138093-42-2

Basic information

• Product Name: 14-Isopropylretinoic acid
• CAS NO: 138093-42-2
• Molecular Weight: 342.522
• Mol File: 138093-42-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 14-Isopropylretinoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 14-Isopropylretinoic acid(138093-42-2)
• EPA Substance Registry System: 14-Isopropylretinoic acid(138093-42-2)

Safety Data

• Hazardous Substances Data: 138093-42-2(Hazardous Substances Data)

Upstream product

• 138093-39-7 14-isopropyl-20,14-retro-retinoic acid 
• 68-26-8 retinol 
• 3899-20-5 ethyl retinoate 
• 302-79-4 all-trans-retinoic-acid 
• 79-81-2 retinyl palmitate 
• 138093-45-5 methyl 14-isopropyl-20,14-retro-retinoate 

Relevant articles and documents

Base-catalyzed isomerization of retinoic acid. Synthesis and differentiation-inducing activities of 14-alkylated all-trans-, 13-cis-, and 20,14-retro-retinoic acids

Retinoic acid (1) is isomerized regioselectively by excess amounts of lithium diisopropylamide (LDA) to give 20,14-retro-retinoic acid (3). Alkylation of the intermediate dianion of retinoic acid gave 14-alkylated derivatives of 3. By isomerization of the alkylated retro isomers under basic conditions, several 14-alkyl-all-trans- and -13-cis-retinoic acids were synthesized. The retinoidal activities of these derivatives were examined, based on the ability to induce differentiation of human promyelocytic leukemia cell line HL-60. 20,14-retro-Retinoic acid (3) is 1/50 as active as retinoic acid (1). Although 14-methyl-20,14-retro-retinoic acid (4) is as active as 3, the introduction of a 14-methyl group into all-trans- and 13- cis-retinoic acid resulted in decreased activity. Introduction of bulkier alkyl groups at the C-14 position caused the disappearance of the activity.