Molecular structure of 11-cis Retinal, CAS Number: 564-87-4
11-cis Retinal (CAS 564-87-4)
See product citations (2)
Alternate Names:
11-cis Retinal also known as (11Z)-Retinal; 11-cis-Retinaldehyde; 11-cis-Vitamin A Aldehyde; Neoretinene b
Application:
11-cis Retinal is a natural chromophore and is the oxidized form of 11-cis retinol, a naturally-occurring component used in vision
CAS Number:
564-87-4
Purity:
≥65%
Molecular Weight:
284.44
Molecular Formula:
C20H28O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
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SDS & Certificate of Analysis
11-cis Retinal is the oxidized form of 11-cis retinol (sc-476733), a naturally-occurring component used in vision. It binds with the protein opsin to form the highly conjugated rhodopsin, a compound that is responsible for vision in low-light conditions and the biologically active component of rod photoreceptors. 11-cis Retinal plays a vital role in vision, growth, and development. It is involved in the regulation of cell growth and differentiation, gene expression, and the immune system.
11-cis Retinal (CAS 564-87-4) References
- Interaction of 11-cis-retinol dehydrogenase with the chromophore of retinal g protein-coupled receptor opsin. | Chen, P., et al. 2001. J Biol Chem. 276: 21098-104. PMID: 11274198
- 11-cis-retinal reduces constitutive opsin phosphorylation and improves quantum catch in retinoid-deficient mouse rod photoreceptors. | Ablonczy, Z., et al. 2002. J Biol Chem. 277: 40491-8. PMID: 12176991
- Cone opsin mislocalization in Rpe65-/- mice: a defect that can be corrected by 11-cis retinal. | Rohrer, B., et al. 2005. Invest Ophthalmol Vis Sci. 46: 3876-82. PMID: 16186377
- R91W mutation in Rpe65 leads to milder early-onset retinal dystrophy due to the generation of low levels of 11-cis-retinal. | Samardzija, M., et al. 2008. Hum Mol Genet. 17: 281-92. PMID: 17933883
- Nrl-knockout mice deficient in Rpe65 fail to synthesize 11-cis retinal and cone outer segments. | Feathers, KL., et al. 2008. Invest Ophthalmol Vis Sci. 49: 1126-35. PMID: 18326740
- Light prevents exogenous 11-cis retinal from maintaining cone photoreceptors in chromophore-deficient mice. | Fan, J., et al. 2011. Invest Ophthalmol Vis Sci. 52: 2412-6. PMID: 21228385
- Orientation of retinal in bovine rhodopsin determined by cross-linking using a photoactivatable analog of 11-cis-retinal. | Nakayama, TA. and Khorana, HG. 1990. J Biol Chem. 265: 15762-9. PMID: 2144289
- Acute systemic 11-cis-retinal intervention improves abnormal outer retinal ion channel closure in diabetic mice. | Berkowitz, BA., et al. 2012. Mol Vis. 18: 372-6. PMID: 22355248
- Low aqueous solubility of 11-cis-retinal limits the rate of pigment formation and dark adaptation in salamander rods. | Frederiksen, R., et al. 2012. J Gen Physiol. 139: 493-505. PMID: 22641642
- Cellular retinaldehyde binding protein-different binding modes and micro-solvation patterns for high-affinity 9-cis- and 11-cis-retinal substrates. | Helbling, RE., et al. 2013. J Phys Chem B. 117: 10719-29. PMID: 23964907
- ATP-binding cassette transporter ABCA4 and chemical isomerization protect photoreceptor cells from the toxic accumulation of excess 11-cis-retinal. | Quazi, F. and Molday, RS. 2014. Proc Natl Acad Sci U S A. 111: 5024-9. PMID: 24707049
- RDH13L, an enzyme responsible for the aldehyde-alcohol redox coupling reaction (AL-OL coupling reaction) to supply 11-cis retinal in the carp cone retinoid cycle. | Sato, S., et al. 2015. J Biol Chem. 290: 2983-92. PMID: 25533474
- Measurement of Slow Spontaneous Release of 11-cis-Retinal from Rhodopsin. | Tian, H., et al. 2017. Biophys J. 112: 153-161. PMID: 28076806
- Photic generation of 11-cis-retinal in bovine retinal pigment epithelium. | Zhang, J., et al. 2019. J Biol Chem. 294: 19137-19154. PMID: 31694912
- Relative Contributions of All-Trans and 11-Cis Retinal to Formation of Lipofuscin and A2E Accumulating in Mouse Retinal Pigment Epithelium. | Boyer, NP., et al. 2021. Invest Ophthalmol Vis Sci. 62: 1. PMID: 33523199
- Polyenes and vision. | Rando, RR. 1996. Chem Biol. 3: 255-62. PMID: 8807853
Inhibitor of:
ABCA4, ATP-binding cassette sub-family A (ABCA), and OPN1SW.Activator of:
blue-sensitive opsin, OPN1MW2, and RDH16.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
11-cis Retinal, 500 µg | sc-208843 | 500 µg | $760.00 | |||
11-cis Retinal, 1 mg | sc-208843A | 1 mg | $1479.00 | |||
11-cis Retinal, 2 mg | sc-208843B | 2 mg | $2449.00 | |||
11-cis Retinal, 10 mg | sc-208843C | 10 mg | $12240.00 | |||
11-cis Retinal, 25 mg | sc-208843D | 25 mg | $26520.00 |