Piperic acid

Piperic acid
Names
	Preferred IUPAC name (2E,4E)-5-(2H-1,3-Benzodioxol-5-yl)penta-2,4-dienoic acid
Identifiers
CAS Number	136-72-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:37316 ;
ChEMBL	ChEMBL332122 ;
ChemSpider	4521337 ;
EC Number	226-118-4;
MeSH	C017637
PubChem CID	5370536;
UNII	GFG3FLA9UR ;
CompTox Dashboard (EPA)	DTXSID801016979 ;
	InChI 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+ Key: RHBGITBPARBDPH-ZPUQHVIOSA-N ; InChI=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-ZPUQHVIOBF;
	SMILES C1OC2=C(O1)C=C(C=C2)/C=C/C=C/C(=O)O;
Properties
Chemical formula	C12H10O4
Molar mass	218.208 g·mol−1
Boiling point	decomposes
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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. 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.

Preparation

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.

Reactions

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.

References

^ Paul M. Dewick. (2009). Medicinal natural products : a biosynthetic approach. Chichester: A John Wiley & Sons. p. 327. ISBN 978-0-470-74167-2.
^ E. Gildemeister. The Volatile Oils. Vol. 1.
^ US 5095128, "Preparation process for piperonal"

[1] Paul M. Dewick. (2009). Medicinal natural products : a biosynthetic approach. Chichester: A John Wiley & Sons. p. 327. ISBN 978-0-470-74167-2.

[2] E. Gildemeister. The Volatile Oils. Vol. 1.

[3] US 5095128, "Preparation process for piperonal"

[1]

[2]

[3]

Preparation

Reactions

See also

References