plumbagin

1,4-naphthalenedione, 5-hydroxy-2-methyl- (9CI)

CAS: 481-42-5 C11 H8 O3 MW: 188.18236000

Identification

Nameplumbagin
CAS Number481-42-5
EINECS207-569-6
FDA UNIIYAS4TBQ4OQ
Molecular FormulaC11 H8 O3
Molecular Weight188.18236000
MDL NumberMFCD00001682
Nikkaji NumberJ5.778I
Beilstein1870475
XlogP32.30 (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 SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 5 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for plumbagin usage levels up tonot for fragrance use.
Recommendation for plumbagin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

diospyros spp. persimmon walnut black walnut fruit walnut english walnut fruit

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].