Piperic acid can be prepared from the commercially-available alkaloid piperine, a cyclic amide containing a piperidine group, by reacting it with a hydroxide such as potassium hydroxide, then acidifying the formed piperate salt with hydrochloric acid or another acid. The toxic compound piperidine is given off during the base-hydrolysis of piperine and as-such, safety precautions should be taken.
Reactionsedit
Reaction of piperic acid with strong oxidizers such as potassium permanganate or ozone, or a halogen such as bromine followed by sodium hydroxide causes oxidative cleavage of the double-bonds, yielding piperonal and piperonylic acid.[3] Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals. On reduction with sodium amalgam piperic acid forms α- and β-dihydropiperic acid, C12H12O4, and the latter can take up two further atoms of hydrogen to produce tetrahydropiperic acid.
piperic, acid, chemical, often, obtained, base, hydrolysis, alkaloid, piperine, from, black, pepper, followed, acidification, corresponding, salt, intermediate, synthesis, other, compounds, such, piperonal, such, used, produce, fragrances, perfumes, flavorants. Piperic acid is a chemical often obtained by the base hydrolysis of the alkaloid piperine 1 from black pepper 2 followed by acidification of the corresponding salt Piperic acid is an intermediate in the synthesis of other compounds such as piperonal and as such may be used to produce fragrances perfumes flavorants and drugs as well as other useful compounds Piperic acid NamesPreferred IUPAC name 2E 4E 5 2H 1 3 Benzodioxol 5 yl penta 2 4 dienoic acidIdentifiersCAS Number 136 72 1 Y3D model JSmol Interactive imageChEBI CHEBI 37316 NChEMBL ChEMBL332122 NChemSpider 4521337 NEC Number 226 118 4MeSH C017637PubChem CID 5370536UNII GFG3FLA9UR YInChI InChI 1S C12H10O4 c13 12 14 4 2 1 3 9 5 6 10 11 7 9 16 8 15 10 h1 7H 8H2 H 13 14 b3 1 4 2 NKey RHBGITBPARBDPH ZPUQHVIOSA N NInChI 1 C12H10O4 c13 12 14 4 2 1 3 9 5 6 10 11 7 9 16 8 15 10 h1 7H 8H2 H 13 14 b3 1 4 2 Key RHBGITBPARBDPH ZPUQHVIOBFSMILES C1OC2 C O1 C C C C2 C C C C C O OPropertiesChemical formula C 12H 10O 4Molar mass 218 208 g mol 1Boiling point decomposesExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 Reactions 3 See also 4 ReferencesPreparation editPiperic acid can be prepared from the commercially available alkaloid piperine a cyclic amide containing a piperidine group by reacting it with a hydroxide such as potassium hydroxide then acidifying the formed piperate salt with hydrochloric acid or another acid The toxic compound piperidine is given off during the base hydrolysis of piperine and as such safety precautions should be taken nbsp Reactions editReaction of piperic acid with strong oxidizers such as potassium permanganate or ozone or a halogen such as bromine followed by sodium hydroxide causes oxidative cleavage of the double bonds yielding piperonal and piperonylic acid 3 Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals On reduction with sodium amalgam piperic acid forms a and b dihydropiperic acid C12H12O4 and the latter can take up two further atoms of hydrogen to produce tetrahydropiperic acid See also editPiperonal Piperine Safrole Isosafrole Sesamol Piperonyl butoxide Cinnamic acidReferences edit Paul M Dewick 2009 Medicinal natural products a biosynthetic approach Chichester A John Wiley amp Sons p 327 ISBN 978 0 470 74167 2 E Gildemeister The Volatile Oils Vol 1 US 5095128 Preparation process for piperonal Retrieved from https en wikipedia org w index php title Piperic acid amp oldid 1068366741, wikipedia, wiki, book, books, library,
