Anthralin

Specifications

Purity

≥98% (HPLC)

Identity

1H-NMR

Appearance

Faint yellow to yellow powder

Properties

Solvents

acetone

Handling Advice

Protect from light and moisture.

Use / Stability

Stable for at least 2 years after receipt when stored at -20°C.

Long Term Storage

-20°C

Short Term Storage

+4°C

Shipping

AMBIENT

Transportation

Not dangerous goods

Signal word

Warning

GHS Symbol

GHS07

Precautionary statements

P261-P305 + P351 + P338

Hazard statements

H315-H319-H335

Description

Anthralin is a leukotriene biosynthesis inhibitor. It inhibits LTB4 omega-oxidation and disrupts mitochondria function. Anthralin is used in the treatment of psoriasis, as a fungicide, in the treatment of ringworm infections and in chronic dermatoses. It accumulates in mitochondria where it interferes with the supply of energy to the cell, probably by the oxidation of dithranol releasing free radicals. This impedes DNA replication and so slows the excessive cell division that occurs in psoriatic plaques. Numerous studies have demonstrated anti-proliferative and anti-inflammatory effects of anthralin on psoriatic and normal skin. It is also used as matrix substance for MALDI-MS (matrix-assisted laser desorption ionization MS).

InChi

InChI=1S/C14H10O3/c15-10-5-1-3-8-7-9-4-2-6-11(16)13(9)14(17)12(8)10/h1-6,15-16H,7H2

References

(1) R.E. Ashton, et al.: J. Am. Acad. Dermatol. 9, 173 (1983) , (2) J.M. Schröder: J. Invest. Dermatol. 87, 624 (1986) , (3) C.E. Orfanos, et al.: Drugs 34, 459 (1987) (Review) , (4) L. Kemeny, et al.: Skin Pharmacol. 3, 1 (1990) , (5) K. Müller: Biochem. Pharmacol. 53, 1215 (1997) (Review) , (6) K. Pavithran: Indian J. Dermatol. Venereol. Leprol. 67, 104 (2001) , (7) C.H. Le, et al.: Anal. Chem. 84, 8391 (2012) , (8) C. Ronpirin & T. Tencomnao: Genet. Mol. Res. 11, 412 (2012) , (9) S.E. George, et al.: J. Pharm. Pharmacol. 65, 552 (2013)

InChi Key

NUZWLKWWNNJHPT-UHFFFAOYSA-N

Smiles

OC1=CC=CC2=C1C(=O)C1=C(O)C=CC=C1C2