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2-(2-(4-Methyl-3-cyclohexen-1-yl)propyl)cyclopentanone

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The correct title of this article is 2-[2-(4-Methyl-3-cyclohexen-1-yl)propyl]cyclopentanone. The substitution of any brackets is due to technical restrictions.
2-(2-(4-Methyl-3-cyclohexen-1-yl)propyl)cyclopentanone
Structure of Nectaryl
Structure without shown stereo chemistry
Names
Preferred IUPAC name
2-[2-(4-Methylcyclohex-3-en-1-yl)propyl]cyclopentan-1-one
Other names
methylcyclohexenylpropyl-cyclopentanone (INCI); Nectaryl
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.100.590 Edit this at Wikidata
EC Number
  • 404-240-0
UNII
  • InChI=1S/C15H24O/c1-11-6-8-13(9-7-11)12(2)10-14-4-3-5-15(14)16/h6,12-14H,3-5,7-10H2,1-2H3
    Key: KNHGOYVXAHUDHP-UHFFFAOYSA-N
  • CC1=CCC(CC1)C(C)CC2CCCC2=O
Properties
C15H24O
Molar mass 220.35 g·mol−1
Appearance viscous liquid with fruity odor[1]
Density 0.96 g·cm−3 (22 °C)[1]
Melting point −41.8 °C (−43.2 °F; 231.3 K)[1]
Boiling point 288 °C (550 °F; 561 K)[1]
practically insoluble in water (4.6 mg·l−1 at 20 °C)[1]
Hazards
GHS labelling:
GHS09: Environmental hazard
Warning
H410
P273, P391, P501
Lethal dose or concentration (LD, LC):
5.47 mg·L−1 (zebrafish)
Safety data sheet (SDS) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-[2-(4-Methyl-3-cyclohexen-1-yl)propyl]cyclopentanone (trade name by Givaudan: Nectaryl) is an organic compound belonging to the group of ketones and cycloalkanes. The compound is used as a fragrance.

Synthesis

The synthesis of the compound is carried out by a radical addition of cyclopentanone to (+)-limonene under oxygen in acetic acid. As a catalyst, manganese(II) acetate and cobalt(II) acetate are used.[2]

Properties

The flash point of the compound is 162.5 °C, and the autoignition temperature is 294 °C.[1] The specific rotation is reported to be [α]D20=+228–235° (1 M; chloroform)[2]

In general, the compound features a fruity apricot-like odor. Of the four stereo isomers, (2R,2′S,1′′R)-Nectaryl and (2R,2′R,1′′R)-Nectaryl contribute especially to the compound's odor, the odor detection threshold lies at 0.094 ng·l−1 and 0.112 ng·l−1, respectively. In contrast to that, the other stereo isomers show an unspecific fruity odor, the odor detection threshold are 11.2 ng·l−1 and 14.9 ng·l−1 which is much higher.[2][3]

The tenacity on blotter, the time during which the compound is smellable with unchanged characteristics,[4]: 51  is reported to be three weeks.[4]: 52 

Uses

The substance is used as a fragrance in exemplary air conditioning products, perfumes and polishes.[5]

Literature

  1. ^ a b c d e f g Record of 2-[2-(4-Methyl-3-cyclohexen-1-yl)propylcyclopentanon] in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 3. April 2019.
  2. ^ a b c Elisabetta Brenna; Claudio Fuganti; Francesco G. Gatti; Luciana Malpezzi; Stefano Serra (2008). "Synthesis and olfactory evaluation of all stereoisomers of the fragrance Nectaryl". Tetrahedron: Asymmetry. 19 (7): 800–807. doi:10.1016/j.tetasy.2008.03.011.
  3. ^ John C. Leffingwell. "Chirality & Odour Perception". leffingwell.com. Retrieved 2019-04-03.
  4. ^ a b Wolfgang Legrum (2015). "3". Riechstoffe, zwischen Gestank und Duft (in German) (2 ed.). Springer. pp. 51–52. ISBN 978-3-658-07310-7.
  5. ^ ECHA (ed.). "2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)cyclopentanone". Retrieved 2019-04-03.
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