69427-46-9

Basic information

• Product Name: 13-CIS-ACITRETIN
• Synonyms: 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoicAcid,13-cis-Etretin,Isoacitretin,Isoetretin,;9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid, 13-cis-Etretin, Isoacitretin, Isoetretin, Ro 13-7652;(2Z,4E,6Z,8E)-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid;Isoacitretin;13-CIS-ETRETIN;(2Z,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid;Isoetretin;Ro-13-7652
• CAS NO: 69427-46-9
• Molecular Formula: C₂₁H₂₆O₃
• Molecular Weight: 326.433
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;Retinoids;Aromatics;Metabolites & Impurities
• Mol File: 69427-46-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 190-193°C
• Boiling Point: 521.3±38.0 °C(Predicted)
• Appearance: /
• Density: 1.051±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, -80°C Freezer
• PKA: 4.75±0.33(Predicted)
• CAS DataBase Reference: 13-CIS-ACITRETIN(CAS DataBase Reference)
• NIST Chemistry Reference: 13-CIS-ACITRETIN(69427-46-9)
• EPA Substance Registry System: 13-CIS-ACITRETIN(69427-46-9)

Safety Data

• Hazardous Substances Data: 69427-46-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Upstream product

• 131980-79-5 methyl ethyl β-methylglutaconate 
• 69877-38-9 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2(E),4(E)-pentadien-1-al 
• 54350-48-0 etretinate 
• 419534-29-5 (2E,4E)/(2Z,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal 
• 22035-53-6 dimethyl isopropylidenemalonate 
• 127613-71-2 9-(4-methoxy-2,3,6-trimethylphenyl)-4-carboxy-3,7-dimethyl-2Z,4Z,6E,8E-nonatetraenoic acid 
• 478496-93-4 2-[(2E,4E,6E)-7-(4-Methoxy-2,3,6-trimethyl-phenyl)-1,5-dimethyl-hepta-2,4,6-trienylidene]-malonic acid 
• 69427-46-9 13-cis-Acitretin 
• 108518-66-7 3-formyl-crotonic acid butyl ester 
• 74479-40-6 butyl {(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl)phenyl-3,7-dimethylnona-2,4,6.8}tetraenoate 
• 111-92-2 dibutylamine 
• 123-38-6 propionaldehyde 
• 6295-06-3 butyl glyoxalate 
• 87424-82-6 (E)-2-Methyl-3-(4-methyl-2-oxo-2H-pyran-6-yl)propenal 

Downstream Products

• 69427-46-9 13-cis-Acitretin 
• 54757-46-9 acitretin 
• 54757-57-2 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid allyl ester 
• 1197356-84-5 (2-trifluoromethoxyphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid amide 
• 1197356-82-3 (3-trifluoromethoxyphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid amide 
• 1197356-69-6 (3-trifluoromethoxyphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid amide 
• 1197356-74-3 (4-amino-3-trifluoromethylphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimeth yl-2,4,6,8-nonatetraenoate 
• 1197356-76-5 (4-amino-2-trifluoromethylphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate 
• 74479-50-8 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid chloride 
• 1197356-63-0 (3-trifluoromethylphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate 
• 1197356-78-7 (4-trifluoromethoxyphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate 
• 666854-55-3 succinimidyl acitretinate 
• 1160953-96-7 C₃₄H₄₈N₂O₃ 
• 74479-47-3 9-(4-methoxy-2,3,5,6-tetramethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester 

Relevant articles and documents

Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters

Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.

PROCESS FOR PREPARATION OF ACITRETIN

The present invention provides a process for preparation of {(2E,4E,6E,8E)-9-(4-methoxy-2,3,6- trimethyl)phenyl-3,7-dimethyl-nona-2,4,6,8}tetraenoate, an acitretin intermediate of formula (VI) with trans isomer ≥97%, comprising of reacting 3-formyl-crotonic acid butyl ester of formula (V), substantially free of impurities, with 5-(4-methoxy-2,3,6-trimethylphenyl)-3- methyl-penta-2,4-diene-l-triphenyl phosphonium bromide of formula (IV) and isolating resultant compound of formula (VI), treating the filtrate with iodine for isomerization of the undesired cis intermediate and finally obtaining acitretin (I), with desired trans isomer ≥97%.

Stereospecific synthesis process for tretinoin compounds

A stereospecific synthesis process for tretinoin compounds comprises the following steps: using substituted triphenyl phosphine salt and β-formyl crotonic acid as raw material to carry out WITTIG reaction under the action of alkali; then adjusting the pH of the reaction liquid to 5-10; adding palladium compound or rhodium compound to carry out isomerization directly and obtain tretinoin compounds with desired configuration. The product yield of the process is high and the intermediate product in the reaction dose not need to be separated. The process is easy to operate and can save the production cost and as well is suitable for industrial production.