(-)-FENCHONE
- CAS NO.:4695-62-9
- Empirical Formula: C10H16O
- Molecular Weight: 152.23
- MDL number: MFCD00151104
- EINECS: 225-160-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-07 19:09:42
What is (-)-FENCHONE?
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
The Uses of (-)-FENCHONE
As flavor in foods; in perfumes.
The Uses of (-)-FENCHONE
Reference Standard in the analysis of herbal medicinal products
What are the applications of Application
(+)-Fenchone is an analytical standard
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
Properties of (-)-FENCHONE
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 | n |
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 |
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℃) |
EPA Substance Registry System | Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1S,4R)- (4695-62-9) |
Safety information for (-)-FENCHONE
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 |
GHS Hazard Statements |
H226:Flammable liquids |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P240:Ground/bond container and receiving equipment. P241:Use explosion-proof electrical/ventilating/lighting/…/equipment. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
Computed Descriptors for (-)-FENCHONE
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