9-cis-Retinoic acid
9-cis-retinoic acid
CAS: 5300-03-8
Molecular Formula: C20H28O2
9-cis-Retinoic acid - Names and Identifiers
| Name | 9-cis-retinoic acid |
| Synonyms | Alitretinoin 9-CIS-TRETINOIN 9-cis-tretinoin 9-CIS-RETINOIC ACID 9-cis-retinoic acid RARECHEM AL BE 0738 9-cis-Retinoic acid RETINOIC ACID, 9-CIS- Tretinoin EP Impurity D (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex (2E,4E,6Z,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYLCYCLOHEX-1-ENYL)NONA-2,4,6,8-TETRAENOIC ACID |
| CAS | 5300-03-8 |
| EINECS | 1533716-785-6 |
| InChI | InChI=1/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+ |
9-cis-Retinoic acid - Physico-chemical Properties
| Molecular Formula | C20H28O2 |
| Molar Mass | 300.44 |
| Density | 1.011±0.06 g/cm3(Predicted) |
| Melting Point | 189-191°C |
| Boling Point | 462.8±14.0 °C(Predicted) |
| Water Solubility | Soluble in chloroform (50 mg/ml), DMSO (~25 mg/ml), ethanol (25 mg/ml), and acetone (25 mg/ml). Insoluble in water. |
| Solubility | Acetonitrile (Very Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol ( |
| Appearance | Light yellow to orange crystalline powder. |
| Color | Pale Yellow to Yellow |
| pKa | 4.73±0.33(Predicted) |
| 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. |
| Sensitive | Moisture & Light Sensitive |
9-cis-Retinoic acid - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R61 - May cause harm to the unborn child R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| WGK Germany | 3 |
| RTECS | VH6450000 |
| HS Code | 29162090 |
9-cis-Retinoic acid - Reference Information
| Overview | Isotretinoin EP impurity D is an impurity produced during the synthesis of isotretinoin, also known as aliretinoic acid, which is an important drug in the field of skin diseases. It is all-trans retinoic acid (formula II, chemical name: 3, 7-dimethyl -9-(2,6, 6-trimethylcyclohexene -1-yl)-2E,4E,6E, 8E-all-trans non-tetraenoic acid) 9-cis isomer. |
| preparation | preparation of isotretinoin EP impurity d (compound of formula I): under the protection of nitrogen, 2L of ethanol and 100g of all-trans retinoic acid are added to the reaction bottle, stirred, then the temperature is increased to 50-55 ℃, and PdCl289mg is added. After 1.5h of reaction, the purity of the product detected by HPLC was 21%. The reaction solution was slowly cooled to 0~5 ℃, kept warm for 180 minutes, and filtered by suction. The filtrate was added to another clean reaction flask, continued to cool to -10 ~-6 ℃, kept warm for 20 minutes, filtered by suction, and the product isotretinoin EP impurity D 12.1g was obtained, the total yield was 12.1%, and the HPLC purity was 99.60%. Using all-trans retinoic acid as raw material and catalyzed by palladium compounds, aliretinoic acid can be obtained in ordinary industrial-grade organic solvents. The method is simple to operate, low in cost, controllable in conditions and convenient for industrial production. After post-treatment steps, aliretinoic acid with a purity of more than 99% can be obtained, and the product yield reaches more than 12%, which has high application value. |
| biological activity | 9-cis-Retinoic acid (ALRT1057), a derivative of vitamin A, is an effective RAR/RXR agonist. 9-cis-Retinoic acid induces apoptosis (apoptosis), regulates cell cycle and has anticancer, anti-inflammatory and neuroprotective activities. |
| 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. Significantly decreased the serum ALT and AST level, alleviated hepatic necrosis. |
| Animal Model: | Male C57BL/6J mice (6-8 weeks; 19-22 g) treatment with bile duct ligated |
| Dosage: | 1 mg/kg |
| Administration: | Intravenous injection; daily; for 10 days |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:32:06
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