PLUMBAGIN

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Product Name: PLUMBAGIN
CAS No.: 481-42-5
Chemical Name: PLUMBAGIN
Synonyms: plumagin;plumbapin;PLUMBAGAN;PLUMBAGIN;Plumbaein;plumbagone;NSC 236613;NSC 688284;Plumbagine;Ophioxylin
CBNumber: CB4144779
Molecular Formula: C11H8O3
Formula Weight: 188.18
MOL File: 481-42-5.mol

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PLUMBAGIN Property

Melting point:: 76-78 °C(lit.)
Boiling point:: 283.17°C (rough estimate)
Density: 1.354
refractive index: 1.6310 (estimate)
storage temp.: -20°C
solubility: very faint turbidity in hot Methanol
form: Crystals or Crystalline Powder
pka: 6.70±0.20(Predicted)
color: Orange
Merck: 7538
Stability:: Hygroscopic
LogP: 2.450 (est)
EPA Substance Registry System: 1,4-Naphthalenedione, 5-hydroxy-2-methyl- (481-42-5)

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Safety

Hazard Codes: T
Risk Statements: 25-34-36/37/38
Safety Statements: 22-26-36/37/39-45-37/39-28A
RIDADR: UN 2923 8/PG 2
WGK Germany: 3
RTECS: QL8500000
Hazard Note: Toxic
HazardClass: 6.1(a)
PackingGroup: II
HS Code: 29146990
Toxicity: LD50 i.p. in mice: ~0.015 g/kg (Debray)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: P7262
Product name: Plumbagin from Plumbago indica
Packaging: 100mg
Price: $49.1
Updated: 2024/03/01

Sigma-Aldrich

Product number: P7262
Product name: Plumbagin from Plumbago indica
Packaging: 1g
Price: $172
Updated: 2024/03/01

TCI Chemical

Product number: P1139
Product name: Plumbagin
Purity: >98.0%(HPLC)(T)
Packaging: 1g
Price: $111
Updated: 2024/03/01

Cayman Chemical

Product number: 14314
Product name: Plumbagin
Purity: ≥98%
Packaging: 100mg
Price: $36
Updated: 2024/03/01

Cayman Chemical

Product number: 14314
Product name: Plumbagin
Purity: ≥98%
Packaging: 250mg
Price: $54
Updated: 2024/03/01

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PLUMBAGIN Chemical Properties,Usage,Production

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.

Chemical Properties

ORANGE CRYSTALLINE POWDER OR CRYSTALS

Uses

antibacterial, antifungal, tuberculostatic; antifeedant (worm)

Uses

Plumbagin from Plumbago indica has been used:

as a reactive oxygen species agent (ROS) to induce cytotoxicity in mouse embryonic fibroblasts
as an oxidative stress inducer to generate superoxide anion in Saccharomyces cerevisiae
as a reference standard in thin layer chromatography and in spectrophotometric analysis for quantification of plumbagin in Plumbago auriculate samples

Definition

ChEBI: A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.

General Description

Plumbagin is a bioactive naphthoquinone present majorly in Plumbago indica L. It is a quinoid and is also derived from the roots of Plumbago zeylanica?roots.

Biochem/physiol Actions

Plumbagin exhibits various pharmacological activities including antimicrobial, anticancer, anti-atherosclerotic, antidiabetic, anti-inflammatory, hypolipidemic, and neuroprotective activities. It inhibits the signal transducer and activator of transcription 3 (STAT3) signaling and halts the proliferation of esophageal squamous cell carcinoma (ESCC). Plumbagin elicits protective antioxidative functionality in 4-nitroquinoline-N-oxide (NQNO) induced stress in lymphoma. Plumbagin in a nanoemulsion formulation has antiproliferative effect towards prostate cancer.

in vitro

plumbagin exhibited effective cell growth inhibition via inducing cancer cells to undergo g2/m phase arrest and apoptosis. blockade of cell cycle was associated with increased levels of p21 and reduced amounts of cdc2, cdc25c and cyclinb1. plumbagin treatment also found to enhance the levels of inactivated phosphorylated cdc2 and cdc25c. blockade of p53 activity partially decreased plumbagin-induced apoptosis and g2/m arrest, indicating it might be operated by p53-dependent and independent pathway [1].

in vivo

to determine whether plumbagin inhibited the in vivo tumor growth, a549 cells were injected into nude mice. tumor growth inhibition was most evident in mice treated with plumbagin at 2 mg/kg/day, where around 80% reductions in tumor size were observed, in contrast with mice treated with the vehicle. no sign of toxicity was observed in plumbagin-treated mice as judged by monitoring body weight [1].

IC 50

11.69 μm for a549 cells

Purification Methods

It crystallises in yellow needles from aqueous EtOH. It is soluble in organic solvents, it is steam volatile and it sublimes on heating in a vacuum. [Fieser & Dunn J Am Chem Soc 58 572 1936, Beilstein 8 III 2576, 8 IV 2376.]

References

[1] hsu yl,cho cy,kuo pl,huang yt,lin cc. plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) induces apoptosis and cell cycle arrest in a549 cells through p53 accumulation via c-jun nh2-terminal kinase-mediated phosphorylation at serine 15 in vitro and in vivo. j pharmacol exp ther.2006 aug;318(2):484-94.

PLUMBAGIN Preparation Products And Raw materials

Raw materials

1,4-Diamino-2,3-dihydroanthraquinone N-Bromosuccinimide Tin tetrachloride 1,5-Dihydroxy naphthalene Acetyl chloride Tetrakis(triphenylphosphine)palladium 1,4-Dioxane Aluminum chloride 1,4-Diamino anthraquinone Sulfuryl chloride Ethyl acetate Cuprous bromide Sodium bicarbonate Dichloromethane Acetic acid Nitrobenzene Magnesium sulfate Magnesium Iodomethane

Preparation Products

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View Lastest Price from PLUMBAGIN manufacturers

R&D Scientific Inc.

Product: Plumbagin 481-42-5
Price: US $1800.00/g
Min. Order: 1g
Purity: 97
Supply Ability: 500 Kg
Release date: 2024-03-31

Shanghai Standard Technology Co., Ltd.

Product: Plumbagin 481-42-5
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥98%(HPLC)
Supply Ability: 10 g
Release date: 2020-01-20

Honest Joy Holdings Limited

Product: Plumbagin 481-42-5
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99.0%
Supply Ability: 100 tons
Release date: 2022-02-18

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plumbagone

1,4-Dihydro-1,4-dioxo-5-hydroxy-2-methylnaphthalene

Plumbagin (natural)

PLUMBAGIN PRACTICAL GRADE

Plumbagin, 99+%

PLUMBAGIN(RG)

1,4-NAPHTHALENEDIONE,5-HYDROXY-2-METHYL

PLANT STEROLS KIT

plumbapin

Plumbagin from Plumbago indica

Plumbagin,95%

Plumbagin ,97%

NSC 236613

NSC 688284

Plumbagine

5-hydroxy-2-methyl-4-naphthalenedione

5-hydroxy-2-methyl-4-naphthoquinone

2-Methyl-5-hydroxy-1,4-naphthalenedione

5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione

1,4-Dihydro-1,4-dioxo-5-hydroxy-2-methylnaphthalene, 5-Hydroxy-2-methyl-1,4-naphthoquinone

5-Hydroxy-2-methylnaphthalene-1,4-dione

1,4-Dihydro-1,4-dioxo-5-hydroxy-2-methylnaphthalene, 5-Hydroxy-2-methyl-1,4-naphthoquinone, Plumbagin

Ophioxylin

PLUMBAGIN FROM FROM PLUMBAGO INDICA

5-HYDROXY-2-METHYL-1,4-NAPHTHOQUINONE

5-HYDROXY-2-METHYL-1,4-NAPTHOQUINONE

PLUMBAGAN

PLUMBAGIN

SPECS AP-782/41885488

RARECHEM BW GA 0426

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

2-methyljuglone

5-hydroxy-2-methyl-1,4-naphthalenedione

Plumbagin&gt

Plumbaein

5-Hydroxy-2-methyl-1,4-naphthochinon

Plumbagin (2-Methyljuglone)

5-Hydroxy-2-methylnaphthalene-1,4-dione(Plumbagin)

plumagin

481-42-5

C11H8O3

Cancer Research

Chemopreventive Agents

BioChemical

Anti-proliferative Agents

Inhibitors

Anthraquinones, Hydroquinones and Quinones

chem-chemical