1143-38-0 Usage
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
Dithranol, a potential anti-psoriasis medication, may be used to study its safety, efficacy, metabolism and pharmacological profile. Dithranol may be used to study is physicochemical properties, as a reference compound and to develop effective drug delivery vehicles. Dithranol may be used as a matrix for matrix assisted laser desorption/ionization imaging on a Fourier transform ion cyclotron resonance mass spectrometer.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 1143-38-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,4 and 3 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1143-38:
(6*1)+(5*1)+(4*4)+(3*3)+(2*3)+(1*8)=50
50 % 10 = 0
So 1143-38-0 is a valid CAS Registry Number.
InChI:InChI=1/C14H10O3/c15-10-5-1-3-8-7-9-4-2-6-11(16)13(9)14(17)12(8)10/h1-7,15-17H
1143-38-0Relevant articles and documents
Substitution of 1,8-dihydroxyanthron-9 in the meso-(10)-position. XI. On laxatives
Schultz,Schultze Mosgaue
, p. 313 - 320 (1965)
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Syntheses of anthraeenones. 1. Sodium dithionite reduction of peri-substituted anthracenediones
Prinz, Helge,Wiegrebe, Wolfgang,Mu?ller, Klaus
, p. 2853 - 2856 (1996)
The reaction of peri-substituted anthracenediones with sodium dithionite in dimethylformamide and water has been investigated. The system selectively reduces the carbonyl group flanked by the peri substituents of the anthracenediones to give the corresponding 4,5-disubstituted 9(10H)-anthracenones and thus provides a route to anthracenones which are otherwise difficult to obtain. Many functional groups can be tolerated, the reaction is compatible with the presence of peri alkoxy groups and unsaturated side chains of the starting anthracenediones, and the reduction does not go beyond the anthracenone stage. However, the formation of anthracenones depends on the nature of the peri substituents. No products were obtained from the 1,8-dimethyl-substituted anthracene-dione and the parent compound with no substituents.
Separation, identification, and quantitation of anthralin and its decomposition products
Elsabbagh,Whitworth,Schramm
, p. 388 - 390 (1979)
-
Straightforward Access to Anthrone Functionalized Benzylic Amines via Organocatalytic 1,2-Addition of Anthrones to Imines at Ambient Temperature
Das, Sumit,Bhowmik, Arup,Sarkar, Writhabrata,Mishra, Aniket,Deb, Indubhusan
, p. 4131 - 4142 (2021)
Activation of anthrone via benzylic deprotonation in the presence of triethylamine paves the way for the 1,2-addition reaction with imines to provide the desired functionalized anthrones in good to excellent yields under mild and operationally simple reaction conditions with a broad range of substrate scopes without using any external additives or toxic stoichiometric reagents.
