Жасмолин I

Description

Jasmolin I is one of the six natural esters that make up pyrethrum: an insecticidal extract of the dried inflorescences of the Dalmatian chamomile Chrysanthemum cinerariifolium (Tanacetum cinerariifolium). A complete set of active ingredients of pyrethrum - pyrethrin I and II, cinnerin I and II, jasmoline I and II. Chemically, it is an ester of chrysanthemum acid (2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylic acid) and jasmolone; configuration (1R,3R), natural form is left-handed. The three series of esters differ only in the terminal fragment of the alcohol part: in jasmoline it is an ethyl group, in cinerine it is a methyl group, and in pyrethrin it is a vinyl group. The differences are small, but the toxicity of the six compounds to insects varies markedly.

Basic Attributes

• CAS No.: 4466-14-2 (the card also shows 6860-62-4 and 39668-90-1)
• Chemical formula: C21H30O3
• Molecular Weight: 331.46900
• Exact weight: 330.46
• Catalog section: ketones
• Synonyms: jasmoline I, (−)-jasmoline I

The molecular weight and exact mass values ​​in the original card differ by one; calculation using the gross formula C21H30O3 gives 330.5. When preparing documents, the value is checked against the batch passport.

Physico-chemical characteristics

• PSA: 43.37000
• XLogP3: 4.90520
• Density: 1.039 g/cm³
• Boiling point: 417.473 °C at 760 mm Hg. Art.
• Flash point: 178.537 °C
• Refractive index: 1.517

Mechanism of action

Pyrethrins affect voltage-gated sodium channels in insect nerve cells: the channel remains open longer than it should, the action potential is extended, and nerve transmission is disrupted. The result is immediate paralysis (“knockdown”) followed by death. Pyrethrum is classified as a contact insecticide of botanical origin without residual action: oxygen, light, moisture and elevated temperature destroy active esters in a short time.

Scope of application

• analytical standard for quantitative determination of the composition of pyrethrum by HPLC and GC methods
• reference substance for the control of Dalmatian chamomile raw materials and commercial pyrethrin extracts
• standard for determining residual amounts of pyrethrins in food products
• reagent in studies of insect sodium channels and resistance mechanisms

Safety Information

• Packing level: III
• Hazard category: 6.1(b)
• Transport codes: UN 2902

Storage and handling

Store refrigerated, in a tightly closed, light-proof container, away from air and moisture. The ether quickly decomposes in light and when heated; alkaline media hydrolyze the ester bond. Work with gloves and safety glasses, avoid the formation of aerosol.