Basic information
- CAS
83-72-7- Standard SMILES
O=C1C=C(O)c2ccccc2C1=O- InChIKey
CSFWPUWCSPOLJW-UHFFFAOYSA-N- Molecular formula
- C10H6O3
- Average molar mass
- 174.15 g/mol
- Monoisotopic mass
- 174.03169405
Overview
Lawsone is 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis. It has a role as an antifungal agent and a protective agent. It is a tautomer of a naphthalene-1,2,4-trione.
Names & identifiers
- Preferred name
- 2-Hydroxy-1,4-naphthoquinone
- IUPAC
- 4-hydroxynaphthalene-1,2-dione
- English name
- 2-Hydroxy-1,4-naphoquinone
- Molecular formula
- C10H6O3
- Molecular weight
- 174.15
Names & synonyms
Lawsone83-72-72-Hydroxy-1,4-naphthoquinone2-hydroxynaphthalene-1,4-dione2-Hydroxy-1,4-naphoquinone2-HydroxynaphthoquinoneHennaMehendiHANALawsonNatural Orange 6Mendi
Show more names
3-Hydroxy-1,4-naphthoquinone
1,4-Naphthalenedione, 2-hydroxy-4-hydroxynaphthalene-1,2-dione2-Hydroxy-1,4-naphthalenedioneC.I. Natural Orange 61,4-Naphthoquinone, 2-hydroxy-2-Hydroxy-p-naphthoquinoneC.I. 75480NSC 8625
Database identifiers
- CAS
83-72-7- PubChem CID
- 6755
- DTXSID
DTXSID2025428- ChEMBL
CHEMBL240963- ChEBI
CHEBI:44401- UNII
- TLH4A6LV1W
- Nikkaji
- J2.169.330H、J4.642F
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 291
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsHair dyeing; Skin conditioning; Bulking
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
LogP1.38
Food AdditivesCosmetics -> FDA Regulatory Status of Color Additives
Physicochemical properties
- Melting point
- 192 · 192-195 °C (dec.)(lit.)
- Boiling point
- 265.11 °C · 265.11°C (rough estimate)
- Density
- 1.2346 · 1.2346 (rough estimate)
- refractive index
- 1.5036 · 1.5036 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
- pka
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- QL8200000
- hs_code
- 29146990
- risk_code
- 36/37/38-68-36-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 26-37/39-36/37/39-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Use Classification
Environmental transformation -> Pesticide transformation products (metabolite, successor)
Cosmetics -> Hair dyeing; Skin conditioning; Bulking
Applications
DescriptionLawsone [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.
HistoryLawsone (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.
Uses2-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.
Usesantifungal, sunscreen, antibacterial, antineoplastic
UsesAn antimicrobial antioxidant dye isolated from Henna.
General DescriptionYellow prisms or yellow powder.
Related reactions
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Compound notes
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