83-72-7 Usage
Description
2-Hydroxy-1,4-naphthoquinone, also known as lawsone or henna, is a natural dye ingredient derived from the leaves of the henna plant (Lawsonia inermis). It is a yellow crystal powder with a chemical structure that allows it to act as an antimicrobial and antioxidant agent. 2-Hydroxy-1,4-naphoquinone has been used for over 4000 years as a red-orange dye for hair, body paint, and tattoos.
Uses
Used in Cosmetic Industry:
2-Hydroxy-1,4-naphthoquinone is used as a natural dye for decorative hair and skin applications, providing a red-orange color to the hair and skin. It is valued for its natural origin and has become increasingly popular in semi-permanent hair dyes.
Used in Antimicrobial Applications:
2-Hydroxy-1,4-naphthoquinone demonstrates antimicrobial properties, making it useful in various applications to inhibit the growth of microorganisms.
Used in Antioxidant Applications:
As an antioxidant, 2-Hydroxy-1,4-naphthoquinone helps suppress the formation of hydrogen peroxide and superoxide radical anion by aldehyde oxidase-catalyzed reactions, providing protection against oxidative stress.
Used in Antifungal Applications:
2-Hydroxy-1,4-naphthoquinone is used as an antifungal agent, helping to prevent fungal infections.
Used in Sunscreen Applications:
Due to its ability to absorb ultraviolet radiation, 2-Hydroxy-1,4-naphthoquinone can be used as a component in sunscreen products to protect the skin from harmful UV rays.
Used in Antibacterial Applications:
2-Hydroxy-1,4-naphoquinone is used as an antibacterial agent, helping to prevent bacterial infections.
Used in Antineoplastic Applications:
2-Hydroxy-1,4-naphthoquinone has potential antineoplastic properties, which may be useful in the development of treatments for cancer.
Used in Henna Dye Preparation:
As an antimicrobial antioxidant dye isolated from henna, 2-Hydroxy-1,4-naphthoquinone is the principal natural dye ingredient in henna, making up 1.0-1.4% of the leaves of the henna plant. It has been used for centuries as a hair dye, body paint, and tattoo dye.
Chemical Propterties
2-Hydroxy-1,4-naphthoquinone (HNQ, C10H6O3) is also called Lawsone, which is a white cubic crystal. Its melting point is 192-195 oC, and flash point is 192 oC. The solubility of HNQ is 2 g/L in water at 20 oC. It is stable, but it is combustible and incompatible with strong oxidizing agents.
Biological Toxicity
2-Hydroxy-1,4-naphoquinone(HNQ) was reported to be a weak bacterial mutagen for Salmonella typhimurium strain TA98 or was more clearly mutagenic for strain TA 2637, both in the presence of metabolic activation. HNQ was unable to induce sex-linked recessive lethal mutations in Drosophila melanogaster. The available data suggest that the use of Henna or 2-Hydroxy-1,4-naphoquinone(HNQ) for hair dyeing presents no or negligible risk of genotoxicity to the consumer.
History
Lawsone (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.
Synthesis Reference(s)
The Journal of Organic Chemistry, 53, p. 808, 1988 DOI: 10.1021/jo00239a023Tetrahedron Letters, 25, p. 533, 1984 DOI: 10.1016/S0040-4039(00)99930-1
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Phenols, such as 2-Hydroxy-1,4-naphoquinone, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Many of them form metal salts that tend toward detonation by rather mild shock.
Health Hazard
ACUTE/CHRONIC HAZARDS: 2-Hydroxy-1,4-naphoquinone may be absorbed through the skin and can cause skin irritation.
Fire Hazard
Flash point data for 2-Hydroxy-1,4-naphoquinone are not available but 2-Hydroxy-1,4-naphoquinone is probably combustible.
Contact allergens
Henna, prepared by powdering the dried leaves of henna plant (Lawsonia inermis L.), is used for coloring and conditioning hair and nails, particularly by Muslims or Hindus. It contains Lawsone, which very rarely induces contact allergy. Most dermatitis caused by “black henna” is due to PPD and derivatives
Purification Methods
Crystallise Lawsone B from *C6H6 or AcOH (m 192.5o, 195-196o). It sublimes in a vacuum (m 194o). It has UV with max at 455nm (aqueous NaOH). [Beilstein 8 H 300, 8 I 635, 8 II 344, 8 III 2543, 8 IV 2360.]
Check Digit Verification of cas no
The CAS Registry Mumber 83-72-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 3 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 83-72:
(4*8)+(3*3)+(2*7)+(1*2)=57
57 % 10 = 7
So 83-72-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H
83-72-7Relevant articles and documents
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Molho,Mentzer
, p. 11 (1950)
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Rhodium(II)-catalyzed reaction of 1,3-bis(diazo)indan-2-one with alcohols: Formation of unexpected 1,1-dialkoxy ketones
Murata, Shigeru,Kongou, Chiharu,Tomioka, Hideo
, p. 1499 - 1502 (1995)
The rhodium(II)-catalyzed decomposition of 1,3-bis(diazo)indan-2-one (1) in boiling dichloromethane containing primary alcohols gave 1,1-dialkoxyindan-2-ones (2) in good yields without any formation of 1,3-dialkoxy derivatives.
Isoxazoles. 10. Degradation and enolization kinetics of 4- aminoisoxazolyl-1,2-naphthoquinone in basic aqueous solution
Ortiz,De Bertorello
, p. 783 - 785 (1995)
The kinetics of enolization and degradation of N-(5-methyl-4-isoxazolyl)- 4-amino-1,2-naphthoquinone (1) was investigated in aqueous solutions over a pH range of 7.30 to 12.25, at 35 °C and at constant ionic strength (μ = 0.5) using reversed-phase HPLC. Pseudo-first-order kinetics was observed throughout the pH range studied. The rate of enolization (k(e)), the keto- enol equilibrium constant (K(t)), and specific base catalysis rate constant (k(OH)) were determined. Good agreement between the theoretical pH-rate profile and the experimental data supports the proposed transformation process. The average recovery for 1 and its tautomerization product 2- hydroxy-N-(5-methyl-4-isoxazolyl)-1,4-naphthoquinone 4-imine (2) from mixtures of different composition was evaluated.
Sullivan,Hess
, p. 47 (1936)
Isoxazoles. 9. Degradation kinetics of 4-(isoxazolylamino)-1,2- naphthoquinone in acidic aqueous solution
Ortiz,De Bertorello
, p. 1457 - 1460 (1994)
The degradation kinetics of N-(5-methyl-4-isoxazolyl)-4-amino-1,2- naphthoquinone (1) was studied in aqueous solution over a pH range of 0.65- 7.50, at 35 °C and at a constant ionic strength of 0.5. The degradation rates were determined by high-pressure liquid chromatography and were observed to follow pseudo-first-order kinetics with respect to the concentration of 1. The pH-rate profile was linear with slope -1 under acidic pH, becoming pH independent from 3.50 to 7.50. Good agreement between the theoretical pH-rate profile and the experimental data supports the proposed degradation process. The catalytic rate constants for hydrogen ion and water were k(H) = 0.901 M-1 h-1 and k(o) = 1.34 x 10-3 h-1, respectively. These data are appropriate to develop a stable dosage form of 1. The accuracy, peak sharpness, and asymmetry factor for the analytical method were determined.
Discovery of juglone and its derivatives as potent SARS-CoV-2 main proteinase inhibitors
Cui, Jiahua,Jia, Jinping
supporting information, (2021/08/25)
SARS-CoV-2 as a positive-sense single-stranded RNA coronavirus caused the global outbreak of COVID-19. The main protease (Mpro) of the virus as the major enzyme processing viral polyproteins contributed to the replication and transcription of SARS-CoV-2 in host cells, and has been characterized as an attractive target in drug discovery. Herein, a set of 1,4-naphthoquinones with juglone skeleton were prepared and evaluated for the inhibitory efficacy against SARS-CoV-2 Mpro. More than half of the tested naphthoquinones could effectively inhibit the target enzyme with an inhibition rate of more than 90% at the concentration of 10 μM. In the structure-activity relationships (SARs) analysis, the characteristics of substituents and their position on juglone core scaffold were recognized as key ingredients for enzyme inhibitory activity. The most active compound, 2-acetyl-8-methoxy-1,4-naphthoquinone (15), which exhibited much higher potency in enzyme inhibitions than shikonin as the positive control, displayed an IC50 value of 72.07 ± 4.84 nM towards Mpro-mediated hydrolysis of the fluorescently labeled peptide. It fit well into the active site cavity of the enzyme by forming hydrogen bonds with adjacent amino acid residues in molecular docking studies. The results from in vitro antiviral activity evaluation demonstrated that the most potent Mpro inhibitor could significantly suppress the replication of SARS-CoV-2 in Vero E6 cells within the low micromolar concentrations, with its EC50 value of about 4.55 μM. It was non-toxic towards the host Vero E6 cells under tested concentrations. The present research work implied that juglone skeleton could be a primary template for the development of potent Mpro inhibitors.
ELECTROLYTE INCLUDING MIXTURE OF ACTIVE MATERIAL AND PRECURSOR THEREOF
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Paragraph 0055-0059, (2021/10/02)
An electrolyte including a mixture of hydroxynaphtoquinone and a precursor material thereof is provided. The electrolyte may achieve higher capacities.
Naphtho[2,3-: B] furan-4,9-dione synthesis via palladium-catalyzed reverse hydrogenolysis
Li, Jimei,Zhang, Jie,Li, Mingfei,Zhang, Chenyang,Yuan, Yongkun,Liu, Renhua
supporting information, p. 2348 - 2351 (2019/02/27)
A reverse hydrogenolysis process has been developed for two-site coupling of 2-hydroxy-1,4-naphthoquinones with olefins to produce naphtha[2,3-b]furan-4,9-diones and hydrogen (H2). The reaction is catalyzed by commercially available Pd/C without oxidants and hydrogen acceptors, thereby providing an intrinsically waste-free approach for the synthesis of functionalized and potentially biologically relevant naphtha[2,3-b]furan-4,9-diones.