Деметоксиэнцекалин

Identification

Demethoxyencecalin, Desmethoxyencecalin, CAS 19013-07-1) is a natural chromene. Chemical formula C13H14O2. Systematic name: 1-(2,2-dimethyl-2H-chromen-6-yl)ethan-1-one (synonym: 6-acetyl-2,2-dimethylchromene, also 1-(2,2-Dimethylchromen-6-yl)ethanone). EC number: 606-199-6. DSSTox ID: DTXSID30172486. HS code: 2914190090.

Physico-chemical characteristics

• Molecular Weight: 202.253
• Exact weight: 202.25
• EU number: 606-199-6
• DSSTox ID: DTXSID30172486
• HS Code: 2914190090
• PSA characteristic: 26.3 Ų
• XLogP3: 3.23
• Density: 1.1±0.1 g/cm³
• Boiling point: 329.8±42.0 °C at 760 mm Hg. Art.
• Flash point: 147.7±21.4°C
• Refractive index: 1.531
• Solubility in water: 60.26 mg/l at 25 °C (calculated value)

Natural source and role

Isolated from the plant Ageratina adenophora (synonym Eupatorium adenophorum), as well as from the sunflower (Helianthus annuus). Structurally, it is chromene, which differs from the related compound encecalin in the absence of a methoxy group at position 7. In these plants it functions as a phytoalexin, a protective compound produced in response to microbial infection and tissue damage.

Biological activity

Shows antifungal activity, as well as antioxidant and antibacterial properties; The compound has described potential in neurodegenerative disease research. At the same time, the demethyl (hydroxyl) analogue of encecalin is noticeably inferior to encecalin itself in terms of antifeedant and insecticidal activity against cutworm caterpillars Peridroma saucia and Plusia gamma - that is, the absence of a methoxy group reduces the protective effectiveness of the compound against phytophagous insects, although it does not completely eliminate it.

Structural class

Chromene is a bicyclic system consisting of a benzene ring fused to a six-membered oxygen-containing pyran ring. The acetyl group at the 6th position and two methyl groups at the oxygen atom of the pyran ring (2,2-dimethyl) are typical of chromenes of the encecalin group, which are widespread in plants of the Asteraceae family.

Practical significance

Used as an analytical standard and object for phytochemical studies of chromenes of the genus Ageratina/Eupatorium/Helianthus. Comparison of the activities of demethoxyencecalin and encecalin is a convenient model for studying the role of individual methoxy groups in the protective effect of plant chromenes against phytophagous insects.

Invasive source status

Ageratina adenophora (Eupatorium adenophorum) is an invasive asteraceous plant native to Mexico that has become widespread in tropical and subtropical regions of Asia and Africa, where it actively displaces native flora. The high competitiveness of the species is partly associated with the accumulation of protective chromenes, including demethoxyencecalin and encecalin, which reduce the consumption of the plant by local phytophagous insects.

Storage

Chromenes with an unsaturated pyran ring are sensitive to oxidation and light. Store in a container protected from light, in a cool, dry place, avoiding prolonged contact with air after opening the package.

Invasive status of the source plant

Ageratina adenophora (Eupatorium adenophorum) is an invasive asteraceous plant native to Mexico that has become widespread in tropical and subtropical regions of Asia and Africa, displacing native flora. The high competitiveness of the species is partly explained by the active accumulation of protective chromenes, including demethoxyencecalin and encecalin, which reduce the attractiveness of the plant to local herbivorous insects.