R4643

9-cis-Retinoic acid

≥98% (HPLC)

• Synonym(e): 9-cis-Tretinoin, Alitretinoin
• Empirische Formel (Hill-System): C₂₀H₂₈O₂
• CAS-Nummer: 5300-03-8
• Molekulargewicht: 300.44
• MDL-Nummer: MFCD00270072
• UNSPSC-Code: 12352106
• PubChem Substanz-ID: 24899373
• NACRES: NA.77

Eigenschaften

• Biologische Quelle: natural
• Qualitätsniveau: 200
• Assay: ≥98% (HPLC)
• Form: powder
• Methode(n): HPLC: suitable
• Farbe: light yellow to yellow-orange
• mp (Schmelzpunkt): 189-190 °C
• Lagertemp.: −20°C
• SMILES String: CC1=C(\C=C\C(C)=C/C=C/C(C)=C/C(O)=O)C(C)(C)CCC1
• InChI: 1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
• InChIKey: SHGAZHPCJJPHSC-ZVCIMWCZSA-N
• Angaben zum Gen: human ... RARA(5914) , RARB(5915) , RARG(5916) , RXRA(6256) , RXRB(6257) , RXRG(6258)

Beschreibung

Anwendung

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-glucuronosyltransferases (UGT) expression in thyroid induced hepatocytes
• to induce lymphangiogenesis in lymphatic endothelial cell

Biochem./physiol. Wirkung

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.

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.

Leistungsmerkmale und Vorteile

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.

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.

Verpackung

verschweisste Ampulle

Sicherheitshinweise

• Piktogramme: GHS08,GHS07
• Signalwort: Danger
• H-Sätze: H315,H319,H335,H360
• P-Sätze: P201 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Gefahreneinstufungen: Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges