Basic information Safety Supplier Related
ChemicalBook >  Product Catalog >  Flavors and fragrances >  Synthetic fragrances >  Macrocyclic musks >  Macrocyclic spices >  Cyclopentadecanone

Cyclopentadecanone

Basic information Safety Supplier Related

Cyclopentadecanone Basic information

Product Name:
Cyclopentadecanone
Synonyms:
  • Cyclopentadecanone, 96% 5GR
  • Normuscon
  • NORMUSCONE
  • OXOCYCLOPENTADECANE
  • MUSK 15
  • CYCLOPENTADECANONE
  • CYCLOPENTADECONE
  • EXALTONE
CAS:
502-72-7
MF:
C15H28O
MW:
224.38
EINECS:
207-951-2
Product Categories:
  • C15 to C38
  • Carbonyl Compounds
  • Ketones
  • Building Blocks
  • C15 to C38
  • Carbonyl Compounds
  • Chemical Synthesis
  • Organic Building Blocks
Mol File:
502-72-7.mol
More
Less

Cyclopentadecanone Chemical Properties

Melting point:
63-65 °C (lit.)
Boiling point:
120 °C/0.3 mmHg (lit.)
Density 
0.897 g/mL at 25 °C (lit.)
vapor pressure 
0.009Pa at 40℃
refractive index 
1.4637 (estimate)
Flash point:
120°C/0.3mm
storage temp. 
Sealed in dry,Room Temperature
solubility 
soluble in Alcohol
form 
powder to crystal
color 
Colourless crystal needles.
Odor
at 10.00 % in dipropylene glycol. powdery musk animal natural greasy
Odor Type
musk
Water Solubility 
578μg/L at 20℃
BRN 
1618444
LogP
5.6 at 20℃
CAS DataBase Reference
502-72-7(CAS DataBase Reference)
NIST Chemistry Reference
Cyclopentadecanone(502-72-7)
EPA Substance Registry System
Cyclopentadecanone (502-72-7)
More
Less

Safety Information

Safety Statements 
22-24/25
WGK Germany 
2
RTECS 
GY0900000
TSCA 
Yes
HS Code 
29142900

MSDS

More
Less

Cyclopentadecanone Usage And Synthesis

Chemical Properties

WHITE CRYSTALLINE POWDER

Chemical Properties

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:

Occurrence

Reported to be found in the scent glands of the Louisiana muskrat Ondatra zibethicus rivalicius (Guenther, 1949).

Uses

Cyclopentadecanone is the main odoriferous component of musk.

Preparation

By the cyclization of dinitriles in high dilution (Bedoukian. 1967).

Synthesis Reference(s)

Chemistry Letters, 7, p. 1283, 1978
The Journal of Organic Chemistry, 36, p. 3266, 1971 DOI: 10.1021/jo00821a003

Toxicity evaluation

Both the acute oral LD50 value in rats and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Moreno. 1975). The acute ip LD100 of cyclopentadecanone was not reached but was estimated to be >35mmol/kg for mice; an ip dose of 11-25 mmol/kg caused no deaths in 24 hr and one of 8-92 mmol/kg caused no deaths in 4 days (the length of the study). An oral dose of ≥45 mmol/kg caused no deaths in mice. Intense agitation accompanied by catatonia of the tail was caused by low doses of cyclopentadecanone; gross examination of the mice revealed no specific pathology but occasionally degenerative hepatitis, proximal tubular nephritis and, rarely, pancreatic necrosis were found following dosing with cycloalkanones (Caujolle & Caujolle, 1965).

Flammability and Explosibility

Non flammable

Metabolism

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).

Purification Methods

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.]

Cyclopentadecanone Preparation Products And Raw materials

Preparation Products

CyclopentadecanoneSupplier

Hubei Hongfuda Biotechnology Co., Ltd. Gold
Tel
027-17340521416 18086404407
Email
2186239902@qq.com
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Email
jkinfo@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Email
market03@meryer.com
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Email
3bsc@sina.com
Alfa Aesar
Tel
400-6106006
Email
saleschina@alfa-asia.com