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Cyclopentadecanone

CAS No.502-72-7
Chemical Name:Cyclopentadecanone
CBNumber:CB2416348
Molecular Formula:C15H28O
Formula Weight:224.38
MOL File:502-72-7.mol

Cyclopentadecanone Property

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)
EWG's Food Scores 1
FDA UNII T09G246LET
NIST Chemistry Reference Cyclopentadecanone(502-72-7)
EPA Substance Registry System Cyclopentadecanone (502-72-7)
UNSPSC Code 12352100
NACRES NA.22

Safety

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

NFPA 704:

	0
1		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Cyclopentadecanone Price More Price(3)

Brand: Sigma-Aldrich(India)
Product number: C111201
Product name : Cyclopentadecanone
Purity: 98%
Packaging: 5G
Price: ₹5141.88
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: C1422
Product name : Cyclopentadecanone
Purity: min. 98.0 %
Packaging: 5G
Price: ₹2400
Updated: 2022/05/26
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Brand: TCI Chemicals (India)
Product number: C1422
Product name : Cyclopentadecanone
Purity: min. 98.0 %
Packaging: 25G
Price: ₹8300
Updated: 2022/05/26
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Cyclopentadecanone Chemical Properties,Usage,Production

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.]