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H7779

Sigma-Aldrich

Retinoic acid p-hydroxyanilide

≥95%

Sinónimos:

4-HPR, Fenretinide, N-(4-Hydroxyphenyl)retinamide

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About This Item

Fórmula empírica (notación de Hill):
C26H33NO2
Número de CAS:
65646-68-6
Peso molecular:
391.55
Número MDL:
MFCD00792674
Código UNSPSC:
12352106
ID de la sustancia en PubChem:
24278472
NACRES:
NA.77

origen biológico

synthetic (organic)

Nivel de calidad

200

Ensayo

≥95%

Formulario

powder

color

yellow to yellow-orange

temp. de almacenamiento

−20°C

cadena SMILES

CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(=O)Nc2ccc(O)cc2)C(C)(C)CCC1

InChI

1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+

Clave InChI

AKJHMTWEGVYYSE-FXILSDISSA-N

Categorías relacionadas

Descripción general

Retinoic acid p-hydroxyanilide is a synthetic analog of retinoid.

Aplicación

Retinoic acid p-hydroxyanilide has been used:
  • as a synthetic retinoid to induce apoptosis in SEB-1 sebocytes
  • as a medium supplement for C2C12 myoblasts to test its effect on ceramide formation
  • to test in cytotoxicity in T-cell acute lymphoblastic leukemia (T-ALL)

Acciones bioquímicas o fisiológicas

Retinoic acid p-hydroxyanilide, also called fenretinide, increases reactive oxygen species, activates caspases and induces apoptosis. It also inhibits dihydroceramide desaturase, leading to a decrease in ceramide biosynthesis. Fenretinide may elicit anticancer activity in cultured human breast cancer cells. It acts as an insulin antagonist and may be useful in treating insulin resistance. Fenretinide or 4-HPR has chemotherapeutic potential and is cytotoxic to retinoic acid-resistant cancers.
Vitamin A acid analogue with antiproliferative activity; induces apoptosis in malignant hemopoietic cell lines.

Pictogramas

Health hazardExclamation mark
GHS08,GHS07

Palabra de señalización

Danger

Clasificaciones de peligro

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
0000333414
SLCR3508
SLCP4299
SLCJ6748
SLCF5888

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Sigma-Aldrich

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Sigma-Aldrich

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The synthetic retinoid 4-hydroxyphenylretinamide (HPR) showed antiproliferative effect on cultured human breast cancer cells, which were sensitive to retinoic acid (RA) too. Investigation of the cell cycle by flow cytophotometry showed a significant increase of cells in the S-phase of
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