ChemicalBook > CAS DataBase List > BETA-LAPACHONE

BETA-LAPACHONE

Product Name
BETA-LAPACHONE
CAS No.
4707-32-8
Chemical Name
BETA-LAPACHONE
Synonyms
Β-LAPACHONE;β-Lapachone;b-Lapachone;CO-501;ARQ 501;SL 11001;NSC 26326;NSC 629749;--Lapachone;BETA-LAPACHONE
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
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
InChIKey
QZPQTZZNNJUOLS-UHFFFAOYSA-N
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
$195
Updated
2024/03/01
Alfa Aesar
Product number
J67308
Product name
beta-Lapachone, 98%
Packaging
5mg
Price
$152
Updated
2023/06/20
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
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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) Li?et al.?(1993),?beta-Lapachone, a Novel DNA Topoisomerase I Inhibitor With a Mode of Action Different From Camptothecin; J. Biol. Chem.,?268?22463 2) Wuerzberger?et al.?(1998),?Induction of Apoptosis in MCF-7:WS8 Breast Cancer Cells by Beta-Lapachone; Cancer Res.,?58?1876 3) Pink?et al.?(2000),?NAD(P)H:Quinone Oxidoreductase Activity Is the Principal Determinant of Beta-Lapachone Cytotoxicity. J. Biol. Chem.,?275?5416 4) Siegel?et al. (2012),?NAD(P)H:quinone Oxidoreductase 1 (NQO1) in the Sensitivity and Resistance to Antitumor Quinones; Biochem. Pharmacol.,?83?1033 5) Dong?et al.?(2010), Beta-lapachone suppresses radiation-induced activation of nuclear factor-kappaB; Exp. Mol. Med.,?42?327

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

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)
  • Β-LAPACHONE
  • 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
  • β-Lapachone (90%)
  • beta-Lapachone, Topoisomerase I inhibitor
  • 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