Chemical Properties
clear colorless to pale yellow liquid
Definition
ChEBI: A fenchone that has 1S,4R stereochemistry. A colourless, oily liquid found in fennel oil, it is used in perfumery and as flavour in foods.
Uses
As flavor in foods; in perfumes.
Description
d-Fenchone has a camphor-like odor, powerful and sweet, and a warm, somewhat bitter, burning taste. d-Fenchone is isolated from cedarleaf oil (thuja oil).
Occurrence
Reported found in several essential oils: Thuja plicata, Thuja occidentalis, Thuja standishii, Russian anise, fennel, a few Artemisia varieties (A frigida, A verlotorum, A santolinaefolia), Lavanda stoechas, Lavanda burmannii, and others; the highest levels are found in fennel oil (12 to 19%); two optically active forms have been isolated Also reported found in basil, caraway, cedar leaf oil, cloves, dill, licorice and thyme
Preparation
Isolated from cedarleaf oil (thuja oil).
Aroma threshold values
Detection: 510 ppb; aroma characteristics at 1.0%: cooling camphoreous, terpy, spicy, sweet mentholic pine-like.
Taste threshold values
Taste characteristics at 5 ppm: cooling camphoreous, with green citrus lime nuances.
General Description
Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.
Purification Methods
The oily liquid is purified by distillation in a vacuum and is very soluble in EtOH and Et2O. [Boyle et al. J Chem Soc, Chem Commun 395 1971, Hückel Justus Liebigs Ann Chem 549 186 1941, (±)-isomer: Braun & Jacob Chem Ber 66 1461 1933.] It forms two oximes, cis-oxime: m 167o (crystallises from pet ether) [] D +46.5o (c 2, EtOH), O-benzoyloxime m 81o, [] D +49o
