(-)-cubebin is a lignan that consists of tetrahydrofuran-2-ol substituted by two 1,3-benzodioxol-5-ylmethyl groups at positions 3 and 4 respectively (the 2S,3R,4R stereoisomer). It is isolated from the leaves of Piper nigrum and exhibits analgesic, anti-inflammatory, antimicrobial and trypanocidal activities. It has a role as an antimicrobial agent, an analgesic, a trypanocidal drug, a histamine antagonist, an anti-inflammatory agent and a plant metabolite. It is a lignan, a secondary alcohol, a lactol, a member of benzodioxoles and a cyclic acetal.

Source: ChEBI

Identity
Molecular formula	C₂₀H₂₀O₆
Molecular weight	356.4 g/mol
IUPAC name	(2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
InChIKey	DIYWRNLYKJKHAM-MDOVXXIYSA-N
SMILES	C1[C@@H]([C@H]([C@H](O1)O)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5

Computed by PubChem (NCBI)

Synonyms: Cubebin, (-)-Cubebin, beta-cubebin, (2s,3r,4r)-3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydrofuran-2-ol, (2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol, (2S,3R,4R)-3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol, (3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol, .beta.-Cubebin, 2-Furanol, 3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-, (8R,8'R,9S)-cubebin

Products 18423-69-3

Cubebin

Related forms of this compound

Isomers (same molecular formula)