beta-Lapachone

Base Information

• Chemical Name: beta-Lapachone
• CAS No.: 4707-32-8
• Molecular Formula: C15H14O3
• Molecular Weight: 242.274
• Hs Code.: 2914399090
• NSC Number: 629749,26326
• UNII: 6N4FA2QQ6A
• DSSTox Substance ID: DTXSID90197019
• Nikkaji Number: J16.003B
• Wikidata: Q27089386
• NCI Thesaurus Code: C28694
• Pharos Ligand ID: JPM2GNZD6BZB
• Metabolomics Workbench ID: 50031
• ChEMBL ID: CHEMBL15192
• Mol file: 4707-32-8.mol

Synonyms:3,4-dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione;ARQ 501;ARQ-501;beta-lap-wj;beta-lapachone;lapachone;MB-12066;MB12066

Chemical Property of beta-Lapachone

Chemical Property:

• Vapor Pressure: 5.09E-06mmHg at 25°C
• Melting Point: >110oC (dec.)
• Boiling Point: 381.4°C at 760 mmHg
• Flash Point: 169.7°C
• PSA: 43.37000
• Density: 1.25g/cm³
• LogP: 2.75210
• Storage Temp.: -20?C Freezer
• Solubility.: Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 15 mg/ml)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 445

Purity/Quality:

98%,99%, ^*data from raw suppliers

β-Lapachone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O)C
• Recent ClinicalTrials: Safety, Tolerability and Pharmacokinetic Study of MB12066 in Healthy Volunteers
• Recent EU Clinical Trials: A Phase 2 Study of ARQ 501 in Patients with Locally Advanced, Recurrent or Metastatic Squamous Cell Carcinoma of the Head and Neck
• 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
• 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 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 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.

Technology Process of beta-Lapachone

There total 87 articles about beta-Lapachone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Lapachol (84-79-7) → 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (4707-32-8)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃;

DOI:10.1039/c6ra14701a

Reference yield: 90.0%

Lapachol (84-79-7) → 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (4707-32-8) + α-lapachone

Guidance literature:

With zinc(II) chloride; In dichloromethane; at 42 ℃; for 4h; Reagent/catalyst; Temperature;

DOI:10.1016/j.bmc.2016.12.043

Reference yield: 90.0%

2-(3-methyl-but-2-enyl)-2,3-epoxy-1,4-naphthoquinone (137492-06-9) → 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (4707-32-8)

Guidance literature:

With sulfuric acid; In acetic acid; at 20 ℃; for 0.333333h;

DOI:10.1039/c004580b

upstream raw materials:

α-lapachone

Lapachol

2-hydroxy-3-(3-methyl-3-sulfooxy-butyl)-[1,4]naphthoquinone

5,6-diacetoxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene

Downstream raw materials:

5,6-diacetoxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene

7,8-dihydro-9,9-dimethyl-9H-pyrano[3',2':4]naphtha[1,2-b]quinoxaline

3,4-dihydro-2,2-dimethyl-2H-naphtho[1,2-b]-pyran

α-lapachone

Refernces

• 1、 Chen, Wenliang,Tang, Weidong,Zhang, Rujun,Lou, Liguang,Zhao, Weimin. "Cytotoxic germacrane-type sesquiterpenes, pimarane-type diterpenes, and a naphthalene derivative from Wollastonia biflora". . p. 567 - 570. Retrieved 2007.
• 2、 De Moura, Kelly C.G.,Salomao, Kelly,Menna-Barreto, Rubem F.S.,Emery, Flavio S.,Pinto, Maria Do Carmo F.R.,Pinto, Antonio V.,De Castro, Solange L.. "Studies on the trypanocidal activity of semi-synthetic pyran[b-4,3] naphtho[1,2-d]imidazoles from β-lapachone". . p. 639 - 645. Retrieved 2004.
• 3、 Zhou, Yinjian,Dong, Ying,Huang, Gang,Wang, Yiguang,Huang, Xiaonan,Zhang, Fayun,Boothman, David A.,Gao, Jinming,Liang, Wei. "Lysosome-oriented, dual-stage pH-responsive polymeric micelles for β-lapachone delivery". . p. 7429 - 7440. Retrieved 2016.
• 4、 Gontijo, Talita B.,De Freitas, Rossimiriam P.,De Lima, Guilherme F.,De Rezende, Lucas C. D.,Pedrosa, Leandro F.,Silva, Thaissa L.,Goulart, Marilia O.F.,Cavalcanti, Bruno C.,Pessoa, Claudia,Bruno, Marina P.,Corrêa, José R.,Emery, Flavio S.,Da Silva Júnior, Eufranio N.. "Novel fluorescent lapachone-based BODIPY: Synthesis, computational and electrochemical aspects, and subcellular localisation of a potent antitumour hybrid quinone". . p. 13281 - 13284. Retrieved 2016.
• 5、 Ferreira, Sabrina Baptista,Kaiser, Carlos Roland,Ferreira, Vitor Francisco. "An improved one-pot procedure for the preparation of β-lapachone and nor-β-lapachone, two potent drug prototypes". . p. 211 - 215. Retrieved 2009.
• 6、 Fieser et al.. "". . p. 85,86, 95. Retrieved 1948.
• 7、 Dias, Gleiston G.,Pinho, Pamella V. B.,Duarte, Hélio A.,Resende, Jarbas M.,Rosa, Andressa B. B.,Correa, José R.,Neto, Brenno A. D.,Da Silva Júnior, Eufranio N.. "Fluorescent oxazoles from quinones for bioimaging applications". . p. 76053 - 76063. Retrieved 2016.
• 8、 Bomba?a, Ana Cristina S.,Silva, Leonardo A.,Chaves, Otávio Augusto,da Silva, Lorrainy S.,Barbosa, Juliana M.C.,da Silva, Ari M.,Ferreira, Aurélio B.B.,Menna-Barreto, Rubem F.S.. "Novel N,N-di-alkylnaphthoimidazolium derivative of β-lapachone impaired Trypanosoma cruzi mitochondrial electron transport system". . . Retrieved 2021.
• 9、 Halicki, Priscila Cristina Bartolomeu,da Silva, Eufranio Nunes,Jardim, Guilherme Augusto de Melo,Almeida, Renata Gomes de,Vicenti, Juliano Rosa de Menezes,Gon?alves, Bruna Lisboa,da Silva, Pedro Eduardo Almeida,Ramos, Daniela Fernandes. "Benzo[a]phenazine derivatives: Promising scaffolds to combat resistant Mycobacterium tuberculosis". . p. 352 - 362. Retrieved 2021/06/30.