26543-89-5

Basic information

• Product Name: Cubebinolide
• Synonyms: Cubebinolide;(-)-Hinokinin;(3R)-3α,4β-Bis(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one;(3R,4R)-3,4-Bis(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one;3α,4β-Dipiperonyltetrahydrofuran-2-one;Hinokinin
• CAS NO: 26543-89-5
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.35332
• Mol File: 26543-89-5.mol
• Article Data: 31

Chemical Properties

• Melting Point: 63-64 °C
• Boiling Point: 549°Cat760mmHg
• Flash Point: 243.2°C
• Appearance: /
• Density: 1.388g/cm³
• Vapor Pressure: 4.2E-12mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: Cubebinolide(CAS DataBase Reference)
• NIST Chemistry Reference: Cubebinolide(26543-89-5)
• EPA Substance Registry System: Cubebinolide(26543-89-5)

Safety Data

• Hazardous Substances Data: 26543-89-5(Hazardous Substances Data)

Usage

Definition

ChEBI: A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 3,4-methylenedioxybenzyl group at positions 3 and 4 (the 3R,4R-diastereoisomer).

InChI:InChI=1/C20H18O6/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/h1-4,7-8,14-15H,5-6,9-11H2/t14-,15+/m0/s1

Upstream product

• 26543-90-8 (+)-Isohinokinin 
• 24563-03-9 (-)-dihydrocubebin 
• 119098-95-2 (-)-(2R,3R)-2-(3',4'-dihydroxybenzyl)-3-(3'',4''-dihydroxybenzyl)butyrolactone 
• 74-95-3 1,1-dibromomethane 
• 18423-69-3 (8R,8'R)-cubebin 
• 75-11-6 diiodomethane 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 495-76-1 piperonol 
• 22180-30-9 Diethyl α-piperonylmalonate 
• 24562-97-8 (E)-4-((benzo[d][1,3]dioxol-6-yl)methyl)-3-((benzo[d][1,3]dioxol-6-yl)methylene)dihy-drofuran-2(3H)-one 
• 53762-69-9 5-(2-iodoethyl)-3,4-methylenedioxybenzene 
• 1383105-45-0 dimethyl 2-(2-(3,4-methylenedioxyphenyl)ethylidene)malonate 
• 1383105-47-2 dimethyl 2-(2-(3,4-methylenedioxyphenyl)-1-(pivaloyloxymethyl)ethyl)malonate 
• 1383105-49-4 methyl 4-(3,4-methylenedioxyphenylmethyl)-2-oxotetrahydrofuran-3-carboxylate 

Downstream Products

• 26543-90-8 (+)-Isohinokinin 
• 81410-43-7 ariensin 
• 18423-69-3 (-)-(8R,8'R,9R)-cubebin 
• 98819-09-1 polygamain 
• 18423-69-3 (8R,8'R)-cubebin 

Relevant articles and documents

(-)-Hinokinin causes antigenotoxicity but not genotoxicity in peripheral blood of Wistar rats

(-)-Hinokinin, a dibenzylbutyrolactone lignan, exhibits significant trypanocidal activity both in vitro and in vivo, and was obtained by partial synthesis from (-)-cubebin isolated from the dry seeds of Piper cubeba. Considering the good trypanocidal activity of (-)-hinokinin, as well as its potential for the development of new drugs, it is extremely important to evaluate its possible mutagenic activity to allow its safe use in humans. In the present study, we evaluated the antimutagenic effect of (-)-hinokinin on the chromosome damage induced by the chemotherapeutic agent doxorubicin (DXR). The test system employed was the analysis of micronucleated polychromatic erythrocytes in peripheral blood of Wistar rats. Additionally, the antioxidant activity of (-)-hinokinin was evaluated in in vitro experiments by measuring the production of hydrogen peroxide and other peroxides. Our results showed that animals treated with different doses of (-)-hinokinin (10, 20, and 40 mg/kg b.w.) exhibited micronucleated cell frequencies similar to that of the negative control. In addition, treatment with combinations of (-)-hinokinin and DXR resulted in lower micronucleated cell frequencies than those observed for animals treated with DXR alone. The present study shows that (-)-hinokinin not only has no genotoxic effect, but is also effective in reducing the chromosome damage induced by DXR. (-)-Hinokinin exerted a significant antioxidant effect on parasite mitochondria in the protocol used, which might be one possible mechanism by which this compound may exert a protective effect on the chromosome damage induced by the free radicals generated by DXR.

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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.

Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans

(?)-Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Reported here is a short chemoenzymatic total synthesis of (?)-podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C?C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion. This strategy allows gram-scale access to (?)-deoxypodophyllotoxin and is readily adaptable to the preparation of related aryltetralin lignans.