Lawsone
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| Names | |
|---|---|
| IUPAC name
2-Hydroxy-1,4-naphthoquinone | |
| Other names
Hennotannic acid Natural Orange 6 C.I. 75480 | |
| Identifiers | |
83-72-7  | |
| ChEBI | CHEBI:44401  |
| ChEMBL | ChEMBL240963 |
| ChemSpider | 10430995 |
| EC Number | 201-496-3 |
| Jmol interactive 3D | Image |
| KEGG | C10368 |
| PubChem | 6755 |
| UNII | TLH4A6LV1W |
| |
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| Properties | |
| C10H6O3 | |
| Molar mass | 174.15 g/mol |
| Appearance | Yellow prisms |
| Melting point | 195 to 196 °C (383 to 385 °F; 468 to 469 K) (decomposition) |
| almost insoluble [3] | |
| Hazards | |
| R-phrases | R36 R37 R38 |
| S-phrases | S26 S36 S37 S39 |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose) |
100 mg/kg |
| Related compounds | |
| Related naphthoquinones |
Juglone |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
Lawsone (2-hydroxy-1,4-naphthoquinone), also known as hennotannic acid, is a red-orange dye present in the leaves of the henna plant (Lawsonia inermis) as well as in the flower of water hyacinth (Eichhornia crassipes).[4] Humans have used henna extracts containing lawsone as hair and skin dyes for more than 5000 years. Lawsone reacts chemically with the protein known as keratin in skin and hair, in a process known as Michael addition, resulting in a strong permanent stain that lasts until the skin or hair is shed. Lawsone strongly absorbs UV light, and aqueous extracts can be effective sunless tanning and sunscreens. Chemically, lawsone is similar to juglone, which is found in walnuts.
Lawone isolation from Lawsonia Inermis can be difficult due to its easily biodegradeable nature. Isolation involves four steps: 1) extraction with an extraction solution, usually NaOH, 2) column filtration using a macroporous adsorption resin, 3) a rinse with ethanol to remove impurities, and finally 4) freeze- the product to isolate the lawsone powder, usually a yellow colored dust. [5]
Lawsone is hypothesized to undergo a reaction similar to Strecker synthesis in reactions with amino acids. [6] Recent research has been conducted on lawsone's potential applications in the forensic science field. Since lawsone shows many similarities with ninhydrin, the current reagent for latent fingerprint development, studies have been conducted to see if lawsone can be used in this field. As of now the research is inconclusive, but optimistic. Lawsone non-specifically targets primary amino acids, and displays photoluminescence with forensic light sources.[6]
Related compounds
The naphthoquinones lawsone methyl ether and methylene-3,3'-bilawsone are some of the active compounds in Impatiens balsamina leaves.[7]
References
- ↑ Merck Index, 12th Edition, 5406.
- ↑ MSDS at Physical & Theoretical Chemistry Laboratory, University of Oxford
- ↑ http://msds.chem.ox.ac.uk/HY/2-hydroxy-1,4-naphthaquinone.html
- ↑ Dweck, A. C. (2002). "Natural ingredients for colouring and styling". International Journal of Cosmetic Science 24 (5): 287–302. doi:10.1046/j.1467-2494.2002.00148.x. PMID 18498522.
- ↑ Shuang, S.; Lei, Q.; Ting, Y.; Qifu, Y. Method for preparing lawsone from lawsonia inermis China Patent CN 103848732 A, June 11, 2014.
- 1 2 Jelly, R.; Lewis, S. W.; Lennard, C.; Lim, K. F.; Almog, J. Lawsone: a novel reagent for the detection of latent fingermarks on paper surfaces. Chem.Commun. 2008, 3513-3515
- ↑ Sakunphueak, A.; Panichayupakaranant, P. (2010). "Simultaneous determination of three naphthoquinones in the leaves of Impatiens balsamina L. by reversed‐phase high‐performance liquid chromatography". Phytochemical Analysis 21 (5): 444–50. doi:10.1002/pca.1216. PMID 20931623.