14398-58-4

Upstream product

• 6153-05-5 (Z)-3-methylpent-2-en-4-ynol 
• 187339-53-3 (2E,4Z,6E)-7-(1-Hydroxy-2,2,6-trimethyl-cyclohexyl)-5-methyl-hepta-2,4,6-trienoic acid methyl ester 
• 187339-52-2 (2Z,4E)-3-methyl-5-(1-hydroxy-2,2,6-trimethylcyclohexyl)-pent-2,4-dien-1-al 
• 187409-93-4 1-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-2,2,6-trimethyl-cyclohexanol 
• 187339-51-1 (2Z,4E)-3-methyl-5-(1-hydroxy-2,2,6-trimethylcyclohexyl)-pent-2,4-dien-1-ol 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 14398-59-5 (2E,4Z,6E)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid methyl ester 

Downstream Products

• 67567-19-5 9-cis-β-ionylidenecrotonaldehyde 
• 25529-00-4 6-methyl-8t-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3t,5c,7-trien-2-one 
• 302-79-4 9-cis-retinoic acid 
• 58526-50-4 [7t,9c,11t,13t]retinoic acid methyl ester 
• 78769-76-3 (3E,5Z,7E)-6-Methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trien-2-ol 
• 187339-56-6 C₁₈H₂₃⁽²⁾H₃O 
• 187339-57-7 (2E,4Z,6E)-1-³H₃C,5-methyl-7-(2,2,6-trimethylcyclohex-1-enyl)-hepta-2,4,6-triene-1-one 
• 187339-54-4 C₁₈H₂₅⁽²⁾H₃O 
• 187339-55-5 (2E,4Z,6E)-1-³H₃C,5-methyl-7-(2,2,6-trimethylcyclohex-1-enyl)-hepta-2,4,6-triene-1-ol 
• 187339-59-9 methyl-(2E,4E,6Z,8E)-3-³H₃C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate 
• 187339-58-8 C₂₁H₂₇⁽²⁾H₃O₂ 

Relevant academic research and scientific papers

Synthesis of 9-cis-retinoic acid and C-20-[3H3C]-9-cis-retinoic acid with high specific activity

The synthesis of 9-cis-retinoic acid starting from 2,2,6-trimethylcyclohexanone is described. The same methodology was extended for the synthesis of deuterium and tritium labeled 9-cis-retinoic acid with high specific activity (73 Ci/mmol). In this methodology, a Grignard reaction was utilized for introducing three tritium atoms simultaneously in the final synthetic steps.

Polyenylidene thiazolidine derivatives with retinoidal activities

Several polyenylidene thiazolidinedione or 2-thioxo-4-thiazolidinone derivatives were synthesized and their retinoidal activities were examined in terms of the differentiation-inducing ability towards human promyelocytic leukemia HL-60 cells and inhibitory effect on interleukin (IL)-1α-induced IL-6 production in MC3T3-E1 cells. Compounds containing a trimethylcyclohexenyl ring induced HL-60 cell differentiation with weaker activity than retinoic acid (1a) by one or two orders of magnitude. The thiazolidinedione derivatives (2, 5, 7) showed stronger activity than the corresponding 2-thioxo-4-thiazolidinone derivatives (3, 6, 8). The effects of a retinoid antagonist (LE540) and synergists (retinoid X receptor (RXR) agonists, HX600 or HX630) on the activities of thiazolidine derivatives indicate that these compounds elicit their activities through the nuclear retinoic acid receptors (RARs). All the thiazolidines examined also inhibited IL-1α-induced IL-6 production with IC50 values of 10nM order. The retinoidal activities of the thiazolidines are significant, considering that replacement of the carboxylic acid in retinoid structures with bioisosteric functional groups is generally ineffective, as seen in the structure-activity relationships of retinoidal benzoic acids.