81176-73-0

Basic information

• Product Name: 11-cis,13-cis-12-carboxyretinoic acid
• Synonyms: 11-cis,13-cis-12-carboxyretinoic acid
• CAS NO: 81176-73-0
• Molecular Weight: 344.451
• Mol File: 81176-73-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 11-cis,13-cis-12-carboxyretinoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 11-cis,13-cis-12-carboxyretinoic acid(81176-73-0)
• EPA Substance Registry System: 11-cis,13-cis-12-carboxyretinoic acid(81176-73-0)

Safety Data

• Hazardous Substances Data: 81176-73-0(Hazardous Substances Data)

Upstream product

• 3917-39-3 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol 
• 1224-76-6 9-hydroxy-β-ionylideneacetaldehyde dimethyl acetal 
• 83860-26-8 13-cis-12-carboxyretinoic anhydride 
• 52313-87-8 3-methyl-2-pentene-1,5-diacid dimethyl 
• 54226-17-4 (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal 
• 924-59-4 diethyl 3-methylpent-2-enedioate 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 67-56-1 methanol 
• 80040-38-6 13-cis-12-carboxyretinoic acid dimethyl ester 
• 81061-91-8 dimethyl 3-methyl-2-cis-pentenedioate 
• 3917-40-6 (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienol 

Downstream Products

• 302-79-4 9-cis-retinoic acid 
• 81177-15-3 11-cis,13-cis-12-carboxyretinoic anhydride 
• 4759-48-2 13-cis-retinoic acid 
• 70244-78-9 2-((1E,3E,5E)-3,7-dimethylocta-1,3,5,7-tetraen-1-yl)-1,3,3-trimethylcyclohex-1-ene 
• 83860-28-0 methyl 11-cis,13-cis-12-carboxyretinoate 
• 302-79-4 9,13-di-cis-retinoic acid 

Relevant articles and documents

SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS. -- XLVIII. STRUCTURE AND TRANSFORMATIONS OF 12-CARBOXYRETINOIC ACIDS AND THEIR ESTERS. SYNTHESIS OF 13-CIS-RETINOIC ACID

In reaction with ethyl β-methylglutaconate under the influence of alkali in methanol the Z and E isomers of β-ionylideneacetaldehyde form isomeric 9Z,11Z,13Z- and 9E,11Z,13Z-12-carboxyretinoic acids.Decarboxylation of the latter in the pyridine-piperidine system in the presence of copper salts leads to 13Z-retinoic acid and is accompanied by the formation of 9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-octatetraene.The stereoisomeric transformations of 12-substituted 9E,Z,11Z,13Z-retinoic acids and the corresponding diols and diacetates obtained from them were investigated.Isomerization takes place at the double bond at the C9 atom and depends on the nature of the substituent at the C12 atom.