CAS 5300-03-8|Alitretinoin
| Common Name | Alitretinoin | ||
|---|---|---|---|
| CAS Number | 5300-03-8 | Molecular Weight | 300.435 |
| Density | 1.0±0.1 g/cm3 | Boiling Point | 462.8±14.0 °C at 760 mmHg |
| Molecular Formula | C20H28O2 | Melting Point | 189-191ºC |
| MSDS | ChineseUSA | Flash Point | 350.6±11.0 °C |
| Symbol | GHS07, GHS08 | Signal Word | Danger |
Names
| Name | 9-cis-retinoic acid |
|---|---|
| Synonym | More Synonyms |
Alitretinoin BiologicalActivity
| Description | 9-cis-Retinoic acid (ALRT1057), a vitamin A derivative, is a potent RAR/RXR agonist. 9-cis-Retinoic acid induces apoptosis, regulates cell cycle and has anticancer, anti-inflammatory and neuroprotection activities[1][2][3][4][5]. |
|---|---|
| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>Inflammation/ImmunologyResearch Areas >>Neurological DiseaseSignaling Pathways >>Metabolic Enzyme/Protease >>RAR/RXR |
| In Vitro | 9-cis-Retinoic acid (1-10 μM; 0-5 days; CA 9-22 and NA cells) treatment significantly decreases proliferation in a dose-dependent manner in CA 9-22 and NA cells[1]. 9-cis-Retinoic acid (1 μM; 24 hours) treatment significantly increases PPARγ functional activity by >200% in CA 9-22 and NA aerodigestive cells[1]. 9-cis-Retinoic acid treatment results in the formation of a nuclear PPARγ-RXRα heterodimer supershift complex in CA 9-22 cells[1]. 9-cis-Retinoic acid inhibits proliferation and induces apoptosis in cutaneous T-cell lymphoma (CTCL) in a dose-dependent and time-dependent manner. 9-cis-Retinoic acid also induces G0/G1 cell cycle arrest by downregulation of cyclin D1. 9-cis-Retinoic acid significantly decreases phosphorylation of JAK1, STAT3, and STAT5 and downregulated Bcl-xL and cyclin D1[2]. Cell Proliferation Assay[1] Cell Line: CA 9-22 and NA cells Concentration: 1 μM, 10 μM Incubation Time: 0 day, 1 day, 3 days, 5 days Result: Significantly decreased proliferation. |
| In Vivo | 9-cis-Retinoic acid (1 mg/kg; intravenous injection; daily; for 10 days; male C57BL/6J mice) treatment significantly decreases the serum ALT and AST level, alleviates hepatic necrosis of the bile duct ligation (BDL)-mice[3]. Animal Model: Male C57BL/6J mice (6-8 weeks; 19-22 g) treatment with bile duct ligated[3] Dosage: 1 mg/kg Administration: Intravenous injection; daily; for 10 days Result: Significantly decreased the serum ALT and AST level, alleviated hepatic necrosis. |
| References | [1]. Raul Rosas, et al. Retinoids Augment Thiazolidinedione PPARγ Activation in Oral Cancer Cells. Anticancer Res. 2020 Jun;40(6):3071-3080. [2]. Hua Yang, et al. Effects of 9-cis-retinoic Acid on the Proliferation and Apoptosis of Cutaneous T-cell Lymphoma Cells. Anticancer Drugs. 2019 Jan;30(1):56-64. [3]. Zhiqing Yuan, et al. 9-cis-retinoic Acid Elevates MRP3 Expression by Inhibiting Sumoylation of RXRα to Alleviate Cholestatic Liver Injury. Biochem Biophys Res Commun. 2018 Sep 3;503(1):188-194. [4]. V M Manzano, et al. Human Renal Mesangial Cells Are a Target for the Anti-Inflammatory Action of 9-cis Retinoic Acid. Br J Pharmacol. 2000 Dec;131(8):1673-83. [5]. Gro H Mathisen, et al. Delayed Translocation of NGFI-B/RXR in Glutamate Stimulated Neurons Allows Late Protection by 9-cis Retinoic Acid. Biochem Biophys Res Commun. 2011 Oct 14;414(1):90-5. |
Chemical & Physical Properties
| Density | 1.0±0.1 g/cm3 |
|---|---|
| Boiling Point | 462.8±14.0 °C at 760 mmHg |
| Melting Point | 189-191ºC |
| Molecular Formula | C20H28O2 |
| Molecular Weight | 300.435 |
| Flash Point | 350.6±11.0 °C |
| Exact Mass | 300.208923 |
| PSA | 37.30000 |
| LogP | 6.83 |
| Vapour Pressure | 0.0±2.5 mmHg at 25°C |
| Index of Refraction | 1.556 |
| InChIKey | SHGAZHPCJJPHSC-ZVCIMWCZSA-N |
| SMILES | CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(=O)O |
| Storage condition | −20°C |
| Stability | Store Dry in Freezer at -20°C for up to 1 year; in Solution at -20°C for up to 3 Months. |
Safety Information
| Symbol | GHS07, GHS08 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H315-H319-H335-H360 |
| Precautionary Statements | P201-P261-P305 + P351 + P338-P308 + P313 |
| 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 |
| Hazard Codes | T: Toxic; |
| Risk Phrases | R36/37/38;R61 |
| Safety Phrases | S26-S36/37/39-S45-S53 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| HS Code | 2916209090 |
Customs
| HS Code | 2916209090 |
|---|---|
| Summary | 2916209090 other cyclanic, cyclenic or cyclotherpenic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0% |
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Synonyms
| 9-cis-Tretinoin,Alitretinoin |
| (9cis)-Retinoic acid |
| Alitretinoin |
| (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid |
| 9-cis-retinoic acid |
| MFCD00270072 |
| 9Z-retinoic acid |
| 9-cis-Tretinoin |
| 9-cis Retinoic Acid |
| Panretin Gel |
| (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid |
| Retinoic acid, (9cis)- |
| 9(Z)-Retinoic acid |
