Piperine Chemical Properties

Melting point:

131-135 °C(lit.)

Boiling point:

427.77°C (rough estimate)

Density 

1.0864 (rough estimate)

refractive index 

1.5400 (estimate)

FEMA 

2909 | PIPERINE

storage temp. 

Sealed in dry,Room Temperature

solubility 

Slightly soluble in water, 10% soluble in alcohol, soluble only in certain oils

form 

Crystalline Powder

pka

12.22(at 18℃)

color 

Off-white to tan or yellow-tan

Odor

at 1.00 % in propylene glycol. pepper animal

Odor Type

spicy

Water Solubility 

40 mg/L (18 ºC)

JECFA Number

1600

Merck 

14,7472

BRN 

90741

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

MXXWOMGUGJBKIW-YPCIICBESA-N

LogP

2.66

CAS DataBase Reference

94-62-2(CAS DataBase Reference)

NIST Chemistry Reference

Piperine(94-62-2)

EPA Substance Registry System

2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E,4E)- (94-62-2)

Safety Information

Hazard Codes 

Xn,Xi,N

Risk Statements 

22-21/22-20/21/22-51/53

Safety Statements 

22-24/25-36/37-36-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

RTECS 

TN2321500

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29399990

Toxicity

LD50 orally in Rabbit: 514 mg/kg

MSDS

• Language:English Provider:(E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-piperidine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Piperine Usage And Synthesis

Description

Piperine is an alkaloid responsible for the taste and fl avor of pepper. In pure form it exists as a yellow to pale-yellow crystal, with a burning taste and pungent order. It is found naturally in plants in the Piperaceae family, particularly Piper nigrum (black pepper) and Piper longum (Indian long pepper). Piper nigrum is a perennial woody vine that grows to approximately 30 feet. It produces spikelike flowers that hold berries called peppercorns.

Chemical Properties

light yellow powder

Chemical Properties

Piperine is odorless. It is tasteless at first, but develops a burning aftertaste of pepper.

Occurrence

Reported found in black pepper; also in Piper longum, Piper officinarum, Piper lowong BI., Piper famechoni, Piper chaba and the leaves of Rhododendron fauriae var. rupescens.

History

Hans Christian Oersted (1777 1851) isolated piperine from black pepper in 1819 and published his findings in 1820. Oersted extracted a resin from pepper plants with alcohol, formed a soluble saltby adding hydrochloric acid with alcohol, and then separated piperine from solution by precipitation and distillation. In 1882, Leopold Rügheimer (1850 1917) synthesized piperine from piperinic acid chloride and piperidine. The complete synthesis of piperine was reported in 1894 by Albert Ladenburg (1842 1911) and M. Scholtz. Ladenburg and Scholtz used piperonal (C8H6O3) and acetaldehyde (CH3CHO) to produce piperinic acid (C12H10O4), which was then reacted with thionyl chloride (COCl2) and piperidine (C5H11N) to produce piperine.

Uses

Piperine is used in granular formulations as a pesticide against small animals such as dogs, cats, skunks, raccoons, and squirrels. Piperine pesticides are nontoxic and operate as a repellant when animals smell or test them. Piperine is also incorporated with other compounds to make insecticides; it is effective against houseflies, lice, and various other pests.
Piperine has been used medicinally for thousands of years and this continues today. It is used to treat asthma and chronic bronchitis. It also has putative analgesic and antiinfl ammatory properties that stem from its antioxidant properties. Research is examining the use of piperine in treating malaria. Antiepilepsirine is a derivative of piperine that is used to treat different types of epilepsy, especially in China. A current area of interest is the efficacy of piperine in increasing the bioavailability of certain nutrients and drugs. It is thought to possibly aid digestion and increase the absorption in the digestive tract of numerous drugs used as cancer treatments, antihistamines, steroidal inflammation reducers, and antibiotics.

Uses

analeptic, antibacterial

Uses

The alkaloid which gives pepper its spiciness, and has been used as an organic insecticide.

Uses

A black pepper extract TRPV1 activator.
It finds use in flavor compositions, not only as ingredient in artificial Black Pepper, but also in various spice blends, and as an additive to the flavor composition used in "Celery Soda" (a carbonated beverage of sweet, but pungent Celery flavor, sometimes used as an appetizer).

Definition

ChEBI: Piperine is a N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum. It has a role as a NF-kappaB inhibitor, a plant metabolite, a food component and a human blood serum metabolite. It is a member of benzodioxoles, a N-acylpiperidine, a piperidine alkaloid and a tertiary carboxamide. It is functionally related to an (E,E)-piperic acid.

Preparation

From piperoyl chloride and piperidine.

Safety Profile

Poison by ingestion and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Piperine crystallises as light yellow crystals from EtOH or EtOAc (m 132o), aqueous EtOH (m 128-129o), Et2O (m129o), or*benzene/ligroin. [Beilstein 20 H 79, 20 I 23, 20 II 53, 20 III/IV 1341, 20/3 V 469.]

References

Oersred., Schweigger's Journal, 29, 80 (1819)
Fliickiger, Hanbury., Pharmacographica, 584 London (1879)
Stenhouse., Pharm. J., 14,363 (1855)
Cazeneuve, Caillot., Bull. Soc. Chim. Fr., 27,291 (1877)
Riigheimer., Ber., 15, 1391 (1882)
Peinemann., Arch. Pharm., 234, 245 (1896)
Newman., Chem. Products, 16,379 (1953)

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