ChemicalBook > CAS DataBase List > 5-Hydroxy-1,4-naphthalenedione

5-Hydroxy-1,4-naphthalenedione

Product Name
5-Hydroxy-1,4-naphthalenedione
CAS No.
481-39-0
Chemical Name
5-Hydroxy-1,4-naphthalenedione
Synonyms
Nucin;Akhnot;Iuglon;Juglon;Yuglon;JUGLONE;Juglane;Jugnlon;NCI 2323;Regianin
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. 
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)
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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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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H47003
Product name
5-Hydroxy-1,4-naphthoquinone
Purity
97%
Packaging
1g
Price
$55.4
Updated
2021/03/22
Sigma-Aldrich
Product number
420120
Product name
Juglone
Packaging
250mg
Price
$64.19
Updated
2021/03/22
TCI Chemical
Product number
H0286
Product name
5-Hydroxy-1,4-naphthoquinone
Purity
>97.0%(GC)
Packaging
1g
Price
$46
Updated
2021/03/22
TCI Chemical
Product number
H0286
Product name
5-Hydroxy-1,4-naphthoquinone
Purity
>97.0%(GC)
Packaging
5g
Price
$177
Updated
2021/03/22
Alfa Aesar
Product number
H28343
Product name
5-Hydroxy-1,4-naphthoquinone, 99%
Packaging
1g
Price
$45.9
Updated
2021/03/22
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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.

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

Preparation Products

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5-Hydroxy-1,4-naphthalenedione Suppliers

Chongqing Xingcan Pharmaceutical Technology Co., Ltd.
Email
xingcanyaoye@sina.com;
Country
China
ProdList
2050
Advantage
58
Nanjing tongen Pharmaceutical Technology Co., Ltd
Email
573402285@qq.com
Country
China
ProdList
158
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40264
Advantage
62
Chembest Research Laboratories Limited
Tel
021-20908456-
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
5948
Advantage
61
Alfa Aesar
Tel
400-610-6006; 021-67582000
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30159
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24555
Advantage
81
Energy Chemical
Tel
021-58432009-
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
43504
Advantage
61
Shanghai Hanhong Scientific Co.,Ltd.
Tel
;021-54306202- ;
Email
jerry.ma@hanhonggroup.com;jerry.ma@hanhonggroup.com;jerry.ma@hanhonggroup.com
Country
China
ProdList
43232
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32358
Advantage
50
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View Lastest Price from 5-Hydroxy-1,4-naphthalenedione manufacturers

Career Henan Chemical Co
Product
5-Hydroxy-1,4-naphthalenedione 481-39-0
Price
US $2.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
100g , 1kg, 5kg , 50kg
Release date
2020-01-07

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