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

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

CAS Number

* 95962-14-4 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL3728992

ChemSpider |

* 153032

EC Number |

* 404-240-0

PubChem CID

* 175661

UNII |

* P1K3Z8A8HJ Y

InChI

* 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

SMILES

* CC1=CCC(CC1)C(C)CC2CCCC2=O

Properties

Chemical formula

| 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]

Solubility in water

| practically insoluble in water (4.6 mg·l−1 at 20 °C)[1]
Hazards
Safety data sheet | [1]
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H410

GHS precautionary statements

| P273, P391, P501
Lethal dose or concentration (LD, LC):

LC50 (median concentration)

| 5.47 mg·L−1 (zebrafish)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

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.

## Contents

* 1 Synthesis
* 2 Properties
* 3 Uses
* 4 Literature

## 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. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 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. ↑ 2.0 2.1 2.2 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. http://www.leffingwell.com/chirality/nectaryl.htm.
4. ↑ 4.0 4.1 Wolfgang Legrum (2015). "3" (in de). Riechstoffe, zwischen Gestank und Duft (2 ed.). Springer. pp. 51–52. ISBN 978-3-658-07310-7. https://books.google.com/books?id=g-ndBgAAQBAJ&pg=PA51.
5. ↑ ECHA, ed. "2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)cyclopentanone". https://echa.europa.eu/de/substance-information/-/substanceinfo/100.100.590.

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*[CID]: Compound ID
*[H410]: Very toxic to aquatic life with long lasting effects
*[P273]: Avoid release to the environment
*[P391]: Collect spillage
*[P501]: Dispose of contents/container to …