Juglone

Base Information

• Chemical Name: Juglone
• CAS No.: 481-39-0
• Molecular Formula: C10H6O3
• Molecular Weight: 174.156
• Hs Code.: 29146990
• European Community (EC) Number: 207-567-5
• NSC Number: 622948,153189,34266
• UNII: W6Q80SK9L6
• DSSTox Substance ID: DTXSID0031504
• Nikkaji Number: J5.777K
• Wikipedia: Juglone
• Wikidata: Q900912
• Pharos Ligand ID: LNWNWCQW47PT
• Metabolomics Workbench ID: 44554
• ChEMBL ID: CHEMBL43612
• Mol file: 481-39-0.mol

Synonyms:5-hydroxy-1,4-naphthoquinone;juglone

Chemical Property of Juglone

Chemical Property:

• Appearance/Colour: Orange to brown crystalline powder
• Vapor Pressure: 1.67E-06mmHg at 25°C
• Melting Point: 161-163 °C(lit.)
• Refractive Index: 1.662
• Boiling Point: 385.8 °C at 760 mmHg
• PKA: 6.59±0.20(Predicted)
• Flash Point: 201.3 °C
• PSA: 54.37000
• Density: 1.439 g/cm³
• LogP: 1.32740
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Light Sensitive
• Water Solubility.: SOLUBLE IN HOT WATER
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 174.031694049
• Heavy Atom Count: 13
• Complexity: 280

Purity/Quality:

98% ^*data from raw suppliers

5-Hydroxy-1,4-naphthoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 22-26-36/37/39-45-37/39-28A

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=O)C=CC2=O)C(=C1)O
• 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). 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.
• Uses: antineoplastic, antifungal, antioxidant, Pin 1 inhibitor 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. 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.

Technology Process of Juglone

There total 41 articles about Juglone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

juglone acetate (5196-28-1) → 5-hydroxynaphtho-1,4-quinone (481-39-0)

Guidance literature:

With water; trifluoroacetic acid; at 72 ℃; for 0.75h;

Reference yield: 92.0%

[1,4]naphthoquinone (130-15-4) → 5-hydroxynaphtho-1,4-quinone (481-39-0) + 5,8-Dihydroxy-1,4-naphthoquinone (475-38-7)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; trifluoroacetic acid; trifluoroacetic anhydride; bis-[(trifluoroacetoxy)iodo]benzene; at 80 ℃; for 12h; Reagent/catalyst; chemoselective reaction; Sealed tube;

DOI:10.1039/c8cc07572g

Reference yield: 92.0%

1,8-dihydroxynaphthalene (569-42-6) → 5-hydroxynaphtho-1,4-quinone (481-39-0)

Guidance literature:

With K₁₀ montmorillonite; iodic acid; for 0.366667h; Heating;

DOI:10.1007/s11178-005-0269-9

upstream raw materials:

1,8-dihydroxynaphthalene

1,5-dihydroxynaphthalene

1,4,5-trihydroxynaphthalene

5,8-dihydroxy-1-tetralone

Downstream raw materials:

juglone acetate

8-hydroxy-2-(phenylthio)naphthalene-1,4-dione

8-hydroxy-2-methoxynaphthalene-1,4-dione

2-methoxy-5-hydroxy-1,4-naphthoquinone

Refernces

• 1、 Duchstein, Hans-Juergen,Wurm, Gotthard. "Juglone Formation, an Indicator Reaction for Molecular Activated Oxygen in the Singlet State". . p. 809 - 812. Retrieved 1984.
• 2、 Maggioni, Daniela,Galli, Marco,D'Alfonso, Laura,Inverso, Donato,Dozzi, Maria Vittoria,Sironi, Laura,Iannacone, Matteo,Collini, Maddalena,Ferruti, Paolo,Ranucci, Elisabetta,D'Alfonso, Giuseppe. "A luminescent poly(amidoamine)-iridium complex as a new singlet-oxygen sensitizer for photodynamic therapy". . p. 544 - 553. Retrieved 2015.
• 3、 Sun, Kaifang,Guo, Lintong,Cai, Cheng,Hou, Zongsheng,Ren, Qizhi. "Porphyrin-Hyperbranched Copolymer Films as Recyclable Photooxidation Catalysts for 1,5-Dihydroxynaphthalene". . p. 4465 - 4469. Retrieved 2017.
• 4、 Mohrle,Folttmann. "A new synthesis of plumbagin". . p. 167 - 170. Retrieved 1988.
• 5、 Manav, Neha,Kesavan, Praseetha E.,Ishida, Masatoshi,Mori, Shigeki,Yasutake, Yuhsuke,Fukatsu, Susumu,Furuta, Hiroyuki,Gupta, Iti. "Phosphorescent rhenium-dipyrrinates: efficient photosensitizers for singlet oxygen generation". . p. 2467 - 2478. Retrieved 2019.
• 6、 Coyle, Emma E.,Joyce, Kieran,Nolan, Kieran,Oelgemoeller, Michael. "Green photochemistry: The use of microemulsions as green media in photooxygenation reactions". . p. 1544 - 1547. Retrieved 2010.
• 7、 Eberhard, Jens,Peuntinger, Katrin,Rath, Susann,Neumann, Beate,Stammler, Hans-Georg,Guldi, Dirk M.,Mattay, Jochen. "A study of acridine and acridinium-substituted bis(terpyridine)zinc(ii) and ruthenium(ii) complexes as photosensitizers for O2 ( 1Δg) generation". . p. 380 - 396. Retrieved 2014.
• 8、 Nakai, Hidetaka,Kitagawa, Kazuhiro,Nakamori, Harutaka,Tokunaga, Taisuke,Matsumoto, Takahiro,Nozaki, Koichi,Ogo, Seiji. "Reversible switching of the luminescence of a photoresponsive gadolinium(III) complex". . p. 8722 - 8725. Retrieved 2013.
• 9、 Grundmann. "A new synthesis of juglone". . p. 644 - 645. Retrieved 1977.
• 10、 Zhu, Jing,Sun, Gang. "Preparation and photo-oxidative functions of poly(ethylene-co-methacrylic acid) (PE-co-MAA) nanofibrous membrane supported porphyrins". . p. 10581 - 10588. Retrieved 2012.