83-72-7 Usage
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.
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.
Application
2-Hydroxy-1,4-naphthoquinone(HNQ) is the principal natural dye ingredient contained at 1.0-1.4% in the leaves of Henna (Lawsonia inermis). It is an ancient red-orange dye. Henna has been used for more than 4000 years not only as a hair dye, but also as a body paint and tattoo dye. Today, semi-permanent hair dyes containing Henna as well as its pure dye ingredient HNQ are widely used and have become increasingly popular due to their natural origin.
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.
Chemical Properties
Yellow crystal powder
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.
Uses
Different sources of media describe the Uses of 83-72-7 differently. You can refer to the following data:
1. 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.
2. antifungal, sunscreen, antibacterial, antineoplastic
3. An antimicrobial antioxidant dye isolated from Henna.
Definition
A coloring principle obtained from dried leaves of certain tropical plants (North Africa, India).
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
General Description
Yellow prisms or yellow powder.
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.
Menadione structure-based novel coronavirus 3CL protease inhibitor
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Paragraph 0036-0039, (2021/04/14)
The invention discloses a menadione derivative capable of resisting novel coronavirus and medical application of the menadione derivative. The structure of the compound is shown as a formula (I), in the formula, R is a hydrogen atom, methyl, acetyl or hydroxyl, and R1 is hydrogen, methoxy, benzyloxy or benzoyloxy. The compound disclosed by the invention can inhibit the 3CL hydrolase of the 2019-nCoV novel coronavirus, and has the activity of resisting the novel coronavirus. In-vitro activity determination experiments show that the enzyme inhibition rate of part of the compounds reaches 90% or above under the concentration of 1 [mu] M, and is significantly superior to that of a positive control drug alkannin. Cell-level toxicity test experiment results show that the toxicity of menadione and the derivative thereof to host normal cells HSF is significantly lower than that of positive drugs alkannin and juglone, and part of the compounds show relatively strong anti-novel coronavirus activity in vitro, and have an important significance for the development of high-efficiency and low-toxicity new anti-novel coronavirus drugs.
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.