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外観
白色～ほとんど白色粉末～結晶
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解説
C15H28O(224.39)．ノルムスコンともいう．シクロペンタデカノン, 雄のジャコウ猫のジャコウ腺から分泌される香気性化合物．合成法が多数報告されているが，たとえば，ヘキサデカンジカルボン酸ナトリウム塩を減圧下で加熱乾留すると得られる．融点65～66 ℃，沸点142～144 ℃(400 Pa)．d66"0.897．n66"1.464．3-メチルシクロペンタデカノンであるムスコンとよく似た香気を有し，ともに高級香料に利用される．森北出版「化学辞典（第2版）
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化学的特性
Cyclopentadecanone is a musk fragrance found in the
scent gland of the male civet cat.
A number of syntheses have been developed for its manufacture [260]. Among
these, the so-called Story procedure is the only route that has the potential to
make cyclopentadecanone available on a larger scale, but due to the handling of
hydroperoxides, the process is difficult to manage.
The process starts from tricyclohexylidene triperoxide, which is obtained by
oxidation of cyclohexanone with hydrogen peroxide. Pyrolysis leads to a mixture
of 1,16-hexadecanolide and cyclopentadecane. The latter is oxidized by oxygen
under boric acid catalysis to cyclopentadecanol, which is subsequently oxidized
to cyclopentadecanone.
Due to the availability of long-chained aliphatic dicarboxylic acids by biotechnological
processes, a Dieckmann condensation reaction may also possibly
be a useful route to produce this macrocyclic ketone.
Cyclopentadecanone is used in fine fragrances：
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天然物の起源
Reported to be found in the scent glands of the Louisiana muskrat Ondatra zibethicus rivalicius (Guenther, 1949).
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使用
Cyclopentadecanone is the main odoriferous component of musk.
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製造方法
By the cyclization of dinitriles in high dilution (Bedoukian. 1967).
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代謝
Ketones are not readily metabolized, although most of them probably undergo appreciable reduction to the corresponding secondary alcohols, which are excreted in the urine as glucuronic acid conjugates (Williams, 1959). Cyclopentadecanone was hydroxylated in cultures of four steroid-hydroxylating fungi (Calonectria decora, Rhizopus nigricans, Daedalea rufescens and Ophiobolus herpotrichus), but was not affected by Aspergillus ochraceus. Initial attack occurred at the most remote carbon atom, with yields of up to 26% of 8-hydroxycyclopentadecanone, plus dihydroxy compounds and more polar products (Ashton, Bailey & Jones, 1974).
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純化方法
Subliming Exaltone is better than crystallising it from aqueous EtOH for purification. The semicarbazone has m 186-187o. [Stevens & Erickson J Am Chem Soc 64 146 1942, Mathur et al. J Chem Soc 3505 1963, Biens & Hess Helv Chim Acta 71 1704 1988, Beilstein 7 III 203, 7 IV 118.]
