9-Hydroxy-alpha-lapachone

Base Information

• Chemical Name: 9-Hydroxy-alpha-lapachone
• CAS No.: 22333-58-0
• Molecular Formula: C15H14O4
• Molecular Weight: 258.27
• Hs Code.: 2914400090
• DSSTox Substance ID: DTXSID70415768
• Nikkaji Number: J2.225.866D
• Wikidata: Q72484669
• Metabolomics Workbench ID: 126357
• ChEMBL ID: CHEMBL2036874
• Mol file: 22333-58-0.mol

Synonyms:9-hydroxy-alpha-lapachone;22333-58-0;9-hydroxy-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione;alpha-Dihydrocaryopterone;9-Hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione;-Dihydrocaryopterone;3,4-Dihydro-9-hydroxy-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione;9-Hydroxy-alpha-lapachone;9-Hydroxy--lapachone;CHEMBL2036874;DTXSID70415768;AKOS015999032;B0005-189981;3,4-dihydro-9-hydroxy-2,2-dimethyl-2H-benzo[g]chromene-5,10-dione

Chemical Property of 9-Hydroxy-alpha-lapachone

Chemical Property:

• PSA: 63.60000
• LogP: 2.61430
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 258.08920892
• Heavy Atom Count: 19
• Complexity: 475

Purity/Quality:

98%min ^*data from raw suppliers

9-Hydroxy-alpha-Lapachone 95+% ^*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=C(C2=O)C=CC=C3O)C

Technology Process of 9-Hydroxy-alpha-lapachone

There total 16 articles about 9-Hydroxy-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: 100.0%

9-hydroxy-2,2-dimethyl-2H-benzo[g]chromene-5,10-dione (22333-57-9) → 9-hydroxy-α-lapachone (22333-58-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 50 ℃; for 2h; under 1396.34 Torr;

DOI:10.1007/s00044-019-02439-w

Reference yield: 63.0%

2,3-epoxy-2,3-dihydro-5-hydroxy-2-(3'-methyl-2'-butenyl)-1,4-naphthoquinone (104556-23-2) → 9-hydroxy-α-lapachone (22333-58-0)

Guidance literature:

With boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene;

DOI:10.1002/hlca.19850680827

Reference yield: 46.0%

3,5-dihydroxy-2-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione → 7-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (22333-59-1) + 9-hydroxy-α-lapachone (22333-58-0)

Guidance literature:

With methanesulfonic acid; In dichloromethane; at -45 ℃; for 0.05h;

DOI:10.1016/j.ejmech.2012.04.008

upstream raw materials:

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

2,3-epoxy-2,3-dihydro-5-hydroxy-2-(3'-methyl-2'-butenyl)-1,4-naphthoquinone

8-hydroxy-3-(3-methylbut-2-enyl)-1,4-naphthoquinone

3,3-dimethyl acrylaldehyde

Downstream raw materials:

9-methoxy-α-lapachone

Refernces

• 1、 Rios-Luci, Carla,Bonifazi, Evelyn L.,Leon, Leticia G.,Montero, Juan C.,Burton, Gerardo,Pandiella, Atanasio,Misico, Rosana I.,Padron, Jose M.. "β-Lapachone analogs with enhanced antiproliferative activity". . p. 264 - 274. Retrieved 2012.
• 2、 Kapoor, N. K.,Gupta, R. B.,Khanna, R. N.. "SYNTHESIS OF SOME NATURALLY OCCURING PRENYLATED JUGLONE DERIVATIVES". . p. 5083 - 5084. Retrieved 1980.
• 3、 Da Rocha, David R.,De Souza, Ana C. G.,Resende, Jackson A. L. C.,Santos, Wilson C.,Dos Santos, Evelyne A.,Pessoa, Claudia,De Moraes, Manoel O.,Costa-Lotufo, Leticia V.,Montenegro, Raquel C.,Ferreira, Vitor F.. "Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines". experimental part. p. 4315 - 4322. Retrieved 2011/07/08.