alpha-Lapachone

Base Information

• Chemical Name: alpha-Lapachone
• CAS No.: 4707-33-9
• Molecular Formula: C15H14O3
• Molecular Weight: 242.274
• NSC Number: 629747,26327
• UNII: VPE3AOX9QV
• DSSTox Substance ID: DTXSID00197020
• Nikkaji Number: J16.002D
• Wikidata: Q27291952
• Metabolomics Workbench ID: 134059
• ChEMBL ID: CHEMBL441441
• Mol file: 4707-33-9.mol

Synonyms:alpha lapachone;alpha-lapachone

Chemical Property of alpha-Lapachone

Chemical Property:

• Vapor Pressure: 9.31E-06mmHg at 25°C
• Melting Point: 113-114 °C
• Refractive Index: 1.595
• Boiling Point: 372.9 °C at 760 mmHg
• Flash Point: 165.5 °C
• PSA: 43.37000
• Density: 1.25 g/cm³
• LogP: 2.90870
• XLogP3: 2.6
• 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:

99% ^*data from raw suppliers

α-Lapachone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2=C(O1)C(=O)C3=CC=CC=C3C2=O)C
• Uses: α-Lapachone is a quinone extract which displays anti-tumor activity. Effective against antimony-sensitive/resistant Leishmania parasites.

Technology Process of alpha-Lapachone

There total 35 articles about alpha-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: 99.0%

2,2-dimethyl-2H-benzo[g]chromene-5,10-dione (15297-92-4) → α-lapachone (4707-33-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 0.333333h; under 517.148 Torr;

DOI:10.1081/SCC-200043216

Reference yield: 48.0%

6-methoxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene (20213-26-7) → 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (4707-32-8) + α-lapachone (4707-33-9)

Guidance literature:

With ammonium cerium (IV) nitrate; In 1,2-dimethoxyethane; water; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.5012/bkcs.2011.32.1.153

Reference yield: 39.0%

Lapachol (84-79-7) → 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (4707-32-8) + α-lapachone (4707-33-9)

Guidance literature:

With sulfuric acid; In water; for 3h;

DOI:10.1016/S0968-0896(02)00542-4

upstream raw materials:

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

2,2-dimethyl-2H-benzo[g]chromene-5,10-dione

Lapachol

α-lapachone diacetate

Downstream raw materials:

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

4-hydroxy-α-lapachone

2,2-dimethyl-2H-benzo[g]chromene-5,10-dione

3,4-dibromodehydro-α-lapachone

Refernces

Pyranonaphthoquinone Antibiotics. Part 1. Syntheses of 9-Demethoxyeleutherins and 9-Deoxynanaomycin A Methyl Ester.

10.1039/P19810001191

The research focuses on the synthesis of 9-demethoxyeleutherins and 9-deoxynanaomycin A methyl ester, which are pyranonaphthoquinone antibiotics known for their antimicrobial properties. The study aims to develop new synthetic routes to these complex molecules, potentially leading to the total synthesis of even more complex compounds like griseusin A and granaticin. The synthesis processes involve the use of indan-1-one derivatives as precursors, employing various chemical reactions such as Lemieux-Johnson oxidation, lithium aluminium hydride reduction, and Diels-Alder reactions. Key chemicals used in the process include indanone derivatives, methanol, acetonitrile, cerium(IV) ammonium nitrate, and methoxycarbonylmethylene-triphenylphosphorane.