Lawsone | CAS#83-72-7 |

MedKoo Cat#: 591861 | Name: Lawsone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lawsone, also known as Naphaquinon, is a molluscacide from leaves of Lawsonia inermis L. topical sunscreening agent; powdered leaves of Lawsonia inermis(Lythraceae) used as brown hair dye.

Chemical Structure

Lawsone

CAS#83-72-7

Theoretical Analysis

MedKoo Cat#: 591861

Name: Lawsone

CAS#: 83-72-7

Chemical Formula: C10H6O3

Exact Mass: 174.0317

Molecular Weight: 174.16

Elemental Analysis: C, 68.97; H, 3.47; O, 27.56

Price and Availability

Size	Price	Availability
5g	USD 250.00	2 Weeks
25g	USD 450.00	2 Weeks
100g	USD 750.00	2 Weeks

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Related CAS #

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Synonym

Lawsone; Naphaquinone;

IUPAC/Chemical Name

1,4-Naphthalenedione, 2-hydroxy-

InChi Key

CSFWPUWCSPOLJW-UHFFFAOYSA-N

InChi Code

InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H

SMILES Code

O=C1C(O)=CC(C2=C1C=CC=C2)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lawsone is a naphthoquinone dye isolated from leaves of Lawsonia inermis that shows antimicrobial and antioxidant activity.

In vitro activity:

Lawsone affected yeast growth in glycerol, indicating interference in the respiratory metabolism. By analysing the sensitivity of atg mutant strains and the localization of GFP-Atg8 fusion protein, it was concluded that lawsone primarily produces mitochondrial malfunctioning, leading to indirect oxidative stress. Reference: Mol Biol Rep. 2020 Feb;47(2):1173-1185. https://pubmed.ncbi.nlm.nih.gov/31811499/

In vivo activity:

In skin regeneration models, Lawsone interferes with physiological tissue regeneration and inhibits wound healing. Conversely, in a human acute dermatitis model, topical application of a Lawsone-containing cream ameliorates skin irritation. Reference: Sci Rep. 2019 Jul 26;9(1):10878. https://pubmed.ncbi.nlm.nih.gov/31350436/

	Solvent	mg/mL	mM
Solubility
	DMSO	67.0	384.71

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 174.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Xavier MR, Santos MMS, Queiroz MG, de Lima Silva MS, Goes AJS, De Morais MA Jr. Lawsone, a 2-hydroxy-1,4-naphthoquinone from Lawsonia inermis (henna), produces mitochondrial dysfunctions and triggers mitophagy in Saccharomyces cerevisiae. Mol Biol Rep. 2020 Feb;47(2):1173-1185. doi: 10.1007/s11033-019-05218-3. Epub 2019 Dec 6. PMID: 31811499. 2. Tripathi RD, Srivastava HS, Dixit SN. A fungitoxic principle from the leaves of lawsonia inermis lam. Experientia. 1978 Jan 15;34(1):51-2. doi: 10.1007/BF01921895. PMID: 620734. 3. Lozza L, Moura-Alves P, Domaszewska T, Lage Crespo C, Streata I, Kreuchwig A, Puyskens A, Bechtle M, Klemm M, Zedler U, Silviu Ungureanu B, Guhlich-Bornhof U, Koehler AB, Stäber M, Mollenkopf HJ, Hurwitz R, Furkert J, Krause G, Weiner J 3rd, Jacinto A, Mihai I, Leite-de-Moraes M, Siebenhaar F, Maurer M, Kaufmann SHE. The Henna pigment Lawsone activates the Aryl Hydrocarbon Receptor and impacts skin homeostasis. Sci Rep. 2019 Jul 26;9(1):10878. doi: 10.1038/s41598-019-47350-x. Erratum in: Sci Rep. 2020 May 20;10(1):8640. PMID: 31350436; PMCID: PMC6659674. 4. Wang SB, Tao Z, Li P. 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. doi: 10.1016/j.biopha.2017.01.169. Epub 2017 Feb 20. PMID: 28222396.

In vitro protocol:

In vivo protocol:

1. Lozza L, Moura-Alves P, Domaszewska T, Lage Crespo C, Streata I, Kreuchwig A, Puyskens A, Bechtle M, Klemm M, Zedler U, Silviu Ungureanu B, Guhlich-Bornhof U, Koehler AB, Stäber M, Mollenkopf HJ, Hurwitz R, Furkert J, Krause G, Weiner J 3rd, Jacinto A, Mihai I, Leite-de-Moraes M, Siebenhaar F, Maurer M, Kaufmann SHE. The Henna pigment Lawsone activates the Aryl Hydrocarbon Receptor and impacts skin homeostasis. Sci Rep. 2019 Jul 26;9(1):10878. doi: 10.1038/s41598-019-47350-x. Erratum in: Sci Rep. 2020 May 20;10(1):8640. PMID: 31350436; PMCID: PMC6659674. 2. Wang SB, Tao Z, Li P. 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. doi: 10.1016/j.biopha.2017.01.169. Epub 2017 Feb 20. PMID: 28222396.