1195-79-5

Basic information

• Product Name: FENCHONE
• Synonyms: 1,3,3-trimethyl-2-norbornanon;1,3,3-Trimethyl-2-norcamphanone;1,3,3-trimethyl-bicyclo[2.2.1]heptan-2-on;1,3,3-trimethyl-norbornan-2-one;1,3,3-Trimethylnorcamphor;2-Norbornanone, 1,3,3-trimethyl-;2-norbornanone,1,3,3-trimethyl-,(±)-;3,3-dimethyl-
• CAS NO: 1195-79-5
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 214-804-6
• Mol File: 1195-79-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 191.0-192.5℃
• Boiling Point: 193-193.5℃
• Flash Point: 52.8 °C
• Appearance: /
• Density: 0.9484 g/cm3 (20 ºC)
• Vapor Pressure: 0.463mmHg at 25°C
• Refractive Index: 1.4640 (589.3 nm 20℃)
• Water Solubility: 744mg/L at 25℃
• CAS DataBase Reference: FENCHONE(CAS DataBase Reference)
• NIST Chemistry Reference: FENCHONE(1195-79-5)
• EPA Substance Registry System: FENCHONE(1195-79-5)

Safety Data

• Hazardous Substances Data: 1195-79-5(Hazardous Substances Data)

Usage

Description

Fenchone is a monoterpene compound known for its anti-inflammatory and antimicrobial properties. It is also recognized for its ability to inhibit β-secretase (BACE1), which is a drug target for Alzheimer's disease. Fenchone occurs as (1R,4S)-(-)-fenchone in fennel oils and is characterized by its colorless, slightly viscous liquid form with a camphoraceous odor. It can be prepared by dehydrogenation of (-)-fenchol, and (-)-fenchyl esters can be obtained through the addition of carboxylic acids to α-pinene, with subsequent hydrolysis yielding (-)-fenchol.

Uses

Used in Pharmaceutical Industry:
Fenchone is used as an anti-inflammatory agent for its ability to reduce inflammation in various conditions. It is also utilized as an antimicrobial agent, helping to combat bacterial and fungal infections.
Used in Alzheimer's Disease Research:
Fenchone is used as an inhibitor of β-secretase (BACE1) for its potential role in the development of treatments for Alzheimer's disease.
Used in Perfumery:
Fenchone is used as a fragrance ingredient in the perfume industry, contributing to the unique scent of various perfumes and colognes.
Used in Flavor Industry:
Fenchone is used as a flavoring agent in the food and beverage industry, particularly in the creation of artificial fennel oils, which are used to enhance the taste of certain products.
Used in Household Products:
Fenchone is used as a component in the perfume industry to scent household products, such as cleaning agents and air fresheners, providing a pleasant and refreshing aroma.

Flammability and Explosibility

Notclassified

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

Upstream product

• 76-22-2 Camphor 
• 10218-04-9 1-methyl-norbornan-2-one 
• 74-88-4 methyl iodide 
• 4695-62-9 Fenchol 
• 875-06-9 1,3,3-trimethyl-bicyclo[2.2.1]heptane-2-thione 
• 2157-47-3 fenchone oxime 
• 36386-49-9 fenchol 
• 66314-60-1 spiro[1,3,3-trimethyl-bicyclo[2.2.1]heptene-2,2'-(1',3'-dithiolane)] 
• 470-08-6 1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol 
• 13567-57-2 1,3,3-Trimethyl-2-methylidenebicyclo<2.2.1>heptane 
• 10028-15-6 ozone 
• 56022-41-4 nitro-(1,3,3-trimethyl-[2]norbornyliden)-amine 
• 10034-85-2 hydrogen iodide 
• 96093-10-6 (1S,4R)-(+)-1-methyl-3,3-dimethyl-2-methylenebicyclo[2.2.1]heptane 

Downstream Products

• 4695-62-9 Fenchol 
• 77370-41-3 3-methylbutane-1,2,3-tricarboxylic acid 
• 535-77-3 m-cymene 
• 499-75-2 carvacrol 
• 53771-88-3 1-methyl-3-(1-methylethyl)cyclopentane 
• 595-46-0 2,2-dimethylmalonic acid 
• 3637-01-2 3,4-dimethylacetophenone 
• 89929-53-3 (1,3,3-trimethyl-[2]norbornyliden)-aniline 
• 91975-38-1 Allylfenchylalkohol 
• 18368-91-7 2-ethylfenchol 
• 13567-57-2 1,3,3-Trimethyl-2-methylidenebicyclo<2.2.1>heptane 
• 2129-89-7 diphenyl(methyl)phosphine oxide 
• 2157-47-3 fenchone oxime 
• 75-65-0 tert-butyl alcohol 

Relevant articles and documents

Reaction of seleno- or thiofenchone with propiolic acid: Wagner-meerwein rearrangement

A reaction of selenofenchone with propiolic acid in refluxing chloroform produced 1,3-oxaselenin-6-one, which further reacted with acid to afford the ring-opened product. A reaction of 1,3-oxathiin-6-one prepared from thiofenchone with trifluoroacetic acid gave a Wagner-Meerwein rearranged product. In the presence of AlCl3, thiofenchone reacted with methyl propiolate to afford the corresponding rearranged ester.

Kinetics and mechanisms of the tropospheric reactions of menthol, borneol, fenchol, camphor, and fenchone with hydroxyl radicals (OH) and chlorine atoms (Cl)

Relative kinetic techniques have been used to measure the rate coefficients for the reactions of oxygenated terpenes (menthol, borneol, fenchol, camphor, and fenchone) and cyclohexanol with hydroxyl radicals (OH) and chlorine atoms (Cl) at 298 ± 2 K and atmospheric pressure. The rate coefficients obtained for the reactions of the title compounds with OH are the following (in units of 10-11 cm3 molecule-1 s-1): (1.48 ± 0.31), (2.65 ± 0.32), (2.49 ± 0.30), (0.38 ± 0.08), (0.39 ± 0.09) for menthol, borneol, fenchol, camphor, and fenchone, respectively. For the corresponding reactions with Cl atoms the rate coefficients are as follows (in units of 10-10 cm3 molecule-1 s-1): (3.21 ± 0.26), (3.40 ± 0.28), (2.72 ± 0.13), (2.93 ± 0.17), (1.59 ± 0.10), and (1.86 ± 0.29) for cyclohexanol, menthol, borneol, fenchol, camphor, and fenchone, respectively. The reported error is twice the standard deviation. Product studies of the reactions were performed using multipass in situ FTIR (Fourier transform infrared spectroscopy) and solid-phase microextraction (SPME) with analysis by GC-MS (gas chromatography-mass spectrometry). A detailed mechanism is proposed to justify the observed reaction products.

Oxidation of Alcohols by Clay-Supported Iron(III) Nitrate; A New Efficient Oxidizing Agent

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Mechanistic and Synthetic Aspects of Intramolecular Alkoxide-Allene Cyclizations

Intramolecular cyclization of the methoxyallene-alkoxide adducts (1a) proceeds along two different pathways via a methoxyallyl radical anion to give either a dihydrofuran, or vinyl epoxide, depending upon the steric environment of the radical anion.

Palladium(II)-catalyzed ring expansion of a 1-alkenyl cyclopentanol

7,7-Dimethyl-2-methylenenorbornan-1-ol, a strained bicyclic 1-alkenyl cyclopentanol, undergoes Wagner-Meerwein rearrangement to fenchone under treatment with a catalytic amount of PdCl2(PPh3) 2 in refluxing N-methylpyrrolidin-2-one. The described reaction constitutes the first example of the palladium(II)-catalyzed ring expansion of 1-alkenyl cyclopentanols to the corresponding cyclohexanones.