| Identification | More | [Name]
5-Hydroxy-1,4-naphthalenedione | [CAS]
481-39-0 | [Synonyms]
5-HYDROXY-1,4-NAPHTHALENEDIONE
5-HYDROXY-1,4-NAPHTHLENEDIONE
5-HYDROXY-1,4-NAPHTHOQUINONE
5-HYDROXY-P-NAPHTHOQUINONE
8-HYDROXY-1,4-NAPHTHOQUINONE
JUGLONE
RARECHEM BW GC 0025
WALNUT EXTRACT
WALNUT EXTRACT, WATER SOLUBLE
1,4-Naphthalenedione,5-hydroxy-
1,4-Naphthoquinone, 5-hydroxy-
1,4-Naphthoquinone, 8-hydroxy-
4-Naphthalenedione,5-hydroxy-1
5-Hydroxy-1,4-naftochinon
5-hydroxy-4-naphthalenedione
5-hydroxy-4-naphthoquinone
5-Hydroxynaphthoquinone
8-Hydroxy-1,4-naphthalenedione
8-hydroxy-4-naphthoquinone
Akhnot | [EINECS(EC#)]
207-567-5 | [Molecular Formula]
C10H6O3 | [MDL Number]
MFCD00001684 | [Molecular Weight]
174.15 | [MOL File]
481-39-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Orange to brown crystalline powder | [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) | [solubility ]
DMSO: 10 mg/ml; Ethanol: 10 mg/ml | [form ]
Crystalline Powder | [pka]
6.59±0.20(Predicted) | [color ]
Orange to brown | [Water Solubility ]
SOLUBLE IN HOT WATER | [Sensitive ]
Light Sensitive | [Merck ]
5269 | [BRN ]
1909764 | [InChI]
1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H | [InChIKey]
KQPYUDDGWXQXHS-UHFFFAOYSA-N | [SMILES]
Oc1cccc2C(=O)C=CC(=O)c12 | [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]
481-39-0(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H301 | [Precautionary statements ]
P264-P270-P301+P310-P405-P501 | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
QJ5775000
| [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29146990 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral | [Toxicity]
LD50 oral in rat: 112mg/kg |
| Hazard Information | Back Directory | [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 | [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.] | [References]
[1] A A HEJL J A R F A Einhellig. Effects of juglone on growth, photosynthesis, and respiration.[J]. Journal of Chemical Ecology, 1993, 19 3: 559-568. DOI: 10.1007/bf00994325
[2] LARS HENNIG. Selective Inactivation of Parvulin-Like Peptidyl-Prolyl cis/trans Isomerases by Juglone?[J]. Biochemistry Biochemistry, 1998, 37 17: 5953-5960. DOI: 10.1021/bi973162p
[3] SHENG-HAO CHAO D H P A Greenleaf. Juglone, an inhibitor of the peptidyl-prolyl isomerase Pin1, also directly blocks transcription.[J]. Nucleic Acids Research, 2001, 29 3 1: 767-773. DOI: 10.1093/nar/29.3.767
[4] SHANNON REESE. The Pin 1 inhibitor juglone attenuates kidney fibrogenesis via Pin 1-independent mechanisms in the unilateral ureteral occlusion model.[J]. Fibrogenesis & Tissue Repair, 2010: 1. DOI: 10.1186/1755-1536-3-1 |
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