Deoxylapachol

Base Information

• Chemical Name: Deoxylapachol
• CAS No.: 3568-90-9
• Molecular Formula: C15H14O2
• Molecular Weight: 226.275
• Hs Code.: 2914690090
• NSC Number: 123507
• UNII: M5RT9GV702
• DSSTox Substance ID: DTXSID40189186
• Nikkaji Number: J156.701B
• Wikidata: Q27106375
• Metabolomics Workbench ID: 68041
• ChEMBL ID: CHEMBL32570
• Mol file: 3568-90-9.mol

Synonyms:deoxylapachol

Chemical Property of Deoxylapachol

Chemical Property:

• Vapor Pressure: 2.42E-05mmHg at 25°C
• Refractive Index: 1.57
• Boiling Point: 359.2 °C at 760 mmHg
• Flash Point: 134.8 °C
• PSA: 34.14000
• Density: 1.125 g/cm³
• LogP: 3.34830
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 226.099379685
• Heavy Atom Count: 17
• Complexity: 397

Purity/Quality:

99%, ^*data from raw suppliers

Deoxylapachol 99.07% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=CC(=O)C2=CC=CC=C2C1=O)C
• Description: Deoxylapachol is the main allergen identified in teak (Tectona grandis). Sensitization often concerns people in woodwork.

Technology Process of Deoxylapachol

There total 19 articles about Deoxylapachol 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: 98.0%

(1R*,4S*,4aR*,9aS*)-1,4,4a,9-tetrahydro-4a-prenyl-1,4-methanoanthracene-9,10-dione + (1R*,4S*,4aS*,9aR*)-1,4,4a,9-tetrahydro-4a-prenyl-1,4-methanoanthracene-9,10-dione → deoxylapachol (3568-90-9)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; for 2h; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201403064

Reference yield: 98.0%

→ deoxylapachol (3568-90-9)

Guidance literature:

Reference yield: 96.0%

(3-methyl-2-butenyl)trifluorosilane (114067-34-4) + [1,4]naphthoquinone (130-15-4) → deoxylapachol (3568-90-9)

Guidance literature:

With iron(III) chloride; In formamide; for 24h; Ambient temperature;

DOI:10.1016/0040-4039(95)00394-R

upstream raw materials:

1,4-Dihydroxynaphthalene

2-methyl-3-buten-2-ol

4-methyl-pent-3-enoic acid

[1,4]naphthoquinone

Downstream raw materials:

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

2-(3-methyl-but-2-enyl)-2,3-epoxy-1,4-naphthoquinone

lapachenole

mollugin

Refernces

• 1、 Katoh, Tadashi,Katoh, Takeru,Monma, Hiromitsu,Wakasugi, Jun,Narita, Koichi. "Synthesis of β-lapachone, a potential anticancer agent from the lapacho tree". . p. 7099 - 7103. Retrieved 2014.
• 2、 Sunassee, Suthananda N.,Van Wyk, Albert W.W.,Osoniyi, Omolaja,Hendricks, Denver T.,Davies-Coleman, Michael T.. "Synthesis and cytotoxicity of analogues of the marine secondary metabolite, 2-deoxylapachol". . p. 677 - 679. Retrieved 2008/09/20.