l-Мускон
l-Muscone is the (-)-enantiomer of muscone, (R)-3-methylcyclopentadecanone, a 15-membered ring ketone and the primary contributor to the odor of deer musk. Its odor is described as musk, animal, powdery.
- Type
- Складник
- Olfactive family
- Амброві й мускусні
- Source
- Synthetic; also found naturally in deer musk
- Chemical class
- macrocyclic ketone
Запах
Докладно
Цікавий факт
Human subjects homozygous for the more sensitive L289F allele of OR5AN1 had a lower detection threshold for muscone and found macrocyclic musks more intense than subjects homozygous for the reference allele. The human receptor OR5AN1 fails to distinguish in vitro between muscone and an isotopolog in which all hydrogen atoms were replaced.
Отримання й хімія
Спосіб отримання
Muscone can be made in the laboratory. One asymmetric synthesis of (-)-muscone begins with commercially available (+)-citronellal and forms the 15-membered ring by ring-closing metathesis. A more recent enantioselective synthesis involves an intramolecular aldol addition/dehydration reaction of a macrocyclic diketone. Another method starts with citronellol; its last two steps use a Grubbs' catalyst to achieve a ring-closure metathesis, followed by a catalytic hydrogenation. Muscone has been synthesized as the pure (-)-enantiomer as well as the racemate. The (R)-form and the (S)-form of optically active muscone can be prepared by asymmetric hydrogenation of 3-methyl-2-cyclopentadecene-1-one, using a ruthenium-optically active phosphine complex as the catalyst. The two forms can also be obtained by preparing the racemic mixture and then using an optical resolution method. In one example, (E)-3-methyl-cyclopentadecene-1-one was hydrogenated with Ru2Cl4[(S)-Tol-BINAP]2NEt3 in methanol and gave optically almost pure (R)-muscone in 95% yield.
- Формула
- C₁₆H₃₀O
- CAS
- 10403-00-6
- Зовнішній вигляд
- oily liquid
- Сила запаху
- Висока
- Стійкість
- Lingers on the skin
- Синоніми
- (R)-3-methylcyclopentadecanone, (3R)-3-methylcyclopentadecan-1-one, (-)-muscone
No IFRA Standard for the material itself (51st Amendment)
- Температура кипіння
- 328 °C
- Температура плавлення
- -15 °C
У парфумерії
As a large molecule, muscone is relatively involatile and lingers on the skin as part of the bottom note of a perfume. It also acts as a fixative, which reduces the evaporation rate of lighter molecules in particular. A fragrance composition and a shampoo containing a 92.5:7.5 (R)-form/(S)-form mixture of optically active muscone gained a natural, rich and fresh muskiness that is excellent in diffusiveness and voluminousness. A fragrance composition and a shampoo containing a 77.5:22.5 (R)-form/(S)-form mixture gained a creamy muskiness with a soft cleanness that leads to whiteness and with excellent powderiness.
Див. також
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