L2037

Sigma-Aldrich

β-Lapachone

≥98% (TLC)

Empirical Formula (Hill Notation):
C15H14O3
CAS Number:
Molecular Weight:
242.27
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

biological source

synthetic (organic)

Quality Level

assay

≥98% (TLC)

form

powder

SMILES string

CC1(C)CCC2=C(O1)c3ccccc3C(=O)C2=O

InChI

1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3

InChI key

QZPQTZZNNJUOLS-UHFFFAOYSA-N

Biochem/physiol Actions

β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties. Induces apoptosis in HL-60 and human prostate cancer cells.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Myungwon Choi et al.
Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer, 31(2), 87-94 (2012-12-12)
In this study, we investigated the effects of β-lapachone (β-lap) on the production of cytokines in C57BL/6 mice. The culture supernatants of splenocytes exposed to β-lap plus lipopolysaccharide or concanavalin A (Con A) were harvested to determine Th1 (tumor necrosis...
Isabella M F Cavalcanti et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 44(3), 332-340 (2011-09-06)
The aim of this study was to encapsulate lapachone (β-lap) or inclusion complex (β-lap:HPβ-CD) in liposomes and to evaluate their physicochemical characteristics. In addition, the investigation of the main aspects of the interaction between β-lap and 2-hydroxypropyl-β-cyclodextrin (HPβ-CD), using both...
C J Li et al.
The Journal of biological chemistry, 268(30), 22463-22468 (1993-10-25)
beta-Lapachone is a plant product that has been found to have many pharmacological effects. To date, very little is known about its biochemical target. In this study, we found that beta-lapachone inhibits the catalytic activity of topoisomerase I from calf...
Moon-Taek Park et al.
PloS one, 6(10), e25976-e25976 (2011-10-15)
β-lapachone (β-lap), has been known to cause NQO1-dependnet death in cancer cells and sensitize cancer cells to ionizing radiation (IR). We investigated the mechanisms underlying the radiosensitization caused by β-lap. β-lap enhanced the effect of IR to cause clonogenic cells...
David Siegel et al.
Biochemical pharmacology, 83(8), 1033-1040 (2012-01-03)
Quinones represent a large and diverse class of antitumor drugs and many quinones are approved for clinical use or are currently undergoing evaluation in clinical trials. For many quinones reduction to the hydroquinone has been shown to play a key...

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