86708-70-5

Basic information

• Product Name: ethyl all-cis-retinoate
• CAS NO: 86708-70-5
• Molecular Weight: 328.495
• Mol File: 86708-70-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: ethyl all-cis-retinoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl all-cis-retinoate(86708-70-5)
• EPA Substance Registry System: ethyl all-cis-retinoate(86708-70-5)

Safety Data

• Hazardous Substances Data: 86708-70-5(Hazardous Substances Data)

Upstream product

• 79-81-2 retinyl palmitate 
• 55646-04-3 7-formyl-3-methyl-2,4,6-octatrienoic acid ethyl ester 
• 472-20-8 β-cyclogeraniol 
• 101083-54-9 (E)-4,6,6-Triethoxy-3-methyl-hex-2-enoic acid ethyl ester 
• 3899-20-5 ethyl retinoate 
• 85354-07-0 (3Z,5Z,7Z)-6-Methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trien-2-one 
• 85319-52-4 (5Z,7Z)-6-Methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-5,7-dien-3-yn-2-one 
• 85319-51-3 (5Z,7Z)-6-Methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-5,7-dien-3-yn-2-ol 
• 85319-50-2 2-((1Z,3Z,5E)-6-Chloro-3-methyl-hexa-1,3,5-trienyl)-1,3,3-trimethyl-cyclohexene 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 928-55-2 ethyl 1-propenyl ether 
• 64-17-5 ethanol 
• 68-26-8 retinol 

Downstream Products

• 302-79-4 all-trans-retinoic-acid 
• 124510-04-9 7-cis-retinoic acid 
• 3899-20-5 ethyl (all-E)-retinoate 
• 86708-70-5 9,11,13-tri-cis-ethyl retinoate 
• 86708-68-1 9-cis-13,14-dihydroretinoic acid ethyl ester 
• 86708-67-0 ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 
• 51249-34-4 11-cis-ethyl retinoate 
• 59699-82-0 ethyl 13-cis-retinoate 
• 138093-48-8 (2E,4E,6E,8E)-2-Isopropyl-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid methyl ester 
• 138232-02-7 (2Z,4E,6E,8E)-2-Isopropyl-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid methyl ester 
• 138093-47-7 (2E,4E,6E,8E)-2-Ethyl-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid methyl ester 
• 138232-01-6 (2Z,4E,6E,8E)-2-Ethyl-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid methyl ester 
• 138093-42-2 14-Isopropylretinoic acid 
• 138231-99-9 13-cis-14-Isopropylretinoic acid 

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.

Syntheses of ethyl retinoate with polymer-supported Wittig reagents

-