Lawsone

Last updated
Lawsone [1] [2]
HNQ.svg
Lawsone-3D-balls.png
Names
Preferred IUPAC name
2-Hydroxynaphthalene-1,4-dione
Other names
2-Hydroxy-1,4-naphthoquinone
Hennotannic acid
Natural Orange 6
C.I. 75480
Identifiers
3D model (JSmol)
1565260
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.361 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-496-3
4828
KEGG
PubChem CID
UNII
  • InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H X mark.svgN
    Key: CSFWPUWCSPOLJW-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H
    Key: CSFWPUWCSPOLJW-UHFFFAOYAK
  • O=C(C(O)=C1)C2=C(C=CC=C2)C1=O
Properties
C10H6O3
Molar mass 174.15 g/mol
AppearanceYellow prisms
Melting point 195 to 196 °C (383 to 385 °F; 468 to 469 K) (decomposition)
almost insoluble [3]
Hazards [4]
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Warning
H315, H319, H335
P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Lethal dose or concentration (LD, LC):
100 mg/kg
Related compounds
Juglone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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:

  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. [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]

The naphthoquinones lawsone methyl ether and methylene-3,3'-bilawsone are some of the active compounds in Impatiens balsamina leaves. [13] Juglone is a structural isomer used as a brown dye.

Related Research Articles

<span class="mw-page-title-main">Fluorescence</span> Emission of light by a substance that has absorbed light

Fluorescence is the emission of light by a substance that has absorbed light or other electromagnetic radiation. It is a form of luminescence. In most cases, the emitted light has a longer wavelength, and therefore a lower photon energy, than the absorbed radiation. A perceptible example of fluorescence occurs when the absorbed radiation is in the ultraviolet region of the electromagnetic spectrum, while the emitted light is in the visible region; this gives the fluorescent substance a distinct color that can only be seen when the substance has been exposed to UV light. Fluorescent materials cease to glow nearly immediately when the radiation source stops, unlike phosphorescent materials, which continue to emit light for some time after.

Nitric acid is the inorganic compound with the formula HNO3. It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into oxides of nitrogen. Most commercially available nitric acid has a concentration of 68% in water. When the solution contains more than 86% HNO3, it is referred to as fuming nitric acid. Depending on the amount of nitrogen dioxide present, fuming nitric acid is further characterized as red fuming nitric acid at concentrations above 86%, or white fuming nitric acid at concentrations above 95%.

The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds, resulting in "a fully conjugated cyclic dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone". Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.

<span class="mw-page-title-main">Hair coloring</span> Practice of changing the hair color

Hair coloring, or hair dyeing, is the practice of changing the hair color. The main reasons for this are cosmetic: to cover gray or white hair, to alter hair to create a specific look, to change a color to suit preference or to restore the original hair color after it has been discolored by hairdressing processes or sun bleaching.

<i>Impatiens</i> Genus of flowering plants

Impatiens is a genus of more than 1,000 species of flowering plants, widely distributed throughout the Northern Hemisphere and the tropics. Together with the genus Hydrocera, Impatiens make up the family Balsaminaceae.

<span class="mw-page-title-main">Juglone</span> Chemical produced by walnut trees

Juglone, also called 5-hydroxy-1,4-naphthalenedione (IUPAC) is an organic compound with the molecular formula C10H6O3. In the food industry, juglone is also known as C.I. Natural Brown 7 and C.I. 75500. It is insoluble in benzene but soluble in dioxane, from which it crystallizes as yellow needles. It is an isomer of lawsone, which is the active dye compound in the henna leaf.

Upconverting nanoparticles (UCNPs) are nanoscale particles that exhibit photon upconversion. In photon upconversion, two or more incident photons of relatively low energy are absorbed and converted into one emitted photon with higher energy. Generally, absorption occurs in the infrared, while emission occurs in the visible or ultraviolet regions of the electromagnetic spectrum. UCNPs are usually composed of rare-earth based lanthanide- or actinide-doped transition metals and are of particular interest for their applications in in vivo bio-imaging, bio-sensing, and nanomedicine because of their highly efficient cellular uptake and high optical penetrating power with little background noise in the deep tissue level. They also have potential applications in photovoltaics and security, such as infrared detection of hazardous materials.

References

  1. ↑ Merck Index, 12th Edition, 5406.
  2. ↑ MSDS Archived 2005-12-17 at the Wayback Machine at Physical & Theoretical Chemistry Laboratory, University of Oxford
  3. ↑ http://msds.chem.ox.ac.uk/HY/2-hydroxy-1,4-naphthaquinone.html [ dead link ]
  4. ↑ "2-Hydroxy-1,4-naphthoquinone". pubchem.ncbi.nlm.nih.gov.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ Jordão, A.; Vargas, M.; Pinto, A.; da Silva, F.; Ferreira, V. Lawsone in organic synthesis. RSC Adv. 2015, 5, 67909-67943.
  8. ↑ Shuang, S.; Lei, Q.; Ting, Y.; Qifu, Y. Method for preparing lawsone from lawsonia inermis China Patent CN 103848732A, June 11, 2014.
  9. ↑ 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.
  10. 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
  11. ↑ 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.
  12. ↑ 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.
  13. ↑ 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.