Chemistry:Dillapiole
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| 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 | |
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| 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). | |
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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. https://books.google.com/books?id=5WY08iuJyawC&q=Chemistry+of+Spices.
- ↑ 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. et al. (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.
- ↑ Shulgin, A. T.; Sargent, T. (1967). "Psychotrophic phenylisopropylamines derived from apiole and dillapiole". Nature 215 (5109): 1494–1495. doi:10.1038/2151494b0. PMID 4861200. Bibcode: 1967Natur.215.1494S.
- ↑ Mankombu Sambasivan Swaminathan, "Improvements in or relating to methylenedioxyphenyl derivatives", IN patent 128,129, 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.
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