Lawsone

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Lawsone[1][2]
Skeletal formula
ball-and-stick model
Identifiers
CAS number 83-72-7 YesY
PubChem 6755
UNII TLH4A6LV1W N
ChEMBL CHEMBL240963 N
Jmol-3D images Image 1
Properties
Molecular formula C10H6O3
Molar mass 174.15
Appearance Yellow prisms
Melting point 195-196 °C (decomposition)
Solubility in water almost insoluble [3]
Hazards
R-phrases R36 R37 R38
S-phrases S26 S36 S37 S39
LD50 100 mg/kg
Related compounds
Related naphthoquinones Juglone
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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 jewelweed (Impatiens balsamina).[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.

Related compounds[edit]

The naphthoquinones lawsone methyl ether and methylene-3,3'-bilawsone are some of the active compounds in Impatiens balsamina leaves.[5]

References[edit]

  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
  4. ^ 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. 
  5. ^ 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. 

External links[edit]