| Identification | More | [Name]
4-HYDROXYPHENYLRETINAMIDE | [CAS]
65646-68-6 | [Synonyms]
4HPR
4-HYDROXYPHENYLRETINAMIDE
FENRETINIDE
N-(4-HYDROXYPHENYL)-ALL-TRANS RETINAMIDE
N-(4-HYDROXYPHENYL)RETINAMIDE
RETINAMIDE
RETINOIC ACID P-HYDROXYANILIDE
hpr
n-(4-hydroxyphenyl)-retinamid
p-Hydroxyphenylretinamide
4-HPR, Fenretinide, N-(4-Hydroxyphenyl)retinamide
(2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenamide
Fenretinimide | [EINECS(EC#)]
200-256-5 | [Molecular Formula]
C26H33NO2 | [MDL Number]
MFCD00792674 | [Molecular Weight]
391.55 | [MOL File]
65646-68-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Powder | [Melting point ]
162-163°C | [Boiling point ]
597.6±42.0 °C(Predicted) | [density ]
1.081±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Orange solid | [pka]
9.98±0.26(Predicted) | [color ]
Yellow | [Usage]
An effective agent for the chemoprevention and growth modulation of oncogene-induced prostate cancer in the mouse prostate reconstitution model system and may be effective for the chemoprevention of human prostate cancer | [λmax]
362nm(MeOH)(lit.) | [Merck ]
14,3998 | [Stability:]
Light Sensitive - Protect from Light Exposure | [InChIKey]
AKJHMTWEGVYYSE-FXILSDISSA-N | [CAS DataBase Reference]
65646-68-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
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 Statements ]
S53:Avoid exposure-obtain special instruction 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 label where possible) . | [WGK Germany ]
3
| [RTECS ]
VH6420000
| [HS Code ]
2924297099 |
| Hazard Information | Back Directory | [Chemical Properties]
4-HYDROXYPHENYLRETINAMIDE is Yellow Powder
| [Uses]
4-HYDROXYPHENYLRETINAMIDE is an effective agent for the chemoprevention and growth modulation of oncogene-induced prostate cancer in the mouse prostate reconstitution model system and may be effective for the chemoprevention of human prostate cancer
| [Uses]
A synthetic analog of Vitamin A. | [Uses]
Retinoic acid receptor ligand | [Definition]
ChEBI: A retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in
ivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids. | [General Description]
Retinoic acid p-hydroxyanilide is a synthetic analog of retinoid. | [Biological Activity]
Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo . Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids. | [Biochem/physiol Actions]
Vitamin A acid analogue with antiproliferative activity; induces apoptosis in malignant hemopoietic cell lines. | [storage]
Store at -20°C, filled inert atmosphere | [References]
[1] roberto benelli, stefano monteghirfo, roberta venè, francesca tosettiand nicoletta ferrari.the chemopreventive retinoid 4hpr impairs prostate cancer cell migration and invasion by interfering with fak/akt/gsk3β pathway andβ-catenin stability. molecular cancer.2010, 9:142-154.
[2] anita l. sabichi, denver t. hendricks, mary a. bober, michael j. birrer. retinoic acid receptorβexpression and growthinhibition of gynecologic cancer cells by thesynthetic retinoidn-(4-hydroxyphenyl) retinamide. journal of the national cancer institute. 1998, 90(8): 597-605.
[3] shi-yong sun, ping yue, and reuben lotan. induction of apoptosis by n-(4-hydroxyphenyl)retinamide andits association with reactive oxygen species, nuclearretinoic acid receptors, and apoptosis-related genes in human prostate carcinoma cells.molecular pharmacology. 1999, 55:403–410. |
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