BENZYL BENZOATE

Formula: C6H5CH2OOCC6H5
INCI: Benzyl benzoate
CAS No.: 120-51-4
EINECS No.: 204-402-9
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 derives from a benzoic acid.

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.

Other names: benzoic acid phenylmethyl ester, benzy alcohol benzoic ester;CAS Number:120-51-4

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.

Production
Benzyl benzoate is produced industrially by the reaction of sodium benzoate with benzyl alcohol in the presence of a base, or by transesterification of methyl benzoate and benzyl alcohol.
It is a byproduct of benzoic acid synthesis by toluene oxidation. It can also be synthesized by the Tishchenko reaction, using benzaldehyde with sodium benzylate (generated from sodium and benzyl alcohol) as catalyst.

Benzyl benzoate 
Molecular Formula: C14H12O2
Average mass: 212.244 Da

CAS NO.    120-51-4    
BENZYL BENZOATE

EINECS NO.:204-402-9
FORMULA: C6H5CO2CH2C6H5
MOL WT: 212.25
H.S. CODE: 2916.31
    
 

TOXICITY: Oral rat LD50: 1700 mg/kg
SYNONYMS: Benzoic acid phenylmethyl ester; Benylate; Ascabin;Scabagen; Vanzoate; Benzyl Phenylformate; Benzyl Benzene Carboxylate; Benzyl Alcohol Benzoic Ester; Ascabiol; Benzoic Acid Benzyl Ester; Benzoato De Bencilo;

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE: Colourless oily liquid or leaflets depending on temperature
MELTING POINT: 17 C
BOILING POINT:323 C
SPECIFIC GRAVITY: 1.118 - 1.122
SOLUBILITY IN WATER:Insoluble
STABILITY: Stable under ordinary conditions
APPLICATIONS :Benzyl Benzoate is used for the synthesis of drugs (especially for antispasmodic drugs as a scabicides and to treat pediculosis). 
Benzyl benzoate finds application in fragrance. It is used in pre-fixing agent. Benzyl benzoate itself is not an active fragrance ingredient.
It improves the stability and odor characteristics of the main ingredients. It is used as a miticide and in food field. It is also used as a plasticizer for polymers and cellulose.
CAS No.    120-51-4
Flavor/Fragrance Notes:Nearly odorless
TYPICAL PROPERTIES
Assay USP/EP (titration): 99.0-100.5% of phenyl methyl benzoate; FCC (GC): 99.0% minimum
Odor:Nearly odorless
Color: Colorless
Appearance: Clear liquid
Flash Point: 148°C (298°F)
Refractive Index (20°C): 1.568 – 1.570
Density (20°C) (g/ml):1.118 – 1.122
Specific Gravity (25°C):1.116 – 1.120
Solidification Point:18 – 21°C (64 – 70°F)
Acid Value (mgKOH/g):1.0 maximum

BENZYL BENZOATE
120-51-4
Ascabiol
Benzoic acid, phenylmethyl ester
Benzoic acid benzyl ester
Benzyl phenylformate
Phenylmethyl benzoate
Benzoic acid, benzyl ester
Benzylets
Benzyl benzenecarboxylate
benzylbenzoate
Antiscabiosum
Benzyl alcohol benzoic ester
Peruscabina
Spasmodin
Venzonate
Benzylis benzoas
Benzylum benzoicum
Benzylester kyseliny benzoove
Benzoesaeurebenzylester
BENZOIC ACID PHENYLMETHYLESTER
Caswell No. 082
Benzylbenzenecarboxylate
EINECS 204-402-9
Benzylester kyseliny benzoove [Czech]
Benzyl benzoate, 99+%
Venzoate
BZM
CAS-120-51-4
benzylbenzoat
Benzyl benzoate [USP:JAN]
Benzyl benzoate [USAN:JAN]
Benzyl Benzoate.
benzoic acid benzyl
BENZYL BENZOATE BP98
BENZOIC ACID,BENZYL ESTER
Benzyl benzoate, >=99%, FCC, FG
Benzyl benzoate, for synthesis, 99.0%
Benzyl benzoate, natural, >=99%, FCC, FG
Benzoic acid-benzyl ester 
Benzoic acid benzyl ester; Benzoic acid phenylmethyl ester

Bensüülbensoaat (et)
bentsyylibentsoaatti (fi)
benzil benzoat (sl)
benzil-benzoat (hr)
benzil-benzoát (hu)
benzilbenzenkarboksilatas (benzilbenzoatas) (lt)
benzilbenzoāts (lv)
benzile benzoato (it)
benzoat de benzil (ro)
benzoate de benzyle (fr)
benzoato de bencilo (es)
benzoato de benzilo (pt)
benzoesan benzylu (pl)
benzyl-benzoát (cs)
benzyl-benzoát (sk)
benzylbenzoaat (nl)
benzylbenzoat (da)
Benzylbenzoat (de)
benzylbenzoat (no)
benzylbenzoat (sv)
benżoat tal-benżil (mt)
βενζοϊκό βενζύλιο (el)
бензил бензоат (bg)

CAS names
Benzoic acid, phenylmethyl ester
IUPAC names
Benzil-benzoát
benzoic acid phenyl methyl ester
Benzoic acid, benzylester
BENZOIC ACID, PHENYL METHYL ESTER
Benzoic acid, phenylmethyl ester
Registration dossier
benzyl benxoate
BENZYL BENZOATE
Benzyl benzoate; Phenylmethyl benzoate
benzyl-2-methyl-hydroxybutyrate dehydrogenase
benzylbenzoate
phenylmethyl benzoate

120-51-4 [RN]
204-402-9 [EINECS]
2049280 [Beilstein]
2138
Benzoate de benzyle [French] [ACD/IUPAC Name]
benzoic acid benzyl ester
benzoic acid, benzyl ester
Benzoic acid, phenylmethyl ester [ACD/Index Name]
Benzyl benzoate [ACD/IUPAC Name] [Wiki]
Benzylbenzoat [German]
Benzyl-benzoat [German] [ACD/IUPAC Name]
Benzylis benzoas
DG4200000
MFCD00003075 [MDL number]
N863NB338G
phenylmethyl benzoate
[120-51-4]
347840-01-1 [RN]
352431-26-6 [RN]
4-09-00-00307 (Beilstein Handbook Reference) [Beilstein]
613-62-7 [RN]
Acarilbial
Acarilbial (Trade name)
Acaril-S
Acaril-S (Trade name)
Acaril-S; Acarilbial; Acarsan; Acil; Antiscabiosum; Antiscabiosum für Kinder; Ascabiol; Ascalol; B.B. Lotion; BE BO; Benzalcor; Benzilbenzoat; Benzogal; Benzotal; Bezo; Finsarna; Gensarna; Miticocan; Novoscabin; Opele; Pharcobenzyl; Sanasar; Saniscabis; Scabicon; Scabiex; Scabin; Scabisol; Scabitox; Tekoce; Zilaben
Acarobenzyl
Acarobenzyl; Benylate; Benzevan; Benzoate de benzyle; Benzoes??urebenzylester; Benzoic acid phenylmethylester; Benzoic acid, benzyl ester; Benzoic acid, phenylmethyl ester; Benzyl benzoat; Benzylis benzoas; Phenylmethyl benzoate
Acarobenzyl; Benzevan; Benzoate de benzyle; Benzoesäurebenzylester; Benzyl benzoat; Benzylis benzoas; Phenylmethyl benzoate; Spasmodine
Acarsan
Acarsan (Trade name)
Acil
Acil (Trade name)
Antiscabiosum
Antiscabiosum (Trade name)
Antiscabiosum für Kinder
Antiscabiosum für Kinder (Trade name)
Ascabin
Ascabiol
Ascabiol (Trade name)
Ascalol
Ascalol (Trade name)
B.B. Lotion
B.B. Lotion (Trade name)
BE BO
BE BO (Trade name)
Benylate [Trade name]
Benylate (TN)
Benzalcor
Benzalcor (Trade name)
Benzevan
Benzilbenzoat
Benzilbenzoat (Trade name)
Benzoate de benzyle [ACD/IUPAC Name]
Benzoes??urebenzylester
Benzoesaeurebenzylester
Benzoesäurebenzylester
Benzogal
Benzogal (Trade name)
benzoic acid phenylmethyl ester
BENZOIC ACID PHENYLMETHYLESTER
BENZOIC ACID,BENZYL ESTER
Benzoic acid-benzyl ester
Benzotal (Trade name)
Benzyl 2-naphthyl ether
Benzyl alcohol benzoic ester
Benzyl benzenecarboxylate
Benzyl benzoat
Benzyl benzoate (JP15/USP) [USP]
Benzyl benzoate (natural)
Benzyl benzoate [USAN:JAN]
benzyl benzoate 99%
BENZYL BENZOATE BP98
benzyl benzoate, 99+%
Benzyl benzoate, BP, Ph. Eur. grade
Benzyl benzoate, USP grade
Benzyl Benzoate-d12
Benzyl phenylformate
Benzylbenzenecarboxylate
benzylbenzoate
benzyl-benzoate
Benzyl-d5 Benzoate
Benzylester kyseliny benzoove
Benzylester kyseliny benzoove [Czech]
Benzylets
Benzylum benzoicum
Bezo
Bezo (Trade name)
BZM
Colebenz
EINECS 204-402-9
Finsarna
Finsarna (Trade name)
Gensarna
Gensarna (Trade name)
Mange Treatment
Miticocan
Miticocan (Trade name)
Novoscabin
Novoscabin (Trade name)
Opele
Opele (Trade name)
Peruscabin
Peruscabina
Pharcobenzyl
Pharcobenzyl (Trade name)
Pharmakon1600-01503002
Sanasar
Sanasar (Trade name)
Saniscabis
Saniscabis (Trade name)
Scabagen
Scabanca
Scabicon
Scabicon (Trade name)
Scabide
Scabiex
Scabiex (Trade name)
Scabin
Scabin (Trade name)
Scabiozon
Scabisol
Scabisol (Trade name)
Scabitox
Scabitox (Trade name)
SCOBENOL
SMR000471875
Spasmodin
Spasmodine
SPECTRUM1503002
Spectrum5_001128
ST5406335
Tekoce
Tekoce (Trade name)
Vanzoate
Venzoate
Venzonate
WLN: RVO1R
Zilaben
安息香酸ベンジル [Japanese]