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Lawsone

Cat No.:V23814 Purity: ≥98%
Lawsone is a naphthoquinone dye extracted from the leaves of Lawsonia inermis and has antibacterial and anti-oxidant effect.
Lawsone
Lawsone Chemical Structure CAS No.: 83-72-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
Other Sizes
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Product Description
Lawsone is a naphthoquinone dye extracted from the leaves of Lawsonia inermis and has antibacterial and anti-oxidant effect.
Lawsone, also known as hennotannic acid, is a natural red-orange dye derived from the leaves of the henna plant (Lawsonia inermis). It has a molecular weight of 174.15 g/mol and a molecular formula of C₁₀H₆O₃. Lawsone is the active ingredient in henna, responsible for its staining properties. It has been used for centuries as a cosmetic dye for skin, hair, and nails. Beyond its use as a dye, Lawsone has demonstrated a range of biological activities, including antibacterial, antifungal, antioxidant, anti-inflammatory, and anticancer properties. It is also used as a precursor for the synthesis of other compounds.
Biological Activity I Assay Protocols (From Reference)
Targets
Lawsone does not have a single defined molecular target. Its mechanism of action as a dye involves its ability to bind to keratin proteins in the skin and hair, forming a stable, dark-colored complex. Its biological activities are attributed to its ability to interact with various cellular targets. For example, its antimicrobial activity may be due to its ability to inhibit bacterial enzymes or disrupt cell membranes. Its antioxidant activity is related to its ability to scavenge free radicals. Its anticancer activity may involve the induction of apoptosis and inhibition of cell proliferation.
ln Vitro
In vitro, Lawsone has demonstrated antibacterial, antifungal, antioxidant, anti-inflammatory, and anticancer activities. It inhibits the growth of various bacterial and fungal strains. It scavenges free radicals in antioxidant assays. It inhibits the proliferation of cancer cell lines. Detailed IC₅₀ values for these activities are not extensively provided in the referenced sources.
ln Vivo
Detailed in vivo activity data for Lawsone are not extensively provided in the referenced sources. However, its long history of use as a cosmetic dye attests to its safety for topical application. Its antibacterial and antifungal properties suggest potential for in vivo efficacy in treating skin infections. Its anticancer activity could be studied in tumor models.
Enzyme Assay
Non-cell-based assays for Lawsone include measuring its antioxidant capacity using DPPH, ABTS, or FRAP assays. Its antibacterial and antifungal activities are assessed using standard MIC (minimum inhibitory concentration) assays.
Cell Assay
Cellular assays for Lawsone are performed using various cell lines. For anticancer studies, cancer cells are treated with the compound, and cell viability, apoptosis, and cell cycle progression are assessed. For anti-inflammatory studies, immune cells are treated with the compound, and the production of inflammatory mediators is measured.
Animal Protocol
In vivo animal models for Lawsone would include models of bacterial or fungal infection to assess its antimicrobial activity, and xenograft models to assess its anticancer activity. The compound would be administered topically or systemically.
ADME/Pharmacokinetics
Lawsone has a molecular weight of 174.15 g/mol and a molecular formula of C₁₀H₆O₃. Its CAS number is 83-72-7. The compound is a red-orange crystalline powder. Purity is typically ≥98%. It is soluble in organic solvents. Storage conditions: -20°C, protected from light. The compound is supplied for research use only.
Toxicity/Toxicokinetics
Lawsone is considered safe for topical application at the concentrations used in henna. However, it can cause allergic reactions in some individuals. The compound is intended for research use only and is not for human consumption. Standard laboratory safety precautions should be followed.
References

[1]. A fungitoxic principle from the leaves of lawsonia inermis lam. Experientia. 1978 Jan 15;34(1):51-2.

[2]. Haemolytic activity and nephrotoxicity of 2-hydroxy-1,4-naphthoquinone in rats. J Appl Toxicol. 1991 Apr;11(2):85-90.

[3]. Cytotoxicity of lawsone and cytoprotective activity of antioxidants in catalase mutant Escherichia coli. Toxicology. 2007 Jun 3;235(1-2):103-11.

[4]. Lawsone suppresses azoxymethane mediated colon cancer in rats and reduces proliferation of DLD-1 cells via NF-κB pathway. Biomed Pharmacother. 2017 May;89:152-161.

[5]. Lawsone inhibits cell growth and improves the efficacy of cisplatin in SKOV-3 ovarian cancer cell lines. African Journal of Traditional, Complementary and Alternative Medicines, 2017, 14(5): 8-17.

Additional Infomation
2-Hydroxy-1,4-naphthoquinone is a yellow prismatic or yellow powder. (NTP, 1992)
Hennaquinone is a 1,4-naphthoquinone with a hydroxyl group at the C-2 position. It is extracted from the leaves of henna (Lawsonia inermis). It has protective and antifungal properties. It is a tautomer of naphthyl-1,2,4-trione.
2-Hydroxy-1,4-naphthoquinone has also been reported in impatiens (Impatiens glandulifera), impatiens parviflora, and other organisms with relevant data.
Lawsone is also known as hennotannic acid. It is the active ingredient in henna, responsible for its dyeing properties. It has antibacterial, antifungal, antioxidant, anti-inflammatory, and anticancer activities. Its CAS number is 83-72-7.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H6O3
Molecular Weight
174.1528
Exact Mass
174.031
CAS #
83-72-7
Related CAS #
Lawsone-d4
PubChem CID
6755
Appearance
Light yellow to yellow solid powder
Density
1.5±0.1 g/cm3
Boiling Point
339.9±42.0 °C at 760 mmHg
Melting Point
192-195 °C (dec.)(lit.)
Flash Point
173.6±24.4 °C
Vapour Pressure
0.0±0.8 mmHg at 25°C
Index of Refraction
1.681
LogP
1.55
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
13
Complexity
291
Defined Atom Stereocenter Count
0
InChi Key
WVCHIGAIXREVNS-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,11H
Chemical Name
4-hydroxynaphthalene-1,2-dione
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~574.22 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.36 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (14.36 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.7422 mL 28.7109 mL 57.4218 mL
5 mM 1.1484 mL 5.7422 mL 11.4844 mL
10 mM 0.5742 mL 2.8711 mL 5.7422 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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