Isoacitretin

Base Information

• Chemical Name: Isoacitretin
• CAS No.: 69427-46-9
• Molecular Formula: C21H26 O3
• Molecular Weight: 326.436
• Hs Code.: 2918992090
• UNII: BK59Y5A02O
• DSSTox Substance ID: DTXSID901316817
• Wikidata: Q27121938
• Metabolomics Workbench ID: 38239
• Mol file: 69427-46-9.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 Isoacitretin

Chemical Property:

• Melting Point: 190-193°C
• Boiling Point: 521.3±38.0 °C(Predicted)
• PKA: 4.75±0.33(Predicted)
• PSA: 46.53000
• Density: 1.051±0.06 g/cm3(Predicted)
• LogP: 5.16700
• Storage Temp.: Amber Vial, -80°C Freezer
• 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:

98%Min ^*data from raw suppliers

13-cis-Acitretin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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

Technology Process of Isoacitretin

There total 40 articles about Isoacitretin 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:

13-cis-Acitretin

acitretin

(2E,4E,6E,8E)-9-(4-methoxyl-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenal

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

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.