dillapiole

{{chembox

| Watchedfields = changed

| verifiedrevid = 414425598

| Name = Dillapiole

| ImageFile = Dillapiole.svg

| ImageAlt = Skeletal formula

| ImageFile1 = Dillapiole-3D-balls.png

| ImageSize1 = 180

| ImageAlt1 = Ball-and-stick model

| PIN = 4,5-Dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole

| OtherNames = 6-Allyl-4,5-dimethoxybenzo[d][1,3]dioxole
1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9814

| EINECS = 621-020-1

| PubChem = 10231

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C10449

| 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

| InChIKey = LIKYNOPXHGPMIH-UHFFFAOYAI

| SMILES = O1c2cc(c(OC)c(OC)c2OC1)CC=C

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 470874

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LIKYNOPXHGPMIH-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 484-31-1

| CASNo_Comment = {{Citation needed|date=July 2009}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 438CJQ562D

}}

| Section2 = {{Chembox Properties

| C=12 | H=14 | O=4

| Density = 1.163 g/cm³

}}

}}

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.{{cite book|last=Azeez|first=Shamina|title=Chemistry of Spices|year=2008|publisher=Biddles Ltd.|location=Calicut, Kerala, India|isbn=9781845934057|pages=227–241 [230]|url=https://books.google.com/books?id=5WY08iuJyawC&q=Chemistry+of+Spices}} This compound is closely related to apiole, having a methoxy group positioned differently on the benzene ring.{{Cite journal | last1 = Santos | first1 = P. A. G. | last2 = Figueiredo | first2 = A. C. | last3 = Lourenço | first3 = P. M. L. | last4 = Barroso | first4 = J. G. | last5 = Pedro | first5 = L. G. | last6 = Oliveira | first6 = M. M. | last7 = Schripsema | first7 = J. | last8 = Deans | first8 = S. G. | last9 = Scheffer | first9 = J. J. C. | title = Hairy root cultures of Anethum graveolens (Dill): Establishment, growth, time-course study of their essential oil and its comparison with parent plant oils| journal = Biotechnology Letters | volume = 24 | issue = 12 | pages = 1031–1036| year = 2002 | doi = 10.1023/A:1015653701265 | s2cid = 10120732 }}{{Cite journal | doi = 10.1038/2151494b0 | last1 = Shulgin | first1 = A. T. | last2 = Sargent | first2 = T. | title = Psychotrophic phenylisopropylamines derived from apiole and dillapiole | journal = Nature | volume = 215 | issue = 5109 | pages = 1494–1495 | year = 1967| pmid = 4861200| bibcode = 1967Natur.215.1494S | s2cid = 26334093 }} Dillapiole works synergically with certain insecticides like pyrethrins similarly to piperonyl butoxide, which likely results from inhibition of the MFO enzyme of insects.{{cite patent | country = IN | number = 128,129 | status = patent | title = Improvements in or relating to methylenedioxyphenyl derivatives | pubdate = 1970-08-21 | gdate = 1970-10-24 | fdate = | pridate = | inventor = Mankombu Sambasivan Swaminathan | invent1 = | invent2 = | assign1 = | assign2 = | class = | url = }}

No carcinogenicity was detected with parsley apiol or dill apiol in mice.{{cite journal | doi = 10.1093/carcin/5.12.1623| pmid = 6499113| title = 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| journal = Carcinogenesis| volume = 5| issue = 12| pages = 1623–1628| year = 1984| last1 = Phillips| first1 = David H.| last2 = Reddy| first2 = M. Vijayaraj| last3 = Randerath| first3 = Kurt}}