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R2500 Sigma-Aldrich

all trans-Retinal

powder, ≥98%

Synonym: Vitamin A aldehyde

  • CAS Number 116-31-4

  • Empirical Formula (Hill Notation) C20H28O

  • Molecular Weight 284.44

  •  MDL number MFCD00001550

  •  PubChem Substance ID 24899355

  •  NACRES NA.79

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Properties

Related Categories Aldehydes, Antitumor Agents, Biochemicals and Reagents, Building Blocks, C13-C60,
Quality Level   200
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

Description

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

1 g in ampule

25, 100, 500 mg in 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.

Packaging

Sealed ampule.

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Retinoic Acid and Gene Expression

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, apopt...
BioFiles 2008, 3.9, 12.
Keywords: Apoptosis, Cancer, Cell proliferation, Cellular processes, Chromatin immunoprecipitation, Condensations, Degradations, Diseases, Gene expression, Hormones, Immunoprecipitation, Ligands, Metabolism, Oxidations, Phosphorylations, Polymerase chain reaction, Sequences, Teratogens, Transcription, Type, Ubiquitinations, Usage, Vitamins

Peer-Reviewed Papers
15

References

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