CAS 7787-20-4

(-)-Fenchone

Description:

(-)-Fenchone is a bicyclic monoterpene ketone, primarily derived from the essential oils of various plants, particularly those in the fennel and rosemary families. It is characterized by its unique structure, which includes a cyclobutane ring fused to a cyclopentane ring, contributing to its distinctive aromatic properties. The compound exhibits a strong, camphor-like odor and is often used in perfumery and flavoring applications. (-)-Fenchone is optically active, with a specific rotation that indicates its chiral nature, and it exists in two enantiomeric forms, with the (-)-enantiomer being the naturally occurring one. In terms of solubility, it is generally soluble in organic solvents but has limited solubility in water. (-)-Fenchone also possesses potential biological activities, including antimicrobial and anti-inflammatory properties, making it of interest in various fields, including pharmacology and natural product chemistry. Its CAS number, 7787-20-4, is a unique identifier used for regulatory and safety purposes in chemical databases.

Formula: C₁₀H₁₆O

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

InChI key: InChIKey=LHXDLQBQYFFVNW-OIBJUYFYSA-N

SMILES: C[C@]12C(=O)C(C)(C)[C@](C1)(CC2)[H]

Synonyms:

• (-)-Fenchone
• (1R)-(-)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one~(-)-1,3,3-Trimethylnorcamphor
• (1R)-(?-Fenchone
• (1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
• (R)-(-)-Fenchone
• 2-Norbornanone, 1,3,3-trimethyl-, (1R,4S)-(-)-
• <span class="text-smallcaps">L</span>-(-)-Fenchone
• Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1R)-
• Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1R,4S)-
• L(-)-1,3,3-Trimethyl-2-norbornanone
• L(-)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one

(-)-Fenchone

CAS: 7787-20-4

(-)-Fenchone is the major component of the oil from the leaves and twigs of plants in the citrus family. It has been shown to inhibit replication of human liver and lung viruses, including influenza A virus, hepatitis C virus, and dengue virus. (-)-Fenchone also has anticancer activity, which may be due to its ability to inhibit DNA topoisomerase II. (-)-Fenchone has been shown to have a rate enhancement effect on protein synthesis in model proteins. In addition, (-)-fenchone inhibits adrenergic receptors at low concentrations that are not lethal to cells. This inhibition could be a basis for future research into treatments for diseases such as Alzheimer’s disease or Parkinson’s disease where these receptors are involved.

Formula: C₁₀H₁₆O

Purity: Min. 95%

Molecular weight: 152.23 g/mol

Ref: 3D-FF165228

(1R,​4S)​-1,​3,​3-​Trimethylbicyclo[2.2.1]​heptan-​2-​one

Controlled Product

CAS: 7787-20-4

Applications (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.
References Rahman, S., et al. J. Biol. Chem., 292, 18916-23 (2017); Takaishi, M., et al.: J Physio. Sci., 64, 47-57 (2014)

Formula: C₁₀H₁₆O

Color and Shape: Colourless

Molecular weight: 152.23

Ref: TR-T798050