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
JUGLONE;5-HYDROXY-1,4-NAPHTHOQUINONE;5-hydroxynaphthalene-1,4-dione;Nucin;Akhnot;Iuglon;Juglon;Yuglon;Juglane;Jugnlon
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
solubility 
DMSO: 10 mg/ml; Ethanol: 10 mg/ml
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
LogP
1.920
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

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H47003
Product name
5-Hydroxy-1,4-naphthoquinone
Purity
97%
Packaging
1g
Price
$74.8
Updated
2024/03/01
Sigma-Aldrich
Product number
420120
Product name
Juglone
Packaging
250mg
Price
$82.8
Updated
2024/03/01
TCI Chemical
Product number
H0286
Product name
5-Hydroxy-1,4-naphthoquinone
Purity
>97.0%(GC)
Packaging
1g
Price
$100
Updated
2024/03/01
TCI Chemical
Product number
H0286
Product name
5-Hydroxy-1,4-naphthoquinone
Purity
>97.0%(GC)
Packaging
5g
Price
$382
Updated
2024/03/01
Alfa Aesar
Product number
H28343
Product name
5-Hydroxy-1,4-naphthoquinone, 99%
Packaging
1g
Price
$48.65
Updated
2024/03/01
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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).

Description

Juglone is a natural naphthoquinone found in the black walnut (J. nigra) and other plants in the Juglandaceae family. It has allelopathic actions, suppressing growth, photosynthesis, and respiration in plants and other organisms, although some bacteria can metabolize juglone. Juglone also irreversibly inhibits peptidyl-prolyl cis/trans isomerases of the parvulin family, including human Pin1, yeast Ess1/Ptf1, and E. coli parvulin (Ki = 55.9 nM). Juglone also blocks transcription by RNA polymerases I, II, and III (IC50s = 2-7 μM) and attenuates kidney fibrosis in rats treated with unilateral ureteral obstruction, both through Pin1-independent mechanisms.

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.

Uses

5-Hydroxy-1,4-naphthoquinone is used as a natural dye in cloth, fabrics, wool and ink. It is a coloring agent for food and cosmetics. It is involved in the synthesis of poly(hydroxyl-1,4-naphthoquinone) stabilized gold nanoparticles (AuNQ NPs), which is used for nonenzymatic electrochemical detection of glucose.

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

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

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

Preparation Products

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5-Hydroxy-1,4-naphthalenedione Suppliers

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View Lastest Price from 5-Hydroxy-1,4-naphthalenedione manufacturers

Zibo Hangyu Biotechnology Development Co., Ltd
Product
5-Hydroxy-1,4-naphthalenedione 481-39-0
Price
US $55.00-550.00/kg
Min. Order
10kg
Purity
0.99
Supply Ability
20tons
Release date
2023-11-10
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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