R2500

Sigma-Aldrich

all trans-Retinal

powder, ≥98%

Synonym(s):
Vitamin A aldehyde
Empirical Formula (Hill Notation):
C20H28O
CAS Number:
Molecular Weight:
284.44
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Quality Level

biological source

synthetic (organic)

assay

≥98%

form

powder

application(s)

HPLC: suitable

color

yellow

mp

62-64 °C

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H]C(=O)\C=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C

InChI

1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChI key

NCYCYZXNIZJOKI-OVSJKPMPSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

All trans-Retinal is one of the major derivatives of vitamin A group. A variety of food serves as a source of vitamin A. It is predominant in liver and among the brightly colored vegetables.

Application

All trans-Retinal has been used:
  • in optogenetic experiments
  • in electrophysiological experiment
  • to study the effect of AKR1B10 (aldo-keto reductase (AKR) superfamily member) on the conversion of retinal to retinol in the airway epithelium
  • in decidual transformation of human endometrial stromal cells

Packaging

25, 100, 500 mg in ampule
1 g in ampule
Sealed ampule.

Biochem/physiol Actions

All-trans retinal is converted to retinoic acid in vivo by the action of retinal dehydrogenase. Retinoic acid is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR) that act as transcription factors to regulate the growth and differentiation of normal and malignant cells. Retinal isomers are also chromophores that bind to opsins, a family of G-protein-linked transmembrane proteins, to form photosensitive receptors in visual and nonvisual systems. All-trans retinal is a potent photosensitizer.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R2500.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Certificate of Analysis

Certificate of Origin

Juan Antonio Sánchez-Alcañiz et al.
Nature communications, 9(1), 4252-4252 (2018-10-14)
Through analysis of the Drosophila ionotropic receptors (IRs), a family of variant ionotropic glutamate receptors, we reveal that most IRs are expressed in peripheral neuron populations in diverse gustatory organs in larvae and adults. We characterise IR56d, which defines two...
Optogenetic control of fly optomotor responses
Haikala V, et al.
The Journal of Neuroscience, 33(34), 13927-13934 (2013)
Advanced Nutrition Micronutrients, 23-23 (2019)
Smoking-induced upregulation of AKR1B10 expression in the airway epithelium of healthy individuals
Wang R, et al.
Chest, 138(6), 1402-1410 (2010)
Alexandria H Jaeger et al.
eLife, 7 (2018-10-12)
Each taste modality is generally encoded by a single, molecularly defined, population of sensory cells. However, salt stimulates multiple taste pathways in mammals and insects, suggesting a more complex code for salt taste. Here, we examine salt coding in Drosophila....
Articles
All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.
Read More
All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service