(-)-FENCHONE Chemical Properties

Melting point:

5-6 °C(lit.)

Boiling point:

192-194 °C(lit.)

alpha 

D20 +66.9°

Density 

0.948 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.461(lit.)

FEMA 

2479 | D-FENCHONE

Flash point:

127 °F

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Liquid

color 

Clear colorless to pale yellow

Odor

at 100.00 %. camphor thuja cedarleaf herbal earthy woody

Odor Type

balsamic

optical activity

[α]20/D +62±1°, neat

Water Solubility 

2.147g/L(25 ºC)

JECFA Number

1396

Merck 

14,3968

BRN 

2206555

Dielectric constant

12.0（20℃）

LogP

2.089 (est)

EPA Substance Registry System

Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1S,4R)- (4695-62-9)

Safety Information

Risk Statements 

10

Safety Statements 

23-24/25

RIDADR 

UN 1224 3/PG 3

WGK Germany 

3

RTECS 

RB7875200

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29142990

Toxicity

LD50 orally in rats: 6.16 g/kg (Jenner)

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(-)-FENCHONE Usage And Synthesis

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).

Chemical Properties

clear colorless to pale yellow liquid

Chemical Properties

d-Fenchone has a camphor-like odor, powerful and sweet and a warm, somewhat bitter, burning taste.

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

Uses

Reference Standard in the analysis of herbal medicinal products

Uses

As flavor in foods; in perfumes.

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.

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

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