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Piperic acid is a chemical often obtained by the base-
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
of the
alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...
piperine Piperine, possibly along with its isomer chavicine, is the compound responsible for the pungency of black pepper and long pepper via activation of TRPV1. It has been used in some forms of traditional medicine. Preparation Extraction Due t ...
from
black pepper Black pepper (''Piper nigrum'') is a flowering vine in the family Piperaceae, cultivated for its fruit (the peppercorn), which is usually dried and used as a spice and seasoning. The fruit is a drupe (stonefruit) which is about in diameter ...
, followed by
acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...
ification of the corresponding
salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...
. Piperic acid is an intermediate in the synthesis of other compounds such as
piperonal Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors.Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe a ...
, and as-such may be used to produce
fragrances An aroma compound, also known as an odorant, aroma, fragrance, flavoring or flavor, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficien ...
,
perfumes Perfume (, ) is a mixture of fragrance, fragrant essential oils or aroma compounds (fragrances), Fixative (perfumery), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agre ...
flavorants and
drugs A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via inhalation, injection, smoking, ingestio ...
as well as other useful compounds.


Preparation

Piperic acid can be prepared from the commercially available alkaloid
piperine Piperine, possibly along with its isomer chavicine, is the compound responsible for the pungency of black pepper and long pepper via activation of TRPV1. It has been used in some forms of traditional medicine. Preparation Extraction Due t ...
, a cyclic
amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...
containing a
piperidine Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor de ...
group, by reacting it with a
hydroxide Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It ...
such as
potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which utili ...
, then acidifying the formed piperate salt with
hydrochloric acid Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...
or another acid. The
toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...
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 Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, which dissolves in water as K+ and ions to give an intensely pink to purple solution. Potassium permanganate is widely us ...
or
ozone Ozone () (or trioxygen) is an Inorganic compound, inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , break ...
, or a halogen such as
bromine Bromine is a chemical element; it has chemical symbol, symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between th ...
followed by
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...
causes oxidative cleavage of the double-bonds, yielding
piperonal Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors.Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe a ...
and piperonylic acid.{{Cite patent , country = US , title = Preparation process for piperonal , number = 5095128 Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals. On reduction with sodium
amalgam Amalgam most commonly refers to: * Amalgam (chemistry), mercury alloy * Amalgam (dentistry), material of silver tooth fillings ** Bonded amalgam, used in dentistry Amalgam may also refer to: * Amalgam Comics, a publisher * Amalgam Digital, an in ...
piperic acid forms α- and β- dihydropiperic acid, C12H12O4, and the latter can take up two further atoms of hydrogen to produce tetrahydropiperic acid.


See also

*
Piperonal Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors.Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe a ...
*
Piperine Piperine, possibly along with its isomer chavicine, is the compound responsible for the pungency of black pepper and long pepper via activation of TRPV1. It has been used in some forms of traditional medicine. Preparation Extraction Due t ...
*
Safrole Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among ot ...
*
Isosafrole Isosafrole is an organic compound that is used in the fragrance industry. Structurally, the molecule is related to allylbenzene, a type of aromatic organic chemical. Its fragrance is reminiscent of anise or licorice. It is found in small amount ...
* Sesamol *
Piperonyl butoxide Piperonyl butoxide (PBO) is a pale yellow to light brown liquidNational Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Tr ...
*
Cinnamic acid Cinnamic acid is an organic compound with the formula phenyl, C6H5-CH=CH-Carboxylic acid, COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxy ...


References

Carboxylic acids Benzodioxoles