Description Chemical Propterties Application Biological Toxicity
ChemicalBook > CAS DataBase List > 2-Hydroxy-1,4-naphoquinone

2-Hydroxy-1,4-naphoquinone

Description Chemical Propterties Application Biological Toxicity
Product Name
2-Hydroxy-1,4-naphoquinone
CAS No.
83-72-7
Chemical Name
2-Hydroxy-1,4-naphoquinone
Synonyms
LAWSONE;2-Hydroxynaphthalene-1,4-dione;2-HYDROXY-1,4-NAPHTHOQUINONE;Lawson;Henna;2-Hydroxynaphthoquinone;3-Hydroxy-1,4-naphthoquinone;Hana;Mendi;Mehendi
CBNumber
CB2493073
Molecular Formula
C10H6O3
Formula Weight
174.15
MOL File
83-72-7.mol
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2-Hydroxy-1,4-naphoquinone Property

Melting point:
192-195 °C (dec.)(lit.)
Boiling point:
265.11°C (rough estimate)
Density 
1.2346 (rough estimate)
refractive index 
1.5036 (estimate)
storage temp. 
Sealed in dry,Room Temperature
solubility 
Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
form 
Crystalline Powder
pka
4.31±0.10(Predicted)
Colour Index 
75480
color 
Yellow
Water Solubility 
2 g/L (20 ºC)
Merck 
14,5393
BRN 
1565260
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
CSFWPUWCSPOLJW-UHFFFAOYSA-N
LogP
1.380
CAS DataBase Reference
83-72-7(CAS DataBase Reference)
NIST Chemistry Reference
1,4-Naphthalenedione, 2-hydroxy-(83-72-7)
EPA Substance Registry System
2-Hydroxy-1,4-naphthoquinone (83-72-7)
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Safety

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-68-36-22
Safety Statements 
26-37/39-36/37/39-36
WGK Germany 
3
RTECS 
QL8200000
TSCA 
Yes
HS Code 
29146990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H46805
Product name
2-Hydroxy-1,4-naphthoquinone
Purity
97%
Packaging
10g
Price
$39.7
Updated
2024/03/01
Sigma-Aldrich
Product number
H46805
Product name
2-Hydroxy-1,4-naphthoquinone
Purity
97%
Packaging
25g
Price
$66.1
Updated
2024/03/01
TCI Chemical
Product number
H0285
Product name
2-Hydroxy-1,4-naphthoquinone
Purity
>98.0%(T)
Packaging
25g
Price
$41
Updated
2024/03/01
TCI Chemical
Product number
H0285
Product name
2-Hydroxy-1,4-naphthoquinone
Purity
>98.0%(T)
Packaging
100g
Price
$112
Updated
2024/03/01
Alfa Aesar
Product number
A11880
Product name
2-Hydroxy-1,4-naphthoquinone, 98+%
Packaging
10g
Price
$25.5
Updated
2024/03/01
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2-Hydroxy-1,4-naphoquinone Chemical Properties,Usage,Production

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

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.

Uses

antifungal, sunscreen, antibacterial, antineoplastic

Uses

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/jo00239a023
Tetrahedron 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.]

2-Hydroxy-1,4-naphoquinone Preparation Products And Raw materials

Raw materials

Ammonium sulfamate 1,4-Naphthoquinone 1,2-NAPHTHOQUINONE

Preparation Products

Nile Red
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View Lastest Price from 2-Hydroxy-1,4-naphoquinone manufacturers

Hebei Dangtong Import and export Co LTD
Product
2-Hydroxy-1,4-naphoquinone 83-72-7
Price
US $450.00-400.00/kg
Min. Order
100kg
Purity
99.99%
Supply Ability
100Tons
Release date
2023-03-06
Hebei Fengqiang Trading Co., LTD
Product
2-Hydroxy-1,4-naphoquinone 83-72-7
Price
US $100.00/bag
Min. Order
1bag
Purity
99
Supply Ability
5000
Release date
2023-09-14
Henan Bao Enluo International TradeCo.，LTD
Product
2-Hydroxy-1,4-naphoquinone 83-72-7
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000tons
Release date
2023-07-11

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