R4643

9-cis-Retinoic acid

≥98% (HPLC)

• Synonyme(s) : 9-cis-Tretinoin, Alitretinoin
• Formule empirique (notation de Hill): C₂₀H₂₈O₂
• Numéro CAS: 5300-03-8
• Poids moléculaire : 300.44
• Numéro MDL: MFCD00270072
• Code UNSPSC : 12352106
• ID de substance PubChem : 24899373
• Nomenclature NACRES : NA.77

Propriétés

• Source biologique: natural
• Niveau de qualité: 200
• Pureté: ≥98% (HPLC)
• Forme: powder
• Technique(s): HPLC: suitable
• Couleur: light yellow to yellow-orange
• Pf: 189-190 °C
• Température de stockage: −20°C
• Chaîne SMILES: 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+
• Clé InChI: SHGAZHPCJJPHSC-ZVCIMWCZSA-N
• Informations sur le gène: human ... RARA(5914) , RARB(5915) , RARG(5916) , RXRA(6256) , RXRB(6257) , RXRG(6258)

Description

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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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.

Conditionnement

Sealed ampule

Informations sur la sécurité

• Pictogrammes: GHS08,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H315,H319,H335,H360
• Conseils de prudence: P201 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Classification des risques: Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges