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2-Hydroxy-1,4-naphoquinone

2-Hydroxy-1,4-naphoquinone Structure
2-Hydroxy-1,4-naphoquinone structure
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
Molecular Weight:
174.15
MDL Number:
MFCD00001678
MOL File:
83-72-7.mol
MSDS File:
SDS
Last updated:2023-09-14 16:39:47
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2-Hydroxy-1,4-naphoquinone Properties

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)
pka 4.31±0.10(Predicted)
Colour Index 75480
form Crystalline Powder
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)
FDA 21 CFR 73.2190
EWG's Food Scores 1-6
FDA UNII TLH4A6LV1W
NIST Chemistry Reference 1,4-Naphthalenedione, 2-hydroxy-(83-72-7)
EPA Substance Registry System 2-Hydroxy-1,4-naphthoquinone (83-72-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
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
NFPA 704
1
2 0

2-Hydroxy-1,4-naphoquinone price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich H46805 2-Hydroxy-1,4-naphthoquinone 97% 83-72-7 10g $39.7 2024-03-01 Buy
Sigma-Aldrich H46805 2-Hydroxy-1,4-naphthoquinone 97% 83-72-7 25g $66.1 2024-03-01 Buy
TCI Chemical H0285 2-Hydroxy-1,4-naphthoquinone >98.0%(T) 83-72-7 25g $41 2024-03-01 Buy
TCI Chemical H0285 2-Hydroxy-1,4-naphthoquinone >98.0%(T) 83-72-7 100g $112 2024-03-01 Buy
Alfa Aesar A11880 2-Hydroxy-1,4-naphthoquinone, 98+% 83-72-7 10g $25.5 2024-03-01 Buy
Product number Packaging Price Buy
H46805 10g $39.7 Buy
H46805 25g $66.1 Buy
H0285 25g $41 Buy
H0285 100g $112 Buy
A11880 10g $25.5 Buy

2-Hydroxy-1,4-naphoquinone Chemical Properties,Uses,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

An antimicrobial antioxidant dye isolated from Henna.

Uses

antifungal, sunscreen, antibacterial, antineoplastic

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.

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 naphthalene-1,2,4-triyl triacetate naphthalene-1,2,4-triol
2-Naphthalenol, 1,4-dimethoxy- 1,3-DIHYDROXYNAPHTHALENE 2-METHOXY-1,4-NAPHTHOQUINONE 4-methoxynaphthalene-1,2-dione 1,2-DIHYDROXYNAPHTHALENE
2-Chloro-3-hydroxy-1,4-naphthoquinone 2-hydroxy-3-iodonaphthalene-1,4-dione 1,4-Dihydroxynaphthalene 2-Naphthol 1-Tetralone
2-Methoxynaphthalene 2-NITROTHIOPHENOL

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Preparation Products

Nile Red 2-Chloro-1,4-naphthoquinone

2-Hydroxy-1,4-naphoquinone Suppliers

Global( 376)Suppliers
Supplier Tel Email Country ProdList Advantage
Henan Bao Enluo International TradeCo.，LTD 		+86-17331933971 +86-17331933971 deasea125996@gmail.com China 2503 58
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21691 55
Shanghai Zheyan Biotech Co., Ltd. 		18017610038 zheyansh@163.com CHINA 3620 58
career henan chemical co 		+86-0371-86658258 sales@coreychem.com China 29914 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD 		+86 18953170293 sales@sdzschem.com China 2931 58
Jinan Carbotang Biotech Co.,Ltd. 		+8615866703830 figo.gao@foxmail.com China 6992 58
Hubei Jusheng Technology Co.,Ltd. 		18871490254 linda@hubeijusheng.com CHINA 28180 58
Jinan Finer Chemical Co., Ltd 		+86-531-88989536 +86-15508631887 sales@finerchem.com China 2967 58
Accela ChemBio Inc. 		(+1)-858-699-3322 info@accelachem.com United States 19965 58
Xi'an Kono chem co., Ltd., 		029-86107037 13289246953 info@konochemical.com China 2995 58
Supplier Advantage
Henan Bao Enluo International TradeCo.，LTD 		58
Henan Tianfu Chemical Co.,Ltd. 		55
Shanghai Zheyan Biotech Co., Ltd. 		58
career henan chemical co 		58
SHANDONG ZHI SHANG CHEMICAL CO.LTD 		58
Jinan Carbotang Biotech Co.,Ltd. 		58
Hubei Jusheng Technology Co.,Ltd. 		58
Jinan Finer Chemical Co., Ltd 		58
Accela ChemBio Inc. 		58
Xi'an Kono chem co., Ltd., 		58

Related articles

  • What is 2-Hydroxy-1,4-naphoquinone?
  • 2-Hydroxy-1,4-naphthoquinone (HNQ, C10H6O3, CAS registry No. 83-72-7) is also called Lawsone, which is a white cubic crystal.
  • Feb 14，2020

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

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2-Hydroxy-1,4-naphoquinone pictures 2024-04-26 2-Hydroxy-1,4-naphoquinone
83-72-7
 US $5.00 / kg 1kg ≥98% 200mt/year Jinan Finer Chemical Co., Ltd
2-Hydroxy-1,4-naphoquinone pictures 2024-04-26 2-Hydroxy-1,4-naphoquinone
83-72-7
 US $450.00-400.00 / kg 100kg 99.99% 100Tons Hebei Dangtong Import and export Co LTD
2-Hydroxy-1,4-naphoquinone pictures 2023-09-14 2-Hydroxy-1,4-naphoquinone
83-72-7
 US $100.00 / bag 1bag 99 5000 Hebei Fengqiang Trading Co., LTD

2-Hydroxy-1,4-naphoquinone Spectrum

2-Hydroxy-1,4-naphoquinone(83-72-7)MS2-Hydroxy-1,4-naphoquinone(83-72-7)1HNMR2-Hydroxy-1,4-naphoquinone(83-72-7)13CNMR2-Hydroxy-1,4-naphoquinone(83-72-7)IR12-Hydroxy-1,4-naphoquinone(83-72-7)IR2

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1,4-Naphthalenedione,2-hydroxy- 1,4-Naphthoquinone, 2-hydroxy- 2-Hydroxy-1,4-naphthalenedione 2-hydroxy-4-naphthalenedione 2-hydroxy-4-naphthoquinone Lawsone, Natural Orange 6 1,4-Dihydro-1,4-dioxo-2-hydroxynaphthalene Tetrabromozirconium 2-Hydroxy-p-naphthoquinone, 99%, pure 2-HYDROXY-P-NAPHTHOQUINONE, 94%, PURE 2-HYDROXY-1,4-NAPHTHOQUINONE, TECH. 2-Hydroxy-1,4-naphthoquinone ,98% [ pure] 2-Hydroxy-p-naphthoquinone, pure, 99% 100GR 2-Hydroxy-p-naphthoquinone, pure, 99% 25GR 2-Hydroxy-1,4- 2-HYDROXY-P-NAPHTHOQUINONE 2-Hydroxy-1,4-naphoquinone 2-HYDROXY-1,4-NAPHTHAQUINONE C.I. 75480~Lawsone lawsone (2-hydroxy-1,4-naphthoquinone) 2-HYDROXY-1,4-NAPHTHOQUINONE (LAWSONE). 2-HYDROXY-1 4-NAPHTHOQUINONE 97% 2-Hydroxy-1,4-Naphthquinone 2-Hydroxy-1,4-naphthoquinone, 98+% 2-Hydroxy-p-naphthoquinone, pure, 94% LAWSONE(P) 4-Naphthalenedione,2-hydroxy-1 C.I. Natural Orange 6 c.i.naturalorange6 Flower Of Paradise flowerofparadise Hana Hydroxynaphthoquinone, 2-hydroxy- Mehendi Mendi NATURAL ORANGE 6 CI 75480 JAROCOL LAWSONE 2-Hydroxy-1,4-naphthoquinone> Hennotannic acid 2-Hydroxy-1,4-naphthochinon 2-Hydxoxy-p-naphthoquinone 83-72-7 2-Hydroxy-1,4-naphoquinone 4-hydroxynaphthalene-1,2-dione 2-Hydroxynaphthoquinone 2-Hydroxynaphthalene-1,4-dione 3-Hydroxy-1,4-naphthoquinone 2-HYDROXY-1,4-NAPHTHOQUINONE Henna Lawson LAWSONE Phytonadione Impurity 75 2-hydroxy-1,4-napthoquinone Thiooxacillin 2 - hydroxynaphthalene - 1,4 - dione ( Lawsone ) 83-72-7 Pyridines Inhibitors