Dillapiole
Skeletal formula
Ball-and-stick model
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.149.911 Edit this at Wikidata
EC Number
  • 621-020-1
KEGG
UNII
  • 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 checkY
    Key: LIKYNOPXHGPMIH-UHFFFAOYSA-N checkY
  • 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
  • O1c2cc(c(OC)c(OC)c2OC1)CC=C
Properties
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).
checkY verify (what is checkY☒N ?)

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

  1. ^ Azeez, Shamina (2008). Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. pp. 227–241 [230]. ISBN 9781845934057.
  2. ^ 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.
  3. ^ 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.
  4. ^ IN patent 128,129, Mankombu Sambasivan Swaminathan, "Improvements in or relating to methylenedioxyphenyl derivatives", published 1970-08-21, issued 1970-10-24 
  5. ^ 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.

See also

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