Piperine, along with its isomer

chavicine Chavicine is an alkaloid found in black pepper and other species of the genus ''Piper''. It is one of the four geometric isomers of piperine Piperine, along with its isomer chavicine, is the alkaloid responsible for the pungency of black pep ...

, is the

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

responsible for the

pungency Pungency () refers to the taste of food commonly referred to as spiciness, hotness or heat, found in foods such as chili peppers. Highly pungent tastes may be experienced as unpleasant. The term piquancy () is sometimes applied to foods with a l ...

black pepper Black pepper (''Piper nigrum'') is a flowering vine in the family Piperaceae, cultivated for its fruit, known as a peppercorn, which is usually dried and used as a spice and seasoning. The fruit is a drupe (stonefruit) which is about in dia ...

and

long pepper Long pepper (''Piper longum''), sometimes called Indian long pepper or ''thippali'', is a flowering vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning. Long pepper has a taste simi ...

. It has been used in some forms of

traditional medicine Traditional medicine (also known as indigenous medicine or folk medicine) comprises medical aspects of traditional knowledge that developed over generations within the folk beliefs of various societies, including indigenous peoples, before the ...

Preparation

Due to its poor solubility in water, piperine is typically extracted from

by using organic solvents like dichloromethane. The amount of piperine varies from 1–2% in long pepper, to 5–10% in commercial white and black peppers. Piperine can also be prepared by treating a concentrated alcoholic extract of black pepper with an alcoholic solution of

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 exp ...

to remove resin (said to contain

, an isomer of piperine). The solution is decanted from the insoluble residue and left to stand overnight. During this period, the alkaloid slowly crystallizes from the solution. Piperine has been synthesized by the action of piperonoyl chloride on

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 ...

Reactions

Piperine forms salts only with strong acids. The platinichloride B₄·H₂PtCl₆ forms orange-red needles ("B" denotes one mole of the alkaloid base in this and the following formula). Iodine in

potassium iodide Potassium iodide is a chemical compound, medication, and dietary supplement. It is a medication used for treating hyperthyroidism, in radiation emergencies, and for protecting the thyroid gland when certain types of radiopharmaceuticals are u ...

added to an alcoholic solution of the base in the presence of a little

hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...

gives a characteristic periodide, B₂·HI·I₂, crystallizing in steel-blue needles with

melting point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depen ...

145 °C. Piperine can be hydrolyzed by an alkali into

and

piperic acid Piperic acid is a chemical often obtained by the base-hydrolysis of the alkaloid piperine from black pepper, followed by acidification of the corresponding salt. Piperic acid is an intermediate in the synthesis of other compounds such as piperona ...

History

Piperine was discovered in 1819 by Hans Christian Ørsted, who isolated it from the fruits of ''

Piper nigrum Black pepper (''Piper nigrum'') is a flowering vine in the family Piperaceae, cultivated for its fruit, known as a peppercorn, which is usually dried and used as a spice and seasoning. The fruit is a drupe (stonefruit) which is about in diame ...

'', the source plant of both black and white pepper. Piperine was also found in '' Piper longum'' and '' Piper officinarum'' (Miq.) C. DC. (=''Piper retrofractum'' Vahl), two species called "long pepper".

Biochemistry and medicinal aspects

A component of

by piperine results from activation of the heat- and acidity-sensing

transient receptor potential channel Transient receptor potential channels (TRP channels) are a group of ion channels located mostly on the plasma membrane of numerous animal cell types. Most of these are grouped into two broad groups: Group 1 includes TRPC ( "C" for canonical), TR ...

ion channels,

TRPV1 The transient receptor potential cation channel subfamily V member 1 (TrpV1), also known as the capsaicin receptor and the vanilloid receptor 1, is a protein that, in humans, is encoded by the ''TRPV1'' gene. It was the first isolated member of th ...

and

TRPA1 Transient receptor potential cation channel, subfamily A, member 1, also known as transient receptor potential ankyrin 1, TRPA1, or The Wasabi Receptor, is a protein that in humans is encoded by the ''TRPA1'' (and in mice and rats by the ''Trpa1' ...

, on nociceptors, the pain-sensing nerve cells. Piperine is under preliminary research for its potential to affect

bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. Ho ...

of other compounds in food and dietary supplements, such as a possible effect on the

curcumin Curcumin is a bright yellow chemical produced by plants of the ''Curcuma longa'' species. It is the principal curcuminoid of turmeric (''Curcuma longa''), a member of the ginger family, Zingiberaceae. It is sold as a herbal supplement, cosmet ...

References

{{Authority control CYP3A4 inhibitors Piperidine alkaloids Pungent flavors Monoamine oxidase inhibitors Carboxamides Benzodioxoles Polyenes Enones

Preparation

Reactions

History

Biochemistry and medicinal aspects

See also

References