Fenchone

Structural formula
	(+) - Fenchon (left) and (-) - Fenchon (right)
General
Surname	Fenchone
other names	(+) - fenchone; (-) - fenchone; (±) -Fenchon; (1 S , 4 R ) -1,3,3-trimethylbicyclo [2.2.1] heptan-2-one; (1 R , 4 S ) -1,3,3-trimethylbicyclo [2.2.1] heptan-2-one;
Molecular formula	C 10 H 16 O
Brief description	colorless liquid
External identifiers / databases
EC number	214-804-6
ECHA InfoCard	100.013.458
PubChem	14525
ChemSpider	13869
Wikidata	Q414784
properties
Molar mass	152.23 g · mol -1
Physical state	liquid
density	0.95 g cm −3 (20 ° C)
Melting point	5 ° C
boiling point	63–65 ° C (17 hPa)
solubility	very bad in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 226
	P: 303 + 361 + 353-403 + 235
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fenchon is a bicyclic monoterpene - ketone . It is found in fennel and is part of many essential oils . It is insoluble in water, but readily soluble in ethanol . It occurs in the form of two enantiomers .

Fennel bulbs - fenchon occurs naturally in fennel

(-) - Fenchone [synonym: (1 R , 4 S ) -1,3,3-trimethylbicyclo [2.2.1] heptan-2-one] solidifies at 5 ° C and boils at about 193 ° C.
(+) - Fenchone [synonym: (1 S , 4 R ) -1,3,3-trimethylbicyclo [2.2.1] heptan-2-one] solidifies between 5 and 7 ° C.

The density for both enantiomers is 0.95 g · cm ⁻³ . Fenchon tastes bitter and smells like camphor. It inhibits the growth of bacteria and fungi . In higher doses, it has a central stimulating effect on the human organism.

The reduction of racemic fenchone produces fenchols , which occur in four isomeric forms. The fenchols are important as components of perfumes .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet (+) - Fenchon (PDF) from Carl Roth , accessed on June 6, 2018.
↑ Data sheet D (+) - Fenchone at Acros, accessed on February 19, 2010.
^ University of Erlangen : Natural Products Chemistry: Terpenes ( Memento from December 3, 2008 in the Internet Archive ), lecture script.

[ROTH-1] ↑ ^a ^b ^c ^d ^e ^f data sheet (+) - Fenchon (PDF) from Carl Roth , accessed on June 6, 2018.

[2] Data sheet D (+) - Fenchone at Acros, accessed on February 19, 2010.

[3] University of Erlangen : Natural Products Chemistry: Terpenes ( Memento from December 3, 2008 in the Internet Archive ), lecture script.