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all-trans Retinal (CAS 116-31-4) - chemical structure image
Molecular structure of all-trans Retinal, CAS Number: 116-31-4
all-trans Retinal (CAS 116-31-4) - chemical structure image
Molecular structure of all-trans Retinal, CAS Number: 116-31-4
Molecular structure of all-trans Retinal, CAS Number: 116-31-4

all-trans Retinal (CAS 116-31-4)

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Alternate Names:
all-trans Retinal is also known as Vitamin A aldehyde.
Application:
all-trans Retinal is an oxidized form of retinol, which is a corotenoid component of the visual pigments.
CAS Number:
116-31-4
Purity:
≥97%
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

All-trans retinal, a derivative of vitamin A, plays a pivotal role in the biochemistry of vision, acting as a key intermediate in the visual cycle. It functions by binding to opsin proteins in the photoreceptor cells of the retina, forming rhodopsin, which is essential for the conversion of light into electrical signals in the process of vision. Upon absorption of light, all-trans retinal isomerizes to its 11-cis form, initiating a cascade of biochemical events that result in a change in cell membrane potential and the transmission of nerve impulses to the brain. This property makes all-trans retinal invaluable in research focused on understanding the molecular basis of vision and the mechanics of phototransduction. Its role is also critical in the study of retinal diseases, offering insights into potential mechanisms for protecting against photoreceptor damage or degradation. Beyond vision, all-trans retinal is explored in the field of optogenetics, where it is used to control the activity of genetically modified neurons with light, providing a powerful tool for dissecting neural circuits and understanding brain function.


all-trans Retinal (CAS 116-31-4) References

  1. Identification and characterization of all-trans-retinol dehydrogenase from photoreceptor outer segments, the visual cycle enzyme that reduces all-trans-retinal to all-trans-retinol.  |  Rattner, A., et al. 2000. J Biol Chem. 275: 11034-43. PMID: 10753906
  2. Retinoid-binding proteins: mediators of retinoid action.  |  Noy, N. 2000. Biochem J. 348 Pt 3: 481-95. PMID: 10839978
  3. Studies on vitamin A: 5. The preparation of retinene(1)-vitamin A aldehyde.  |  Ball, S., et al. 1948. Biochem J. 42: 516-23. PMID: 16748320
  4. Retinopathy in mice induced by disrupted all-trans-retinal clearance.  |  Maeda, A., et al. 2008. J Biol Chem. 283: 26684-93. PMID: 18658157
  5. Involvement of all-trans-retinal in acute light-induced retinopathy of mice.  |  Maeda, A., et al. 2009. J Biol Chem. 284: 15173-83. PMID: 19304658
  6. Limited roles of Rdh8, Rdh12, and Abca4 in all-trans-retinal clearance in mouse retina.  |  Maeda, A., et al. 2009. Invest Ophthalmol Vis Sci. 50: 5435-43. PMID: 19553623
  7. Comparison of A2E cytotoxicity and phototoxicity with all-trans-retinal in human retinal pigment epithelial cells.  |  Wielgus, AR., et al. 2010. Photochem Photobiol. 86: 781-91. PMID: 20497365
  8. Key enzymes of the retinoid (visual) cycle in vertebrate retina.  |  Kiser, PD., et al. 2012. Biochim Biophys Acta. 1821: 137-51. PMID: 21447403
  9. Mechanism of all-trans-retinal toxicity with implications for stargardt disease and age-related macular degeneration.  |  Chen, Y., et al. 2012. J Biol Chem. 287: 5059-69. PMID: 22184108
  10. Reduction of all-trans-retinal in vertebrate rod photoreceptors requires the combined action of RDH8 and RDH12.  |  Chen, C., et al. 2012. J Biol Chem. 287: 24662-70. PMID: 22621924
  11. Tuning the electronic absorption of protein-embedded all-trans-retinal.  |  Wang, W., et al. 2012. Science. 338: 1340-3. PMID: 23224553
  12. Photoreceptor proteins initiate microglial activation via Toll-like receptor 4 in retinal degeneration mediated by all-trans-retinal.  |  Kohno, H., et al. 2013. J Biol Chem. 288: 15326-41. PMID: 23572532
  13. Retinal Pigment Epithelium Cell Death Is Associated With NLRP3 Inflammasome Activation by All-trans Retinal.  |  Liao, Y., et al. 2019. Invest Ophthalmol Vis Sci. 60: 3034-3045. PMID: 31311035
  14. Biotransformation of all-trans-retinol and all-trans-retinal to all-trans-retinoic acid in rat conceptal homogenates.  |  Chen, H., et al. 1995. Biochem Pharmacol. 50: 1257-64. PMID: 7488242
  15. Opsin/all-trans-retinal complex activates transducin by different mechanisms than photolyzed rhodopsin.  |  Jäger, S., et al. 1996. Biochemistry. 35: 2901-8. PMID: 8608127
  16. Reduction of all-trans-retinal limits regeneration of visual pigment in mice.  |  Saari, JC., et al. 1998. Vision Res. 38: 1325-33. PMID: 9667000

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

all-trans Retinal, 250 mg

sc-210778A
250 mg
$129.00

all-trans Retinal, 1 g

sc-210778
1 g
$379.00

Does all-trans-retinal degrade above 60oC?

Asked by: Jake573
Thank you for your question. It would be helpful if you could call 800-457-3801, allowing for a more interactive discussion of this and other related questions.
Answered by: Technical Service
Date published: 2022-05-18

Is sc-210778 synthetic or from an animal, a microbial, or a plant source?

Asked by: ChemSynth123
Thank you for your question. all-trans Retinal (CAS 116-31-4): sc-210778 is synthetic.
Answered by: Chemical Support 7
Date published: 2017-03-01

I stored sc-210778 at 2-8ºC for 2-3 days instead of the recommended -20ºC. Is this chemical still viable?

Asked by: ChemSynth123
Thank you for your question. all-trans Retinal (CAS 116-31-4): sc-210778 is still viable if stored at 2-8° C for 2-3 days. However, storing all-trans Retinal at a temperature higher than -20º C may reduce its shelf-life.
Answered by: Chemical Support 7
Date published: 2017-03-01

Do you have any information about activity in IU (International Units) of this compound?

Asked by: two2igm05
Thank you for your question. This chemical, all-trans Retinal (CAS 116-31-4) is a pigment and not an antibiotic. Therefore the product does not present any activity.
Answered by: Technical Support
Date published: 2016-12-24
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Rated 5 out of 5 by from all-trans Retinalall-trans Retinal is an oxidized form of retinol, which is a corotenoid component of the visual pigments. It is necessary to mimic RPE cells in an aging form. This pigment has autofluorescence and when cells were laden with it, it look like green fluorescences granules.
Date published: 2022-02-03
Rated 5 out of 5 by from WangWang, J. et al. (PubMed 26045160) reported an ultrahigh-performance liquid chromatography tandem mass spectrometry method to quantify all-trans Retinal in biological samples of limited size (15-35mg). This assay revealed that extraocular concentrations of retinal range from approximately 2 to 40pmol/g in multiple tissues-the same range as all-trans-retinoic acid. -SCBT Publication Review
Date published: 2015-04-10
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all-trans Retinal | CAS 116-31-4 is rated 5.0 out of 5 by 2.
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