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
- Molecular Weight:
- 174.15
- MOL File:
- 481-39-0.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/11/10 16:48:32
| 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 |
| form | Crystalline Powder |
| pka | 6.59±0.20(Predicted) |
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H301 | |||||||||
| Precautionary statements | P264-P270-P301+P310-P405-P501 | |||||||||
| 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 | |||||||||
| NFPA 704 |
|
5-Hydroxy-1,4-naphthalenedione price More Price(7)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | H47003 | 5-Hydroxy-1,4-naphthoquinone 97% | 481-39-0 | 1G | ₹4698.05 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | H47003 | 5-Hydroxy-1,4-naphthoquinone 97% | 481-39-0 | 5G | ₹17341.65 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 420120 | Juglone - CAS 481-39-0 - Calbiochem A highly selective cell-permeable, irreversible inhibitor of PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family). | 481-39-0 | 250MG | ₹6990 | 2022-06-14 | Buy |
| TCI Chemicals (India) | H0286 | 5-Hydroxy-1,4-naphthoquinone min. 96.0 % | 481-39-0 | 1G | ₹3700 | 2022-05-26 | Buy |
| ALFA India | ALF-H28343-06 | 5-Hydroxy-1,4-naphthoquinone, 99% | 481-39-0 | 5g | ₹13363 | 2022-05-26 | Buy |
5-Hydroxy-1,4-naphthalenedione Chemical Properties,Uses,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
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.
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
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| OCEAN TRADING CORPORATION | +91(22) 24921669 | New Delhi, India | 6211 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| CHEMSWORTH | +91-261-2397244 | New Delhi, India | 6707 | 30 | Inquiry |
| Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6913 | 58 | Inquiry |
| Acme Sujan Chemicals Private Limited | 08048372475Ext 327 | Maharashtra, India | 32 | 58 | Inquiry |
| Shaanxi Cuikang Pharmaceutical Technology Co., Ltd | +8618829768577 | China | 1250 | 58 | Inquiry |
| Zibo Hangyu Biotechnology Development Co., Ltd | +86-0533-2185556 +8617865335152 | China | 11027 | 58 | Inquiry |
| Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | China | 29798 | 60 | Inquiry |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | China | 21676 | 55 | Inquiry |
| Chengdu Greenpure Biopharma CO.,Ltd | +8618283602253 | China | 952 | 58 | Inquiry |
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