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D2773

Sigma-Aldrich

Dithranol

≥90% (HPLC)

Synonym(s):

1,8,9-Anthracenetriol, 1,8-Dihydroxy-9(10H)-anthracenone, 1,8-Dihydroxyanthrone, Anthralin

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About This Item

Empirical Formula (Hill Notation):
C14H10O3
CAS Number:
1143-38-0
Molecular Weight:
226.23
Beilstein:
2054360
EC Number:
214-538-0
MDL number:
MFCD00053409
UNSPSC Code:
12352201
PubChem Substance ID:
24893712
NACRES:
NA.25

Assay

≥90% (HPLC)

form

solid

mp

178-181 °C (lit.)

solubility

chloroform: 20 mg/mL, clear to very slightly hazy, yellow

SMILES string

Oc1cccc2Cc3cccc(O)c3C(=O)c12

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

InChI key

NUZWLKWWNNJHPT-UHFFFAOYSA-N

Gene Information

mouse ... Alox12(11684)

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General description

Dithranol (1, 8 - dihydroxy-9-anthrone) is also called as anthralin. It is a vital topical antipsoriatic drugs. Dithranol, an athracene derivative, is a free radical generating mitochondrial poison that induces apoptosis in keratinocytes.

Application

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.

Other Notes

To gain a comprehensive understanding of our extensive range of Polysaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alison McGill et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 19(8), 1012-1014 (2005-04-02)
Anthralin is a potent topical drug, inducing clearance of psoriatic plaques. Anthralin disrupts mitochondrial function and structure, but its mechanism of action remains undefined. This study aimed to determine whether anthralin induced keratinocyte apoptosis as well as to investigate molecular
Wing Man Lau et al.
Pharmaceutics, 5(2), 232-245 (2013-12-05)
Psoriasis is a common, chronic and relapsing inflammatory skin disease. It affects approximately 2% of the western population and has no cure. Combination therapy for psoriasis often proves more efficacious and better tolerated than monotherapy with a single drug. Combination
Brian L Watson et al.
Physical chemistry chemical physics : PCCP, 17(24), 15788-15796 (2015-05-29)
A new sensitizer motif for dye sensitized solar cells (DSSC) has been developed. A heteroaromatic moiety containing a pyrazine ring links two porphyrin chromophores to the metal oxide surface via two carboxylic acid attachment groups. A test DSSC sensitized with
C Salet et al.
Archives of dermatological research, 283(3), 186-190 (1991-01-01)
Isolated mitochondria were used to determine what causes anthralin inhibition of oxidative phosphorylation. In good agreement with other results, the rate of oxygen consumption was not modified by anthralin when mitochondria were first uncoupled with FCCP, suggesting that only the
G C Hsieh et al.
Toxicology and applied pharmacology, 107(1), 16-26 (1991-01-01)
Primary cultured rat epidermal keratinocytes were used as an experimental model to detect oxidant-mediated adverse effects of dithranol (anthralin), a widely used antipsoriasis drug with tumor-promoting and skin-irritating properties. Keratinocytes were isolated and prepared from the skin of neonatal rats
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