ChemicalBook--->CAS DataBase List--->65646-68-6

65646-68-6

65646-68-6 Structure

65646-68-6 Structure
IdentificationMore
[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 PropertiesBack 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
[biological source]

synthetic (organic)
[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
[SMILES]

C(NC1=CC=C(O)C=C1)(=O)/C=C(/C=C/C=C(/C=C/C1C(C)(C)CCCC=1C)\C)\C
[CAS DataBase Reference]

65646-68-6(CAS DataBase Reference)
Safety DataBack 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
[Storage Class]

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
[Hazard Classifications]

Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Repr. 1B
Skin Irrit. 2
STOT SE 3
Hazard InformationBack 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.
Spectrum DetailBack Directory
[Spectrum Detail]

4-HYDROXYPHENYLRETINAMIDE(65646-68-6)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

65646-68-6(sigmaaldrich)
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