ChemicalBook > CAS DataBase List > BETA-LAPACHONE

BETA-LAPACHONE

Product Name: BETA-LAPACHONE
CAS No.: 4707-32-8
Chemical Name: BETA-LAPACHONE
Synonyms: β-Lapachone;b-Lapachone;CO-501;ARQ 501;SL 11001;NSC 26326;NSC 629749;--Lapachone;BETA-LAPACHONE;β-Lapachone (90%)
CBNumber: CB1771280
Molecular Formula: C15H14O3
Formula Weight: 242.27
MOL File: 4707-32-8.mol

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BETA-LAPACHONE Property

Melting point:: >110°C (dec.)
Boiling point:: 381.4±42.0 °C(Predicted)
Density: 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:: 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
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
InChIKey: QZPQTZZNNJUOLS-UHFFFAOYSA-N
SMILES: C12C3=C(C=CC=C3)C(=O)C(=O)C=1CCC(C)(C)O2
LogP: 2.820 (est)

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Safety

WGK Germany: 3
RTECS: QL6127400
HS Code: 2932990090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: L2037
Product name: β-Lapachone
Purity: ≥98% (TLC)
Packaging: 5mg
Price: $200
Updated: 2025/07/31

Cayman Chemical

Product number: 15021
Product name: β-Lapachone
Purity: ≥98%
Packaging: 5mg
Price: $72
Updated: 2024/03/01

Cayman Chemical

Product number: 15021
Product name: β-Lapachone
Purity: ≥98%
Packaging: 10mg
Price: $110
Updated: 2024/03/01

Cayman Chemical

Product number: 15021
Product name: β-Lapachone
Purity: ≥98%
Packaging: 25mg
Price: $263
Updated: 2024/03/01

Cayman Chemical

Product number: 15021
Product name: β-Lapachone
Purity: ≥98%
Packaging: 50mg
Price: $424
Updated: 2024/03/01

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BETA-LAPACHONE Chemical Properties,Usage,Production

Description

β-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.1?Induces apoptosis in a number of cancer cell lines.2?In cancer cells over-expressing NAD(P)H:quinone oxidoreductase, reduction of β-lapachone leads to futile cycling between quinone and hydroquinone forms3?resulting in the production of reactive oxygen species4. Suppresses radiation-induced activation of NFκB.5

Chemical Properties

Orange Solid

Uses

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

Uses

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.

Definition

ChEBI: 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 activi ies.

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.

References

[1] C J LI A B P L Averboukh. beta-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin.[J]. The Journal of Biological Chemistry, 1993, 268 30: 22463-22468.
[2] S M WUERZBERGER. Induction of apoptosis in MCF-7:WS8 breast cancer cells by beta-lapachone.[J]. Cancer research, 1998, 58 9: 1876-1885.
[3] J J PINK. NAD(P)H:Quinone oxidoreductase activity is the principal determinant of beta-lapachone cytotoxicity.[J]. The Journal of Biological Chemistry, 2000, 275 8: 5416-5424. DOI:10.1074/jbc.275.8.5416
[4] DAVID SIEGEL David R Chao Yan. NAD(P)H:quinone oxidoreductase 1 (NQO1) in the sensitivity and resistance to antitumor quinones[J]. Biochemical pharmacology, 2012, 83 8: Pages 1033-1040. DOI:10.1016/j.bcp.2011.12.017
[5] Beta-lapachone suppresses radiation-induced activation of nuclear factor-kappaB

BETA-LAPACHONE Preparation Products And Raw materials

Raw materials

Preparation Products

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BETA-LAPACHONE Suppliers

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View Lastest Price from BETA-LAPACHONE manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: BETA-LAPACHONE 4707-32-8
Price: US $140.00-110.00/G
Min. Order: 10G
Purity: 98%MIN
Supply Ability: 25KG
Release date: 2025-09-22

Henan Aochuang Chemical Co.,Ltd.

Product: BETA-LAPACHONE 4707-32-8
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1ton
Release date: 2022-09-28

Career Henan Chemical Co

Product: BETA-LAPACHONE 4707-32-8
Price: US $1.00/KG
Min. Order: 1G
Purity: 98%
Supply Ability: 100KG
Release date: 2018-08-16

4707-32-8, BETA-LAPACHONERelated Search:

RAF709 TAK 599 Panobinostat Belinostat (PXD101) SRT1720 BI 2536 CRA-02478 GDC-0879 17-AAG 1,5-DIMETHYLNAPHTHALENE ICRF 193 1,2-NAPHTHOQUINONE 2,3 OCTANEDIONE 2,3-HEPTANEDIONE BETA-LAPACHONE 4-METHOXY-1,2-DIHYDRO-NAPHTHALENE BETA-LAPACHONE, P-METHYLPHENYLIMINO- 3-allyl-beta-lapachone

BETA-LAPACHONE

2-b)pyran-5,6-dione,3,4-dihydro-2,2-dimethyl-2h-naphtho(

b-Lapachone

B-LAPACHONE,2,2-DIMETHYL-3,4-DIHYDRO-2H-BENZO[H]CHROMENE-5,6-DIONE

3,4-DIHYDRO-2,2-DIMETHYL-2H-NAPHTHO[1,2-B]PYRAN-5,6-DIONE

3,4-DIHYDRO-2,2-DIMETHYL-2H-NAPHTHOL[1,2-B]PYRAN-5,6-DIONE

2,2-Dimethyl-3,4,5,6-tetrahydro-2H-naphtho[1,2-b]pyran-5,6-dione

2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione

CO-501

β-Lapachone (90%)

2,2-DiMethyl-3,4-dihydro-2H-benzo[h]chroMene-5,6-dione

ARQ-501 (beta lapachone)

2H-Naphtho[1,2-b]pyran-5,6-dione, 3,4-dihydro-2,2-dimethyl-

2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-quinone

ARQ 501

NSC 26326

NSC 629749

SL 11001

β-Lapachone (ARQ-501)

ARQ-501; NSC-26326; NSC-629749; SL-11001; BETA-LAPACHONE; Β-LAPACHONE; ARQ-501

beta-Lapachone (ARQ-501, CO-501)

BETA-LAPACHONE USP/EP/BP

Beta-Lapachone (ARQ-501)

--Lapachone

β-Lapachone

ARQ 501,ARQ501,Topoisomerase,Inhibitor,NSC26326,β-Lapachone,Apoptosis,NSC 26326,Autophagy,β Lapachone,inhibit,βLapachone

beta-Lapachone, Topoisomerase I inhibitor

β-Lapachone, 10 mM in DMSO

4707-32-8

Cell Signaling and Neuroscience

Cell Biology

Apoptosis and Cell Cycle

BioChemical

DNA Repair Regulators

DNA metabolism

Inhibitors

Aromatics

Heterocycles

Isotope Labelled Compounds

DNA Repair RegulatorsCancer Research

Gene RegulationEnzyme Inhibitors by Enzyme

Topoisomerase I

Apoptosis and Cell Cycle

Chemopreventive Agents

DNA metabolism

R to