R2500

all trans-Retinal

powder, ≥98%

• Synonym(s): Vitamin A aldehyde
• Empirical Formula (Hill Notation): C₂₀H₂₈O
• CAS Number: 116-31-4
• Molecular Weight: 284.44
• MDL number: MFCD00001550
• PubChem Substance ID: 24899355
• NACRES: NA.79

Properties

• Quality Level: 200
• biological source: synthetic (organic)
• assay: ≥98%
• form: powder
• technique(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

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.