15297-93-5

Basic information

• Product Name: 3,4-Dehydro-β-lapachone
• Synonyms: 2,2-Dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione;3,4-Dehydro-β-lapachone;Dehydro-β-lapachone
• CAS NO: 15297-93-5
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25398
• Mol File: 15297-93-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 404.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3,4-Dehydro-β-lapachone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dehydro-β-lapachone(15297-93-5)
• EPA Substance Registry System: 3,4-Dehydro-β-lapachone(15297-93-5)

Safety Data

• Hazardous Substances Data: 15297-93-5(Hazardous Substances Data)

Upstream product

• 15297-92-4 2,2-dimethyl-2H-benzo[g]chromene-5,10-dione 
• 4707-32-8 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 
• 84-79-7 Lapachol 

Relevant articles and documents

Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

Naphthoquinones are considered privileged structures for anticancer drug molecules. The Heck reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with 1-bromo-3-methyl-2-butene offered easy access to lapachol. Several naturally occurring linear and angular heterocyclic quinoids (α-lapachone, β-lapachone, dunnione, and related analogues) were prepared from lapachol. Furthermore, we demonstrated that the synthetic naphthoquinones inhibit cell proliferation in human leukemia HL-60 cells. In particular, angular-type derivatives were found to possess moderate cytotoxicity and to elevate the levels of intracellular glutathione disulfide (GSSG). Our work highlights the significant potential of naturally occurring angular-series naphthoquinones as antileukemic agents.

PHARMACEUTICAL COMPOSITION FOR TREATMENT AND PREVENTION OF RESTENOSIS

Provided is a pharmaceutical composition for the treatment and/or prevention of restenosis including (a) a therapeutically effective amount of a particular compound represented by Formula 1 and 2, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

Conversion of lapachol to array of furano and pyranonaphthoquinone congeners

Chemical conversion of lapachol to α-lapachone, β-lapachone, dehydro-α-lapachone, dehydroiso-α-lapachone and dehydroiso-β- lapachone by reaction with aqueous NaNO2 and glacial AcOH; rhinacanthin-A, stenocarpoquinone-A, stenocarpoquinone-B and its isomer by reaction with meta-chloroperbenzoic acid at 0° for 30 min and dehydro-α-lapachone and dehydro-β-lapachone at 25° for 4 h respectively and di- and tribromo derivatives by reaction with Br2 in chloroform has been reviewed. In most of these reactions prenyl chain cyclises into an oxygen function to give a number of furano and pyrano-naphthoquinone derivatives. Some of these naphthoquinones co-occur with lapachol in the same plant species.