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% ^*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
• General Description: 2-Hydroxy-1,4-naphthoquinone, also known as lawsone, is the primary bioactive compound in *Lawsonia inermis* (henna), responsible for its natural dyeing properties. The study highlights its electroactivity and degradation behavior under conditions simulating tattoo ink application, contrasting it with synthetic additives like p-Phenylenediamine (PPD). Unlike artificial dyes, lawsone’s natural origin and degradation profile suggest a lower risk of harmful byproducts, reinforcing its preference in safer body art and dyeing practices.

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-(3-phenyl-propenyl)-[1,4]naphthoquinone

2-benzhydryl-3-hydroxynaphthalene-1,4-dione

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

Refernces

Photosonoelectrochemical analysis of Lawsonia inermis (henna) and artificial dye used in tattoo and dye industry

10.1016/j.jphotochem.2018.04.026

The study focuses on the photosonoelectrochemical (PSEC) analysis of Lawsonia inermis (henna) and artificial dyes, specifically lawsone and p-Phenylenediamine (PPD), used in the tattoo and dye industry. The primary objective was to understand the degradation mechanisms and the formation of harmful byproducts when these dyes are exposed to conditions simulating those of tattoo ink application, such as UV irradiation, sonication, and electrochemical perturbations. The chemicals used in the study served various purposes: Lawsonia inermis was analyzed for its natural dye properties, lawsone as a major constituent of henna was examined for its electroactivity and degradation, and PPD, an artificial dye often added to henna for color enhancement, was assessed for its degradation products. The study aimed to demonstrate the potential harmfulness of using artificial dyes like PPD over natural dyes like henna in body art and dyeing applications.