9-cis-13,14-Dihydro-retinoic acid

9-cis-13,14-Dihydro-retinoic acid is a retinoid, a class of chemical compounds that are vitamers of vitamin A or are chemically related to it. Retinoids are important in medicine due to their role in regulating cell growth, vision, and immune function.

Chemical Structure and Properties

9-cis-13,14-Dihydro-retinoic acid is a derivative of retinoic acid, which is an active metabolite of vitamin A. The "9-cis" configuration refers to the specific geometric isomerism of the double bonds in the retinoid structure, which affects its biological activity. The "13,14-dihydro" designation indicates the saturation of the double bond between the 13th and 14th carbon atoms in the retinoid backbone.

Molecular Formula

The molecular formula of 9-cis-13,14-Dihydro-retinoic acid is C20H30O2.

Molecular Weight

The molecular weight of this compound is approximately 302.45 g/mol.

Biological Activity

9-cis-13,14-Dihydro-retinoic acid is known to interact with retinoic acid receptors (RARs) and retinoid X receptors (RXRs), which are nuclear receptors that regulate gene expression. These interactions are crucial for the modulation of various biological processes, including cell differentiation, proliferation, and apoptosis.

Role in Vision

Retinoids, including 9-cis-13,14-Dihydro-retinoic acid, play a critical role in the visual cycle. They are involved in the regeneration of rhodopsin, a light-sensitive receptor protein in the retina that is essential for vision in low-light conditions.

Therapeutic Applications

Due to its ability to modulate gene expression, 9-cis-13,14-Dihydro-retinoic acid has potential therapeutic applications in dermatology, oncology, and the treatment of certain autoimmune diseases. Its role in regulating cell growth and differentiation makes it a candidate for cancer therapy, particularly in cancers where retinoid signaling is disrupted.

Synthesis and Derivation

9-cis-13,14-Dihydro-retinoic acid can be synthesized from beta-carotene or other retinoid precursors through a series of chemical reactions that involve isomerization and reduction. The synthesis process is crucial for producing this compound in a form that is suitable for research and therapeutic use.

Safety and Toxicity

As with other retinoids, the use of 9-cis-13,14-Dihydro-retinoic acid must be carefully monitored due to potential side effects, including teratogenicity, which is the ability to cause birth defects. It is important to adhere to recommended dosages and guidelines when using retinoids in clinical settings.

Also see

• Retinoic acid
• Retinoid X receptor
• Vitamin A
• Rhodopsin
• Beta-carotene