R4643

9-cis-Retinoic acid

≥98% (HPLC)

• Sinônimo(s): 9-cis-Tretinoin, Alitretinoin
• Fórmula empírica (Notação de Hill): C₂₀H₂₈O₂
• Número CAS: 5300-03-8
• Peso molecular: 300.44
• Número MDL: MFCD00270072
• Código UNSPSC: 12352106
• ID de substância PubChem: 24899373
• NACRES: NA.77

Propriedades

• fonte biológica: natural
• Nível de qualidade: 200
• Ensaio: ≥98% (HPLC)
• forma: powder
• técnica(s): HPLC: suitable
• cor: light yellow to yellow-orange
• pf: 189-190 °C
• temperatura de armazenamento: −20°C
• cadeia de caracteres 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+
• chave InChI: SHGAZHPCJJPHSC-ZVCIMWCZSA-N
• Informações sobre genes: human ... RARA(5914) , RARB(5915) , RARG(5916) , RXRA(6256) , RXRB(6257) , RXRG(6258)

Descrição

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Embalagem

Sealed ampule

Informações de segurança

• Pictogramas: GHS08,GHS07
• Palavra indicadora: Danger
• Frases de perigo: H315,H319,H335,H360
• Declarações de precaução: P201 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Classificações de perigo: Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Órgãos-alvo: Respiratory system
• Código de classe de armazenamento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges