5-Hydroxy-1,4-naphthalenedione CAS NO.481-39-0

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
Mol File:    481-39-0.mol

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
pka    6.59±0.20(Predicted)
form     Crystalline Powder
color     Orange to brown
Water Solubility     SOLUBLE IN HOT WATER
Sensitive     Light Sensitive
Merck     14,5269
BRN     1909764
CAS DataBase Reference    481-39-0(CAS DataBase Reference)
NIST Chemistry Reference    1,4-Naphthalenedione, 5-hydroxy-(481-39-0)
EPA Substance Registry System    1,4-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
Toxicity    LD50 oral in rat: 112mg/kg
MSDS Information
Provider    Language
Juglone    English
SigmaAldrich    English
ACROS    English
5-Hydroxy-1,4-naphthalenedione Usage And Synthesis
Description    Juglone (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 Properties    Orange to brown crystalline powder
Uses    antineoplastic, antifungal, antioxidant, Pin 1 inhibitor
Uses    Juglone (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.
Definition    ChEBI: 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
Pharmacology    Juglone 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 Methods    Crystallise 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 materials    N-Hydroxyphthalimide