Dillapiole

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 (no longer recommended)
Identifiers
484-31-1  YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL470874 YesY
ChemSpider 9814 YesY
ECHA InfoCard 100.149.911
KEGG C10449 YesY
PubChem 10231
Properties
C12H14O4
Molar mass 222.24 g/mol
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).
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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]

No carcinogenicity was detected with parsley apiol or dill apiol in mice.[4]

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" (pdf). Biotechnology Letters. 24 (12): 1031–1036. doi:10.1023/A:1015653701265.
  3. Shulgin, A. T.; Sargent, T. (1967). "Psychotrophic phenylisopropylamines derived from apiole and dillapiole". Nature. 215 (5109): 1494–1495. doi:10.1038/2151494b0. PMID 4861200.
  4. Phillips DH; Reddy MV; Randerath K (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). pp. 1623–8.

See also

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