https://www.sciencemadness.org/smwiki/index.php?title=Ascaridole&feed=atom&action=history
Ascaridole - Revision history
2024-03-28T15:39:19Z
Revision history for this page on the wiki
MediaWiki 1.25.1
https://www.sciencemadness.org/smwiki/index.php?title=Ascaridole&diff=13762&oldid=prev
Mabus: Created page with "{{Chembox | Name = Ascaridole | Reference = | IUPACName = 1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene | PIN = | SystematicName = | OtherNames = Ascaridol<br>As..."
2020-12-29T20:03:24Z
<p>Created page with "{{Chembox | Name = Ascaridole | Reference = | IUPACName = 1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene | PIN = | SystematicName = | OtherNames = Ascaridol<br>As..."</p>
<p><b>New page</b></p><div>{{Chembox<br />
| Name = Ascaridole<br />
| Reference =<br />
| IUPACName = 1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene<br />
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| SystematicName =<br />
| OtherNames = Ascaridol<br>Askaridol<br />
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| Section2 = {{Chembox Properties<br />
| AtmosphericOHRateConstant = <br />
| Appearance = Colorless liquid<br />
| BoilingPt = <br />
| BoilingPtC = 130<br />
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| BoilingPt_notes = (decomposition)<br>40 °C (104 °F; 313 K) (0.2 mmHg)<br />
| Density = 1.010 g/cm<sup>3</sup><br />
| Formula = <br />
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| LogP = 2.64<br />
| MolarMass = 168.23 g/mol<br />
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| MeltingPtC = 3.3<br />
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| Odor = Herb-like<br />
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| Solubility = 0.053 g/100 ml<br />
| SolubleOther = Soluble in [[acetone]], [[benzene]], [[chloroform]], [[dichloromethane]], [[Dimethyl sulfoxide|DMSO]], [[ethyl acetate]]<br />
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'''Ascaridole''' is a naturally-occuring organic compound classified as a bicyclic monoterpenoids that has an unusual bridging peroxide functional group. It has the chemical formula '''C<sub>10</sub>H<sub>16</sub>O<sub>2</sub>'''.<br />
<br />
The compound is interesting since not only it's a naturally occurring organic peroxide, but it's also an explosive compound derived directly from a biological source (in this case the plant Epazote or Mexican tea).<br />
<br />
==Properties==<br />
===Chemical===<br />
Ascaridole will burn if ignited, releasing carbon dioxide, water vapors and soot.<br />
<br />
When reacted with sulfuric acid, or reduced with zinc powder and acetic acid, ascaridole formed cymene. Uncontrolled, the reaction may have an explosive outcome.<br />
<br />
===Physical===<br />
Ascaridole is a colorless liquid with a pungent smell and taste that is soluble in most organic solvents.<br />
<br />
===Explosive===<br />
Like other low molecular weight organic peroxides, it is unstable and prone to explosion when heated above 130 °C or treated with organic acids. This however only happens for large amounts and the deflagration is not very powerful.<br />
<br />
==Availability==<br />
Ascaridole is found Chilean tree boldo and is a major constituent of the oil of Mexican tea (wormseed), in case of the latter it comprises up to 70% of the epazote oil.<br />
<br />
==Preparation==<br />
Ascaridole can be prepared by oxidizing α-terpinene with oxygen under UV light and presence of chlorophyll.<br />
<br />
Explosions&Fire attempted to grow sufficient Mexican tea plants to extract a useful amount of ascaridole. Witness the results (or lack of) [https://www.youtube.com/watch?v=JwTCG15ZB4s here].<br />
<br />
==Projects==<br />
*Make anthelmintic medication<br />
*Food flavoring<br />
*Make biological-derived energetic compound<br />
<br />
==Handling==<br />
===Safety===<br />
Ascaridole is toxic and has a pungent, unpleasant smell and taste.<br />
<br />
In high doses, epazote oil causes irritation of skin and mucous membranes, nausea, vomiting, constipation, headache, vertigo, tinnitus, temporary deafness and blindness. Prolonged action induces depression of the central nervous system and delirium which transits into convulsions and coma. Long-term effects include pulmonary edema (fluid accumulation in the lungs), hematuria, and albuminuria (presence of red blood cells and proteins in the urine, respectively) and jaundice (yellowish pigmentation of the skin).<br />
<br />
===Storage===<br />
Ascaridole in impure form, like epazote oil can be kept for several months before it decomposes too much in contact with air and light.<br />
<br />
Pure ascaridole should be kept in airtight amber bottles, but not for long.<br />
<br />
===Disposal===<br />
Ascaridole can be neutralized with [[iron(II) sulfate]] to ascaridole glycol, which is safer to handle and can be diluted with water and poured down the drain. <br />
<br />
==References==<br />
<references/><br />
===Relevant Sciencemadness threads===<br />
*[http://www.sciencemadness.org/talk/viewthread.php?tid=72292 Explosive ascaridole from epazote herb leaves]<br />
*[http://www.sciencemadness.org/talk/viewthread.php?tid=66117 naturally occuring organic peroxide Ascaridole]<br />
*[http://www.sciencemadness.org/talk/viewthread.php?tid=156022 organic peroxide salts]<br />
<br />
[[Category:Chemical compounds]]<br />
[[Category:Organic compounds]]<br />
[[Category:Peroxides]]<br />
[[Category:Organic peroxides]]<br />
[[Category:Terpenes]]<br />
[[Category:Biologically-derived compounds]]<br />
[[Category:Fragrant compounds]]<br />
[[Category:Energetic materials]]<br />
[[Category:Liquids]]</div>
Mabus