Пиперин

Описание

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.

Химические свойства

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

Вхождение

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.

История

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.

Использование

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.

Подготовка

From piperoyl chloride and piperidine.

Профиль безопасности

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

Методы очистки

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.]

использованная литература

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)