Dillapiole

Dillapiole is an organic chemical compound and essential oil commonly extracted from dill weed, although it can also be found in various other plants such as fennel root[1]. This compound is closely related to apiole, with a methoxy group positioned differently on the benzene ring[1]. Dillapiole has been found to work synergistically with certain insecticides like pyrethrins, similar to piperonyl butoxide, which is likely due to the inhibition of the MFO enzyme in insects[1].

No carcinogenicity was detected with parsley apiol or dill apiol in mice[1]. Dillapiole is also a phenylpropanoid found in abundance in essential oils from Piper species, Deverra triradiata Hochst. ex, and Yampah from Subalpine Meadows in Southwestern Montana, and has been studied for its immunomodulatory activity[2]. It has been isolated from perilla frutenscens and is a constituent of Japanese, Indian (Anethum sowa), and European (Anethum graveolens) dill oils, as well as Piper spp., and seeds of Bunium persicum (black caraway)[3].

Dillapiole is one of the two naturally occurring aromatic ethers that are the ring-methoxylated analogues of myristicin, along with apiole[4]. It has been mentioned in the context of psychotropic phenylisopropylamines derived from apiole and dillapiole[4]. The chemical structure and properties of dillapiole, including its classification, patents, literature, biological activities, and more, can be found on PubChem[5].

Citations:

[1] https://en.wikipedia.org/wiki/Dillapiole

[2] https://www.mdpi.com/2223-7747/12/14/2643

[3] http://www.thegoodscentscompany.com/data/rw1019661.html

[4] https://www.nature.com/articles/2151494b0.pdf

[5] https://pubchem.ncbi.nlm.nih.gov/compound/Dillapiol