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5-Hydroxy-1,4-naphthalenedione

Product Name:
5-Hydroxy-1,4-naphthalenedione
CAS No.
481-39-0
Chemical Name:
5-Hydroxy-1,4-naphthalenedione
CBNumber:
CB5447002
Molecular Formula:
C10H6O3
Formula Weight:
174.15
MOL File:
481-39-0.mol
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5-Hydroxy-1,4-naphthalenedione Property

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. 
Refrigerator (+4°C)
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)
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Safety

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
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N-Bromosuccinimide Price More Price(9)

Sigma-Aldrich Gold
Product number:
H47003
Product name :
5-Hydroxy-1,4-naphthoquinone
Purity:
97%
Packaging:
1g
Price:
$53
Updated:
2019/12/02
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Buy
Sigma-Aldrich Gold
Product number:
420120
Product name :
Juglone
Packaging:
250mg
Price:
$64.4
Updated:
2019/12/02
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Buy
TCI Chemical Gold
Product number:
H0286
Product name :
5-Hydroxy-1,4-naphthoquinone
Purity:
>97.0%(GC)
Packaging:
1g
Price:
$44
Updated:
2020/06/24
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TCI Chemical Gold
Product number:
H0286
Product name :
5-Hydroxy-1,4-naphthoquinone
Purity:
>97.0%(GC)
Packaging:
5g
Price:
$153
Updated:
2020/06/24
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Buy
Alfa Aesar Gold
Product number:
H28343
Product name :
5-Hydroxy-1,4-naphthoquinone, 99%
Packaging:
5g
Price:
$128
Updated:
2020/06/24
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Buy
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5-Hydroxy-1,4-naphthalenedione Chemical Properties,Usage,Production

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.

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

Raw materials

Preparation Products

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5-Hydroxy-1,4-naphthalenedione Suppliers

Global(139)Suppliers
Chongqing Xingcan Pharmaceutical Technology Co., Ltd.
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