2-Hydroxy-1,4-naphthoquinone

Base Information

• Chemical Name: 2-Hydroxy-1,4-naphthoquinone
• CAS No.: 83-72-7
• Deprecated CAS: 1985594-94-2
• Molecular Formula: C10H6O3
• Molecular Weight: 174.156
• Hs Code.: 29146990
• European Community (EC) Number: 201-496-3
• NSC Number: 27285,8625
• UNII: TLH4A6LV1W
• DSSTox Substance ID: DTXSID2025428
• Nikkaji Number: J4.642F,J2.169.330H
• Wikipedia: Lawsone
• Wikidata: Q1075492,Q104392899
• NCI Thesaurus Code: C96349
• Metabolomics Workbench ID: 52377
• ChEMBL ID: CHEMBL240963
• Mol file: 83-72-7.mol

Synonyms:2-hydroxy-1,4-naphthoquinone;2-hydroxynaphthoquinone;henna dye;lawsone;lawsone, sodium salt;lawsonin;NQ-2-OH;sodium lawsonate

Chemical Property of 2-Hydroxy-1,4-naphthoquinone

Chemical Property:

• Appearance/Colour: Yellow crystal powder
• Melting Point: 192-195 °C (dec.)(lit.)
• Refractive Index: 1.5036 (estimate)
• Boiling Point: 339.908 °C at 760 mmHg
• PKA: 4.31±0.10(Predicted)
• Flash Point: 173.572 °C
• PSA: 54.37000
• Density: 1.482 g/cm³
• LogP: 1.50750
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 2 g/L (20 ºC)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 174.031694049
• Heavy Atom Count: 13
• Complexity: 291

Purity/Quality:

99.9% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-68-36-22
• Safety Statements: 26-37/39-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant-Derived Allergens
• Canonical SMILES: C1=CC=C2C(=C1)C(=CC(=O)C2=O)O
• Recent ClinicalTrials: Testing the Effectiveness of Henna on Managing PPE
• Description: Lawsone [CAS: 83-72-7] (CI Natural Orange 6; CI 75420), also known as henna and isojuglone, occurs in the shrub henna (Lawsone alba). In England, the plant is known as Egyptian privet. The dye was extracted from the leaves of the plant, using sodium bicarbonate, and the extracts used to dye protein fibers an orange shade. Henna is probably the oldest cosmetic known. The ancient Egyptians used it as a hair dye and for staining fingernails. It is said that Mohammed dyed his beard with henna. Lawsone has been identified as 2-hydroxy-1,4-naphthoquinone. It has been synthesized by the Thiele acetylation of 1,4-naphthoquinone followed by hydrolysis and oxidation.
• Uses: 2-Hydroxy-1,4-naphthoquinone is used for preparing decorative hair and skin dyes. 2-Hydroxy-1,4-naphthoquinone also demonstrates antimicrobial and antioxidant effects. It also suppress the formation of hydrogen peroxide and superoxide radical anion by aldehyde oxidase-catalyzed reactions. antifungal, sunscreen, antibacterial, antineoplastic An antimicrobial antioxidant dye isolated from Henna.

Technology Process of 2-Hydroxy-1,4-naphthoquinone

There total 189 articles about 2-Hydroxy-1,4-naphthoquinone 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: 80.0%

4-o-nitrophenylthio-1,2-naphthoquinone (108732-56-5) → 2-hydroxynaphtho-1,4-quinone (83-72-7) + o-nitrothiophenol (4875-10-9)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 0.0333333h;

Reference yield: 63.0%

2-t-butyldimethylsilyloxy-5-formyl-6-hydroxy-2-m-methoxyphenyl-2,3-dihydronaphtho<1,2-b><1,4>dioxin → 2-hydroxynaphtho-1,4-quinone (83-72-7) + 1-(3-Methoxyphenyl)ethanone (586-37-8)

Guidance literature:

With hydrogenchloride; iron(III) chloride; In ethanol; for 3.5h; Heating;

Reference yield: 10.0%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 2-hydroxynaphtho-1,4-quinone (83-72-7) + α-naphthol (90-15-3)

Guidance literature:

In toluene; for 12h; Var_.: Aliquat 336 instead of 18-Crown-6;

DOI:10.1016/S0040-4039(01)80213-6

upstream raw materials:

1,4-Dihydroxynaphthalene

2,3-epoxy-2,3-dihydro-1,4-naphthoquinone

α-naphthol

1-methyl-4-nitrosobenzene

Downstream raw materials:

2-hydroxy-3-(morpholinomethyl)naphthalene-1,4-dione

2-hydroxy-3-phenyl-1,4-naphthoquinone

2-hydroxy-3-dodecylaminomethyl-1,4-naphthoquinone

1,4-dihydro-2-hydroxy-3-(4-methoxyphenyl)-1,4-naphthalenedione

Refernces

• 1、 Zhao, Jing,Gao, Bao-Jiao,Gong, Yong-Kuan. "Cobalt porphyrins immobilized on polymer microspheres as catalysts for the oxidation of 2-naphthol to 2-hydroxy-1,4-naphthoquinone by molecular oxygen". . p. 1808 - 1813. Retrieved 2011.
• 2、 Li, Quanmin,Zhang, Huanhuan. "Study of methanol catalyzed reaction between sodium 1,2-naphthoquine-4-sulfonate and hydroxyl ion and its application in the determination of methanol". . p. 245 - 251. Retrieved 2008.
• 3、 Grotzinger,Campbell. "". . p. 675,679. Retrieved 1972.
• 4、 Sperandeo, Norma R.,De Bertorello, Maria M.. "Synthesis and characterization of new naphthoquinonic derivatives containing the pyrazole ring: Pyrazolylnaphthoquinones". . p. 508 - 509. Retrieved 2000.
• 5、 Vidril-Robert, Daniele,Maurette, Marie-Therese,Oliveros, Esther,Hocquaux, Michel,Jacquet, Bernard. "EXEMPLE DE REACTION A L'INTERFACE SOLIDE-LIQUIDE : OXYDATION DE NAPHTALENEDIOLS PAR LE SUPEROXYDE DE POTASSIUM". . p. 529 - 532. Retrieved 1984.
• 6、 Cui, Jiahua,Jia, Jinping. "Discovery of juglone and its derivatives as potent SARS-CoV-2 main proteinase inhibitors". . . Retrieved 2021/08/25.
• 7、 -. "2, 3-dihydronaphthalo [2, 3-b] furan-4, 9-diketone compound as well as preparation method and application thereof". . . Retrieved 2020/11/05.