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55079-83-9

Basic Information
CAS No.: 55079-83-9
Name: Acitretin
Molecular Structure:
Molecular Structure of 55079-83-9 (Acitretin)
Formula: C21H26O3
Molecular Weight: 326.43
Synonyms: (all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid;all-trans-3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenoic acid;Neotigason;2,4,6,8-Nonatetraenoic acid,9-(4-methoxy-2,3,6-trimethylphenyl)-3,- 7-dimethyl-,(2E,4E,6E,8E)-;Etretin;Acitretinum [Latin];Acitretina [Spanish];all-trans-Acitretin;Acitretine [French];Acitretin [USAN:BAN:INN];Soriatane;2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-, (all-E)-;
EINECS: 259-474-4
Density: 1.051 g/cm3
Melting Point: 228-230 °C
Boiling Point: 521.3 °C at 760 mmHg
Flash Point: 180.3 °C
Solubility:
Appearance: crystalline solid
Hazard Symbols: ToxicT, DangerousN
Risk Codes: 61-36/38-50/53
Safety: 53-26-45-60-61-37/39
Transport Information: UN 3077 9/PG 3
PSA: 46.53000
LogP: 5.16700
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Chemistry

Molecule structure of Acitretin (CAS NO.55079-83-9):

IUPAC Name: (2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid 
Molecular Weight: 326.42934 g/mol
Molecular Formula: C21H26O3 
Density: 1.051 g/cm3 
Melting Point: 228-230 °C
Boiling Point: 521.3 °C at 760 mmHg 
Flash Point: 180.3 °C
Index of Refraction: 1.569
Molar Refractivity: 101.78 cm3
Molar Volume: 310.3 cm3
Surface Tension: 38.6 dyne/cm 
Enthalpy of Vaporization: 83.64 kJ/mol
Vapour Pressure: 1.08E-11 mmHg at 25 °C 
Storage Temp.: 2-8 °C
XLogP3-AA: 6.1
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 6
Exact Mass: 326.188195
MonoIsotopic Mass: 326.188195
Topological Polar Surface Area: 46.5
Heavy Atom Count: 24 
Canonical SMILES: CC1=CC(=C(C(=C1C=CC(=CC=CC(=CC(=O)O)C)C)C)C)OC
Isomeric SMILES: CC1=CC(=C(C(=C1/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)C)C)OC
InChI: InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)
18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+
InChIKey: IHUNBGSDBOWDMA-AQFIFDHZSA-N
EINECS: 259-474-4
Product Categories: Active Pharmaceutical Ingredients; Various Metabolites and Impurities; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals; Retinoids; Intracellular receptor

Uses

 Acitretin (CAS NO.55079-83-9) is a synthetic retinoid which is the major metabolite of etretinate. It is typically used for psoriasis. Acitretin is a metabolite of etretinate, which was used prior to the introduction of acitretin.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 700mg/kg (700mg/kg)   United States Patent Document. Vol. #4105681,
rat LD50 oral > 4gm/kg (4000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 5033, 1982.

Safety Profile

Hazard Codes: ToxicT, DangerousN
Risk Statements: 61-36/38-50/53 
R61:May cause harm to the unborn child. 
R36/38:Irritating to eyes and skin. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 53-26-45-60-61-37/39 
S53:Avoid exposure - obtain special instructions before use. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S60:This material and its container must be disposed of as hazardous waste. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: RA8460000
F: 8-10-21
An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.

Specification

 Acitretin (CAS NO.55079-83-9) is also named as (all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid ; Acitretina ; Acitretina [Spanish] ; Acitretine ; Acitretine [French] ; Acitretinum ; Acitretinum [Latin] ; CCRIS 5534 ; Etretin ; HSDB 7187 ; Neotigason ; Retinoid etretin ; Ro 10-1670 ; Ro 10-1670/000 ; Soriatane ; TMMP ; U0279 ; UNII-LCH760E9T7 ; all-trans-3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenoic acid ; all-trans-Acitretin . Acitretin (CAS NO.55079-83-9) is crystalline solid.