Бензилбензоат

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Базові ноти
Визначення

Benzyl benzoate is the ester of benzyl alcohol and benzoic acid. It has a faint, sweet, balsamic odour.

СОЛОДКИЙ БАЛЬЗАМІЧНИЙ
Benzoic acid benzyl ester, Ascabin, Ascabiol, Phenylmethyl benzoate, Benzyl benzenecarboxylate
Type
Складник
Olfactive family
Смолисті
Source
Produced industrially; also present in Balsam of Peru, Tolu balsam and a number of flowers
Chemical class
ester (benzoate)
Інструменти
Піраміда
ВВерхні ноти
СНоти серця
ББазові ноти
2/5Сила
Низька
інтенсивність запаху
Країни-виробники
Сполучені Штати

Запах

Benzyl benzoate has a weak, sweet-balsamic odor. Its aroma is described as mildly sweet, balsamic, oily, herbal, floral, and fruity. Another description gives a light, balsamic odor reminiscent of almond. A faint, pleasant, aromatic odor is also reported.

Докладно

Chemistry

Its condensed formula is C₆H₅COOCH₂C₆H₅, and it is classed as both a benzoate ester and a benzyl ester. It forms either a colorless viscous liquid or white solid flakes. Benzyl benzoate is insoluble in water but miscible with alcohol, chloroform, ether and oils. It congeals at temperatures not below 18 °C and supercools easily. It has low acute toxicity in laboratory animals and is rapidly hydrolyzed to benzoic acid and benzyl alcohol.

Occurrence

Benzyl benzoate occurs in a number of blossoms, for example tuberose and hyacinth, and is a component of Balsam of Peru and Tolu balsam. Balsam of Peru contains 25 or so different substances, including cinnamein, cinnamic acid, cinnamyl cinnamate, benzyl benzoate, benzoic acid, and vanillin. The bulk of Peru balsam oil consists of a mixture of the benzyl esters of cinnamic and benzoic acids. Benzyl benzoate has been isolated from plant species of the genus Polyalthia.

Production volume

United States production in 2023 was in the range of 10,000,000 to under 25,000,000 pounds.

Uses beyond perfumery

Benzyl benzoate is used as a medication and insect repellent. As a medication it is used to treat scabies and lice. It is also used as a dye carrier, a solvent for cellulose derivatives and a plasticizer. A moist powder of wetted cellulose and benzyl benzoate is used on carpets as an acaricide.

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Related: Amberwood · Andiroba · Bakhoor · Balsamic Notes · Benzoin Resinoid · Benzyl Salicylate · Birch Tar · Blue Amber

Цікавий факт

Benzyl benzoate is lethal to Sarcoptes scabiei, the mite that causes scabies. The World Health Organization's List of Essential Medicines includes it as a 25% topical lotion.

Отримання й хімія

Спосіб отримання

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

Формула
C₁₄H₁₂O₂
CAS
120-51-4
Зовнішній вигляд
Colorless oily liquid or white solid
Сила запаху
Слабка
Синоніми
Benzoic acid benzyl ester, Ascabin, Ascabiol, Phenylmethyl benzoate, Benzyl benzenecarboxylate
Статус IFRA
Обмежено

Restricted — IFRA Standard « Benzyl benzoate » (Amendment 49)

Фізичні властивості
Температура кипіння
323-324 °C
Температура плавлення
21 °C
Температура спалаху
316 °F (158 °C), closed cup
Відносна густина
1.116-1.120 at 25 °C/25 °C
Показник заломлення
1.5680 at 20 °C

У парфумерії

Benzyl benzoate is used as a fixative in the perfume industry. It is a fragrance allergen that must be declared on the label of a cosmetic product when present above 0.001% in leave-on products or above 0.01% in rinse-off products.

Роль у формулі
01фіксатор
02сполучний компонент
Форми випуску
натуральний екстракт синтетична речовина

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