13-cis-Retinoic acid
SIGMA/R3255 - ≥98% (HPLC)
Synonym: Isotretinoin
CAS Number: 4759-48-2
Empirical Formula (Hill Notation): C20H28O2
Molecular Weight: 300.44
EC Number: 225-296-0
MDL Number: MFCD00079542
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) |
| color | yellow to yellow-orange |
| form | powder |
| InChI | 1S/C20H28O2/c1-15(8-6-9-1 |
| InChI key | SHGAZHPCJJPHSC-XFYACQKRSA |
| mp | 172-175 °C (lit.) |
| Quality Level | 200  |
| SMILES string | [H]C(C(O)=O)=C(C)C=CC= |
| storage temp. | −20°C |
| technique(s) | HPLC: suitable |
| Application: | 13-cis-Retinoic acid has been used: • as a component of fresh media for LA-N-5 differentiation • to treat medulloblastoma cells for cell differentiation • to treat spheroids for generating time-lapse videos • to examine its head- deforming activity under light and dark conditions in Xenopus laevis |
| Biochem/physiol Actions: | 13-cis-Retinoic acid (RA) has anti-inflammatory and anti-tumor action. The action of RA is mediated through RAR-β and RAR-α receptors. RA attenuates iNOS expression and activity in cytokine-stimulated murine mesangial cells. It induces mitochondrial membrane permeability transition, observed as swelling and as a decrease in membrane potential, and stimulates the release of cytochrome c implicating mechanisms through the apoptosis pathway. These activities are reversed by EGTA and cyclosporin A. RA also increases MMP-1 protein expression partially via increased transcription. |
| Features and Benefits: | This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm . |
| Packaging: | 100, 250, 500 mg in ampule |
| Symbol |   GHS07,GHS08 |
| Signal word | Danger |
| Hazard statements | H315 - H319 - H335 - H360 |
| Precautionary statements | P201 - P302 + P352 - P305 + P351 + P338 - P308 + P313 |
| Hazard Codes | T |
| Risk Statements | 61-36/37/38 |
| Safety Statements | 53-26-36/37/39-45 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98% (HPLC) |
| mp | 172-175 °C (lit.) |
| Storage Temp. | −20°C |
| UNSPSC | 12352106 |