Дигідромірценол
Dihydromyrcenol is a synthetic organic compound used mainly as a fragrance ingredient. Its odour is fresh, with a lime-like and citrus-like character.
- Type
- Складник
- Olfactive family
- Цитрусові
- Source
- synthetic molecule
- Chemical class
- Tertiary alcohol
Запах
Докладно
Цікавий факт
Worldwide use of dihydromyrcenol exceeded 1000 metric tons per year as of 2004. Although it resembles natural monoterpene compounds such as myrcenol, it has not been reported to be found in nature. In lists of odour uses it appears as a replacer for fir needle oil and for palmarosa oil.
Отримання й хімія
Спосіб отримання
Dihydromyrcenol is a synthetic organic compound. It can be obtained by hydroxylation from citronellene, a pyrolysis product of cis-pinane. In a patented process, α-pinene is first hydrogenated to α-pinane, which is then pyrolysed to a mixture of hydrocarbons. The pyrolysis runs at 400 to 700 °C, preferably at 550 to 650 °C. The hydrocarbon mixture is reacted with hydrogen chloride in the presence of a Lewis acid or protonic acid catalyst to give a mixture of tertiary chlorides. Hydroxylating these chlorides with water and a catalyst gives dihydromyrcenol as the only tertiary alcohol formed. The other products are hydrocarbons that are easily separated. The dihydromyrcenol is then distilled easily from the reaction mass. Using acetic acid instead of water in the last step gives dihydromyrcenyl acetate instead. In the worked example of the patent, 1000 g of α-pinene was hydrogenated with 1.0% by weight of a commercial nickel catalyst at 100 to 200 °C under 50 to 80 psig, with one mole of hydrogen per mole of α-pinene. The α-pinane obtained was vaporised and passed through a copper tube at 600 to 620 °C. The crude product is distilled on a multiplate column, preferably of 5 to 10 plates.
- Формула
- C₁₀H₂₀O
- CAS
- 18479-58-8
- Зовнішній вигляд
- Colorless clear liquid
- Сила запаху
- Середня
- Стійкість
- 16 hours
- Синоніми
- Dihydro myrcenol
No IFRA Standard for the material itself (51st Amendment)
- Температура кипіння
- 194–197°C at 760 mmHg
- Температура спалаху
- 76°C (169°F)
- Відносна густина
- 0.831–0.839 at 20°C
- Показник заломлення
- 1.434–1.440 at 20°C
У парфумерії
Dihydromyrcenol is used extensively in the fragrance industry. It blends well with isocyclocitral and acts as a lime replacer. A synthetic odorant with a metallic citric-floral character, it is typical of fougère family fragrances. In one aromatic fougère whose top notes are bergamot, rosemary and lavender, the top note includes a prominent amount of it. A rose accord formula uses it at 0.01 part beside benzyl propionate, linalyl acetate and phenethyl alcohol, each at 0.05 part. Its listed potential uses include citrus, cologne, fresh and clean, lime and ocean-sea compositions. It is also recorded as a flavouring compound, with a taste described as green, aldehydic, herbal, terpenic, soapy, lime and tropical.
Див. також
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