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外観
無色～わずかにうすい黄色, 澄明の液体
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性質
安息香酸ベンジルの融点は17〜20°Cで、沸点は323〜324°Cです。無色またはわずかに薄い黄色の固体または液体です。弱い芳香臭がします。
安息香酸ベンジルは水には溶けません。、、によく溶解します。
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定義
本品は、安息香酸(*)とベンジルアルコール(*)とのエステルであり、次の化学式で表される。
参照表示名称：安息香酸, ベンジルアルコール
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溶解性
水に不溶, エタノール, エーテルに易溶。エタノール及びジエチルエーテルに極めて溶けやすく、水にはほとんど溶けない。
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解説
安息香酸ベンジル (英: Benzyl benzoate) とは、分子式がC14H12O2で表される有機化合物の一種です。
ベンゼンカルボン酸ベンジルや安息香酸フェニルメチルとも呼ばれます。天然に安息香酸ベンジルは、ペルーバルサム (英: Balsam of Peru) やトルーバルサム (英: Tolu balsam) を代表として、多くの花にも存在します。
消防法の危険物第4類第3石油類に該当する、非水溶性の液体です。1日の許容摂取量は0〜5mg/kgですが、香料として使用する場合には安全上の問題は認められていません。
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用途
香料材料(保留剤、溶剤)、可塑剤、医薬原料、有機合成原料。
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構造
安息香酸ベンジルは、ベンジルアルコール (英: benzyl alcohol) と安息香酸 (英: benzoic acid) が脱水縮合した構造を有する有機化合物です。カルボン酸エステルであり、示性式はC6H5CO2CH2C6H5と表されます。分子量は212.24で、密度は1.118g/cm3です。
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合成
図2. 安息香酸ベンジルの合成
安息香酸ベンジルは、のエステル交換によって生成します。と安息香酸ナトリウムの反応でも合成可能です。
酸触媒下でベンジルアルコールと安息香酸を縮合しても、安息香酸ベンジルが得られます。酸を用いてアルコールとカルボン酸からカルボン酸エステルを得る反応は、フィッシャーエステル合成反応 (英: Fischer esterification) と呼ばれます。
ティシチェンコ反応 (英: Tishchenko reaction) を用いても、2分子のベンズアルデヒドから安息香酸ベンジルを合成可能です。ティシチェンコ反応は1906年に初めて、ヴャチェスラフ・ティシチェンコ (英: Vyacheslav Tishchenko) によって報告されました。この反応ではアルコキシドの触媒作用によって、アルデヒド2分子が不均化し、エステル1分子が生じます。
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化粧品の成分用途
忌避剤.殺虫剤、溶剤、香料
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効能
外寄生生物駆除薬
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危険性
安息香酸ベンジルの急性毒性は低いです。すぐに安息香酸とベンジルアルコールに加水分解され、ベンジルアルコールは安息香酸に代謝されます。安息香酸の抱合体は、尿中に急速に排泄されます。ただし安息香酸ベンジルを大量に投与すると、過興奮、協調運動失調、痙攣、呼吸麻痺などの症状を引き起こす場合もあり、注意が必要です。
局所疥癬治療剤として安息香酸ベンジルを使用すると、皮膚炎になる可能性があります。過剰摂取では、アレルギー反応として水ぶくれ、蕁麻疹、発疹を引き起こす場合もあります。
参考文献
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説明
Benzyl benzoate is the ester of benzyl alcohol and benzoic acid, with the formula C6H5CH2O2CC6H5. 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.
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化学的特性
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.
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天然物の起源
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.).
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使用
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.
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適応症
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.
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調製方法
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).
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定義
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.
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定義
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.
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製造方法
By the dry esterification of sodium benzoate and benzoyl chloride in the presence of triethylamine or by reaction of
sodium benzylate on benzaldehyde.
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一般的な説明
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.
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危険性
Irritant to eyes, skin.
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使用用途
安息香酸ベンジルの用途は、「医薬原料」「香料」「有機合成原料」「可塑剤」など、多岐に渡ります。
また、ダニ、シラミ、蚊を駆除するための「殺虫剤」「」などにも使用可能です。ダニによって引き起こされる、強い痒みを伴う疥癬と呼ばれる発疹の治療にも使われています。
そのほか、キャンディやガムなどの「香料」「抗菌防腐剤」にも利用可能です。
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応用例（製薬）
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.
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接触アレルゲン
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.
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臨床応用
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.
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安全性
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.
LD50 (cat, oral): 2.24 g/kg
LD50 (dog, oral): 22.44 g/kg
LD50 (guinea pig, oral): 1.0 g/kg
LD50 (mouse, oral): 1.4 g/kg
LD50 (rabbit, oral): 1.68 g/kg
LD50 (rabbit, skin): 4.0 g/kg
LD50 (rat, oral): 0.5 g/kg
LD50 (rat, skin): 4.0 g/kg
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環境運命予測
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.
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代謝
Benzyl benzoate, a relatively non-toxic liquid widely used for the treatment of scabies, is converted into benzoic acid in vivo (Williams, 1959).
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貯蔵
Benzyl benzoate is stable when stored in tight, well-filled, lightresistant
containers. Exposure to excessive heat (above 408℃)
should be avoided.
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不和合性
Benzyl benzoate is incompatible with alkalis and oxidizing agents.
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規制状況(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.
