シクロペンタデカノン
シクロペンタデカノン · ケトシクロペンタデカン · エキサルトン · ノルムスコン · シクロペンタデカン-1-オン · EXALTONE · MUSK 15 · exalton
識別子と物理属性
| CAS No. | 502-72-7 |
|---|---|
| 分子式 | C15H28O |
| 平均分子量 | 224.38 g/mol |
| 単同位体質量 | 224.21401552 g/mol |
| SMILES | O=C1CCCCCCCCCCCCCC1 |
| InChIKey | OSOIQJGOYGSIMF-UHFFFAOYSA-N |
| PubChem CID | 10409 |
| ChEMBL | CHEMBL3188770 |
| EC No. | 207-951-2 |
| DTXSID | DTXSID2047141 |
| 現地名 | シクロペンタデカノン |
化学・物理的性質
| XLogP | 5.8 |
|---|---|
| 極性表面積 | 17.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 16 |
| 形式電荷 | 0 |
| 複雑度 | 156 |
| SpringerMaterials Properties | Optical coefficient |
| 香料 | Fragrance Ingredient (Cyclopentadecanone) -> IFRA transparency List |
| Physical Description | Liquid |
| 融点 | 63-65 °C (lit.) |
| 沸点 | 120 °C/0.3 mmHg (lit.) |
| 密度 | 0.897 g/mL at 25 °C (lit.) |
| 蒸気圧 | 0.009Pa at 40℃ |
| 屈折率 | 1.4637 (estimate) |
| 引火点 | 120°C/0.3mm |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 溶解度 | soluble in Alcohol578μg/L at 20℃ |
| 外観・状態 | powder to crystal |
| 色 | 無色の水晶針。 |
| 臭い | ジプロピレングリコール中10.00%。パウダリー ムスク 動物 天然 脂っこい |
| においのタイプ | ムスク |
| BRN | 1618444 |
| 化粧品成分の機能 | デオドラント香料 |
| InChI | 1S/C15H28O/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-15/h1-14H2 |
| InChIKey | OSOIQJGOYGSIMF-UHFFFAOYSA-N |
| SMILES | O=C1CCCCCCCCCCCCCC1 |
| LogP（分配係数） | 5.6 at 20℃ |
| CAS データベース | 502-72-7(CAS DataBase Reference) |
| NISTの化学物質情報 | Cyclopentadecanone(502-72-7) |
| EPAの化学物質情報 | Cyclopentadecanone (502-72-7) |
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：
化学性质
持続性のある強いムスク香
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 96.2% (1372 of 1426) of all reports.Not ClassifiedAggregated GHS information provided per 1426 reports by companies from 5 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Chemical: CyclopentadecanoneCyclopentadecanone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclopentadecanone are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 08-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24075Cyclopentadecanone: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | Evaluation - Exaltone and related macrocyclic musks |
| Hazard Classes and Categories | Not Classified |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | GY0900000 |
| 税関コード | 29142900 |
| 化審法 | (3)-3307 |
| 安全措置（S） | 22-24/25 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
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）
天然物の起源
Reported to be found in the scent glands of the Louisiana muskrat Ondatra zibethicus rivalicius (Guenther, 1949).
使用
Cyclopentadecanone is the main odoriferous component of musk.
製法・合成法
製造方法
By the cyclization of dinitriles in high dilution (Bedoukian. 1967).
合成方法
大環状ムスク
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.]