基本情報
- 標準SMILES
CC1CCCCCCCCCCCCC(=O)C1- InChIKey
ALHUZKCOMYUFRB-UHFFFAOYSA-N- 分子式
- C16H30O
- 平均分子量
- 238.41 g/mol
- 単同位体質量
- 238.22966558
名称と識別子
- 優先名称
- Muskone
- IUPAC
- 3-methylcyclopentadecan-1-one
- 現地名
- (3R)-3α-メチルシクロペンタデカノン
- 英語名
- Muscone
- 分子式
- C16H30O
- 分子量
- 238.41
名称と別名
名称をさらに表示
データベース識別子
- CAS
541-91-3- PubChem CID
- 10947
- DTXSID
DTXSID8052192- UNII
- 5JO79R7S9R
- EC Number
- 208-795-8
- Nikkaji
- J276.713I、J489.984I、J6.397E
物性
構造計算による物性
- XLogP
- 6.2
- 極性表面積
- 17.1 Ų
- 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
- 17
- 形式電荷
- 0
- 複雑度
- 198
実験および物理化学的性質
Fragrances
Fragrance Ingredient (3-Methyl-1-cyclopentadecanone) -> IFRA transparency List
Fragrance
Solubility
Very soluble in acetone, ethyl ether, and ethanol
very slightly
Soluble in oils; Slightly soluble in water
Soluble (in ethanol)
Boiling Point
329 °C; 130 °C @ 0.5 mm Hg
Colorless liquids with boiling points that increase regularly with increasing molecular weight. Virtually all members of the series exhibit characteristic odor depending on the ring size. /Cycloaliphatic ketones/
320.00 to 329.00 °C. @ 760.00 mm Hg
Physical Description
Liquid
Clear viscous oil with pleasant musky fragrance; [MSDSonline]
Colourless or opaque crystalline mass; Soft, sweet, tenacious musk aroma
物理化学的性質
- 融点
- -15 °C · -15°C(lit.)
- 沸点
- 95 °C/0.1mmHg · 95°C/0.1mmHg(lit.)
- 比重(密度)
- 0.9221 · 0.9221
- 蒸気圧
- 0.041 Pa · 0.041Pa at 25℃
- FEMA
- 3434 · 3434 | 3-METHYL-1-CYCLOPENTADECANONE
- 屈折率
- 1.477 to · 1.4770 to 1.4810
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- クロロホルム、メタノール(少量)
- 外見
- 無色油。
- 色
- 無色
- 臭い (Odor)
- 10 %。甘いムスク動物パウダリー脂肪ナチュラル · ジプロピレングリコール中10.00%。甘いムスク動物パウダリー脂肪ナチュラル
- においのタイプ
- ムスク
- 由来生物
- mouse
- 水溶解度
- 430 μg/L · 430μg/L at 20℃
- Merck
- 14 · 14,6313
- JECFA Number
- 1402 · 1402
- 主な用途
- 食品および飲料
- 化粧品成分の機能
- 香料
- InChI
- 1S/C16H30O/c1-15-12-10-8-6-4-2-3-5-7-9-11-13-16(17)14-15/h15H,2-14H2,1H3
- InChIKey
- ALHUZKCOMYUFRB-UHFFFAOYSA-N
- SMILES
- O=C1CC(CCCCCCCCCCCC1)C
- LogP
- 6.06 at · 6.06 at 25℃
- CAS データベース
- 541 · 541-91-3(CAS DataBase Reference)
- NISTの化学物質情報
- 3 · Cyclopentadecanone, 3-methyl-(541-91-3)
- EPAの化学物質情報
- 3 · Cyclopentadecanone, 3-methyl- (541-91-3)
化学的性質
化学的特性Muscone is an odoriferous constituent of natural musk. It is a colorless liquid with very soft, sweet, musky odor and a perfumery, animal tonality.Numerous syntheses have been developed for its preparation including enantioselective methods to obtain the naturally occurring (3R)-enantiomer (l-muscone,. Because of its excellent stability, it can be used in awide range of products to give elegant,warm, animal notes. It is important for the reconstitution of naturalmusk.
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 99.7% (1559 of 1564) of all reports.
Not Classified
Aggregated GHS information provided per 1564 reports by companies from 5 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Information
Chemical: Cyclopentadecanone, 3-methyl-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Cyclopentadecanone, 3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclopentadecanone, 3-methyl- 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: 01-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18970
Cyclopentadecanone, 3-methyl-: Does not have an individual approval but may be used under an appropriate group standard
FDA Requirements
Musk used as spices, seasonings, essential oils, oleoresins, and natural extracts in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice. /Musk/
Certain other spices, seasonings, essential oils, oleoresins, and natural extracts that are generally recognized as safe for their intended use, within the meaning of section 409 of the act. Musk is included on this list. /Musk/
安全と保護具
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
毒性情報
Natural Pollution Sources
THE SECRETION IS FOUND IN AN INTERNAL POUCH LOCATED UNDER THE SKIN OF THE ABDOMEN OF THE.../MUSK DEER/. THE MUSK POUCHES ARE REMOVED FROM THE ANIMAL & SUBSEQUENTLY DRIED, THUS CAUSING THE HARDENING & DARKENING OF THE SECRETION (SO-CALLED MUSK GRAINS) WITHIN THE POUCH. /MUSK/
Natural sources of musk incl musk glands of male musk deer, Moschus moschiferus, civet cat, Viverra civetta, louisiana muskrat, ambrette seeds, Abelmoschus moschatus, and angelica roots, Angelica archangelica. /musks/
Non-Human Toxicity Excerpts
In the present study, we investigated the effects of muscone on both in vitro and in vivo parameters of the hepatic microsomal drug-metabolizing enzyme system and other enzyme activities in rats. In the in vivo study, the serum dimethadione (DMO)/trimethadione (TMO) ratios at 2 hr after oral administration of trimethadione (100 mg/kg) were significantly increased in both male and female rats treated with 75 and 150 but not 40 mg muscone/kg. Antipyrine metabolite profile in 24 hr urine of rats pretreated with muscone (150 mg/kg) was examined. The results showed that the excretion of norantipyrine was significantly increased as compared to the control group. In the in vitro study, we found that the content of cytochrome p450, and activities of aminopyrine, N-demethylase, aniline hydroxylase and delta-aminolevulinic acid (ALA) synthetase were significantly increased as compared to the controls in both male and female rats treated with muscone (75 and 150 mg/kg). This type of induction of the hepatic metabolizing enzymes was similar to that seen after treatment with a prototype drug, phenobarbital.
法規制情報
FDA Requirements
Musk used as spices, seasonings, essential oils, oleoresins, and natural extracts in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice. /Musk/
Certain other spices, seasonings, essential oils, oleoresins, and natural extracts that are generally recognized as safe for their intended use, within the meaning of section 409 of the act. Musk is included on this list. /Musk/
安全データ
- wgk
- WGK 3
- tsca
- TSCA listed
- hs_code
- 2914.29.5000
- 化審法
- (3)-4630
- 消防法
- 危-4-3-III
- ストレージクラス
- 10 - Combustible liquids
- 有毒物質データの
- 541-91-3(Hazardous Substances Data)
化学と産業
薬理情報
用途と製造
Uses
Fragrant component of musk; [Merck Index] Used in perfumes and as a flavor ingredient; [HSDB]
FLAVOR INGREDIENT /DL-FORM/
Used in perfumes over a wide range of concns /Aroma chemicals/
Methods of Manufacturing
INFUSIONS & TINCTURES...PREPD BY ALCOHOLIC EXTRACTION OF MUSK GRAINS. BY CONCENTRATING ALCOHOLIC EXTRACTS...POSSIBLE TO PREPARE A "MUSK RESINOID." TRUE RESINOID IS PREPD BY PETROLEUM ETHER EXTRACTION OF MUSK GRAINS. MUSK ABSOLUTE IS PREPARED BY ALCOHOLIC EXTRACTION FROM RESINOID. /MUSK/
Synthesis of the +/- form: Ziegler, Weber, Ann 512, 164 (1934); Ruzicka, Stoll, Helv Chim Acta 17, 1308 (1934); Hunsdiecker, Ber 75B, 1197 (1942). Recent syntheses: Stork, McDonald, J Am Chem Soc 97, 1264 (1975): H.G. Fliri et al, Monatch Chem 110, 245 (1979); C. Fehr et al., Helv Chim Acta 62, 2655 (1979); K. H. Schulte-Elte et al., ibid 2673; G. Cantoni et al., J Org Chem 45, 1906 (1980).
(Natural) Secretion from preputial follicles of the musk deer. (Synthetic) (1) Ketones and lactones with 15- or 16-carbon rings, structurally resembling the odiferous principles of matural musk, civet, and musky-type plants. Among these are ambrettolide, civetone, muscone, exatolide. (2) Nitrated compounds, usually nitrated tert-butyl-toluenes or xylenes or related compounds.
FROM THE CONDENSATION OF DODECAMETHYLENE-ALPHA,OMEGA-DIMETHYLKETONE HEXADECANE... NATURAL OCCURRENCE: IN NATURAL MUSK. REGULATORY STATUS: FEMA NUMBER 3434. /DL-FORM/
Formulations/Preparations
THE DRIED, UNOPENED POUCHES OF COMMERCE ARE DISTINGUISHED BY THE FOLLOWING NAMES: TONQUIN, BLUE SKIN, YUNNANN, SAWKO, CABARDIN, NEPAL, & ASSAM. GOOD QUALITY POUCHES CONTAIN APPROX 70% MUSK, WHILE LESS VALUABLE ONES CONTAIN AS LITTLE AS 40% MUSK. /MUSK/
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Cyclopentadecanone, 3-methyl-: ACTIVE
/MUSK CONSISTS/...OF A GLANDULAR SECRETION OF THE /ADULT/ MALE MUSK DEER OF TIBET, SOUTHERN CHINA, NORTHERN INDIA, & THROUGHOUT THE HIMALAYAN HIGHLANDS. SECRETION...IS A REDDISH-BROWN, PASTE-LIKE MASS WITH A VERY STRONG, PENETRATING ODOR. /MUSK/
Natural musks are macrocyclic ketones or lactones having approx 15 carbons in their ring structures. Synthetic musks are of greater industrial importance and incl nitro and non-nitro benzenes, indans, and tetralins; derivatives of hydrindacene, isochroman, naphthindan, and coumarin. /Musks/
The three most commonly used in perfumery are musk ambrette, musk ketone, and musk xylene. /Synthetic musk/
... Due to the many steps involved and poor yields, /syntheses/ are not widely used on an industrial scale.
For more General Manufacturing Information (Complete) data for MUSKONE (7 total), please visit the HSDB record page.
応用分野
解説ムスコン,中央アジア,とくにヒマラヤの山岳地方に生息するジャコウジカの雌の生殖分泌腺から分泌されるムスク(musk)の香気成分.十五員環ケトンで光学活性.融点33 ℃,沸点328 ℃,138 ℃(66 Pa).[α]D -13°.d174 0.9221.n17D 1.4802.保香性がよく,香料に用いられる.合成品もある.LD50 5000 mg/kg(ラット,経口).天然じゃ香の香気の本体として0.5~2%含まれる。アルコールに溶けるが、水には難溶。調合香料の製造に際して香料の保留力が著しく、高級香料の変調剤、保留剤として使われる。
天然物の起源Reported found in natural musk
使用Muscone protects PC12 cells against glutamate-induced apoptosis.
調製方法
製造方法From condensation of dodecamethyl-ene-α,ω-dimethylketone hexadecane.
上流・下流製品情報
上流原料
サプライヤー50 社
関連反応
関連ノート
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