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

2-[2-(4-Methyl-3-cyclohexen-1-yl)propyl]cyclopentanone bracket Nectaryl.svg 250px Structure of Nectaryl Structure without shown stereo chemistry 2-[2-(4-Methylcyclohex-3-en-1-yl)propyl]cyclopentan-1-one methylcyclohexenylpropyl-cyclopentanone (INCI); Nectaryl 95962-14-4 correct CAS correct FDA P1K3Z8A8HJ 404-240-0 175661 153032 3728992 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 KNHGOYVXAHUDHP-UHFFFAOYSA-N CC1=CCC(CC1)C(C)CC2CCCC2=O C15H24O 220.35 g·mol−1 viscous liquid with fruity odor900406 2-[2-(4-Methyl-3-cyclohexen-1-yl)propyl]cyclopentanon 3. April 2019 0.96 g·cm−3 (22 °C) −41.8 288 practically insoluble in water (4.6 mg·l−1 at 20 °C) 5.47 mg·L−1 (zebrafish) 09 Warning 410 273 391 501 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. Properties The flash point of the compound is 162.5 °C, and the autoignition temperature is 294 °C. The specific rotation is reported to be [α]D20=+228–235° (1 M; chloroform) 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.Elisabetta Brenna Claudio Fuganti Francesco G. Gatti Luciana Malpezzi Stefano Serra Synthesis and olfactory evaluation of all stereoisomers of the fragrance Nectaryl Tetrahedron: Asymmetry 19 7 2008 800–807 10.1016/j.tetasy.2008.03.011John C. Leffingwell http://www.leffingwell.com/chirality/nectaryl.htm Chirality & Odour Perception leffingwell.com 2019-04-03 The tenacity on blotter, the time during which the compound is smellable with unchanged characteristics,Wolfgang Legrum Riechstoffe, zwischen Gestank und Duft 2 Springer 2015 978-3-658-07310-7 3 51–52 de g-ndBgAAQBAJ 51 yes51 is reported to be three weeks.52 Uses The substance is used as a fragrance in exemplary air conditioning products, perfumes and polishes.https://echa.europa.eu/de/substance-information/-/substanceinfo/100.100.590 2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)cyclopentanone 2019-04-03 ECHA Literature Category:Cyclohexenes Category:Cyclic ketones Category:Perfume ingredients