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Piperic acid
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Piperic acid is a chemical often obtained by the base-hydrolysis of the

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alkaloid piperine[1] from black pepper,[2] followed by acidification of the

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corresponding salt.[3] Piperic acid is an intermediate in the synthesis of

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Piperic acid

other compounds such as piperonal, and as-such may be used to

produce fragrances, perfumes flavorants and drugs as well as other
useful compounds.

Names
IUPAC name
(2E,4E)-5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic

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acid

1 Preparation

Identifiers

2 Reactions
3 See also
4 References

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Preparation

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Piperic acid can be prepared from the commercially-available alkaloid

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piperine, a cyclic amide containing a piperidine group, by reacting it with

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a hydroxide such as potassium hydroxide, then acidifying the formed

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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.

CAS Number

136-72-1

ChEBI

CHEBI:37316

ChEMBL

ChEMBL332122

ChemSpider

4521337

EC Number

226-118-4

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MeSH

C017637

PubChem

5370536

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

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InChI=1/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(79)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1+,4-2+
Key: RHBGITBPARBDPH-ZPUQHVIOBF

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SMILES

Printable version

C1OC2=C(O1)C=C(C=C2)/C=C/C=C/C(=O)O

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Properties

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Deutsch

Chemical formula

C 12H 10O4

/ srpski

Molar mass

218.21 gmol1

Srpskohrvatski /

Boiling point

decomposes

Except where otherwise noted, data are given for

materials in their standard state (at 25 C [77 F],
100 kPa).

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Infobox references

Reactions

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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.[4][5] 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 - and -dihydropiperic acid, C12H12O4, and the latter
can take up two further atoms of hydrogen to produce tetrahydropiperic acid.

See also
Piperonal
Piperine
Safrole
Isosafrole
Sesamol

[ edit ]

Piperonyl butoxide
Cinnamic acid

References

[ edit ]

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. ^ http://chestofbooks.com/health/aromatherapy/The-Volatile-Oils-Vol1/Heliotropin.html
3. ^ http://www.erowid.org/archive/rhodium/chemistry/3base/piperonal.pepper/degradation.piperine/index.html
4. ^ http://www.freepatentsonline.com/5095128.html , Preparation process for piperonal, US Patent No. 5095128
5. ^ http://www.erowid.org/archive/rhodium/chemistry/3base/piperonal.pepper/cleavage.piperic_acid/index.html

Categories: Organic acids

This page was last modified on 24 September 2016, at 09:57.

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