Benzylbenzoat Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSE FLüSSIGKEIT ODER WEISSER FESTSTOFF MIT CHARAKTERISTISCHEM GERUCH.
PHYSIKALISCHE GEFAHREN
Die Dämpfe sind schwerer als Luft.
CHEMISCHE GEFAHREN
Beim Verbrennen Bildung giftiger und reizender Rauche.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation des Aerosols, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Nur ungenügende Angaben vorhanden über die Geschwindigkeit, mit der eine gesundheitsschädliche Konzentration in der Luft beim Verdampfen bei 20°C erreicht wird.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz reizt die Augen, die Haut und die Atemwege.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann Dermatitis hervorrufen.
LECKAGE
Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. Persönliche Schutzausrüstung: Atemschutzgerät, P1-Filter für inerte Partikel.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S25:Berührung mit den Augen vermeiden.
Beschreibung
Benzyl benzoate is the ester of benzyl alcohol and benzoic acid, with the formula C
6H
5CH
2O
2CC
6H
5. This easily prepared compound with a mild balsamic odor has a variety of uses.Benzyl benzoate (BB) is one of the oldest drugs used for the treatment
of scabies and is recommended as the “first-line intervention” for the
cost-effective treatment of the disease.
Chemische Eigenschaften
Benzyl Benzoate is the main component of Peru balsam oil. It occurs in fairly large amounts in a number of blossom concretes and absolutes (e.g., tuberose and hyacinth). It forms either a viscous liquid or solid flakes (mp 21–22°C) and has a weak, sweet, balsamic odor.
Benzyl Benzoate is prepared either by transesterification of technical methyl benzoate with benzyl alcohol or from benzyl chloride and sodium benzoate. A third process starts with benzaldehyde, which is converted in high yield into benzyl benzoate in the presence of sodium or aluminum benzylate (Tishchenko reaction). Benzyl benzoate is used in perfumery as a fixative and as a modifier in heavy blossom fragrances.
Occurrence
Contained in Peru balsam and in the concrete and absolute of tuberose flowers, hyacinth, Narcissus jonquilla
L., and Dianthus caryophillus L.; also in the oil of ylang-ylang and in Tolu balsam. Reported found in American cranberry, cinnamon
bark, cassia leaf, corn oil and hog plum (Spondias mombins L.).
Verwenden
benzyl benzoate is an anti-microbial. It can also act as a solvent, helping dissolve other substances in the product, and as a perfuming ingredient. It is the ester of benzyl alcohol and benzoic acid.
Definition
ChEBI: 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.
Definition
Benzyl benzoate is produced from benzyl alcohol and sodium benzoate in the presence of triethylamine or by 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). The presence of a small amount of an aliphatic ether improves this reaction. Benzyl benzoate is a byproduct in the manufacture of benzoic acid by the oxidation of toluene; it is present in the benzoic acid distillation residue.
synthetische
By the dry esterification of sodium benzoate and benzoyl chloride in the presence of triethylamine or by reaction of
sodium benzylate on benzaldehyde.
Indications
Benzyl benzoate: 20% to 25%. This agent is relatively nontoxic and is widely
used in developing countries to treat scabies and pediculosis capitis and pubis.
Only a veterinary preparation is available in the United States. Benzyl benzoate is
synthetically derived from the esterification of benzoic acid with benzyl alcohol. Its
mechanism of action is unknown. It is toxic to Sarcoptes scabei and may be toxic
to Pediculosis capitis and Phthirus pubis. No resistance has been demonstrated
to date.
Benzyl benzoate can be used in a 5% emulsion to repel many arthropods and can
be used as a lotion to treat sarcoptic mange and canine pediculosis.
Vorbereitung Methode
BENZYL BENZOATE is produced by the Cannizzaro reaction from benzaldehyde, by esterifying benzyl alcohol with benzoic acid, or by treating sodium benzoate with benzyl chloride. It is purified by distillation and crystallization. Benzyl benzoate is used as a fixative and solvent for musk in perfumes and flavors, as a plasticizer, miticide, and in some external medications. The compound has been found effective in the treatment of scabies and pediculosis capitis (head lice, Pediculus humanus var. capitis).
Allgemeine Beschreibung
Benzyl benzoate is an aromatic ester that is used as a food flavoring agent. It has been identified as one of the main volatile aroma component of cranberry, mango and Egyptian
Jasminum sambac flowers.
Hazard
Irritant to eyes, skin.
Pharmazeutische Anwendungen
Benzyl benzoate is used as a solubilizing agent and nonaqueous
solvent in intramuscular injections at concentrations of
0.01–46.0% v/v, and as a solvent and plasticizer for cellulose
and nitrocellulose. It is also used in the preparation of spray-dried
powders using nanocapsules.
However, the most widespread pharmaceutical use of benzyl
benzoate is as a topical therapeutic agent in the treatment of
scabies. Benzyl benzoate is also used therapeutically as a
parasiticide in veterinary medicine.
Other applications of benzyl benzoate include its use as a
pediculicide, and as a solvent and fixative for flavors and perfumes
in cosmetics and food products.
Kontakt-Allergie
Benzyl benzoate is the ester of benzyl alcohol and
benzoic acid. It is contained in Myroxylon pereirae
and Tolu balsam. It is used in acaricide preparations
against Sarcoptes scabiei or as a pediculicide. Direct
contact may cause skin irritation, but rarely allergic
contact dermatitis. As a fragrance allergen, benzyl
benzoate has to be mentioned by name in EU
cosmetics.
Clinical Use
Benzyl benzoate is a naturally occurring ester obtained fromPeru balsam and other resins. It is also prepared syntheticallyfrom benzyl alcohol and benzoyl chloride. The ester isa clear colorless liquid with a faint aromatic odor. It is insolublein water but soluble in organic solvents.
Benzyl benzoate is an effective scabicide when appliedtopically. Immediate relief from itching probably resultsfrom a local anesthetic effect; however, a complete cureis frequently achieved with a single application of a 25%emulsion of benzyl benzoate in oleic acid, stabilized withtriethanolamine. This preparation has the additionaladvantage of being essentially odorless, nonstaining, andnonirritating to the skin. It is applied topically as a lotionover the entire dampened body, except the face.
Sicherheit(Safety)
Benzyl benzoate is metabolized by rapid hydrolysis to benzoic acid
and benzyl alcohol. Benzyl alcohol is then further metabolized to
hippuric acid, which is excreted in the urine.
Benzyl benzoate is widely used as a 25% v/v topical application
in the treatment of scabies and as an excipient in intramuscular
injections and oral products. Adverse reactions to benzyl benzoate
include skin irritation and hypersensitivity reactions. Oral ingestion
may cause harmful stimulation of the CNS and convulsions. Benzyl
benzoate should be avoided by perople with perfume allergy.
LD
50 (cat, oral): 2.24 g/kg
LD
50 (dog, oral): 22.44 g/kg
LD
50 (guinea pig, oral): 1.0 g/kg
LD
50 (mouse, oral): 1.4 g/kg
LD
50 (rabbit, oral): 1.68 g/kg
LD
50 (rabbit, skin): 4.0 g/kg
LD
50 (rat, oral): 0.5 g/kg
LD
50 (rat, skin): 4.0 g/kg
Environmental Fate
Benzyl benzoate acts as a local irritant. At high levels of exposure,
free benzoic acid may sequester significant amounts of
acetyl coenzyme A (CoA), which could disrupt cholinergic
signaling. Recent findings suggest that benzyl benzoate may
have estrogenic properties.
Stoffwechsel
Benzyl benzoate, a relatively non-toxic liquid widely used for the treatment of scabies, is converted into benzoic acid in vivo (Williams, 1959).
Lager
Benzyl benzoate is stable when stored in tight, well-filled, lightresistant
containers. Exposure to excessive heat (above 408℃)
should be avoided.
Inkompatibilitäten
Benzyl benzoate is incompatible with alkalis and oxidizing agents.
Regulatory Status
Included in the FDA Inactive Ingredients Database (IM injections
and oral capsules). Included, as an active ingredient, in nonparenteral
medicines licensed in the UK. Included in the Canadian List
of Acceptable Non-medicinal Ingredients.
Benzylbenzoat Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
