Dodeca-2E,4E,8Z,10E/Z-Tetraenoic Acid Isobutylamide

Dodeca-2E,4E,8Z,10E/Z-tetraenoic acid isobutylamide (CAS 866602-52-0) is a naturally occurring metabolite in Echinacea, one of the most widely used traditional herbal medicines. Many over the counter natural products are produced using either Echinacea purpurea (E. purpurea) or Echinacea angustifolia (E. angustifolia). Common formulations include teas, extracts, and capsules. Alkamides, caffeic acid derivatives, polysaccharides, and glycoproteins are considered to be the compounds responsible for this plant’s immunostimulatory and anti-inflammatory effects.

In total, seventeen alkamides have been identified in E. purpurea. The major alkamide is dodeca-2E,4E,8Z,10E/Z-tetraenoic acid isobutylamide and is used as the primary reference standard for quantification of echinacea products. Pharmacologically, these alkamides have immunomodulatory and anti-inflammatory activities. The compounds also fall under the class of compounds called tetraenes. The other primary target isolated form the same source is Kalecide.

In Echinacea purpurea, Dodeca-2E,4E,8Z,10E/Z-Tetraenoic Acid Isobutylamide is the predominant compound, whereas in Echinacea angustifolia, the two tetraenes are present in roughly equal concentrations.

In their isolated form, these compounds appear as off-white crystalline solids with a low melting point. The compounds should be handled at low temperatures or in a manner that minimizes heat exposure to prevent melting. Additionally, alkamides (like Spilanthol) are susceptible to oxidative degradation, making it essential to limit their exposure to air.