[CAS NO. 514-85-2] 9-cis-Retinal
PRODUCTS SPECIFICATIONS [514-85-2]
DESCRIPTION [514-85-2]
Overview
| MDL | - |
|---|---|
| Molecular Weight | 284.44 |
| Molecular Formula | C20H28O |
| SMILES | CC(/C=C/C=C(\C=C\C1=C(CCCC(C)1C)C)C)=C\C=O |
Summary
9-cis-Retinal is a natural retinoid. Dietary 9-cis-β-carotene generates 9-cis-retinoids via cleavage into 9-cis-retinal. 9-cis Retinal binds to cellular retinol-binding protein-I (CRBP-I) and CRBP-II with K d s of 8 nM and 5 nM, respectively. 9-cis-Retinal expedites differentiation and maturation of rod photoreceptors in retinal organoids [1] [2] [3] .
IC50 & Target
|
Human Endogenous Metabolite |
In Vitro
The addition of 9-cis-Retinal, instead of the widely used all-trans retinoic acid, accelerates rod photoreceptor differentiation in organoid cultures, with higher rhodopsin expression and more mature mitochondrial morphology evident by day. 9-cis-Retinal can bind opsin to form functioning rhodopsin [3] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
Treatment with 9-cis-retinal produced a significant recovery of the cone response in interphotoreceptor retinoid-binding protein (IRBP) -/- mice and shows that retinoid deficiency underlies cone dysfunction [4] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
-20°C, protect from light, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)
Solvent & Solubility
DMSO : 16 mg/mL ( 56.25 mM ; Need ultrasonic and warming)
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 3.5157 mL | 17.5784 mL | 35.1568 mL |
| 5 mM | 0.7031 mL | 3.5157 mL | 7.0314 mL |
| 10 mM | 0.3516 mL | 1.7578 mL | 3.5157 mL |
References
- [1] Kane MA, et al. Binding affinities of CRBPI and CRBPII for 9-cis-retinoids.Biochim Biophys Acta. 2011 May;1810(5):514-8.
- [2] Mertz JR, et al. Identification and characterization of a stereospecific human enzyme that catalyzes 9-cis-retinol oxidation. A possible role in 9-cis-retinoic acid formation. J Biol Chem. 1997 May 2;272(18):11744-9.
- [3] Kaya KD, et al. Transcriptome-based molecular staging of human stem cell-derived retinal organoids uncovers accelerated photoreceptor differentiation by 9-cis retinal. Mol Vis. 2019 Nov 11;25:663-678.
- [4] Parker RO, et al. Normal cone function requires the interphotoreceptor retinoid binding protein. J Neurosci. 2009 Apr 8;29(14):4616-21.
Synonyms