1007602-46-1

Upstream product

• 1007220-96-3 ethyl (3S,4E)-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-enoate 
• 138846-06-7 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene 
• 661492-75-7 2,6,6-trimethylcyclohex-1-en-1-ylboronic acid 
• 128426-10-8 (2E,4E)-5-(tri-n-butylstannyl)-3-methylpenta-2,4-dien-1-ol 
• 888484-41-1 ethyl (3S)-3-methyl-4-oxobutanoate 

Downstream Products

• 1007221-00-2 all-trans-(S)-13,14-Dihydroretinoic acid 
• 1007220-98-5 all-trans-(S)-13,14-Dihydroretinol 

Relevant academic research and scientific papers

Stereocontrolled synthesis of (S)-9-cis- and (S)-11-cis-13,14-dihydroretinoic acid

The 9-cis and 11-cis stereoisomers of 13,14-dihydroretinoic acid with S configuration, (S)-7 and (S)-9, respectively, have been synthesized stereoselectively. The former has been recently characterized as the first endogenous natural ligand of the retinoid X receptor (RXR). The Julia-Kocienski reaction of allyl sulfones and aldehydes was used as connective step and afforded the Z isomer of a trienyl ester accounting for the entire side chain of the targets. A highly selective and unidirectional iodine-induced isomerization of a Z,Z,E triene to the desired E,Z,E isomer was required prior to the synthesis of (S)-7 via a Suzuki cross-coupling. The same approach to (S)-9 led to substantial isomerization when the Suzuki cross-coupling was used as the last bond-forming reaction. As alternative, the two bond-forming steps were exchanged and the synthesis of (S)-9 was completed using the Z-selective Julia-Kocienski reaction.

COMPOSITIONS AND METHODS FOR TREATING METABOLIC DISEASES

A pharmaceutical composition for treating a metabolic disease in a mammalian subject includes a therapeutically effective amount of all-trans-13,14-dihydroretinoid, all-trans-13,14-dihydroretinoid derivative, or agent capable of modulating the level of at least one all-trans-13,14-dihydroretinoid or all-trans-13,14-dihydroretinoid derivative in the subject.

Stereospecificity of retinol saturase: Absolute configuration, synthesis, and biological evaluation of dihydroretinoids

Retinol saturase carries out a stereospecific saturation of the C13-C14 double bond of all-trans-retinol to generate (13R)-all-trans-13,14-dihydroretinol. This compound is found in cells expressing mouse or zebrafish retinol saturase and in the livers of mice fed retinyl palmitate. All-trans-13,14-dihydroretinol is oxidized in vivo to all-trans-13,14-dihydroretinoic acid, a highly selective agonist of the retinoic acid receptor. The naturally occurring (13R)-all-trans-13,14-dihydroretinoic acid is a weaker agonist than the (13S) enantiomer, indicating enantioselective recognition by the ligand-binding pocket of this receptor. Consequently the (13S) enantiomer, acting through the retinoic acid receptor, also inhibits adipose differentiation more potently than the (13R) enantiomer. Copyright