L2037

β-Lapachone

≥98% (TLC)

• Synonym(s): ARQ 501, NSC 26326, NSC 629749, SL 11001
• Empirical Formula (Hill Notation): C₁₅H₁₄O₃
• CAS Number: 4707-32-8
• Molecular Weight: 242.27
• MDL number: MFCD01712233
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278512
• NACRES: NA.77

Properties

• biological source: synthetic (organic)
• 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

Description

Application

β-Lapachone has been used:

• as an anticancer compound in catalase-inhibitable luminol/hydrogen peroxide (HRP)-dependent chemiluminometric assay in Lewis lung carcinoma (LLC) cells and isolated mitochondria
• as a naphthoquinone to study its effects on the growth and differentiation of mice granulocyte and macrophage progenitor cells
• as a substrate to study the enzyme activity of human recombinant NAD(P)H dehydrogenase 1 (NQO1) protein

Biochem/physiol Actions

β-Lapachone acts as a DNA topoisomerase type I inhibitor. It exhibits anti-fungal, anti-bacterial, trypanocidal, and antiviral properties. β-Lapachone also inhibits nitric oxide (NO) and inducible NO synthase (iNOS) in alveolar macrophages.

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves