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Chemical compound
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), for which it is named, as well as in the common walnut (Juglans regia)[5] and water hyacinth (Pontederia crassipes).[6] Humans have used henna extracts containing lawsone as hair and skin dyes for more than 5,000 years. Lawsone reacts chemically with the protein keratin in skin and hair via a Michael addition reaction, resulting in a strong permanent stain that lasts until the skin or hair is shed. Darker colored staining is due to more lawsone–keratin interactions occurring, which evidently break down as the concentration of lawsone decreases and the tattoo fades.[7] Lawsone strongly absorbs UV light, and aqueous extracts can be effective sunless tanning agents and sunscreens. Lawsone is a 1,4-naphthoquinone derivative, an analog of hydroxyquinone containing one additional ring.
Lawsone isolation from Lawsonia inermis can be difficult due to its easily biodegradable nature. Isolation involves four steps:
extraction with an extraction solution, usually NaOH
column filtration using a macroporous adsorption resin
a rinse with ethanol to remove impurities, and finally
freeze the product to isolate the lawsone powder, usually a yellow colored dust.[8]
During the rinse, the lawsone will be the bottom as it has such a high density and the chlorophyll molecules will all be on the top of the mixture.[9]
Lawsone is hypothesized to undergo a reaction similar to Strecker synthesis in reactions with amino acids.[10] 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.[10] It has a characteristic purple/brown coloration as opposed to the purple/blue associated with ninhydrin.[11]
Lawsone shows promise as a reagent for fingerprint detection because of its photoluminescence maximized at 640 nm, which is high enough that it avoids background interference common for ninhydrin.[12]
^Merck Index, 12th Edition, 5406.
^MSDS Archived 2005-12-17 at the Wayback Machine at Physical & Theoretical Chemistry Laboratory, University of Oxford
^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.
^Kurtyka, Renata; Pokora, Wojciech; Tukaj, Zbigniew; Karcz, Waldemar (2016). "Effects of juglone and lawsone on oxidative stress in maize coleoptile cells treated with IAA". AoB Plants. 8: plw073. doi:10.1093/aobpla/plw073. PMC 5199135. PMID 27760740.
^Jordão, A.; Vargas, M.; Pinto, A.; da Silva, F.; Ferreira, V. Lawsone in organic synthesis. RSC Adv. 2015, 5, 67909-67943.
^Shuang, S.; Lei, Q.; Ting, Y.; Qifu, Y. Method for preparing lawsone from lawsonia inermis China Patent CN 103848732A, June 11, 2014.
^Gallo, F.; Multari, G.; Giambenedetti, M.; Federici, E. Chemical fingerprinting of Lawsonia inermis L. using HPLC, HPTLC, and densitometry. Phytochem. Anal. 2008, 19, 550-559.
^ abJelly, 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
^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.
^Thomas, P.; Farrugia, K. An investigation into the enhancement of fingermarks in blood on paper with genipin and lawsone. Sci. Justice 2013, 53, 315-320.
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)...
chemical agent, lawsone, is bound within the plant. However, dried henna leaves will stain the skin if they are mashed into a paste. The lawsone will gradually...
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Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of both ubiquinone and lawsone. Atovaquone is a medication used to treat or prevent: For pneumocystis...
4-Naphthoquinone Alkannin Hexahydroxy-1,4-naphthalenedione Juglone Lapachol Lawsone Menatetrenone 2-Methoxy-1,4-naphthoquinone, a compound found in Impatiens...
by other atoms or radicals. Chloranil, a reagent in organic chemistry Lawsone, a dye present in the leaves of the henna plant Alizarin, a common red...
jewelweeds, including the garden jewelweed contain the naphthoquinone lawsone, a dye that is also found in henna (Lawsonia inermis) and is also the hair...
dioxane, from which it crystallizes as yellow needles. It is an isomer of lawsone, which is the active dye compound in the henna leaf. Juglone occurs naturally...
Impatiens capensis, the related cultivar I. balsamina and the component, lawsone in preventing post poison ivy exposure contact dermatitis". Journal of...
in nuclear fusion research Lawson Software, a company acquired by Infor Lawsone, a naphthoquinone dye from henna Jean de Lauson (1584–1666), Governor of...
skin contains higher levels of keratin there, which binds temporarily to lawsone, the colorant of henna. The men will also have a party, in which the groom's...
commonly used as a deposit-only{explain} hair color whose active component, lawsone, binds to keratin. It is therefore considered semi-permanent to permanent...
mass: 174.0317 u) may refer to: Juglone, or 5-hydroxy-1,4-naphthalenedione Lawsone, or 2-hydroxy-1,4-naphthoquinone This set index page lists chemical structure...
touching an Agreement between the Mayor and Commons of Newcastell and Edmunde Lawsone. Foundation of Berkhamstead School Act 1548 2 & 3 Edw. 6. c. 20 (Ruffhead:...
its symmetry there are only three isomers: 2-Hydroxy-1,4-naphthoquinone (lawsone), coloring principle of henna. 5-Hydroxy-1,4-naphthoquinone (juglone),...
(elder) Kenneth McKenzie (younger) Lauchland McIntosh Neill McMillon Patrick Lawsone Patrick Cokburne Robert Chisholm Robert Adamsone Robert Davidsone Robert...