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Merck

H7779

Retinoic acid p-hydroxyanilide

≥95%

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C26H33NO2
Numéro CAS:
65646-68-6
Poids moléculaire :
391.55
NACRES:
NA.77
PubChem Substance ID:
24278472
UNSPSC Code:
12352106
MDL number:
MFCD00792674

Principaux documents

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Nom du produit

Retinoic acid p-hydroxyanilide, ≥95%

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+

SMILES string

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

InChI key

AKJHMTWEGVYYSE-FXILSDISSA-N

biological source

synthetic (organic)

assay

≥95%

form

powder

color

yellow to yellow-orange

storage temp.

−20°C

Quality Level

200

Catégories apparentées

Application

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)

Biochem/physiol Actions

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.

General description

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

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

Classe de stockage

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

wgk

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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Certificats d'analyse (COA)

Lot/Batch Number
0000333414
0000333414
SLCR3508
SLCP4299
SLCJ6748

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    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. 

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

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

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

    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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