plumbagin
1,4-naphthalenedione, 5-hydroxy-2-methyl- (9CI)
 
Notes:
a superoxide anion generator.
  • BOC Sciences
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      Product(s):
      481-42-5 Plumbagin ≥98%
      Plumbagin, a natural 1,4-naphthoquinone first isolated from plants of the genu
       
       
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CAS Number: 481-42-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 207-569-6
FDA UNII: YAS4TBQ4OQ
Nikkaji Web: J5.778I
Beilstein Number: 1870475
MDL: MFCD00001682
XlogP3: 2.30 (est)
Molecular Weight: 188.18236000
Formula: C11 H8 O3
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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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)
 water, 1385 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
Plumbagin ≥98%
Odor: characteristic
Use: Plumbagin, a natural 1,4-naphthoquinone first isolated from plants of the genu
ExtraSynthese
For experimental / research use only.
Plumbagin (HPLC) ≥90%
Santa Cruz Biotechnology
For experimental / research use only.
Plumbagin
Sigma-Aldrich: Sigma
For experimental / research use only.
Plumbagin from Plumbago indica
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50  5 mg/kg
"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(1), Pg. 73, 1982.

intravenous-mouse LD50  7990 ug/kg
Journal of Pharmacy and Pharmacology. Vol. 48, Pg. 1128, 1996.

oral-mouse LD50  16 mg/kg
Indian Journal of Experimental Biology. Vol. 18, Pg. 876, 1980.

oral-rat LD50  65 mg/kg
Indian Journal of Medical Research. Vol. 65, Pg. 829, 1977.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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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Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 10205
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 5-hydroxy-2-methylnaphthalene-1,4-dione
Chemidplus: 0000481425
RTECS: QL8500000 for cas# 481-42-5
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References:
 5-hydroxy-2-methylnaphthalene-1,4-dione
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 10205
Pubchem (sid): 134974697
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C10387
HMDB (The Human Metabolome Database): Search
FooDB: FDB005844
Export Tariff Code: 2914.69.5000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 diospyros spp.
Search Trop  Picture
 persimmon
Search Trop  Picture
 walnut black walnut fruit
Search Trop  Picture
 walnut english walnut fruit
Search Trop  Picture
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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
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Articles:
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].
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