2-(2-(4-Methyl-3-Cyclohexen-1-Yl)Propyl)Cyclopentanone

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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3728992;
ChemSpider	153032;
EC Number	404-240-0;
PubChem CID	175661;
UNII	P1K3Z8A8HJ ;
	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
Density	0.96 g·cm−3 (22 °C)
Melting point	−41.8 °C (−43.2 °F; 231.3 K)
Boiling point	288 °C (550 °F; 561 K)
Solubility in water	practically insoluble in water (4.6 mg·l−1 at 20 °C)
Hazards
Safety data sheet
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

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]) is reported to be three weeks.^[5]

Uses

The substance is used as a fragrance in exemplary air conditioning products, perfumes and polishes.^[6]

Literature

↑ ^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.
↑ ^2.0 ^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.
↑ John C. Leffingwell. "Chirality & Odour Perception". leffingwell.com. http://www.leffingwell.com/chirality/nectaryl.htm.
↑ Wolfgang Legrum (2015). "3" (in de). Riechstoffe, zwischen Gestank und Duft (2 ed.). Springer. pp. 51. ISBN 978-3-658-07310-7.
↑ Wolfgang Legrum (2015). "3" (in de). Riechstoffe, zwischen Gestank und Duft (2 ed.). Springer. pp. 52. ISBN 978-3-658-07310-7. https://books.google.com/books?id=g-ndBgAAQBAJ&pg=PA52. Retrieved 2019-04-03.
↑ 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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Original source: https://en.wikipedia.org/wiki/2-(2-(4-Methyl-3-cyclohexen-1-yl)propyl)cyclopentanone. Read more

[GESTIS-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.

[stereo_isomers-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] Wolfgang Legrum (2015). "3" (in de). Riechstoffe, zwischen Gestank und Duft (2 ed.). Springer. pp. 51. ISBN 978-3-658-07310-7.

[5] Wolfgang Legrum (2015). "3" (in de). Riechstoffe, zwischen Gestank und Duft (2 ed.). Springer. pp. 52. ISBN 978-3-658-07310-7. https://books.google.com/books?id=g-ndBgAAQBAJ&pg=PA52. Retrieved 2019-04-03.

[6] ECHA, ed. "2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)cyclopentanone". https://echa.europa.eu/de/substance-information/-/substanceinfo/100.100.590.

Names
Structure without shown stereo chemistry
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