22333-58-0

Basic information

• Product Name: 9-Hydroxy-alpha-lapachone
• Synonyms: 9-Hydroxy-alpha-lapachone;9-Hydroxy-α-lapachone;9-Hydroxy-2,2-diMethyl-3,4-dihydro-2H-benzo[g]chroMene-5,10-dione
• CAS NO: 22333-58-0
• Molecular Formula: C15H14O4
• Molecular Weight: 258.26926
• Mol File: 22333-58-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 9-Hydroxy-alpha-lapachone(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Hydroxy-alpha-lapachone(22333-58-0)
• EPA Substance Registry System: 9-Hydroxy-alpha-lapachone(22333-58-0)

Safety Data

• Hazardous Substances Data: 22333-58-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9-Hydroxy-alpha-lapachone is used as an anti-cancer agent for its ability to inhibit the growth of various types of cancer cells, including breast, prostate, and colon cancer. It modulates multiple oncological signaling pathways, exerting inhibitory effects on tumor growth and progression.
Used in Antioxidant Applications:
9-Hydroxy-alpha-lapachone is used as an antioxidant, providing protection against oxidative stress and damage, which can contribute to the prevention and treatment of various medical conditions.
Used in Anti-inflammatory Applications:
9-Hydroxy-alpha-lapachone is used as an anti-inflammatory agent, helping to reduce inflammation and alleviate symptoms associated with various inflammatory diseases.
Overall, 9-Hydroxy-alpha-lapachone shows promise as a potential drug candidate for the treatment of cancer and other diseases, with its multifaceted properties offering potential therapeutic benefits in various medical applications.

Upstream product

• 22333-57-9 9-hydroxy-2,2-dimethyl-2H-benzo[g]chromene-5,10-dione 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 18855-92-0 3-chlorojuglone 
• 68963-21-3 8-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione 
• 83-56-7 1,5-dihydroxynaphthalene 
• 50-00-0 formaldehyd 
• 4923-58-4 3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone 
• 115-11-7 isobutene 
• 41067-05-4 2-(dimethylamino)-8-hydroxy-1,4-naphthalenedione 
• 104556-22-1 8-hydroxy-3-(3-methylbut-2-enyl)-1,4-naphthoquinone 
• 104556-23-2 2,3-epoxy-2,3-dihydro-5-hydroxy-2-(3'-methyl-2'-butenyl)-1,4-naphthoquinone 

Downstream Products

• 35241-80-6 9-methoxy-α-lapachone 

Relevant articles and documents

Synthesis of dehydro-α-lapachones, α- and β-lapachones, and screening against cancer cell lines

14 new naphthoquinones were prepared and tested against human cancer cell lines PC-3 (prostate), HCT-116 (colon carcinoma), SNB-19 (glioblastoma), HL-60 (leukemia) and MCF-7 (breast), and a nontumor cell line L929 (murine fibroblasts) to determine cytotoxicity with the MTT assay. 8-OH-β-lapachones (14a, 14c, 14d) presented best results, showing low IC50 values and high selectivity for HCT-116 and HL-60 tumor cells.

β-Lapachone analogs with enhanced antiproliferative activity

In this study, we describe the synthesis of a series of α- and β-lapachone containing hydroxyl or methoxyl groups on the benzene ring, by means of the selective acid promoted cyclization of the appropriate lapachol analog. The evaluation of the antiproliferative activity in human solid tumor cell lines provided 7-hydroxy-β-lapachone as lead with enhanced activity over the parent drug β-lapachone. Cell cycle studies, protein expression experiments, and reactive oxygen species analysis revealed that, similarly to β-lapachone, ROS formation and DNA damage are critical factors in the cellular toxicity of 7-hydroxy-β-lapachone.

SYNTHESIS OF SOME NATURALLY OCCURING PRENYLATED JUGLONE DERIVATIVES

Synthesis of α-caryopterone (I), α-dihydrocaryopterone (II), 9-methoxy-α-lapachone (III) and 4,9-dihydroxy-α-lapachone (IV) has been carried out starting from juglone via 2,8-dihydroxy-1,4-naphtoquinone.

Effect of 9-hydroxy-α-and 7-hydroxy-β-pyran naphthoquinones on trypanosoma cruzi and structure-Activity relationship studies

The available treatment for the prevention and cure of Chagas disease, caused by the protozoan Trypanosoma cruzi, is still unsatisfactory. Thus, there is an urgent need to develop new drugs. In the last few years, our research group has focused on finding

Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines

A synthetic method to obtain α- and β-pyran naphthoquinones 10 and 11 with a hydroxyl substituent on the aromatic ring was developed. Two series of α- and β-pyran naphthoquinones were obtained from the 8-hydroxy-lawsone, and their anticancer properties we

Two New Syntheses of the Pyranojuglone Pigment α-Caryopterone

By a simple process, 3-methoxyjuglone ( = 8-hydroxy-2-methoxy-1,4-naphthoquinone; 9) has been synthesized from 1,2,4-trimethoxybenzene (5) and converted, after prenylation, to α-caryopterone (1; Scheme 1), a pyranojuglone pigment from Caryopteris clandonensis.On the other hand, juglone ( = 5-hydroxy-1,4-naphthoquinone; 12) was regioselectively prenylated at C(2) via its 1-methoxy-cyclohexa-1,3-diene adduct 15 (Scheme 2).The 2-prenyljuglone (4) thus formed led to 1 after oxidation and other reactions.

SYNTHESIS OF NATURALLY OCCURING PRENYLATED JUGLONE DERIVATIVES

Condensation of 2,8-dihydroxy-1,4-naphthoquinone (7) with isovaleraldehyde gave 2,8-dihydroxy-3-(3-methylbut-1-enyl)-1,4-naphthoquinone (8).Compound 8 on oxidative cyclodehydrogenation with DDQ yielded 8-hydroxy-2-isopropylnaphtho--furan-4,9-dione (9), 9-hydroxy-dehydro-α-lapachone (1) and 6-hydroxy-2-isopropylnaphtho furan-4,5-dione (10).Compound 1 on catalytic hydrogenation afforded 2, and methylation of the latter gave 3.The allylic bromination of 2 followed by hydrolysis furnished 4,9-dihydroxy-α-lapachone (4).Compounds 1, 2, 3 and 4 are naturally occuring substances.