What is Piperine?

Piperine along with its isomer chavicine is an organic compound that either belongs to the lipid family that consists of either fat or fatlike substances or alkaloids that comprises nitrogenous compounds with specific physiological properties. This is one of the sharp-tasting elements in fruits like black pepper (Piper nigrum) and long pepper (Piper longum). The pungent taste of the peppers due to the presence of isomer chavicine which has the same molecular formula but a different molecular structure as that of piperine. The loss of pungency in peppers, when preserved for a long time is due to the slow conversion of chavicine into piperine. 


In black and white pepper, piperine content varies from 5-9%. Piperine is insoluble in water and due to this reason, it is typically extracted from pepper by using dichloromethane and other substituent organic solvents. Piperine can also be artificially prepared by treating concentrated alcoholic extract of pepper with an alcoholic solution of potassium hydroxide. This step is initiated to remove resin that actually contains chavicine which is a monomer of piperine. Then this solution is separated from its insoluble residue and is left to stand overnight. This step is done so that the alkaloids present in the solution start to crystallize to form piperine.

Piperine: Structure and Properties

The molecular formula of piperine is C17H19NO3 and its molecular structure is depicted as follows:-

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Piperine is basically an N-acyl pyridine molecule. In other words, the piperine structure depicts that piperidine is substituted by (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopentyl-1,3-dien-5-yl group attached with the nitrogen atom. Piperine is derived from (E,E)-piperic acid. This is basically an alkaloid that is extracted from the Piper nigrum plant and it acts as a NF-kappaB inhibitor. Other than an inhibitor, it also plays an important role as a plant metabolite, a human blood serum metabolism as well as a food component. Few chemical and physical properties of piperine are listed below.

Properties

Values 

Chemical formula

C17H19NO3

Molar mass

285.343 g/mol

density

1.193 g/cm3

Melting point

1300 C

Boiling point

decomposes

Solubility in water

40mg / l

Solubility in alcohol

1g /15ml

Solubility in ether

1g / 36ml

Solubility in chloroform

1g/1.7ml

XlogP3

3.5

Hydrogen bond donor count

0

Hydrogen bond acceptor count

3

Topological polar surface area

38.8Å2

Heavy atom count

21

complexity

412

Piperine Uses and Health Benefits

Piperine is widely used in modern herbal medicine. It also has a long history of use in primitive medical practices. These are very good sources of relief for chronic diseases like cough, nausea, headache and indigestion. It also has inflammatory properties. 

Piperine is considered to be very useful in health supplements as it helps in enhancing the bioavailability of some vitamins and minerals. Piperine is also used to inhibit p-glycoprotein and CYP3A4 enzymes in the human body that helps in metabolism and transport various metabolics throughout the body.it is also used to support a healthy breathing pattern, joint pains and ulcer in the stomach. 

Some of the Health Benefits of Piperine Can be Elaborated as Follows:-

Stress Management: Enzymes such as adrenaline and catecholamines are produced in the body in order to manage stress level in our mind. It has been observed that intake of piperine combined with vitamin C increases the release of these hormones and helps in managing stress level in a much better way.

Weight Management: Studies show that piperine also possesses some thermogenic properties that help increase the basal metabolic rate in the human body and thus helps in weight reduction by cutting down excess fatty cells.

Increase Bioavailability: Piperine has a unique property that helps in the assimilation of key nutrients in the human body that includes amino acids, beta carotene, Vitamin B6 and selenium.

Piperine Extract Method

  1. Extraction With Ethanol: 10 gms of pepper is extracted by initially mixing it with 150ml of 95% concentrated ethanol in Soxhlet extractor for 2 hours. Then the solution formed is filtered out and put over a water bath at 600C to get concentrated. Then 10ml of 10% concentrated potassium hydroxide is added to the filtrate with continuous stirring. The insoluble residue was filtered out from the alcoholic solution and then it is left to stand overnight to get the desired result.

  2. Extraction With Dichloromethane: 10 gms of ground pepper and 20ml of dichloromethane is taken in a round bottom flask and are refluxed for 20 minutes. After this, a condenser is attached and water is allowed to pass through it to condense the dichloromethane vapours. Later it is filtered with the help of a Buchner funnel once the flask is cooled, the filtrate is then treated with acetone and hexane.

  3. Extraction With Glacial Acetic Acid: 300 grams of glacial acetic acid is used for cold maceration of 25gms of black pepper. Then the extract is diluted with water and separated with chloroform using a separating funnel. Now the chloroform extract retrieved from the separating funnel is treated with 10% sodium bicarbonate followed by water. The pure extract is then concentrated in a rota evaporator and then dried over anhydrous sodium sulphate. Further purification of the extract is done using column chromatography with reagents, toluene and ethyl acetate in ratio 3:7 as a solvent. The resinous impurities that remain in the extract even after column chromatography is further washed with sodium hydroxide. This eventually takes away all the resinous impurities. This extract is then washed with water to remove excess sodium hydroxide that stayed back during the treatment. The extract is then crystallized by using diethyl ether.

FAQs (Frequently Asked Questions)

Q1. Is Black Pepper and Piperine Similar?

Ans. Black pepper is not exactly piperine but the pepper contains a bioactive component called piperine that has a monomer known as chavicine which is responsible for the pungent taste of peppers.

Q2. Which Solvents are Used in Separating Piperine?

Ans. Currently, there are three major solvents that are used throughout the world in the extraction of piperine from Piper longum and they are acetone, ethanol and hexane.

Q3. How is Piperine Made?

Ans. Since piperine is insoluble in water, therefore, it is not possible to extract it organically. There organic solvents like dichloromethane are used for the extraction of piperine.

Q4. What is the Meaning of Piperine?

Ans. In simple words, piperine is either an alkaloid that has a pungent taste to it and is found in the outer shells of berries and in the fruits of the Piper longum tree or it belongs to the lipid family.