15297-98-0

Basic information

• Product Name: 3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
• Synonyms: 2H-Naphtho(1,2-b)pyran-5,6-dione, 3,4-dihydro-3-hydroxy-2,2-dimethyl-; 2H-naphtho[1,2-b]pyran-5,6-dione, 3,4-dihydro-3-hydroxy-2,2-dimethyl-
• CAS NO: 15297-98-0
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.2693
• Mol File: 15297-98-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 435.8°C at 760 mmHg
• Flash Point: 166.2°C
• Density: 1.34g/cm³
• Vapor Pressure: 2.28E-08mmHg at 25°C
• Refractive Index: 1.619
• CAS DataBase Reference: 3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione(15297-98-0)
• EPA Substance Registry System: 3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione(15297-98-0)

Safety Data

• Hazardous Substances Data: 15297-98-0(Hazardous Substances Data)

Upstream product

• 15298-00-7 dihydroxyhydrolapachol 
• 84-79-7 Lapachol 
• 870-63-3 prenyl bromide 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 195156-48-0 10,11-epoxy-lapachol 

Downstream Products

• 195156-50-4 Malonic acid tert-butyl ester 2,2-dimethyl-5,6-dioxo-3,4,5,6-tetrahydro-2H-benzo[h]chromen-3-yl ester 
• 15297-92-4 2,2-dimethyl-2H-benzo[g]chromene-5,10-dione 
• 4707-33-9 α-lapachone 
• 1383953-09-0 C₂₈H₂₂N₂O₃ 
• 1383953-63-6 C₂₈H₂₂N₂O₃ 
• 778585-88-9 5,6-dihydroxy-7,7-dimethyl-2-phenyl-6,7-dihydro-3H,5H-benzo[7,8]chromeno[5,6-b][1,4]oxazine-3-one 
• 778585-82-3 6-hydroxy-7,7-dimethyl-2-phenyl-6,7-dihydro-3H,5H-benzo[7,8]chromeno[5,6-b][1,4]oxazin-3-one 
• 778585-86-7 7,7-dimethyl-2-phenyl-3H,7H-benzo[7,8]-chromeno[5,6-b][1,4]oxazin-3-one 

Relevant articles and documents

Mitochondrial targeted β-lapachone induces mitochondrial dysfunction and catastrophic vacuolization in cancer cells

Mitochondria play important roles in tumor cell physiology and survival by providing energy and metabolites for proliferation and metastasis. As part of their oncogenic status, cancer cells frequently produce increased levels of mitochondrial-generated reactive oxygen species (ROS). However, extensive stimulation of ROS generation in mitochondria has been shown to be able to induce cancer cell death, and is one of the major mechanisms of action of many anticancer agents. We hypothesized that enhancing mitochondrial ROS generation through direct targeting of a ROS generator into mitochondria will exhibit tumor cell selectivity, as well as high efficacy in inducing cancer cell death. We thus synthesized a mitochondrial targeted version of β-lapachone (XJB-Lapachone) based on our XJB mitochondrial targeting platform. We found that the mitochondrial targeted β-lapachone is more efficient in inducing apoptosis compared to unconjugated β-lapachone, and the tumor cell selectivity is maintained. XJB-Lapachone also induced extensive cellular vacuolization and autophagy at a concentration not observed with unconjugated β-lapachone. Through characterization of mitochondrial function we revealed that XJB-Lapachone is indeed more capable of stimulating ROS generation in mitochondria, which led to a dramatic mitochondrial uncoupling and autophagic degradation of mitochondria. Taken together, we have demonstrated that targeting β-lapachone accomplishes higher efficacy through inducing ROS generation directly in mitochondria, resulting in extensive mitochondrial and cellular damage. XJB-Lapachone will thus help to establish a novel platform for the design of next generation mitochondrial targeted ROS generators for cancer therapy.

5-LIPOXYGENASE ANTAGONISTS

This invention relates to the treatment of conditions, such as cancer, associated with 5-lipoxygenase (5-LO) expression using β-lapachone compounds that inhibit 5-lipoxygenase (5-LO), such as β- lapachone and derivatives thereof. Methods of treatment of conditions associated with 5-lipoxygenase (5-LO) expression as well as medical uses of β-lapachone compounds in such methods are provided, as well as methods of selecting or prognosing cancer patients.

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.