R3255

13-cis-Retinoic acid

≥98% (HPLC)

• Synonyme(s) : Isotretinoin
• Formule empirique (notation de Hill) : C₂₀H₂₈O₂
• CAS Number: 4759-48-2
• Poids moléculaire : 300.44
• Numéro CE : 225-296-0
• Numéro MDL: MFCD00079542
• Code UNSPSC : 12352106
• ID de substance PubChem : 24278676
• Nomenclature NACRES : NA.77

Propriétés

• Essai: ≥98% (HPLC)
• Forme: powder
• Technique(s): HPLC: suitable
• Couleur: yellow to yellow-orange
• Pf: 172-175 °C (lit.)
• Température de stockage: −20°C
• Chaîne SMILES: [H]\C(C(O)=O)=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C
• 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-XFYACQKRSA-N
• Informations sur le gène: human ... NOS2(4843), RARA(5914), RARB(5915), RARG(5916)

Description

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Informations sur la sécurité

• Pictogrammes: GHS08,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H315,H319,H335,H360FD
• Conseils de prudence: P202 - P261 - P264 - 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