Title: Affinin
CAS Registry Number: 25394-57-4
CAS Name: (2E,6Z,8E)-N-(2-Methylpropyl)-2,6,8-decatrienamide
Additional Names: (E,E,Z)-N-isobutyl-2,6,8-decatrienamide; N-isobutyldeca-trans-2-cis-6-trans-8-trienamide; spilanthol
Molecular Formula: C14H23NO
Molecular Weight: 221.34
Percent Composition: C 75.97%, H 10.47%, N 6.33%, O 7.23%
Literature 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.
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 (e 33700).
Melting point: mp 23°
Boiling point: bp0.2 141°; bp0.3-0.5 160-165°
Index of refraction: nD25 1.5134
Absorption maximum: uv max (95% ethanol): 228.5 nm (e 33700)
Use: Insecticide synergist.
Aflatoxins B Aflatoxins G Aflatoxins M Afloqualone Agaricic Acid

Spilanthol skeletal.svg
CAS number 25394-57-4
PubChem 5353001
ChemSpider 4509783
Jmol-3D images Image 1
Molecular formula C14H23NO
Molar mass 221.34 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Spilanthol is a fatty acid amide isolated from Acmella oleracea.[1] It is believed to be responsible for the local anesthetic properties of the plant.[2]

Spilanthol permeates the human skin [3] and buccal mucosa,[4] resulting in local as well as systemic pharmacological concentrations.