138139-82-9

Basic information

• Product Name: (E)-6,6-DiMethyl-2-hepten-4-ynal
• Synonyms: (E)-6,6-DiMethyl-2-hepten-4-ynal;Terbinafine Related Compound 5
• CAS NO: 138139-82-9
• Molecular Formula: C₉H₁₂O
• Molecular Weight: 136.19098
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 138139-82-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 197.0±23.0 °C(Predicted)
• Appearance: /
• Density: 0.899±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: Chloroform, DMSO (Slightly), Ethyl Acetate
• Stability: Light Sensitive, Moisture Sensitive
• CAS DataBase Reference: (E)-6,6-DiMethyl-2-hepten-4-ynal(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-6,6-DiMethyl-2-hepten-4-ynal(138139-82-9)
• EPA Substance Registry System: (E)-6,6-DiMethyl-2-hepten-4-ynal(138139-82-9)

Safety Data

• Hazardous Substances Data: 138139-82-9(Hazardous Substances Data)

Usage

Description

(E)-6,6-DiMethyl-2-hepten-4-ynal is an organic compound characterized by its unique molecular structure featuring a triple bond and two methyl groups. It is a synthetic intermediate with a variety of applications in the pharmaceutical and chemical industries due to its versatile chemical properties.

Uses

Used in Pharmaceutical Industry:
(E)-6,6-DiMethyl-2-hepten-4-ynal is used as a synthetic intermediate for the production of Terbinafine Hydrochloride (T107500), a synthetic allylamine antifungal agent. (E)-6,6-DiMethyl-2-hepten-4-ynal is effective against a range of fungal infections, making it a valuable component in the development of antifungal medications.
Used in Chemical Synthesis:
In the chemical industry, (E)-6,6-DiMethyl-2-hepten-4-ynal can be utilized as a building block for the synthesis of various complex organic molecules. Its unique structure allows for further functionalization and modification, making it a versatile component in the creation of new compounds with potential applications in various fields.

Upstream product

• 91161-71-6 terbinafin 
• 99473-11-7 Demethylterbinafine 

Downstream Products

• 99473-11-7 Demethylterbinafine 

Relevant articles and documents

CYP2C19 and 3A4 Dominate Metabolic Clearance and Bioactivation of Terbinafine Based on Computational and Experimental Approaches

Lamisil (terbinafine) is an effective, widely prescribed antifungal drug that causes rare idiosyncratic hepatotoxicity. The proposed toxic mechanism involves a reactive metabolite, 6,6-dimethyl-2-hepten-4-ynal (TBF-A), formed through three N-dealkylation pathways. We were the first to characterize them using in vitro studies with human liver microsomes and modeling approaches, yet knowledge of the individual enzymes catalyzing reactions remained unknown. Herein, we employed experimental and computational tools to assess terbinafine metabolism by specific cytochrome P450 isozymes. In vitro inhibitor phenotyping studies revealed six isozymes were involved in one or more N-dealkylation pathways. CYP2C19 and 3A4 contributed to all pathways, and so, we targeted them for steady-state analyses with recombinant isozymes. N-Dealkylation yielding TBF-A directly was catalyzed by CYP2C19 and 3A4 similarly. Nevertheless, CYP2C19 was more efficient than CYP3A4 at N-demethylation and other steps leading to TBF-A. Unlike microsomal reactions, N-denaphthylation was surprisingly efficient for CYP2C19 and 3A4, which was validated by controls. CYP2C19 was the most efficient among all reactions. Nonetheless, CYP3A4 was more selective at steps leading to TBF-A, making it more effective in terbinafine bioactivation based on metabolic split ratios for competing pathways. Model predictions did not extrapolate to quantitative kinetic constants, yet some results for CYP3A4 and CYP2C19 agreed qualitatively with preferred reaction steps and pathways. Clinical data on drug interactions support the CYP3A4 role in terbinafine metabolism, while CYP2C19 remains understudied. Taken together, knowledge of P450s responsible for terbinafine metabolism and TBF-A formation provides a foundation for investigating and mitigating the impact of P450 variations in toxic risks posed to patients.