Дегидроэльшольция кетон

Identification

Dehydroelsholtzia ketone, synonym Naginata ketone, CAS 6138-88-1) is a furanoid terpene ketone. Chemical formula C10H12O2. Systematic name: 3-methyl-1-(3-methyl-2-furanyl)-2-buten-1-one (variations: 3-methyl-1-(3-methylfuran-2-yl)but-2-en-1-one). Synonyms include β-dehydroelsholcion, dehydroelsholcyketone.

Physico-chemical characteristics

• Molecular Weight: 164.204
• Exact weight: 164.20
• DSSTox ID: DTXSID20340399
• PSA characteristic: 30.2 Ų
• XLogP3: 2.8
• Density: 1.0005 g/cm³ at 30 °C
• Melting point: 145–146 °C
• Boiling point: 112–116 °C at 20 Torr pressure

Natural spring

Found in the essential oil of several species of the genus Elsholtzia (Elsholtzia, Lamiaceae family): Elsholtzia splendens, E. ciliata, E. cristata, E. winitiana. In the oil of a certain chemotype of Elsholtzia cristata from the Kumaon region (India), dehydroelsholtzium ketone makes up up to 88% of the composition along with minor acylfuran derivatives; in one of the E. winitiana oil samples its share reaches 22.8%.

Aromatic role

Along with geraniol, it is one of the aromatically active components of the essential oil and headspace of Elsholtzia splendens, that is, it directly contributes to the characteristic odor of the plant.

Chemotype diversity

The significant variation in the content of dehydroelsholtzium ketone between chemotypes of the same species - from a few percent to 88% of the oil composition in individual samples of Elsholtzia cristata - illustrates the general phenomenon of chemotypic variability of essential oil plants, in which genetically close populations of the same species produce noticeably different sets of volatile terpenoids depending on growing conditions.

Establishing a structure

The structure of 3-methyl-1-(3-methyl-2-furanyl)-2-buten-1-one was proposed based on data from IR, PMR, mass spectrometry and ¹³C NMR spectroscopy - a comprehensive set of spectral methods, standard for establishing the structure of new terpenoids of essential oils.

Meaning of the genus Elsholtzia

Plants of the genus Elsholtzia (Lamiaceae family) are traditionally used in Chinese and Korean herbal medicine as an antipyretic and anti-cold remedy; their essential oils are a source of a number of furanoid terpenoids, including dehydroelscholcium ketone, which determine the characteristic aroma and part of the biological activity of plant materials.

Industrial significance

The high content of dehydroelsholtzium ketone in certain chemotypes of essential oils of the genus Elsholtzia makes these samples interesting for the perfumery and aromatic industries as a source of a characteristic, easily recognizable furanoid aroma.

Storage

Furanoid terpene ketones with an unsaturated side chain are sensitive to oxidation and light. Store in a tightly closed container, protected from light, in a cool, dry place.