| Piperic acid | |
|---|---|
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5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid |
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| Identifiers | |
| CAS number | 136-72-1 |
| ChEMBL | CHEMBL332122 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C12H10O4 |
| Molar mass | 218.21 g mol−1 |
| Boiling point |
decomposes |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.[3] 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.
Contents |
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.
Reaction of piperic acid with strong oxidizers such as potassium permanganate or ozone, or a halogen such as bromine followed by sodium hydroxide causes the oxidative cleavage of the double-bonds, yielding piperonal via ozonolysis[4][5]. Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals.