(-)-Fenchone

Names

[ Name ]:
(-)-Fenchone

[Synonym ]:
(1R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one
EINECS 232-107-5
MFCD00151104
(1R)-(-)-Fenchone
2-Norbornanone, 1,3,3-trimethyl-, (1R,4S)-(+)-
(-)-1,3,3-Trimethyl-2-norbornanone
Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1R,4S)-
(+)-FENCHONE
(1R,4S)-fenchone

Biological Activity

[Description]:

(-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Thuja occidentalis. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Miyazawa M, et al. Metabolism of (-)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes. Xenobiotica. 2007;37(2):194-204.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
193.5±0.0 °C at 760 mmHg

[ Melting Point ]:
5ºC

[ Molecular Formula ]:
C₁₀H₁₆O

[ Molecular Weight ]:
152.233

[ Flash Point ]:
52.8±0.0 °C

[ Exact Mass ]:
152.120117

[ PSA ]:
17.07000

[ LogP ]:
2.13

[ Vapour Pressure ]:
0.5±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.485

[ Storage condition ]:
Flammables area

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H226

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Risk Phrases ]:
R10

[ Safety Phrases ]:
S16

[ RIDADR ]:
UN 1224 3/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
RB7875000

[ Packaging Group ]:
III

[ Hazard Class ]:
3.0

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

[Chemical composition of essential oil obtained from Romanian fennel fruits].

Rev. Med. Chir. Soc. Med. Nat. Iasi. 115(2) , 590-4, (2011)

For therapeutical purposes, fennel (Foeniculum vulgare Mill.), an important aromatic plant, is used for its expectorant, antispasmodic, carminative and diuretic properties. The chemical composition, e...

Biosynthesis of monoterpenes: conversion of the acyclic precursors geranyl pyrophosphate and neryl pyrophosphate to the rearranged monoterpenes fenchol and fenchone by a soluble enzyme preparation from fennel (Foeniculum vulgare).

Arch. Biochem. Biophys. 200(2) , 524-33, (1980)

Kinetics and mechanisms of the tropospheric reactions of menthol, borneol, fenchol, camphor, and fenchone with hydroxyl radicals (OH) and chlorine atoms (Cl).

J. Phys. Chem. A 116(16) , 4097-107, (2012)

Relative kinetic techniques have been used to measure the rate coefficients for the reactions of oxygenated terpenes (menthol, borneol, fenchol, camphor, and fenchone) and cyclohexanol with hydroxyl r...