Cubebin

Title: Cubebin
CAS Registry Number: 18423-69-3
CAS Name: 3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol
Additional Names: tetrahydro-3,4-dipiperonyl-2-furanol; 5-hydroxy-3,4-bis(3,4-methylenedioxybenzyl)tetrahydrofuran
Molecular Formula: C20H20O6
Molecular Weight: 356.37
Percent Composition: C 67.41%, H 5.66%, O 26.94%
Literature References: From cubeb. Isoln: Capitaine, Soubeiran, Ann. 31, 190 (1839). Structure: Haworth, Kelly, Chem. Ind. (London) 1936, 901; Haensel et al., Arch. Pharm. 300, 559 (1967). Synthesis: Batterbee et al., J. Chem. Soc. C 1969, 2470.
Properties: Slender prisms from methanol, mp 131-132°. [a]D14 -17° (acetone). Practically insol in water. Sol in alcohol, chloroform, ether.
Melting point: mp 131-132°
Optical Rotation: [a]D14 -17° (acetone)
NOTE: "Cubebine" is the French designation for ethereal extract of cubeb.
Cucurbitacins Cuelure Cumene Cumic Acid Cumic Alcohol

Cubeb
Scientific classification
Kingdom: Plantae
(unranked): Angiosperms
(unranked): Magnoliids
Order: Piperales
Family: Piperaceae
Genus: Piper
Species: P. cubeba
Binomial name
Piper cubeba
L.f.

Cubeb (Piper cubeba), or tailed pepper, or shital chini / kabab chini in Hindi is a plant in genus Piper, cultivated for its fruit and essential oil. It is mostly grown in Java and Sumatra, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and carefully dried. Commercial cubebs consist of the dried berries, similar in appearance to black pepper, but with stalks attached – the "tails" in "tailed pepper". The dried pericarp is wrinkled, and its color ranges from grayish-brown to black. The seed is hard, white and oily. The odor of cubebs is described as agreeable and aromatic and the taste as pungent, acrid, slightly bitter and persistent. It has been described as tasting like allspice, or like a cross between allspice and black pepper.

Cubeb came to Europe via India through the trade with the Arabs. The name cubeb comes from Arabic kabāba (كبابة‎), which is of unknown origin,[1] by way of Old French quibibes.[2] Cubeb is mentioned in alchemical writings by its Arabic name. In his Theatrum Botanicum, John Parkinson tells that the king of Portugal prohibited the sale of cubeb in order to promote black pepper (Piper nigrum) around 1640. It experienced a brief resurgence in 19th-century Europe for medicinal uses, but has practically vanished from the European market since. It continues to be used as a flavoring agent for gins and cigarettes in the West, and as a seasoning for food in Indonesia.