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5-Hydroxy-1,4-naphthalenedione

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Company Name: Capot Chemical Co.,Ltd.
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Products Intro: Product Name:5-Hydroxy-1,4-naphthoquinone
CAS:481-39-0
Purity:98%(Min,HPLC) Package:100g;1kg;5kg,10kg,25kg,50kg
Company Name: Shanghai Zheyan Biotech Co., Ltd.
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Products Intro: Product Name:5-Hydroxy-1,4-naphthalenedione
CAS:481-39-0
Purity:HPLC>=98% Package:20mg
Company Name: Chengdu Greenpure Biopharma CO.,Ltd
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Products Intro: Product Name:Juglone
CAS:481-39-0
Purity:98% Package:20mg;100mg;1g Remarks:Quinones
Company Name: Chengdu GLP biotechnology Co Ltd
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Products Intro: Product Name:Juglone
CAS:481-39-0
Purity:0.98 Package:20MG;50MG;100MG;1G;5G;1KG
Company Name: Chengdu Biopurify Phytochemicals Ltd.
Tel: 18080483897
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Products Intro: Product Name:Juglone
CAS:481-39-0
Purity:90%~98% HPLC Package:20mg;100mg;500mg;1g Remarks:BP0812

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5-Hydroxy-1,4-naphthalenedione Basic information
Product Name:5-Hydroxy-1,4-naphthalenedione
Synonyms:5-hydroxy-4-naphthalenedione;5-hydroxy-4-naphthoquinone;5-Hydroxynaphthoquinone;8-Hydroxy-1,4-naphthalenedione;8-HYDROXY-1,4-NAPHTHOQUINONE;5-HYDROXY-1,4-NAPHTHALENEDIONE;5-HYDROXY-1,4-NAPHTHLENEDIONE;5-HYDROXY-1,4-NAPHTHOQUINONE
CAS:481-39-0
MF:C10H6O3
MW:174.15
EINECS:207-567-5
Product Categories:API intermediates;Building Blocks;C10;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
Mol File:481-39-0.mol
5-Hydroxy-1,4-naphthalenedione Structure
5-Hydroxy-1,4-naphthalenedione Chemical Properties
Melting point 161-163 °C (lit.)
Boiling point 265.11°C (rough estimate)
density 1.2346 (rough estimate)
refractive index 1.5036 (estimate)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
form Crystalline Powder
pka6.59±0.20(Predicted)
color Orange to brown
Water Solubility SOLUBLE IN HOT WATER
Sensitive Light Sensitive
Merck 14,5269
BRN 1909764
CAS DataBase Reference481-39-0(CAS DataBase Reference)
NIST Chemistry Reference1,4-Naphthalenedione, 5-hydroxy-(481-39-0)
EPA Substance Registry System1,4-Naphthalenedione, 5-hydroxy- (481-39-0)
Safety Information
Hazard Codes T
Risk Statements 25-36/37/38
Safety Statements 22-26-36/37/39-45-37/39-28A
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS QJ5775000
HazardClass 6.1
PackingGroup III
HS Code 29146990
ToxicityLD50 oral in rat: 112mg/kg
MSDS Information
ProviderLanguage
Juglone English
SigmaAldrich English
ACROS English
5-Hydroxy-1,4-naphthalenedione Usage And Synthesis
DescriptionJuglone (5-hydroxynapthoquinone), is found in the leaves and other parts of walnut, hickory and pecan (1,2). Juglone is synthesized from isochorismic acid (a product of the shikimic acid pathway) and 2-oxo-glutaric acid (3). In plant tissue juglone exists as a free compound or as a glycoside (3,4). Action of a glucosidase releases 1,4,5-trihydroxynapthalene, which is then oxidized to juglone (3,4).
Chemical PropertiesOrange to brown crystalline powder
Usesantineoplastic, antifungal, antioxidant, Pin 1 inhibitor
UsesJuglone (CI Natural Brown 7; CI 75500) was isolated from the husks of walnuts in 1856. Juglone occurs in walnuts as a glycoside of its reduced form, 1,4,5-trihydroxynaphthalene. Its structure is (3) Juglone is most readily synthesized by Bernthsen s method. It is a fungicide and as such finds use in the treatment of skin diseases. Its toxic properties have been made use of in catching fish. Juglone has been used to detect very small amount of nickel salts since it gives a deep violet color with such salts.
DefinitionChEBI: A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group.
Synthesis Reference(s)The Journal of Organic Chemistry, 48, p. 5160, 1983 DOI: 10.1021/jo00174a003
Synthetic Communications, 15, p. 1177, 1985 DOI: 10.1080/00397918508077262
Synthesis, p. 644, 1977 DOI: 10.1055/s-1977-24517
PharmacologyJuglone is probably best known as the allelochemical produced by black walnut. The glucoside of juglone leaches from the leaves and branches of black walnut, where it is converted to juglone in the soil. Juglone is toxic to certain plant species and also inhibits the germination of seeds (4). Thus its allelopathic activity may be the result of both phytotoxicity and a germination inhibitor. Juglone is also antifungal (1,5) and attempts to correlate its presence with disease resistance in pecan, black walnut, and hickory to several fungal pathogens have been reported (1,2,5,6). Positive correlations have been found for resistance of juvenile leaves of black walnut to anthracnose caused by Gnomia leptostyla (5) and of some Carya species to the scab pathogen Cladosporium carygenum (2). In some pecans (C. illinoensis), juglone may act as both a preformed and an induced defense factor because concentrations of juglone increase after infection by fungi (2). No correlation between juglone glycoside concentration in pecan leaves and resistance pecan to C. carygenum has been reported (6). Free juglone and the glycosides increase after infection, but these increases could not be correlated with scab resistance (6).
Purification MethodsCrystallise Juglone from *benzene/pet ether or pet ether. [Beilstein 8 III 2558, 8 IV 2368.]
5-Hydroxy-1,4-naphthalenedione Preparation Products And Raw materials
Raw materialsN-Hydroxyphthalimide
Tag:5-Hydroxy-1,4-naphthalenedione(481-39-0) Related Product Information
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