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Stemgent Stemolecule All-Trans Retinoic Acid

Code: 04-0021-base
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Stemolecule All-Trans Retinoic Acid is the oxidized form of Vitamin A and functions as a signaling molecule for various developmental pathways that control differentiation and proliferation1,2. It acts by binding to heterodimers of the retinoic acid receptor (RAR) and the retinoid × receptor (RXR), which then bind to retinoic acid response elements (RAREs) in the regulatory regions activating gene transcription3. All-Trans Retinoic Acid has been implicated in specification of the embryonic anterior/posterior axis through Hox gene regulation4. It has been used in various differentiation protocols, including B-cells, T-cells and neurons and applied clinically to treat cancer as a form of differentiation-induction therapy2,5-11.

Product Name

Stemolecule All-Trans Retinoic Acid

Catalog Number

04-0021

Size

100 mg

Alternate Name(s)

  • ATRA
  • (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid

Chemical Formula

C20H28O2

Molecular Weight

300.44

CAS Number

302-79-4

Purity

Greater than 98% by HPLC analysis

Formulation

Yellow to light orange crystalline powder

Solubility

For a 10 mM concentrated stock solution of All-Trans Retinoic Acid, add 1.66mL of DMSO to 5mg of the compound. If a precipitate is observed, warm the solution to 37°C for 2 to 5 minutes. For cell culture, the media should be prewarmed prior to adding the reconstituted compound. Note: for most cells, the maximum tolerance to DMSO is less than 0.5%. This molecule is soluble in DMSO at 100 mM and 95% ethanol at 9 mM.

Storage and Stability

Store powder at 4°C protected from light. Information about the stability of Stemolecules in solution is largely not available. As a general guideline, we recommend that stock solution be freshly made and stored in aliquots at −20°C. The effect of storage of stock solutions should be verified for each application.

Quality Control

The purity of All-Trans Retinoic Acid was determined by HPLC analysis. The accurate mass was determined by mass spectrometry. Cellular toxicity of All-Trans Retinoic Acid was tested on mouse embryonic stem cells.

Specification Sheets

Safety Data Sheets

  1. Duester, G. Retinoic acid synthesis and signaling during early organogenesis. Cell 134: 921-931 (2008).
  2. Ertesvåg, A., Naderi, S., Blomhoff, H.K. Regulation of B cell proliferation and differentiation by retinoic acid. Semin Immunol 21: 36-41 (2009).
  3. Marshall, H., Morrison, A., Studer, M., Pöpperl, H. and Krumlauf, R. Retinoids and Hox genes. FASEB J 10: 969-978 (1996).
  4. Holland, L.Z. Developmental biology: a chordate with a difference. Nature 447: 153-155 (2007).
  5. Yagi, J., Uchida, T., Kuroda, K., and Uchiyama, T. Influence of retinoic acid on the differentiation pathway of T-cells in the thymus. Cell Immunol 181: 153-162 (1997).
  6. Dhara, S.K., and Stice, S.L. Neural differentiation of human embryonic stem cells. J Cell Biochem 105: 633-640 (2008).
  7. Sasai, Y. Generation of dopaminergic neurons from embryonic stem cells. J Neurol 249 Suppl 2: II41-1144 (2002).
  8. Takahashi, J., Palmer, T.D., and Gage, F.H. Retinoic acid and neurotrophins collaborate to regulate neurogenesis in adult-derived neural stem cell cultures. J Neurobiol 38: 65-81 (1999).
  9. Wichterle, H., Lieberam, I., Porter, J.A., and Jessell, T.M. Directed differentiation of embryonic stem cells into motor neurons. Cell 110: 385-397 (2002).
  10. Collins, S.J. Retinoic acid receptors, hematopoiesis and leukemogenesis. Curr Opin Hematol 15: 346-351 (2008).
  11. Mongan, N.P., and Gudas, L.J. Diverse actions of retinoid receptors in cancer prevention and treatment. Differentiation 75: 853-870 (2007).

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