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

The correct title of this article is " 2- [2- (4-Methyl-3-cyclohexen-1-yl) propyl] cyclopentanone ". This notation is not possible in Wikipedia due to technical restrictions .

Structural formula
Figure without stereochemistry
General
Surname	2- [2- (4-methyl-3-cyclohexen-1-yl) propyl] cyclopentanone ( IUPAC )
other names	METHYLCYCLOHEXENYLPROPYL-CYCLOPENTANONE ( INCI )
Molecular formula	C 15 H 24 O
Brief description	viscous liquid with a fruity odor
External identifiers / databases
CAS number 95962-14-4 EC number 404-240-0 ECHA InfoCard 100.100.590 PubChem 175661 ChemSpider 153032 Wikidata Q62736035
properties
Molar mass	220.35 g mol −1
Physical state	liquid
density	0.96 g cm −3 (22 ° C)
Melting point	−41.8 ° C
boiling point	288 ° C
Vapor pressure	16.13 hPa (20 ° C)
solubility	practically insoluble in water (4.6 mg l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 410 P: 273-391-501
Toxicological data	5.47 mg L −1 ( LC 50 ,  zebrafish , 96 h ) 0.49 mg L −1 ( EC 50 ,  water flea , 48 h )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2- [2- (4-Methyl-3-cyclohexen-1-yl) propyl] cyclopentanone ( trade name of Givaudan : Nectaryl ) is an organic compound from the group of ketones and cycloalkenes . The compound is used as an odorant .

presentation

The compound is prepared by the radical addition of cyclopentanone to (+) - limonene under an oxygen atmosphere in acetic acid . As catalysts are manganese (II) acetate and cobalt (II) acetate used.

properties

The flash point of the compound is 162.5 ° C, the ignition temperature is 294 ° C. The specific angle of rotation is given as [α] _D ²⁰  = + 228-235 ° (1  M ; chloroform ).

The compound generally has a fruity, apricot-like odor. Of the four stereoisomers , (2 R , 2 ' S , 1' ' R ) -nectaryl and (2 R , 2' R , 1 '' R ) -nectaryl contribute to the odor of the compound, the odor threshold is 0.094 ng · L ⁻¹ or 0.112 ng · l ⁻¹ . In contrast to this, the other stereoisomers have an unspecific, fruity odor; the odor thresholds are significantly higher at 11.2 ng · l ⁻¹ and 14.9 ng · l ⁻¹ .

The tenacity on blotter (in German roughly: time spent on blotting paper ; the time during which the substance can be smelled with unchanged characteristics) is given as three weeks.

use

The substance is used as an odorous substance, for example in air care products, perfumes and polishes.

Individual evidence

1. ↑ ^{a b c d e f g h i} Entry on 2- [2- (4-methyl-3-cyclohexen-1-yl) propyl] cyclopentanone in the GESTIS substance database of the IFA , accessed on April 3, 2019 (JavaScript required)
2. ↑ ^{a b} Product Specification. (PDF) Nectaryl. Vigon, p. 8 , accessed on March 14, 2019 . 
3. ↑ ^{a b c} Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Luciana Malpezzi, Stefano Serra: Synthesis and olfactory evaluation of all stereoisomers of the fragrance Nectaryl . In: Tetrahedron: Asymmetry . tape 19 , no. 7 , April 2008, p. 800-807 , doi : 10.1016 / j.tetasy.2008.03.011 .
4. ^ John C. Leffingwell: Chirality & Odor Perception. The Nectaryls. In: leffingwell.com. Retrieved April 3, 2019 . 
5. ↑ Wolfgang Legrum: Fragrances, between stench and fragrance . 2nd Edition. Springer, 2015, ISBN 978-3-658-07310-7 , chap. 3 , p. 51 .
6. ↑ Wolfgang Legrum: Fragrances, between stench and fragrance . 2nd Edition. Springer, 2015, ISBN 978-3-658-07310-7 , chap. 3 , p. 52 ( limited preview in Google Book Search [accessed April 3, 2019]).
7. ↑ InfoCard for 2- (2- (4-methyl-3-cyclohexen-1-yl) propyl) cyclopentanone from the European Chemicals Agency (ECHA), accessed on April 3, 2019.