| Identification | More | [Name]
(-)-FENCHONE | [CAS]
7787-20-4 | [Synonyms]
(-)-1,3,3-TRIMETHYL-2-NOEBORNANOL
(-)-1,3,3-TRIMETHYL-2-NORBORNANONE
(1R)-1,3,3-TRIMETHYLBICYCLO[2.2.1]HEPTAN-2-ONE
(1R)-(-)-FENCHONE
ALPHA-FENCHONE
(-)-FENCHONE
FENCHONE
FENCHONE, (-)-
L(-)-1,3,3-TRIMETHYL-2-NORBORBANONE
L(-)-1,3,3-TRIMETHYLBICYCLO[2.2.1]HEPTAN-2-ONE
LAEVO-1,3,3-TRIMETHYLBICYCLO[2.2.1]-2-HEPTANONE
L-ALPHA-FENCHONE
L(-)-FENCHONE
L-FENCHONE
(1R)-1,3,3-trimethyl-norbornan-2-one
1,3,3-trimethyl-,(1R,4S)-Bicyclo[2.2.1]heptan-2-one
3,3-trimethyl-(1theta)-bicyclo[2.2.1]heptan-2-on
(1R)-(-)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one~(-)-1,3,3-Trimethylnorcamphor
L(-)-1,3,3-Trimethyl-2-norbornanone
L-FENCHONE 98+% | [EINECS(EC#)]
232-107-5 | [Molecular Formula]
C10H16O | [MDL Number]
MFCD00151104 | [Molecular Weight]
152.23 | [MOL File]
7787-20-4.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID | [Melting point ]
5-6 °C(lit.) | [alpha ]
[α]D20 -50～-60° (c=4, C2H5OH) | [Boiling point ]
192-194 °C(lit.) | [density ]
0.948 g/mL at 25 °C(lit.)
| [vapor pressure ]
2.149hPa at 20℃ | [FEMA ]
4519 | L-FENCHONE | [refractive index ]
n20/D 1.461(lit.)
| [Fp ]
127 °F
| [storage temp. ]
Flammables area | [solubility ]
Chloroform (Slightly), Ethanol (Slightly, Sonicated) | [form ]
Liquid | [color ]
Clear colorless to light yellow | [Odor]
at 100.00 %. camphor herbal earthy woody | [Odor Type]
camphoreous | [optical activity]
[α]24/D 50.5°, neat | [Water Solubility ]
1.983g/L at 20℃ | [JECFA Number]
2200 | [BRN ]
2042710 | [Dielectric constant]
12.0（20℃） | [LogP]
2.54 at 20℃ | [Uses]
Flavoring. | [CAS DataBase Reference]
7787-20-4(CAS DataBase Reference) | [EPA Substance Registry System]
Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1R,4S)- (7787-20-4) |
| Safety Data | Back Directory | [Risk Statements ]
R10:Flammable. | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 1224 3/PG 3
| [WGK Germany ]
3
| [RTECS ]
RB7875000 | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29142900 | [Toxicity]
The acute oral LD50 value in rats was reported as 616 g/kg (Jenner, Hagan, Taylor. Cook & Fitzhugh, 1964) and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Leven-stein, 1975). |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Anise oil-->Bicyclo[2.2.1]heptane-2-selone, 1,3,3-trimethyl-, (1R,4S)--->Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, oxime, (1R,4S)--->methyl 3-(tert-butyldimethylsilyloxy)benzoate-->(+)-Fenchol-->Methyl 3-hydroxybenzoate-->Methyl 3-methoxybenzoate |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID | [Occurrence]
Reported to be found in many essential oils, including those of Thuja plicata, T.occiden-talis, T.standi shii, Russian anise, fennel, a few Artemisia varieties (A. frigida, A . verlotorum and A . santolinaefolia), Lavandula stoechas and L. burmannii. The highest levels (12-19%) are found in fennel oil (Fenarolis Handbook of Flavor Ingredients, 1975; Gildemeister & Hoffman, 1963). | [Definition]
ChEBI: A fenchone that has (1R,4S)-stereochemistry. It is a constituent of the essential oils obtained from fennel. | [Preparation]
By isolation from cedar leaf oil (Thuja oil) or by various synthetic methods (Arctander, 1969). | [General Description]
(1R)-(-)-Fenchone is a bridged bicyclic ketone found in fennel oil and thuja oil. | [Flammability and Explosibility]
Notclassified | [Pharmacology]
In mice, fenchone injected sc in sesame oil produced clonic convulsions at non-lethal
doses, with a median convulsive dose (CD50) of 1133 mg/kg, and a dose of 500 mg/kg given sc
was an effective arousal agent, reducing the hexobarbitone sleep time (Wenzel & Ross, 1957). In rats, an ip dose of 500 mg/kg had no effect on pentobarbitone-depressed respiration, while ip doses
of 50-400 mg/kg increased running activity but did not affect total activity (Wenzel & Ross, 1957).
Fenchone showed some antispasmodic action on excised mouse intestine (Haginiwa, Harada &
Morishita, 1963), and at 260 mmol/kg showed good choleretic properties of moderately long duration
when given orally in olive oil to rats (M?rsdorf, 1966). Thomas (1958) reported that it acted as
a central nervous system stimulant. Fenchone has been used medically as a counter-irritant (Merck
Index, 1968). | [Metabolism]
Rimini (1901 & 1909) showed that, in the dog, fenchone was probably oxidized to 4-hydroxyfenchone. Reinartz & Zanke (1936) showed that there were other products. They separated, as lead salts, the glucuronides from the urine of dogs receiving d-fenchone. The lead was removed with sulphuric acid and the resulting solution was hydrolysed. In the resulting mixture of hydroxyfen chones, the presence of 4- and 5-hydroxyfenchones and 7r-apofenchone-3-carboxylic acid was demon strated (Williams, 1959). | [Purification Methods]
Purification is as for the (+)-enantiomer above and should have the same physical properties except for opposite optical rotations. UV has max 285nm ( 12.29). [Braun & Jacob Chem Ber 66 1461 1933, UV: Ohloff et al. Chem Ber 90 106 1957.] [Beilstein 7 III 392, 7 IV 212.] |
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