Absorption, Distribution and Excretion
No data are available on percutaneous absorption of benzyl benzoate. Some older studies have suggested some percutaneous absorption, however the amount was not quantified.
The maternal and fetal toxicity of benzyl benzoate, commonly used as antiparasitic insecticide, was evaluated in pregnant rats after a daily oral dose of 25 and 100 mg/kg. Biochemical, histopathological, and morphological examinations were performed. Dams were observed for maternal body weights and food and water consumption and subjected to caesarean section on (GD) 20. Maternal and fetal liver, kidney, heart, brain, and placenta were examined histopathologically under light microscope. Maternal and fetal liver and placenta were stained immunohistochemically for vascular endothelial growth factor (VEGF). Morphometric analysis of fetal body lengths, placental measurements, and fetal skeletal stainings was performed. Statistically significant alterations in biochemical parameters and placental and skeletal measurements were determined in treatment groups. In addition to histopathological changes, considerable differences were observed in the immunolocalization of VEGF in treatment groups. These results demonstrated that benzyl benzoate and its metabolites can transport to the placenta and eventually enter the fetuses.
The percutaneous absorption of benzyl benzoate measured in vivo in human and monkey studies. With the application sites occluded, 54% of the applied dose penetrated human skin in 24 hr compared with 69% absorption in the monkey skin.

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Metabolism / Metabolites
Rapidly hydrolyzed to benzoic acid and benzyl alcohol, which is further oxidized to benzoic acid. The benzoic acid is conjugated with glycine to form hippuric acid.
Converted to hippuric acid in vivo.

Toxicity Summary
IDENTIFICATION AND USE: Benzyl benzoate is a liquid. It is used as solvent of cellulose acetate, nitrocellulose and artificial musk, substitute for camphor in celluloid and plastic pyroxylin compounds, perfume fixative, in confectionary and chewing gum flavors. As an insecticide/miticide, it was used to control dust mites in carpets, mattresses, upholstery, and on furniture. Benzyl benzoate is used as an alternative agent for the topical treatment of scabies and also has been used for the topical treatment of pediculosis (lice infestation). It is also used in veterinary medicine as acaricide and pediculicide, but is contraindicated in cats. It was used in the Vietnam War to eradicate and repel certain ticks and mites. HUMAN STUDIES: Direct contact may cause skin irritation. Liquid is irritating to eyes on direct contact, but no damage has been reported. There was no evidence of adverse effects on pregnancy outcome due to topical benzyl benzoate lotion. Benzyl benzoate gave estrogenic responses in a human breast cancer cell line in culture. ANIMAL STUDIES: 13-week study in rats demonstrated decreased body weight gain and mortality at 800 mg/kg/day. Neurotoxicity signs noted such as staggering, respiratory difficulty, and lethargy. Hemorrhages were found around the mouth and nose, and histologic lesions in the brain, thymus, skeletal muscle, and kidney. Benzyl benzoate was not tested for carcinogenicity, but the metabolite benzyl alcohol was tested in rats and mice. No evidence of carcinogenic activity was found in benzyl alcohol. The maternal and fetal toxicity of benzyl benzoate was evaluated in pregnant rats after a daily oral dose of 25 and 100 mg/kg. The results demonstrated that benzyl benzoate and its metabolites can transport to the placenta and eventually enter the fetuses. Benzyl benzoate was tested for mutagenicity and found to be negative in inducing unscheduled glycol nucleic acid synthesis in rat liver cells. The chemical did not cause damage to hormones nor did it cause mammalian cell mutations in vitro.

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Interactions
The use of benzyl benzoate as a vehicle constituent in administering cyproterone acetate caused morphological changes detectable at the ultrastructural level in the adrenal cortex. Castor oil and benzyl benzoate in a 4:1 ratio caused intracellular as well as intercellular changes. In the zona fasciculata there were alterations in mitochondrial shape, size, and matrix. Intercellular changes affected the morphology of macrophages in the zona fasciculata and zona reticularis. It is believed that the castor oil and benzyl benzoate vehicle caused stress-induced changes.

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Non-Human Toxicity Values
LD50 Rat oral 1700 mg/kg
LD50 Rat dermal 4 g/kg
LD50 Mouse oral 1400 mg/kg
LD50 Cat oral 2240 mg/kg
For more Non-Human Toxicity Values (Complete) data for Benzyl benzoate (11 total), please visit the HSDB record page.

Benzyl benzoate is a benzoate ester obtained by the formal condensation of benzoic acid with benzyl alcohol. It has been isolated from the plant species of the genus Polyalthia. It has a role as a scabicide, an acaricide and a plant metabolite. It is a benzyl ester and a benzoate ester. It is functionally related to a benzoic acid.
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.
Benzyl benzoate has been reported in Camellia sinensis, Desmos chinensis, and other organisms with data available.

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Drug Indication
Used to kill lice and the mites responsible for the skin condition scabies.

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Mechanism of Action
Benzyl benzoate exerts toxic effects on the nervous system of the parasite, resulting in its death. It is also toxic to mite ova, though its exact mechanism of action is unknown. In vitro, benzyl benzoate has been found to kill the Sarcoptes mite within 5 minutes.

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Therapeutic Uses
Benzyl benzoate is used as an alternative agent for the topical treatment of scabies and also has been used for the topical treatment of pediculosis (lice infestation). ... Benzyl benzoate lotion, in an approximate concentration of 28% w/w, is applied topically. The drug should not be administered orally. Containers of the lotion should be shaken before using.
Scabicide, pediculicide.
VET: Acaricide, pediculicide. Contraindicated in cats.

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Drug Warnings
Studies in animals showed that oral ingestion of large doses of benzyl benzoate resulted in progressive incoordination, CNS excitation, seizures, and death.
When used in appropriate dosage, topically applied benzyl benzoate appears to have a low order of toxicity. Slight local irritation (especially of the male genitalia), itching, and allergic skin sensitivity may occur, and contact with the face, eyes, mucous membranes, and urethral meatus should be avoided. Repeated application of benzyl benzoate frequently causes contact dermatitis.
Benzyl benzoate is contraindicated in patients with a history of hypersensitivity to the drug.
Benzyl benzoate should not be applied to acutely inflamed skin or raw, weeping surfaces. If primary irritation or hypersensitivity occurs, treatment should be discontinued and the drug removed with soap and water.
VET: Cats are particularly susceptible to this action, and the use of benzyl benzoate in this species is therefore contraindicated. The most prominent feature is nervous excitability. The clinical signs resemble those of poisoning by benzoic acid.

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Pharmacodynamics
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.

C14H12O2

212.2439

212.083

120-51-4

Benzyl benzoate-d5;347840-01-1;Benzyl benzoate-d12;352431-26-6

2345

Leaflets or oily liquid
Water-white liquid
Colorless, oily liquid
Clear, colorless liquid

1.1±0.1 g/cm3

324.1±11.0 °C at 760 mmHg

18 °C

147.8±0.0 °C

0.0±0.7 mmHg at 25°C

1.579

3.97

0

2

4

16

213

0

O(C(C1C([H])=C([H])C([H])=C([H])C=1[H])=O)C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H]

SESFRYSPDFLNCH-UHFFFAOYSA-N

InChI=1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2

benzyl benzoate

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ≥ 50 mg/mL (~235.58 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (11.78 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (11.78 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (11.78 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)