(2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenamide
Fenretinide
CAS: 65646-68-6
Molecular Formula: C26H33NO2
(2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenamide - Names and Identifiers
(2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenamide - Physico-chemical Properties
| Molecular Formula | C26H33NO2 |
| Molar Mass | 391.55 |
| Density | 1.081±0.06 g/cm3(Predicted) |
| Melting Point | 162-163°C |
| Boling Point | 597.6±42.0 °C(Predicted) |
| Solubility | Soluble in DMSO (25 mg/ml), ethanol (25 mg/ml)), chloroform, and acetone (easily soluble |
| Appearance | Orange solid |
| Color | Yellow |
| Maximum wavelength(λmax) | 362nm(MeOH)(lit.) |
| Merck | 14,3998 |
| pKa | 9.98±0.26(Predicted) |
| Storage Condition | -20°C |
| Stability | Light Sensitive - Protect from Light Exposure |
| Sensitive | Sensitive to heat and air |
| MDL | MFCD00792674 |
| Use | An agonist displaying activity at retinoid receptors |
| In vitro study | Fenretinide (4-HPR) exerts not just acute but also long term antitumor activity in selected T-ALL cell lines. Fenretinide inhibits DES activity in CCRF-CEM leukemia cells in a dose and time dependent manner, leading to a concomitant increase of the endogenous cellular dhCer content. Fenretinide (3 μM)-induced dhCer accumulation in both CCRF-CEM and Jurkat cells. Ceramide inhibition with fenretinide protects insulin signaling. Fenretinide prevents lipid-induced reductions in insulin-stimulated glucose uptake. Fenretinide inhibits OVCAR-5 cell proliferation and viability at concentrations higher than 1 microM, with 70-90% growth inhibition at 10 microM. Fenretinide (1 microM) significantly inhibits OVCAR-5 invasion after 3 days preincubation. Endothelial cells treated with 1 microM 4-HPR fails to form tubes, but forms small cellular aggregates. |
| In vivo study | Fenretinide (4-HPR) (10 mg/kg, i.p.) selectively inhibits ceramide accumulation HFD-fed male C57Bl/6 mice. Fenretinide treatment improves glucose tolerance and insulin sensitivity as determined by both glucose and insulin tolerance tests. Addition of 25 mg/kg ketoconazole to Fenretinide in NOD/SCID mice increased 4-HPR plasma levels. |
(2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenamide - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R60 - May impair fertility R61 - May cause harm to the unborn child R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. 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.) S52 - Not recommended for interior use on large surface areas. |
| WGK Germany | 3 |
| RTECS | VH6420000 |
(2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenamide - Introduction
Fenretinide (4-HPR) is a synthetic retinoic acid derivative that can bind to retinoic acid receptor (RAR).
Last Update：2022-10-16 17:41:45
(2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenamide - Reference Information
| biological activity | Fenretinide (4-HPR) is a synthetic retinoid derivative that can bind to retinoic acid receptor (RAR) to induce cell death. |
| in vitro study | Fenretinide (4-HPR) results not just acute but also long term antitumor activity in selected T-ALL cell lines. Fenretinide inhibits DES activity in CCRF-CEM leukemia cells in a dose and time dependent manner, leading to a concomitant increase of the endogenous cellular dhCer content. Fenretinide (3 μM)-induced dhCer accumulation in both CCRF-CEM and Jurkat cells. Ceramide inhibition with fenretinide protects insulin signaling. Fenretinide prevents lipid-induced reductions in insulin-stimulated glucose uptake. Fenretinide inhibits OVCAR-5 cell proliferation and viability at concentrations higher than 1 microM, with 70-90% growth inhibition at 10 microM. Fenretinide (1 microM) significantly inhibits OVCAR-5 invasion after 3 days preincubation. Endothelial cells treated with 1 microM 4-HPR fail to form tubes, but forms small cellular aggregates. |
| in vivo study | Fenretinide (4-HPR) (10 mg/kg, I. p.) selectively inhibits ceramide accumulation HFD-fed male C57Bl/6 mice. Fenretinide treatment improves glucose tolerance and insulin sensitivity as determined by both glucose and insulin tolerance tests. Addition of 25 mg/kg ketoconazole to Fenretinide in NOD/SCID mice increased 4-HPR plasma levels. |
Last Update：2024-04-09 02:00:02
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Product Name: Fenretinide Visit Supplier Webpage Request for quotationCAS: 65646-68-6
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Mobile: 18021002903
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