Dillapiole

Dillapiole
Names


Preferred IUPAC name 4,5-Dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole
Other names 6-Allyl-4,5-dimethoxybenzo[d][1,3]dioxole 1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene
Identifiers
CAS Number	484-31-1 ^{[citation needed]}^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL470874^Y
ChemSpider	9814^Y
ECHA InfoCard	100.149.911
EC Number	621-020-1
KEGG	C10449^Y
PubChem CID	10231
UNII	438CJQ562D^Y
InChI InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3^Y Key: LIKYNOPXHGPMIH-UHFFFAOYSA-N^Y InChI=1/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3 Key: LIKYNOPXHGPMIH-UHFFFAOYAI
SMILES O1c2cc(c(OC)c(OC)c2OC1)CC=C
Properties
Chemical formula	C₁₂H₁₄O₄
Molar mass	222.240 g·mol⁻¹
Density	1.163 g/cm³
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Dillapiole is an organic chemical compound and essential oil commonly extracted from dill weed, though it can be found in a variety of other plants such as fennel root.^[1] This compound is closely related to apiole, having a methoxy group positioned differently on the benzene ring.^[2]^[3] Dillapiole works synergically with certain insecticides like pyrethrins similarly to piperonyl butoxide, which likely results from inhibition of the MFO enzyme of insects.^[4]

No carcinogenicity was detected with parsley apiol or dill apiol in mice.^[5]

References

^ Azeez, Shamina (2008). Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. pp. 227–241 [230]. ISBN 9781845934057.
^ Santos, P. A. G.; Figueiredo, A. C.; Lourenço, P. M. L.; Barroso, J. G.; Pedro, L. G.; Oliveira, M. M.; Schripsema, J.; Deans, S. G.; Scheffer, J. J. C. (2002). "Hairy root cultures of Anethum graveolens (Dill): Establishment, growth, time-course study of their essential oil and its comparison with parent plant oils". Biotechnology Letters. 24 (12): 1031–1036. doi:10.1023/A:1015653701265. S2CID 10120732.
^ Shulgin, A. T.; Sargent, T. (1967). "Psychotrophic phenylisopropylamines derived from apiole and dillapiole". Nature. 215 (5109): 1494–1495. Bibcode:1967Natur.215.1494S. doi:10.1038/2151494b0. PMID 4861200. S2CID 26334093.
^ IN patent 128,129, Mankombu Sambasivan Swaminathan, "Improvements in or relating to methylenedioxyphenyl derivatives", published 1970-08-21, issued 1970-10-24
^ Phillips, David H.; Reddy, M. Vijayaraj; Randerath, Kurt (1984). "32P-Post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. II. Newborn male B6C3F1 mice". Carcinogenesis. 5 (12): 1623–1628. doi:10.1093/carcin/5.12.1623. PMID 6499113.