502-72-7 Usage
Description
Cyclopentadecanone is a white crystalline powder that is a musk fragrance found in the scent glands of the male civet cat and the Louisiana muskrat Ondatra zibethicus rivalicius. It is the main odoriferous component of musk and has been synthesized through various methods, with the Story procedure being the most promising for large-scale production.
Uses
Used in Fragrance Industry:
Cyclopentadecanone is used as a key ingredient in the creation of fine fragrances, providing a distinct musk scent that is highly valued in the perfume industry.
Used in Musk Scent Production:
Cyclopentadecanone is used as the main odoriferous component in the production of musk scents, which are widely used in the perfumery and fragrance industries for their unique and long-lasting aroma.
Used in Synthetic Musk Creation:
Due to its musk fragrance properties, Cyclopentadecanone is used in the development of synthetic musk compounds, which are often utilized as substitutes for natural musk in various applications to reduce the impact on wildlife and the environment.
Used in Biotechnological Processes:
Cyclopentadecanone may also be produced through biotechnological processes involving long-chained aliphatic dicarboxylic acids, which could potentially offer a more sustainable and environmentally friendly route for its production.
Preparation
By the cyclization of dinitriles in high dilution (Bedoukian. 1967).
Synthesis Reference(s)
Chemistry Letters, 7, p. 1283, 1978The 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
Nonflammable
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 502-72-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 2 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 502-72:
(5*5)+(4*0)+(3*2)+(2*7)+(1*2)=47
47 % 10 = 7
So 502-72-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H28O/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-15/h1-14H2
502-72-7Relevant articles and documents
Synthesis of Cyclopentadecanone by Ring Contraction of Cyclohexadecanone
Kato, Tetsuya,Kondo, Hisao,Miyake, Akihisa
, p. 823 - 824 (1980)
Cyclopentadecanone has been synthesized from cyclohexadecanone. 2,2,15-Tribromocyclohexadecanone, upon treatment with sodium methoxide, underwant the Favorskii rearrangement via methyl 2-bromo-1-cyclopentadecene-1-carboxylate to produce a mixture of methyl 2-methoxy-1-cyclopentadecene-1-carboxylate, methyl 2-methoxy-2-cyclopentadecene-1-carboxylate, and methyl 2,2-dimethoxycyclopentadecane-1-carboxylate which was converted into cyclopentadecanone.
Cyclopentadecanone preparation method
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, (2018/04/28)
The invention provides a cyclopentadecanone preparation method. The method includes that cyclododecene and acryloyl chloride are subjected to reaction to obtain a ketene intermediate shown as a formula (II), the intermediate and a sulfuryl hydrazine compound are subjected to reaction to obtain a hydrazone intermediate shown as a formula (III), and the hydrazone intermediate is subjected to ring opening and hydrogenation to obtain a cyclopentadecanone product shown as a formula (V). Compared with a traditional cyclopentadecanone synthesis route, the method mainly has advantages of low cost andeasiness in acquisition of starting materials, the ketene intermediate shown as the formula (II) is obtained by high-selectivity reaction of cyclododecene and acryloyl chloride, and the integral synthesis route is simple and short in step, high in total yield and applicable to cyclopentadecanone industrial production.
CIRCULAR ECONOMY METHODS OF PREPARING UNSATURATED COMPOUNDS
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Paragraph 0064, (2018/01/18)
Methods of preparing unsaturated compounds or analogs through dehydrogenation of corresponding saturated compounds and/or hydrogenation of aromatic compounds are disclosed.