Benzyl Benzoate

HCID 2345CAS 120-51-4

Grundinformationen

Standard-SMILES
O=C(OCc1ccccc1)c1ccccc1
InChIKey
SESFRYSPDFLNCH-UHFFFAOYSA-N
Summenformel
C14H12O2
Durchschnittliche Molmasse
212,24 g/mol
Monoisotopische Masse
212,08372962

Namen und Bezeichner

Bevorzugter Name
Benzyl Benzoate
IUPAC
benzyl benzoate
Englischer Name
Benzyl benzoate
Summenformel
C14H12O2
Molmasse
0

Namen und Synonyme

BENZYL BENZOATE120-51-4AscabiolBenzoic acid, phenylmethyl esterBenylateBenzoic acid, benzyl esterScobenolPhenylmethyl benzoateAscabinNovoscabinScabiozonBenzyl phenylformate
Weitere Namen anzeigen
BenzyletsColebenzPeruscabinScabancaScabagenScabitoxVanzoateVenzonate

Datenbank-Bezeichner

CAS
120-51-4
PubChem CID
2345
DTXSID
DTXSID8029153
ChEMBL
CHEMBL1239
ChEBI
CHEBI:41237
UNII
N863NB338G
EC Number
204-402-9
Nikkaji
J5.327I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
4
Schwere Atome
16

Experimentelle und physikochemische Eigenschaften

pHSolution in alcohol practically neutral to moistened litmus paper
LogP · 4 Einträge

3.97

log Kow = 3.97

3.7

3.97

Odor · 2 Einträge

Light, balsamic odor reminiscent of almond

Faint, pleasant, aromatic odor

TasteSharp burning taste
Density · 4 Einträge

1.1121 g/cu cm at 25 °C

Relative density (water = 1): 1.1

1.113-1.121

1.116 @25 °C

Viscosity8.292 cP at 25 °C

Physikochemische Eigenschaften

Schmelzpunkt
17 · 17-20 °C
Siedepunkt
324 °C · 324°C
Dichte
1.116 · 1.116
Dampfdichte
7.3 · 7.3
Dampfdruck
0.000224 mm · 0.000224 mm Hg @ 250C
Brechungsindex
1.569 · 1.569-1.570

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral];H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Warning

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Benzoic acid, phenylmethyl ester

Hazard Traits - Fragrance Allergen;Authoritative List - Annex III of the EU Cosmetics Regulation No. 1223/2009 - Fragrance Allergens;Report - if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzoic acid, phenylmethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, phenylmethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13634

Benzyl benzoate: HSNO Approval: HSR003504 Approved with controls

Other Safety InformationIMAP assessments - Benzoic acid, phenylmethyl ester: Human health tier I assessment
Fire HazardsCombustible.
Fire PotentialCombustible liquid.
Hazards Summary · 1 Eintrag

A skin, eye, and respiratory tract irritant; [ICSC] Included in list of established contact allergens in humans; [EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] Harmful if swallowed; [MSDSonline] Direct contact may cause skin irritation but rarely allergic contact dermatitis. [Kanerva, p. 1757]

FDA Requirements · 3 Einträge

Synthetic flavoring substances and adjuvants may be safely used in food in accordance with the following conditions. (a) They are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice. (b) They consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. Benzyl benzoate is included on this list.

Benzyl benzoate is an indirect food additive for use as a component of adhesives.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses ... . However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: benzyl benzoate is included in pediculicide drug products.

Sicherheit und Schutzausrüstung

Fire FightingUse water spray, powder, foam, carbon dioxide.
First Aid Measures · 3 Einträge

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Safe StorageVentilation along the floor.
Fire Fighting Procedures · 3 Einträge

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

To fight fire, use carbon dioxide, water spray or mist, dry chemical.

Storage Conditions · 2 Einträge

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.

Benzyl benzoate should be stored in light-resistant containers and should not be exposed to excessive heat.

Cleanup Methods · 1 Eintrag

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. 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.

Toxikologische Informationen

Interactions · 1 Eintrag

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.

Ecotoxicity Values · 5 Einträge

LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 14 days; diet (in food) >5000 ppm for 8 days /99.4% purity/

LD50; Species: Colinus virginianus (Northern Bobwhite Quail) age 23 weeks; oral via capsule >2000 mg/kg /99.4% purity/

LC50; Species: Oncorhynchus mykiss (Rainbow trout) mature; Conditions: freshwater, flow through; Concentration: 4.8 mg/L for 96 hr /99.8% purity/

LC50; Species: Gammarus fasciatus (Scud) mature; Conditions: freshwater, static; Concentration: 9.8 mg/L for 24 hr /99% purity/

LC50; Species: Gammarus fasciatus (Scud) mature; Conditions: freshwater, static; Concentration: 4.8 mg/L for 96 hr /99% purity/

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2500(SRC), determined from a structure estimation method(2), indicates that benzyl benzoate is expected to have slight mobility in soil(SRC). Volatilization of benzyl benzoate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Benzyl benzoate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.24X10-4 mm Hg at 25 °C(3). Utilizing the Japanese MITI test, 90% of the Theoretical BOD was reached in 4 weeks(4) indicating that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2500(SRC), determined from a structure estimation method(2), indicates that benzyl benzoate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.3X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 190(SRC), from its log Kow of 3.97(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Hydrolysis is not expected to be an important environmental fate process as suggested by estimated acid-base hydrolysis half-lives of 1.7 years and 63 days at pH 7 and pH 8, respectively(1). Utilizing the Japanese MITI test, 90% of the Theoretical BOD was reached in 4 weeks(6) indicating that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzyl benzoate, which has a vapor pressure of 2.25X10-4 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase benzyl benzoate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 55 hrs(SRC), calculated from its rate constant of 7.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase benzyl benzoate may be removed from the air by wet and dry deposition(SRC). Benzyl benzoate contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1 Eintrag

Benzyl benzoate has been reported at a concentration of 0.22 ug/g in volatiles from pineapple guava (Feihoa sellowiana Berg) fruit(1). The compound was detected, not quantified in new fraction of volatiles of clove essential oil (Eugenia carophyllus Spreng)(2).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Regulatorische Informationen

Regulatory Information · 6 Einträge

Chemical: Benzoic acid, phenylmethyl ester

Hazard Traits - Fragrance Allergen;Authoritative List - Annex III of the EU Cosmetics Regulation No. 1223/2009 - Fragrance Allergens;Report - if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzoic acid, phenylmethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, phenylmethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13634

Benzyl benzoate: HSNO Approval: HSR003504 Approved with controls

FDA Requirements · 3 Einträge

Synthetic flavoring substances and adjuvants may be safely used in food in accordance with the following conditions. (a) They are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice. (b) They consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. Benzyl benzoate is included on this list.

Benzyl benzoate is an indirect food additive for use as a component of adhesives.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses ... . However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: benzyl benzoate is included in pediculicide drug products.

FIFRA Requirements · 2 Einträge

The Agency has completed its review of submitted data and its assessment of the residential and occupational risks associated with the use of pesticide products containing the active ingredient benzyl benzoate. Based on these data, the Agency has sufficient information on the human health effects of benzyl benzoate to make its decision as part of the reregistration process under FIFRA. ... the registrant for AllerCare products Raid Product 319 and Raid Product 420, has asked for the voluntary cancellation of both products. The Agency has determined that all other remaining benzyl benzoate products are eligible for registration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Benzyl benzoate is found on List D. Case No: 4013; Pesticide type: insecticide, fungicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Benzyl benzoate; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Atmospheric Standards · 1 Eintrag

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Benzyl benzoate is produced, as an intermediate or a final product, by process units covered under this subpart.

Sicherheitsdaten

Toxizität
LD50 orl-rat: 1700 mg/kg JPETAB 93,26,48
packing_group
III
Selbstentzündungstemperatur
480°C

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

P - Antiparasitic products, insecticides and repellents;P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents;P03A - Ectoparasiticides, incl. scabicides;P03AX - Other ectoparasiticides, incl. scabicides;P03AX01 - Benzyl benzoate

QP - Antiparasitic products, insecticides and repellents;QP53 - Ectoparasiticides, insecticides and repellents;QP53A - Ectoparasiticides for topical use, incl. insecticides;QP53AX - Other ectoparasiticides for topical use;QP53AX11 - Benzylbenzoate

P03AX01

Pharmacodynamics · 1 Eintrag

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.

Mechanism of Action · 1 Eintrag

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.

Metabolism/Metabolites · 2 Einträge

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.

MeSH Pharmacological ClassificationPesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Absorption, Distribution and Excretion · 3 Einträge

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.

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Benzyl Benzoate

Used in plastic pyroxylin compounds, flavors, perfumes, plasticizers, dye carriers, antispasmodic drugs, insect repellants, scabicides , and pediculicides; [HSDB] Used as a dye carrier and a solvent for cellulose derivatives, plasticizers, and perfume fixatives; It is the main constituent in Peru balsam; Used in drugs for asthma; [Ullmann]

For benzyl benzoate (USEPA/OPP Pesticide Code: 009501) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

As solvent of cellulose acetate, nitrocellulose and artificual musk; substitute for camphor in celluloid and plastic pyroxylin compounds; perfume fixative; in confectionary and chewing gum flavors.

Fixative and solvent for musk in perfumes and flavors; medicine (external); plasticizer for nitrocellulose and cellulose acetate, miticide.

Reported uses (ppm):;Table: Reported uses (ppm): (Flavor and Extract Manufacturers' Association, 1994) [Table#818]

U.S. Production · 5 Einträge

2023: 10,000,000 - <25,000,000 lb;2022: 10,000,000 - <25,000,000 lb;2021: 10,000,000 - <25,000,000 lb;2020: 10,000,000 - <25,000,000 lb

(1972) 1.85X10+8 GRAMS

(1975) 3.35X10+8 GRAMS

(1991) 287,000 kg

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzyl benzoate:;Table: National Aggregate Production Volume (pounds) [Table#817]

Consumer UsesFragrance;Plasticizer;Not Known or Reasonably Ascertainable
Industry UsesFlavoring and nutrient;Solvent;Not Known or Reasonably Ascertainable;Fixing agent (mordant);Fragrance
IFRA Fragrance Standards · 6 Einträge

Benzyl benzoate

Benylate; Benzoic acid, benzyl ester; Benzoic acid, phenylmethyl ester; Benzyl phenylformate; Phenylmethyl benzoate

IFRA_STD_009.pdf

49

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Restriction: This material should be used only in the limited quantity as stated in the Standard

Methods of Manufacturing · 5 Einträge

Prepared by the action of sodium benzylate on benzaldehyde ... ; by the dry esterification of sodium benzoate and benzyl chloride in the presence of triethylamine.

Derivation: (a) By a Cannizzaro reaction from benzaldehyde, (b) by esterifying benzyl alcohol with benzoic acid, (c) by treating sodium benzoate with benzyl chloride. Method of purification: Distillation and crystallization.

Benzyl benzoate is produced by esterifying dry sodium benzoate with benzyl chloride or by the dimerization of benzaldehyde. It is also obtained from the bottoms of benzoic acid rectification plants.

Benzyl benzoate is produced from benzyl alcohol and sodium benzoate in the presence of triethylamine or transesterification of methyl benzoate with benzyl alcohol in the presence of an alkali benzyl oxide; in another manufacturing process benzaldehyde is condensed to form benzyl benzoate in the presence of sodium (Claisen-Tishchenko condensation)

By the dry esterification of sodium benzoate and benzoyl chloride in the presence of triethylamine or by reaction of sodium benzylate on benzaldehyde.

Anbieter50 Anbieter

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