Molecular structure of 13-cis Retinal, CAS Number: 472-86-6
13-cis Retinal (CAS 472-86-6)
See product citations (2)
Alternate Names:
13-cis-Vitamin A aldehyde
Application:
13-cis Retinal is An isomer of all-trans-Retinal (sc-210778)
CAS Number:
472-86-6
Purity:
≥95%
Molecular Weight:
284.44
Molecular Formula:
C20H28O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
13-cis Retinal is an isomer of all-trans-Retinal (sc-210778).13-cis-Retinal, an isomer of retinal derived from vitamin A, is a component of the visual cycle, playing a fundamental role in the process of phototransduction and light perception. It undergoes conversion to 11-cis-retinal via the enzyme retinaldehyde isomerase, which then binds with opsin protein, forming the visual pigment rhodopsin. Upon exposure to light, rhodopsin activates, triggering a series of biochemical reactions that generate an electrical signal in the eye. By binding to opsin receptors, retinal initiates the photochemical conversion of light into nerve impulses. Moreover, this molecule exhibits anticancer properties by inhibiting cell division and inducing apoptosis.
13-cis Retinal (CAS 472-86-6) References
- Cellular metabolism and actions of 13-cis-retinoic acid. | Blaner, WS. 2001. J Am Acad Dermatol. 45: S129-35. PMID: 11606944
- All-trans to 13-cis retinal isomerization in light-adapted bacteriorhodopsin at acidic pH. | Chen, DL., et al. 2002. J Photochem Photobiol B. 66: 188-94. PMID: 11960728
- Crystal structure of the 13-cis isomer of bacteriorhodopsin in the dark-adapted state. | Nishikawa, T., et al. 2005. J Mol Biol. 352: 319-28. PMID: 16084526
- Bidirectional Photochemistry of Antarctic Microbial Rhodopsin: Emerging Trend of Ballistic Photoisomerization from the 13-cis Resting State. | Malakar, P., et al. 2022. J Phys Chem Lett. 13: 8134-8140. PMID: 36000820
- Interactions of all-trans, 9-, 11-, and 13-cis-retinal, all-trans-retinyl acetate, and retinoic acid with human retinol-binding protein and prealbumin. | Horwitz, J. and Heller, J. 1973. J Biol Chem. 248: 6317-24. PMID: 4199758
- Formation of 7-cis- and 13-cis-retinal pigments by irradiating squid rhodopsin. | Maeda, A., et al. 1979. Biochemistry. 18: 1449-53. PMID: 427126
- The catalytic isomerization of all-trans-retinal to 9-cis-retinal and 13-cis-retinal. | Futterman, S. and Rollins, MH. 1973. J Biol Chem. 248: 7773-9. PMID: 4750425
- Resonance Raman spectra of bacteriorhodopsin's primary photoproduct: evidence for a distorted 13-cis retinal chromophore. | Braiman, M. and Mathies, R. 1982. Proc Natl Acad Sci U S A. 79: 403-7. PMID: 6281770
- Reason for the lack of light-dark adaptation in pharaonis phoborhodopsin: reconstitution with 13-cis-retinal. | Hirayma, J., et al. 1995. FEBS Lett. 364: 168-70. PMID: 7750563
- Rat liver cytosolic retinal dehydrogenase: comparison of 13-cis-, 9-cis-, and all-trans-retinal as substrates and effects of cellular retinoid-binding proteins and retinoic acid on activity. | el Akawi, Z. and Napoli, JL. 1994. Biochemistry. 33: 1938-43. PMID: 8110799
- PHOTOCHEMICAL REACTION OF 13-CIS-BACTERIORHODOPSIN STUDIED BY LOW TEMPERATURE SPECTROPHOTOMETRY | and Tatsuo Iwasa, Fumio Tokunaga, Tǒru Yoshizawa. April 1981. Photochemistry and Photobiology. Volume33, Issue4: Pages 539-545.
- Vibrational analysis of the 13-cis-retinal chromophore in dark-adapted bacteriorhodopsin | Steven O. Smith, Johannes A. Pardoen, Johan. Lugtenburg, and Richard A. Mathies. 1987. J. Phys. Chem., 91, 4,: 804–819.
- Far-infrared vibrational spectra of all-trans, 9-cis and 13-cis retinal measured by THz time-domain spectroscopy | . December 2000,. Chemical Physics Letters. Volume 332, Issues 3–4, 22: Pages 389-395.
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
13-cis Retinal, 5 mg | sc-208857 | 5 mg | $458.00 | |||
13-cis Retinal, 10 mg | sc-208857A | 10 mg | $676.00 | |||
13-cis Retinal, 25 mg | sc-208857B | 25 mg | $1196.00 |