plumbagin
1,4-naphthalenedione, 5-hydroxy-2-methyl- (9CI)
Identification
| Name | plumbagin |
| CAS Number | 481-42-5 |
| EINECS | 207-569-6 |
| FDA UNII | YAS4TBQ4OQ |
| Molecular Formula | C11 H8 O3 |
| Molecular Weight | 188.18236000 |
| MDL Number | MFCD00001682 |
| Nikkaji Number | J5.778I |
| Beilstein | 1870475 |
| XlogP3 | 2.30 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 78.50 °C. @ 760.00 mm Hg |
| Boiling Point | 383.90 °C. @ 760.00 mm Hg (est) |
| Flash Point | 392.00 °F. TCC ( 200.20 °C. ) (est) |
| logP (o/w) | 2.450 (est) |
| Soluble in | water, 300 mg/L @ 15 °C (exp) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 5 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for plumbagin usage levels up to | not for fragrance use. |
| Recommendation for plumbagin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
5-
hydroxy-2-methyl-1,4-naphthalenedione
5-
hydroxy-2-methyl-1,4-naphthoquinone
5-
hydroxy-2-methylnaphthalene-1,4-dione
2-
methyl-5-hydroxy-1,4-naphthoquinone
2-
methyljuglone
1,4-
naphthalenedione, 5-hydroxy-2-methyl-
1,4-
naphthalenedione, 5-hydroxy-2-methyl- (9CI)
1,4-
naphthoquinone, 5-hydroxy-2-methyl-
plumbaein
plumbagine
plumbagone
PubMed:
Anti-tumor effects of novel 5-O-acyl plumbagins based on the inhibition of mammalian DNA replicative polymerase activity.
PubMed:
Plumbagin inhibits LPS-induced inflammation through the inactivation of the nuclear factor-kappa B and mitogen activated protein kinase signaling pathways in RAW 264.7 cells.
PubMed:
Antimicrobial activity of the carnivorous plant Dionaea muscipula against food-related pathogenic and putrefactive bacteria.
PubMed:
Antimutagenic and antioxidant properties of plumbagin and other naphthoquinones.
PubMed:
Antidiabetic effect of plumbagin isolated from Plumbago zeylanica L. root and its effect on GLUT4 translocation in streptozotocin-induced diabetic rats.
PubMed:
Inhibitory activity of plumbagin produced by Drosera intermedia on food spoilage fungi.
PubMed:
Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals.
PubMed:
Synthesis and insect antifeedant activity of plumbagin derivatives with the amino acid moiety.
PubMed:
Impact of lactic acid bacteria on oxidative DNA damage in human derived colon cells.
PubMed:
Effects of various plant polyphenols on bladder carcinogen benzidine-induced mutagenicity.
PubMed:
CorA affects tolerance of Escherichia coli and Salmonella enterica serovar Typhimurium to the lactoperoxidase enzyme system but not to other forms of oxidative stress.
PubMed:
High-performance liquid chromatography for quantification of plumbagin, an anti-Helicobacter pylori compound of Plumbago zeylanica L.
PubMed:
Investigation into the resistance of lactoperoxidase tolerant Escherichia coli mutants to different forms of oxidative stress.
PubMed:
Induction of oxidative stress by high hydrostatic pressure in Escherichia coli.
PubMed:
Unique stress response to the lactoperoxidase-thiocyanate enzyme system in Escherichia coli.
PubMed:
Selective growth-inhibiting effects of compounds identified in Tabebuia impetiginosa inner bark on human intestinal bacteria.
PubMed:
Source of tryptone in growth medium affects oxidative stress resistance in Escherichia coli.
PubMed:
Nepenthes insignis uses a C2-portion of the carbon skeleton of L-alanine acquired via its carnivorous organs, to build up the allelochemical plumbagin.
PubMed:
Regulation of aflatoxin production by naphthoquinones of walnut (Juglans regia).
PubMed:
Pro- and antioxidative properties of cortical tissue preparations from human brain exhibiting NMDA-receptor characteristics.
PubMed:
Inhibition of the mutagenicity of 2-nitrofluorene, 3-nitrofluoranthene and 1-nitropyrene by flavonoids, coumarins, quinones and other phenolic compounds.
PubMed:
Differential toxicity of juglone (5-hydroxy-1,4-naphthoquinone) and related naphthoquinones to saturniid moths.
PubMed:
[Evaluation of the sensitizing properties of plumbagin intended for use in the food industry].