R3255

13-cis-Retinoic acid

≥98% (HPLC)

• Synonym(s): Isotretinoin
• Empirical Formula (Hill Notation): C₂₀H₂₈O₂
• CAS Number: 4759-48-2
• Molecular Weight: 300.44
• EC Number: 225-296-0
• MDL number: MFCD00079542
• UNSPSC Code: 12352106
• PubChem Substance ID: 24278676
• NACRES: NA.77

Properties

• assay: ≥98% (HPLC)
• form: powder
• technique(s): HPLC: suitable
• color: yellow to yellow-orange
• mp: 172-175 °C (lit.)
• storage temp.: −20°C
• SMILES string: [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-
• InChI key: SHGAZHPCJJPHSC-XFYACQKRSA-N
• Gene Information: 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

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.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H315,H319,H335,H360FD
• pcodes: P202 - P261 - P264 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges