ANTHRALIN Chemical Properties

Melting point:

178-181 °C (lit.)

Boiling point:

464.1±45.0 °C(Predicted)

Density 

1.419±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Practically insoluble in water, soluble in methylene chloride, sparingly soluble in acetone, slightly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides.

form 

Solid

pka

7.16±0.20(Predicted)

color 

Yellow to Orange to Dark Yellow

Water Solubility 

Insoluble in water. Soluble in acetic acid, chloroform (20 mg/mL), acetone, benzene, solutions of alkali hydroxides, fixed oil. Slightly soluble in 95% ethanol, alcohol, ether, and glacial acetic acid.

Merck 

14,684

BRN 

2054360

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

NUZWLKWWNNJHPT-UHFFFAOYSA-N

CAS DataBase Reference

1143-38-0(CAS DataBase Reference)

IARC

3 (Vol. 13; Sup 7) 1987

EPA Substance Registry System

Dithranol (1143-38-0)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-45

Safety Statements 

26-53-45

WGK Germany 

3

RTECS 

CB8927000

HS Code 

29144000

MSDS

• Language:English Provider:SigmaAldrich

ANTHRALIN Usage And Synthesis

Description

Anthralin is an anthrone inhibitor of keratinocyte proliferation and a modulator of differentiation. It increases apoptosis and inhibits proliferation of normal human keratinocytes (NHKs) when used at a concentration of 2.5 μM. It also decreases the mitochondrial membrane potential, increases cytochrome c release, and induces perinuclear mitochondrial clustering in NHKs when used at a concentration of 5 μM. Anthralin (0.25 μM) decreases the expression of β-defensin-2 and S100 calcium-binding protein A9 (S100A9) and increases the expression of IL-6 and IL-8 in IL-17A- and IL-22-stimulated NHKs. It also inhibits leukotriene B₄ (LTB₄; ) production, stimulated by the calcium ionophore A23187 , from human neutrophils (IC₅₀ = 7 μM). Topical anthralin (0.1%) induces hair regrowth in a Dundee experimental bald rat (DEBR) model of alopecia areata.

Chemical Properties

Yellow Crystalline Solid

Uses

Antipsoriatic

Indications

Anthralin (Anthra-Derm) is a potent reducing agent whose mechanism of action is unknown. It is approved for the treatment of psoriasis and also may be helpful in alopecia areata. The major toxicities are discoloration of skin, hair, and nails and irritant dermatitis.

Definition

ChEBI: An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.

brand name

Anthra-Derm (Dermik); DrithoCreme (Dermik); Drithoscalp (Dermik); Lasan (Stiefel).

General Description

Lemon yellow leaflets or plates or an orange powder. Melting point 176-181°C. No odor or taste. Insoluble in water. Moderately toxic by ingestion, inhalation and skin absorption. Used as a treatment for psoriasis.

Air & Water Reactions

Unstable in air when in alkaline solution. Insoluble in water.

Reactivity Profile

ANTHRALIN reacts as a weak acid. Soluble in aqueous bases. May react with strong oxidizing agents. May be sensitive to light and moisture .

Hazard

Very irritating. Do not use on scalp or near eyes.

Fire Hazard

Flash point data are not available for ANTHRALIN; however, ANTHRALIN is probably combustible.

Side effects

Anthralin's side effects include pruritus, erythema, scaling, folliculitis, and lymphadenopathy. Staining of skin and clothes can also be an issue.

ANTHRALIN(1143-38-0)Related Product Information

• FRANGULIN B
• Rhein
• 1,8-Dihydroxy-4,5-dinitroanthraquinone
• 1,2,5,8-TETRAHYDROXYANTHRAQUINONE
• Emodin-3-methyl ether
• Aloe emodin
• FRANGULIN A
• 1,8-Dihydroxyanthraquinone
• Emodin
• Chrysophanic acid
• ANTHRALIN
• Anthrone
• Anthracene
• SENNIDINE A
• 1,8-diphenoxyanthraquinone
• CYNODONTIN
• CATENARIN
• 1,8-dimethoxyanthraquinone