9-cis-Retinoic acid
SIGMA/R4643 - ≥98% (HPLC)
Synonym: 9-cis-Tretinoin; Alitretinoin
CAS Number: 5300-03-8
Empirical Formula (Hill Notation): C20H28O2
Molecular Weight: 300.44
MDL Number: MFCD00270072
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 | natural |
| color | light yellow to yellow-orange |
| form | powder |
| InChI | 1S/C20H28O2/c1-15(8-6-9-1 |
| InChI key | SHGAZHPCJJPHSC-ZVCIMWCZSA |
| mp | 189-190 °C |
| Quality Level | 200  |
| SMILES string | CC1=C(C=CC(C)=C/C=C/C(C |
| storage temp. | −20°C |
| technique(s) | HPLC: suitable |
| Application: | 9-cis-Retinoic acid has been used: • as ligand for retinoid X receptor gamma (RXRγ) for inducing oligodendrocyte precursor cells differentiation and remyelination • as a medium component to study its effect on UDP-glucuronosyltransfera • to induce lymphangiogenesis in lymphatic endothelial cell |
| Biochem/physiol Actions: | 9-cis-Retinoic acid (9cRA) is an isomer of all-trans-retinoic acid (ATRA), both of which are lipid molecules synthesized from a common precursor, vitamin A. 9cRA is a potent agonist for retinoid X receptor (RXR) and retinoic acid receptor (RAR). It has neurotrophic functionality, promotes neuronal differentiation and may have therapeutic potential in treating stroke. It also regulates cytokine secretion and lymphocyte proliferation. 9cRA favors the dopamine cells survival and induces neuroprotection in neurodegenerative disorder like parkinson′s disease. It elicits anti-inflammatory function and stimulates mast cells and inhibits interleukin 4 and 5 expression levels. 9cRA is in clinical trial phase II for treating refractory cancer. |
| Biochem/physiol Actions: | 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. |
| 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 . |
| 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 . |
| Packaging: | 1 mg in ampule |
| Packaging: | Sealed 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 | 189-190 °C |
| Storage Temp. | −20°C |
| UNSPSC | 12352106 |