ChemicalBook CAS DataBase List 83-72-7

83-72-7

Name	2-Hydroxy-1,4-naphoquinone
CAS	83-72-7
EINECS(EC#)	201-496-3
Molecular Formula	C10H6O3
MDL Number	MFCD00001678
Molecular Weight	174.15
MOL File	83-72-7.mol

Synonyms

2-Hydroxy-1,4-naphoquinone 2-HYDROXY-1,4-NAPHTHAQUINONE 2-HYDROXY-1,4-NAPHTHOQUINONE 2-HYDROXY-P-NAPHTHOQUINONE CI 75480 JAROCOL LAWSONE LAWSONE NATURAL ORANGE 6 1,4-Naphthalenedione,2-hydroxy- 1,4-Naphthoquinone, 2-hydroxy- 2-Hydroxy-1,4-naphthalenedione 2-hydroxy-4-naphthalenedione 2-hydroxy-4-naphthoquinone 2-Hydroxynaphthoquinone 4-Naphthalenedione,2-hydroxy-1 C.I. Natural Orange 6 c.i.naturalorange6 Flower Of Paradise flowerofparadise Hana

Chemical Properties

Definition	A coloring principle obtained from dried leaves of certain tropical plants (North Africa, India).
Appearance	Yellow crystal powder
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)
Colour Index	75480
form	Crystalline Powder
pka	4.31±0.10(Predicted)
color	Yellow
Stability:	Stable. Combustible. Incompatible with strong oxidizing agents.
Water Solubility	2 g/L (20 ºC)
λmax	452 nm
Merck	14,5393
BRN	1565260
Cosmetics Ingredients Functions	BULKING HAIR DYEING SKIN CONDITIONING
InChI	1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H
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 less more
InChIKey	CSFWPUWCSPOLJW-UHFFFAOYSA-N
SMILES	OC1=CC(=O)c2ccccc2C1=O
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	83-72-7(EPA Substance)

Safety Data

Symbol(GHS)	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	R36/37/38:Irritating to eyes, respiratory system and skin . R68:Possible risk of irreversible effects. R36:Irritating to the eyes. R22:Harmful if swallowed. less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S37/39:Wear suitable gloves and eye/face protection . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S36:Wear suitable protective clothing . less more
WGK Germany	3
RTECS	QL8200000
TSCA	Yes
HS Code	29146990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Raw materials And Preparation Products

Hazard Information

Chemical Properties

Yellow crystal powder

Uses

An antimicrobial antioxidant dye isolated from Henna.

Uses

antifungal, sunscreen, antibacterial, antineoplastic

General Description

Yellow prisms or yellow powder.

Reactivity Profile

Phenols, such as 2-HYDROXY-1,4-NAPHTHOQUINONE(83-72-7), 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.

Air & Water Reactions

Insoluble in water.

Health Hazard

ACUTE/CHRONIC HAZARDS: This compound may be absorbed through the skin and can cause skin irritation.

Fire Hazard

Flash point data for this chemical are not available but 2-HYDROXY-1,4-NAPHTHOQUINONE is probably combustible.

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/jo00239a023
Tetrahedron Letters, 25, p. 533, 1984 DOI: 10.1016/S0040-4039(00)99930-1

storage

Store at -20°C

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.]

Material Safety Data Sheet(MSDS)

Questions And Answer

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.
;

Spectrum Detail

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83-72-7

Chemical Properties

Safety Data

Raw materials And Preparation Products

Raw materials

Preparation Products

Hazard Information

Chemical Properties

Uses

Uses

General Description

Reactivity Profile

Air & Water Reactions

Health Hazard

Fire Hazard

History

Synthesis Reference(s)

storage

Purification Methods

Material Safety Data Sheet(MSDS)

Questions And Answer

Description

Chemical Propterties

Application

Biological Toxicity

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

Related Products