Retinoic acid
SIGMA/R2625 - ≥98% (HPLC), powder
Synonym: ATRA; Tretinoin; Vitamin A acid; all-trans-Retinoic acid
CAS Number: 302-79-4
Empirical Formula (Hill Notation): C20H28O2
Molecular Weight: 300.44
EC Number: 206-129-0
MDL Number: MFCD00001551
Linear Formula: C20H28O2
Product Type: Chemical
Representative of vacuum-sealed clear ampule packaging. Non-uniform tips are an inherent feature in this sealing process.
| assay | ≥98% (HPLC) |
| biological source | synthetic (organic) |
| color | yellow |
| form | powder |
| InChI | 1S/C20H28O2/c1-15(8-6-9-1 |
| InChI key | SHGAZHPCJJPHSC-YCNIQYBTSA |
| mp | 180-181 °C (lit.) |
| Quality Level | 200  |
| SMILES string | CC1=C(C=CC(C)=CC=CC(C |
| solubility | chloroform: 50 mg/mL |
| storage temp. | −20°C |
| technique(s) | cell culture | mammalian: suitable |
| Application: | • Retinoic acid (RA) has been used for the differentiation of embryonic stem cells into motor neurons. • It has been used for the differentiation of Xenopus ectoderm into pancreas. • It has also been used to study epigenetic regulation by RARα (retinoic acid receptor α). • It has been used to study RA signaling of prospermatogonia transition into spermatogonia. |
| Biochem/physiol Actions: | all−trans−Retinoic acid (ATRA) is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR). The bound RAR and RXR act as transcription factors that regulate the growth and differentiation of both normal and malignant cells. Cytochromes P450 (CYPs) catalyze the 4-hydroxylation of ATRA. Retinoic acid primes embryonic stem cells to become neurons. |
| Biochem/physiol Actions: | Ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR); primes embryonic stem cells to become neurons. |
| Features and Benefits: | This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here . |
| General description: | Retinoic acid (RA), a retinoid, exerts a broad range of biological effects. It plays a role in regulating cellular differentiation and proliferation in both normal and transformed cells, potentially influencing oncogenes. All-trans retinoic acid (ATRA) is regarded as the most pertinent and functionally active metabolite of Vitamin-A. RA may serve as a type of signal molecule through a nuclear receptor to regulate regional differentiation in the central nervous system. Moreover, at a concentration of 1 nM (with maximal differentiation at 1 µM), RA induces morphological and functional terminal differentiation in a cell line of human promyelocyte leukemia, indicating its potential involvement in the differentiation of specific hematopoietic cells. Additionally, RA can indirectly impact neuronal differentiation by modifying the expression of neuronal cell surface receptors to peptide growth factors. Furthermore, RA and other retinoids can also inhibit cellular proliferation and stimulate tyrosinase activity in a human melanoma cell line, while also inhibiting cell-substrate adhesion and motility in melanocytes. ATRA plays a vital role in the formation of the mammalian vascular system. Specifically, it regulates endothelial cell proliferation and vascular remodeling throughout tissue angiogenesis. |
| Other Notes: | 2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research  |
| Packaging: | 1, 5 g in ampule |
| Packaging: | 50, 100, 500 mg in ampule |
| Symbol |    GHS07,GHS08,GHS09 |
| Signal word | Danger |
| Hazard statements | H302 - H315 - H360FD - H410 |
| Precautionary statements | P202 - P264 - P273 - P301 + P312 - P302 + P352 - P308 + P313 |
| Hazard Codes | Xn |
| Risk Statements | 22 |
| Safety Statements | 61 |
| RIDADR | UN 3077 9 / PGIII |
| WGK Germany | WGK 2 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98% (HPLC) |
| mp | 180-181 °C (lit.) |
| Storage Temp. | −20°C |
| UNSPSC | 12352106 |