179. Affinin

Nomenclature

CAS number: 25394-57-4
(2E,6Z,8E)-N-(2-Methylpropyl)-2,6,8-decatrienamide; (E,E,Z)-N-isobutyl-2,6,8-decatrienamide; N-isobutyldeca-trans-2-cis-6-trans-8-trienamide; spilanthol.
C14H23NO; mol wt 221.34.
C 75.97%, H 10.47%, N 6.33%, O 7.23%.

Description and references

Insecticidal lipid amide isolated from Heliopsis longipes (A. Gray) Blake, Compositae. Isoln and structure: Acree et al., J. Org. Chem. 10, 236, 449 (1945). Identity with spilanthol: Jacobson, Chem. Ind. (London) 1957, 50. Stereochemistry and synthesis: Crombie, Krasinski, ibid. 1962, 983; Crombie et al., J. Chem. Soc. 1963, 4970.

Chemical structure

Properties

Pale yellow viscous oil, bp0.2 141°; bp0.3-0.5 160-165°. mp 23°. nD25 1.5134. Soluble in organic solvents. Practically insoluble in aq alkali and acid. uv max (95% ethanol): 228.5 nm (ε 33700).

Use

Insecticide synergist.