Piperine, along with its
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
...
chavicine, is the
alkaloid
Alkaloids are a class of basic
BASIC (Beginners' All-purpose Symbolic Instruction Code) is a family of general-purpose, high-level programming languages designed for ease of use. The original version was created by John G. Kemeny and Th ...
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 ...
of
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 di ...
and
long pepper. 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 th ...
.
Preparation
Due to its poor solubility in water, piperine is typically extracted from
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 di ...
by using organic solvents like
dichloromethane
Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible wit ...
. 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 expl ...
to remove resin (said to contain
chavicine, 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 compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless ...
.
Reactions
Piperine forms salts only with strong acids. The
platinichloride B
4·H
2PtCl
6 forms orange-red needles ("B" denotes one mole of the alkaloid base in this and the following formula).
Iodine
Iodine is a chemical element with the Symbol (chemistry), symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions that melts to form a deep violet liquid at , ...
in
potassium iodide 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. It is a component of the gastric acid in the dig ...
gives a characteristic periodide, B
2·HI·I
2, 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 depends ...
145 °C.
Piperine can be
hydrolyzed by an alkali into
piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless ...
and
piperic acid.
History
Piperine was discovered in 1819 by
Hans Christian Ørsted
Hans Christian Ørsted ( , ; often rendered Oersted in English; 14 August 17779 March 1851) was a Danish physicist and chemist who discovered that electric currents create magnetic fields, which was the first connection found between electricity ...
, who isolated it from the fruits of ''
Piper nigrum'', the source plant of both black and white pepper. Piperine was also found in ''
Piper longum'' and ''
Piper officinarum
''Piper retrofractum'', the Balinese long pepper or Javanese long pepper, is a flowering vine in the family ''Piperaceae'', cultivated for its fruit, which is usually dried and used as a spice and seasoning. The fruit of ''Piper retrofractum'' is ...
'' (Miq.) C. DC. (=''Piper retrofractum'' Vahl), two species called "long pepper".
Biochemistry and medicinal aspects
A component of
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 ...
by piperine results from activation of the heat- and acidity-sensing
transient receptor potential channel ion channel
Ion channels are pore-forming membrane proteins that allow ions to pass through the channel pore. Their functions include establishing a resting membrane potential, shaping action potentials and other electrical signals by gating the flow of ...
s,
TRPV1 and
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%. ...
of other compounds in food and
dietary supplement
A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in orde ...
s, such as a possible effect on the
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%. ...
of
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, cos ...
.
See also
*
Piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless ...
, a cyclic six-membered
amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent su ...
that results from
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, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolysis ...
of piperine
*
Piperic acid, the
carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyl ...
also derived from hydrolysis of piperine
*
Capsaicin
Capsaicin (8-methyl-''N''-vanillyl-6-nonenamide) ( or ) is an active component of chili peppers, which are plants belonging to the genus ''Capsicum''. It is a chemical irritant for mammals, including humans, and produces a sensation of burning ...
, the active piquant chemical in
chili pepper
Chili peppers (also chile, chile pepper, chilli pepper, or chilli), from Nahuatl '' chīlli'' (), are varieties of the berry-fruit of plants from the genus '' Capsicum'', which are members of the nightshade family Solanaceae, cultivated for ...
s
*
Allyl isothiocyanate, the active
piquant chemical in
mustard,
radish
The radish ('' Raphanus raphanistrum'' subsp. ''sativus'') is an edible root vegetable of the family Brassicaceae that was domesticated in Asia prior to Roman times.
Radishes are grown and consumed throughout the world, being mostly eaten ra ...
es,
horseradish
Horseradish (''Armoracia rusticana'', syn. ''Cochlearia armoracia'') is a perennial plant of the family Brassicaceae (which also includes mustard, wasabi, broccoli, cabbage, and radish). It is a root vegetable, cultivated and used worldwide ...
, and
wasabi
Wasabi ( Japanese: , , or , ; ''Eutrema japonicum'' or ''Wasabia japonica'') or Japanese horseradish is a plant of the family Brassicaceae, which also includes horseradish and mustard in other genera. The plant is native to Japan and the Russ ...
*
Allicin, the active piquant flavor chemical in raw
garlic
Garlic (''Allium sativum'') is a species of bulbous flowering plant in the genus ''Allium''. Its close relatives include the onion, shallot, leek, chive, Welsh onion and Chinese onion. It is native to South Asia, Central Asia and northe ...
and
onions (see those articles for discussion of other chemicals in them relating to pungency, and eye irritation)
*
Ilepcimide
Ilepcimide, also known as antiepilepserine, is an anticonvulsant. It is a piperidine derivative that was first synthesized by Chinese researchers as an analogue of piperine, the main pungent compound and phytochemical of black pepper (and of othe ...
*
Piperlongumine
References
{{Authority control
CYP3A4 inhibitors
Piperidine alkaloids
Pungent flavors
Monoamine oxidase inhibitors
Carboxamides
Benzodioxoles
Polyenes
Enones