Acitretin

Base Information

• Chemical Name: Acitretin
• CAS No.: 54757-46-9
• Molecular Formula: C₂₁H₂₆O₃
• Molecular Weight: 326.436
• European Community (EC) Number: 259-474-4
• UNII: LCH760E9T7
• DSSTox Substance ID: DTXSID6022553
• Nikkaji Number: J23.289K,J261.795A
• Wikipedia: Acitretin
• Wikidata: Q341500
• NCI Thesaurus Code: C985
• RXCUI: 16818
• Pharos Ligand ID: KZFPFPZVL7XB
• Metabolomics Workbench ID: 144476
• ChEMBL ID: CHEMBL1131
• Mol file: 54757-46-9.mol

Synonyms:13-cis-Acitretin;Acitretin;Acitretin, (Z,E,E,E)-Isomer;Etretin;Isoacitretin;Isoetretin;Neotigason;Ro 10-1670;Ro 101670;Ro 13-7652;Ro 137652;Ro-10-1670;Ro-13-7652;Ro101670;Ro137652;Soriatane

Chemical Property of Acitretin

Chemical Property:

• Boiling Point: 521.3°Cat760mmHg
• Flash Point: 180.3°C
• PSA: 46.53000
• Density: 1.051g/cm³
• LogP: 5.16700
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 326.18819469
• Heavy Atom Count: 24
• Complexity: 539

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Dermatologic Agents
• 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
• Recent ClinicalTrials: Outcomes With Treatment and Withdraw of Secukinumab in Patients With Plaque Psoriasis
• Recent EU Clinical Trials: The induction of apoptosis by anti-psoriatic treatments

Technology Process of Acitretin

There total 27 articles about Acitretin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

13-cis-Acitretin (69427-46-9,1067630-53-8,419534-31-9) → acitretin (54757-46-9,69427-46-9,69427-47-0,55079-83-9,1067630-53-8,419534-31-9)

Guidance literature:

With iodine; In diethyl ether; benzene; at 20 ℃; for 8h;

Reference yield: 94.0%

3,7-dimethyl-7-hydroxy-9-(4-methoxy-2,3,6-trimethylphenyl)-nona-2,4,8-trienoic acid → acitretin (54757-46-9,69427-46-9,69427-47-0,55079-83-9,1067630-53-8,419534-31-9)

Guidance literature:

With iodine; toluene-4-sulfonic acid; 1.) methylene dichloride, reflux, 15 min; 2.) diethyl ether/benzene, rt, 7 h;

DOI:10.1016/0040-4020(95)00114-N

Reference yield: 88.5%

isobutyl ester of (all-E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid → acitretin (54757-46-9,69427-46-9,69427-47-0,55079-83-9,1067630-53-8,419534-31-9)

Guidance literature:

With potassium hydroxide; In ethanol; for 0.75h; Heating;

DOI:10.1007/BF02218431

upstream raw materials:

13-cis-Acitretin

2-[(2E,4E,6E)-7-(4-Methoxy-2,3,6-trimethyl-phenyl)-1,5-dimethyl-hepta-2,4,6-trienylidene]-malonic acid

methyl ethyl β-methylglutaconate

5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2(E),4(E)-pentadien-1-al

Downstream raw materials:

(4-trifluoromethoxyphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

(3-trifluoromethylphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid chloride

(4-amino-2-trifluoromethylphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

Refernces

• 1、 -. "Novel isomerization method of acitretin". Paragraph 0059-0070. . Retrieved 2018/10/19.
• 2、 -. "STEREOSPECIFIC SYNTHESIS PROCESS FOR TRETINOIN COMPOUNDS". Paragraph 0045; 0046. . Retrieved 2014/04/03.