5-Cyclohexadecenone

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5-Cyclohexadecenone
Cis-5-cyclohexadecenone.svg
cis-5-cyclohexadecenone
Trans-5-cyclohexadecenone.svg
trans-5-cyclohexadecenone
Names
IUPAC name
Cyclohexadec-5-en-1-one
Other names
5-Cyclohexadecen-1-one; Velvione; musk amberol; Ambrettone; musk TM-II [1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.048.681 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 253-568-9
PubChem CID
UNII
  • InChI=1S/C16H28O/c17-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-16/h6,8H,1-5,7,9-15H2
    Key: ABRIMXGLNHCLIP-UHFFFAOYSA-N
  • C1CCCCCC(=O)CCCC=CCCCC1
Properties
C16H28O
Molar mass 236.399 g·mol−1
AppearanceColorless clear liquid [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5-Cyclohexadecenone is a macrocyclic synthetic musk with the chemical formula C16H28O. It is an unsaturated analog of cyclohexadecanone. It is also similar in chemical structure to the natural musk scents civetone and muscone. [3]

5-Cyclohexadecenone has a strong musk scent [4] with floral, amber, and civet tones. [2] It is used as a substitute for natural musk in perfumes, cosmetics, and soaps. [1] [5] Trade names include Ambretone, [2] Velvione, [4] and TM-II. [5]

5-Cyclohexadecenone can exist as either of two cis/trans isomers and the commercial product is typically a mixture of the two. [5] It can be synthesized in a four-step sequence from cyclododecanone. [6]

Related Research Articles

Perfume is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Perfumes can be defined as substances that emit and diffuse a pleasant and fragrant odor. They consist of manmade mixtures of aromatic chemicals and essential oils. The 1939 Nobel Laureate for Chemistry, Leopold Ružička stated in 1945 that "right from the earliest days of scientific chemistry up to the present time, perfumes have substantially contributed to the development of organic chemistry as regards methods, systematic classification, and theory."

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<span class="mw-page-title-main">Catenane</span> Molecule composed of two or more intertwined rings

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<span class="mw-page-title-main">Civetone</span> Chemical compound

Civetone is a macrocyclic ketone and the main odorous constituent of civet oil. It is a pheromone sourced from the African civet. It has a strong musky odor that becomes pleasant at extreme dilutions. Civetone is closely related to muscone, the principal odoriferous compound found in musk; the structure of both compounds was elucidated by Leopold Ružička. Today, civetone can be synthesized from precursor chemicals found in palm oil.

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<span class="mw-page-title-main">Atrop-abyssomicin C</span> Chemical compound

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References

  1. 1 2 D. McGinty, C. S. Letizia (2011). "Fragrance material review on 5-cyclohexadecen-1-one". Food and Chemical Toxicology. 49 (Supplement 2): S98–S103. doi:10.1016/j.fct.2011.07.033. PMID   21801780.
  2. 1 2 3 "Ambretone" (PDF). takasago.com.
  3. Alvin S. Williams (1999). "The Synthesis of Macrocyclic Musks". Synthesis. 1999 (10): 1707–1723. doi:10.1055/s-1999-3581. S2CID   196729693.
  4. 1 2 "Musk amberol". thegoodscentscompany.com.
  5. 1 2 3 "5-CYCLOHEXADECEN-1-ONE". chemicalbook.com.
  6. Watanabe, Shoji; Suga, Kyoichi; Fujita, Tsutomu; Gomi, Tetsuo (2007-04-25). "Synthesis of 5-cyclohexadecenone from cyclododecanone". Journal of Applied Chemistry and Biotechnology. 23 (7): 501–504. doi:10.1002/jctb.5020230705.