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Dillapiole

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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-dimethoxybenzodioxole
1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.149.911 Edit this at Wikidata
EC Number
  • 621-020-1
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3Key: LIKYNOPXHGPMIH-UHFFFAOYSA-N
  • InChI=1/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3Key: LIKYNOPXHGPMIH-UHFFFAOYAI
SMILES
  • O1c2cc(c(OC)c(OC)c2OC1)CC=C
Properties
Chemical formula C12H14O4
Molar mass 222.240 g·mol
Density 1.163 g/cm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. This compound is closely related to apiole, having a methoxy group positioned differently on the benzene ring. Dillapiole works synergically with certain insecticides like pyrethrins similarly to piperonyl butoxide, which likely results from inhibition of the MFO enzyme of insects.

No carcinogenicity was detected with parsley apiol or dill apiol in mice.

See also

References

  1. Azeez, Shamina (2008). Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. pp. 227–241 . 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

Types of phenylpropenes
Phenylpropenes
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