176019-01-5

Usage

Uses

Used in Pharmaceutical Industry:
(9Z,13R)-13,14-dihydroretinoic acid is used as a therapeutic agent for treating various vision-related disorders and conditions. Its role in the visual system makes it a promising candidate for the development of treatments targeting retinal diseases and other vision impairments.
Used in Research and Development:
In the field of research, (9Z,13R)-13,14-dihydroretinoic acid is utilized as a key compound for studying the mechanisms of vision and the role of retinal in the visual pigments. This helps scientists better understand the underlying processes and develop new strategies for treating related conditions.
Used in Nutritional Supplements:
Due to its connection with the visual system and the corotenoids, (9Z,13R)-13,14-dihydroretinoic acid may also be used as an ingredient in nutritional supplements aimed at supporting eye health and maintaining optimal vision function.

Upstream product

• 1007602-45-0 ethyl (13R)-13,14-dihydroretinoate 
• 1007602-46-1 ethyl (11E,13S)-13,14-dihydroretinoate 
• 115797-14-3 13,14-dihydro-all-trans retinol 
• 172302-35-1 13,14-dihydroretinal 
• 54998-57-1 ethyl 3-formylbutyrate 
• 41891-38-7 3-formyl crotonic acid ethyl ester 
• 79-77-6 (E)-β-ionone 
• 116-31-4 all-trans-Retinal 
• 17974-55-9 (2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 62924-13-4 ethyl 13,14-dihydroretinoate 
• 68-26-8 RETINOL 
• 62285-98-7 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide 
• 128426-10-8 (2E,4E)-5-(tri-n-butylstannyl)-3-methylpenta-2,4-dien-1-ol 

Relevant academic research and scientific papers

Natural ligands of RXR receptors

Given the role of retinoid X receptors (RXRs) as promiscuous partners of heterodimeric complexes with other members of the Nuclear Receptor (NR) superfamily, RXR ligands (rexinoids) play fundamental roles in gene transcription, since upon ligand binding either transcriptionally activate the “permissive” subclass of heterodimers or synergize with partner ligands in the “non-permissive” subclass of heterodimers. The collection of natural products thus far reported to bind RXR are described, including those discovered by high-throughput screening (HTS), mere serendipity, and a combination of those. Detailed protocols for the diastereo- and enantioselective synthesis of (R)-9-cis-13,14-dihydroretinoic acid, a putative natural RXR ligand, are provided.

PRECURSOR COMPOUNDS FOR PROVIDING RETINOIDS OF THE VITAMIN A5 PATHWAY AND USES THEREOF

The invention relates to the field of retinoid X receptor (RXR) signalling and a novel vitamin A pathway called Vitamin A5 pathway. Compounds which are useful to provide (R) 9-cis-13,14-dihydro-retinoic acid an endogenous RXR ligand are claimed as well as their uses and method for preparation thereof. The compounds of the invention are useful for pharmaceutical and nutritional uses.

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.

STEREOSELECTIVE SYNTHESIS OF 9-CIS.13,14-DIHYDRORETINOIC ACID AND ITS ETHYL ESTERS

The retinoid X receptors (RXRs) are ligand-activated transcription factors heterodimerize with a number of nuclear hormone receptors, thereby controlling a variety of physiological processes. The invention relates to novel enantiomer compounds which are derivatives of dihydroretinoic acid, their stereoselective synthesis, to pharmaceutical compositions containing the same and to the use of same in the treatment of diseases.

All-Trans-Retinol: All-Trans-13,14-Dihydroretinol Saturase and Methods of Its Use

Compositions of all-trans-retinol: all-trans-13,14-dihydroretinal saturase and methods of use thereof are provided.

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