Georgywood

СинтетичнийПОПУЛЯРНІ Й НЕЗВИЧНІдеревний · амбровий · квітковий
Базові нотиПіраміда
—Сила
—Стійкість
—Походження

Редакційна приміткаМи не маємо жодних прав на цей матеріал, його назву чи торговельну марку. Ця стаття глосарію є незалежною редакційною журналістикою й опублікована на підставі свободи вираження поглядів.

Зразок
Georgywood як парфумерна сировина
Базові ноти
Визначення

Georgywood is a woody fragrance molecule, a component of the Iso E Super mixture, named after Georg Fráter. Its odour type is woody.

ПРЯНИЙ СОЛОДКИЙ АМБРОВИЙ ТЕПЛИЙ ВЕРШКОВИЙ
Type
Складник
Olfactive family
Деревні
Source
Synthetic
Chemical class
Ketone
Інструменти
Піраміда
ВВерхні ноти
СНоти серця
ББазові ноти

Запах

Georgywood has a woody, amber and floral odour at 1.00 % in dipropylene glycol. The (-) enantiomer is woody-ambery, with a fresh, minty, green and sweet bottom note. The (+) enantiomer is weakly woody, with an unpleasant, acrid and musty bottom note. Several members of the Corey group described the weak odour of the (+) enantiomer as distinctly unpleasant and acrid-musty.

Докладно

Georgywood is named after Georg Fráter. It was patented as the second impurity of Iso E Super. For comparison, Iso E Super Plus, an impurity of about 5% in the mixture, has an odour threshold as low as 5 ng/L, and Iso E Super itself has 500 ng/L.

Chemistry

Georgywood has the formula C16H26O and a molecular weight of 234.38. The IUPAC name of the compound is 1-[(1R,2S)-1,2,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl]ethanone. The isomer β-Georgywood is cis-2-acetyl-1,2,3,4,5,6,7,8-octahydro-1,2,8,8-tetramethylnaphthalene. β-Georgywood is the olfactorily most potent isomer of the commercialized fragrance mixture known as Georgywood. Of its two enantiomers, one has the stronger fragrance, but the mixture of both also has valuable properties. An X-ray structure was obtained from the oxime derivative of (-)-(1R,2S)-Georgywood.

Industrial Context

None of the industrial syntheses of the compounds related to Iso E Super is very stereo- and regioselective, so these compounds are handled as varying mixtures rather than as single isomers. Industrial production has so far been directed towards product mixtures dominated by one isomer with favourable olfactory properties. In the Lewis-acid process, iso-Georgywood may be present at about 1 to 5% by weight, but it is generally completely absent.

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Related: Almond Tree · Ambrox Super · Amburana Wood · Amyris · Blonde Woods · Caoutchouc · Cashalox · Cashmir Wood

Цікавий факт

A Lewis-acid cyclisation process makes Georgywood mixtures that contain at least 70%, preferably 85 to 95%, of the isomer β-Georgywood. That proportion is much higher than was previously possible.

Отримання й хімія

Спосіб отримання

Georgywood is produced industrially with, for example, methanol as an additive to enforce isomerisation and suppress premature cyclisation. The isomer β-Georgywood can be prepared by cyclisation of Ψ-Georgywood with a Brønsted acid such as H3PO4. This route also gives the undesirable iso-Georgywood, which cannot be converted to β-Georgywood. Cyclisation of Ψ-Georgywood with more than one molar equivalent of a Lewis acid gives a mixture of β-Georgywood, Georgywood-enolether and γ-Georgywood. Lewis acids such as AlCl3 shift the equilibrium towards Georgywood type products, especially when used in over-stoichiometric amounts.

Формула
C₁₆H₂₆O
CAS
185429-83-8
Зовнішній вигляд
Colorless liquid
Статус IFRA
Див. примітку

No IFRA Standard for the material itself (51st Amendment)

У парфумерії

Georgywood is commercialized as a fragrance mixture, in which β-Georgywood is the olfactorily most potent isomer.

Роль у формулі
01фіксатор
02модифікатор
03кістяк
04фірмова нота
Форми випуску
стандартна форма

Див. також

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