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
• Quality Level: 200
• 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[1]
• as a medium component to study its effect on UDP-glucuronosyltransferases (UGT) expression in thyroid induced hepatocytes[2]
• to induce lymphangiogenesis in lymphatic endothelial cell[3]

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.[4] 9cRA is a potent agonist for retinoid X receptor (RXR) and retinoic acid receptor (RAR).[5] It has neurotrophic functionality, promotes neuronal differentiation and may have therapeutic potential in treating stroke.[6] It also regulates cytokine secretion and lymphocyte proliferation.[4] 9cRA favors the dopamine cells survival and induces neuroprotection in neurodegenerative disorder like parkinson′s disease.[7] It elicits anti-inflammatory function and stimulates mast cells and inhibits interleukin 4 and 5 expression levels.[8] 9cRA is in clinical trial phase II for treating refractory cancer.[5]

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