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Merck

H7779

Sigma-Aldrich

Retinoic acid p-hydroxyanilide

≥95%

Sinónimos:

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

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5 MG
MXP 4,424.00

MXP 4,424.00


Fecha estimada de envío16 de abril de 2025


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5 MG
MXP 4,424.00

About This Item

Fórmula empírica (notación de Hill):
C26H33NO2
Número de CAS:
Peso molecular:
391.55
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77

MXP 4,424.00


Fecha estimada de envío16 de abril de 2025


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biological source

synthetic (organic)

Quality Level

assay

≥95%

form

powder

color

yellow to yellow-orange

storage temp.

−20°C

SMILES string

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+

InChI key

AKJHMTWEGVYYSE-FXILSDISSA-N

General description

Retinoic acid p-hydroxyanilide is a synthetic analog of retinoid.[1]

Application

Retinoic acid p-hydroxyanilide has been used:
  • as a synthetic retinoid to induce apoptosis in SEB-1 sebocytes[1]
  • as a medium supplement for C2C12 myoblasts to test its effect on ceramide formation[2]
  • to test in cytotoxicity in T-cell acute lymphoblastic leukemia (T-ALL)[3]

Biochem/physiol Actions

Retinoic acid p-hydroxyanilide, also called fenretinide, increases reactive oxygen species, activates caspases and induces apoptosis.[1] It also inhibits dihydroceramide desaturase, leading to a decrease in ceramide biosynthesis.[2] Fenretinide may elicit anticancer activity in cultured human breast cancer cells.[2] It acts as an insulin antagonist and may be useful in treating insulin resistance.[2] Fenretinide or 4-HPR has chemotherapeutic potential and is cytotoxic to retinoic acid-resistant cancers.[3]
Vitamin A acid analogue with antiproliferative activity; induces apoptosis in malignant hemopoietic cell lines.

pictograms

Health hazardExclamation mark

signalword

Danger

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

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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Questions

1–3 of 3 Questions  
  1. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  2. How can one store a solution of product H7779, Retinoic acid p-hydroxyanilide?

    1 answer
    1. A solution of product H7779, Retinoic acid p-hydroxyanilide, can be aliquoted and stored at -20°C for up to 3 months. Solutions should be protect from light.

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  3. In what solvents can product H7779, Retinoic acid p-hydroxyanilide, be dissolved?

    1 answer
    1. Product H7779, Retinoic acid p-hydroxyanilide, can be dissolved in DMSO (25 mg/ml) and ethanol (25 mg/ml).

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