Dillapiole: Difference between revisions
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Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG. |
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{{Refimprove|date=July 2009}} |
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{{chembox |
{{chembox |
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| Watchedfields = changed |
| Watchedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 414425598 |
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| Name = Dillapiole |
| Name = Dillapiole |
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| ImageFile = Dillapiole |
| ImageFile = Dillapiole structure.svg |
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| ImageAlt = Skeletal formula |
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<!-- | ImageSize = 120px --> |
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| ImageFile1 = Dillapiole-3D-balls.png |
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| ImageName = |
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| ImageSize1 = 180 |
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| ImageAlt1 = Ball-and-stick model |
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| PIN = 4,5-Dimethoxy-6-(prop-2-en-1-yl)-2''H''-1,3-benzodioxole |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 9814 |
| ChemSpiderID = 9814 |
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| EINECS = 621-020-1 |
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| PubChem = 10231 |
| PubChem = 10231 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C10449 |
| KEGG = C10449 |
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| 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 |
| 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 |
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| InChIKey = LIKYNOPXHGPMIH-UHFFFAOYAI |
| InChIKey = LIKYNOPXHGPMIH-UHFFFAOYAI |
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| SMILES = O1c2cc(c(OC)c(OC)c2OC1)CC=C |
| SMILES = O1c2cc(c(OC)c(OC)c2OC1)CC=C |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 470874 |
| ChEMBL = 470874 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LIKYNOPXHGPMIH-UHFFFAOYSA-N |
| StdInChIKey = LIKYNOPXHGPMIH-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 484-31-1 |
| CASNo = 484-31-1 |
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| CASNo_Comment = {{Citation needed|date=July 2009}} |
| CASNo_Comment = {{Citation needed|date=July 2009}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 438CJQ562D |
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}} |
}} |
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| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
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| C=12 | H=14 | O=4 |
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| |
| Density = 1.163 g/cm<sup>3</sup> |
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| Density = 1.163 g/cm³ |
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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.<ref>{{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}}</ref> This compound is closely related to [[apiole]], having a [[methoxy]] group positioned differently on the [[benzene ring]].<ref>{{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 }}</ref><ref>{{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 }}</ref> Dillapiole works synergically with certain insecticides like [[pyrethrin]]s similarly to [[piperonyl butoxide]], which likely results from inhibition of the [[Mixed-function_oxidase|MFO]] enzyme of insects.<ref>{{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 = }}</ref> |
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'''Dillapiole''' is an [[organic chemical compound]] and [[essential oil]] commonly extracted from [[dill weed]], though can be found in a variety of other plants. |
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No carcinogenicity was detected with parsley apiol or dill apiol in mice.<ref>{{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}}</ref> |
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This compound is closely related to [[apiole]] having a [[methoxy]] group positioned differently on the [[benzene ring]] {{Citation needed|date=July 2009}}. |
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{{reflist}} |
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{{Citation style|date=September 2007}} |
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<references/> |
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* Shulgin, Alexander. "Psychotropic Phenylisopropylamines derived from Apiole and Dillapiole". Nature 215, 1494-95 (1967) |
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== See also == |
== See also == |
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* [[ |
* [[Apiole]] |
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* [[Phenylpropene]] |
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{{Phenylpropene}} |
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[[Category:Phenylpropanoids]] |
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[[Category:O-methylated phenylpropanoids]] |
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[[Category:Benzodioxoles]] |
[[Category:Benzodioxoles]] |
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[[Category: |
[[Category:Allyl compounds]] |
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[[Category: |
[[Category:Pyrogallol ethers]] |
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[[Category:Hydroxyquinol ethers]] |
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{{aromatic-stub}} |
{{aromatic-stub}} |
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[[de:Dillapiol]] |
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[[id:Dilapiola]] |