Lawsone

Lawsone[1][2]

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

CAS Number

* 83-72-7 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 1565260
ChEBI |

* CHEBI:44401 Y

ChEMBL |

* ChEMBL240963 Y

ChemSpider |

* 10430995 Y

DrugBank |

* DB04744

EC Number |

* 201-496-3

Gmelin Reference

| 4828
KEGG |

* C10368 Y

PubChem CID

* 6755

UNII |

* TLH4A6LV1W Y

InChI

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

Key: CSFWPUWCSPOLJW-UHFFFAOYSA-N N

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

Key: CSFWPUWCSPOLJW-UHFFFAOYAK

SMILES

* O=C(C(O)=C1)C2=C(C=CC=C2)C1=O

Properties

Chemical formula

| 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)

Solubility in water

| almost insoluble [3]
Hazards[4]
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H315, H319, H335

GHS precautionary statements

| P201, P202, P261, P264, P270, P271, P280, P281, P301+312, P302+352, P304+340, P305+351+338, P308+313, P312, P330, P332+313, P337+313, P362, P403+233, P405, P501
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).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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]

## Related compounds

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.

## References

1. ↑ Merck Index, 12th Edition, 5406.
2. ↑ MSDS at Physical & Theoretical Chemistry Laboratory, University of Oxford
3. ↑ http://msds.chem.ox.ac.uk/HY/2-hydroxy-1,4-naphthaquinone.html [|permanent dead link|dead link}}]
4. ↑ "2-Hydroxy-1,4-naphthoquinone" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/6755#section=Safety-and-Hazards.
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. 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. ↑ 10.0 10.1 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.

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Lawsone&oldid=485986"
*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P201]: Obtain special instructions before use
*[P202]: Do not handle until all safety precautions have been read and understood
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P281]: Use personal protective equipment as required
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P308+313]: IF exposed or concerned: Get medical advice/attention
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P330]: Rinse mouth
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …