18423-69-3

Basic information

• Product Name: CUBEBIN
• Synonyms: CUBEBIN;tetrahydro-3,4-dipiperonylfuran-2-ol;CUBEBIN(RG);3,4-Bis[(1,3-benzodioxol-5-yl)methyl]tetrahydrofuran-2-ol;[[3R,(-)]-3α,4β-Bis[(1,3-benzodioxole-5-yl)methyl]tetrahydrofuran]-2-ol;.beta.-Cubebin;2-Furanol, 3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-, (2S,3R,4R)-;2-Furanol, tetrahydro-3,4-dipiperonyl-
• CAS NO: 18423-69-3
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.37
• EINECS: 242-300-6
• Product Categories: Heterocycles
• Mol File: 18423-69-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 131-132°C
• Boiling Point: 409.21°C (rough estimate)
• Flash Point: 272.4°C
• Appearance: /
• Density: 1.2029 (rough estimate)
• Vapor Pressure: 6.29E-12mmHg at 25°C
• Refractive Index: 1.4450 (estimate)
• CAS DataBase Reference: CUBEBIN(CAS DataBase Reference)
• NIST Chemistry Reference: CUBEBIN(18423-69-3)
• EPA Substance Registry System: CUBEBIN(18423-69-3)

Safety Data

• Hazardous Substances Data: 18423-69-3(Hazardous Substances Data)

Usage

Description

CUBEBIN, also known as a lignan, is a compound 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 various beneficial properties, including analgesic, anti-inflammatory, antimicrobial, and trypanocidal activities.

Uses

Used in Pharmaceutical Industry:
CUBEBIN is used as a pharmaceutical compound for its analgesic, anti-inflammatory, antimicrobial, and trypanocidal properties. Its diverse range of activities makes it a promising candidate for the development of new drugs and treatments for various health conditions.
Used in Traditional Medicine:
CUBEBIN is also used in traditional medicine, particularly in the treatment of pain and inflammation. Its natural origin and proven efficacy make it a valuable component in the development of alternative and complementary therapies.
Used in Cosmetics Industry:
Due to its antimicrobial properties, CUBEBIN can be used in the cosmetics industry as a natural preservative or as an active ingredient in products designed to promote skin health and prevent infections.
Used in Agricultural Industry:
CUBEBIN's antimicrobial and trypanocidal activities can be harnessed in the agricultural industry for the development of natural pesticides and treatments for various plant and animal diseases, promoting sustainable and eco-friendly farming practices.

InChI:InChI=1/C20H20O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15,20-21H,5-6,9-11H2

Upstream product

• 26543-89-5 (-)-hinokinin 
• 17187-77-8 (R)-(+)-3-piperonyl-4-butanolide 
• 120-57-0 piperonal 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 120040-64-4 (+)-(2S,3S,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<<3,4-(methylenedioxy)phenyl>bis(phenylthio)methyl>tetrahydrofuran 
• 120040-58-6 Benzo[1,3]dioxol-5-yl-((R)-5-benzyloxy-2,5-dihydro-furan-3-yl)-methanol 
• 120040-59-7 (-)-(2R)-2-(Benzyloxy)-2,5-dihydro-4-<3,4-(methylenedioxy)benzoyl>furan 
• 104322-41-0 (+)-(2R)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde 
• 6302-93-8 5-[Bis(phenylsulfanyl)methyl]-1,3-benzodioxole 

Downstream Products

• 26543-89-5 (-)-hinokinin 
• 81410-45-9 (8R,8'R-)8,8'-bis-(3'4'-methylenedioxybenzyl)-tetrahydrofuran (-)-dehydroxycubebin 

Related news

Analgesic and anti-inflammatory activities evaluation of (-)-O-acetyl, (-)-O-methyl, (-)-O-dimethylethylamine CUBEBIN (cas 18423-69-3) and their preparation from (-)-CUBEBIN (cas 18423-69-3)09/06/2019

The anti-inflammatory and antinociceptive effects of the acetylated (2), methylated (3) and aminated (4) derivatives of cubebin (1), obtained by its reaction with acetic anhydride, methyl iodide and dimethylethylamine chloride, respectively, were investigated, using different animal models. The ...detailed

Anticancer activity studies of CUBEBIN (cas 18423-69-3) isolated from Piper cubeba and its synthetic derivatives08/31/2019

(−)-Cubebin, isolated from the seeds of Piper cubeba, and its five different types of derivatives (a total of 17), with varying functionalities, were tested for their in vitro anticancer activity against six human cancer cell lines (A549, K562, SiHa, KB, HCT116 and HT29) using MTT assay. Cubebin...detailed

Relevant articles and documents

Synthesis method and application of cubebin

The invention discloses a synthesis method of cubebin, which comprises the following steps: using 1,3-benzodioxole-5-carboxaldehyde and malonic acid as initial raw materials to generate 1,3-benzodioxole-5-propanoic acid, reacting the 1,3-benzodioxole-5-propanoic acid with oxalyl chloride to generate 1,3-benzodioxole-5-propionyl chloride, then reacting the 1,3-benzodioxole-5-propionyl chloride with (S)-4-benzyl-2-oxazolidinone to generate corresponding amide, reacting a product with bromopropyl to generate corresponding olefin, generating a corresponding carbonyl compound under the catalysis of a combined oxidant OsO4/NMO, using the carbonyl compound to prepare a corresponding hydroxyl compound, oxidizing the hydroxyl compound into a lactone compound by using a Fetizon reagent, reacting the lactone compound with 5-(bromomethyl)-1,3-benzodioxole, and finally, reducing the product by using diisobutylaluminium hydride to obtain cubebin. The invention further discloses application of cubebin in sedative and peaceful sleep. The invention provides a potential therapeutic drug for calming and sleeping.

General Conjugate-Addition Method for the Synthesis of Enantiomerically Pure Lignans. Total Synthesis of (-)- and (+)-Burseran, (-)-Dehydroxycubebin, (-)-Trichostin, (-)-Cubebin, (-)-5''-Methoxyhinokinin, and (-)-Hinokinin

Conjugate addition of benzylic diphenyldithioacetal anions to enantiomerically pure (-)-(2R)-and (+)-(2S)-(benzyloxy)-2,5-dihydro-4-furan (2 r and 2 s) gave complete lignan skeletons of the dibenzylbutane class.Desulfurization followed by hydrogenolysis and, when appropriate, oxidation gave the title enantiomerically pure > 99 percent ee) lignans 45 - 50 in 24 - 35 percent overall yields from 2 r and 2 s.