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Benzyl benzoate is a benzoate ester obtained by the formal condensation of benzoic acid with benzyl alcohol.
Benzoic Acid Benzyl Ester (Benzyl Benzoate) has been isolated from the plant species of the genus Polyalthia.
Benzoic Acid Benzyl Ester (Benzyl Benzoate) has a role as a scabicide, an acaricide and a plant metabolite.
Benzoic Acid Benzyl Ester (Benzyl Benzoate) is a benzyl ester and a benzoate ester.
Benzoic Acid Benzyl Ester (Benzyl Benzoate) is functionally related to a benzoic acid.
CAS : 120-51-4
SYNONYMS
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Benzyl benzoate is an organic compound with the formula C₆H₅CH₂O₂CC₆H₅.
Benzoic Acid Benzyl Ester (Benzyl Benzoate) is the ester of benzoic acid and benzyl alcohol.
Benzoic Acid Benzyl Ester (Benzyl Benzoate) is widely used in industries ranging from cosmetics and pharmaceuticals to plastics and food.
Molecular Formula: C₁₄H₁₂O₂
Molar Mass: 212.25 g/mol
CAS Number: 120-51-4
Benzoic Acid Benzyl Ester (Benzyl Benzoate) is naturally found in essential oils, such as balsam of Peru and tolu balsam.
Benzoic Acid Benzyl Ester (Benzyl Benzoate) exhibits several notable chemical and physical properties that make it versatile in industrial and pharmaceutical applications.
PHYSICAL AND CHEMICAL PROPERTIES
Physical Properties:
Appearance: Colorless to pale yellow liquid or crystalline solid at room temperature.
Odor: Pleasant, slightly balsamic.
Melting Point: 18°C (64°F).
Boiling Point: 323°C (613°F).
Density: 1.118 g/cm³ at 20°C.
Solubility:
Insoluble in water.
Soluble in alcohol, ether, and chloroform.
Chemical Properties:
Functional Groups: Ester group (-COO-).
Reactivity:
Hydrolyzes under acidic or basic conditions to yield benzoic acid and benzyl alcohol.
Resistant to oxidation under standard conditions.
Synthesis of Benzyl Benzoate
Industrial Synthesis:
Benzyl benzoate is produced through an esterification reaction between benzoic acid and benzyl alcohol in the presence of an acid catalyst (e.g., sulfuric acid or p-toluenesulfonic acid).
Reaction:
C₆H₅COOH+C₆H₅CH₂OH→C₆H₅CH₂OCOC₆H₅+H₂OC₆H₅COOH+C₆H₅CH₂OH→C₆H₅CH₂OCOC₆H₅+H₂O
Laboratory Synthesis:
In a laboratory setting, benzyl benzoate can also be synthesized via the Fischer esterification process or by the transesterification of methyl benzoate with benzyl alcohol.
APPLICATIONS OF BENZOIC ACID BENZYL ESTER (BENZYL BENZOATE)
Pharmaceutical Uses:
Treatment for Scabies: Benzyl benzoate is an active ingredient in lotions and creams for treating scabies and pediculosis (lice infestation).
Benzoic Acid Benzyl Ester (Benzyl Benzoate) acts as a miticide by killing mites and lice.
Solvent in Medicinal Preparations: It serves as a carrier for active pharmaceutical ingredients (APIs).
Cosmetic Industry:
Used as a fixative in perfumes to stabilize the fragrance.
Acts as a solvent and plasticizer in formulations for creams and lotions.
Food Industry:
Approved as a food additive in some countries for its antimicrobial and preservative properties.
Other Industrial Applications:
Plasticizer: In polymers and cellulose-based plastics.
Repellent: Used to deter insects.
Lubricant Additive: To enhance the performance of lubricants.
Mechanism of Action
In treating scabies, benzyl benzoate works by penetrating the exoskeleton of mites and disrupting their metabolic processes, leading to their death.
Its insecticidal and acaricidal properties make it effective against a variety of ectoparasites.
Regulatory Status:
Approved for limited use in personal care products and food by the FDA and European regulatory bodies.
Analytical Methods for Identification
Chromatographic Techniques:
Gas Chromatography (GC): Used to quantify benzyl benzoate in mixtures.
High-Performance Liquid Chromatography (HPLC): Allows for separation and analysis in complex matrices.
Spectroscopic Techniques:
Infrared (IR) Spectroscopy: Characteristic ester peaks at ~1735 cm⁻¹.
Nuclear Magnetic Resonance (NMR):
¹H NMR: Shows signals for aromatic and methylene protons.
¹³C NMR: Peaks corresponding to ester carbonyl and aromatic carbons.
Pharmacological Profile
Benzyl benzoate is non-systemic, meaning it primarily acts on the surface of the skin without significant absorption into the bloodstream.
Its acaricidal effects are linked to its ability to interfere with the nervous system of mites and lice.
Environmental Impact
Biodegradability:
Benzyl benzoate is readily biodegradable in soil and aquatic systems, reducing the risk of long-term environmental persistence.
Ecotoxicity:
Moderately toxic to aquatic organisms (e.g., fish and crustaceans).
Low bioaccumulation potential due to its metabolic breakdown in organisms.
Future Perspectives
Research on benzyl benzoate is exploring its potential:
As a green solvent in organic synthesis.
In novel drug formulations for enhanced skin delivery systems.
For use in eco-friendly insect repellents.
SAFETY INFORMATION ABOUT BENZOIC ACID BENZYL ESTER (BENZYL BENZOATE)
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
