Lapachol

Base Information

• Chemical Name: Lapachol
• CAS No.: 84-79-7
• Molecular Formula: C15H14 O3
• Molecular Weight: 242.274
• Hs Code.: 2914690090
• European Community (EC) Number: 201-563-7
• NSC Number: 629756,11905
• UNII: B221938VB6
• DSSTox Substance ID: DTXSID6049430
• Nikkaji Number: J1.467.697J,J4.900J
• Wikipedia: Lapachol
• Wikidata: Q739601
• Pharos Ligand ID: N4BDTH4WRYL3
• Metabolomics Workbench ID: 67464
• ChEMBL ID: CHEMBL15193
• Mol file: 84-79-7.mol

Synonyms:2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphtho-quinone;lapachol;lapachol, sodium salt;NSC-11905

Chemical Property of Lapachol

Chemical Property:

• Appearance/Colour: white to yellow powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 141-143 ºC(lit.)
• Refractive Index: 1.5740 (estimate)
• Boiling Point: 398.6 ºC at 760 mmHg
• PKA: 4.81±0.10(Predicted)
• Flash Point: 209 ºC
• PSA: 54.37000
• Density: 1.235 g/cm³
• LogP: 3.23400
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: ethanol: soluble10mg/mL, clear, light yellow to yellow
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 439

Purity/Quality:

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

Lapachol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCC1=C(C2=CC=CC=C2C(=O)C1=O)O)C
• Description: Lapachol, a benzoquinone, is a secondary allergen in teak (Tectona grandis).
• Uses: antineoplastic, antifungal It was used in the synthesis of the lapachol metal complexes. Lapachol was used in the synthesis of the lapachol metal complexes.

Technology Process of Lapachol

There total 47 articles about Lapachol 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: 78.0%

isonaphthazarine (605-37-8) + isoprene (78-79-5,9003-31-0) → Lapachol (84-79-7)

Guidance literature:

With oxalic acid; In 1,4-dioxane; at 100 ℃; for 6h;

DOI:10.1016/j.bmc.2016.12.043

Reference yield: 78.0%

2-hydroxynaphtho-1,4-quinone (83-72-7) + 3,3-dimethyl acrylaldehyde (107-86-8) → Lapachol (84-79-7)

Guidance literature:

With formic acid; In ethanol; water; at 200 ℃; for 3h; under 155.149 - 155149 Torr; chemoselective reaction;

DOI:10.1055/s-0030-1260771

Reference yield: 61.0%

2-hydroxynaphtho-1,4-quinone (83-72-7) + prenyl bromide (870-63-3) → Lapachol (84-79-7) + 2-(1,1-dimethylprop-2-enyl)-3-hydroxy-naphthalene-1.4-dione (64469-16-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In 1,4-dioxane; at 20 ℃; for 4h;

DOI:10.1002/cmdc.201500189

upstream raw materials:

2-hydroxy-1,4-naphthoquinone silver salt

prenyl bromide

1,2,3,4-tetrahydroxynaphthalene

3-methyl-2-buten-1-ol

Downstream raw materials:

2-methoxylapachol

2-(tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(3-methylbut-2-enyl)-1,4-naphthoquinone

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

3,4-dehydro-β-lapachone

Refernces

• 1、 Gates,Moesta. "-". . p. 614. Retrieved 1948.
• 2、 Geisler, Heiko,Westermayr, Julia,Cseh, Klaudia,Wenisch, Dominik,Fuchs, Valentin,Harringer, Sophia,Plutzar, Sarah,Gajic, Natalie,Hejl, Michaela,Jakupec, Michael A.,Marquetand, Philipp,Kandioller, Wolfgang. "Tridentate 3-Substituted Naphthoquinone Ruthenium Arene Complexes: Synthesis, Characterization, Aqueous Behavior, and Theoretical and Biological Studies". . p. 9805 - 9819. Retrieved 2021/06/30.
• 3、 Calil, Felipe A.,David, Juliana S.,Chiappetta, Estela R.C.,Fumagalli, Fernando,Mello, Rodrigo B.,Leite, Franco H.A.,Castilho, Marcelo S.,Emery, Flavio S.,Nonato, M.Cristina. "Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase". . p. 357 - 366. Retrieved 2019/02/19.