CAS 4707-32-8 Beta-Lapachone (HCID 3885)

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Basic information

CAS: 4707-32-8
Standard SMILES: CC1(C)CCC2=C(O1)c1ccccc1C(=O)C2=O
InChIKey: QZPQTZZNNJUOLS-UHFFFAOYSA-N
Molecular formula: C15H14O3
Average molar mass: 242.27 g/mol
Monoisotopic mass: 242.09429431

Overview

Beta-lapachone is a benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities. It has a role as an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a member of orthoquinones and a benzochromenone.

Names & identifiers

Preferred name: Beta-Lapachone
IUPAC: 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
English name: BETA-LAPACHONE
Molecular formula: C15H14O3
Molecular weight: 242.27

Names & synonyms

beta-Lapachone4707-32-8lapachoneLapachone, beta-3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-B]pyran-5,6-dioneARQ 501Beta-lap-wjARQ-5013,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione6N4FA2QQ6ANSC-263262,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione

Show more names

β-Lapachoneb-LapachoneCO-501SL 11001NSC 26326NSC 629749--Lapachoneβ-Lapachone (90%)

Beta lapachoneNSC-6297492H-Naphtho[1,2-b]pyran-5,6-dione, 3,4-dihydro-2,2-dimethyl-NSC26326NSC6297492H-Naphtho(1,2-b)pyran-5,6-dione, 3,4-dihydro-2,2-dimethyl-ARQ501CHEBI:10429

Database identifiers

CAS: 4707-32-8
PubChem CID: 3885
DTXSID: DTXSID90197019
ChEMBL: CHEMBL15192
ChEBI

Properties

Computed structural properties

XLogP: 2.2
Topological polar surface area: 43.4 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 0
Heavy atoms: 18
Formal charge: 0
Complexity: 445

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Melting point: 110 °C · >110°C (dec.)
Boiling point: 381.4 · 381.4±42.0 °C(Predicted)
Density: 1.25 · 1.25±0.1 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
solubility: Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 15 mg/ml)
form: Orange to brown solid.
color: Orange
biological source: synthetic (organic)
Stability: 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.Shipping Code
Cosmetics Ingredients Functions: ANTIMICROBIALSKIN CONDITIONING - MISCELLANEOUS
InChI: 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

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
rtecs: QL6127400
hs_code: 2932990090
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 3 items

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template.

Applications · 3 items

Descriptionβ-Lapachone (4707-32-8) is a naturally occurring quinone found in the bark of the Lapacho tree (Tabebuia avellanedae). A novel DNA topoisomerase I inhibitor which unlike camptothecin does not stabilize the cleavable complex indicating a novel mode of action.1Induces apoptosis in a number of cancer cell lines.2In cancer cells over-expressing NAD(P)H:quinone oxidoreductase, reduction of β-lapachone leads to futile cycling between quinone and hydroquinone forms3resulting in the production of reactive oxygen species4. Suppresses radiation-induced activation of NFκB.5

Usesβ-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.

Usesβ-Lapachone has been used:as an anticancer compound in catalase-inhibitable luminol/hydrogen peroxide (HRP)-dependent chemiluminometricassay in Lewis lung carcinoma (LLC) cells and isolated mitochondriaas a naphthoquinone to study its effects on the growth and differentiation of mice granulocyte and macrophage progenitor cellsas a substrate to study the enzyme activity of human recombinant NAD(P)H dehydrogenase 1 (NQO1) protein