxia, convulsions, and respiratory paralysis.

Ectoparasites (Lice and Scabies)
Dirk M. Elston, in Principles and Practice of Pediatric Infectious Diseases (Fifth Edition), 2018

Benzyl Benzoate 10% to 25%.
Benzyl benzoate remains one of the most commonly prescribed agents for scabies in many parts of the world and compares favorably with other topical agents and oral ivermectin. Benzyl benzoate is not available in the US or Canada. The 25% emulsion is applied below the neck, with 3 applications during a 24-hour period. In young adults or children, the concentration can be reduced to 12.5%. Use can be complicated by allergic contact dermatitis, and benzyl benzoate should not be used during pregnancy, in lactating women, in infants, or in children younger than 2 years because of the risk for neurotoxicity.

Topical Antiparasitic Agents
David W. Martell, Benjamin N. Lockshin, in Comprehensive Dermatologic Drug Therapy (Fourth Edition), 2021

Benzyl Benzoate
Benzyl benzoate can be made in a 10% to 25% solution for the topical treatment of scabies. Although there are no commercially available preparations, this medication is often compounded into a solution. There are few published human studies on its use for scabies, but it is commonly used in many countries outside the US, where it is reported to be a very inexpensive and effective compound. One study found that 15% benzyl benzoate applied twice daily for 3 days, used in combination with a single dose of ivermectin, was an extremely effective scabies treatment in a human immunodeficiency virus (HIV)-positive population.28 AE are usually limited to skin irritation. Additionally, patients should be advised to avoid alcohol consumption for 48 hours after benzyl benzoate application because of the possibility of a disulfiram-like reaction.29 Safety in pregnancy has not been established.

Antiparasitic drugs
Stephen W Page, in Small Animal Clinical Pharmacology (Second Edition), 2008

Benzyl benzoate
Benzoic acid phenylmethyl ester.

Clinical applications
Benzyl benzoate is used as a pediculicide and scabicide in dogs, although its principal use in humans is as a repellent of ticks, chiggers and mosquitoes. It is generally applied as a spot treatment.

Pharmacokinetics
Benzyl benzoate is rapidly absorbed and is hydrolyzed to benzoic acid and benzyl alcohol, conjugated with glycine or glucuronide and eliminated in urine.

Adverse effects

While generally considered of low toxicity, cats are about 10 times more sensitive than dogs (acute oral LD50 in cats is 2240 and in dogs 22,440 mg/kg) and its use in this species is contraindicated in some countries.

Signs of poisoning include salivation, twitching of treated areas, generalized tremors, convulsions, respiratory failure and death.

Treatment is symptomatic and supportive.

Treatment
Treatment of scabies is with topical permethrin, benzyl benzoate, malathion or oral ivermectin. The patient should apply 5% permethrin cream to the whole body, including the scalp, all folds, groin, navel, external genitalia and skin under the nails, washing it off after 12?hours. In adults with classical scabies, treatment of the face is controversial, but in babies the skin of the face should also be treated. A second application 7 days after the original treatment must be prescribed and all the affected members of a household require treatment at the same time to prevent cyclical reinfestations. Oral ivermectin is being increasingly used as a first-line treatment. Severe outbreaks require a second dose of ivermectin at a 2-week interval (200?µg/kg body weight). Treatment of secondary bacterial infection and antihistamines may be required. Washing clothes and linen at 60° will kill all the young fecundated female mites (an alternative is to keep these in a plastic bag for 48–72?hours, as mites separated from the human host die within this time). It is important to explain that pruritus commonly lasts for several weeks after cure, which may be partially alleviated by non-sedating or sedating antihistamines.

Benzyl benzoate is one of the older preparations used for the therapy of scabies. Scabies is a skin infection caused by the Sarcoptes scabiei. Its symptoms are red spots, severe itching (particularly at night), and may lead to a secondary infection. Benzyl benzoate is useful in the therapy of scabies because it is lethal to this mite. It is also used for the therapy of lice affection of the body and head. Benzyl benzoate is not the therapy of choice for scabies because of its irritant properties.