7787-20-4

Basic information

• Product Name: (-)-FENCHONE
• Synonyms: (-)-FENCHONE;FENCHONE;FENCHONE, (-)-;L-ALPHA-FENCHONE;LAEVO-1,3,3-TRIMETHYLBICYCLO[2.2.1]-2-HEPTANONE;L(-)-FENCHONE;L-FENCHONE;L(-)-1,3,3-TRIMETHYL-2-NORBORBANONE
• CAS NO: 7787-20-4
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 232-107-5
• Product Categories: Bicyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 7787-20-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 5-6 °C(lit.)
• Boiling Point: 192-194 °C(lit.)
• Flash Point: 127 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.948 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.463mmHg at 25°C
• Refractive Index: n20/D 1.461(lit.)
• Storage Temp.: Flammables area
• Solubility: Chloroform (Slightly), Ethanol (Slightly, Sonicated)
• Water Solubility: 1.983g/L at 20℃
• BRN: 2042710
• CAS DataBase Reference: (-)-FENCHONE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-FENCHONE(7787-20-4)
• EPA Substance Registry System: (-)-FENCHONE(7787-20-4)

Safety Data

• Statements: 10
• Safety Statements: 23-24/25
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• RTECS: RB7875000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 7787-20-4(Hazardous Substances Data)

Usage

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).

Uses

(1R,?4S)?-1,?3,?3-?Trimethylbicyclo[2.2.1]?heptan-?2-?one also known more commonly as (-)-Fenchone is a chiral intermediate of Fenchone and is currently being used for studies ranging from inhibitory effects of monoterpenes on human TRPA1 and odorant receptor of the malaria vector Anopheles gambiae.

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.]

InChI:InChI=1/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1

Upstream product

• 53402-11-2 thiofenchone 
• 470-08-6 α-fenchyl alcohol 
• 74163-80-7 (1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptane-2-one oxime 
• 73509-03-2 (1R)-(-)-Fenchone hydrazone 
• 18084-01-0 (1R,4S)-2-Ethynyl-1,3,3-trimethyl-bicyclo[2.2.1]heptan-2-ol 
• 89050-88-4 (1R)-2-diazo-1,3,3-trimethylbicyclo[2.2.1]heptane 
• 2217-02-9 (1R)-endo-(+)-fenchol 

Downstream Products

• 1268280-99-4 C₂₄H₂₆F₃O₃P 
• 1268280-99-4 C₂₄H₂₆F₃O₃P 
• 1268280-98-3 C₂₃H₂₇O₃P 
• 1268280-98-3 C₂₃H₂₇O₃P 
• 1268280-91-6 C₁₇H₂₄O₂ 
• 1268280-92-7 C₁₉H₂₂F₆O₂ 
• 1268280-94-9 C₂₄H₂₇F₃O₂ 
• 1268280-93-8 C₂₃H₂₈O₂ 
• 1268280-90-5 C₁₆H₂₂O₂ 
• 240117-99-1 (1R,2R,4S)-2-endo-hydroxy-2-exo-(o-methoxybenzene)-1,3,3-trimethylbicyclo[2.2.1]heptane 
• 93477-30-6 (1R)-2endo-benzamino-1.3.3-trimethyl-norbornane 
• 161276-73-9 (1R,2R)-2-endo-hydroxy-2-exo-phenyl-1,3,3-trimethylbicyclo[2.2.1]heptane 
• 791620-43-4 (1R,2R,4S)-1,3,3-trimethyl-2-[(Z)-1-methylprop-1-en-1-yl]bicyclo[2.2.1]heptan-2-ol 
• 791620-43-4 (1R,2R,4S)-1,3,3-trimethyl-2-[(E)-1-methylprop-1-en-1-yl]bicyclo[2.2.1]heptan-2-ol 

Relevant articles and documents

A Structural View on the Stereospecificity of Plant Borneol-Type Dehydrogenases

The development of sustainable processes for the valorization of byproducts and other waste streams remains an ongoing challenge in the field of catalysis. Racemic borneol, isoborneol and camphor are currently produced from α-pinene, a side product from the production of cellulose. The pure enantiomers of these monoterpenoids have numerous applications in cosmetics and act as reagents for asymmetric synthesis, making an enzymatic route for their separation into optically pure enantiomers a desirable goal. Known short-chain borneol-type dehydrogenases (BDHs) from plants and bacteria lack the required specificity, stability or activity for industrial utilization. Prompted by reports on the presence of pure (?)-borneol and (?)-camphor in essential oils from rosemary, we set out to investigate dehydrogenases from the genus Salvia and discovered a dehydrogenase with high specificity (E>120) and high specific activity (>0.02 U mg?1) for borneol and isoborneol. Compared to other specific dehydrogenases, the one reported here shows remarkably higher stability, which was exploited to obtain the first three-dimensional structure of an enantiospecific borneol-type short-chain dehydrogenase. This, together with docking studies, led to the identification of a hydrophobic pocket in the enzyme that plays a crucial role in the stereo discrimination of bornane-type monoterpenoids. The kinetic resolution of borneol and isoborneol can be easily integrated into the existing synthetic route from α-pinene to camphor thereby allowing the facile synthesis of optically pure monoterpenols from an abundant renewable source.

Photochemical Oxidation of Thioketones by Singlet Molecular Oxygen Revisited: Insights into Photoproducts, Kinetics, and Reaction Mechanism

Photosensitized oxidation of trimethyl[2.2.1]bicycloheptane thioketones by 1O2 can yield more photoproducts than exclusively ketones and sulfines. Moreover, the ketone/sulfine ratio can be reversed when protic conditions and high thioketone concentrations are used, conversely to earlier results reporting ketones as the main photoproducts. A new mechanistic proposal for sulfine formation is suggested following intermolecular oxygen transfer from a peroxythiocarbonyl intermediate to a second thioketone molecule. Reaction quantum yields (10-5-10-2) depend on the reaction conditions and time. Sulfine production reaches a maximum at short irradiation times, whereas decomposition to the corresponding ketone is observed at long reaction times. When the thioketone substrate has a hydrogen atom at the α position a peroxyvinylsulfenic acid intermediate can be formed by proton transfer. Reaction of this intermediate with another thioketone molecule can yield more sulfine and its tautomeric vinylsulfenic acid, which dimerizes in situ to the thiosulfinate. The hydroperoxyl group of the peroxyvinylsulfenic acid can also rearrange to the α position, and by reaction with the starting thioketone, α-hydroxy thioketone and additional sulfine can be formed, while dehydration yields the α-oxo thioketone. In situ [2 + 2] and [4 + 2] self-cycloaddition of the α-oxo thioketone yields significant amounts of the corresponding adducts at prolonged irradiation times.

Direct amination of bio-alcohols using ammonia

A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed on a larger batch scale for the conversion of isomannide to the corresponding diamine. Additionally, it was shown that the catalyst is stable for at least six consecutive runs. No significant loss of activity and selectivity was observed.