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PLUMBAGIN

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.

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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

481-42-5, PLUMBAGINRelated Search:


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  • 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
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  • SPECS AP-782/41885488
  • RARECHEM BW GA 0426
  • 2-methyl-5-hydroxy-1,4-naphthoquinone
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  • 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
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  • BioChemical
  • Anti-proliferative Agents
  • Inhibitors
  • Anthraquinones, Hydroquinones and Quinones
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