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
- MDL Number:
- MFCD00001684
- MOL File:
- 481-39-0.mol
- MSDS File:
- SDS
| 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) |
| FDA UNII | W6Q80SK9L6 |
| 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(30)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | H47003 | 5-Hydroxy-1,4-naphthoquinone 97% | 481-39-0 | 1g | $74.8 | 2024-03-01 | Buy |
| Sigma-Aldrich | 420120 | Juglone | 481-39-0 | 250mg | $82.8 | 2024-03-01 | Buy |
| TCI Chemical | H0286 | 5-Hydroxy-1,4-naphthoquinone >97.0%(GC) | 481-39-0 | 1g | $100 | 2024-03-01 | Buy |
| TCI Chemical | H0286 | 5-Hydroxy-1,4-naphthoquinone >97.0%(GC) | 481-39-0 | 5g | $382 | 2024-03-01 | Buy |
| Alfa Aesar | H28343 | 5-Hydroxy-1,4-naphthoquinone, 99% | 481-39-0 | 1g | $48.65 | 2024-03-01 | 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).
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
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.
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.]
5-Hydroxy-1,4-naphthalenedione Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Shaanxi Cuikang Pharmaceutical Technology Co., Ltd | +8618829768577 | gao490372054@gamil.com | China | 1250 | 58 |
| Zibo Hangyu Biotechnology Development Co., Ltd | +86-0533-2185556 +8617865335152 | Mandy@hangyubiotech.com | China | 11013 | 58 |
| Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29797 | 60 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21691 | 55 |
| Shanghai Zheyan Biotech Co., Ltd. | 18017610038 | zheyansh@163.com | CHINA | 3620 | 58 |
| Chengdu Greenpure Biopharma CO.,Ltd | 18283602253 | jancyzheng@gcgreenpure.com | China | 952 | 58 |
| Chengdu GLP biotechnology Co Ltd | 028-87075086 13350802083 | scglp@glp-china.com | CHINA | 1824 | 58 |
| Shenzhen Nexconn Pharmatechs Ltd | +86-755-89396905 +86-15013857715 | admin@nexconn.com | China | 10248 | 58 |
| Hubei Jusheng Technology Co.,Ltd. | 18871490254 | linda@hubeijusheng.com | CHINA | 28180 | 58 |
| Shaanxi Pioneer Biotech Co., Ltd . | +8613259417953 | sales@pioneerbiotech.com | China | 3000 | 58 |
View Lastest Price from 5-Hydroxy-1,4-naphthalenedione manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-01-02 | 5-Hydroxy-1,4-naphthalenedione
481-39-0
|
US $55.00-550.00 / kg | 10kg | 0.99 | 20tons | Zibo Hangyu Biotechnology Development Co., Ltd | |
 |
2020-01-08 | 5-Hydroxy-1,4-naphthalenedione
481-39-0
|
US $2.00 / KG | 1KG | 98% | 100g , 1kg, 5kg , 50kg | Career Henan Chemical Co |
-
- 5-Hydroxy-1,4-naphthalenedione
481-39-0
- US $55.00-550.00 / kg
- 0.99
- Zibo Hangyu Biotechnology Development Co., Ltd
-
- 5-Hydroxy-1,4-naphthalenedione
481-39-0
- US $2.00 / KG
- 98%
- Career Henan Chemical Co