R4643

9-cis-Retinoic acid

≥98% (HPLC)

• Synonym(s): 9-cis-Tretinoin, Alitretinoin
• Empirical Formula (Hill Notation): C₂₀H₂₈O₂
• CAS Number: 5300-03-8
• Molecular Weight: 300.44
• MDL number: MFCD00270072
• UNSPSC Code: 12352106
• PubChem Substance ID: 24899373
• NACRES: NA.77

Properties

• biological source: natural
• Assay: ≥98% (HPLC)
• form: powder
• technique(s): HPLC: suitable
• color: light yellow to yellow-orange
• mp: 189-190 °C
• storage temp.: −20°C
• SMILES string: 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+
• InChI key: SHGAZHPCJJPHSC-ZVCIMWCZSA-N
• Gene Information: 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

Biochem/physiol Actions

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.

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.

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.

Packaging

Sealed ampule

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H315,H319,H335,H360
• Precautionary Statements: P201 - 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 Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves