Plumbagin

Base Information

• Chemical Name: Plumbagin
• CAS No.: 481-42-5
• Molecular Formula: C11H8O3
• Molecular Weight: 188.183
• Hs Code.: 29146990
• European Community (EC) Number: 207-569-6
• NSC Number: 688284,236613
• UNII: YAS4TBQ4OQ
• DSSTox Substance ID: DTXSID8075413
• Nikkaji Number: J5.778I
• Wikipedia: Plumbagin
• Wikidata: Q2550553
• NCI Thesaurus Code: C166377
• Pharos Ligand ID: J6ZKFU7XJ8AZ
• Metabolomics Workbench ID: 53369
• ChEMBL ID: CHEMBL295316
• Mol file: 481-42-5.mol

Synonyms:2-methyl-5-hydroxy-1,4-naphthoquinone;5-hydroxy-2-methyl-1,4-naphthoquinone;plumbagin

Chemical Property of Plumbagin

Chemical Property:

• Appearance/Colour: orange crystalline powder or crystals
• Vapor Pressure: 1.92E-06mmHg at 25°C
• Melting Point: 76-78 °C(lit.)
• Refractive Index: 1.63
• Boiling Point: 383.927 °C at 760 mmHg
• PKA: 6.70±0.20(Predicted)
• Flash Point: 200.165 °C
• PSA: 54.37000
• Density: 1.354 g/cm³
• LogP: 1.71750
• Storage Temp.: −20°C
• Solubility.: very faint turbidity in hot Methanol
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 188.047344113
• Heavy Atom Count: 14
• Complexity: 317

Purity/Quality:

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

Plumbagin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-34-36/37/38
• Safety Statements: 22-26-36/37/39-45-37/39-28A

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=O)C2=C(C1=O)C=CC=C2O
• Recent ClinicalTrials: Study of PCUR-101 in Combination With ADT in Patients With mCRPC
• Description: Plumbagin is a natural 1,4-naphthoquinone first isolated from plants of the genus Plumbago. It has diverse effects in cells and animals. Plumbagin causes the generation of reactive oxygen species and induces apoptosis in cancer cells. It activates signaling through Nrf2 and the antioxidant response element, inducing the expression of Nrf2 target genes, including NQO1 and heme oxygenase-1 in cultured neuronal cells. Plumbagin also inhibits NADPH oxidase 4 in a time- and dose-dependent manner. It can be protective against peroxide stress or deprivation of glucose or oxygen.
• Uses: antibacterial, antifungal, tuberculostatic; antifeedant (worm) Plumbagin from Plumbago indica has been used: as a reactive oxygen species agent (ROS) to induce cytotoxicity in mouse embryonic fibroblastsas an oxidative stress inducer to generate superoxide anion in Saccharomyces cerevisiaeas a reference standard in thin layer chromatography and in spectrophotometric analysis for quantification of plumbagin in Plumbago auriculate samples

Technology Process of Plumbagin

There total 69 articles about Plumbagin 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%

6-methyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl acetate (116752-29-5) → 5-hydroxy-2-methyl-1,4-naphthoquinone (481-42-5)

Guidance literature:

With hydrogenchloride; In methanol; at 50 ℃; for 1h;

DOI:10.1002/ardp.19883210312

Reference yield: 100.0%

2-bromo-5-hydroxy-[1,4]naphthoquinone (69008-03-3) + tetramethylstannane (594-27-4) → 5-hydroxy-2-methyl-1,4-naphthoquinone (481-42-5)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) bromide; In 1,4-dioxane; for 15h; Heating;

DOI:10.1021/jo00023a004

Reference yield: 97.0%

5-methoxymethoxy-2-methyl-1,4-naphthoquinone (106914-49-2) → 5-hydroxy-2-methyl-1,4-naphthoquinone (481-42-5)

Guidance literature:

With toluene-4-sulfonic acid; In neat (no solvent, solid phase); at 20 ℃; for 0.583333h; Green chemistry;

DOI:10.2174/1570178614666170321103650

upstream raw materials:

ethanol

menadione

2-methyl-1,4,5-naphthalenetriol

acetic acid

Downstream raw materials:

3-hydroxyphthalic acid

2-Methylnaphthalene

2-methyl-5-methoxy-1,4-naphthoquinone

Refernces

• 1、 Hamson,S.,Crawford,M.. "-". . p. 1162. Retrieved 1981.
• 2、 Bringmann, Gerhard,Irmer, Andreas,Büttner, Tobias,Schauml?ffel, Anu,Zhang, Guoliang,Seupel, Raina,Feineis, Doris,Fester, Karin. "Axially Chiral Dimeric Naphthalene and Naphthoquinone Metabolites, from Root Cultures of the West African Liana Triphyophyllum peltatum". . p. 2094 - 2103. Retrieved 2016.
• 3、 Zakaria, Muhamad Bin,Jeffreys, J. A. D.,Waterman, Peter G.,Zhong, Shou-Ming. "NAPHTHOQUINONES AND TRITERPENES FROM SOME ASIAN DIOSPYROS SPECIES". . p. 1481 - 1484. Retrieved 1984.
• 4、 Wurm,Gurka. "1,4-Naphthoquinones, XIII: New syntheses of plumbagin and isoplumbagin". . p. 190 - 191. Retrieved 1986.
• 5、 Wigal, Carl T.,Grunwell, John R.,Hershberger, James. "Mechanism of Conjugate Additions of Dialkylcuprates to Bromonaphthoquinones". . p. 3759 - 3761. Retrieved 1991.
• 6、 Raps, Felix C.,F?seke, Vincent C.,H?ussinger, Daniel,Sparr, Christof. "Catalyst-Controlled Transannular Polyketide Cyclization Cascades: Selective Folding of Macrocyclic Polyketides". supporting information. p. 18390 - 18394. Retrieved 2020/08/25.
• 7、 Bao, Na,Ou, Jinfeng,Shi, Wei,Li, Na,Chen, Li,Sun, Jianbo. "Highly Efficient Synthesis and Structure–Activity Relationships of a Small Library of Substituted 1,4-Naphthoquinones". . p. 2254 - 2258. Retrieved 2018/06/04.