13-cis-Retinoic acid

• Catalog No.: R3255
• CAS Number: 4759-48-2
• M. F.: C20H28O2
• M. W.: 300.43512
• Purity: ≥98% (HPLC)

SYNONYMS

• IUPAC name: (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: isotretinoin
• Synonyms: Isotretinoin

DATABASE IDS

• PubChem SID: 24278676
• CAS Number: 4759-48-2
• EC Number: 225-296-0
• MDL Number: MFCD00079542

PROPERTIES

• Purity: ≥98% (HPLC)
• Gene Information: human ... NOS2(4843), RARA(5914), RARB(5915)
• Melting Point: 172-175 °C(lit.)
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H335-H360
• European Hazard Symbols: Toxic (T)
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• GHS Precautionary statements: P201-P261-P305 + P351 + P338-P308 + P313
• Risk Statements: 61-36/37/38
• RTECS: VH6440000
• Safety Statements: 53-26-36/37/39-45
• Storage Temperature: -20°C
• German water hazard class: 3

DETAILS

Description (English)

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.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R3255.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.