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外観
白色～黄褐色, 粉末
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溶解性
1g/15mg アルコール, 1g/1.7ml クロロホルム, 1g/36ml エーテル。40mg/l 水(18℃)エタノール及びアセトンに溶け、水にほとんど溶けない。
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解説
ピペリン，コショウ科黒コショウPiper nigrumあるいはP.longum，P.clusiiの主成分．中性化合物であるが，構造上ピリジンアルカロイドに分類される．柱状晶．融点130 ℃．pK 12.22(18 ℃)．最初は無味，しだいに焼くような苦味を呈する．水に不溶，有機溶媒に可溶．ブランデーの辛味をつけるのに欠かせない物質である．健胃剤として用いられるが，殺虫作用がある．ヒトには無害．本品0.05％ とピレトリン0.01％ の混合物は，イエバエに対して0.1％ のピレトリンよりも強力な殺虫剤となる．
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用途
薬理・生理作用研究用。
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説明
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.
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化学的特性
Piperine is odorless. It is tasteless at first, but develops a burning aftertaste of pepper.
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天然物の起源
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.
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来歴
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.
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使用
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.
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製造方法
From piperoyl chloride and piperidine.
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安全性プロファイル
Poison by ingestion and
intraperitoneal routes. An experimental
teratogen. Experimental reproductive
effects. When heated to decomposition it
emits toxic fumes of NOx.
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純化方法
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.]
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参考文献
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)
