1,8-dihydroxy-9,10-dihydroanthracen-9-one

• ChemBase ID: 105600
• Molecular Formular: C14H10O3
• Molecular Mass: 226.2274
• Monoisotopic Mass: 226.06299418
• SMILES: Oc1cccc2c1C(=O)c1c(C2)cccc1O
• Canonical SMILES: Oc1cccc2c1C(=O)c1c(C2)cccc1O
• 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
• InChIKey: NUZWLKWWNNJHPT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,8-dihydroxy-9,10-dihydroanthracen-9-one
• IUPAC Traditional name: anthralin
• Synonyms: Dithranol; Anthraforte; Cignolin; Micanol; Psoriderm; Anthralin; 1,8-Dihydroxy-9(10H)-anthracenone; 1,8-Dihydroxyanthrone; Dithranol; Anthralin; 1,8 Dihydroxyanthrone; 1,8,9-Anthracenetriol; DITHRANOL; 1,8,9-蒽三酚; 1,8-二羟基蒽-9(10H)-酮; 二羟蒽酚; 蒽林; 地蒽酚

Database IDs

• CAS Number: 1143-38-0
• EC Number: 214-538-0
• MDL Number: MFCD00053409
• Beilstein Number: 2054360
• PubChem SID: 162092151; 24893712; 24846722
• PubChem CID: 2202

CALCULATED PROPERTIES

• Acid pKa: 9.669733
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.243987
• LogD (pH = 7.4): 4.241703
• Log P: 4.2440166
• Molar Refractivity: 64.2745 cm^3
• Polarizability: 24.218582 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Benzene; Chloroform
• Apperance: Yellow Crystalline Solid
• Melting Point: 176-181°C; 178-181 °C(lit.); 178-183 °C
• Absorption Wavelength: absorption 337 nm, >2000

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: CB8927000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: mouse ... Alox12(11684)

Product Information

• Purity: ≥90% (HPLC); ≥98.0%; ≥98.0% (HPLC); ≥98.5% (HPLC); 99%
• Grade: matrix substance for MALDI-MS; puriss. p.a.
• Suitability: in accordance for UV test
• Cation Traces: Ba: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤20 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤20 mg/kg; Pb: ≤5 mg/kg; Zn: ≤10 mg/kg
• Analyte suitability: dendrimers; lipids; polymers
• abs.: absorption/337 nm ≥2000 (mol. absorption)
• Empirical Formula (Hill Notation): C14H10O3

DETAILS

MP Biomedicals - 02191502

Purity: 99%
Inhibits leukotriene biosynthesis.

Sigma Aldrich - D2773

Application
Dithranol, an athracene derivative, is a free radical generating mitochondrial poison that induces apoptosis in keratinocytes. Dithranol is being studied as a potential anti-psoriasis medication.

Sigma Aldrich - 10608

Other Notes
Matrix substance for MALDI-MS (matrix-assisted laser desorption ionization MS)1

Toronto Research Chemicals - A679200

Antipsoriatic.

REFERENCES

• Ashton, R.E., et al.: J. Am. Acad. Dermatol., 9, 173 (1983)
• Kemeny, L., et al.: Skin Pharmacol., 3, 1 (1983)
• Mahrle, G., et al.: Clin. Dermatol., 15, 723 (1997)