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Safety Information

H7779

Sigma-Aldrich

Retinoic acid p-hydroxyanilide

≥95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C26H33NO2
CAS Number:
65646-68-6
Molecular Weight:
391.55
MDL number:
MFCD00792674
UNSPSC Code:
12352106
PubChem Substance ID:
24278472
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

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

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General description

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

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

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 Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (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?

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  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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Journal of the National Cancer Institute, 75(5), 871-875 (1985-11-01)
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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